I’ve been thinking about identity and habits lately. I’ve come at identity from two angles: Who do I want to be? Who am I? To answer the latter, I looked at the habits I’ve had for a long time. I suspected that I believe some things about myself that I haven’t consciously acknowledged. It’s been an interesting process that’s made me more self-aware. And it’s shed light on a few things, including my investing habits.

I’ve been into finance and investing since high school. I didn’t come from a wealthy family and didn’t have money to invest, but I sought out books and online resources to learn. In college, finance was the only major I seriously considered even though I didn’t know anyone who worked in the field. As an adult, I spent free time (founding a company didn’t leave much of it) keeping up with public market investing. Now I spend my days investing in early-stage private companies at Outlander VC and still do personal investing in my free time.

Next, I asked myself why: Why have I established these habits? What is it about investing?

I took it a level deeper and reflected on what I’ve enjoyed about investing all these years to answer these questions:

• Not the smartest person in the room – Investing attracts some of the smartest people. I love learning from bright people and having a constant feeling of not being the smartest person in the room.
• Perpetual change – Investing is always changing. I’ve never reached a state of comfort and likely never will. This is exciting. It keeps me on my toes.
• Complexity – Investing has a lot of moving parts. I enjoy trying to parse the complexity so I can achieve a desired outcome.
• New problems – I love learning about problems and how companies are creating value by solving them.
• Endless – No matter how much time I spend learning about investing, I only scratch the surface. It’s a vast industry with an endless learning curve.
• Intellectually challenging – For the all the reasons listed above and many more, I find investing a stimulating challenge.

I’ve had an investing habit for many years. With that kind of consistency, I guess I have a core belief that I’m an investor (I don’t claim to be a good one). It feels very weird to say this publicly, and I’m not comfortable with it, but it’s hard to argue with my habits over the years, and I can’t deny that I enjoy it.

As an early founder, I had huge knowledge gaps. I didn’t know a lot about start-ups, and that resulted in slow execution and decision-making. Filling those gaps helped accelerate my execution and thus the success of my company.

Since then, I’ve been passionate about continual learning. I’ve developed my own system, but I recently started researching how others approach it. I came across this quote from Warren Buffett:

Read 500 pages every day. That's how knowledge works. It builds up, like compound interest. All of you can do it, but I guarantee not many of you will do it.

This really stuck with me. I agree that knowledge is like compound interest. It builds upon itself. New knowledge isn’t acquired in isolation. It combines with what you’ve already learned to improve your understanding and decision-making. When you look back to a long time ago, you realize that your understanding and decision-making are light years ahead of where you were then because of the compounding effect.

Warren’s 500 pages every day isn’t doable by most people, but frequency is more important than quantity. Reading daily essentially increases the compounding rate of your learning. The more often you add to your knowledge, the better your understanding and decisions become. If you read every day, that’s 365 chances to compound your learning.

The last part of the quote explains what separates the good from great. Most people could take advantage of this life hack—but won’t. So, if you commit to this one habit, you’ll set yourself apart from almost everyone over time.

I don’t think it’s a coincidence that Warren Buffett and other successful people read daily. They recognize it’s something they have total control over that has an outsize impact on their chances of being successful.

Today marks the end of my eighty-sixth week of working from home (mostly). Here are my takeaways from week eighty-six:

• Holiday push – The week before a major holiday is always busy for me. Everyone is trying to push things over the finish line before the holiday. This week was no exception. I tried to plan my schedule accordingly, but I could have done some things better. I’ll manage my calendar better the week before Christmas.    
• His way – I met with an investor this week who’s a hustler and has done things his way. He refuses to bend on his beliefs. It’s paying off for him; he’s proving everyone else wrong. Talking to him reinforced to me that there’s something to be said for standing by your beliefs, even when others question them.
• Opportunity – I’ve been thinking about how others gave me opportunities in college and early in my career that changed my trajectory. I’m thinking about how lucky I’ve been and how to provide opportunity to others.

Week eighty-six was hectic. I’m tired and glad it’s over. Looking forward to the holiday next week and some time with friends and family.

Today marks the end of my eighty-fifth week of working from home (mostly). Here are my takeaways from week eighty-five:

• Partnership mindset – I’m a big believer in the saying that there are no perfect people, only perfect teams. This week reminded me that partnership is important to doing something great. The partnership journey isn’t always easy, so alignment early on is important. You might disagree on how to get there, but you can compromise because you know you’re both trying to get to the same place.  
• Hustle – I meet with founders and investors every week. The ones who are hustlers consistently stand out. Hustle is a big part of their success. I noticed this again this week.    
• Common threads – Wrote about this a bit this week. Finding ways to relate to people has been helpful in getting to know them. I do this naturally, but I want to be more intentional about it.
• Giving back – I was able to give back and help somebody out this week, and it felt good. I’m rooting for him and expecting him to do amazing things in life and business.

Week eighty-five was a good one. I was in a groove and made progress on important things. I hope to repeat that next week.

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Today marks the end of my eighty-fourth week of working from home (mostly). Here are my takeaways from week eighty-four:

• Impact – I’m still thinking about this a lot (and having great conversations about it). I have some ideas for having an impact on founders and may start to test one pretty soon. Looking forward to learning.
• Directionally accurate – I’m naturally wired to have a destination in mind that I’m aiming for. Over time, I’ve learned that I can take action without a clear destination—I just need to lift my head periodically to confirm I’m still headed in the right direction. This week reinforced this.  
• World Series win – The Atlanta Braves won the World Series for the first time in over twenty years. This is a big win for the city and puts it on outsiders’ radar screens. Sports have a way of uniting people, and I’m excited to see how this win will affect Atlanta.  

Week eighty-four was positive. I was productive and reenergized. Looking forward to repeating this next week.

Today I toured a real estate project a buddy just completed. He’s easing his way into entrepreneurship and the industry. This project was the largest (and most complicated) he’s taken on to date. As usual with construction, it didn’t go as planned, but it’s a financial success. Not as much profit as he’d initially hoped, but a success nonetheless. As we chatted, he kept mentioning how he should have spent less but didn’t know any better when decisions were being made. I realized that his perspective was preventing him from realizing how this project was a win in other ways, too.

The project wasn’t easy. The price of lumbar surged in the middle of it. Labor rates increased, while the reliability of crews decreased. These and other factors led to higher costs and a longer timeline. As each obstacle presented itself, my buddy figured out how to overcome it. It was stressful, but he found a way to get it all done. Tough circumstances, I thought, but awesome learning experience.

We talked about his future projects and what he plans to do differently. I pointed out how much he’d learned and how valuable that knowledge will be. Lots of people pay tuition to go to school to learn what he got paid to learn. In the end, he reflected on where he was before and after this project and agreed. It was a huge success and is likely to be the turning point in his real estate career.

Knowledge acquired through experience (yours or others’) can be a big factor in entrepreneurial success. If a situation doesn’t end quite how you’d hoped, reflect on what you’ve learned from it. The knowledge you’ve gained will be invaluable next time and every time—it’s the gift that keeps on giving!

Today marks the end of my eighty-third week of working from home (mostly). Here are my takeaways from week eighty-three:

• Impact – I had a conversation with a founder turned early-stage investor about impact. I’ve been thinking about it for over a year, but this conversation got me thinking about ways to maximize my impact.  
• Working on me – I spent time this week working on myself. It was good to take a step back from working on stuff for others. I learned a lot of great things and can’t wait to implement them. I need to get back to doing this regularly.
• One year – Had an enjoyable chat with a good friend this week. We discussed my theses today versus one year ago. He thinks I articulate my thoughts more clearly. I’ve also gotten more comfortable thinking through what the future will look like and why. It was nice to hear his feedback, and it forced me to think about how my thinking has evolved. What a difference a year makes.

Week eighty-three was great. I’ve gained a lot of clarity and learned some interesting new things. I’m reenergized and looking forward to next week.

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I listened to a friend’s seven-year-old share his views on a prominent technology company and its founder. I was shocked by how much he knew. I asked his father if he had discussed this company or the founder with his son. No, he said, and he wondered where he’d learned about them. Our assumption is, the internet. We think he heard about the company, liked it, and did some research to learn more.

The internet didn’t exist when I was his age, but I vividly remember finally getting online access at my parents’ home. I spent hours digging into subjects I was interested in and reading everything about them I could find. It was a game changer. Forums and chat rooms exposed me to new things—to a world I didn’t know existed. I ended up using some of this knowledge to start a company in high school. I’d say the internet was a big reason I became an entrepreneur.

Today I still spend lots of time online learning about things that interest me. I try to find a credible person (on Twitter, Medium, or Substack) and read about what they know or think about a topic or watch YouTube videos of them sharing their thoughts. I’ve gained a lot of extremely valuable knowledge this way.

Information is power. I love how the internet has made information more available to the masses. It’s empowered people to share their expertise and given others a way to consume it. With decentralization and other trends gaining momentum, I suspect my friend’s son and his generation will experience a completely new way of learning. They will be more knowledgeable than previous generations, and how they learn will likely be radically different.

Today marks the end of my eighty-second week of working from home (mostly). Here are my takeaways from week eighty-two:

• Schedule – I’ve been doing a better job of managing my schedule a few weeks out. It’s more of a mix, now, of time open to others and protected time. This week and last, that helped me be more efficient and get things done.  
• Future thinking – I shared my thoughts on future thinking in a post this week. It’s especially important when you’re looking at a window of opportunity that’s about to close. I’ve been reflecting on this more. The people I’ve seen build amazing companies and have outsize successes (personally and professionally) are future thinkers. They see the world through a lens of what’s possible, not what is.
• Pace – Just like last week, this week was busy. Next week will be too. Lots to do before the holidays.  

Week eighty-two was another busy week. More of the same is coming for the rest of this month.

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I had a spirited chat with a friend this week about a house in Atlanta that just hit the market. We debated how long it will take to sell. I think it will sell within a week, and my friend thinks it will take a few months. Surprised, I dug into his why. He things it’s overpriced and that a price reduction will be needed to move it after it sits unsold for a few weeks. I think the price is fair. The true disconnect is what we think the house is worth.

After more back and forth, I got to the root of our disagreement. I’m bullish on Atlanta. I think the city offers qualities other major metros can’t that make it a place people see themselves settling down in and calling home for the long term. And pandemic dynamics contribute to it being a desirable destination. Home prices reflect this and are likely to continue increasing for the foreseeable future. I believe that prices are fair relative to where they’ll be in the future.

My friend has lived in Atlanta for a long time. He remembers a glut of houses on the market after the financial crisis and some now-trendy neighborhoods being seedy. He believes Atlanta is in a real estate bubble and prices will drop at some point. In other words, he believes current prices are inflated relative to historical prices.

As I reflected on our conversation, I realized that we had different perspectives: I was focused on the future, and he was focused on the past.

Looking at an opportunity, I’m a fan of future thinking. I wasn’t always like this. Flipping this mental switch transformed how I analyze opportunities. I’m able to see opportunity and capitalize on it because I can still see it as “cheap.” If things go as I predict, the asset will increase in value, and I will have gotten a deal at its current price. It’s irrelevant that I didn’t buy at the cheapest historical price, a consideration that I view as a mental trap.