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This is your destination for feeling empowered in building your business.
These are the real, raw stories of entrepreneurs and business owners who have built their businesses through the messy middle of $1-20 Million, hosted by serial entrepreneur Matt Tait.
Matt knows what it’s like to scale past the first million, and on this show he’ll be bringing on other serial entrepreneurs and business owners who have been there, done that (or, are currently in it) to share what’s worked, what hasn’t, and what’s next.
Matt Tait [00:00:00]:
As we look back at these core themes that we've explored on After the First Million, risk and resilience, personal growth, balancing work and life, company culture, scaling, these are all important things. But if there's one takeaway, it may feel like you're alone in this journey, it may feel like a solo journey, but it's really not. You are constantly learning and growing and figuring out how to make it through that messy middle. I'm Matt Tait, founder of Decimal and fellow entrepreneur. Yes, I'm one of the crazy ones. I've chosen time and time again to hustle my way through that first million. Now I'm scaling to the next 50, so I know firsthand what the messy middle is really like. And I know that entrepreneurs and leaders like us need a destination for empowerment, community, and encouragement.
Matt Tait [00:00:50]:
This is our place. This is After the First Million. Welcome back to After the First Million. I'm Matt Tait, the host, and if you have been with us for the whole season, you know that we've had some pretty amazing conversations with some really, really cool leaders and really successful people. I have been just blown away in my first season of recording any type of podcast at just the openness and good storytelling that we've been able to witness this year. And as we end the year, as I come up on just thinking through the whole journey that we've gone through, I thought it would be really nice to revisit some of the biggest themes that we've covered this year, maybe even share some sound bites from our guests with some key insights on risk and resilience and leadership and work, life, balance and culture and all of that stuff. I thought it'd be really cool to just review it together. So before we get started, there were some key themes that I think stood out as a thread through all of our stories.
Matt Tait [00:01:59]:
And as an entrepreneur myself, I recognize in my own journey and in Decimal's journey, so many of these themes themselves. And I thought it'd be cool to just share them up front and then we can walk through them really quickly. So, first, the theme that I think stands out, number one, is that risk and resilience are a key part of entrepreneurship. Risk is something that we, as leaders and entrepreneurs, we embrace, but resilience is also a key part of it. Failure is a big part of what we do. Testing things, trying new stuff, understanding what it's like to get knocked down and get back up. Risk and resilience are key. Number two, leadership and personal growth.
Matt Tait [00:02:39]:
I think so much of me personally growing up in A family of entrepreneurs. I didn't understand that leadership also involved growing as a person. As your company grows, you have to change and grow with it. You're not static and neither is your company. I always joke with business owners and sales leaders all the time that go to market fit is a moving target. So is the personal growth that's necessary to run a business. So leadership and personal growth.
Matt Tait [00:03:07]:
Number three, balancing work with personal life and mental health. We as leaders and entrepreneurs, it's our job to pour ourselves into our company, into our clients, into our team. If we want to be able to truly do that every day, we have to fill our own cup. We have to figure out what it means to focus on ourselves, to give ourselves a certain measure of happiness and mental health and whatever it is that gets us going. But that's a really important aspect. A lot of times I tell people it's okay to be selfish sometimes. We hear that a lot in these stories. And then, number four, building and maintaining a company culture.
Matt Tait [00:03:47]:
It's a really hard thing to do. It's been even harder for us at Decimal being remote only. But it's hard for everybody, particularly if your company is growing rapidly. But in general, maintaining and building a good culture requires an intentional focus on what that is, what you want it to be, what your values are, how you live out those values, how your team lives them out, how it exists in interpersonal relationships, client relationships. That intentionality is something we hear a lot about with successful people. And then finally, navigating growth and scaling challenges. So number one, risk and resilience and entrepreneurship. Two, leadership and personal growth.
Matt Tait [00:04:27]:
Three, balancing work with personal life and mental health. Four, building and maintaining a company culture. And then five, navigating growth and scaling challenges. So risk going with this, the first theme, risk and resilience and entrepreneurship. Risk is what we do. We as entrepreneurs are crazy enough to start a business. We have crazy ideas that we think we can do it. We want to be the boss, we want to be the leader.
Matt Tait [00:04:54]:
We want to convince people to jump off that bridge. It’s what keeps you in the game. But as many of our guests share, those risks come with failure. They come with finding the courage to fight through the tough times to understand that it's not always going to be perfect and it's not going to be easy. First up in this story is Tiffany Sauder, CEO of Element Three. She shared, I think, an amazingly powerful story of going through one of the hardest periods in her business where things got tough and she learned about resilience along the way.
Tiffany Sauder [00:05:30]:
We ended up getting through it, but it took us, like, probably 18 to 24 months to pay everybody back that we owed money to. I paid every dollar of interest, and it was, like, humbling and brutal. And I cried a lot. And that was where my dad said to me, hard is not the end. It's just hard. And if you want to quit, it can be the end. But it doesn't have to be.
Matt Tait [00:05:55]:
All right, there's Tiffany's clip. It's an amazing story. Next.
Matt Tait [00:06:00]:
I think it's really cool to hear about Dagan Xavier, co-founder of Label Insight, as he opens up about his mission to help others believe in their ability to tackle hard things. His story isn't an easy one, but it had such a cool ending, and I think it's an amazing story.
Dagan Xavier [00:06:19]:
Isn't that the coolest thing, though, mate? Trying to share that with other people that you can do hard things, that's the addictive thing for me. It's like, I believe I can do hard things. Now, imagine this world if everyone believed that they could do hard things. And so I almost feel like it's like, my duty to get stuck in and instill that belief because I think it's done wonders for me.
Matt Tait [00:06:43]:
All right, and finally, here's Devin Bramhall, former CEO of Animalz, as she shares, I think, an extremely amazing, powerful story of personal resilience, even as it applies to work.
Devin Bramhall [00:06:59]:
That goes back to not needing to be liked. I became a much more effective leader the less I cared about being liked, because that's not my job. Actually, in some cases as CEO, it's my job to be the bullseye, because you're ultimately the one taking responsibility. And so if you can get comfy with that, I think that's when I started to see myself more as a CEO than I ever felt in the beginning.
Matt Tait [00:07:29]:
Okay. Our second theme is leadership and personal growth. Entrepreneurship is not just about growing a business. It's about growing who you are as a person and understanding that as your company changes, as times change, you also have to grow. And for many founders, that means learning a lot about themselves. It means truly looking in the mirror and seeing what you're good at, what you're bad at, and then having the strength to go find people that complement your skill set.
Matt Tait [00:08:01]:
So first we're going to hear from Rich Hagberg, who I have to admit, is my personal CEO coach. He is an amazing CEO whisperer. He also is the founder of the Hagberg Consulting Group and soon to have a pretty popular book coming out on leadership. And Rich has coached hundreds and hundreds of CEOs and entrepreneurs and leaders. And he's learned that understanding one's leadership style is essential to becoming an effective leader.
Rich Hagberg [00:08:57]:
There are essentially three styles of leadership. The visionary evangelist, like Jobs and Musk, the relationship builder, like John Chambers and Howard Schultz of Starbucks and Jamie Dimon, and the manager of execution, you know, like Jack Welch, organized, orderly, structured. And when we could assess that and other things, it was really helpful to people to know what their style was.
Rich Hagberg [00:08:59]:
A typical founder is high on visionary evangelist, medium on relationship, and low on execution. And that's their Achilles heel.
Matt Tait [00:09:09]:
All right, next, and continuing the coaches theme, we have Adam Weber, former Chief People Officer, who explains why leaders need to allow time for their teams to process big decisions and to get on board with this. I talk a lot at Decimal about socializing decision making. Very rarely do I go into a big all hands meeting and make an announcement that most of the people in that room haven't already heard before. It's so important to give people time to absorb new things and to give them time to process.
Adam Weber [00:09:43]:
I think oftentimes CEOs and leaders of companies forget when they're making a big decision that they've had like months to ruminate on the decision, and then they enact it and then immediately are frustrated that everybody else isn't like just jumping out of their seat, super excited about it, even though they had no time to ruminate. And like, that's really common where it's like, I'm really frustrated at my team because this thing that's obviously the right decision.
Adam Weber [00:10:09]:
And it probably is. It's just that how do you actually get people on board with your vision, with this thing that you've really thought about? And how do you give them space to process too?
Matt Tait [00:10:20]:
And lastly on this theme is I think one of the coolest guests that we've had, Sims Foster, co-founder of Foster Supply Hospitality. And he describes how connecting with the local community gives his team a deeper sense of purpose in their work. His is such a cool company, such a cool story, and I'm really glad that we could share his clip here.
Sims Foster [00:10:43]:
It's much easier to get through that messy middle when you care so deeply about not just your business, but its relationship to where it is and the people around you. If the mission is bigger, it carries more pressure, but it also carries you through.
Matt Tait [00:11:03]:
All right, number three, moving on to balancing work with personal life and mental health. I talk all the time about how as a successful leader, you need to be and understand that being selfish is okay.
Matt Tait [00:11:15]:
Taking time to focus on your mental and physical health. Trying to find a coach, somebody that you can pay, to give you feedback, to be honest with you about what's going on and what you're doing and how you're even communicating with your team, I think is essential. Finding a peer group, a group of people going through what you go through, it gives you a sense of community in what can a lot of times be a very lonely and isolating role. So building a business, as you know, can be all-consuming. But a lot of us today, I know for me personally, I focus on being a really good boss and a really good leader, but it's more important to me to also be a good husband and to be a good dad. It's a lot of balancing. I fail and struggle at it all the time, but I think a lot of people try to walk that balance, and it's really important to be intentional about it. We had a lot of guests this season that talked about how they struggle with it, how they balance it.
Matt Tait [00:12:13]:
First up is Kevin Bailey, CEO of Dreamfuel, and he talks about the importance of mental resilience that leaders need to cultivate and keep growing under the constant pressure of the role.
Kevin Bailey [00:12:27]:
These athletes, yes, they're under a lot of pressure. We are also under a ton of pressure. It's all relative. Everything we have is on the line. When we found these companies and the psychological challenges we face, to be able to deal with them adequately, I believe needs some expertise. So, sure, we coach a lot of executives, we coach a lot of leaders, coach a lot of founders, but we have a concentration in discipline and mental performance. And, yeah, people like Nick Smarelli and John Speer, I mean, they've had exits and they're great executive coaches, but they understand the true value of having a genuine and deep understanding of performance, performance, psychology, and neuroscience, and gives an edge to allow us to help people get through the incredible psychological hurdles that you face on these journeys.
Matt Tait [00:13:10]:
All right, next we have Lindsay Roselle, founder of MotherLoad Co, who supports achieving mothers as they balance the ambitions of family and work. Like, it's okay to want to be good at everything. I think so many times it's easier for us dads and working dads to balance. But working moms, I think, are truly amazing. And I would be remiss if I did not call out Sarah Tait, who is my hero and wife for doing the exact same thing. So let's hear Lindsay.
Lindsay Roselle [00:13:42]:
I'm so aware of wanting to be a good mother and wanting to break some of the patterns that my mother had and her mother.
Lindsay Roselle [00:13:47]:
And I don't want to lose myself to motherhood. Like, I still want to be Lindsay. I still have ambition. I still want to go do things in the world and help people. The reckoning really woke me up to, okay, how do all these things play in life? You know, because I have a finite amount of time, I want to do both of these things well. And the only way I'm going to be able to do any of that is just to be honest with myself and with the people around me that I want both things. And sometimes one is going to take precedent over the other, and that's just going to have to be okay.
Matt Tait [00:14:19]:
All right, next we have Jeremy Reymer, a good friend of mine who is the CEO and founder of DriverReach, which is a software company that helps in the trucking industry.
Matt Tait [00:14:30]:
And Jeremy's really cool, too, because in all of this balancing, he also works with his wife, which, personally, my wife would kill me if we worked together. It's very good that we're able to balance by not working together. But Jeremy and his wife Wendy do an amazing job of working together. And this isn't their first company doing it, but they talk a lot about risk tolerance and family balance and kind of how they. How they work together to really achieve that balance themselves.
Jeremy Reymer [00:14:59]:
And fast forward a few years. I ended up having the opportunity to buy that company. Not a great time in the market, if you remember the wonder years of the Great Recession.
Jeremy Reymer [00:15:08]:
You were taking on some risk. But I felt like it was calculated. I knew that we'd get through this. I knew that nothing fundamentally had changed. We just got to hunker down through that period. I mean, it was tough. Don't get me wrong. We're in the midst.
Jeremy Reymer [00:15:20]:
I've got children, number one. I've got a family to protect and take care of first and foremost. You gotta protect your family.
Matt Tait [00:15:27]:
All right, finally we have, I think, one of the ultimate podcasters ever. Lindsey Tjepkema is the co-founder and former CEO of Casted. And it's really cool to watch her reflect on, as she calls it, and I agree, the unique superpowers she gained from balancing work with life as a parent. She even had some really cool stories during the pandemic of her kids being under the desk with swords as she's trying to do fundraising calls and be all serious and. I don't know. Life's messy, and it's cool to talk about it.
Lindsay Tjepkema [00:16:00]:
I truly think that there's something about being a working parent, being a working mom, especially being a working mom of twins, that gave me superpowers. And I was just like, okay. While they stayed in daycare the whole time. I was like, there's no way. I'm not going to do this while they're home. There's literally no way. So they stayed in daycare.
Lindsay Tjepkema [00:16:18]:
And I knew that I had to make a certain amount of money to kind of keep things going. And I had a very limited amount of time while they were all in daycare. I just did the thing.
Matt Tait [00:16:28]:
All right, moving on to theme number four. Building and maintaining a company culture. This is a theme that hits particularly close to home for me. It is such an important thing. Just yesterday, I was able to interview a brand new employee.
Matt Tait [00:16:42]:
She's 30 days in at Decimal, and she was talking about how it's a remote team, yet she feels so supported. She feels like she has a team that she's working on that communicates well that she understands the values of do the right thing and being transparent. And 30 days in, she already gets it. That is such a cool thing. Culture is such a big focus for me. And with Decimal being a remote company, we have to be so much more intentional about it, but so does everybody. And this theme and hearing all of our guests kind of talk about it in various ways is such an important thing. And, you know, to me, culture isn't a buzzword.
Matt Tait [00:17:27]:
Culture is what makes great companies. It's the foundation of what keeps everything together, that helps teams grow. And to hear our guests and how they approach building and maintaining a strong culture was really cool. The first guest that I think is super cool to hear from is Nick Smarrelli, as he discusses the importance of a structure and organization around scaling and how that affects culture.
Nick Smarrelli [00:17:52]:
We needed process, we needed structure, and we needed discipline. And we just had all these things that we never had in the earlier phases that made it real. And we needed meetings. We were no longer like the fun little company that never had meetings.
Nick Smarrelli [00:18:07]:
Like, we had meetings and we had dashboards and we had scorecards and we had. We were just, like, becoming everything I never thought we had to be, but we needed to be in order to scale correctly. And that was a transition for us.
Matt Tait [00:18:18]:
All right, next we have, like, the queen of culture. I mean, literally her company, Confetti, Lee Rubin. They do events for our company. Like, they are all about events that help embrace culture and fun around work, and particularly in a remote environment where that can be harder. It's really cool to hear her talk about the importance of finding the right partners and building trust.
Matt Tait [00:18:38]:
We are in this alone. And that doesn't just mean our team and our family. That means the partners and vendors and all the people and companies that support how we operate is really essential.
Lee Rubin [00:19:15]:
One of the challenges was that I didn't really have the support that I wanted. But finding a technical co-founder was my first really, really big challenge. Because I got so many mixed feedback, I realized that I needed someone with very strong communication skills. When you meet a lot of engineers, you're like, okay, some of these people have that strength and some of them don't. And actually, like, very few have very good communication skills.
Lee Rubin [00:19:15]:
And that became a priority for me is like, if I'm going to go down this journey, they don't just need to be a technical genius, but they need to be a fabulous communicator.
Matt Tait [00:19:26]:
All right, next we have Michael King, the founder of KFE Solutions and The CFO Accelerator. And you're going to hear this really cool aha moment that he had about company culture and how it. It's not just a buzzword, but it actually affects the business that you run and can help you be more successful.
Michael King [00:19:46]:
It's so important to me and to the DNA of my team that we are around folks that have that growth mindset. And it's not even just team, it's vendors and it's clients. It's who we allow to speak to us. Because I think that if you surround yourself with people that have the growth mindset, it helps propel you. If you have people around you that don't believe in that, that have more of that scarcity mindset or limiting beliefs that will also impact your trajectory in your future as well.
Michael King [00:20:17]:
So we are pretty relentless and obsessive about wanting to be around other people that have that mindset.
Matt Tait [00:20:20]:
All right, finally on culture, I think a really great shining example is Chad Peterman. What he and his brother are doing running Peterman Heating, Cooling and Plumbing. This is a company that has grown and scaled in a. I would say, in an industry people don't think about as, like, running cool companies or just a beacon of what people think of when they think of culture. But what Chad and his brother and his family have started and run, it just explains how having a supportive culture in their case helps a family business thrive. And he is such a cool example. And here's his clip.
Chad Peterman [00:20:55]:
We developed this philosophy. It's been a few years now, but a lot of people in the home services industry will place their external customer above their internal customer. And we said, well, if we flip that on its head, because at the end of the day, our external customer is probably going to get better service from a internal customer that really loves where they work, is bought into the culture, bought into the values. I don't know that we could have scaled it on the fact of, like, hey, we're going to be technical. Technical. And not place an emphasis on the culture and what we're building and where people work and where they call home.
Matt Tait [00:21:34]:
All right, moving on to our final theme, which is just navigating growth and scaling challenges. Scaling and growing a business isn't easy. Things change. You're constantly chasing a moving target and you're trying to learn new complexities and skills and strategies, and you're going to fail a lot. And that's okay. But also being willing to listen and be humble around it is so important. Brian Powers, former CEO of PactSafe, recovering attorney just like me. I think it's really cool to hear him discuss the concept of repeatability and scaling and how important that is.
Brian Powers [00:22:09]:
The tech startup blogosphere is obsessed with the word scale, right? The key to any scaling anything in a business is just finding veins of repeatability and then figuring out how you repeat the things that are working and eliminate the things that aren't.
Matt Tait [00:22:22]:
All right, next we have Mark Caswell, former CEO, Resultant. This is a company that just took off like a rocket ship. And at some point, Mark looked in the mirror and he said, you know what? It's not for me anymore. I don't want to take it to the next phase. But he got it so far. And to hear him talk about the need for processes as teams grow, as those of us that are entrepreneurs that start our own company, process is one of the things that we rebel against the most. But at some point, you grow and you realize the process is essential to growing as business. You have to have it. So here's Mark.
Mark Caswell [00:22:58]:
We sold the business 21 months later. It went well for them. We grew the business approximately 4x over that time. Opportunity came our way and we didn't really have to create a lot of structure and process and discipline to do that. 21 months of growth. And if you don't have to, you tend not to. And so we just didn't create a lot of that structure.
Mark Caswell [00:23:22]:
Well, then we sold the business again, which was hard and fun again. But right after we closed with that, what we realized is like, this next phase of scale, it's going to require a lot more diligence. It's going to require a lot more structure, a lot more focus. It felt like in the course of, like, three months, we just, like, became a different business. And the type of leader I had to be in that was, like, totally different.
Matt Tait [00:23:46]:
All right, next we have Sharon Rechter, co-founder of First Media. Like, you want to talk about a super cool company, billions of impressions. Like, just about every woman in the entire country has heard of the brands that she puts out there.
Matt Tait [00:24:00]:
And she shares her perspective on staying agile and the agility with which her company and they have transformed themselves multiple times over the last few decades is astounding. But she talks about staying agile and adapting to both big and small challenges and how that's fueled her growth. So let's listen to her.
Sharon Rechter [00:24:22]:
Sometimes the growth comes from worse change, and sometimes it comes from really small opportunities that you need to listen to and take a chance. Again, it's adjusting to change. We have been able to keep growing and stay a profitable company at big scale by constantly accepting the change and following the money.
Matt Tait [00:24:49]:
All right, and now to close, here's Steven Plappert, co-founder of Forecastr and the lessons he learned. And I can empathize with this. As somebody whose first company failed and who is now finding a lot of success.
Steven Plappert [00:25:02]:
FantasyHub was my first big piece of adversity where, hey, this thing you put everything you had into, you put everything you know you had and it failed, and you're walking away with nothing, so to speak. In a lot of ways, as I think a lot of entrepreneurs do, first company or otherwise, your identity gets tied up in the company. You know, it's difficult to separate Steven Plappert from FantasyHub. When that company failed, you know, I felt like a piece of me had died. I put everything I had into that company for three years. So I think that was the hardest thing, was just coming to terms with this thing that you poured all your heart and soul into for years. You made so many sacrifices, and you're walking away, not with nothing, right?
Steven Plappert [00:25:38]:
Once you get the perspective, you can say, well, I had all the learnings and I'm just like you. I'm so grateful for that experience. I wouldn't change it for anything.
Matt Tait [00:25:45]:
So there you have it. I have felt truly lucky to have the opportunity to interview so many amazing people. Personally, this has been worth it for me just for those conversations and the notes I've been able to take and what I've learned from it. I hope that all of you have also been able to take something that has helped you to improve your business, or at least to feel less lonely. As we look back at these core themes that we've explored on after the first million risk and resilience, the personal growth, balancing work and life, company culture, scaling.
Matt Tait [00:26:17]:
These are all important things, and each guest brought a truly unique perspective. But if there's one takeaway, it may feel like you're alone in this journey, it may feel like a solo journey, but it's really not. There are lots of people that are out there and there are lots of ways to learn, and I think that's one of the greatest parts of this job. You are constantly learning and growing and figuring out how to make it through that messy middle. So I want to thank all of you who listened for all of your honest thoughts and insights, all the guests for coming in and being open and transparent. And here's to the next million. Thanks so much for listening. After the First Million is presented by Decimal.
Matt Tait [00:26:57]:
To listen to more episodes and find tips to help make running a business easier, visit decimal.com/afm. Want to join the conversation? Reach out to me on LinkedIn and let's explore the messy middle.