I had several side hustles as a kid. Mowing lawns, selling CDs, selling automotive parts, washing cars, selling bailed hay . . . I was always down for a side hustle. I even worked 12-hour days building houses one summer and earned a cool $125 a week (yes . . . per week). A friend recently asked me what motivated me at such a young age.

The driver was wanting independence. I vividly remember my parents telling me they wouldn’t buy certain things for me. Their reasoning was solid. We weren’t rich. Money didn’t grow on trees. I needed to earn the expensive things I wanted. My parents controlled how money was spent (and rightly so because they worked hard to earn it), which meant my buying decisions depended on what they’d allow.

I hated this dependence. It felt suffocating. I was limited because my funds were limited. I decided to start doing things to earn money and reduce my dependence on my folks. To their credit, when they saw what I was doing and why I was doing it, they encouraged me. They didn’t try to reassert control (even though I was still living under their roof). They told me I could do whatever I wanted with the money I earned, with a few exceptions.

Disliking feeling dependent and doing what I could to break away from it led me to entrepreneurship. The more I learned about entrepreneurship, the more I saw it as the path to a life of independence (and not just financial independence).

I caught up with a founder recently. He’s started several companies. He’s got one running smoothly, with a management team installed. He’s got another off the ground and is currently installing the management team. Even with all this, we talked about new ideas he wants to pursue.

This founder is a zero-to-one person. He gets energy from taking something from the starting line to the end of the first leg of the race. He isn’t the person who’ll finish the rest of the race. He wants to get things going and put the right people in place to win the race. The idea of taking an idea and turning it into something—not living the entire journey—excites him.

When he’s asked why he doesn’t keep running his companies himself, his explanation is simple: He gets bored working on the same thing too long.

Entrepreneurship is a choose-your-adventure journey with lots of ways to achieve success. This founder is a good example. He’s founded several successful companies, taking them only from zero to one. After that he’s let other people capable of growing beyond one take over. He’s happy watching the companies he founded from the sideline while he incubates his next big idea.

I listened to an interview of Scooter Braun recently. Scooter has had a wildly successful career in the entertainment industry. He’s credited with discovering Justin Bieber, and he managed several other top entertainers. He recently sold his firm, Ithaca Holdings, for $1 billion and acquired Quality Control, one of the most successful rap labels—which happens to be in Atlanta—for around $250 million.  

Braun shared advice he’d received from Jeff Bezos, founder of Amazon.com, on work–life balance. Bezos thinks you shouldn’t have to balance two things you love and that harmonizing them makes more sense. To do this, he communicates to people in his personal life how much he loves what he’s doing at work and what the latest developments there are. At work, his team knows how much he loves his children and what’s going on with them. The idea is to integrate and harmonize your work life and home life by making everyone feel in the loop, part of what’s going on in the parts of your life they can’t see. If you must miss a work event because of something child-related, everyone understands because they’re in the loop and know your children take priority.

Braun went on to share that for many years he kept his work and personal lives very separate but cared deeply about both. This ultimately created issues in his life because, as he put it, “it was like being married to two different people,” which wasn’t fair to the important people in his life.

I’ve been more of a balance person historically—I tend to try to keep work and my personal life separate. Sometimes it’s worked and sometimes it hasn’t. The advice Braun received from Bezos definitely resonated with me. It has me thinking about sharing more about the important parts of my life with people who are important to me. I’m naturally a private person, so I want to harmonize in a way that feels comfortable, given that trait.

Here’s the clip of Braun sharing what he learned from Bezos and how it affected him.

A few years ago, I shared the following thoughts in a post:

During economic expansions most entrepreneurs accept a certain level of inefficiency in the name of growth. They’re trying to move as much water as possible from point A to point B. They know water is slopping out of the buckets because they’re moving fast, but as long as more water is pouring into the tanks at point A, it doesn’t matter. But during economic contractions, the same entrepreneurs embrace efficiency. The water source dries up, so they put lids on the buckets and carry them slowly to make the most of the water they have.

Companies of all sizes have gone from making their priority growth (sometimes at all costs) to making it free cash flow (or a path to it). Growth is still important, but at a more measured rate that minimizes water slopping out of the buckets. This signifies a shift to an efficiency mindset.

Many companies can’t magically start operating efficiently. They need help getting there and will search for solutions to help them. Software that empowers them to do things they can’t do manually or to do things more consistently and efficiently will be in demand.

I see demand for workflow management software increasing and entrepreneurs building these solutions. Solutions that solve painful efficiency problems in the right way could be poised for explosive growth.

I’ve spent time working on understanding the journey of emerging investment managers. These people start companies that make money by investing capital. I think of them as entrepreneurs who happen to be investors, or “investor entrepreneurs.” I’ve been curious to learn how the most successful emerging managers are wired, so I started studying managers who’ve had outsize success over a decade or more. This means they’ve been able to compound their capital at an annual rate that exceeds benchmarks like the S&P 500. I started with venture capital fund managers but expanded to studying managers in private equity, real estate, hedge funds, value investing, and other areas.

Studying several managers who’ve compounded their capital at above-average rates in various ways has been enlightening. It’s shown me that the ways to have success as an investor vary widely. But I’ve noticed a trait that these successful managers have in common: a burning desire to approach investing in their own unique way as opposed to a way mandated by someone else. They wanted to develop, test, and refine their own investment approach. They saw starting their own firm as the best path. A few worked for other people, but that was never the goal—it was a stepping-stone. The goal was always to invest using a unique insight and control their own destiny as an investor.

I chatted with a friend who’s in the process of acquiring a business. Instead of using a bank to finance the debt portion of the purchase price, he’s using seller financing. That is, instead of taking out a bank loan and paying the full purchase price in cash, he’s accepting a loan from the seller. The seller gets paid part of the purchase price in cash at closing, with the remainder repaid over time with interest.

This is common, but I hadn’t heard about it being used as much in the last few years because interest rates have been so low. I was curious how the seller felt about it, so I asked my friend.

He said the seller envisioned selling the business, getting cash in a lump sum, and riding off into the sunset. Seller financing, which prevents a clean break from the business, wasn’t part of his vision. It took a bit of convincing by my friend, but in the end, they made a deal after a detailed walkthrough of the math.

Riding off into the sunset is every founder’s dream scenario if they want to sell, but it doesn’t often play out that way. Things like earnouts and seller financing are common and can mean the seller will get delayed payments over a period of time.

I was chatting with some people about thinking in probabilities when a friend quoted Jeff Bezos, Amazon’s founder. What Bezos said is well known, and people reference it all the time:

Given a ten percent chance of a 100 times payoff, you should take that bet every time.

This statement didn’t sit well with me. I decided to get more context. I found the original shareholder letter in which Bezos said this. Here’s the entire paragraph:

One area where I think we are especially distinctive is failure. I believe we are the best place in the world to fail (we have plenty of practice!), and failure and invention are inseparable twins. To invent you have to experiment, and if you know in advance that it’s going to work, it’s not an experiment. Most large organizations embrace the idea of invention, but are not willing to suffer the string of failed experiments necessary to get there. Outsized returns often come from betting against conventional wisdom, and conventional wisdom is usually right. Given a ten percent chance of a 100 times payoff, you should take that bet every time. But you’re still going to be wrong nine times out of ten. We all know that if you swing for the fences, you’re going to strike out a lot, but you’re also going to hit some home runs. The difference between baseball and business, however, is that baseball has a truncated outcome distribution. When you swing, no matter how well you connect with the ball, the most runs you can get is four. In business, every once in a while, when you step up to the plate, you can score 1,000 runs. This long-tailed distribution of returns is why it’s important to be bold. Big winners pay for so many experiments.

Given the full context, we can see that Bezos is talking about experimentation and the resulting outsize value it can create. He’s thinking about the probability of success and the potential value created when deciding whether to do something experimental.

This isn’t a concept that everyone can grasp. I think his comparison of baseball to business is powerful. The comparison communicates the potential to create value by solving problems in a way everyone can understand.

Creating value for others by solving their problems isn’t easy. It’s a journey of trial and error until you hit upon a solution that will get you a thousand runs.

Howard Marks is a successful billionaire investor who cofounded Oaktree Capital in 1995. As of today, Oaktree has over $170 billion in assets under management, more than 1,000 employees, and offices worldwide.

Marks is known as a shrewd investor and for sharing his insights on financial matters in widely read memos since 1990. It’s said that many notable investors, including Warren Buffett, look forward to reading these memos.

I recently watched an interview in which Marks shared an interesting fact. Between 1990 and 2000, he didn’t receive a single response when he sent out his memos. Utter silence. People didn’t even acknowledge receiving them. But Marks continued to write them. After more than a decade, people began paying attention. Thirty years later, his memos are highly anticipated and widely read.

Marks’s memos are a great reminder that good things don’t always happen overnight. Marks put in consistent work for over a decade before his writing efforts began to pay off.

As an early founder, I thought about when (not whether) things would stop going well at my company. It was a bit of founder paranoia, which sounds crazy but is healthy and common (only the paranoid survive). It didn’t mean my behavior changed. It meant I was aware that continued success was not a given and had to be earned.

As I’ve reflected on this more, I’ve realized that there was something deeper in the back of my mind that was more personal. Since high school, my trajectory had been mostly up and to the right. Most of the things I tried, I succeeded at—some minor hurdles, but no material failures. I was appreciative of but also concerned by this trajectory. I couldn’t put my finger on why, but I can now.

Success isn’t indefinite. It’s cyclical. Anyone who has achieved outsize success has also experienced a setback or major failure. Said differently, they’ve experienced highs and lows, or a cyclical journey.

At CCAW I was pushing for more success, but subconsciously I was bracing for an inevitable setback. As crazy as it sounds, that mindset ended up being helpful.

I didn’t know when failure would happen, but I knew it would happen. So, when I encountered a setback, I wasn’t surprised. Instead, I looked at it as a necessary part of the cyclical journey to success. I wasn’t thrilled by the setback but made sure to look for the positives in the situation. I focused on identifying what I could learn. I tried to figure out how what had happened could position me for a bigger win. That mindset helped me navigate the setback and come out on the other side better positioned for bigger things.

My big takeaway from this is that I can be a serial entrepreneur, but my success will be cyclical. Said differently, serial entrepreneurs have cyclical success. I will try things, and some of them will fail miserably. Instead of thinking I’m winning or losing, I now view it as winning or learning.

I caught up with a founder who’s been trying to sell his solution to customers for months. It’s gaining traction—but more slowly than he would like. With his current monthly burn rate and cash on hand, he has less than a year of runway. He realized he likely wouldn’t reach breakeven before his runway ends, and raising more capital from investors is far from certain, so he decided to try something different.

At the end of his pitch, he began asking his prospective customers if they would buy his solution if he repurposed it to address a few pain points they’d mentioned. The response has been overwhelmingly positive. The pitch meetings went from maybe we’ll try this to, yes, we want to buy that. In the same meeting.

It’s early, but the response is night-and-day different, according to the founder. He spent months building a solution that sold slowly. Then he began giving out one-pagers on his new solution, and prospective customers are ready to sign up. He went from begging for follow-up meetings to customers asking for follow-up meetings within three days of the initial meeting (two meetings in one week!). He went from trying to convince customers to pay for a solution to customers offering to pay in advance.

It’s early and a lot could happen or not happen, but this founder has likely hit on the painful problem that could lead to product–market fit. Product–market fit is hard to define, but when you have it or are getting close, your customers will let you know with their wallets.

The prospect of running out of money has been scary for this founder, but it looks like it could have been the spark that led his company to early signs of product–market fit. The team is focused on building what customers want instead of what investors want to hear.