I met with a technical founder who spent seven years at a big tech company that’s a household name. I was surprised to learn that he spent a lot of his time rebuilding decade-old systems. The company worked on those systems only when it had to. On the outside, this company is cutting-edge, but internally, not so much . . . but the public would never know. The founder said the company didn’t grow to be worth hundreds of billions of dollars by fixing things that worked perfectly fine.

This reminded me of my time in corporate America. I learned then that some of the most well-known organizations have antiquated systems or processes. Not pretty, but things still worked, and that’s what mattered most. If it wasn’t broken, they weren’t in a rush to replace it.

Early founders should remember that good enough is all you need in the early days. Get something working and pushed out. You needn’t worry about using the latest and greatest technology or building something perfect, because those aren’t always the best use of resources. In many cases, done is better than perfect.

Today I listened to a founder pitch a solution to help small retailers sell more products to consumers. It facilitates taking an in-person interaction with a consumer online. The need for such a solution preexisted the pandemic, but the pandemic intensified it.

This pitch reminded me of the early days of my company. I bootstrapped it, so resources were limited. Because I couldn’t afford to hire a big team, I handled almost every aspect of the business. I was stretched thin. Whenever I found reasonably priced software that saved me time or money or enabled me to do something that I couldn’t do manually, I happily signed up. I recognized and was happy to pay for the value the software created for me and my business.

Change is flying at us. We’re facing more change in the next decade than we’ve ever seen. Small and medium-sized businesses (SMBs) won’t be able to keep pace on their own. They’ll need software to keep their businesses relevant as the world changes. I see a big opportunity to help SMBs of all kinds navigate the winds of rapid change.

During the Thanksgiving holiday, I caught up with friends who work in various industries and asked how 2021 has been for them. Their responses were consistent: it’s been busy for all of them. The companies they work for (or own) are growing, and some are having a hard time keeping up with all the growth.

Today I looked at the calendar and thought about the rest of the year. We have about three-and-a-half workweeks until Christmas. Once Christmas hits, it’s pencils down, as the year is essentially over for many (not all) industries.

I think December 2021 is going to be the last leg of a spectacular year. We’re not going to see a holiday-season slowdown: the next three-and-a-half weeks will be a mad dash for many people who want to close out the year strong. And I’m one of them—looking forward to it!

This past week was a much-needed holiday. After not celebrating Thanksgiving or Christmas in 2020, I’ve been looking forward to this holiday season. I went into Thanksgiving excited and also focused on being more intentional. I was looking forward to spending time with others, and I wanted that time to be high quality—I wanted to be present and engaged. I tend to not be as engaged if I’m in work mode, so I decided to not look at anything work related through Saturday. Overall, I think the mission was accomplished. I enjoyed the holidays, was able to unplug a bit, and was mentally as well as physically present with people I care about.

Today I started to prepare for the coming week and noticed I wasn’t being very productive. It was taking me longer to get things done and I wasn’t as focused as usual. I guess I was having a bit of an off day during my holiday. Today is Sunday, and my brain refuses to leave holiday mode even though I wanted to put it in work mode. Instead of fighting it, I recognized what was happening and leaned into it. It’s been two years since I had Thanksgiving, and it’s clearly something I’ve missed. I decided to put the work away and enjoy the last day of my Thanksgiving holiday!

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 enjoy the Thanksgiving holiday. It’s a nice time when most people are focused on family, friends, and fellowship. The past eighteen months have been unprecedented in several ways. One example of that, on a personal level, is that last year was the first time I didn’t celebrate Thanksgiving as I always had. That had a big impact on me—it was a stark reminder of how fortunate I’d been in all the years before.

Yesterday felt like a normal Thanksgiving, and I really enjoyed it. After the day was over, I reflected on how fortunate I am and all the things I’m thankful for. Everything isn’t exactly how I want it, but life is good and I’m appreciative of that.

What are you thankful for?

Happy Thanksgiving!

I hope everyone had a safe and healthy holiday!

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.

I read a quote today about decision-making that I love:

Call it like an umpire: you’re either out or you’re safe.

As a founder, you have to make quick decisions, often using intuition. A quick decision, even if it’s wrong, is better than stopping the game.

I didn’t know that in my early days as a founder. As I gained more experience and confidence, though, the speed of my decision-making improved. As my decision-making sped up, the company’s growth did too. I learned to not worry about being right or wrong. Instead, I made a decision and focused on learning. Right or wrong, there was always something I could learn and apply to make better decisions in the future.

I still try to make decisions quickly and learn from them. Sometimes I’m right and sometimes I’m wrong, but I’m always learning!

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A founder I know had a great vision for his company. He worked for years to get customers and had success, but not the hockey-stick growth he expected. Then the pandemic hit, and customers flooded in.

I caught up with him and asked him about his journey. His most important observation was this:

I knew I was right. I just didn’t know when I’d be proven right. Giving myself enough runway was the difference maker.

Timing is a huge factor in the entrepreneurial journey. Often, founders can’t control it. When things don’t go according to their planned timeline, they have a choice to make: keep building and wait for the time to be right, move on to something else, or choose some hybrid of the two. There’s no right or wrong answer. Each founder must make the decision that’s right for them and their team.

This founder chose to keep going, and it worked out for him in a big way.

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