As an early founder, I had huge gaps in my start-up knowledge. I didn’t know how to build something from zero to one. Luckily, I was able to connect with other founders who shared their experiences with me. With my gaps filled, I was able to scale my company.

Today I caught up with a founder friend who took a different path to fill her knowledge gaps. She was forced into entrepreneurship when she lost her job during the financial crisis. Her industry was decimated, so she couldn’t find another job. She became an entrepreneur to survive. It was very early in her career, and she knew nothing about being a founder. The company lasted for five years before she threw in the towel. She then took two jobs in her space with experienced founders for a number of years.

Today she told me that she went full-time as a founder again last year and things are going better than she could have imagined. I asked what’s different this time around, and she said it’s experience. The things she learned from her failed company and working with other founders helped her understand what she’s aiming for. With that mental blueprint, she’s now executing and making decisions completely differently.

I filled my gaps by learning from the experience of others, while this founder filled hers by first failing and then working closely with other founders.

If you’re a founder, figure out whether you have knowledge gaps. If you do, work to try to fill them. It can be done in a variety of ways. Just find one that works for you.

I caught up with a founder today who told me about his new start-up. He’s had two successful ventures already, so I was curious about his motivation for this third one. He shared that his perspective has evolved with each company:

• Not have to work for anyone – His first company was meant to replace his job. He wanted to own all the equity and cash flow to fund his family’s lifestyle.
• Financial independence – With his second company, he was focused on achieving financial independence. His goal was to create a scalable solution that had equity value for his investors and him. Even though he raised investor capital, he mitigated for the downside and made decisions that could be interpreted as conservative.  
• Swing for the fences – Now, he wants to create a massive third company and is willing to take the risks necessary to make that happen. He’s got cash flow coming in from his first company that covers his family’s needs. He has a material nest egg from the sale of his second company that secures his family’s future. He’s now completely focused on the upside of this new venture, and he’s raising a significant amount of venture capital to execute his plan.

As we chatted, I shared my thoughts on psychology that I talked about in yesterday’s post. He agreed and said he was playing to not lose with his first two companies, but he’s playing to win with his latest one. As he’s gained more entrepreneurial experience and created a safety net for his family, his psychology has evolved. What terrified him in his first two ventures now excites him in his third one.

Today was a reminder that founder psychology isn’t static—it can change over time.

I had a great chat with a founder friend recently. We connected years ago when I was an early founder. He’s super successful and has built a bootstrap company that does tens of millions of dollars in revenue annually. Our early chats helped me think bigger about my own start-up.

We talked about psychology and the outsize impact it can have on outcomes. How a person thinks about what they’re doing has a much bigger impact than most people realize.

A big takeaway from our chat is the difference in approaches people have when they’re building something and how each person’s way of doing things is heavily dependent on their psychology. Some people limit themselves by focusing on the downside. Failure is terrifying to them, and they want to avoid it. Their focus on not failing affects their decisions and actions. They try to mitigate every downside, which leads to more conservative and protectionist decisions. Said differently, they play to not lose.

Some people believe there are no limits to what they can achieve. They see things differently than most. Their focus is sharply on the upside: on winning, being the best, building something big, or however they define success. They see a big opportunity and make every effort to capitalize on it. They usually make swing-for-the-fences decisions—bold ones, with lots of risk but also the potential for huge upsides. The risk associated with the decisions they make would terrify most people. Said differently, they play to win.

Entrepreneurs are generally considered to be risk takers, yet both psychologies can be found among successful entrepreneurs. There isn’t a right or wrong psychology, because you can be successful with either. The big difference is the magnitude of your success. Entrepreneurs who have had outsize success tend to have a play-to-win mindset.

What are you doing, psychologically speaking? Playing to win, or to not lose?

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

• Two years of posting daily – I’ve been writing daily posts for two consecutive years. That’s almost 750 consecutive posts. I’ve grown a ton from this habit. I’m looking forward to another year plus of it.   
• Mentality – I spent this week thinking about and discussing the importance of mentality —that is one’s outlook.How you think about things manifests in your actions and ultimately your outcomes.
• Inbox zero – I’ve been working toward every-day inbox zero for all my inboxes. Achieving it is hard but maintaining it is even harder. This daily exercise has a huge impact on my productivity and focus. I’ve gotten to the point where I’m consistently at inbox zero with one inbox. NowI’ll focus on achieving it for my other inboxes too.  

Week one hundred three was long and busy. I got a lot of things done, so the effort paid off. I’m looking forward to repeating this next week.

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I had an interesting conversation with a founder. I always love to understand what drove someone to pursue entrepreneurship—it’s a risky path, a big decision. Understanding why they chose it can tell you a lot about them. This founder had a great, high-paying job at one of the most-recognized companies in the world. I really wanted to understand why he gave it up.

His answer wasn’t what I expected. He said he changed his perspective. He began looking at the world in terms of time, not money. He thought about how much time he had left to live and the closing window of opportunity to start something that he was passionate about. By the time he could amass FU money from his job, he might not be able to start the company he’s passionate about. His realized that his time is more valuable than the additional money (he’d already amassed a nest egg) he’d be chasing.

Time is the great equalizer. You can’t buy it, sell it, or trade it. Once it’s gone, it’s gone. Everyone gets the same amount of it. How you use it is a big factor in your trajectory. This founder is choosing to spend his time building something he’s passionate about and enjoying his family. How are you spending your time?

I’ve been using a certain software platform for years. It’s complex and took a long time to learn. Over the years, though, I’ve gotten familiar with it and learned how to meet my needs using it. Recently, a friend told me about a competing platform he’s using. He described features he uses regularly that my platform doesn’t have—some of which could be valuable.

I decided to give the competing platform a try. I signed up and was shocked at how unintuitive it is. I tried to use its training materials, but they were of minimal help. I called the helpdesk with questions about specific features. After being transferred around a few times, I began to suspect that no one on the help team knows how to use those features. I asked to schedule an onboarding session and was told that’s not an option.

The platform I’ve been using had a great onboarding process and has a great customer success team. It was easy to begin to learn how to use it. The competing platform may be better, but I’ll probably never know since the onboarding process has been so awful.

My takeaway from this experience is that it takes more than a great product to build a great company—you also need a process that makes it easy for customers to try your product. It’s hard to scale a great product with awful onboarding.

I spent time today wrapping up a project I’ve been working on. It involved lots of moving pieces and nuances. The process to understand it all was much slower than I’d planned for, which prevented me from completing it on time. After I finished, I realized that everything I’d just done was a complex and painful workflow. If I’d used software to help me with it, it would’ve taken significantly less time and energy.

This project reminded me how much value can be created by helping others easily navigate complex workflows. Going forward, I’ll happily pay for software that helps me complete projects like this with less time and effort and fewer errors.

Solutions for complex workflows aren’t sexy at all, but they create massive amounts of value for customers and can be sticky (i.e., customers aren’t likely to leave). If you understand how to navigate complexity in a repeatable manner, there could be a massive entrepreneurial opportunity waiting for you. Lots of people like me would happily pay for help running the gauntlet.

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I was chatting with a founder recently about how he plans to grow his company. He’s realizing he can’t do everything himself, so he’s trying to hire people in roles that are taking up too much of his time. He’s moving from executing the work to managing people who do it. He isn’t looking to hire anyone who can think strategically or own functional areas of the business. Instead, he’s building a company where all decisions run through him.

As I asked more questions about why he’s taking this approach, I realized that he doesn’t see how big an opportunity is in front of him. He’s trying to build his company to handle today’s customers, not tomorrow’s.

This founder can build a great business. But he won’t do it this way. His growth will be limited because his team will be built to execute, not problem solve and think independently. As they encounter new situations, they’ll have to come to him for answers. The likely result? He will become the bottleneck that slows his company down.

If you’re a founder looking to grow your team, take a moment to ask yourself if you’re building a team to scale—or not. Nothing wrong with either; just make sure your approach aligns with your goal.

This past week marked two consecutive years of sharing my thoughts publicly. On March 9, 2020, I began posting because of a friend’s challenge. That sixty-day challenge has continued for over 730 days. Today I spent some time reflecting on what I’ve learned from doing this every day for two years. Here are some of my thoughts:

• Compounding knowledge – Posting daily forces me to stop and reflect daily. Reflecting and taking in new information daily has a compounding effect and has accelerated the rate at which I’m learning. More thoughts on this here and here.
• Unexpected benefit – When I started, the goal was to share what I’d learned as an entrepreneur with other entrepreneurs. It was a way to give back. I didn’t expect to get much from it personally, but I have.
• Difficulty – It was hard to establish the habit at first. It’s in place now, but there are still days when it’s harder than normal to create a post.
• Frequency – Posting daily is the right rhythm for me. If I’d started off doing it weekly or monthly, it wouldn’t have lasted past the initial sixty days. The habit is second nature now.
• Topics – I’ve likely shared most of the lessons I learned as a founder. This year I want to focus more of my posts on where I’m headed and new things I’m working on.
• Reach – Over the past two years, I’ve been consistently surprised by my posts’ reach and audience. Whenever someone tells me a post was helpful, it’s usually when I least expect it and from someone I’m not expecting it from.
• Mental exercise – The brain is an organ that needs to be exercised just like any other. Doing this daily makes me feel like I’m giving my brain the exercise it needs.
• Quality – With a daily frequency, every post isn’t going to be a Pulitzer piece. That’s OK. The process of reflecting daily is what I get value from. Some days are less eventful than others.
• Public diary – I’m excited to have a diary of thoughts that I—and others—can go back and review.

I wasn’t sure how I would feel about doing something like this for such a long time. It’s been challenging and fulfilling at the same time. As with anything else, there are pros and cons, but after two years I can see that the positive far outweighs the negative. I’m looking forward to continuing the habit. Year three here we come!

Over the last year, I’ve chatted with a few founders who are relocating to Atlanta. I’m bullish on the city and believe the best is yet to come, so I’m glad others are recognizing its value and moving here. I sat down with one of these founders, who just solidified his move date. I wanted to better understand his decision.

This founder shared a lot of things, and one of them especially resonated with me: he’s too comfortable. He doesn’t feel challenged and isn’t growing. He isn’t around people who are pushing the envelope, so he hasn’t been pushing as hard as he could, either. He’s hungry and knows he can go further as an entrepreneur but isn’t in the right environment.

During his visits to Atlanta, he found the community welcoming, and entrepreneurs were willing to share their experiences and relationships. The variety in the types of industries entrepreneurs operated in was refreshing.

Atlanta isn’t the only place founders are migrating to. Miami, Austin, and other cities are also attracting great founders. I do believe that Atlanta is unique, though, in that many founders who relocate see themselves putting down roots and calling Atlanta home for the long term. I’m excited about this movement and can’t wait to see what’s in store for Atlanta. I hope it will be known as—among other things—the place entrepreneurs call home.