Entrepreneurs are often considered creative people because they think of solutions others haven’t. I recently listened to someone share an interesting perspective on creative people. He thinks of creativity as the ability to connect dots. He doesn’t believe creative people are creating ideas out of thin air. They’ve had more life experiences, talked to more people, consumed more knowledge. They have more nodes that can be connected. They’re able to come up with things people with fewer nodes can’t.

I’ve been thinking about this today, and I’m undecided about whether I agree. It’s an interesting way to think about creativity. If it’s accurate, it implies that creativity isn’t something people are born with. People can enhance their creativity by intentionally amassing more nodes. Understanding this could be enough to inspire people to believe in themselves and put in the work to become creative people. That change in mindset could be powerful and lead to significant change.

I’ll think about it more and get others’ perspectives.

Yesterday I shared my ideas on how diversity of thought can help smaller communities. A buddy responded with a few of his:

• Insular – He used this word instead of “smaller,” and it got me thinking. The size of the community likely isn’t the right way to describe what I’m referring to. Lots of progressive, innovative communities aren’t huge. Though small, they’re generally receptive to new ideas, even from outsiders. “Insular” is a better adjective.
• Conduit – He’s noticed that he has a different network than most in his hometown, an insular community. He’s credible in both communities and can lend credibility to both sides. Start-ups and people from the insular community that he introduces to his network are embraced with open arms and may even get opportunities they otherwise wouldn’t. And he’s able to convince people from his network to visit his hometown. When they do, they’re embraced with open arms by locals because of their connection with my buddy. If he didn’t act as a conduit, the two communities would tend to distrust one another. When he does, though, the people in both have open minds and generally have a great experience and positive impression of each other when all is said and done.

I’m glad my buddy shared his thoughts with me. I think he made some great points. The conduit role he described is a great third way to foster diversity of thought and help insular communities thrive. I’m looking forward to my thoughts evolving more around this topic.

Years ago, a buddy told me that one of the problems with second- and third-tier cities was that people left after graduation for better opportunities in bigger cities. I think he called it a brain drain. He believed the solution was to convince graduates to never leave. As someone who left Louisiana for Atlanta, I did the exact opposite of what he was advocating for. I agreed that a solution is needed to help less-progressive communities keep up with the pace of change and stay economically competitive—but not his solution.

Exposure to new ways of thinking and doing is an important part of helping these communities evolve. Instead of convincing graduates to never leave, let’s encourage them to go to larger markets to gain exposure with the goal of returning home. To bring back those new approaches and ways of thinking. And to combine them with their understanding of the cultural norms in their home community to help create bespoke solutions that their community can rally behind.

All graduates who transition to larger markets won’t move back home, and that’s OK. They can still play an important role. Because they understand two different communities, they have a unique perspective that qualifies them to be a bridge between them. They can help make others aware of opportunities in larger markets and ease the transition for those who aspire to move.

Exposure can lead to diversity of thought, a powerful change agent for a smaller community. It seems to me that making diversity of thought more accessible is a better path than limiting it. These are just two rough ideas about how to encourage diversity of thought, make it more accessible, and hopefully empower people to change the communities they care about.

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

• New Orleans Entrepreneur Week – I spent part of the week at this event. It exceeded my expectations. I had no idea the city had $2 billion in exits last year. Those exits, along with other traction, have created massive momentum that will lead to great things.
• Common threads – This week reinforced how commonalities help us forge deeper connections with people. They’re powerful as we build relationships and work to understand who people really are (as opposed to how they want to be perceived).
• Proximity to success – Being around other people who are doing great things can have a powerful impact. You may become aware of a path you didn’t know about. Your beliefs about what’s possible expand. When you see that one person has done something, you will begin to believe it can be done, and that you can do it.

Week one hundred four was full of activity. I learned a lot and connected with many great people.

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A founder shared his fund-raising journey with me today. In the last two weeks, he’s gone from zero traction to conversations with multiple firms and a likely path to getting his round closed. Anything could happen between now and funds being wired, but I was curious about what changed in the last two weeks, so I asked. The founder said he’s been more intentional about expanding his network. He volunteered to speak at NOEW because he knew lots of investors would attend. He met with folks leading up to the event and during it. As his network expanded, the possible paths to getting his round done proliferated.

Networks and relationships can have a big impact on the trajectory of a company (not just on fund-raising). Knowing the right person, or the right person knowing that you exist, can lead to doors being opened that were previously closed and to amazing opportunities. Building external relationships isn’t the focus of a CEO, but it’s something they should be mindful of and intentional about. Especially if they’re fund-raising.

If you’re a founder looking to build something great, try to build a network before you need it—or build strong bonds with a few key people who have large networks. As your network expands, your company’s possible paths to success will multiply.

Today I had the pleasure of attending a NOEW session where Evan Spiegel and Michael Lynton participated in a panel discussion. Evan is the cofounder and CEO of the parent company of Snapchat, and Michael is chairman of the board of directors. Evan has taken Snapchat from an idea during his product design class in college to a publicly traded company with a market capitalization of around $58 billion. A few big takeaways from his chat:

• Mentorship – Mentors are enablers of founders’ visions. Be clear on where you want to be, and mentorship will help you figure out how to get there.
• Indecision – Not deciding can be worse than making the wrong decision. Snapchat went back and forth on relocating from Los Angeles to San Francisco. The indecision kept everyone in limbo and made things like recruiting difficult because people couldn’t plan. Once the decision was made to stay put, everyone could plan and execute around it (even if they didn’t like it).
• Visual communication – Evan saw the potential of visual communication as a richer and more expressive form of communication in 2011.
• Rejecting takeover – Evan was approached by Meta (parent company of Facebook) to acquire Snapchat. He didn’t want to sell because he was confident that more value could be created by executing his plan. But he had to convince the board, which wasn’t an easy task. The company was very young, and a multibillion-dollar exit would have been a massive return for the venture capital firms that backed it (and had a board seat). He ultimately convinced the board to reject the offer, and the rest is history.
• Quick to fire – Snapchat experienced a period of turnover at the leadership level before it found the right people. Michael praised Evan’s ability to quickly pull the plug when someone wasn’t working out. It was painful and the optics weren’t good, but it allowed them to find the right people sooner.

Evan is an impressive and visionary founder. I enjoyed listening to him share his wisdom and look forward to following his entrepreneurial journey.

Today I spent time listening to a local angel group host a panel discussion. The purpose of the discussion was to demystify the process of getting investment from the group. The audience was primarily early founders.

This angel group’s members are mostly current and former entrepreneurs, so they have a wealth of start-up knowledge. They’re also civic-minded. They want to see their community prosper and believe entrepreneurship can have a material impact. The group evaluates deals across the country but emphasized that local entrepreneurs who meet their criteria get preference. And they made the point that they’re not a charity—they seek to get a return on the capital they invest.

This angel group (like many others) has a profile that makes them vital to the local entrepreneurial ecosystem. They seek to do good (help founders) while doing well (making money). Given their backgrounds, they’re uncommonly qualified to help with something most people have never attempted and can share invaluable experiences. You may get one or two of these qualities in the profile of another sort of investor, but probably not all three.

Today reinforced my belief that operators turned angel investors are essential ingredients in a successful start-up ecosystem.

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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