Resist Comfort

I watched an interview in which coach Mike Tomlin described how he stays at the top of his game. After winning two Super Bowls, he still has the same fire he had when he first became an NFL head coach fifteen years ago. Tomlin shared something that really stuck with me. He resists comfort. In fact, he tells his team, “Don’t seek comfort,” because special outcomes—outsize outcomes—are the result of being uncomfortable. He explained that he views thinking back to his success as a Super Bowl champion as seeking comfort. So, he ignores his past success and the comfort it breeds.

Tomlin may ignore his track record, but it’s impressive and speaks to his credibility as a coach and leader.

Growth often comes from being in uncomfortable situations. You’re forced to think about and do things that are unfamiliar. Succeed or fail, you’ll learn from those experiences. I really like how Tomlin is intentional about resisting comfort. It tells me that he’s a learner and constantly looking for ways to improve himself and the team he leads. It makes sense that after fifteen years, he’s still at the top of his game.

If you’re aiming to do something special, consider asking yourself, “Am I resisting comfort—or seeking it—when I make decisions?”


Innovation Isn’t Just Tech

I was talking with a buddy today about his business. He shared how his solution works. At its core, he’s bringing together existing pieces to create a new solution. What he’s doing is highly complex. As we chatted, I thought: This isn’t a tech company, but it’s still innovative.

Innovation is the introduction of something new. The new thing doesn’t have to be driven by, or be, technology. In the case of my buddy, he’s taking pieces that already exist and combining them in a new way. Even though these pieces are readily available to everyone, no one has combined them the way he has. His innovation is in how he’s combined the pieces and managed the complexity of doing so.

He likely doesn’t think of himself as an innovator because he isn’t building a tech company, but he is an innovative founder.

Innovation doesn’t happen only in tech. Anyone can be an innovator if they solve a problem in a way that hasn’t been seen before. Even if it’s just combining existing things in a new way.


Happy July 4th!

Happy July 4th!

I hope everyone had a safe and healthy holiday!


Who in Your Circle Is Doing Amazing Stuff?

I was sharing my journey with someone this past week. I said that a critical part of it was meeting other early-stage founders and forming an accountability group of sorts. The person I was speaking with probed a little about why that group had such outsize influence. The answer was that the group wasn’t just talking about starting companies, they were taking action. And not only were they acting, they were executing at a high level. The results spoke for themselves.

Looking back on it, I can see that being so close to smart people doing amazing stuff was transformative. They showed me what was possible and made me push harder for what I wanted. I didn’t want to get left behind by my peers, so I leveled up.

My takeaway is that finding other entrepreneurs whom I could relate to was helpful—but finding the ones doing great things was positively transformative. Being in the presence of people doing amazing stuff increases the chances that you’ll do amazing stuff too.

Who in your circle is doing amazing stuff?


Decision-Making: Reversibility and Speed

I read an old Amazon shareholder letter recently. In it, Jeff Bezos outlined how he thinks about decision-making. He broke it down into two categories:

Some decisions are consequential and irreversible or nearly irreversible—one-way doors—and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions. But most decisions aren’t like that—they are changeable, reversible—they’re two-way doors. If you’ve made a suboptimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through. Type 2 decisions can and should be made quickly by high judgment individuals or small groups.

This framework simplifies how to think about decisions in a way that most can easily grasp.

I agree with most of Jeff’s thinking, except around speed. I think the appropriate speed for type 1 decision-making depends on the stage of the company. Jeff says type 1 decisions should be made slowly. That’s not a great approach for early-stage founders, who should be careful and thoughtful about their type 1 decisions but shouldn’t aim to make them slowly. They should try to get to 70% to 80% confidence as quickly as possible and decide. If the decision is wrong, you learn and improve your decision-making going forward. If you never make a decision or decide too slowly, you could be dealing your company a death blow.

I’m going to start think about my own decisions as type 1 or type 2 and aim to improve how quickly I make type 1 decisions.


Weekly Reflection: Week One Hundred Eighteen

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

  • Conviction – This week was a reminder that understanding why you’re doing something is critical. It helps you build the confidence to make a decision and stick with it when others don’t understand it or when things look bleak.  
  • Nonobvious markets – I spent some time thinking about this. Many markets are undercapitalized (for various reasons). Some have the potential for outsize returns. Finding these markets—or people who understand them—early is something I’m thinking about a lot.
  • No meetings – I blocked off a day with no meetings again this week. The day was super productive. I want to keep this habit up. If I can do it for all of July, I think I’ll be able to keep it going.  

Week one hundred eighteen was a calm one. Looking forward to spending the holiday with family and friends.  


Founders Are Getting Dinged Because of Terminology Mix-up Around Vision

Great founders have a compelling vision. Unfortunately, though, many early founders don’t do great job of articulating it. I think that asking early founders what their vision is trips up many of them. I suspect it’s because “vision” means different things to different people. Investors are thinking X, while an inexperienced early founder thinks it means Y. This disconnect causes people to think some founders don’t have a vision, or it isn’t compelling, when that’s not so.

Today I was reviewing the application for Sequoia’s Arc Catalyst that seed-stage companies have to fill out. The application doesn’t ask for the company vision. Instead, it asks this: How is the world transformed if your company achieves its mission?

Companies exist to do a specific thing (i.e., solve a problem). If they accomplish that mission, they will have an impact on the world.

I love the way Sequoia framed this question. It’s clear and goes straight to the point, so it avoids terminological confusion.

If you’re an early founder, be prepared to articulate your answer to “How is the world transformed if your company achieves its mission?” That’s your vision!


Give Yourself Runway to Get Time on Your Side

Today I talked with an investor who started a company as a side project. He knew that a particular problem existed because he lived it. It was a problem he was passionate about. He decided to work with his cofounder nights and weekends to get the solution off the ground. It was almost four years before the timing was right for their company to take off. Macro events shone a light on the problem, and lots of people were suddenly in search of a solution. The company has since raised capital and is thriving.

My big takeaway is that timing markets is incredibly hard, even for an investor. You need the right problem but, to gain traction, you also need the timing stars to align. Founders should be mindful of timing and give themselves runway. This investor’s approach was to give himself enough runway by keeping his day job. He had no idea when the timing would be right, but he and his cofounder kept building as they patiently waited. Giving themselves enough runway proved to be a prudent decision.



Reflect as You Build

Talking to an investor, I asked what he’d learned during his journey to raise his fund. He was honest. He said he hasn’t had time to reflect but probably should. He’s been in build mode, getting his firm off the ground. He’s moving fast and has a lot on his plate. As we discussed some of the hurdles he overcame, he uncovered some great insights that will inform his journey going forward. He mentioned that he might have changed course while he was building if he’d stopped to reflect earlier.

When you’re building something, it’s natural to be heads-down executing. I did this myself as an early founder. But every so often, it’s helpful to spend time thinking about what’s worked and what hasn’t worked, and why. You’ll connect dots and uncover insights that improve your decision-making and allow you to course correct and refocus your execution on the most impactful activities. This practice will improve your chances of being successful.



Ten-Year-Long Overnight Success

Today I had a chance to get to know the entire team at a venture capital fund. I had a great chat with the founding partners, who shared their origin story with me. One of the things that stood out was that it took almost a decade for them to refine their investment strategy and begin to gain material traction. Today the firm has a strong, growing team and strong investment returns.

This firm’s history is another data point reinforcing the fact that overnight successes don’t exist. A lot of time and energy precedes success. Unfortunately, most people aren’t paying attention to the groundwork. The attention usually comes when all the hard work pays off.

If you’re building something great, be ready to spend a material amount of time building it without attention or accolades.


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