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I share what I learn each day about entrepreneurship—from a biography or my own experience. Always a 2-min read or less.
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Entrepreneurship
Young Person’s Game
I recently heard someone refer to the start-up world as a young man’s (or woman’s) game. When I dug deeper, he shared that he believes you have to pursue this path young (in your twenties) if you want to be successful.
I don’t agree, for a few reasons. Anyone can be successful as a founder, regardless of age, if they’re willing to put in the work. How you achieve success will likely change with your age and maturity. For example, when you’re younger you can put working hard above most anything else. All-nighters, weekends—they’re doable. You can be selfish with your time. As you mature and have other priorities, you begin to work smart while working hard. The work ethic is still there, but how you deploy it is likely more strategic and incorporates other priorities.
History is full of examples of people having entrepreneurial success in their forties, fifties, and even sixties. Ray Kroc (McDonald’s in his fifties) and Harland Sanders (KFC in his sixties) are two great ones.
If you can solve a problem in a way that creates value, you can be an entrepreneur—no matter how old you are.
Now You Know . . . Now What?
A friend asked for my thoughts on accessibility of information, knowledge gaps, etc. Early in my journey, I didn’t know what I didn’t know, so I focused on acquiring knowledge about areas where I wanted to be successful (e.g., start-ups). That was helpful, but I realized it wasn’t enough. I had to take it a step further. I needed to figure out how to apply that knowledge. How do I apply it to my situation? How do I use it to achieve my goals? How do I execute given this new information?
Knowing what to do was helpful, but figuring out how to do it was a game changer because execution is what really matters. Knowledge is without a doubt valuable, but applying it is how you progress toward goals. I wasn’t always sure how to execute based on the knowledge I gathered, but I was determined to figure it out.
I ended up settling on two approaches. The first was to talk to experienced people who’d done what I was trying to do and ask how they did it. Dive into the specifics with them and get a better understanding of what worked, what didn’t work, and why. The second was to test. Come up with a few small things that have a reasonable chance of working and try them. Test them until I hit on the one(s) that work. Double down on what worked and kill the rest.
I still seek to learn and fill my knowledge gaps, but I also think about how to apply my knowledge and move the needle forward
Frustration Precedes Breakthroughs
I caught up with a founder recently and we talked about his frustrations. He shared that he’s been having a hard time the last few months. A laundry list of things aren’t going his way—from product, to customers, to managing his team. Some are the result of subpar decisions on his part. So many things aren’t going as he anticipated that it’s starting to wear on him mentally.
He asked my thoughts on his situation, and I shared my founder experience with him. On my journey, there was a pattern: when lots of things weren’t going right and my frustration level was peaking, I was usually on the cusp of a big breakthrough or material change in the business.
For example, we cut off one of our main suppliers because we weren’t aligned culturally. This caused us to start burning cash at a rapid rate. Tensions were high. We had some runway because of cash reserves, and I still believed in what we were trying to accomplish and in our team. Just when we were approaching max pain from cash burn, we identified a new supplier more advanced than our previous one. That situation set us up to go on a growth tear, and we scaled to eight figures in revenue.
When nothing is going right, be mindful that you’re likely on the cusp of a breakthrough if you push through!
Founders Aren’t Alone in Having a Harder Time Raising
I recently met with folks running an emerging fund who shared some interesting insights about their fundraise strategy. Their existing portfolio is performing well, and they’re out raising a new fund. They targeted $50 million, but because of recent market conditions they think they’ll land at $25 million. They’re adjusting the portfolio construction. They plan to do fewer investments and are raising the bar on what it takes for them to make an investment.
I wasn’t surprised to hear that funds are reducing the amount of capital they’re raising, given the macro environment, but the higher bar for investment was surprising given the success of their investments.
Risk aversion has ballooned, and founders should be aware of this and plan accordingly. We’ll eventually move back to embracing more risk, but I believe that will be a gradual process.
Quality Transcends Macro Headwinds
I chatted today with a friend who’s in a different industry. I enjoy talking to people outside of start-ups and tech for a different perspective. Our conversation naturally touched on the current macro state. He shared something interesting: in his industry there’s always demand for quality, regardless of what’s going on in the world. People putting out a quality product aren’t affected by the macro environment.
My buddy makes a great point that founders should be mindful of. If you’re solving a problem with a quality product that creates value for customers, customer demand will be there. And with authentic customer demand comes the potential to build a large company—you will be able to get capital from investors to scale.
Focus on quality and things will likely play out in your favor, even in a questionable macro environment.
Nonobvious Opportunities
Some solutions to problems that have the biggest impact on our lives seem obvious once we’re using them—though not before. Summoning a stranger to pick you up in their car or renting a room from a stranger both seem unremarkable now that we’re doing both. But a few years ago, they were nonobvious opportunities that many thought had no chance of succeeding. Uber, Airbnb, and a variety of other impactful solutions have changed how we live our lives and are each worth billions of dollars.
Evaluating a nonobvious opportunity for investment is hard. It requires investors to focus on what they stand to gain if things go right, not all the possible reasons for failure. And before investors can evaluate these opportunities, they have to find them.
I suspect that more nonobvious opportunities from great founders with the potential for outsize returns exist, but the network problem in VC prevents them from being funded. If this problem can be solved, I see more solutions being built that will have a material positive impact on society and create outsize returns for the limited partners that back these founders.
Get to Know People with Goals Like Yours
Had a great chat with an investor today. We discussed why some founders struggle when they transition out of big organizations. He shared an observation with me: Employees working at larger companies who don’t have founder friends but want to be a founder tend to focus on working hard at work. They miss the mark on building an outside network—so, when they start their company, they don’t know anyone who can help them.
As I listened to this investor, I thought about my early days as a founder. I quit a job in a big company, only to realize that I didn’t know anybody who was building a company. It felt like I was the lone man on an island. I eventually sought out other early startup founders, we formed a cohort, and my trajectory changed completely.
If you aspire to building a startup, start seeking out people who are building companies or who support people building companies. They will be instrumental in helping you navigate the entrepreneurial journey.
Resist Comfort
I watched an interview in which coach Mike Tomlin described how he stays at the top of his game. After winning two Super Bowls, he still has the same fire he had when he first became an NFL head coach fifteen years ago. Tomlin shared something that really stuck with me. He resists comfort. In fact, he tells his team, “Don’t seek comfort,” because special outcomes—outsize outcomes—are the result of being uncomfortable. He explained that he views thinking back to his success as a Super Bowl champion as seeking comfort. So, he ignores his past success and the comfort it breeds.
Tomlin may ignore his track record, but it’s impressive and speaks to his credibility as a coach and leader.
Growth often comes from being in uncomfortable situations. You’re forced to think about and do things that are unfamiliar. Succeed or fail, you’ll learn from those experiences. I really like how Tomlin is intentional about resisting comfort. It tells me that he’s a learner and constantly looking for ways to improve himself and the team he leads. It makes sense that after fifteen years, he’s still at the top of his game.
If you’re aiming to do something special, consider asking yourself, “Am I resisting comfort—or seeking it—when I make decisions?”
Innovation Isn’t Just Tech
I was talking with a buddy today about his business. He shared how his solution works. At its core, he’s bringing together existing pieces to create a new solution. What he’s doing is highly complex. As we chatted, I thought: This isn’t a tech company, but it’s still innovative.
Innovation is the introduction of something new. The new thing doesn’t have to be driven by, or be, technology. In the case of my buddy, he’s taking pieces that already exist and combining them in a new way. Even though these pieces are readily available to everyone, no one has combined them the way he has. His innovation is in how he’s combined the pieces and managed the complexity of doing so.
He likely doesn’t think of himself as an innovator because he isn’t building a tech company, but he is an innovative founder.
Innovation doesn’t happen only in tech. Anyone can be an innovator if they solve a problem in a way that hasn’t been seen before. Even if it’s just combining existing things in a new way.
Who in Your Circle Is Doing Amazing Stuff?
I was sharing my journey with someone this past week. I said that a critical part of it was meeting other early-stage founders and forming an accountability group of sorts. The person I was speaking with probed a little about why that group had such outsize influence. The answer was that the group wasn’t just talking about starting companies, they were taking action. And not only were they acting, they were executing at a high level. The results spoke for themselves.
Looking back on it, I can see that being so close to smart people doing amazing stuff was transformative. They showed me what was possible and made me push harder for what I wanted. I didn’t want to get left behind by my peers, so I leveled up.
My takeaway is that finding other entrepreneurs whom I could relate to was helpful—but finding the ones doing great things was positively transformative. Being in the presence of people doing amazing stuff increases the chances that you’ll do amazing stuff too.
Who in your circle is doing amazing stuff?
