Web Design Business with Josh Hall

421 - In-Person with Andy Milligan (on his successful but stressful 200k year)

Josh Hall

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A special interview here for a few reasons:

  1. This one is in-person so it has a completely different feel, dynamic and I have to admit, I LOVED it. Definitely inspiring me to do more in-person interviews with local colleagues.
  2. My guest (Web Designer Pro member Andy Milligan) just took his agency to 200k+ in revenue in 2025 from 30k in 2024. So massive growth, however, it came at a cost. We dig into the stressful side of quick success. 
  3. Andy asked awesome questions and we got into some topics I’ve never discussed publicly. Hats off to him for becoming such a great, thoughtful interviewer and host!

Lastly, I should note that I was coming off of a wicked sickness when we recorded so I was not even close 100% but alas, with 3 littles under 7 at home, it’s the usual story during winter 🙂

Head to the show notes to get all links and resources we mentioned, along with a full transcription of this episode at joshhall.co/421

Intro

Welcome to the Web Design Business Podcast with your host, Josh Holland, helping you build a web design business that gives you freedom and a lifestyle you love.

Andy’s Cold Email That Changed Everything

In‑Person Setup And Content Repurposing

Josh Hall

Hello, my friend. Welcome to a very special edition episode of the Web Design Business Podcast. This one's special for a few reasons. Number one, as you could probably tell by the thumbnail of this, this one's in-person. And this just made me realize how much I love in-person interviews. I've very rarely done in-person. Um but the dynamic is different. The conversation is different. There's no barrier of technology like buffering with Wi-Fi issues or anything like that. So I'm definitely going to look at doing some more in-person interviews with my local contacts and colleagues here in Columbus, Ohio. So if you like this, please do let me know wherever you're watching this or hearing this on your podcast feeds. I'd love to hear from you. Um, the second reason this is special is this interview is with Andy Milligan, who is a web designer pro member and a young, up-and-coming whipper snapper web designer and design strategist who's made incredible progress in just a couple years. So much so that he had his best year to date in 2025 crossing over the $200,000 revenue mark. However, very fast growth comes with very fast growth pains. And it was actually, as you'll hear, quite there's a lot of stress in here that Andy had to get through despite having a successful year. So we're gonna get into that in a lot of this one as well. This interview is kind of half about um some of what I'm up to and what I've learned as a community builder and coach, but also digging into Andy and kind of a coaching episode as well. So this is kind of like two episodes in one on this one. And the third reason I I want to mention why this is so special is that Andy I've just seen him make such a fast trajectory um in his journey. And this is for his podcast. So this interview is actually recorded for his show, which is Marketing by Design. That will be linked in the show notes of this episode. This one's gonna be at joshhall.co slash 421. And he's just become a really great interviewer and he asks some really good questions. We get into some stuff that I've never talked about on the podcast before. So I just want to give kudos to Andy. Um, just so excited to see what he's up to, how far he's come already. Uh, and it was really an honor to, you know, to be a part of his journey so early on, and then to coach him at this level. And I'm so excited to continue to coach him as he goes to the next level. Now, before we dive in, Andy referenced his very first email to me. Um, he didn't have it there live, so we didn't read it live, but I found it and I want to share it with you because I think it's gonna set the context here before this conversation. So if you're watching this on YouTube, here it is. Um, but I want to read you this email because this was a cold pitch email to me. Uh and then that's what kind of started our relationship. That's I ended up coming on his podcast initially. We'll have that linked as well. And then he joined my community web designer pro shortly after this. So he said, and granted, again, this is coming from a kid who just turned 22 at that point and is new to the industry, but I wanted to share this because cold outreach can work if you're genuine. And Andy definitely was. So here's his email, and then we'll dive in. Josh, I'm Andy, I'm a super big fan of yours. I know you're a busy dude. This will only take a minute to read. I'm actually not that busy by design, but I appreciate that. I reason I recently moved to Marysville, Ohio. I'm in Columbus, Ohio, so just about an hour away. Not even an hour. Um, after graduating to start work at a graphic design job, I just turned 22. After moving into a department and doing nothing but work for 40 plus hours a week, I'm trying to build my side business in the evenings. I'm admittedly a little lost. I want more than anything to be able to build a livable income without working a day job. How timely and ironic that with just a few years later, not even a few years later, he's already passing 200K in revenue. So it can work. It can happen fast. This competitive job has taught me that I value my time and freedom more than I realized, but it's also got me spinning my wheels and burning the candle at both ends. Let's get one thing straight. I'm the hardest worker worker you'll ever ever meet. Unless, of course, you happen to be friends with an actual psychopath, of which I am not. Again, AI is not going to give you that likely. Uh so I could tell this was real. I think a mentor, here's a spelling issue. There's two eyes instead of one, also tells me like I'm fine with some grammatical issues because I do them, and AI will clean that up. So that tells me like this is from a real person and not just an AI-generated cold pitch. I really think a mentor would help me define my target audience and offering and help me make meaningful connections. I've tried a lot and have gained a lot of traction, but not enough to be financially self-dependent. I spend my weekends doing cold calls and sending inquiries to local businesses who I think who have design needs social media, video editing, web, etc. I average about three to four projects a month. Just started a podcast where I talk to successful people in the industry and try to learn and get career advice from them. And I've got a small audience of creatives and graphic designers. This is such a great cold pitch email. Tells me about where Andy is, what his goals are, what his current setup is. And now that I know he has a show, I actually invited myself on his podcast after this. Um it gives me some context and gives me something I could repurpose eventually. I've seen your web designer pro offering. My only reservation is how much uh of it applies to someone with a skill set that is not 100% web design. I don't know a ton of code, but I'm really good with Webflow and can do custom sites for clients. Um, two of those have been my biggest projects to date. I know you're starting in more traditional web design, which is why I get a lot of value from your videos. I know that was a lot, and I want to make it to a point um not to not make an ask without providing value in intern. So I would offer to be an affiliate of yours for free on my podcast, or if it benefits you to serve as a case study or testimonial for your content. They've helped me greatly and potentially become a student, depending on your answer to this question, if it's applicable to his skill set. Just want to say thanks, regardless of whether you see this or not, Josh. More than anything, I want to be successful. I hope this gets across to you. What a great cold pitch email. I wanted to share that because again, it highlights how to do a cold pitch email that is genuine. And again, um, there's imperfections in there, which is great. It says it shows that it's not an AI template or or AI slot. And there I got to know Andy, I knew his age, I knew where he's at in his career, I could tell that he was the real deal. I could tell by just sending this he's he's a he's an eagle, he's someone who's gonna get shit done. And he let me he asked some questions about Pro. Again, I actually um after this, he became a member of Pro just because I let him know web design would be perfect fit for him. And as you'll hear, a large part of his $200,000 plus year in 2025 was because of web design. So all roads lead to web design. Yeah, yeah. And then he also let me know that he has a show and that he'd be interested in having me as an affiliate on the podcast. I think I misread that and invited myself onto the podcast. I think that's how that happened. So, anywho, here is our interview in person together. Yeah, yeah, yeah. Two years later. Actually, just over two years later from this. This what he sent me this in the fall of 2023. So we recorded this just over two years after this. Uh, and he's just a shining example of how fast you can go in this industry, but it can come at a cost if you're not careful. So we're gonna dive into the stress of success and a lot of other good stuff in this interview. So cheers to Andy. All the show all the show links that we mentioned are gonna be at the show notes Josh Hall.co slash 421 in this one link below. Side note, real quick, I was getting over like the worst sickness when we recorded this. So I am you'll hear I am not sounding my best at this point. So just a heads up, apologies for the coughs that you're about to hear. But here is my in-person chat with Andy.

Andy Milligan

Whatever. I usually I don't like having like the lights camera action sort of starting the podcast.

Josh Hall

So thanks, I appreciate it. Yeah. Thanks, Morgan. Appreciate it. Can I repurpose this for my show? Absolutely.

Andy Milligan

It'd be cool to have a uh uh you know profess like legit studio version of a um my um uh recent started on EA two months ago. She can go into Riverside, use Riverside. Oh, well, yeah. I can send you the um the studio link to Riverside so you can download it and use it however you want. And uh and also how does this so how how does the recording on this go? So this is recording to the the roadcaster, um, and literally right afterwards after you hit it. The auto switching is already working right now. Um and then it but it resaves locally, and then there's one click away, it stores on an SSD. Okay. And then I just plug it in, put it to Google Drive, I can save the switch. Upload it to Riverside.

Josh Hall

That's literally instantly. Yeah, it's awesome.

Andy Milligan

Yeah, it's crazy. It's way too nice for me.

Josh Hall

I could definitely see eventually doing some more in-person stuff like this.

Becoming An Authority And Beating Imposter Syndrome

Andy Milligan

Yeah. It's a real well, I'm using it more for I mean, client acquisition tool, like for referral partners. Yeah. One of the and I when I first started the show, I was like, um I wasn't far enough along in my journey to be like helpful to people that, you know, were ahead of me. Um so I was I mean, uh there's a I mean, there's a value to that because they genuinely appreciate like the enamorment that I had. Like when I first talked to you, I was just like, dude, like I love you.

Josh Hall

Um well, but it was more like there's a difference between experimental type of shows, like you're learning like you're learning with somebody versus like I have all the answers, or or you come across like an expert. So this is what's kind of cool about your show is to see it go from I'm learning to like, oh, I have a lot of expertise on some stuff now.

Andy Milligan

I still don't you never feel that way. It's just imposter syndrome is constant. Um did you probably never did, but did you ever reach the point where you felt like you could be more like the authoritative leader? Was it like after you started making courses where you felt more like you had like you were the teacher rather than the student?

Josh Hall

Aaron Powell When I started Josh Hall.co and teaching, I I felt that pretty early on just because I had been a web designer to that point for you know seven, eight years at that point. So I had a lot to share. And blogging for elegant themes was a huge help with that because I was like, yeah, I'll share what I'm doing. And then I got so much notoriety in that community at first. So yeah, I'd say like I didn't really have too many of the or I didn't have too much of the imposter syndrome as much just because I had done it for so long. Yeah. And I've always been a like, I I know from the get-go there's a lot of different ways to do something. So here's the way I do it. I know there's different and probably better ways to do it. But so I had that mindset early on.

Andy Milligan

If I've learned anything, it's uh a lot of times entrepreneurs are can be some of the most insecure people. Um, and not always in a bad way. I think it's um, and this might not be your case at all, but I think a lot of times they drive, they push themselves harder to almost prove things to themselves rather than um trying to reach like abstract goals. Like that was my um, I was one of the most like insecure kids ever growing up. Like I had, I mean, since I was age three, I had like these big tie-dye hearing aids. So I was always trying to like impress like girls and stuff like that, and just I had a really bad wisp and everything. Um my parents were always like very supportive and everything, but I almost felt like and this is we all put ourselves in a state where we're disadvantaged, and I had you know, it's like golden handcuffs, but I always felt like I had to prove it to myself in order to make it real. Um and whether you have to find, especially when we were all the stakes aren't high unless we put them on ourselves sometimes. Um, I think wherever you can get that inspiration, and especially like when I first got into pro, when I first started the community, um I had just gone through a layoff, and you probably remember something like that. I literally, the day of the layoff very viscerally, um, I literally got on one of the the weekly coaching calls. I was like, okay, so that was one of my things. I remember so green back then. Yeah. Um but yeah, that's I mean, it's a big part of my story. Like you're literally the person that got me started in web. Like, um let's cheers to that, dude. Let's coffee cheers to that, man. You on water cheers? Cheers to that.

unknown

Okay.

Josh Hall

Yeah, dude. Um we'll pretend it's Irish coffees, but it's actually just regular coffee. So Yeah, I haven't had straight black in a while. I usually do like stevia. Yeah. It's a little better. Um, I'm pumped for you, Andy. It's freaking awesome, dude. Um I mean, last year, 25 was huge for you.

Andy Milligan

Like huge for you. Well, I mean, you probably can gather, and I think you've seen I see you as someone who's kind of seen people get started and web. Like you have, I mean, the community you've seen hundreds of people that are at different phases of business. Um, and you've seen people that stay with it, you see people that have had spiky success and you know, maybe flash in the pans and things like that. Um, what do you see in the people that you know they have, I mean, I feel like every modicum of success I've managed to happen that I've managed to make happen is just by like forcing it, you know. Like I feel like I'm always like taking one step forward and two step back, and I feel like it's I know it's not, it's just kind of a lot of it's probably my own personal head trash is that I've it feels way too hard. Um but what do you see in the people that get started uh either freelancing or doing some kind of thing on their own and then stick with it and and manage to build on whatever they've managed to accomplish?

Josh Hall

There is there is something. And I'm I've really been thinking about this more and more because you, other web designer pro members, Alexia, Ben, um Sam, obviously. Like there I it's funny because I think about all you guys as far as you being very new to the industry and very green. But I could tell it's funny, almost instantly, I can tell if somebody's gonna stick with it or do something. And I really have thought more about what is that? What is the intangible, like this person's got something, they're gonna they're gonna stick with it. And I don't know. I really don't know yet. Maybe by the next interview I'll have a more clear answer, but I don't know what that is because like in your case, you sent a great cold pitch email, and I was trying to I don't know. I know you have it. Are you gonna read that? I can't find it. I'm gonna find it. I'll have to go off camera.

Andy Milligan

Didn't I say did I post it on LinkedIn? Or I forget. Um Yeah. We we talked about it on LinkedIn and I appended a screenshot to it.

Josh Hall

So I have it somewhere. The reason I mentioned that is I'm trying to think back to that. Like what was said that I was like, okay, this you know, this kid's the real deal. Trevor Burrus, Jr.

Andy Milligan

It was probably it was probably like who the hell is this kid? And then it eventually changed.

The Intangible Trait Of Entrepreneurs Who Stick

Josh Hall

Well, but but what's interesting is that doesn't happen much. So like for someone to reach out in the first place, that that's not like a templatized, cold, like I've I'm a huge fan of your show. Your recent episode, da-da-da-really caught my attention. Like those are red flags to like, oh, this is just a cold, you know, templatized DM. And sometimes I get the exact same template from cold outreach. So if it is a true, like unique, authentic DM that isn't spelled perfectly or has some weird grammatical things that's based off of your personality, I think it's great. Yeah. Um, so like that's if if I ever do more of a cold style outreach, I'll put like hot dog or boy howdy or one of my you know, goofy dad sayings in there, and it really does stand out. But to that point, man, I I really there is something. There is a, I don't know if it's a I don't know if it's a confidence I see or a per maybe it's persistence. There's something there, though, to the people like you, Sam, Alexia, so many members in pro who are earlier on, and then I see like, oh, this person's gonna stick with it. Or at the very least, they're gonna, they're not gonna quit or they're gonna do something freaking awesome.

Andy Milligan

Right there. I think that's part of it. It's just the um the acknowledgement that like almost in your head, there's no other scenario. Like it's either it works or you're gonna stick with it either way. I think a lot of people um who maybe don't reach the success that they want, maybe view it as there's a fallback to them. And I think we all have fallbacks, but if you can get yourself mentally to a point to where you know you're just really set on making it work one way or another, and you almost, you know, jump off the cliff in a good way.

Josh Hall

Um that's I mean You have to really do it because if you have a plan B that will eat into your drive, that'll eat into your strategy, and it just creates like um I was gonna say fear mindset, famine mindset. It does. It's really, really risky to have a plan B because inevitably it's gonna take mental bandwidth and you're gonna think about it. And if any market shifts happen, you're gonna really probably really quickly go back to plan B. So I mean, I remember like when I first started, my mom, bless her heart, was like, what are you gonna do if one people one day websites aren't there? Like, what are you gonna do? Yeah. And she's like, What's your plan B? And I'm like, I don't have a this is it. Like and I've realized obviously now I can confidently say like I am an entrepreneur. So even if it wasn't a web designer pro, I would do something and I would love it. You know, like it when you are an entrepreneur, you can almost go to like any passion industry that you're gonna you're gonna kill it, especially if you learn like the intangibles of just good sales principles, good marketing principles, good communication, being a cool person, like the all those intangible things that you could go to any different industry or creative endeavor.

Andy Milligan

That's so good. Yeah, I was just listening to James Queer. Um I don't know if it was Jay's episode with him um or um or another one, because he's doing a lot more content these days. I think he's coming out with another book. Um, is he really? Yeah. But he literally said that same thing. He's like, I always identify, which is crazy for me to hear. But um, he literally said, I I identify as an entrepreneur. Like the author stuff is secondary, but I've always approached it with the mindset of how can I make this entrepreneurially productive? He looks at everything as a business. And I think what even like one of my own not downfalls, but maybe something that I'm conscious about changing is how can I adopt that lens more to everything I do rather than I think a lot of people, especially in creative freelancing niches, are just like, how can I take this thing that I like to do and then justify it as a um as an income stream, you know, or how can I spend my life doing the creative part of what I love? Um I think there's there's a value to that, and it's not for everybody, but I really that entrepreneurial mindset is like I can absolutely make anything successful um if I just take the learning mindset to it because it's universally applicable. Yeah. One thing I wanted to pick on, kind of double click on what you said, is like these kind of um intangible and intangible skills. You mentioned like communication, networking, sales. Um, if you had to pick one that maybe has been the biggest contributor to your success, where maybe if you could go back in time, you would maybe focus in on it more, like honing that. Um if you had to pin it to one, what would it be?

Josh Hall

Communication over everything. Okay. Absolutely over everything. I went to a I didn't know it was gonna be like a network marketing seminar uh that my friend invited me to. I just thought it was like a business meetup. I didn't know it was gonna be like a you know pyramid scheme, like they were trying to get you to invest. But yeah, I'm glad I went because it was actually really good from a like a professional development sense. And the speaker that day said something that has stuck with me. This was probably 2011 or 2012. And he said the quality of life will dep your quality of life will depend on how well you communicate. Yeah. And that is true in every uh aspect of life: relationships, marriage for sure, um everything. You're how you come across in your business, messaging, website, how you talk to your team, how you talk to your clients, how you handle support and how you handle adversity, all those things, how you have colleagues and networks. So it's the through line of I think most successes, some level of communication. Yeah. Especially if you are somebody who is the face of the business in sales or doing interviews or yeah, like leading a team. So communication, bar none. Yeah.

Andy Milligan

Part of it's like um, you know, Dale Dale Carnegie, How to Win Friends Influence People. I was lucky to read that book really earlier. I think part of it's like how how you make people feel at the end of the day. You know? Yeah, yeah. Like that's such an overlooked skill that it's it's hard to practice. But um, I think you have a leaf on your watch, by the way.

Josh Hall

Or is that a lot of things?

Andy Milligan

This is actually my sister gave this to me before I left for college, and it's worn off now, but it's the coordinates of the college that I moved away to in North Carolina and home. Um speaking of how how you make people feel, I feel bad that I said that much. No, it was a leaf for a second. I know it's too it's too big. But um yeah, it does come up like a leaf. It just like flashed real quick. I was like, I think is that a leaf? Um how you derail interviews, that's what I've learned, really keeps people grounded. No, you're good, man.

Josh Hall

But yeah, communication, truly, truly. Like it really, I mean, it's just so much. It's just the through line through everything. Yeah. And I think back to all of my endeavors and getting better at that, what you said, how you make people feel. I mean, I've talked about this a lot, but when I started in design and graphic design, I was not good at design or graphic. Um but I made potential clients feel good because I actually cared. And I was like, I'm really gonna work hard at this. And I made them I learned early on like in sales calls and sales meetings to give people like a vision or get them pumped up. And I do think I've have a natural um, this sounds super douchey, but I'm I I can easily create inspiration for folks. Yeah. Um with like what's possible. Yeah, like see the future of the yeah. Yeah, like create a little bit of a vision, or even just if it's a short road ahead. So when it came to like getting clients early on, the communication part for me was like genuine care and genuine excitement and giving a little bit of like inspiration. Yeah. And that's what that's how I sold my first few projects.

Plan B Kills Focus

Andy Milligan

I'm an I've been on there seeing the end of that. That was I could literally go back um to the agency. I was literally just working illustrator, making proof templates for um wrestling singlets, and just the backlog of web design and reading hearing some of the case studies, you know, learning how I could like that was the first shit for me is like I could make money doing this thing, you know? And from there, you know, the entrepreneurial bug really took off. Um and then obviously, like um nobody should nobody should get started with no clients, um, make that your full-time income. But I mean, even I just talked to Sam last week, and I think there's something there to literally just kind of talked about it, like forcing no alternatives.

Josh Hall

You and you and Sam both went for it. For those who don't know, Sam. Well, I was laid off. So you were laid off. Sam actually like jumped off the cliff. But but yeah, I mean, you could have got you could have like put the the podcast aside and the agency aside and like got a job and done something different. But you had already built up a little bit of momentum to to where like losing that nine to five wasn't almost especially because you didn't have a you know a family yet. You the the responsibilities and the amount of bills that you had are at a point where like it was less risky essentially for you to just go for it. So in those situations by all means. But there is something to like, I'm doing this. I'm jumping off a cliff, I'm and obviously any in any of those situations there needs to be like a ground of reality to where it's gonna be. Like there are some situations where I'm like, oh, I don't know if I would do that. But uh Ben, I remember Web Designer Pro, he's got four kids and just left his job last year and he's killing it. He's he's he's not where he wants to be yet, but he's he's to the point where like he the foundation for his business, he could blow that thing up. Um so I just think about that a lot, about both of those situations, that intangible, I still can't put a finger on what that is. Um, when you meet somebody who's got it, who's just they're gonna do it, they're gonna kill it. Uh and I can tell that. Like sometimes in the first sentence or two of an email, I can tell like, okay, this person is the real deal. Yeah versus and then there there's the actual action because there's like talking about it and sensing like, okay, I think you've got whatever it is to last. And then there's the like actual actions to like, yeah, I like, you know, I left or you know, I got laid off and I'm going for it, or I'm leaving my job to go for it. So there's there's a couple aspects to that. Yeah. For the earlier entrepreneurs where like those are clear signs.

Andy Milligan

Yeah. I think you kind of have to step into it before you're ready, as with a lot of things. Um, identity, and this is another James queerism, but like I identity is such a big thing to inform like your actions during the day, you know, like because if you don't see yourself as a person who is the thing, and sometimes you have to have that stark reality of like, okay, like wow, I'm doing this full time uh to like really make you feel like that's who you are. Like now I am you know entrepreneur, I am a web designer. Um, I wanted to paint a kind of a scenario for you. Um, so you've seen a lot of entrepreneurs come through pro. You've obviously met a lot of people who are probably in the beginning stages of building a business for themselves, you know, making a business out of web design and their creativity. Um picture a couple years down the line. Um, how how old are your kids right now? Seven, six, and three. Okay. So picture like a decade, decade and a half down the line. That's just I know it's a long time. Don't do that to me, Andy. But I know. Don't make me get teary on this podcast. No, that's not the goal. Um I'm sorry. Like a decade and a half down the line. Um your kids are to the point where maybe you're thinking about college, um, they're starting to be big boys and girls. Um what would you say to them if they they come up to you and they say, I want to be a web designer, I want to be independent. Um if you could put yourself in that situation, would is that something you would recommend that they do, or what would the emotions be around that?

Parenting, College, And Entrepreneurial Paths

Josh Hall

For sure. For sure. I would so encourage. I mean, what's interesting about like, so Emily, my wife and I, our parenting style is we're very, we're pretty kick-ass parents, I have to admit. Like, we're super cool. Like we're we are not the people who are like, okay, you need to go to college and you need this path, and you need this, and this, and this. We're what's interesting about our dynamic as parents, and this will answer the question, is I am not an academic. I have a lot of um vitriol towards academia in a lot of ways. Um, not for mainly for entrepreneurs, not for you know, if you want to be a firefighter, you want to be a a doctor, yeah, go, you know, like do the do the proper education. But as an entrepreneur, um even when it when it gets to that point, I'm gonna be very much like probably an alternative path encouragement. Um in you know, being that I come from a world where I mean, I felt terrified to grow up when I was out of high school because I just did not want to go to college. I did not want to sit in a nine to five cubicle situation. I was not terribly smart. I was like a solid C student, so I had a really hard time through high school. And it was mainly because it's not because I'm not smart, it's because I'm I just didn't care. Yeah. I really just couldn't give a shit about most of the subjects I was learning about. And just like many entrepreneurs I've found out, we excel when we have something we're interested in. So to answer that question, I think once it gets to that point, we'll really try to do a good job of empowering the kids on what they're interested in. Now, my daughter Annie wants to be a doctor, by all means. Yeah. You know, you could traditional path might be great for you. Go for it. Um, even if there's like business or marketing, you know, maybe that's the case. But I'm definitely at that point going to encourage like find interests in lanes. And and interest doesn't, they don't need to be in a category. So in the case of like me being interested in web design, that wasn't really a thing outside of high school. Yeah. I mean, we're I graduated in 2005, so there really weren't many like web designer paths. There were, there was a little bit of web design back then, but it wasn't like it is today. So if I had said I'm interested in being a web designer, it would have looked a lot different. But I was interested in again, like the through line type of things. I was interested in sales and marketing to a degree, entrepreneurship for sure. Um funny enough, what I do now is a testament to my upbringing, which is I've always been a community builder. Yeah. Even in high school, I had friend groups that I enjoyed, like, oh, you should meet this person. They you guys would hit it off. Uh looking back, I'm like, gosh, I've been a community builder since I could remember. Um and even after high school, when I got into my band, um, I helped facilitate a lot of the folks around the band to you know to be our core group. So all that to say, I'm definitely gonna be really interested in helping them find the the things they're interested in. And it doesn't need to be a job or an industry because as you know, like if you're good at communication and you're entrepreneurial and you're driven and you like design and you like all these things that could actually work in a lot of different industries. Long-winded answer to say it's not about an industry or a category of success. It's like yeah, the professional personal development that I think are the most things to dive into. So yes, I would encourage entrepreneurship.

Andy Milligan

I such a good answer. I I think just growing up with my parents who were your parents entrepreneurial in a sense, really. I am the most I'm the blackest sheep in my family. Yeah, cheers to that, yeah. I dude. I my mother was a uh librarian uh and a school teacher. Father is a uh police chief for 35 years. Okay. So I mean, two very like very service-oriented jobs, but very much go work for the man, you know. Um I told this to another one of my mentors um a while back, but I started last year with the I said like come hell or high water is kind of like those same emotions of you know, going to the deep end with um with the business was I want to make six figures in my first full year. Um, and you were one of the seeds that planted that. I kind of always viewed that as a North Star metric. Um and going back to my own childhood, my father, um, when I was probably like eight or nine years old, he had a cookout, um, invited like all of our family members over, kind of a small intimate thing, but close friends, family, grandparents, things like that. And um we had like hot dogs, pizza. And I didn't really know why we had just kind of a special gathering and why we had it. But essentially it was um a little past 20 years into his career. He was a lieutenant, almost a almost a chief at that time. And he said, He's like, Andy, do you know why we had this tonight? I was like, No, uh, I probably didn't care. I was like eating hot dogs and stuff like that. But um, he told me he's like, This is this is the first year I made six figures. Um and that like an impressionable point at that time, and I was like, well, first I was like, Well, what does six figures mean? He's like, Oh, it's a hundred thousand dollars. Um and I always viewed that as like, okay, it took dad you know 20 years to get to that point. Um, and in our first conversation, um back like really early days of the show, um, you that was one of the questions I asked. I was like, Do you see a way that people can make six figures? Because I was just always like success, success, that was what it was for me. Um, and you're the first person that kind of made that tangible for me because I always view that as like this is what success looks like. Um wow. Did you ever have a moment where because I think entrepreneurship part of it, and I'm definitely learning as I go as I go here, um, but you just reset your expectations so much of like okay, I want this goal, what's the next thing? And you almost get to, and this is maybe recency bias for me, but you almost get numb to like what the next thing is. Um you like it's it's so hard to see like the past version of yourself and um how you know how proud they would be of where you are now. It's so hard to see that contrast in the moment. But have you ever had a moment to where first of all, what's your like um what's your mindset around setting goals, either entrepreneurially or with the community or anything you're currently building? Do you think that's a positive or negative thing?

Resetting Goals And Identity Shifts

Josh Hall

I do. I think it's a positive. What's interesting right now is I'm kind of in a bit of a new the beginning of a new identity around like what's possible. Um I'll say this now, I don't know when this is gonna come out, but I'm actually like about to launch my first official mastermind, which is gonna be a very high-ticket option, which I've never done before. Okay. Um so I a lot of it is I I feel like you mentioned identity earlier. When it comes to like your expectations and goals, I think the bigger thing is actually like your reality changes once you get to certain points in the journey. Like your reality just a couple years ago was probably when you thought about six figures, it was probably daunting, felt in the distance, felt like it's gonna take 20 years just because of the reality of you know your upbringing, your situation. But didn't you do 200 plus last year? Uh you've done double six figures, now you're in multi-six figures just two years later, and your reality looks way different. So I think that's a lot of it is when it comes to goal setting and what's possible and vision. It changed like I think it's good to take baby steps, honestly. But you do get to points where it's like, okay, this is absolutely possible. And then you start to know other people and make connections with people who are doing this, and they challenge you and they affect your mindset in a really good way when you're working with you know people on Web Design Pro or other entrepreneurs you know, and they're like, well, they have no problem charging this. Why is that so weird to me? Um and I've certainly experienced that and continue to experience that. Um because I come from a very humble background to where basically for a good 10 years, I pretty much set goals to where like, here's what I want to take home. Let me just try to make a little bit more than that to be able to cover taxes, expenses, a little bit of profit. Um, but now I'm like in the place I mean it's funny, so this is so timely. I was just talking to Sam yesterday about this. I'm like, I'm at a place where I freaking made two and a half million dollars being an entrepreneur since 2009 or 10 when I started my business. Since then, I made two and a half million dollars. And I don't feel like my pricing right now reflects my value. And that you I think everyone gets to that point where whether it's charging for a website or a branding package or a service or a consulting. So I'm at that place right now. I know all my students are probably like, oh God, what are the rates gonna go up to? Um, but everyone is in pro right now is locked into their rates. So but I am absolutely to the point where I'm like, yeah, I need to like do a better job at charging the value that I that I have learned and that I also create for the people. I mean, there's people in pro who are doing 200, 300, 400,000, 500,000 plus. And I look at yeah, like my pricing options, and as I'm thinking about setting goals, it's a little more now moving towards my value as an entrepreneur and what I've learned and what I see working. So actually, Chris Doe I had on the podcast last year, and he gave me a really good framework. Did you listen to that chat? Yeah, I did. So, in short, what he mentioned about goal setting was that there's two ways to create a goal, which my first way was you know what you want to take home, you try to make a little bit more than that. Yeah. Um, but the next way is like still grounded in reality, but what's like a dream goal? What would be like the life-changing number that would really take you to a whole nother level? And obviously it's gonna change your pricing and your offers. So I'm a little more leaning towards that. Um, but there's also market like realistic market things when it comes to pricing and offers. Um, if somebody has astronomical rates but it's not has not proved themselves in the market, then that's probably not gonna work out too. So there's like a healthy balance, I think, with like knowing what rates are. So for me, I would look at like business slash design coaches and web design and and digital marketing agencies. And um yeah, that's that's the hard part, I think, with that. When a goal setting is like you don't want to price yourself too low, especially when you're starting out. But if you're just starting out and you're super, super high, the question would be yeah, like I 100%.

Andy Milligan

Understand. I think um well, I've very recently been the victim of this is I think that when you you have to be careful of like what the um the the goal can inform the actions that lead to it, right? And I said that really uneloquently. But essentially, if you set if you set like an abstract goal, you will sacrifice everything if you make that like your North Star. Um like uh the example, like coming from a revenue goal, that can be a I mean, this wasn't my case, but revenue and what a couple of the agency owners that I've gotten to interview, revenue doesn't equal profit. So you can set a revenue goal and you throw the kitchen sink at trying to reach that at all costs, and then at the end of the day, you're doing worse than the freelancer who's you know 90 plus percent profitable, obviously with taxes and everything, you set that aside. But when you make you have to be really diligent on rather the inputs, I feel like more so than an abstract, you know, financial number at the end. It's like now I'm now more than ever I'm focused on like am I enjoying what I'm doing during the day? You know, like today I could look back and say, okay, got to work out this morning, got to reconnect with Josh, you know, I got to Best Day of 2026, I'm sure. Already and I have you know two or three more calls today with people that I'm actually excited to meet. Um that to me sounds a hell of a lot better, even if you know 26's revenue is 150, 200, you know. Um it sounds really sexy and cool to say I'd love to make a quarter million in my second year, which I now I know I've proven to myself that I can scale and just fix my lack of experience by throwing my time and energy at things. I think there's a certain value to knowing that you have that in you. But dude, like I just I just want to enjoy my life.

Josh Hall

Yeah, good for you, dude. I mean, so I want to unpack a few things you said there, because that was all wise. That was really for somebody early on in the journey like you, that's usually something people come to later on when they're you know missing their kids growing up because they're working so much. Yeah because you're right. I I love a revenue goal just like anyone, and I actually still recommend a lot of my pros do that. I have a revenue calculator where I help them like, let's map out what do you want to make this year, what do your services look like. But that's primarily it's it's primarily the the North Star about helping people with pricing and offers. What is not seen in there is the hours worked. So you're right, like there there really are like a couple categories of goal. There, there's the revenue, there's top line revenue, there's profit, huge, and then there's time. Like with those goals, like when I when I think about a bigger number, this is probably actually as I'm thinking about it, the thing that has kept me from thinking seven figures, because we did four over 400 last year, which is great. Best year to date for my little business with a super modest team, and profit is freaking awesome. Like it's it's awesome. Like I have nothing else on the books today. It's I've created a real nice balance of lifestyle freedom. So like last year was great, and then I kind of felt like, ah, I wish I would have hit 500. But I'm like, you know what? It was a busy year, as we talked about. I don't know if we were recording yet, but like my daughter had a lot, a couple major surgeries last year, a few additional hospital stays. It was a busier year on the family front. Yeah. And I was able to not sacrifice being present for any of that because I wasn't chasing an arbitrary revenue goal that was, like you said, gonna pull me away from family time or or just feeling stressed out or burned out or hiring and not needing to hire. Like if I didn't so you're totally right. Like you can set all these wild goals, but you need to make sure if it is a a big goal, it's not gonna sacrifice you enjoying your yourself. Which I was gonna ask you, based off of your 200 plus year, like are you in are you having fun? Or do you feel like you've do you feel like that tells me like you've probably crossed over to like having a little too much the unfine things?

Revenue vs Profit vs Time

Andy Milligan

Yeah, it's a good well, I mean, it kind of goes back to what we talked about in the beginning, is like I'm not gonna quit, you know. And this is I've told this story on the show before, is like my again, my father, um he's he literally had the conversation with me growing up, and this has been productive. It's the source of like one of my most positive traits and also one of my most toxic, says you're a milligan, milligans don't quit. And I will take that to the logical extreme in anything that I'm doing. Um, it's productive in some sense with entrepreneurship, I think 100% podcasts, you know, weekly for 135 weeks now. Um it's also the led me to like some of my lowest points, like burnout or I think I I mean I use the word burnout loosely, but it's almost just like numbness. It's kind of like what I was talking about earlier. It's like you see a goal, you know, you have like beforehand, it would have been like a really cool um progress marker of like getting to interview someone super cool. It's like, oh yeah, you're just worried about the next thing. Um you reach the revenue, or it's like, oh yeah, you know, what's the next thing? It doesn't feel like a win, you know, it just kind of feels like not.

Josh Hall

I got that sense when I I listened to your recap for 2025. And I did feel a little, I'm gonna be completely honest with you, I felt a little like it sounded like somebody who had a stressful year. Like, you know, like um, you know, like if I would have hit 200k after a couple of years, I'd have been freaking there would have been some celebration going on for sure. So, like the the quit thing, as much as that is a great thing to have as an upbringing, I think people put quit in the same bucket as pause or rest or pivot or step back. Like all of those things feel like quitting when they're not, they're very different. Quitting something, and and honestly, like I'm not saying you're gonna quit your agency, but you could quit the agency, but that doesn't mean that you quit you know, Andy's journey as an entrepreneur. Like your bigger thing is being Andy the entrepreneur. I will not be surprised if your agency looks very different in two years, whatever that looks like, whether it's scaled or whether it's scaled back. But for you, like quitting the same for me. Like, I guess I could say I quit my agency when I sold it in 2020. But for me, I just changed part of I didn't quit my journey as an entrepreneur. Now, if I were to quit and you know, do landscaping, yes, that would be like or like tour bus uh customizing. Yeah, tour bus customizing, then yeah, that would be uh but even like yeah, like I I don't know.

unknown

Yeah.

Josh Hall

You know what I mean? Like there's just those terms need to be very, very um carefully segmented and separated. Rest, pause, it's not quitting.

Andy Milligan

Yes, I see and this is it's able to recognize things it's like hindsight's twenty twenty, but with so many Freelancers, creative entrepreneurs, they are they they can't detach from the them and their business are the same thing. So they can't think. I think you, Jay, other people um that were in Jay's um you know mastermind is the idea to be able to attach and just look at things more so from a business sense and view what's productive. So like I look at your story, you started as you know, employee, employee, then you started on your own. That you viewed as a business. And then the logical next step, using the momentum that you had gained, was then coaching other people to achieve the results that you had, um, sold the agency as a business asset, uh, liquidated it to someone that you had coached. And then even from that, the next step from the um courses was the community model to where you're helping those people on a more intimate basis, add more value to them. Um, it just seems like you're able to take what you have to work with and apply a business mindset to that and then be able to see the next step. I feel like a lot of people get stuck in the first phase of the fulfillment. There's so many emotions when attached to what you do rather than just looking at this, okay. That's what the biggest thing, like the monthly retros have helped with, is just like this is a business. This is not just Andy working on his laptop, you know. And you're able to see profit, loss, and just it's an objective viewpoint. Then it's it helps so much.

Josh Hall

Well, what you're hitting on too when it comes to like doing new things and maybe changing your role in a business or changing the business altogether or selling a business, what at the core of all that is your identity. And to your point, like it's really, really dangerous territory to attach an identity to yourself as an entrepreneur if it's based off of a thing. So for example, when I started being an entrepreneur, I started as a designer. So I was a gr I was a graphic designer first. You know, you're like you're you're like the Josh from you know, you're like 15 years behind me or whatever. Um and then my next identity was a web designer. And then my next identity was a web business owner, and then my next identity was a course creator, and then my next identity was a founder, and then my next identity was a community builder, and then my next identity was a coach. And in there are like micro identities as a podcaster, a YouTuber, uh a mentor in different capacities. So I at this point, 16 years into this, I have been very self-aware and have realized that identities are they're gonna change. And I think people on the outside, this is really, really hard to understand because most people who aren't an entrepreneur get a job and they're generally in a job or at least the same industry for quite a while. So I think the difficulty for them is we have we're very multi-interested and multi-passionate and multifaceted to where like we can identity shift, and it's not that big of a deal for us after a while, once we get used to it. But you know, somebody from years ago, they're like, Aren't you still doing this, or you're still a you know, a web designer or whatever? And we're okay with being like, oh no, I'm doing this now. And they may think, like, oh, maybe you quit, or maybe it failed. It's like, no, we just moved on from that identity. And there's no set of length for a career or a job or even your own business that is right or wrong. Like, I think in a lot of ways I would have been happy as a web designer and business owner for a long time. But I also, going back to what I said earlier, have an innate community builder, it just comes out of me. I just can't help myself. I could go out there and meet a bunch of people in Kohatch and you know, probably organize like a little team together. It's so you know, with that by the end of the day, like I just I just love it. I just it's effortless. It's but that would be really hard for some people who are not wired like that. Yeah. So that's a part of it too, is just really being okay with identity changes. And it's hard because the re like like we just talked about, your reality changes when your identity changes. Um the through line is communication and just good sales, marketing, being a great person, those things. But um the identity is a hard thing to look past. Because what comes with identity is your work, you feel like your value, pricing sometimes, your offers, and then your mindset can sometimes become an identity. As a web designer, you know this. Like there are, I mean, there's mind trash in every industry, but web designers in particular, at least mostly in WordPress, um, you can go down a very cynical, dark developer type path. Yeah. Um, where some of the most successful web designers I know didn't come from the developer side of things. They come from like a business perspective, and web websites are the main tool in a bigger package. So it's like it's interesting to see how different identities and different mindsets can completely change how an industry is like like web design.

Numbness, Burnout, And Finding Joy

Andy Milligan

Yeah, it's so good. I mean, so you talked about the what you currently identify as, uh community builder. What do you identify me as? I mean community builder, entrepreneur, I would say. Entrepreneur or community builder, just knowing all the phases of your story from a high level. Um I think you're I think a good word to use would be self-aware of seeing where you could add the most value given your uh social proof, your um your momentum, and then being able to calculate what the next step would be to where you can um kind of like that through I've talked about this a hundred times. I might even talk about it on our last episode. It was like the three circle Venn diagram from um Jim Collins um good to great. Good to great, yeah. Whereas what you can be the best in the world at, uh, where you add the most value and what you can make the most money doing, sort of like right in the middle of that. That is so hard to, especially when you're set in the identity trap of what I'm currently doing is who I am. Um that's a good point.

Josh Hall

Because if people do chase to be the best at a certain thing, it's gonna take a long time. So you'd probably have to, and I th I'm very cognizant of this now because I've thought about this, which is like I'm not the best podcaster, not the best coach, not the best community builder, not the best, I'm not the best at anything, but I'm pretty damn good at a few things. And that is like really important to remember because I do think a lot of people want to be the best at something. And that is totally fine. You just need to be willing to commit a very long time. And that's you know, like if you look at any sport, like the best of the best are doing that for a very, very long time. And you know, when Tom Brady retires, the identity shift is a massive like is he the broad best? I'm not even like a football guy, so I probably shouldn't use this analogy, but I know he's a broadcaster now, and the question would be like, is he the best broadcaster two years in or whatever? Probably not. But you know, so like there is a thing there where like there's totally fine to want to be an expert and to be the best, but you just need to be willing to make the sacrifices. So I do love that frame of like, I may not be the best, but you know what? I know my value based off of my experience and like you said, the social proof and my journey, um, to where when I think about like this next evolution for me, which is a little more high-level and and high-ticket, even though I didn't run a seven-figure agency, what I've learned and what I see with hundreds of other web designers is well enough to help folks build a multi-six and seven-figure agency. Yeah.

Andy Milligan

I mean, that's the that's and what I've learned is that, and we talk a little about imposter syndrome, but I don't love that word. Um, is people don't care to a large extent. People don't care as much what you accomplish. Obviously, social proof plays its role. Um, but the way you make people feel is more so it's so much more, it's a more top of mind, but it's B just so much more important to either continuing a relationship, you know, finding again where you can add that value to people. Um it's uh it's just it goes back to like, can you help me as a client?

Josh Hall

Right. Can you help me with this? And you don't need to, you know, be an expert who's done something for 20 years, usually, especially as a designer, to help folks. And there's another um kind of like frame on this, a quote that I really, really love from uh Troy Dean, who is on my podcast. He runs agency Mavericks. And he's been in the game for a long time. Australian guy. Yeah, yeah. He's been in it for a long time. But something he said when I interviewed him was for web designers, you don't need to be the best. You just need to be the best in your client's sphere. Yeah. And that's an important thing to remember, too, because for most designers and web designers, we're service providers, we're working with clients. They don't know the industry and the entrepreneurial folks that we do generally. So like you may be looking at me or other web members of Web Designer Pro and feel imposter syndrome and feel comparison because we've been at it for a long time. But your clients, they don't give a crap. Like if you're if you're pretty dang good and you can help them, that's it. That's all you need to land a sale and to start building success, whatever that looks like for you. So I think that's a really important thing for when it comes to imposter syndrome for everyone to remember is you don't need to be the best. You just need to be the best for the people you serve and the people around you. You know, we really don't need to compare our like I don't need to compare myself with every web design coach ever. And frankly, I can't coach everyone in the world who wants web design business coaching. You know, I can coach the folks who jive with me and want my expertise. So I've learned that too.

Andy Milligan

Yeah, dude, so much, so good. Um the I want to touch a little bit on um WDP con, now procon, from what I understand. Yeah, thanks to Sam.

Josh Hall

Sam was like, dude, it's too hard to say. I was like, all right, fair enough. Yeah. Procon just sounds like a pro cons list, and I think there's other hashtags that use it, but it's all right.

Andy Milligan

I mean, I well, I I'm it's hard to get out of my home my own head, but I see it as pro-con just because I know the name of the community.

Josh Hall

Well, people were using that hashtag last event. Procon. I mean, it's web designer pro-con. Yeah. But pro-con just it's in the name. So yeah.

Andy Milligan

I mean, I don't want to give Sam too much credit. He might be right there. Right, right. But um so the way I would describe the first one was I was thinking of like what a good analogy would be. Um so I was thinking like, oh, it's like seeing it's like seeing all your your old friends again. It's like, oh, it doesn't really do it justice.

Josh Hall

I side note wish you were able to come to the event before and the night after, because it was it's you saw like part of it, like a big part. The the workshop was a big part, but it's definitely a lot to you.

Andy Milligan

I mean, that goes back to like the sacrifices of like the past year and stuff. I I remember that day or that night before and the day after. Um but the I was thinking of like a way to describe it. I was thinking of like, okay, I remember seeing good to see Mark, Sam for the first time. Um two people that I've just you know talked endlessly with, both of them on the podcast. Um there's something to seeing, something that real life connection, I think, especially now, yeah. Um when I see people like you and Jay who are a little bit uh ahead of the eight ball in terms of like where the puck is headed with um what people are really gonna value because with all the uncertainty, um obviously AI, all that stuff, um, people are valuing face-to-face um in community. But I was thinking of a way to describe it, and I was thinking it's not really like seeing your old friends again. Um it's kind of like a it's like a high school reunion if it was only with the people that you really liked, and there was no awkwardness. Um but there was a little bit of education there. So maybe there was like a cool teacher who then like put his teaching hat back on and now he's teaching you guys again, and it was a really good lesson. Um but now we're having uh quarter one of this year, having round two. What have you learned? What a what did you learn from the first event? Oh and you know, what are you what are your kind of tone and mindset around events uh in the future for pro?

Signal vs Noise And Owner Tasks

Josh Hall

You said it in that people value in real life over yeah, it's hugely, hugely important and valuable now. And not even just as an online community, but this is why I'm really encouraging even members to go to B and I groups and networking groups, because it's way easier to sell nowadays, especially in person. There is a whole there is a whole different vibe. There's a whole different connection, there's a whole different everything in person. Even this, like I'm not, I don't do in-person interviews much, but this is encouraging me and your favorite one. Yeah, obviously. This is really cool though. Like it's like this makes me want to do this more. It's just I'm so used to like doing, you know, looking into my camera that I feel like I should be looking above you, because that's generally what I do. Uh you know, I see you in the periphery. Anyway, all that to say, like we're we're getting used to digital connection and in-person or in-person connection is just so different and so much better. It's going from 2D to 3D. It's it really is. Um, my experience from the first one, I think the the coolest thing was wow, oh my gosh, I mean, how much time we got. It was personally, my favorite thing about it was there's um there's like a guard that's not there when people are in person that is there for some people online. And it's largely because we're doing group calls in pro or I'm getting testimonials where some people don't feel comfortable sharing everything. But I mean, uh there were people like crying next to me at ProCa, just talking about what the community meant to them, telling me stories that I was like, why didn't you tell me about this before? How did I not know about this? I mean, there were really some incredible experiences like that. Um, and there was just like a heartfelt release in a lot of ways. And uh, to your point, like you you hang out with people online and you get to know a lot about them, but man, in person, it it just is a whole other connected level. And what's interesting, my journey is is opposite from your generation, probably getting started now, because my journey as a designer did start off in person. Yeah. And I just wasn't a social media guy. So I was used to doing in-person and then bringing the digital component with calls and connection on Facebook back then. Now I think it's an opposite effect where most people are connecting online, and then you're connecting in person in a lot of cases. So I don't know if we'll see a shift as a whole. I mean, obviously, there's the two are really important. Like you go to a networking group or you go to a co-hatch event, you meet people, you connect online, and maybe you connect online, then meet in in real life. Maybe it's gonna start being 50-50 to that, you know what I mean, to that to that point. Um all that to say, like, yeah, in-person stuff, it's just it's just awesome. And for a community, man, like it like I said, I know I was bummed to not have you there. Hopefully you can come to the whole thing this year because it's going to be absolutely freaking awesome. We're running it back. Um But there's a there's less of a like in a in a web design community, for example, or a coaching community, you're probably talking about business most of the time. And that was the case in the social hangouts. But I mean, there are some times where we were just hanging and it was a very different, even like you, you know, you've come to a couple meetups with me in Austin and some other pros locally. Um sometimes those are a little more professional and sometimes those are not prof professional. Um, but they're equally valuable because it's just the different level of connection. Yeah. So I think that's what it is. I think digital connection is is just fake connection in a lot of ways, honestly. In real life connection, is just it's the real deal.

Andy Milligan

Yeah. Well, that's where you really get to know somebody, man. Like there's so much, and I've built and I haven't been in a couple years, but especially the biggest thing for me this year was like I you know how far I live an hour away from the city. I multiple times a week. Yeah, for now, yeah. Not much longer. I was always the one to say, Where where can I meet you at? I would for the f even to this day, I'll I come here multiple times a week and say, like, I want to meet you. And the impression that that creates a stickiness in their mind. Um and it's also it's just the oh, I think a lot of people are territorial with their time and they should be, absolutely. But it's just it it's just such a strong signal to someone to say, hey, you know, I I'm like you today. You came here into our space, and just the signal that that creates of like I am surrendering, you know, my morning to you, especially as I learn more how valuable people's time is. People really appreciate that.

Josh Hall

That's a good point. Yeah, especially as people get busier and more successful, right? In person does tell a signal of like this is serious. Like I'm gonna value this time and we're gonna make this the most of it. Because yeah, as you get, especially with kids and stuff, like I very rarely do any meetings now. So if it is going to be, it's and it's all affected too. Like even just during work hours today, uh, you know, my wife and I figured out like I'm gonna drop my daughter off to school and grab a coffee and then come up here and then be back around lunchtime probably. It it affects her day and what she does. Um, so any yeah, an anything like that affects a lot of people when it comes to the phone.

Andy Milligan

Yeah, and that's where like in the past I've gotten into trouble because it's like I I said I'll just fix my like I have all the time in the world, you know, no I don't have all the time in the world, but like no uh significant significant other, no kids. Um I'm just like, you know, what's let's do it? What what works? Um which I love by the way.

Josh Hall

I think it's yeah, you got the time, go for it. Yeah, it's not gonna be around forever. Right. That's what I mean.

Andy Milligan

That's a big part of what I'm trying to do now is like what can I build that to when those those lovely um forcing functions of balance in the future come up? Kids, family, mortgage. Um what can I create now to where when I don't have the time to invest, then you know I've set up something where it's a lot easier.

Josh Hall

And it going back to the identity thing, like if in-person meetings, recordings, but whether it's podcasts or networking events or whatever, if that is the most important thing for your business and that you enjoy, you could still craft a business to give you plenty of time to do that. But you're probably not gonna be the designer. You're probably not gonna be the support person. You really need to delegate the aspects of the business that are behind the keyboard and behind the screen. So there's an aspect to that too. Like I know I could do more in-person stuff if I wanted to. I would just have to get even more so delegative, if that's a word. Um and obviously, like with pro, I need to have a certain amount of time behind my computer doing coaching digitally. Um, it's it looks different. I did a lot more in-person stuff as a web designer, networking, and meetings and stuff like that. But yeah, to that point, like you you can still craft your business around that kind of thing, but you're definitely never probably gonna have as much time as you have now.

Andy Milligan

So everything comes at a cost, dude. That's like the biggest lesson from this year is like you see, even when you feel like you have all the time in the world, I'm just gonna put all my focus into this thing. There's the positive of that it it creates clarity. It's like this is the goal. But there's I mean, there's cost to everything. You just the numbness, um, you just you it becomes very visceral to a point. And you know, I'm trying to build something that I am like genuinely excited about doing forever.

Delegation, Design, And Staying In Your Lane

Josh Hall

What's the numbness for you? Do you think? Is it and I talked about this with Jay to where like it might be different for me just because mm talking about like the the feeling of not getting too high and too low is what I've experienced just as an entrepreneur. Um, mainly as probably a defense to negative comments or rejection or um which isn't in my world too much, but I've just learned to like if somebody has a problem with something, it rolls off me now. Whereas before I would stay up for nights. Unsubscribed used to keep me up. Now I don't look at those. So uh for you, I think the numbness might be different, but for you, is the numbness yeah, is it burnout symptoms, maybe? I don't I hate that word. Right, I know. I'm just trying to think of what else I don't know what else to call it.

Andy Milligan

No, I know it's um the the tangible way I would put it is like what you uh previously viewed as successful um doesn't feel like what you thought it would. It's just like the kind of the realization of like this is it sort of thing. Oh yeah. Um and you there's like you realize that, and it's like you even you and Jay talked about it in your episode, is like um see it start to manifest in yourself, whether it's like subtle signs of like self-sabotage, or like you're spending more time, you know, going on walks, or you just you subtly, you know, not dread, but you you look forward to other things. Um especially, I mean Jay said the thing of like you start to realize, uh like I was at the grocery store the other day and I was like, there's um the like the cashiers, like I was like, man, that'd be kind of cool to just like do that for a day. And like you start to lose the sense of like what does success actually mean? Like they look kind of like they look pretty happy, you know, they got a diet coke, they're talking to people. Um and I was like, yeah, it'd be cool to do that for a day. Obviously, it would get old, but you start to, you know, it I I think it's made me less judgmental and less more accepting of like everyone has to play their own role. Um, but when you go, made my mistake was when you go full bore and attach your identity to an outcome that you viewed as successful, it just doesn't always feel the way that maybe you thought it would from the Yeah, well, and it's probably because of the amount of sacrifice and everything else that had to be done to achieve you know a certain number.

Josh Hall

I don't know what your revenue goal was for 25, but 200k plus is yeah, that's incredible, regardless of how much of that was expenses and what lack of profit or whatever. But that came at the expense of your time. And um, even though you love what you do as an entrepreneur, it I don't know what your Off switch looks like or down gear looks like, but I I do think it's super, super, super, super valuable to just take a step back, even if it's one day. No email, not looking at any social media one day. It doesn't even have to be a day a week if if you're wired like that. It's just you do need to take a break and step back. And the danger of that is losing a little momentum if it's too long. Like as much as I love going on vacation and stuff, I like after seven or eight days, I'm like, all right, let's get back to it. Um But the the the the the change, like the literal change of state, the literal change of environment, all of that is so important to your well-being as an entrepreneur. And if you don't do it, yeah, I think you get to, I think that's probably the numbness. Is it is it's like, I mean, it it'd be like you're you know, you're driving a car and you're just in fifth gear the whole time, you're just reving high. Yeah. You have to, you know, you gotta you gotta go to lower gear every once in a while.

Andy Milligan

It's just like the the highs and the lows, too, is the biggest thing I've learned. Like I'll be like, I'll be at like a very big low, and then I'll just like go on a walk or go on a run, and I'm like, oh man, I'm ready to take on the world now. Um but I think that's just that's part of. I mean, I'm very still very green learning. I'm two years into this thing, you know. Um so I think part of it is just assessing the emotions on the fly. Um Yeah, because that you gotta enjoy it.

Josh Hall

Like when I listened to that recap, I did feel a little boned for you because I'm like, man, this should be like Andy's happiest state. But it was like we did. It was you know, you were pretty honest about it, you know.

Andy Milligan

It was like nine o'clock on New Year's Eve.

Josh Hall

Yeah. Which I mean, honestly, one thing you just coaching, like one thing you could do too is like just look honestly, like, do I need to do this or can this wait? And what's the priority? Like in that case, New Year's Eve, if you wanted to meet friends or be with family or whatever, everything else can wait at that point. I mean, you and I do think the like no quit, gonna get this done, that can be a problem when you put a to-do list or a task list in front of you and you're like, I'm gonna get this done hell or high water. But I've really learned to go back through more of a it's it's not much of a like task list as much as a priority list. And priority lists may be family time or time off or going for a walk or clearing time for that versus getting something out the door.

Andy Milligan

Dude, that's like the prioritization is everything. Because we all have the same 24 hours in a day, right? Difference between Bezos and not the only difference, obviously, but the difference between Bezos and like a struggling freelancer is they he can spend, or like Elon Musk. Not that these people are everyone's model of success, but at some level, they know what to focus their two or three tasks on in a day to create the most leverage that led them to you know the growth. And that's what's like, okay, that's where the skill is. That's what I think you're good at, is kind of giving you the the props of not like seeing the next steps, but like what given my current scenario, what I've built, my momentum, what are the the one or two things that I should be focusing on rather than like I think a lot of creatives or people who are just getting started is like I'm gonna go, I'm gonna make this thing from 98 to 99%, or spend my time doing busy work because it like feels good in the moment. I think that was so much of like my hours this year. Um like proving to myself that I that I'm like investing this thing just by throwing hours at it to where I could look back and say, you know, I I deserve this now, you know? What?

ProCon, Real‑Life Community, And Trust

Josh Hall

Um because it really it kind of reminds me of, I mean, in my scale, have you been through my scaling course yet? Yeah. So in there, I have a I just call it a task inventory, which is basically over the span of a week, two weeks would be great. Just really get granular on what you're doing day to day. And if you attach the task that you're doing to the role of your business, and in that course is like my recommendation is to do a role chart in your business, even as a freelancer, and you're probably filling 10 to 12 roles as a CEO, creative director, designer, support person, developer, et cetera. And if you look at the tasks you're doing, if you're feeling like that, I'm betting you're doing like no tasks as a CEO. You know? And the reality is like if you don't change that, you don't delegate or automate as much as you can of those I hate to call them like lower level tasks, but compared to where you should be as the business owner, then they are lower-level tasks. Um that's why I think it leads to that feeling is like, yeah, you're basically just doing noisy work. There's actually this idea of signal versus noise when you're running your business. And I I've heard that before, but I didn't really care about it until more recently, where I'm like, that is it. That because that's everything when it comes to busy work and doing stuff that you're like, I know I probably shouldn't do this. Yeah. Even though I can do this, I shouldn't do this. Um we talk about that a lot right now in pro. I was just talking to Mark about this because he's in that position where he's really embracing becoming the owner of his business. And I even like the challenge I proposed to him was as we talked about this idea of a task inventory and the role that he's fulfilling. I'm like, dude, a challenge for you may be to not log into WordPress for like two weeks. Yeah. And the place went silent. I mean, it was a call. It was a call. But you talk about an identity crisis. But really, like, could your business survive without you? Yeah. Uh and there's no shame in like, you know, being uh being the one who does a lot and wears the hats. But my thing is like you kind of whether you realize it or not, you get to a point where it's like, okay, I think I've, you know, what what what gets you here doesn't get you there. Right. I do think that hits a lot of web designers who are growing at a point to where they they really like they you need to become the owner unless you're partnering with somebody who's gonna be more of a CEO kind of thing. So priority, priority, and then really getting clear about the signal versus noise thing. And yeah, like looking at what like what's gonna move the business forward, where is the need at? What doesn't fill my calendar up if I don't want it to be? What are the type of things I want to do? What leaves time to like be with my family or work out or whatever it is? Yeah, what makes you enjoy it? Like what makes you, you know, get up and be pumped for the day. I you said you did a lot of team calls when I was listening to that. I'm like, why do you need to do that many team calls? Why don't you just do like one a week?

Intro

Yeah.

Josh Hall

Is there really a need to do something, you know, every every day or every other day? Is it probably not? Yeah. No. That's the answer right there. So just like I would I would do the bare minimum of this sounds like terrible advice, but I would do the bare minimum of like admin in repeatable tasks if it just isn't crucial. Yeah. Or try it, like do a test. Yeah. Try it out. Like maybe not just with the team calls, but like other stuff you're doing all the time. Give yourself constraints on like what if I don't do this for a week? Yeah. What would that look like if I force myself to just not do this? Um I actually didn't realize how much graphic design I was doing still until I really see now, right?

Andy Milligan

Yeah, Alexia.

Josh Hall

Alexia, yeah. And and I'm still doing quite a bit. So that's something I'm gonna delegate more of, although some of it's the problem of me like getting stuff out immediately. I do enjoy it still. And and I do find and I'm I'm cool with scratching that itch just because I think as a visual creative business coach, it still is important for me to even be able to like format a Google Doc in a nice way. Like I still like to keep the designer and me going a little bit, so web designer and graphic designer. But I did look at my Canva and I'm like, oh my gosh. And I'm sorry I use Canva. Uh I still use Photoshop and Illustrator occasionally, but it's mostly Canva.

Andy Milligan

I mean, have you ever tried a tangent uh affinity?

Josh Hall

No. Dude. I I would I would look at it. It would just man it well, I have my team's ingrained in Canva now. We have like a nice little process, but I think I use Canva now too. Okay. It's too fast.

Andy Milligan

You know.

Josh Hall

But I looked at that and I'm like, you know, like I I need to probably do a new task inventory. Because I was like, I did a lot of graphic design. I did a lot of graphic design in the past couple years.

Andy Milligan

Well, Alexia's awesome, dude. We actually got to work together recently with some of Sam's stuff. And she's just a rare hat of like marketer and like actual designer, you know?

Josh Hall

Aaron Powell Yeah, she's a strategist and designer for sure. Uh I mean I saw that in her as a a a member of Pro. And then once she got to a point where uh we talked about doing uh some graphic design together and I hired her for a project. I mean, she just blew my stuff out of the water. And I was like, all right, well, I'm never creating slides again, or I'm gonna have her make a template and base it off that.

Andy Milligan

I I think you reach phases where you're just like, man, I'm not not as good as this thing as I thought I was. Uh and that was me with a lot of the graphic design stuff. Um I think I definitely still have an eye for it. It's just like the execution of the very granular attention to detail with like vectors and logo stuff.

Josh Hall

Aaron Powell And it becomes to a point too when you have a business, there's a lot of hats to wear. Yeah. And the only person in your business to be the CEO is you, unless you have a CEO. The only person to be a creative director is you. The only person who is going to be a team lead, project manager might be you unless you hire those roles out. So I think the problem with craftsmen and craftspeople who do the work is you're used to balancing all those, but a business does get to a certain point where you have to ask yourself and just be self-aware, do I want it to stay at this level? And that's fine for a while if you want to do that. Like, that's fine to be content and doing all the things, wearing all the hats. But if you find yourself doing the lower level tasks or even stuff that just isn't your expertise, it takes away from the high-level stuff. Yeah. Like just recently, I found myself playing around with Divi and some of the new Divi5 settings and presets. And I'm like, I've got a member in pro who did it for 500 last year, and she's asking me questions and high-level questions at this level. And I had that on hold while I was working on some of these Divi presets and learning. I'm like, Yes. Like, is it more valuable? Is my time more valuable learning some intricate tech side of Divi or helping somebody who just made $500,000? Yeah. Answer is right there. Yeah. So I'm really kind of embracing more of a like, yeah, business strategist, business coach role, and most all of my stuff. Yeah. Um, I'll still do a little web design stuff, still doing a little design. Uh, and I do have that itch, and I do find it's a nice change. Because sometimes you do coaching and you're like, oh, I need to like sometimes I do like just throwing on a podcast and just doing a little, you know, half an hour of work. Yeah. Uh I do enjoy that. Uh, but I can't let that overtake the high-level stuff where people need me. Right. You know?

Andy Milligan

Yeah, it's hard to it's hard to be uh because we don't have but people telling us what to do. You know, that was the big thing I learned is like, okay, I have all 24 of these hours and nobody's telling me what to do. Um you can go too far on both sides of that. But the like the exciting part to me, and I see it you, Sam, is you see the skill sets of other people and you're like, that is awesome. Like, if I can hire them to work for me, I basically, you know, I can be the beneficiary of that skill set and I can, you know, wear it like a badge of honor rather than I think a lot of people who kind of stay in like the minimalist mindset of like, man, or the comparison trap, like, man, you know, they're better than me. I can never live up to that. It's like if I can hire you, you can you can make me, I basically adopted your skill set, you know. Like we're um redoing our site currently, and I got to work with a um a lady from Ukraine that I interviewed on like episode 30 of the podcast. She is a UI designer and she went kind of viral on Twitter. So I was like, hey, let's talk about client acquisition on Twitter and stuff like that. Um and now we have a budget towards like, okay, we're positioning towards healthcare, like what would some of these concepts look like? Just like the absolute highlight of my my day. Because I I have like the eye for design and I know like how long this stuff in Figma takes. Um I'm just like, here's a direction, just like cook. Um and that is like the absolute highlight of my day, is like seeing what she can come up with and going back to that Figma file and seeing it.

Josh Hall

And there's a big benefit to being a owner and a team lead when you've done the work.

Intro

Yeah.

Josh Hall

Because there is nothing worse than a business person coming in to start an agency and then they're like, what's taking so long? Come on. Like it's development designed. You can do it in AI. It's like, well, they don't know what's going, you know, like they don't know the heart the the craft and the hardship. So there is something about doing the work and then having that level. And there's a there's a mutual respect, I think. Um in knowing like, you know, this person, even though I may be better, they at least know quite a bit about this to where there's a little bit of like mutual feel like likeness there. Yeah.

Andy Milligan

Well, I think it's the respect because you know what goes into it firsthand. Like I see that's what it is. I see. I opened up the this is so, so rabbit-hole-y, but like I open up a tab and I see eight layers of drop shadows. I was like, you went and refined each of those so that it looked perfect. Um, this is like so, so unimportant. But um, I want to talk to you about your current identity community member. Uh, you alluded a little bit to what maybe your next one is or what you're currently um thinking about a lot these days. Um if you could give like a preview into maybe what the next sort of I don't want to say the next chapter is for you, but um what gets you excited to work nowadays and how is how is that funneling into your future?

Choosing Priorities And Saying No

Josh Hall

I think right now it's going deeper and more high level with the folks, particularly in pro who won it and have literally asked for it, but I just haven't had the option to you know do more intensive type of coaching. I think um I was just talking to my wife about this because I I literally just sprung the mastermind stuff on on her yet last night, which is not a huge change with what that's gonna be. It's still gonna be pretty contained, but it is gonna be more calls, and we may end up doing like a private event together in the fall kind of thing. So there's gonna be a few new things in the business, but I do think I I've finally reached the point where, like I said a little while ago, I mean, I made two and a half million dollars as an entrepreneur with like very, very small expenses and team. And there's a lot to that that I can help folks at six and multi-six figure levels, even though I may not have their exact same setup. Um, and and as a specifically in web design business, I'm in a really fortunate spot where I'm seeing pretty much every scenario of web design in every single model and every single tool stack. And I and I have a pretty good pulse on what's working. And I was just coaching a member on a one-on-one call the other day, and we came up with like I was like, dude, this was pretty freaking good. This is like he should kill it with what we did after talking. Um, and I'm I'm realizing like, yeah, that's like where the true value is. And I'm and I'm glad I got to the point where I mean, five years ago when I started pro, I really I was a coach, quote unquote, but I was really more of a mentor. I was learning so much about different business models. And I wasn't at a place to where I could confidently launch a $10,000 mastermind five years ago. But now, for sure. I mean, I've helped members, some of them have made millions of dollars in pro. And I'm like, yeah, my highest tier right now is 200 a month. Yeah. It's for not quite lining up to the value I think I provide in the market. So there's some of that I think right now personally. Um there the excitement for me is like, I like solving, you know, multi-six figure and seven figure problems. Yeah, I really do. And I'm good, the proof is there now. Um now I'm still gonna continue to strengthen pro and grow it. And I always, always, always have such a soft spot and interest in helping beginners. Um the the challenge with any community is mixing beginners and people who are at multi-six figures. The challenges are very different. You've seen it firsthand. The cool thing about pro is somehow we have got a really great mix of olive beginners, intermediates, and super advanced. Um I I need to be very careful not to mess that up. And the thing I'm probably gonna refine is on that first level, the the beginner, the course is only tier, um I'm gonna try to make it uh create better filters to where the the Andes, the Sam's, the Alexias, the Bins, the folks who are beginners, but they're gonna soar really quick. I wanna have a path for them to do that. Um but there's also a lot of people dabbling and people just learning and just need time to learn, especially if they're working full-time and doing web design on the side, to where like they just need time to go through the resources. So that's kind of what I'm doing is is kind of the next evolution of Web Desig Pro, at least, is gonna be better pathways for the folks who are early on and not having them jump ahead too fast if they're not ready. The community and coaching tiers currently strengthening where that is and getting people the the best results and then having a very you know tight-knit upper echelon group for the folks who want it.

Andy Milligan

Well, there's value in I know how hard it can be. It's like the problem of scaling. It's like you want to have the aspirational vision with the people who are you know slightly like I had that when I first joined with like Michelle, Mark, like I viewed it, I viewed at when I was in that stage of my journey, I viewed that as like, wow, that's so aspirational. That's success. And it's it is success. Um but then it can almost be like a um and Sam and I talked about this recently, is like there's just different conversations that different questions that you ask, different conversations that you have at different levels of your journey. Um and it is really hard to to you know have everyone be, you know, be in the same in the same pool because you you see it when um you're on both sides of it. And I've been at the the very green sides of it and slowly growing a little bit. Um quickly growing a little bit.

Josh Hall

I mean, you're already not I don't know too many people who have gone to multi-six figures in two years. That's not common. Um, unless you have like you know a business training or you come from a different industry. Like I could go into the community building industry and build a multi-six figure business probably pretty quick, but um it's because of the amount of experience. Like Pat Flynn is a good example of that. Do you follow him at all? Oh, yeah. So with his deep pocket monster stuff in the Pokemon world, um I know he mentioned recently a lot of people were like, overnight success. How did you just get so lucky? And he's like, dude, I've been doing this for fucking 15 years. Yeah. But it's everything you learn to get to that point. So there is something to that too. And I recognize that too, that just because somebody oh, this is a good point that you're think helping me think through. Just because somebody's new in web design doesn't mean they're a new entrepreneur or a new business owner. And they're gonna probably you know be much more comfortable and know how to do things a lot faster than somebody who's learning everything from the get-go. So that's that is a challenge. I actually you I'm curious to see your thoughts on this. I feel like because I was just talking about this with Jason and Shannon, Jason Grassi and Shannon Mattern, who I'm in a math monthly mastermind with. And we all kind of realize I feel like the the newbie market, the beginners are being bailed on by most a lot of creators. A lot of creators are going high level. Uh and yes, I am doing that, but I'm not cutting out, you know, my my beginning resources. Um but I feel like uh and it's no, it's not throwing shade to anyone who's a top-level entrepreneur, but I think the um the beginner market, and a lot of it might be AI with like are people just chat GPTing their way through getting started and and not buying courses or not buying programs. Some of that's probably the case. But I do feel a little bad. I see like so many, you know, Amy Porterfield just stopped um Digital Course Academy, which is one of the biggest courses about creating courses. And she's at a level where, you know, she has earned the right to coach top-level people. But I do want to, that's just one example of many to where I'm seeing more and more people move away from the the beginner crowd.

Andy Milligan

Yeah. Um I think it's part of just like what you have um a people like you and Jason and saying, you just have a better understanding of business as a whole to where if you solve, if you add more value, if you solve bigger problems, then exponentially you extract the value, you ext extract a marginal amount of the value that you create. So if you solve bigger problems, you can extract more on the receiving end of that. Um I think we're all and it also just like and from a um a personal time allocation investment, like you can't solve you can't get the the expectations of someone who's just at the beginning in terms of you know one-to-one mentorship, their expectations are still the same in terms of getting them to the same point. You see it with like working with clients. It's like the $1,000 client is gonna be the one who wants the most time is the most intensive, versus like the $100,000 client is just like, yep, good to go.

Serving Beginners And Building Advanced Paths

Josh Hall

And I think to that point I'm I'm certainly at a point where like coaching the the beginners can be very frustrating if they just won't freaking do it. Just like just go, just go to a BI meeting. I promise it's gonna work, but you have to do it.

Andy Milligan

I think so many not to cut you off, this is also not a good idea. It's like so many people I feel like um and if I could attribute any type of success to anything, it's one, I want to be talking to people who are better than me at everything. And I think a lot of people kind of can get that. Like they don't like exposing themselves because they see the contrast and people that are ahead of them, rather I'm just like, dude, you know, like and then reach out to you is like you've accomplished something that directionally I'm inspired by. I'm behind you. What can I learn from you? That and also the um um I just lost the second part of it. Um but the Just wanting to be people who are ahead of you and not viewing that as a downside on your own stuff or seeing that as a shortcoming on your end. I think this the environment of wanting to be around people who are ahead of you is just a net positive in all sense of the word.

Josh Hall

And there's also I've always felt like as an entrepreneur, you need going to back to more like a sports analogy, you need a coach, and you may be way better than them. If you're playing hockey, you're probably way better than your coach. But he knows or she knows more than you probably do about this a lot of the mindset things like on the ice or whatever. So you need a coach, you need somebody to guide you and direct you. You need teammates who are there with you in it to experience together. But you also need fans or cheerleaders to like to be there. And ideally, you have somebody below you that you're you're sharing your knowledge to. I think about that a lot of like this you're in the middle, and again, above you is a coach, besides you are teammates, besides you are cheerleaders. And below you is somebody you're teaching. So I've thought about that a lot. Um, about and I think pro is like the example of that. Yeah. Because we've struck a really good chord. But there are, I we're at a point now to where I don't want to exclude beginners at all, but I do want to make it to where because it is a premium experience and premium community of a lot of people doing a certain level of business that have a certain level of challenges, I think what's going to become more of a thing is to where like is we're going to be more selective on the people who are beginning, at least if they're going to be at the community and coaching tier. Maybe that makes it be an application process. I don't know. It could have been a good idea. Yeah, exactly. But but a lot of it's personality, like we talked about earlier. Like if I gave you an application to join pro, you probably wouldn't have met the criteria. Right.

Andy Milligan

But I could tell, like, okay, Andy's got something. Well, I mean, part of it is just like you see, just from the outside, like you see someone that you want to be like, and you're like, that's what the like the community is. Like I want to be around more people who I view as you know positive attributes. Um, I think even going up marker, you could almost start that as like something that's closed door to the people that you see meet the criteria. I mean, that's your flexibility as the leader and community owner, is you know the people that are within there best. Uh, and that's that's kind of goes back to your other skill of like seeing introductions and connections. You're so good at making like when I went to your event, you remembered from our first show a year and a half ago, like my enamorment with Jay. And you're like, hey, Jay, this is this is Andy, and you told him, like, yeah, he's does your monthly retros, he watches your show, big fan of yours. And I was like, dude, like the the mind share that you hold in someone's mind as a connector is one of the most valuable positions you can hold. It's just you always remember the way that you feel when you were connected with someone else. I mean, you're that middle of the connection, just an exponential thing. And I've learned that as I've you know grown and built a network. Um that's a great point.

Josh Hall

I appreciate you saying that too, because it it um validates my value as a connector and community builder. Shannon hit on that recently too, because we were talking about some pricing stuff. And she's like, Josh, the value of so much of you is your network and your connections. And every and it's true. Like it does, it helps bypass a lot. And that's gonna be a value add for you know, my mastermind folks and in the coaching tier is like you get access to my network. That is 16 years in the making. Um but yeah, I really appreciate that because I didn't think anything of it, honestly. It wasn't until you reminded me of that that I was like, oh, that's right. Yeah, because I I was pumped to see you and like, oh, Jay's right here, he's not talking to one you guys, you know. Which can get really annoying for some people when there's like a matchmaker where it's like, oh, I don't want to do this. But I think if there's a level of trust, people know like if I introduce you to somebody, it's gonna be it's gonna be worth your time. Yeah, absolutely.

Andy Milligan

I mean, it's trust is everything. That's the biggest point Jay and I hit on is um when it's in limited supply with everything that's going on, like when you feel it for the first time and you really buy into it, you attribute that with a person and it just sticks in your mind. And um it's it's one of the most powerful emotions, I feel like. It's cool. Um but dude, I I don't know how long we've been going on. I've been looking for that email. It's yeah, it's been a while. Not bad. It went by really fast. It did, yeah. And like I said, I'm I'm good for a while. So Okay, cool. Um Well, the one thing I did want to ask you is um talking a little bit about the beginners. Um people who are entrepreneurial, you maybe see a sign in them like maybe you saw in me. Do you still and this is gonna be kind of an on-the-spot question, but do you still recommend people get into web design today? Yes.

Why Web Design Is Still The Best Starting Point

Josh Hall

For sure. For sure. Because I think web design, and this is not just because I run Web Designer Pro, it is you will. And this is what I this is what I see with a lot of web designers, it's almost all of them after a certain point realize, oh my gosh, I'm like a webpreneur. Because when you do web design, you learn design, you learn basic HTML and good online best practices, which are going to carry over, regardless of how tools change and how AI is and the place of it. Markup for the Internet is still the same best practices, the same stuff. So that's really important to know. Marketing, copy, positioning, messaging, offers, client communication, you're learning all of these specifics, and you're on the front line of I mean, the reality is a website is a digital home. And regardless of what happens in the industry of web design with AI and different builders and how easy or hard it is to create and all the different options, everyone is still going to be online to some extent, whether it's on the phone or apps or whatever. Everyone needs a home. You know what I mean? Like it's still I think yes, the industry is is in flux in the sense of there's a lot of changes happening at once, but what is not changing is a business owner needs to sell online. And all the tools in the world that GoDaddy provides or others, you know, maybe there's decent starting points. But you get to a certain point where you need someone who can help with all those aspects. And we haven't even talked about lead generation and email and and the marketing side of things, like in business strategy when it comes to online. There's I mean, how many things that I just hit on there are like 12 or 13 different roles that web designers are unknowingly filling and doing? That's the key. And I what the problem with I think people who are just focused on marketing or coaching or just copy is they you have to partner up with somebody to do the website. You just have to. Because if you work with a client, they're gonna want to do the web stuff. And I think if you're somebody who starts with web design, you have now worked on the home of the digital presence. And then you can expand in other areas. Like there are people who I've seen come through pro who just like like Sam, SEO more, or they like Michelle, just like copy more, or certain members like productization more, or certain people like branding more, certain people like marketing more. But web design is still a really important part in there. Um and so I think if you start with that, you can much easy, you can much easier uh branch out and still bring a ton of value with that. And maybe you're not doing the websites eventually, but to their point earlier, you know you can work with a web designer and you're not just some business person who doesn't know what they're going through. So yes. Um now, do I tell everyone to be a web designer? Kind of awkward because I run web designer pro, but uh to start, but pretty quickly people are becoming more of a web strategist, a web marketer, a web owner, web business owner. You know what I mean? So I think that's the consultant. Yeah. But most people still know the term web designer. Right. If you go to a networking group and say, I'm a digital web strategist, people are gonna be like, heck does that mean? You know, like and then the question is, oh, you do apps? Like, no, I don't do uh so I still love like I'm a web designer, or I run a web design agency. Because if you say that, or a web design studio, web design business, if you say web design business, web agency, that they're gonna know you probably do websites, but that's gonna open the door for other things if you do that. There's also no shame in just being a damn good web designer, especially for a while. The world is starving for actually like good web designers, surprisingly. Because a lot of people are doing too much at once.

Andy Milligan

Yeah. Yeah. Well, I mean, there's always gonna be value in specialists, and I've learned this now that we've started to hire a little bit and work with contractors, is they're actually um like we have like our taste and what we think good looks like. There's actually a lot of people out there that don't meet that. So if you can be good and a niche skill, even if just to a respectful level, and you combine that with some of the people skills we talked about earlier, communication, you're already ahead of the game.

Josh Hall

For sure. And it's a lot easier to get pretty dang good as a designer than I think it is to, you know, if I were to come to somebody and say, okay, we're gonna learn communication and networking and marketing and copy and all these things at once, it's like, oh, where do I even start? But if you make if you get baby steps to like being a good designer, knowing how to build a site from start to finish, knowing your tool stack, release other tools, and then getting a very quick result for a client, even if it's just a website that's up. Especially nowadays. I'm glad you asked that question because everyone's like, is I uh gonna make a websites irrelevant? Um the internet is so cart compartmentalized and scattered that even more so I'm seeing there there's a bigger need for a like killer digital home, truly. Um and yeah, it's all the website principles. Yeah. And I think there's a lot of value to becoming more of a strategist marketer, but you don't need to jump to to there right away.

Andy Milligan

Well, I think from like a business standpoint, too, your main value should be adding the I mean, your your core mission, whether it's your marketing, whether it's the services you offer, should be adding the most val becoming as valuable as can to that ICP, to the one person you serve for you. And even throughout the multiple phases of your career, it was web designers, it was courses, it was community, it was the curation, even with a mastermind, you're like, how can I add the most value that I can to this one specific person? And you can go upmarket or downmarket with that. But you more the more you the more narrow and focused you get on what who that person is, you can serve them like uh out of obviously industry-dependent, and the analogy breaks down at some point. But if you say, I have this very important person, I want to help them in any way possible, they'll come to you whether it's for the one specific service you offer, or you can experiment just taking a business lens on it as like, okay, well, maybe they get more value out of this thing. There's kind of two different approaches you could take to the business where it's like you have the person in mind and you're building the business around serving them best, and that informs whether you do SEO or healthcare or or or design specifically. But if you start with that person in mind and you create content around them specifically, it's a lot hard because it may not be objectively interesting to you. Yeah.

Josh Hall

But it's no, you bring up a good point in that there's two ways to create a business and offer services. You can like be proactive and figure out your your ideal customer avatar and then build around that and bring them to you. Or if there's already people who are in your sphere, clients, customers, students, whatever, you can create things that they ask for and they need as long as it aligns with you and you want to do it and you think you're a good fit for it. So for me, I've been in the ladder camp most, at least as a um well, no, actually for my whole career as I think about it. I started design because we were playing a show in my rock band and somebody asked if I could design for them.

Intro

Yeah.

Josh Hall

And then my church I was helping out with asked if I wanted to help out with the website, got me into web design. And then clients asked me if I would help them out with SEO, got into SEO. And then when I uh Legate Themes asked me if I wanted to contribute to their blogs, so I contributed to their blogs. Web designers asked me if I could help them learn Divi and build their business, helped them with that. Yeah. And then a lot what's been interesting is a lot of members of ProNow were there from the very beginning when the doors launched, or doors opened when we launched, and they are completely different people now, which is awesome. And I'm I'm basically like to the point we talked about earlier, I'm this the more high-level approach is because it's been asked of me to help people on a higher deep, multi-six-figure level. Um and with the tricky part about this is when you are in multiple industries, like I'm still as a community builder, that's a whole different niche. And I am, because I've done some circle tutorials, I'm getting hit up a lot for community community builder help. And I would I definitely would love to do that. But I'm like, I I just I know myself. I'm gonna go all in and I'm not ready to sacrifice my time in pro or my family. You know, like if I if I if I didn't have three little kids, I'd probably have the time to be able to launch a separate wing of the business for community builders. But that's a whole different thing. Um will I do something private later this year or into next year? Maybe. I might consider opening up like a just a small group of community builders at a higher level who basically vice versa to how I started teaching web designers, which was from the bottom up, basically. I would probably start from the top down. Yeah. If I do anything community, because it also would feed my business now. It'd be I I do feel like there's a bit of a lack of um a network for me and colleagues who are community builders. I do have a few, Jay, a couple others. But that is one area where I'm like, I almost feel like just like years ago, I had web designer friends. We were some some we were coming up together, some I was learning from. I feel like there is a lack for me as a community builder and coach. Um I feel like I need a little more not necessarily maybe coaching, but also just like a little more um mentorship and examples. I need more colleagues as community builders, is a little bit how I'm feeling. So yeah, but I I know myself and I know at this juncture because I'm taking pro to like kind of next evolution, I need to be careful not to fill up my calendar and launch a whole new community builder program and all that. It's gonna distract me.

Andy Milligan

So I think well it's good to hear like um it's just from someone in the beginning of their journey, like the the the shiny objects will always kind of be there. Oh, they're always there.

One Umbrella, Many Identities

Josh Hall

And it gets so much worse because there's so many opportunities at a certain point. Uh that conversation that you mentioned with Jay, he talked about it too. It's like you're just used to saying yes to everything in the beginning. And then it is so true. I mean, it was very wise advice from him, which is you do need to get used to saying no almost all and not even no to people, but no to yourself. Yeah. Which is really hard as a multifaceted, passionate.

Andy Milligan

How do you how do you choose what to say yes to? What's the filters you run it through?

Josh Hall

Calendar is a big one. Um the priority of pro, for example. Like I just I don't want to take priority or signal away from something that's cruising and doing great. And is not to the point where like like I'm pro is five years in, it's stable, but I there's a lot more work to be done to improve it and to refine it and to make that better. And to maybe free up some of my time even more so. So those are the filters there, which is yeah, the priority of the current business. Um, and then obviously, like, yeah, my calendar, my schedule. I could very easily fill up my calendar with more calls and more stuff to do, but unless it's gonna be super, super worthwhile, and unless I like feel like, okay, I'm ready to really dig into this. And I know myself well enough to know that I have a very hard time doing two different things at once. Um I like going all in on something, which is great when you want to do it, and it's a part of a part of the next step. But um yeah, it's one reason I don't have like a whole community builder business right now.

Andy Milligan

Um I think it you what it that teaches me that it kind of builds the asset that is yourself. Like you eventually create a position to where you have higher leverage and whatever you decide to do. Um like five years ago, that wouldn't have been something that you could dive into. It's just true. The the harder decisions are just the yeses and no's to when the no just the no's are a lot more appealing.

Josh Hall

And you know there's two types of entrepreneurs, I think, when it comes to the the sharing aspect. You're so you're uh from Mark Cismansky. We just talked a couple days ago.

Andy Milligan

I was gonna ask you about that one. I just was on the phone with them earlier this week.

Josh Hall

I know. I know my family had a wicked flu cold or something last week, so I had to reschedule both of you guys. But um you and Mark are in similar categories of I think you guys are like experiment and share as you're doing it. I'm on a different category of I like to do it, build it, and then share. I don't like to share. It's why I like I share a little bit about community building stuff, but I'm not like more so like business revenue as an entrepreneur and some things I'm doing, but I'm not like here's I'm not posting content about like here's what I'm doing for our onboarding sequence and pro. I I'm not I'm not an experimental builder. Um, but this year, probably by pro con, pro will have crossed the million dollar mark in top line revenue. And I think once I hit that, I'll feel like, okay, I can officially say I've made a million dollars as a community builder. Yeah. And that's just with pro. That's not including I have a DV Facebook group with courses and stuff that so technically it's more than that. But I'll just be officially be able to say, like, I have a million-dollar community. Here's what I've learned. And that would give me a lot more not just confidence, but track record and proven kind of things to be able to expand on that. Yeah. I definitely will be doing some sort of community building resources. And um, but again, I just I can't run I can't run Web Designer Pro and Community Builder Pro at the same time. Yeah. Um so I might start high-level.

Andy Milligan

Yeah. I think part of it is, and so I'm kind of dealing with now, is like the how can you work what you what the interest is, what the shiny object is into your current business so it's not a distraction. Um I think masterminds might be a point of that to where you're still having some of the higher level conversations, but it doesn't look like you um like throwing the um the baby out with the bath water in terms of what you've already built. Um that's huge.

Josh Hall

That's that's really crucial. And I think that's why going back to your question of should somebody start in web design, I think yes, because it is the middle central piece that can take you a ton of other places.

Intro

Yeah.

Josh Hall

Um and you can scratch that itch. Right. You know, like just like I did with a little bit of SEO, a little bit of design, a little bit of marketing, a little bit of copy, a little bit of conversated optimization, conversion, like you really can scratch a lot of entrepreneurial itches. And as I'm seeing a lot of members of Pro become webpreneurs, they're still doing websites. It's just a part of like the main part of their bigger offer. Trevor Burrus, Jr. Yeah.

Andy Milligan

Well, that's what it teaches you. It's just you have to find what you want to double down on. And if you don't get reps in terms of like putting yourself out there, trying things that are like 10% out of what you identify as or what your track record is, you never grow to a point to where you can choose like this is yeah, we got a really good feedback, or this is what I can double down on to then grow more opportunity, you know?

Josh Hall

And it it's kind of cool, at least with my current setup as an entrepreneur, course creator, community builder. Everything I mentioned a little bit ago as far as my identities, course creator, coach, community builder, podcaster, YouTuber, networker, now event host, it's all still under Web Center Pro.

Intro

Yeah.

Josh Hall

Which is cool. Like it's not like I have a separate podcast that's unrelated, not a YouTube channel that's unrelated, not a community that's unrelated, not courses that are unrelated, not events that are unrelated. It's all under Web Center Pro. So I would say anyone who's like you and me that has a lot of different interests and wants to do a lot of different stuff, pack as much as you can under one umbrella. Um if it's newsletter, if it's writing, if it's client work, it's like they don't all have to be separate if you can serve your audience in in some way. Right. And I do there is um there is truth to this like seven-year itch that I've found at least the where after about seven years, you're probably gonna feel done with something as an entrepreneur. And sometimes that may be sooner, sometimes that may be later. But if at the at the very least I would try to like be okay with adding a new wing of services or adding something to challenge you and do something different. There's a member in pro who because I th we're recording this early in 26. I just did my like let's talk about 2025, let's talk about goals, talking about the year, not just revenue, but feeling.

Andy Milligan

Yeah, there's a really good newsletter when most areas check that out.

Seven‑Year Itch, Next Evolutions, And Balance

Josh Hall

Trevor Burrus, Jr. Awesome. Thank you. Yeah, I mean, um the one thing I was interesting is some of the pro members who have been doing it since 2016 and 17 some of them have said like things just feel a little stale. They're not bad, they're not great, they're just kind of and and there is, I think, a lot to that. Like you do something for seven years, you gotta spice it up. You gotta switch it. You gotta switch it up a little bit. And doesn't mean you the problem with that is a lot of people, I think, just bail on their business or start something new. That's not what I'm saying unless it's an important part to do it. But a part of that is like, well, yeah, just like add a new service or do strategy or consulting or do something higher level. What would it excite you to charge a lot for a few people? Yeah. Which is kind of where I'm at. I mean, you know, pro is five years into it, but my like course community business is seven, eight years in. Um I started web design in 2010. Uh 2017 is when I started courses. 2017 is when I started courses, and then 2024, 25 is when I really started doing more high-level coaching. So um, at least, you know, my 14 years of the seven-year itch is like dog years. For me, yeah, yeah, right. Um and again, it it's not always a seven-year exactly, but uh when I heard that, I was like, I felt called out because I was like, oh my gosh, that's totally true. Yeah. Literally, for me, like every seven years so far, it's been like a a nudge to either sell in transit, uh, which I did 10 years in, but I started doing courses. But there was certainly a pool to like do something expand, do something different.

Andy Milligan

Well, maybe like another way to look at that is like that's the amount of time it takes for the 10x opportunity to reveal itself to you to where that is the next thing, you know. But I think it takes um it takes a certain amount of time, like you said, to build the momentum to get to that point. And maybe that lifespan is about the same as um and maybe I mean maybe uh like I um there's thing like I think the mindset you take to everything is so important. Like I at one point said, like, what would this objectively how can I change my mindset about getting back in front of the laptop doing what I'm currently doing? Like, what would this look like if it was fun? I think you can apply that mindset to anything. Um, especially when you don't um a term I've become endeared with is like um and me and Chris, he's one of my other mentors. Uh I call it founder mode. So like that's like a version of like in a super fast, super accelerated time span, you give into like those shiny objects and you just like this is like I'm gonna you know redo the whole website by myself. I'm gonna make a monumental decision right away. I think when you uh give into that too much, that's when you lose a lot of the momentum. Um and I want to be really cognizant of that because sacrificed a lot to like scratch and clawed, especially in the beginning, I think that's important. And they always say the first uh the first six figures is the hardest. Uh God, I hope that's true.

Josh Hall

But and some of it, I I think for you, you've already at this point earned the right to like take the foot off the guest if you want to. And a lot of it is like, again, I my challenge to you right now, Andy, would be like, do I need to do this? Or do I need to do as many calls? Or do I need it really for you, I think, is just priority. And I mean, the thing is you're still gonna love all the different aspects of it probably with rightly so. But if you do anything too much of what you love, it's you know, if you eat too much cake, it's gonna make it feel like shit. So you know just go easy on the entrepreneurial cake this year. You know, like just let you know, do it in smaller bursts without uh overwhelming yourself. Yeah. Because anything that's fun can be very unfun when there's too much of it, or when there's too much pressure. Stakes, yeah. Or stakes to it. Yeah. So I I do actually think like I you said this earlier, but you kind of alluded to like even if you make less top line revenue but you enjoy this year more, that would be a win. I would I couldn't back that up more in saying that. Um yeah, it would be cool to say like we've had year or year of a growth, but at what? At what cost?

Andy Milligan

It was even I read Jay. Um Jay does a really good month or yearly recap every year. He writes a whole article on it, and it's like he had financially a down year, but then it's like you add all this context, you know, it's like, okay, net on net, like there's always gonna be positives, always gonna be negatives. It's just when you get into the headspace of viewing like financial revenue is just so it's so tangible because it's it's a number, you know, it's so easy to quantify, whereas things like emotions or um your just day-to-day enjoyment, it's just it's harder to quantify when you do a massive end of your review, you know? Yeah. So I got it attached from because that's like knowing me as an entrepreneur as a person, it's like the moment I start tracking something, that is like that makes it so easy for me to just improve. Like track calories, track miles, track revenue. Um, and that you can put that ahead of so many other things that are actually objectively more important, man.

Josh Hall

Um I do uh I love the idea of like a recap in the tangible of revenue, expenses, profit, but I would love to see a separate graph that's like yeah, time, enjoyment, fulfillment, you know, like what would though what would that pie chart look like? Stress, put stress in there, put over one, you know. That would be an interesting. Again, I guess it you just have to be super self-aware to look back on a year and say, like, okay, you know, 100% of my emotions, you know, certain amount was happiness, certain amount was stress, certain amount was freedom and content, certain amount was excitement. Um that could that that would be pretty interesting. It's actually a good challenge.

Andy Milligan

Yeah. Well, I think you know, for round three, um, those will be I'll be reporting back on some of those metrics. Yeah, yeah.

Josh Hall

So I know I want to see, I just want to see you happy doing what you're doing, you know.

Andy Milligan

I I think but yeah, there's and I've told like people that are closest to me too, is like happiness doesn't always manifest itself the same way.

Josh Hall

Sure, totally.

Andy Milligan

There's totally, totally. Yeah.

Josh Hall

So I think and I am not against hustle and grind at all, especially when you have the time. And and honestly, like business is freaking awesome. It's really cool. Yeah. It's really, really cool if you if you are wired like you are. Um but I think you've caught yourself at an important juncture to where like, you know, the the stress and the overwhelm and that admin and the calls and all that stuff can overtake all the fun. Yeah. And just real quick, I mean, I learned this being in a band. It started out so fun. It was like we were making music and we had people showing up at shows and we were selling merch. And then it didn't take too long. It's like the story of every pursuit creatively. Money takes over, stress takes over, relationships, communication becomes fractured.

Intro

Yeah, I forget where you started.

Josh Hall

Yeah, yeah, yeah. You forget where you started, or you just lose you lose the fun. You lose the joy, you lose the spark. So that would be my biggest thing for you is uh I still want you're gonna work hard. You're gonna crush it. I I would just lean into the idea of making sure you're enjoying it. And if you don't, yeah, we're gonna have boring times, we're gonna have stressful times, but just don't let that overtake your overall feeling for too long. You know, I think it's okay to have a a down day, but you don't want a down month or a down year, god forbid, you know? Yeah, like like feel like you know, feeling.

Andy Milligan

Yeah. Yeah. Dude, I I've imagined that I've learned from you for a long time. And um, I think we're having this conversation at an important time too. Um, just like when I I first got exposed to your stuff. So, dude, it's been an awesome conversation. I'm beyond grateful for um getting me down this path to begin with. Um, we're pretty deep in the rabbit hole now, but um and just this is truly like um a full circle moment for me.

Josh Hall

Um, I'm uh I'm not surprised that we're here two years later from our first interaction, and you're you know renting a chick ass space and you have a killer show and you've made, you know, several hundred thousand dollars now just a couple years in. So but uh yeah, man, super proud of you for sticking with it and doing it. I mean, you are a boots on the ground kind of guy.

Andy Milligan

So cheers and keep at it, man. I want to give you your flowers, man. Um there's um I highly encourage listeners to check out the newsletter. That's where I would go first. Um and getting started there will get you down the lovely rabbit hole that is Josh Hall and web design. Um anywhere else people should go or be uh on the lookout for?

Closing, Links, And Where To Connect

Josh Hall

Yeah, just go to josh hall.co. That's yeah, you can sign up for my newsletter, listen to my podcast there. And then if you want to enter my world as a beginner or uh uh, you know, uh a higher level established entrepreneur web designer, web designer pro is where to go.

Andy Milligan

Awesome. Well, Josh, take it from the thanks, Andy.

Josh Hall

So again, I hope you enjoyed this one. Uh had so much fun in person. Definitely plan to do some more of these. We covered a lot of links. I really recommend that you connect with Andy. Uh he's most active on LinkedIn, and you can check out his website, mmgdesign.net. That's going to be linked in the show notes. So again, go to joshhall.co slash 421 to get connected with Andy via his website, his LinkedIn. You can check out his podcast, and I'll make sure to link to our previous conversation on his podcast as well. So big thanks to Andy for this incredible conversation and for allowing me to repurpose this for you on the Web Design Business Podcast. I know he would love to hear from you. So again, connect with him on LinkedIn or drop a comment at joshhall.co/slash 421. All right, my friends, cheers to this in-person interview and some more of these to come.

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