Main Street Makers

#8 Tammy Valentine: Going from side hustle to full-time success

• Episode 8

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Listen as Tammy Valentine, owner of LuckyTamm Marketing Group, shares her journey to build a successful marketing agency from what was originally a side hustle. Tammy emphasizes the need to delegate as a business grows, and how important it is for her to be the opposite of a micromanager. Additionally, she touches on the common traits of successful small businesses she interacts with — ending with insider tips on marketing oneself authentically and taking risks.

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Tammy Valentine (00:00)

Don't be afraid to be humble, be authentic, and really take risks. Wayne Gretzky says, “You miss 100% of the shots you don't take.” Be willing to take risks and try different things. At the end of the day, you might not win but at least you're going to learn something and that's part of the journey.

Nav (00:24)

Welcome to Main Street Makers, a bi-weekly podcast that features real local small business owners who have transformed their passions into profitable businesses. Learn from fellow small business owners on how they overcome challenges, find opportunities, and create thriving operations that make our neighborhoods more vibrant, connected places to live. I'm Catherine, and this podcast is brought to you by NAV, the business credit platform that believes every small business owner deserves the chance to succeed. Now let's get to this week's show.

Catherine Giese (00:52)

I'm really excited to welcome Tammy Valentine, owner of LuckyTamm Marketing Group to the pod. She owns a marketing agency that focuses on elevating businesses’ brands. So first off, Tammy, I'd love for you to just share a little bit about your business. How did you start and what are you working on right now?

Tammy Valentine (01:09)

Well, first of all, thank you so much for having me. I am so excited to be here. I started the business 11 years ago out of really passion for storytelling. I come from a journalistic background. My undergrad is in mass communications, sports broadcasting and electronic media. At one point in my life, I thought I wanted to be a sideline reporter. So telling good stories has always been my passion. And that's really kind of where LuckyTamm was born. So what do we do? We are a full service, boutique marketing agency. We provide everything, you know, digital from branding, design and development to web, social media management content, and of course, strategy. So we are known for helping bridge the gap between operations and marketing. And we often help marketing directors who are overwhelmed and have limited bandwidth, we make them look good. And then we also serve as a marketing department for small businesses that don't have the time, the energy, but know that they need it.

That's primarily what we do. What I'm working on now is trying to streamline our tech stack. And so my big thing this year has been investing in the company, investing in training and the tools because there's a million tools out there, especially with AI. So I've really been working to see, okay, what do we need? What don't we need? And how can we make our operation more efficient? So that's really what I've been working on from a top level.

Catherine Giese (02:47)

That's really cool. You've had such a journey from sports broadcasting all the way to marketing and now really just running a business. I love that journey. That's so interesting. So while we were prepping for this episode, you mentioned that you have always operated in the black, so cash flow positive. What's kind of your secret?

Tammy Valentine (03:03)

That's a question that I, I like to keep close to the vest, but what I would say is that, and, something that I don't think is quite a secret, it's just more so hustle. Right. So I'm not sure just if I'm crazy or just a workaholic, but in bootstrapping this business, I've just always worked like, you know 50, 60, 70 hour weeks like work. You know, tell younger people that are like, you know, coming up into the ranks, like, how do I climb the ladder? I'm like, outwork everyone in the room, and you'll always have a seat at the table. And I feel the same way in business. And so how have I all been cashflow positive? I think the other thing is just being very smart and conservative with with monies.

In the beginning, you have no idea, right? And you take whatever it is that people are willing to give. And so what I really leaned into were mentors and people that I deemed as super successful business owners, not necessarily in marketing. They ran various other businesses, but there was a serial entrepreneur that I really leaned into and he was so kind to me and just basically gave me the insight into, making sure that whatever you think something's going to take quadruple it because it always takes longer. 

And so that's something that's kind of always been in the back of my brain. So, you know, with estimates and even project management, like the critical path, that's something that always add in is just like, just add in an extra amount. Like an extra barrier or just, you know, extra room, just because you never know when an unknown is going to come up or when there's going to be some kind of financial emergency or just something else that you're going to cover. So you think it's going to cost this much quadruple it because that's normally, you know, kind of how it goes.

Catherine Giese (04:59)

Yeah, that makes a lot of sense, playing it safe, being conservative. That makes a ton of sense because that's how you end up in trouble when you're not planning for the worst. I would also wonder, you know, some people go all in on their business when they first start. Some people kind of start it as a side hustle. What was your journey there?

Tammy Valentine (05:03)

That's a great question. That is a great, great question. And the truth is, it was a side hustle. I started the business and then I got a couple of clients and I was like, I have no idea how to manage taxes or like consistent invoicing systems or finance. And I had this electronic media background, so I knew how to get the end product.

I knew how to provide the service, but I didn't understand those basic business essentials. And so while I was getting my MBA, I was also working full time and I had LuckyTamm on the side. So some people like to, you know, just dive right in. And I preferred to err on the side of caution and, you know, pull the boat up to the dock. Then at the appropriate time, I was able to step off.

Catherine Giese (06:10)

That makes a ton of sense. When did you kind of decide that it was the right time for you to go full time in the business? Like what kind of did you need to see? How are you feeling about it?

Tammy Valentine (06:20)

That's a great question too. What was the catalyst for me was finishing my MBA. So I felt like that level of training was complete and that I had everything I needed on the foundational side of operating the business. So there was that. And then, I had this desire to just, you know, run my own thing. And then I had a ton of work coming in. And I just felt like it was the right time in which I could also offset my full time income with what was, you know, coming in. And so I knew that something had to give and that that was, was, it was time to either sink or swim. 

And in that case, I'm not sure if you've, you've heard the story of like Cortez and the burn the boats, but like, I was like, I'm going to just, I'm just going to burn the boats and go for it. And either I'm going to survive. And it's going to be great or I can always go to work for somebody else. can always go back to my MBA. So the rest is history.

Catherine Giese (07:22)

Yeah, I love that. This might be kind of a controversial question, but I feel like some people feel like they need an MBA, they feel like they need a business background in order to start a business, and other people feel like they can kind of just go through YouTube University, as some people call it. Where do you kind of land on that?

Tammy Valentine (07:39)

I think it depends on the individual that is very subjective. I've met several people that are like, you don't need an MBA. Just OJT, on the job training, that's where you'll get it. And I don't disagree. I do think that real world experience is directly applicable to running a business. If you've grown up in the business, you've had the family business and you have been subjected to HR, all the functions, then absolutely you don't need an MBA. I didn't have that and I didn't have exposure to paying federal taxes and state taxes and, you know, understanding unemployment and how those pieces work as well as financing the business, right? 

So I didn't have that coming out of college. So that's why I felt like I needed more training. And I would actually argue that for me, the MBA has been absolutely critical to understanding different pieces. When those come up, you know, I obviously don't do a ton of the accounting, I've got the CPA and bookkeepers, but at least I can speak the language I understand and we as a team work together to make sure that we're, you know, being proactive and managing it appropriately. If I didn't have the MBA, I think that would be more of a struggle. So for me, it's been critical, but again, it's not a one size fits all. I think it just depends on the individual.

Catherine Giese (09:09)

Yeah, that makes a ton of sense. So for you, you felt like it gave you like a really strong foundation and enough knowledge to be dangerous. It probably helped you ramp the business up a bit faster, I would imagine,

Tammy Valentine (09:21)

Totally. And I think that's actually been an advantage to us and the small businesses that we work with because I come at it from the business angle, but I've got the marketing background. So I can identify the gaps much quicker than individuals that are just coming at it from, you know, a marketing POV. So I think, having the best of both worlds has really kind of been a competitive advantage for us.

Catherine Giese (09:46)

Yeah, I think that's a really good segue into how you manage your finances. I know it sounds like you do offload some of it to an accountant. How did that kind of work? Like, you doing it yourself in the beginning? And like, what was that journey like?

Tammy Valentine (10:02)

Sure. So, uh, and you've kind of already alluded to like, how have I removed myself from different pieces of the business? And as we've grown, I've had to just let go and trust. We've got two bookkeepers that help. And then we've got a consultant that works within the advertising industry. 

And then we also have a CPA. So we have meetings, quarterly and just kind of talk through where are we, where's profitability. And then of course, what the next two quarters look like. And is there anything, are there any alligators in the grass? Is there anything that we need to be preparing for? So I always err on the side of caution when it comes to all of that. And it's been really awesome. And I really haven't had any issues. So as far as that piece of it, definitely, I do outsource it.

Catherine Giese (10:54)

Yeah, so it sounds like you work both reactively and proactively with them. So you take a look at how you're performing, but you also lean on them for business strategy. Is that true?

Tammy Valentine (11:05)

Yes. Yep. Especially like the more, you know, the, the managerial side. I love finance. I think it's fantastic. But in our business, we manage, lots and lots of dollars when it comes to media buys and those transactions will drive you insane just because there's so many. And, when you, multiply it by your full roster of clients and then some clients, you know, we don't recommend just Google ads. We recommend depending on the client, the target, all the budget, all those things for one client, we could be running up to four channels. So, you know, Google ads, meta, Tik Tok and Snapchat is what we would do for one, one client. I mean, times that by 30 and, the level of rec reconciliation will leave you up for hours upon end.

It took me a while to kind of get there, but it's super nice having folks that I can lean on and trust and they give me the right things so that if we need to make hard decisions or we need to pivot in a certain direction, we can, and we have the data to support.

Catherine Giese (12:13)

Yeah, that's so interesting. Your business is very unique because you are a marketing agency and that you're managing your budget for the business and you're also managing marketing budgets on behalf of the businesses that you serve, right? Yeah.

Tammy Valentine (12:26)

Right, right. And, you know, not to get too deep into that, but that can also go into like accrual versus cash versus unearned revenue. And that can be absolutely catastrophic when it comes to tax time. So it's managing that to where, you know, cost of goods and all of the transactions are booked appropriately is absolutely critical for a P and L.

Or various statements that are telling the truth, right? Because I mean, your data is only as good as what you put into it. There was a conference I went to a couple of years ago and the founder of JetBlue, he was on there and he said, what gets measured gets managed. And that's always stuck with me. So I feel that same way about, you know, the financial health of the of the business.

Catherine Giese (13:19)

Yeah, I actually would love to press more on taxes, because again, like as we were talking before, you mentioned that one of your biggest challenges in the beginning was taxes. Can you talk to us about that?

Tammy Valentine (13:30)

Sure. So I think, you know, being proactive, like there's different ways you can do it. And some companies, they wait till the end of the year and take care of it. Then we like to be proactive. So we manage it on a quarter by quarter basis. Just so that we know that's being taken care of on the federal level and the state level as far as employees and all of that, that's baked in, to overhead. so that part of it, you know, with our rates is how that's managed. But as far as like, federal and state, we meet and we talk about like, where are we, where are we going? And then two, what are the projections and how do we put ourselves in a good position to where at the end of the year we don't have a huge bill or a huge liability.

Catherine Giese (14:17)

Yeah, I love how proactive you are about taxes because that's like, it's such an important habit for people to have. I think a lot of new business owners sometimes don't realize that they have to pay taxes and they get stuck with a huge bill at the end of the year. It's nice to have an example of what a really healthy process around tax time is. Yeah.

Tammy Valentine (14:37)

It doesn't take a ton now that we've kind of got it streamlined, but I will be completely honest and say it's taken many years to get here and learn. I should have, I should have, I like to try to be as proactive as possible. And so I think that's, that's also a critical piece to this is just making sure that somebody's on top of it, driving it. And then, you know, for new business owners, it can be terrifying, but just lean into it and just know that you're not alone. And, you know, if you don't have the right answer to it, or you can't, deduce it based on whatever Google search you're seeing, then there's plenty of resources and other folks out there that have probably been in your same shoes.

Catherine Giese (15:25)

Yeah, totally. So I wanted to switch gears a little bit. You've been in business for 11 years, so you've seen it a lot. You've probably seen almost all of it. I also want to talk to you about hiring, because you now have a full team behind you. When did you first realize that you needed to hire?

Tammy Valentine (15:42)

I think when my cup first started to overflow and I was sitting there thinking, maybe I don't need to be reconciling all of these, media by receipts at, you know, one, two in the morning, perhaps someone else can help with that. Or I don't need to be the one that's responding on a Saturday morning to a client that's concerned about.

Whatever it is, like, perhaps I should have, you know, an account manager that's doing that or I probably shouldn't be the one that's over there creating, on-the-fly social posts. So I think it was just like those moments where I sat there and I kind of had a realization of like, are you going to continue to do this? 

Because if you are, you're headed straight towards burnout. And so it was that kind of, you know, level of shock, if you will, that I was kind of having with myself. 

And then, how do I hire? I think personality plays a big role on how coachable an individual is. Cause I'd like to think like I can bring on anybody and if they have a great attitude and they're willing to learn and really, lean into the things we're willing to teach them.

We don't have any problems. So that's a big thing. So personality can do attitude. We deal with a lot of online haters or people that can get really vicious, you know, on behalf of the clients, social media or whatever it is, Google reviews, we do some reputation management we see firsthand when the business owners get real fired up. 

And so, to tell the team, the beauty of our business is staying calm while the house is on fire. So, that's kind of an art. And then the other thing that I think is absolutely critical for anybody that's looking to do, to join our team is you have to listen with the intent to understand, and truly try to, you know, diagnose and recommend because there's lots of problems. Listening to our clients is a critical skill for success on the team.

Catherine Giese (17:52)

Yeah, that makes a lot of sense that you're optimizing for those traits. Marketing at scale is very emotionally arduous. So that makes a ton of sense. It sounds like there's kind of two main things going on for you on the business strategy side. When you really feel like you're reaching a point where you can't do it all. It's kind of a signal that you need to get someone in the seat. And then people wise, you're looking for very particular traits that would thrive in your particular environment.

Tammy Valentine (18:22)

Yes, ma'am. Yep. Absolutely.

We like to say we're, you know, a really tight work family and we take care of each other. We have each other's back. Then, rightfully so, that sounds funny, but like, you know, if somebody were to pick on one of my team members, I'm going to come in like a mama bear and you know, stand up for them. So I think establishing that balance between professions. We're very giving, but two, sometimes that can be ripe for abuse. So trying to really stand firm with this is the service and this is how we're willing to help. Beyond that, we're gonna have to figure something else out.

Catherine Giese (19:02)

Yeah, mean, protecting your team is such an important part of leadership. Kind of on the note of leadership, how did you kind of go from being that owner operator in it all the time to like elevating yourself out of that role and into more of a leadership role? What was that journey like?

Tammy Valentine (19:17)

I was very fortunate early on in my career to work for really terrible micromanagers. And I know what that's like on the receiving end. It's not fun when everything you do is being questioned and the rug is basically being pulled out underneath you. It creates not just a toxic environment, but very backstabbing. Like, you know, you don't trust anybody and when you micromanage people, it communicates to them that you don't trust them. And so I always kind of had in the back of my mind, if I was going to run my own business was to do the exact opposite. And so that's what I think I've really tried to do is just, get out of the way and just trust.

And, you know, if there's something that's big, you know, I'm happy to step in, but for the most part, really empowering people to be able to make decisions. And if they mess up and have a problem again, it says staying calm in the storm, or while the house is on fire, it's not biting their head off because they try to make a decision. It's more like, okay, you know, this is a learning experience and this is how we need to work through this. If this happens again in the future.

So I think people respond better to that versus, just being micromanaged and picked apart. So that's something I've really tried to come into was, just empowering folks and whether it's team members or contractors or even vendors too, and clients, it all kind of comes out, sometimes when you're frustrated or whatever.

I think as a leader, that's something that's critical is people will look to you for advice and that ability to just stay calm and neutral and not fire off when somebody's being ugly, think it's an important trait.

Catherine Giese (21:12)

For sure. And a good note that you can learn from people's mistakes just as much as good advice. I'm also curious, a lot of business owners hold themselves to very high standards of work. And I think a lot of times we hear from just people that we talk to that it can be hard for them to let go and delegate. And you kind of touched a little bit about coaching and allowing for those mistakes. How did you kind of navigate that yourself? Do you have any advice?

Tammy Valentine (21:38)

I think the big thing is empowering folks. You can do this without me. I trust you. I believe in you and I care about your success. and then following through with that, right? And keeping your word. If you say you're gonna do something, do it. So I think those things have been absolutely critical with that, no matter who you're dealing with. But that's really been, I guess, my secret.

Catherine Giese (22:06)

Yeah, so you just need to kind of buckle down and trust your team at the end of the day is what I'm hearing. Because you can't do it all. Yeah.

Tammy Valentine (22:12)

Yeah, I mean, the truth is that no two minds are alike, right? And people absorb information differently. And so it can be frustrating if you're as the manager having to repeat yourself and be like, I told you, this is how I want you to do it. 

But then like keeping in mind to like, you know, especially when it comes to hiring, do you want to be that person that's just working non stop? Every weekend because you can so and so didn't do it just like you? Or can you take a step back and just say, All right, like they didn't do it exactly like me, but we still got the high quality output, done. And that was their style. People like that I learned from too because I'm not like a master. I mean, I've been in this business for a long time, but there's always something to be learned.

Especially the new folks, and the young ones, like they always teach me stuff. And so I've just kind of learned to, back off, empower, and, you know, be their cheerleader. That's all they want. And it's the same thing that I kind of started with, with the mentors. Those mentors that I had really kind of took me under their wing and showed me they never got upset.

And they showed that they dealt with multi-million dollar projects. And so they really taught me like, this is how you stay calm when this whole thing blew up here and they were, you know, facing a potential lawsuit. And they said, you know what, that's okay. We're to work through it. And this is how we're going to do it. And to me, those things have always stood out. So that's how I try to lead.

Catherine Giese (23:43)

Yeah, I love that. It's so true that you don't have all the answers and that you can learn something from anyone. And really focusing on the output and the results more than someone doing it exactly the way that you do it is probably a good lesson for a lot of people to take away from that.

Tammy Valentine (23:59)

Well, and I just think that the output sometimes is better, right? Whenever new perspectives are embedded in it. So that part of it too has been good for me, you know, when I let go.

Catherine Giese (24:02)

Yeah, I totally agree with that. It's important to stay teachable yourself. You don't have all the answers. I do know also that you see a lot of businesses come through your agency doors. And so I kind of want to talk about lessons from them, like wins and missteps. But starting with the wins, what's kind of a common thread that you see with really successful businesses?

Tammy Valentine (24:37)

The owners managers kind of have that same style that I was talking about. So really believing in their team. They have strong core values. That's a big thing that I often see the owners are normally very humble and when they come to me, they're very, you know, how can you help us be better? And so I appreciate that. 

And then they either delegate or have someone help do the work, right? So there's not a ton of egos when it comes to some of the business owners that we deal with. They just wanna get it done. They just don't have enough time or energy to do it or the expertise. And so that's kind of where we fit in. 

And that's like how we vet whether or not it's a good client — when it comes to a group project, are they gonna show up and you know, put in their 10 % while we're putting in 90, or are they gonna not help us at all? So that's kind of how we vet whether or not they're a good fit. And other things that businesses do well on the win side is communicate. Oftentimes you hear that that's like a big thing in company cultures whenever they go to break or it's very toxic is

There's no open communication. feels like you're walking on eggshells when you try to provide feedback. I think communicating and being, you know, susceptible to feedback, and they're willing to take risks. I think that's another thing that I've kind of seen is, especially on the marketing stuff, because I can't prove to you what the ROI of that is going to be or the ROAS, you know, return on ad spend. 

I can't prove any of that at the beginning, it's a true trust partnership and I can kind of map it out as we build this thing together. But I think that that's a critical thing that I've seen on the wins with clients. 

Things that are maybe red flags that aren't a fit would be organizations that are so bureaucratic that they don't know that the left hand even exists from the right. And they're not willing to collaborate, communicate or be creative with problem solving. It's more like, this is our protocol. This is how we do it. And this is how we've always done it. You know, you need to fit into that. And so I think, we've struggled with organizations like that. kind of in that same vein organizations that have high turnover rate.

It's hard to build rapport with a manager or a group of managers whenever there's just, you know, you're constantly having to, to redo, you know, rebuild that rapport. So I'd say those are red flags when it comes to whether or not a client is a good fit.

Catherine Giese (27:19)

Yeah, that makes a ton of sense. I love all of the lessons that are coming through here, like that it's really more about attitude and people and the way that you show up. And it's really like you haven't really talked about hard skills at all with us. It's really all about attitude and showing up. And I think that's like a really important lesson to come through.

Tammy Valentine (27:38)

Yeah, I think that, you know, hard skills like statistical analysis and regression, all that stuff that can be taught. That's not that bad. But I think really, are you a fine person? Do people like interacting with you? You know, do they feel like they were heard? They were seen and heard when they had that interaction. Those are the things that I think are important. Cause I mean, at this point, I'm sure you can have some kind of AI tool do some of those things. But when it comes to humanizing a brand, I think that's where the true power lies.

Catherine Giese (28:13)

That makes a ton of sense. And that reminds me so much, some of our team last week was at Stripe Sessions, it's this tech conference, and Johnny Ive, one of the, you know, found, like, lead designers of Apple previously. Just his talk was about, like, making food for your team. It wasn't about, like, design at all. So that's really funny.

But I guess my last question for you, kind of on that, because you mentioned brand, a lot of our listeners, a lot of our customers are kind of just dying to know, how do I market myself? How do I get myself out there? What would be like, if you could sum it all up, know there's so many parts to it, what would be your number one piece of advice that you could give to them?

Tammy Valentine (28:55)

Ooh, okay. That's a great question. And let's see if I can give you some kind of reader's digest version. I think when it comes to branding, I would say don't be afraid to be humble, be authentic, and really take risks. Wayne Gretzky says, you miss 100 % of the shots you don't take.

Be willing to take risks and try different things. Some things might be sticky and some things may not. So it really just depends on your audience. It depends on your message, your delivery, right? And how you come about that. So I think the biggest piece of advice is, I say, don't be afraid to experiment and just take risks. At the end of the day you might not win but at least you're going to learn something and that's part of the journey. So that's probably the biggest piece of advice I would say.

Catherine Giese (30:00)

Totally, I love that. And things are always changing too. So like what worked a year ago might not work today and what didn't work a year ago might be amazing today. So yeah, I think that's great advice. Well, thank you so much for joining us. I feel like we learned so much from you about running a business, leadership is great, so many rich insights. So I really appreciate you taking the time.

Tammy Valentine (30:24)

Thank you. It was a lot of fun. I love conversations like this. I think open dialogue is important. And I think that, you know, there's just so much information out there that if I can help somebody in some way, I'm always willing to do that. So I really appreciate you, you know, having me on.

Catherine Giese (30:44)

Love it. Thank you.