A few days ago, I posted about bad days. They’re inevitable—part of the founder journey (and life in general). After revisiting that post with someone, I realized I didn’t say anything about how to cope with bad days.

I’ve found that talking through bad days can be a tremendous help. Peers (early-stage founders) who can relate or people who’ve taken your journey are most helpful. They understand exactly what you’re going through and have valuable perspectives. When I tried to have these kinds of conversations with others in my circle, it just fell flat. They wanted to help but couldn’t understand what I was going through.

If you’re having a bad day, consider talking it out with a peer or someone credible. And if you know someone who’s having a bad day, can you lend an ear? Your roles might flip tomorrow.

I previously shared my thoughts on how more people are taking control of educating themselves and how future generations’ education will be radically different. Information is more readily available and distributed than ever before. Credible people can now talk directly to the people who want to consume their teachings. While democratization of information is positive, it does present a new challenge: how do you find the information that will be valuable to you?

I regularly listen to podcasts and watch YouTube videos. Many are up to an hour long. I often don’t have the time to consume the entire episode in one sitting; it takes two or three. Many times, I’m not interested in significant parts of the conversation. Some of the YouTube channels I subscribe to include a table of contents, so I can jump to the exact minute/second mark of the interview that has the information I want to hear. Most don’t, though, and I end up listening to lots of content I could have done without. It’s also hard to go back and find the relevant information unless I take a detailed note of the exact minute/second mark in my personal notes.

Today I listened to a founder who’s trying to solve this problem. He’s helping people find relevant information on long-form content platforms faster.

This is a great next step and could transform how people learn. If more people can find the information they care about and consume it faster, the speed at which people are able to self-educate could drastically increase. People learning faster could have broad implications for society and help close some historical gaps.

I’m excited about what this founder is building and can’t wait to watch his journey.

Part of being a founder is having some rough days. Nothing will be going right. Just when you think it can’t get any worse . . . it does. It can feel like you’re being kicked while you’re down. The reality is that this is par for the course. You can’t eliminate bad days—that’s out of your control. What you can do is change how you react to them and minimize the mental toll they take on you.

I listened to a seasoned founder describe how he thinks about bad days. He said that everybody’s bad-day survival rate is 100%. He believes eventually you get out of your bad day—as long as you wake up the next day. It’s an interesting way of saying that this too shall pass.

I totally agree with this founder. When you have a bad day, keep in mind it’s just that. A bad day. You’ve had many good days, and you’ll have them again. Don’t dwell on the bad day or let it throw you off mentally. Tomorrow is a new day and a fresh start.

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.

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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