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

• Success – A friend shared an interesting perspective with me. Wildly succeeding in one part of life and failing miserably in others averages out to a failure in his book. The people who succeed in multiple areas of life are who he looks up to.
• Progress – I haven’t had the bandwidth to work on a personal project for a while, but I made significant progress this week. Felt good to start moving it forward and socializing it with friends.

Week one hundred twenty was a slower-paced one. Looking forward to next week.

I was recently booked on a flight that was canceled. I spent an extra night in that city. The cancellation was last-minute, which upset the passengers (me included) because it could have been communicated earlier to allow passengers to pursue alternatives. Instead, we spent the next two hours rebooking and trying to figure out where we’d spend the night. As I watched this, I got the impression that the airline had more flights booked than it could fulfill and was operationally overwhelmed. I’ve since read several articles about how this problem has gotten worse across various airlines this summer. Customers are upset and employees are frustrated.

I have zero airline experience, but it appears that airlines are at a critical juncture. If they don’t get their operations under control, they risk losing customers and employees. It’s hard to operate a business without revenue from customers and people to do the work.

I’m not sure how airlines resolve this, but I’ll be curious to see how it pans out. And I look forward to the day when flights are running on time again.

I caught up with a founder recently and we talked about his frustrations. He shared that he’s been having a hard time the last few months. A laundry list of things aren’t going his way—from product, to customers, to managing his team. Some are the result of subpar decisions on his part. So many things aren’t going as he anticipated that it’s starting to wear on him mentally.

He asked my thoughts on his situation, and I shared my founder experience with him. On my journey, there was a pattern: when lots of things weren’t going right and my frustration level was peaking, I was usually on the cusp of a big breakthrough or material change in the business.

For example, we cut off one of our main suppliers because we weren’t aligned culturally. This caused us to start burning cash at a rapid rate. Tensions were high. We had some runway because of cash reserves, and I still believed in what we were trying to accomplish and in our team. Just when we were approaching max pain from cash burn, we identified a new supplier more advanced than our previous one. That situation set us up to go on a growth tear, and we scaled to eight figures in revenue.

When nothing is going right, be mindful that you’re likely on the cusp of a breakthrough if you push through!

I recently met with folks running an emerging fund who shared some interesting insights about their fundraise strategy. Their existing portfolio is performing well, and they’re out raising a new fund. They targeted $50 million, but because of recent market conditions they think they’ll land at $25 million. They’re adjusting the portfolio construction. They plan to do fewer investments and are raising the bar on what it takes for them to make an investment.

I wasn’t surprised to hear that funds are reducing the amount of capital they’re raising, given the macro environment, but the higher bar for investment was surprising given the success of their investments.

Risk aversion has ballooned, and founders should be aware of this and plan accordingly. We’ll eventually move back to embracing more risk, but I believe that will be a gradual process.

I chatted today with a friend who’s in a different industry. I enjoy talking to people outside of start-ups and tech for a different perspective. Our conversation naturally touched on the current macro state. He shared something interesting: in his industry there’s always demand for quality, regardless of what’s going on in the world. People putting out a quality product aren’t affected by the macro environment.

My buddy makes a great point that founders should be mindful of. If you’re solving a problem with a quality product that creates value for customers, customer demand will be there. And with authentic customer demand comes the potential to build a large company—you will be able to get capital from investors to scale.

Focus on quality and things will likely play out in your favor, even in a questionable macro environment.

Earlier this week, I shared my takeaway from an interview of coach Mike Tomlin. A friend read the post and pointed out something else that we had a great discussion about. Tomlin shared how impactful working with Tony Dungy was. Tomlin was a 28-year-old new coach in the NFL and also a new father. He was nervous and not sure if he had what it took to succeed in either role. He specifically pointed out that a big part of his nervousness was due to not knowing what to expect—he’d never worked in the NFL and wasn’t raised in a two-parent household.  

Tomlin had dreams and aspirations and was working hard to make them happen. But he didn’t know what it looked like to be a successful NFL coach or a good father. Dungy showed him not only what each looked like but also what it looked like to do both at the same time. Dungy led by example, which gave Tomlin proximity to success and changed the trajectory of his career and his life.

Tomlin is a great example of the impact of proximity to success. When you can see people to whom you relate succeed, it starts to make the impossible feel possible!

Some solutions to problems that have the biggest impact on our lives seem obvious once we’re using them—though not before. Summoning a stranger to pick you up in their car or renting a room from a stranger both seem unremarkable now that we’re doing both. But a few years ago, they were nonobvious opportunities that many thought had no chance of succeeding. Uber, Airbnb, and a variety of other impactful solutions have changed how we live our lives and are each worth billions of dollars.

Evaluating a nonobvious opportunity for investment is hard. It requires investors to focus on what they stand to gain if things go right, not all the possible reasons for failure. And before investors can evaluate these opportunities, they have to find them.

I suspect that more nonobvious opportunities from great founders with the potential for outsize returns exist, but the network problem in VC prevents them from being funded. If this problem can be solved, I see more solutions being built that will have a material positive impact on society and create outsize returns for the limited partners that back these founders.

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

• Vacation – This week felt like it was moving slowly. Lots of people were out on vacation or trying to get back into the swing of things.
• Half-day session – I spent half a day hunkered down in a conference room working on a project with someone. We got more done in that one day than we would have in two or three weeks’ worth of meetings. This was a good reminder of the value of focused in-person sessions.
• No meetings – Another week with no meetings for an entire day. Keeping this up through the end of the month to establish the habit.  

Week one hundred nineteen was a slower-paced week. Looking forward to next week.

Had a great chat with an investor today. We discussed why some founders struggle when they transition out of big organizations. He shared an observation with me: Employees working at larger companies who don’t have founder friends but want to be a founder tend to focus on working hard at work. They miss the mark on building an outside network—so, when they start their company, they don’t know anyone who can help them.

As I listened to this investor, I thought about my early days as a founder. I quit a job in a big company, only to realize that I didn’t know anybody who was building a company. It felt like I was the lone man on an island. I eventually sought out other early startup founders, we formed a cohort, and my trajectory changed completely.

If you aspire to building a startup, start seeking out people who are building companies or who support people building companies. They will be instrumental in helping you navigate the entrepreneurial journey.

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?”