Scaling With People
Tired of spinning your startup wheels but never gaining traction? Buckle up, founders and CEOs, because this podcast is your rocket fuel to profitability! Every week, we ignite explosive conversations with bold-faced founders, brainy experts, and even a few out-of-this-world vendors. Get ready to crack the code on growth, master employee engagement, and blast through your scaling goals. We’re talking real-world strategies, actionable tips, and perspectives that’ll make your business do a cosmic dance. So, strap in and prepare for lift-off!
Scaling With People
Your Team Isn’t the Problem. Your Leadership Is. with David Miller
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
The fastest way to stall a growing company isn’t bad strategy. It’s treating people like “soft stuff” and trusting the numbers to tell the whole story.
In this episode, David Miller breaks down what actually compounds in small business growth—and why most founders avoid it. We get into the uncomfortable truth behind energy, trust, and culture, and how ignoring them quietly slows everything down.
David shares the moment he realized pure grind wasn’t sustainable—and how shifting to energy management and mental discipline changed how he leads. We unpack his “inside-out leadership” approach, why busywork feels productive while killing momentum, and how taking control of your calendar protects the work that actually drives growth.
On the people side, this gets even sharper. We talk about hiring and rewarding based on earned trust, using core values as a real operating system—not wall art—and how to spot early signs of culture breakdown before they cost you. David also explains how to quantify the true cost of a toxic employee—and why your best people won’t tolerate misalignment for long.
From an investor lens, we go inside the signals that show up in the first 3 to 90 days, how outside capital changes team dynamics, and what it actually means to respect capital when you’re building for the long term.
If you’re building a company where people—not just numbers—decide the outcome, this episode will change how you think about growth.
Follow the show for more conversations on how founders actually scale without breaking—and share this with someone who’s feeling the pressure behind the scenes.
Show Promise And Format
SPEAKER_01Welcome to Scaling with People, your weekly playbook for turning chaos into compounding growth. Each week we go under the hood with battle test experts in all areas of business, from marketing to sales, operation finance, and people, plus product and leadership, to unpack the plays, numbers, and systems that turn chaos into compounding growth. Learn straight from founders and experts who've done it and continue to do it successfully. There's zero fluff, just moves that you can still immediately. This podcast is brought to you by Guide to HR. Human expertise, AI-powered impact. Welcome everyone to today's Skilling with People Podcast. I'm Guinevere Aquari, your host and founder and CEO to Guide to HR. On today's episode, we love leaders who've seen the whole movie, not just the highlight rail. Today's guest, David Miller, is a 2X CEO, angel investor, and two times exit founder with over 20 years in the SMB trenches. He's built companies every way imaginable, bootstrapped, venture-backed, and everything in between. But here's the twist. He argues the real drivers of a value in a company are the things most founders struggle to measure. That's people, trust, culture, leadership. If you've ever wondered how to gauge the human factors that actually make or break a business, this conversation is going to get home. Well, thank you so much, David, for joining us today. Uh, before we get started, do you want to tell the audience a little bit more about yourself? Because that is a very impressive uh resume you got.
SPEAKER_00Well, thanks for having me, Guinevere. It's uh a pleasure to be on here and spend some time with you. Uh yeah, just kind of a really short, short snippet. It is I I love the small business space. Uh I love the spirit of small business. I believe it's the the heartbeat uh of America with at least from a business standpoint. And it it is it is so over um in a lot of other countries that I found as well. Just how much um output is created in the economy that that comes from small businesses. So I've been in a lot of different industries from finance to cannabis, fashion, beauty, and all that. And um, so it's it's really about the space of being in small businesses and how do we as entrepreneurs, small business owners uh effectively um, you know, grow our businesses in the in the in a healthy way.
Burnout Wake-Up Call From Shingles
SPEAKER_01Yeah, I love that. I sometimes when I'm traveling, I will just go down streets and look at the business names, and it just fascinates me how many businesses are out there that you just don't even know exist. There's just so many, so all these small businesses. So I do think you're right, we are the foundation of our country, that's for sure. So when you've built companies through bootstrapping and raising capital, you've had two exits. What did each path teach you about people and leadership that founders potentially often overlook?
SPEAKER_00Well, I think probably one of the biggest like eye-openers for me was around 2017. I remember I was at the beach with my family. Uh my business was growing like crazy. We were number fastest growing financial services company on the on the ink list that year, or maybe the year before. And you know, I needed a much deserved at what I felt like vacation.
SPEAKER_02Yeah.
SPEAKER_00And I got shingles on that trip.
SPEAKER_01Oh dang.
SPEAKER_00And you know, typically shingles is something that people get um later on in life.
SPEAKER_01Yeah.
SPEAKER_00And that's when I really said, okay, like I've I've got to work smarter, working harder. Um is definitely part of the equation, but it's but it's not all of it. So that that was probably like the moment where I'm like, all right, I need I need to retool how I'm actually working, um, because I'm spinning tires here in a way that's that's just not not helpful for anybody.
SPEAKER_01And not scalable too over time, I'm sure.
SPEAKER_00Yep, yep.
SPEAKER_01Yeah, yeah. So what did that look like? I mean, if we were gonna dive in and people resonate with that, okay, great, yeah, I totally get it. Uh uh, but how do I start? What does that look like? What did that look like for you when you realized you had to kind of reenvision how you work?
Energy Discipline And Daily Practices
SPEAKER_00Yeah, I mean, it was really, really difficult. Um, one, because you know, I've been operating and been successful and doing things in a way for the past, I guess it was 10 years as an entrepreneur, and then all of a sudden I knew I needed uh to recalibrate. So I um ran into through entrepreneurs organization uh Hindi priest, Dan DePonty's his name, and I got a lot of, I guess you could say, woo-type practices through him and how to really focus on uh discipline and and calming your mind. And there's a lot of different ways for people to like manage their energy and be efficient. Uh that that qualitative component, whether it's meditation, you know, whether it's yoga, whether it's um all the different types of um heuristic things that that you can do, just framing your mind and building that discipline is is the big thing. Because I I meditated for I think five years straight every day, um starting around 2018, but I don't meditate anymore. And what I'm not that meditating is bad, I think it's wonderful, but like what it did teach me is like how do I need to focus my mind. Um, and now when I wake up, the reason I don't meditate most always is because my mind's already in that state. I don't need to calm it and recalibrate it because I've built that discipline up um over a lot of different things. So, yeah, I think just energy management is is the biggest thing when it comes to scaling a business and and how do you you know accelerate to the next level.
SPEAKER_01I so resonate with that. Uh, the last year I've been really spending time figuring out where I should be spending my energy. And a lot of people may be thinking about that's your time. But I would say it's not just time, right? You could spend your time doing something that like actually re-energizes you. And so then you could spend it doing it for five hours and go off and be able to run a marathon versus something that really depletes your energy and you do it for 20 minutes and you want to go take a nap for half the day, right? So like, and and you know, I mean, I tell people this, they never believe me. I'm an introvert, I call myself a functioning introvert. So when I do things, even like this podcast, I can't do a bunch of them because I'm ready to go take a nap for an hour and a half after a podcast because I'm like, I need to re-reinfuse my energy. So I love the concept because it is, it's not again, it's not just about the time. It's how how your you your body actually interacts and engages and and uses your the energy in those minutes you're spending on the time.
Inside-Out Leadership Quadrants
SPEAKER_00Yeah, I I agree there, Guinevere. And to your to your point, um, when it when it comes to like managing your energy and just giving blanket advice, I think that can be very dangerous because, like you said, everybody's different, whether they're introverted, extroverted, ambiverted, all the different types of people. How do you see the world? How do you feel like the world sees you? Then it's different for everybody. And I had an article posted in Ink magazine maybe like a month or so ago, and I created something called uh inside out leadership. And it's how do you balance thought versus action? And that is that is really, really helpful from a business standpoint, whether you're driving numbers and systems, kind of like the logical type side of it, or whether you're you're driving those qualitative or intuit uh intuition um based type activities. And so how I what I had was I had basically four quadrants. And if like if the y-axis is uh thought and the x-axis is action, then you have you have those four boxes. And so that top box is really where you want to be, which is high thought or do thought, I should say, giving stuff considerable thought, um, and being decisive. That that's the space we could we all want to play in, you know, whether you're introverted, extroverted, whatever type of person you are, um, just when it comes to effective leadership. But if you move over a little bit and you just stray away, I you you're anxious, you get stressed, um, you go through a short-term struggle and you're not thinking straight, you know, you have low thought, sorry, not low thought, you're not giving stuff due thought, but you um but you have a high level of action. Well, if you have high level action and you're giving stuff too much thought, sorry, not enough thought, then that's that's when people spin their tires.
SPEAKER_01Yes.
SPEAKER_00That's whenever um, you know, they're they're just checking boxes for that dopamine hit, for lack of better words. It's great if you journal. I journal every day. Um, the way I've done it has changed over the years. But when I first started out, oh, you know, I'd have a list of 10 things I wanted to accomplish. And the way that our what I've found is the way that our mind works is like our mind will naturally go to what do we think we can finish the quickest and get that done. So if we have 10 things on there, but the one thing maybe it's only like 30 or 45 minutes worth of work. It's the most important. Our mind may push it to the bottom because we know we can get all this other stuff.
SPEAKER_01Yeah. So that makes so much sense. And the satisfaction, like dopamine you were talking about, like that satisfaction of checking that box off. Like, I know until like, I don't know, a couple years ago, I was still handwriting. So I could physically check that box off. Uh, you know, I've kind of changed more into digital, but it's the digital is just not enough dopamine hit of checking the box off physically, but I totally get what you're saying. And and I've even tied that into like calendar ownership too. Like I always talk about don't let your calendar be your be. Like you need to be that, right? Like, don't let it control you. You need to control your calendar. And I've actually structured it where now all my means are color code coded. And as a founder, business owner, what's my top priority? It's sales and marketing. I need to find more people, more clients. That's my top priority, which is yellow on my calendar. And I look every week at the beginning. If there's if if yellow is not the primary biggest meeting event, I I re-change my calendar because that everything else falls away, right?
SPEAKER_00Yeah. Yeah. The time management piece is something I'm still improving on every day.
SPEAKER_01Oh, me too. Me too. Like I have a way, but like then I fall back in my old habits. So yeah, that's totally uh it's uh it's hard. It's it's hard to change your habits. So let me ask, when you look back at your companies um on the on the people side, what people decisions had the biggest impact on your success or failure?
Hiring And Rewarding By Earned Trust
SPEAKER_00Uh for me, the people decisions are making hiring and rewarding employees, making those decisions based on intuition, based on your gut, based on earned trust over time. My best, most loyal, most productive employees have been those that are loyal, are trustworthy, you know, that have that gut feeling of, hey, this this is gonna work out. And I feel like people sometimes it's really easy to get lost in the details or the neocortex part of your brain, that thinking brain. Your brain will lie to you in so many different ways just to get people to avoid things that might be difficult. And you throw that in with the human elements, it's it's and emotions, it's difficult to navigate. So just really going with your gut when it comes to people.
Measuring Team Health Beyond eNPS
SPEAKER_01Yeah, okay, that's good to know. I mean, there are, I will say there are some founders out there who are not necessarily got a good solid gut. So be careful on that for some of the listeners. But I, you know, if you know you have a good instinct on people, that's uh that definitely is where I thrive at for sure and what I do. So I love that answer. Um, kind of going into more of a measurable of like the intangibles of people, like people, it's one of the things I've seen with some founders is they they're so frustrated because on the HR front, it's really hard to get the kind of metrics you get from like sales and marketing, right? Sales and marketing is very number specific, but when you talk about people, you talked about emotions, the culture, those kind of things, it's hard to really quantify that. Um, and and but you know, founders love metrics. So uh when it comes to people, how do you actually measure the health of your teams? How have you done that in the past or even currently?
SPEAKER_00Um, of course, you got the you know, ENPS scores and and a lot of a lot of those type standard things that that companies have. And I'd, you know, as long as you got the systems and the scope, it then I would recommend, you know, at least looking into that. But one of the things that um really stuck with me is I don't know if it was Sherm or one of those other HR organizations, that in combination with really understanding the book Who Not How by Dan Sullivan was understanding how to quantify using a lot of data the impact that that people have. And what they found was is that the individual's salary, you know, is a direct corollary to the impact they're making in the organization. Not that someone with the lower salary can't make a large impact and vice versa, but um the as far as their job responsibilities and what they do for the organization, yeah. Let's say you have somebody that has a$50,000 salary. Well, what that study found was is that they can impact up to seven times as to what they're doing for the organization. Now think about that. If they're a toxic employee, then that's$350,000 that they're harming your organization as opposed to$350,000 where they're driving impact in a very um in a positive manner. And you know, it it may be, hey, it's they're sucking resources and time from an A-player that you have, and you're never gonna see that. Or they are you know causing communication breakdown between your team, they're just not getting stuff done and stuff falls through the cracks. So they kind of the nuts and bolts of it was that they took all of this data and kind of amalgamated and said, hey, this is on average what what the employee impact is. And I think if people understand that and they believe that, then they can really start to see how to measure employees, you know, based on those, you know, not so measurable factors.
SPEAKER_01Yeah, it totally makes sense. And I've had experience where, you know, uh back in the day when I was in corporate land, uh a CEO and I, we were talking about an individual. And I I came to and I said, look, we've got to get this person, we gotta let them go. The amount of distraction that they are doing, that's more harm, like you said, seven times more harm than good. And uh it was really hard for this founder to process and actually take action on because this was an early entry employee who had, you know, blood, sweat, and tears over months and years to help the business grow and thrive. But now he's become a liability. And I probably pushed this founder, I'm gonna say I feel like probably more than nine months to like let this person go. And then we finally did. And literally the next day, I had so many people at my door telling me they were so they were amazed that it happened. They never thought that we were gonna let this bad apple go. That what's the point in working so hard if this person is still here? There's no ramifications for being a bad employee and all this toxic things that were happening. And the moment we let them go, it was like we just let this breeze come through our culture of fresh, freshness, and everyone kind of just got rejuvenated. That, like, oh, we are actually going to support the people who are the high performers and you know, celebrate them and get rid of those lower performers. And it like was a night and day difference. And usually it doesn't work that fast, but in that situation, I think it was because the founder took so long to actually take action that people just didn't think he was ever going to be fired.
SPEAKER_00Yeah, it's almost like a breath of fresh air across the organization. And yeah, you can feel it when those types of decisions are made. And, you know, like kind of like you said, the high performers, they, you know, they'll they're focused, they're hardworking, they're loyal, but you know, they'll only take so much.
SPEAKER_01Yeah, exactly.
SPEAKER_00They'll they'll be gone if if if if the environment becomes filled with people that, you know, they don't they don't have similar type work ethic and values.
Core Values Hiring And Culture Warnings
SPEAKER_01Yeah. So that's a great uh lead, Lee. My next question for you is what do you see as being some early warning signs that a founder can see in regards to team culture leadership structure? Um where it might be breaking down or might be like, hey, we got a bad apple, let's get rid of it before it taints the whole tree.
SPEAKER_00Gosh, I mean it's different for every situation. Like I think having a really solid hiring process um and incorporating your company's core values into that process and making sure that you're asking questions without saying what the core value is so they respond and see how that maps over. You know, that's what we did after we instilled a Kaizen Lean type hiring process with my first company. Because before, you know, we had just hired people, we got luck really lucky on some and not so lucky on others. But that having your core values is like what you reward people, you know, what you want people to, you know, how you want them to think and act and um and what they what they talk about has a lot to do with that. And if different strokes for different folks, right? If if they don't align with your core values, that's okay. They just need to go find another organization where they do.
What Investors Notice About Founders
SPEAKER_01Exactly. Yeah. I always say core values is so important. And I feel like sometimes like core value and culture and all kind of like, you know, buzzwords and people are like, whatever, like I that's not gonna impact my productivity or my revenue, my profits, but it does because it's the foundation of how you're telling people what they can expect from you and what you expect from them. When they walk through the door, it's it's like the communication foundation of like how we're gonna interact and engage with each other. And like you said, different folks for different stripes. I I look at it like some organizations are all about like, you know, the cutthroat cells, you know, the best salesperson wins and they're gonna step over everybody. And that's the kind of culture we want, right? Versus the more like we're a team, we're a family culture. Like it's two different things. And I have hired salespeople on in both uh in both cultures. And to not hire the right people, they flounder. Like they just like they realize that that no, I need that cutthroat to be successful to push me along or oh no, this is way too intense. I can't handle that. I like the more we're gonna support each other kind of culture. So it yeah, just because the person isn't a right fit for you doesn't mean they're not gonna be an amazing fit for some other company out there. Uh so yeah, I uh I also think like, you know, you like you talked about the EMPS score, some other metrics you can look at, also just having a good ear to what's going on, the pulse of your business, because you can start to pick up on some like, you know, grumblings and maybe some smart out statements here and there. And and having managers that are really listening and paying attention and and sharing what's happening in the org can also be some good warning signs too. But it takes it takes a mindful thought to like be present and and really like gather that information to go, okay, I think the wind is going to start shifting and I need to take care of that before it happens. Yeah. So um, you know, if you walk into a company as an investor, you you're an angel investor or even an advisor, what signals about people and culture do you look for in the first three to ninety days?
SPEAKER_00Uh I mean the the founder, how they're interacting, the type of energy that they give off, the the soft unspoken verbal, non sorry, non-verbal communication that employees say about the founder whenever you're having conversations with them, and really understanding that like that founder's vision, and this is why one of the many reasons I have such a strong belief in the power of small business, is that founder's vision, you know, is how was you know, was the birth of the company. And you know, it may not be clear and it may even need to be refined, but like that good faith that they put forward, that risk that they put forward, casts out across the organization ways that a lot of us don't understand, and that I don't often. Obviously, I don't fully understand either. So really like understanding what the foundation is of the company, like at its ethos, having a good gauge for that is the main thing that I look for to see if uh I I've invested in companies where I had no idea what the heck they did. But I had such a good feeling about the founder and her capability that I mean they grew to well over a hundred million dollar company when I invested them when they were, I think maybe at a three or four million dollar valuation.
SPEAKER_02Wow.
SPEAKER_00You know, I I that's placing your bet on people, right?
SPEAKER_02Yeah, yeah.
SPEAKER_00I didn't claim to have any expertise in that industry. I knew I didn't, but I'm like, this girl is passionate, she knows what she wants, yeah. There's conviction around it, and you know, I'm I'm gonna bet on that.
Respecting Capital On Both Sides
SPEAKER_01I love that. That is true. I mean, especially when the uh businesses are younger, it is all about the founders for sure. And I know you have experience both in V venture-backed and bootstrapped companies. How does capital change the people dynamics inside of a company from your experience?
SPEAKER_00I think or does it? Yeah, uh the capital needs to be respected on both sides. And when the capital's not respected, then there's there's most likely going to be problems that that affect the company uh at a material level. Meaning that if you're given capital from an outside party, like knowing what that capital is, is is an extension of trust. That capital has expectations around it. And don't take something that obviously we can't control our outcomes, and you want to be careful how you deal with setting certain types of expectations, and they want to be done fairly. But like if someone gives you capital, then that that needs to be respected as a founder, as an employee, you know, maybe as a co-investor. Uh, and then on on the other side, you know, the the people that are investing in the company, like they the the investors, they they need to understand the employees. They need to understand the vision, they need to embrace the vision, they need to help the founder better articulate his vision if it's not already communicated across the organization. So being able to like just respect capital both ways, human capital and money, um is probably the biggest disconnect that I've experienced, um, negatively and positively in companies I've invested in, um, but also that I've seen on the outside in publicly traded markets as well.
SPEAKER_01Yeah, I had one founder who I think he respected it so much that it actually froze him in making really good, like betting money, like solid, like I'm gonna take this risk, but it's like I know the background behind the risk and spend this money in a way that's gonna grow my business. And he would like, he'd make the bet, but then before, like, you know, the ball gets put in the little spinny roulette thing, he pulls a bet off the table and he just kind of goes back and forth. And it, I could I just like the impact it had on the business. So I kind of want to dive in a little bit about what you mean with by respect, because you were saying that, and I like got a little triggered by watching this founder do that. Like, is it respect just like, look, I understand the money's coming from here, and it's I already have a plan on how I'm going to use it and then execute on that as the best as you can. Or can you maybe define what you mean by that a little bit? Because I got triggered when you said that.
SPEAKER_00Yeah, for sure. Yeah, that's that's a great, great clarification point. So, like a real world example is uh colleague of mine, so I won't mention name or company, but you know, he he received outside capital. Um, they were probably like a$10 million company at the time, uh tech company. And he got, I think the injection uh was about a million dollars. And a year passed, and that million, you know, they had a plan they wanted to execute on it. They knew they needed to scale, uh, but at the end of that the first year, they didn't touch any of that million dollars.
SPEAKER_01Oh, yikes. Okay.
SPEAKER_00And and that that's how you it and it's different in every situation. But he this gentleman respected the capital that he was given. He could have easily burned it and invested it even more so, but they started growing in ways they did not expect um because the market turned. So they didn't need to use the capital. They could have, they could have found ways that it would have grown even more.
SPEAKER_02Yeah.
SPEAKER_00But now that conversation a year from now, he's having a he's talking with the investor, and it's like, hey, we didn't use any of your money, and we were still able to achieve well beyond what both of our expectations were. So now the trust that he built with that investor was was tenfold what it would have been. Um so yeah, that's that's what I mean. And it again, it needs to go both ways as far as respecting capital, the human capital and the money capital part of it.
Exits Legacy And People-First Buyers
SPEAKER_01I know. I was actually just talking to somebody, it kind of translates to government, like they have their budget and they have to use it or they're not gonna get that much or more the following year, but they don't need to use it, but they're forced to use it in order to get a good budget the next year. And that that is not respecting capital, in my opinion, right? Because it's like, you know, okay, great, we'll we'll uh we'll order another round of cocktails to pay, you know, to spend the money or whatever the situation is. That's a silly analogy, but you know what I mean. So I I appreciate the clarification on that. Um, as we wrap up, I'd love to ask you a couple questions about exiting. Um, in your experience, like, do you did you see that you the buyers, when you were exiting and selling your business, did they care about culture and teen quality as much as the numbers? And what did it look like in regards to the people side of um the value of of the buy for the buyer?
SPEAKER_00Gosh, uh so I've exited in several different ways. Um you know, if if it wasn't about the people, then then it wouldn't have then it wouldn't have happened. I wouldn't have sold to the people that I'll that I've sold to. And you know, whenever and I think as an entrepreneur, like we're the only ones that can truly get that because we're selling our sweat and blood equity that we have, and it's it's really hard to one, just put a number to because the check doesn't make you feel better. Maybe maybe for a day, but you know, knowing that you're you know, two, three, five, however many years have passed, and your business is still run by a solid individual, they're taking care of the employees, that it's it's become greater than you and it exists past you is you know, is something that um I think that it's one of the reasons as entrepreneurs we grow and sell businesses is to make an impact in that way.
SPEAKER_01Yeah, and have a little bit of a legacy too. Well, David, as we wrap up here, uh any final thoughts or tips or tricks you'd like to share with the audience?
SPEAKER_00Um gosh, I can't think of any off the top of my head other than just work your ass off, but work your ass off in in a very balanced way.
SPEAKER_01Yeah, yeah, I love that. And um, I think you know, we were talking earlier, you wanted to share um you know how you get a hold of you and that you would like, you know, offer um a couple minutes of people of your time for anyone that has further questions.
Offers Resources And Final CTA
SPEAKER_00Yeah, yeah. People are just free to DM me on Instagram, davidmiller.buzz, or there's probably there's a contact me um tag on my website, which is alchemyascale.com. Happy to happy to talk to any small business owner. Um, no strings attached, and I mean that from the bottom of my heart. If they if they're have a certain struggle, I'll spend 10, 15, 20 minutes with them and say, hey, you know, this is uh this is maybe a nugget that that might help you get over this this mistake that could be avoided.
SPEAKER_01Well, I appreciate the offer and audience. I hope you take him up on it because he's got some really great experience and knowledge that he can share with you to help you get unstuck and help you scale your business. So, David, thanks so much for joining us today on this podcast. And for the listeners, we'll see you on the next one. Have a great one, everybody.
SPEAKER_00Thanks for having me.
SPEAKER_01That's a wrap for today's episode of Scaling with People. If you got value from this conversation, do me a favor, share it with someone building something big. And hey, I'd love to hear your take. Drop a comment, shoot me a message, or start a conversation. And don't forget to subscribe so you never miss the bold, unfiltered strategies we drop every week. I'm Gwynabre Quary, founder and CEO of Guide2HR, where we help high growth companies scale smart with people for strategies and AI powered systems that don't just keep up, they lead. If you're building fast and want your HR to move faster, head to guide2hr.com and let's talk. And remember, scale isn't just about speed, it's about people. Until next time, have a great one.
