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

• Connecting the dots – I spent a few weeks thinking about a problem and collecting insights from others. This week, I was able to connect some dots. I still have lots to figure out, but it felt good to make some progress. Not sure where this will go exactly, but I feel good about the direction.  
• New project – I hit an unexpected snag. I’m frustrated, but I’m reminding myself that part of the reason I’m doing this is to learn. I still want to get this wrapped up before Christmas, so I’ll keep pushing next week.  

Week eighty-nine was busy. Still have lots to get done before December 25.

An entrepreneur buddy recently was a guest on a podcast, and he shared the recording with me. He told the host about his journey and his learnings to date as an entrepreneur. One of the things he mentioned was that he’d had tunnel vision early on, which was a mistake. He kept his head down and executed as best he could. He didn’t grow up in an entrepreneurial family and didn’t know many entrepreneurs. He used his street smarts and hustle to figure it out . . . the hard way.

Looking back, he now realizes that his journey was more difficult than it needed to be because people who came before him did the exact same thing: built their businesses, heads down. They weren’t sharing what they were learning as they went along. My friend wants to change this approach, which perpetuates a cycle of people making the same mistakes and learning the hard way.

His journey as an entrepreneur is far from over, but he now makes a point of publicly sharing it and what he’s learned. He doesn’t have it all figured out, and he says so. But his hope is that someone listening will avoid some pitfalls and execute faster than he was able to. Or someone on the fence about entrepreneurship will be motivated to give it a try.

Kudos to him for being intentional about sharing his learnings in real time. All too often, successful founders wait until the end of their career to share their knowledge. It’s great that they do that, of course, but I think that doing it along the way gives the people who hear them information that’s more current and therefore more relevant—so it’s more helpful.

I hope more founders start sharing what they learn as they go!

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

• Christmas push – This week kicked off the push to Christmas. Lots to get done before then! The next few weeks will be busy.    
• Prioritization – I spent time thinking about my 2022 priorities. So far, they’re the same as in previous years, but they’re in a different order. I’ll spend more time thinking about this.
• New project – I started working on a new project. I’ve never done this before, and it’s been an interesting learning experience so far. I anticipate more bumpy learning but am hoping I can wrap it up before Christmas.  

Week eighty-eight was steady. Looking forward to getting a lot done before December 25.

I enjoy spending free time learning about new things online. When I find something I want to learn more about, I seek out credible people who’ve created useful content on the topic. I’ve been amazed by some of the videos I’ve found since the pandemic began. The content and production quality are impressive. The creators take what they’re doing seriously, which has resulted in large, faithful audiences. A few have been producing videos for less than a year, but you’d never know that from the quality and frequency of their content.

The trend of individuals monetizing content is likely to continue for the foreseeable future. More subject matter experts will monetize their knowledge and create followings. This got me thinking about picks-and-shovels opportunities. Much of this content is created by a single person or very small team. I suspect many are limited in their abilities and would welcome opportunities to do more with less or the same thing in less time. And I suspect the market for tools to support these creators is small but growing quickly.

I believe an opportunity exists for entrepreneurs to build a big business helping creators via software. These creators are small businesses or sole proprietorships, so there’s an opportunity to build a large and sticky customer base. They probably aren’t using any software now, so they don’t expect a perfect product. The market is small, so I doubt it’s on the radar screen of large software companies because it won’t move the needle on their sales now.

As I continue learning online, I’ll be paying close attention to what tools these creators adopt. I think that someone who deeply understands their pain points will strike entrepreneurial gold by solving their problems.

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!