LaSean Smith, Founder of Cagr Investments, joins the show to talk about how solopreneurs can increase their chances of success, the power of accountability, personal board or directors, and mistakes we’ve each made as solopreneurs. 

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LaSean Smith, Founder of Cagr Investments, joins the show to talk about how solopreneurs can increase their chances of success, the power of accountability, personal board of directors, and mistakes we’ve each made as solopreneurs.

Mark Struczewski  

I became a solopreneur back in July 2005 when the corporation that I was working for at the time said, You’re fired, you’re out of here”. And I’ll be honest, when I first started my solopreneur journey, I really thought, “Oh my goodness! I’m Jeff Bezos! Mark Zuckerberg! Private yachts, private planes.” 

But it doesn’t happen that way. Because when you work for yourself, you are everything. You are the president, the CEO, the marketer, sales, the janitor, the doorman, you’re everything.

LaSean Smith  

100%. And I think for some folks, they’re running from something. Solopreneurship can be the thing that helps them take control of their situation, but they still need a plan. You can be a bad manager to yourself as a solopreneur. So you have to work on that as well.


When you are your own boss, there’s no one holding you accountable. Unless you join an accountability group or you hire an accountability coach, you’re on your own. And I learned quickly that I needed help. I needed a coach that would call me out on my BS. I encourage everyone if you’re going to go on their own, or if you are on your own, you need someone. Not a friend or a spouse. You need to invest in someone who’s going to hold you accountable. Everybody can hold you accountable when things are going well. But when you have to call someone out on their BS, you need someone who will actually do it.


There’s a framework called the Personal Board of Directors (PBOD). You need to find two to three people in four specific groups: 1) advocates (connectors, people who open doors, influencers, sponsors), 2) developers (coaches, mentors, teachers, advisors), 3) innovators (people you dream with, disruptors, people helping you think out of the box, what could you tackle), and 4) supporters (cheerleaders, energy lifters, family, friends, peers). 

It’s okay for us to have some of those family members as our cheerleaders, but they have their own lane as supporters. And the more we decouple these roles, and have people in their own position, I find them more productive. I have folks meet with their PBOD every 90 days for 25 to 30 minutes. For anyone who doesn’t have a PBOD, I would say this is an incredible opportunity for them.


I feel that people don’t get me when I tell them that I’m a solopreneur. They look at me and cocked their head like a dog when they hear a high-pitched sound. “So you work for yourself, and what do you do?” Sometimes when people ask me this, I channel Tim Ferriss and tell people that I’m a drug dealer (I’m not!), because it’s so much easier than trying to explain to people what I actually do.


They definitely look confused. I think to a large degree, that’s projection where someone is thinking about themselves. And I’m not generalizing everyone. When I get the most extreme reactions, it’s someone who has allowed themselves to become a cog in the wheel. And so, in their brain, they think of their role. And then they think of the support structure around them, and they just can’t visualize how there can be a fulfilling professional path for someone who isn’t in that type of system. And that is the biggest unlock for me. 

I call myself a corporate refugee. I worked in massive big companies. And so I have a good handle on what it’s like to work there. I don’t look at it all as thumbs down, I hated those experiences, but I had a fantastic time. I knew when it was time for me to do something different and get back to my roots of working small. I’ve tried to kind of get rid of the bad habits, thinking everything has to be synchronous meetings, or other bureaucratic decision-making processes that you don’t need to have when it’s just yourself. But the flip side of that is once I jumped back into the solopreneurship field, I was like, I’m going to do marketing for 30 minutes, then a little delivery for an hour, etc. I was doing a lot of context switching and I realized I didn’t have a system that was going to lean itself to working by myself. And so, I had to reboot how I allocated my time to make sure I was focusing on what would move that needle versus sometimes the internal politics or the inertia of working in a large organization.


What are some of the mistakes that you made along the way as a solopreneur? We’ve already talked about two of mine: I didn’t think I needed accountability and I really thought there would be an instant success. I’m not rich like Mark Zuckerberg or Elon Musk. Of course, it depends on you define success.


I have shiny object syndrome. (Mark: Me too!). I really have to focus on finishing projects. And there are all sorts of ways to be a solopreneur. Some folks are in professional services while other folks may have an information product.

I come from the software world and I started coding very young. But software has evolved into this thing where large teams come together to build software and I have rediscovered kind of the joy and freedom of building small software now as a solo developer. And one of the things that are dangerous is all of the opportunities: AI, some new opportunity over here, or a friend has a real estate company, and they need this custom application to go do this thing. And so I really have to force myself to scope things properly to stay the course and finish. And that’s one of the things that I struggle with. 

When I left Corporate America, it was more acute because I was still working on the side doing small projects while I was working in Corporate America. But I always had the base of my job to bring me back to focus. 

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