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

• Attitude change – I noticed a shift in people’s attitude toward investing this week. The stock market was a topic of conversation with a lot of people, which felt odd. When I talked to other investors it came up, and that wasn’t surprising, but it also came up during a few founder calls and in my friend group, which I didn’t expect. I’m curious to see what people’s attitude toward investing will look like going forward.
• Hustling – I spent this week doing a bit of strategic hustling. It’s always interesting to see how hustling can open doors that you’d never have expected.
• Labor – A friend broke down the current state of the labor market based on his hiring challenges. People think differently about how, when, and where to work. It feels like we’re in the midst of a seismic shift.

Week one hundred ten was a high-activity week. I expect next week to be more of the same.

I noticed a problem some time ago and decided to dive into it to understand it better. I emailed a bunch of people and asked others to introduce me to people who’d lived the problem. So far, a high percentage of these people have agreed to chat. The calls have all started off the same, followed a consistent path, and ended well.

People are a bit suspicious when they first hop on the call. I introduce myself and share some info on my background. I then share the problem (I frame it in a way that’s unique to my background) that I’m trying to learn more about from people who’ve lived it. That’s when the conversation changes. They warm up and start telling me all about their experience with the problem. They love talking about how the problem affected them. By the time the call ends, we’ve built the beginnings of a relationship and I’ve learned a ton. If it’s gone really well, they’ve agreed to intro me to someone else.

The most important thing I’ve learned from these conversations is that people love talking about their problems and feeling heard. If you’re a founder, take the time to talk to people—and, especially, to listen to them—to understand the problem you’re solving. The time and energy you put into this will pay you back many times over.

I had a chat with an investor today. Not only is he a successful venture capitalist, he’s personally invested in forty other emerging venture capital funds. I was amazed when I heard that number. Inspired by such a large number of data points, I asked him a question: What have you learned from these investments that surprised you? I didn’t know what his answer would be, but I was sure it’d be insightful.

He said there’s a high correlation between success and emerging fund managers who are disciplined about communicating with their LPs (people who invested in their fund). The fund managers who communicate best also run funds that have the highest returns (in his personal portfolio). It’s a small sample set but still a powerful insight.  

I’m a fan of founders keeping people in the loop via regular update emails. The upside to writing them far outweighs the downside. Based on today’s conversation, this appears to be a universal rule that applies not just to founders but to anyone trying to achieve outsize success.

In 2013 or so, I met with a founder who blogged. I enjoyed his posts and wanted to learn more. The idea of blogging interested me, but there were two hurdles I wasn’t sure how to overcome. I was an early founder trying to get my company off the ground and didn’t think I would have the time. More importantly, I’m a naturally private person. I’ve been this way as long as I can remember. I was uncomfortable with the idea of sharing my thoughts openly.

I asked that founder how he handled privacy in his blogging. He told me he was very specific about what he shared. Nothing about his personal life. Only posts about things related to business. More importantly, he understood that he had significantly more to gain from sharing publicly than he had to lose. That last part really stuck with me—that he was playing the probabilities. The upside was significantly larger than the downside. I had focused on the downside and never considered the potential unintended benefits.

Fast forward to 2020, and I finally began blogging myself. I’ve been sharing my thoughts daily for over two years. It started it as a 60-day challenge to share what I’d learned, but I’ve gotten more than I ever would’ve thought from the experience. The founder was right. I haven’t lost anything (that I know of) from blogging, but I’ve gained a tremendous amount and hopefully helped others. The upside has far outweighed the downside. Sharing publicly has been a good bet, and I plan to keep doing it.

Y Combinator released a video entitled “How Future Billionaires Get Sh*t Done.” It’s a good one for founders. One of the things it touches on is time management. They reference a popular blog post Paul Graham wrote years ago titled “Maker’s Schedule, Manager’s Schedule.”

I like Paul’s characterization of a maker schedule versus a manager schedule. When you’re trying to do something hard, big blocks of uninterrupted time are critical. Any interruption, such as a meeting, can make the entire day unproductive. Half-day blocks make sense for people on a maker schedule. On the other hand, when you’re managing people, you meet a lot and work in thirty-minute or one-hour windows, stopping and starting often throughout the day.

When you’re an early-stage founder, you’ll have to do both. As a founder, switching between mental modes too often, I struggled before I eventually learned to use lunch as a natural separator. I was on a maker’s schedule before lunch and a manager’s schedule after.

Founders should consider the maker-versus-manager concept for themselves and their team. Getting people to understand it and adopt the right schedules can have a big impact on the company’s productivity!

I spent time walking with a founder friend. One of the things we talked about were two paths to success that we’ve seen be successful. One was high activity spread across many paths, and the other was low activity focused on a single or limited number of paths.

The high-activity path is a hustler’s path. Hustlers are constantly working on a variety of things and doing lots of activities. This approach is highly iterative and reactive. There isn’t much deep reflection or many predefined goals at the outset. It’s more go where things take you. These folks are constantly evaluating what new paths to take based on the results of the last activity. They repeat the cycle until it ends (hopefully) in whatever the hustler defines as success.

The low-activity path is strategic. Strategists spend time deciding on a destination on the front end. Activities that align with the goal are taken on; those that don’t (even if promising) are declined. They reflect along the way to determine if the things they’re doing are having the desired results. They continually dissect failures and adjust. This approach focuses on a goal and tries to determine the best path to it.

We concluded that success can be achieved in various ways. These are just two we’ve seen up close that resulted in outsize success. In each instance, the person’s personality fit their approach. The extroverted and high-activity person we knew took the hustler’s path. The deep-thinking and reserved person took the strategic path.

I listened to an old interview of Jeff Bezos explaining why he decided to leave his stable job to start Amazon. Not just any job—a high-paying job at an investment banking firm on Wall Street. It was a tough decision that he ultimately made using what he described as a regret-minimization framework.

He projected himself into the future to age 80. He wanted to minimize the number of regrets he would have as he looked back on his life. An important part of his thought process was identifying the things he’d regret not trying, even if he failed. Starting Amazon was one of them—even if it meant giving up his stable lifestyle.

I’m a huge fan of starting with the end in mind and working backward. I haven’t used a regret-minimization framework, but I’ve thought about what I want people to remember me for when I’m long gone and used that as a compass when making decisions.

For those fortunate enough to be able to consider only regret, I think it could be a good way to evaluate big decisions.

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

• Focus – This week, I was intentional about carving out time to focus, and it served me well. I was able to move the needle on some important projects and have conversations about my progress with the right people.
• Multiples – I spent time working with some well-capitalized companies this week. They raised at high multiples (in historical terms) in the last year or so. Now they’re trying to figure out how to achieve the growth targets they agreed to when they raised those rounds. They’re facing some difficult decisions. I suspect more companies are in this situation. Should be interesting to see how it plays out.

Week one hundred nine was a week of focus and much activity. Looking forward to repeating that mix next week.

Founders tend to be impatient people. They have ideas, but they realize that it’s the execution of their ideas that matters. Most have high expectations around execution. They manage others with a focus on getting things done quickly. Their impatience can be a superpower, but it can also have unintended consequences.

Focusing exclusively on rapid execution at all costs can be a slippery slope. That type of management gets results, but at a cost. People burn out. The company’s culture can turn toxic. The business churns through people. The body count rises.

If you’re a founder, consider: Do you want a high body count to be part of your legacy? Does your current management style align with the legacy you want to leave behind you?

I had a conversation with an early founder who’s spent time in Atlanta’s and San Francisco’s start-up ecosystems. He’s trying to decide which will be his home base. I’m a huge advocate for Atlanta, so I was curious to hear his perspective on the two cities. He shared a variety of things, and the main thing he said stuck with me: San Francisco embraces dreamers; Atlanta embraces hustlers.

From his time in San Francisco, he learned it’s a city that respects big, outlandish visions. Even if it sounds crazy, people (investors and other founders) will support it. There’s a belief that the outlandish can become reality, have a big impact on society, and generate massive financial returns. Atlanta, he said, is a city that respects action and execution. Getting stuff done and moving things forward matter most. People prefer execution to big visions.

I’ve never heard anyone make this comparison before, and it got me thinking. I haven’t spent enough time out west to judge San Francisco, but I do know Atlanta well. I’m not sure that I agree with him. I think Atlanta embraces big-picture thinking but is also pragmatic. The pragmatism is rooted in the exits local start-ups have had. As those exits have increased in size, so have beliefs around what’s practical (for better or worse). As more founders have larger exits, I think we’ll continue to see bigger dreams embraced by the city.