Early in my founder journey, I knew I had customers and that I could get more of them if I hustled. But for ages, I didn’t take time to figure out how big the market I was going after was. When I eventually did, I learned it was huge—over $30 billion. I also learned how competitive it was. Everyone wanted a piece of it. It was a cutthroat space. These insights forever changed how I thought about my business. I would have to fight tooth and nail to grow.

Today I spoke with a founder who’s solving a problem that he says inflicts 10% of the human population. A huge market. And a severely underserved one. People facing this problem want help but can’t find the solutions they need. This combination—huge market, little competition—is unlike what my company faced. If this founder can create a solution that solves this pain point effectively, the field is wide open. It’s a great high-growth opportunity if he can execute.

If you’re building a company, what’s the 30,000–foot view? How big is your market? How much competition is there? Knowing the answers to these questions is important. It may not change what you do, but it can have a big impact on how you do it and how fast you’re able to do it.

When I spoke recently with an investor in a medium-sized city in the Southeast, I asked him about his tech ecosystem. He thinks his city is moving in the right direction, but it keeps running into a couple of major barriers:

• Nontechnical founders – He comes across excellent founders regularly, but they can’t build a technical product. They struggle to find technical co-founders. If they don’t give up, they hire a development shop. His portfolio companies haven’t had great results with outside development shops, even when they have strong founders.
• Funding – The community has wealthy individuals and families. Their wealth derives from legacy industries that have historically been economic drivers in the city (not so much anymore). Founders struggle to raise funding because people who have the means to invest don’t understand tech start‑ups. It’s gotten better, but they’ve got a long way to go. They’re actively organizing a network of angel investors so people can educate one another.

I was happy to hear that this investor is working hard to help tech start-ups succeed in his city. Our conversation reinforced something I’ve thought for a long time. The South has talented founders, but to succeed they need support. Funding is a big piece. So is community to help them connect more easily and form well-rounded founding teams. I’m looking forward to working with this investor and others across the South to help founders reach their full potential!

Today Jeff Bezos announced that he will step down as CEO of Amazon later this year. Last week, I wrote about journeys cycling around. I couldn’t help but think about that post when I read the announcement. Jeff will still be involved with Amazon. He’ll be chairman of the board (to which the CEO reports).

Jeff pointed out that this transition will give him time and energy for other initiatives outside of Amazon, including the Washington Post, Blue Origin, and Bezos Day One Fund. It sounds like Jeff is working toward the “rebirth” I discussed in last week’s post.

Amazon is an amazing entrepreneurial story. The fact that Jeff led this company from the idea stage to over 1.3 million employees and a $1.7 trillion market capitalization (i.e. valuation) says a lot about him. He’s a legendary founder who I suspect will go on to do even more amazing things after Amazon.

I’ve recently chatted with a few entrepreneurs who have full-time jobs and are building companies on the side. It’s a familiar path. I did it myself. I was still in corporate America when I started my company. Only after it got traction did I decide to take the plunge. Whether to go full-time is a tough decision that I’m asked about often. Here are a few things I learned from my experience that I’ve recently shared with others:

• All in – At some point you have to go all in on your idea or it probably won’t reach its full potential. You can have success working it part-time—but not as much.
• Signaling – Going full-time sends a strong signal about your commitment to your idea. Investors, team members, co-founders . . . everyone will take you more seriously when you’re dedicated.
• Traction – It’s hard to make the same amount of traction working part-time as full-time. The week I went full-time my traction increased threefold (partly because I was doing all-nighters—which I don’t advise).
• Hidden gear – When people put it all on the line, they find a hidden gear. They reach down deep and find a way to make things work. They often surprise everyone, including themselves, with what they’re able to accomplish.
• Personal decision – Whether (along with when) to go full-time is a big decision that will affect all aspects of your life. There’s no hard-and-fast rule. It’s a personal decision —do what’s right for you and your situation.

If the stars align in your life and you’re able to jump in with both feet, you’re one of the lucky few (many people wish they were in your shoes). Make the most of the opportunity!

Yesterday I shared my thoughts on how a focus on culture is propelling Atlanta start-ups to success. Today, someone asked me how to build and reinforce a great culture. Here are a few things I’ve seen work:

• Ask for examples regularly – It’s one thing to know and be able to repeat your core values. It’s another thing to live them. During reviews (quarterly, monthly, etc.), ask team members for examples of how they’ve exemplified the company’s core values. Knowing this will be asked will prompt people to think about ways to live these values.
• Celebrate – When someone does something outstanding that aligns with your core values, recognize them and make sure the whole team hears about it.
• Publicize your values – Post them on the wall. Write them on employee key cards. Whatever it takes for people to see them regularly. It’s an effective reminder.
• Office Vibe – This is a great tool to gauge the health of your culture. You can send weekly pulse surveys to your team and receive anonymous feedback. And the team knows they have an outlet for communicating any concerns that could affect culture.
• Best places to work – Building a great culture takes time and energy. Once you’ve done it, publicize it. Many cities publish an annual list of best places to work. You have to enter to be considered, and they’ll rank you based on your team’s feedback. If you’re recognized as a top place to work, people will notice and want to come work for you.  

There are tons of other things you can do to create and maintain a great culture. This is just a quick list of things that can help.

Atlanta start-ups have been on a tear lately. Calendly raised $350 million at a $3 billion valuation, Rigor was acquired by Splunk, SalesLoft was valued at over $1 billion, and CallRail raised $56 million . . . all in the last few months. I spoke with a fellow investor about these wins. The founders’ styles and the companies’ circumstances are different, but we agreed there’s one thing they have in common that contributed heavily to their success: culture.

Each of these founders focused on culture early. They were intentional about the environment they wanted for their team. They took the time to think deeply about their core values, mission, etc. And they took it even further, making sure the decisions they made as they grew the company (including hiring) aligned with their values and mission. The results speak for themselves.

Some founders pay no attention to company culture. Big mistake. I’ve noticed two things that happen when they don’t:

• By any means necessary – Without clear values, sometimes people take the gray route in tough situations. Individual decisions may not be shady or bad, but over time they compound. People stray further and further from operating in an ethical way. One day you wake up and you have a company that achieves its goals by any means necessary. It’s Game of Thrones inside the company.
• Unmotivated team – Why you want to do something is usually clear to the founding team (or it should be). But as the team grows, everyone won’t understand the why if communicating it isn’t a priority. When people don’t understand why they’re doing something, they don’t work as hard. You can’t blame them. It makes sense. It’s hard to get someone to run through a wall if they don’t see any purpose or benefit to it. Next thing you know, you have an unmotivated team giving 50%.

Not making company culture a high priority produces lots of other perils. These are just two that I’m familiar with because of my own shortcomings as a founder. Take it from me, you don’t want to experience either of them. Once they set in, it’s hard to reverse them.

Congrats to Calendly, Rigor, Salesloft, and CallRail. They’re testaments to the idea that culture matters. Founders, take note: culture is a big part of success. Act like it.

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

• January – Today was the last business day of the month. January was an eventful month full of extremes. It felt like an extension of 2020 with a twist. I’m curious about whether we’ll continue to see extremes the rest of the year.
• Work from home – I worked exclusively from home this week. It wasn’t terrible—but it wasn’t great, either. A change of scene is important to me and I definitely notice when I don’t get it.  
• Wall Street & Main Street – Developments in the stock market this past week were astonishing. And I think the situation is far from over. In what direction will this saga go? What topics will it put at the forefront of popular culture? I hope it doesn’t lead to a repeat of 2008 and 2009.
• Ideas – Had some great conversations this week about some ideas I’m excited about. Looking forward to working with others to put some of them into action.

Week forty-four was pretty crazy—normal for me personally, but historic and extreme at a macro level.

Over the last few days, we’ve heard about the GameStop Reddit WallStreetBets saga playing out in the stock market. If you’re not familiar with it, you may want to read up on it. It will likely be remembered as a major historical event. The story centers around a Reddit community called WallStreetBets.

I’ve been a fan and user of digital communities since high school, and I’ve shared my thoughts about them in one of my daily posts. Some of these communities have helped me accelerate my learning and navigate unfamiliar situations, including my transition to corporate America and a new city.

What we’re witnessing is how powerful digital communities can be. Let me be clear: I’m not taking a position on current events. What I’m saying is that the fact that a group of ordinary people online can organize a call to action so big that it shakes Wall Street is a testament to the impact digital communities can (and will) have on our lives.

Love them or hate them, the people have spoken and digital communities are here to stay!

I had a great conversation with a good friend today. We talked about traits we’ve noticed in successful entrepreneurs. He shared some insights from his time in entertainment, while mine were from my time and relationships in tech. Interestingly, they overlapped.

• Learners – Successful people are learners. They’re aware of their gaps and actively seeking to fill them. Sometimes that involves taking on a role in someone else’s organization to set themselves up for future success . . . and perhaps more future success via their own vehicle. They set their ego aside to gain the knowledge they need for the future.
• Partnership – They recognize that they can’t do it alone and actively seek to partner with others who can help them succeed. Both bringing the right people inside their organization and partnering with the right outside people can work.
• Accountability – Successful people want to be held accountable and want their teams to be held accountable. They create cultures and put processes in place that reinforce this.

I always enjoy catching up with people in other industries and picking their brains. Today was no different. It reinforced that there are clear patterns and habits that contribute to success!

Today Calendly announced that it raised $350 million and is valued at over $3 billion. I’ve used Calendy since 2015 and am a huge fan. The team is talented and the product makes scheduling a meeting super easy. A few thoughts on this deal:

• Pandemic – The company already had an impressive growth rate, and it increased dramatically during the pandemic. They were well positioned for revenue redistribution.
• Revenue – They’re now at roughly $70 million in annual revenue. So, they’re eyeing $1 billion.
• Profitable – The company is growing rapidly and profitable—a dynamite combination.
• Hot market – The market is still hot. Investors are willing to pay higher valuation multiples for attractive growth opportunities.

Congrats to the Calendly team on a huge win! They’ve been building a great company and product for years. Can’t wait to see what happens next.