A few months ago, I started thinking about what traits founders/CEOs who take a company from idea to public-market company worth billions possess. It’s a small group of people, as the number of companies that reach hundreds of millions or billions in annual revenue is small relative to the total number of companies founded.

After spending time learning about people who’ve accomplished this, I see one clear trait. These people were obsessive about a single problem. They weren’t entrepreneurs who wanted to build a company but weren’t sure what problem they wanted to solve. Rather, they’d been thinking about a problem intensely and decided they wanted to solve it.

It's hard to scale a company to billions and take it public. Along the way, founders will usually get an offer to sell if the company is doing well. To reject the offer and the financial windfall associated with it and take a company public is a hard decision. To continue as a public-company CEO and endure all the scrutiny from public-market investors isn’t for the faint of heart, either. This requires a vision and level of commitment that founders aren’t likely to have if they weren’t obsessive about the problem they’re solving.

I’ll keep looking as I study more founders/CEOs of public companies, but I’ve yet to find a founder of a public company who was a founder in search of problem before starting their company.

Mark Twain is known for saying:

“History doesn't repeat itself, but it does rhyme.”

I was chatting with a friend about this quote, and he added something that stuck with me:

“The reason history rhymes is because human nature doesn’t change. People don’t change, but circumstances do.”

That’s why knowing history is important, he said.

I’m no history buff, but I do enjoy reading historical accounts of major business events and the journeys of people who achieved outsize success. I consistently read the latter and randomly read the former. This year, I want to be more intentional about identifying important events in business and monetary policy history and reading long-form content to better understand them and decisions related to them. Hopefully this will help me see patterns in human behavior that will help me understand and navigate similar future events.

I was chatting with a friend about this quote, and he added something that stuck with me: “The reason history rhymes is because human nature doesn’t change. People don’t change, but circumstances do.”

That’s why knowing history is important, he said.

I’m no history buff, but I do enjoy reading historical accounts of major business events and the journeys of people who achieved outsize success. I consistently read the latter and randomly read the former. This year, I want to be more intentional about identifying important events in business and monetary policy history and reading long-form content to better understand them and decisions related to them. Hopefully this will help me see patterns in human behavior that will help me understand and navigate similar future events.

During a meeting with an entrepreneur, the topic of unique work styles came up. He has a long track record of success, so I was interested in hearing about his approach. He almost burned out early in his entrepreneurial journey and realized that he’s a sprinter, not an endurance entrepreneur.

He learned that he isn’t wired to run hard 24/7/365. Instead, he’s more effective when he goes all out for a while and then recovers before repeating the cycle. He’ll work intensely for a few months and then take two or three weeks off to rest and recover. Recharging and recovering are key to how he operates best. He comes back refreshed, energized, and full of new ideas.

He went on to share that the key to this working style is his productivity when he’s in work mode. He works intensely—so much so that he’s able to get more work done during his sprint than most people would accomplish during his sprint and recovery period. He essentially gets the same or slightly more work done in a year, even with his breaks, than people who don’t take these kinds of breaks do.

He isn’t the first person to share this type of work style with me. I know a successful angel investor who focused intensely on investing for three or four months and then took a month or two off to recover and travel. He could do this because he was investing his own capital, so he could deploy it at a pace that suited him. He too works intensely when he’s in work mode but needs time off to recover.

Sprinting as a way of working isn’t available to everyone, but for those who are intense but not wired for endurance, it’s a work style to consider.

Today I listened to a podcast on which the guest talked about her research on focus. The gist was that it’s getting hard for people to focus for more than one minute (yes, one minute!) while we’re working because of all the distractions we’re inundated with. That one-minute figure was based on a study she’d done over a few years. I knew focus was a problem, but the one-minute stat was surprising.

My college had a Center for Academic Success. Sadly, most students never used it. Honestly, I don’t think many people even knew it existed. Serendipitously, I met the center’s director my first semester, and she impressed me. I told her about my heavy course load that semester, and she urged me to visit her center. When I took her up on her offer, I learned study techniques that proved invaluable. A lot of it was about habits that help you focus. I’ve always been able to focus on things I’m interested in, but the things I learned at that center turbocharged my ability and taught me how to focus on things that are less interesting to me (which a lot of early college classes were).

My ability to focus has played a big part in the wins I’ve had in life. Learning techniques for focusing and practicing them took my natural abilities and habits to the next level. As I think about the one-minute attention statistic, I’m concerned about people’s diminishing ability to focus. If you’re aiming for outsize success, focus is something to consider learning about (just as you would any other critical topic) and practicing so you can develop or enhance your ability to focus. Being able to focus won’t guarantee you outsize success, but not being able to all but guarantees you won’t achieve success.

Friends and family joke that I have no shame about asking for what I want, especially when traveling and in other service-related situations. They’re right, and I own it.

I view knowing what you want and asking for it as a positive trait. So many people accept what’s offered to them in life. Life happens to them. They may want more, but they never take action to try to get more. I’m not wired like that. By taking the step of saying what I want and asking for it, I’m increasing the chances of getting the outcome I’m aiming for. I’m also making others aware of my goal or expectation.

I want to be clear that I’m not saying it’s okay to bully people into doing what you want or ask in a negative or nasty way. I don’t believe in that. I try to ask for what I want in a manner and tone that mirror how I would want someone to treat me.

I’ve explained to family and friend that I think about this in terms of risk and reward. In many of these situations, the upside dwarfs the downside. The upside is often a more enjoyable experience or a positive impact on you and those with you. The downside is just hearing no.

Family and friends still joke with me about this. When they do, I remind them of the famous Wayne Gretzky quote: “You miss 100% of the shots you don't take.”

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This is my two-hundredth weekly reflection. Here are my takeaways from this week:

• Learning – My learning survey started out as a silly exercise, but it’s turning into something resembling customer discovery. I’m surprised how interested people are when I ask about their learning habits.
• Focus – I paid close attention to how often people’s attention is pulled in multiple directions every day. The ability to focus appears to be becoming less common. Those who have it and use it will have a leg up on life.
• Trends – Jeff Bezos started Amazon after learning that the internet was growing at an insane annual rate. I’ve been thinking about new trends that are growing rapidly but aren’t well understood.

Week two hundred was another week of learning. Looking forward to next week!

My learning survey is ongoing and I’ve learned some interesting things. One of them I shared in a post a few days ago. Today I had a good chat with a VC investor. I’ve known him for a few years and think highly of him, so I was curious about his learning habits. The best investors and entrepreneurs are frequently trying to figure things out that others haven’t, so they tend to make learning a priority.

Our conversation was helpful, and he mentioned one big thing in several different ways: he wants to learn more but doesn’t feel like he has enough time.

I hadn’t thought about this, but it makes sense. Investors are busy people with jam-packed calendars. Squeezing in time to find material that contains the knowledge you want and then consuming it is difficult.

Now I’m wondering if feeling like time limits the ability to satisfy a desire to learn is common.

I recently caught up with a friend working at an investment firm. He’s been wondering when venture capital will escape its downturn. Many factors are contributing to the downturn. I shared two things I think need to happen: venture capitalists need to be able to sell companies to public market investors, and those companies need to be received well by public markets.

IPO activity and performance are important. Venture capital investors need (1) overall stock-market sentiment and direction to be positive (investors are in a buying mood) and (2) technology IPOs to perform well (not tank). If these two things happen, we’ll likely see more IPOs, and the venture capital industry could be on an upswing again.

As of the writing of this post, stock market sentiment is positive, and the direction of the market has been up (disclaimer: this could change at any moment). The NASDAQ Composite Index, as of today, is ~15,500. For context, the all-time closing high for this index was 16,057 on November 19, 2021. So we’re ~3.5% below the all-time high. This is encouraging, especially when you consider that the index was ~10,500 at the beginning of 2023.

The missing piece, though, is technology IPO performance. I followed the most recent high-profile technology IPOs, those of Klaviyo and Instacart (see here and here). Both companies went public in September 2023. Today I checked to see how they’re performing. Both are trading near the lowest levels at which they’ve traded as public companies and below where their IPOs were priced. Both companies priced at $30. As of this writing, Instacart is trading at $24.80, which is 17.3% below the IPO price. Klaviyo is trading at $24.74, or 17.5% below IPO price. During that same period, the NASDAQ went from ~13,500 to ~15,500, an increase of 14.8%. The performance of either company’s stock could change anytime, but as of today it hasn’t been great.

This is something I’ll keep an eye on. I suspect these and other factors will be key to venture capital’s downturn changing course.

I caught up with an entrepreneur friend this week. I’m doing my learning survey, so I asked him about his learning habits. That led to an interesting comment from him that stuck with me:

How I learned and how my kids will learn will be drastically different. I had to go to college to learn from people who possessed knowledge about jobs I wanted. My kids likely won’t need to go to college. The knowledge is more accessible now.

He went on to say this:

The jobs that my kids will have as young adults don’t even exist now. What people do for work will be so different from what prior generations did for work. How we learn and work is changing faster than people realize.

I’ve been thinking about this conversation because of my newfound curiosity about how people learn. The more I think about it, the more I believe my friend is right. If he is, then we’re likely to see disruption in education, which will create opportunity. These are early thoughts, and they’re subject to change. I want to think about this more and discuss it with other smart people.

Recently I listened to an interview in which the guest shared his favorite class in high school. It wasn’t a regular class; it was a work–study arrangement his senior year. He got to leave campus every day to work at a local business. He was paid for his time and received course credit. This work–study class was his favorite because he made money, which allowed him to buy and do things he enjoyed.

My favorite class in high school was woodshop. I loved it. I’d spent a summer working for a homebuilder and discovered I enjoyed woodworking. The teacher realized I knew what I was doing, so he gave me free rein. I could build whatever I wanted as long as I didn’t cause trouble or disrupt class (which the rest of the class did daily). It was the last class of the day, so he’d let me leave early when I was finished.

As part of my first “official” business, I sold speakers to friends and usually gave them a design for speaker boxes, too. They’d have to find someone to build the box for them, which wasn’t always easy. One day I realized I could use my time in woodshop class to build those boxes for my customers. I asked the teacher, and he thought it was a great idea. From then on, I was building and selling speaker boxes in woodshop class. It was a great hustle because I didn’t have to pay for materials, and I ended up showing a few classmates how to build their own speaker boxes.

Woodshop was my favorite class because it ended up being an entrepreneurial class. It allowed me to work on my business and make money, which made me feel financially independent from my parents. It also allowed me to share my knowledge about building speaker boxes with my classmates and do woodworking, which I find fun.