I connected with someone who’s successful and super busy. During our meeting, I asked a favor. I was thankful that he gave me time on his calendar and had low expectations of his doing me the favor. But I asked anyway because the answer is no 100% of the time you don’t ask. He agreed to do it, but I still figured he wouldn’t.

To my surprise, he did. It took my nudging him a bit, but he came through. We caught up afterward, and I asked him why he took the time to do something for me. I expected some deep reasoning, but it was quite simple. He said most people who ask him for something never follow up. When they don’t, he knows they’re not serious. I took action by nudging him, so he knew I was serious.

My takeaway is that having a bias toward action and following up with people in a thoughtful manner can set you apart. Most people don’t take this extra step to see things through. It’s something simple but powerful that anyone can do.  

As a kid, I had lots of dreams and ideas. Regardless of how bad or outlandish the idea, my mom always listened and encouraged me. She let me know I could do or be whatever I wanted if I set my mind to it and worked hard. Her encouragement during my formative years gave me a solid foundation and the confidence to pursue entrepreneurship (and all my other ideas, good and bad) over the years.

Happy Mother’s Day, Mom! I appreciate your love and support!

The last two years have been interesting ones for companies. Founders who were well positioned for the revenue redistribution did extremely well. Revenue skyrocketed for some of these businesses as customers sought solutions to new challenges. I’ve been chatting with some of these founders. Some of them are starting to see early signs of their customers’ habits changing again. The customers they acquired in the last few years are beginning to redistribute their revenue again.

This poses an interesting problem. These founders scaled up their companies around this new customer segment, which became a large percentage of their overall revenue. Sales, marketing, etc. are all optimized for this segment. They thought their ideal customer profile was made up of these customers because so many of them willingly and rapidly paid for their solutions. Now, they’re starting to see these customers churn as life trends toward historical norms.

These founders have a dilemma. It’s beginning to look like the house they thought they were building on a concrete foundation was built on slow-moving sand. They have significant expenses for the scaled-up organization. Do they redirect their teams to go after a different customer profile? What does the ideal customer profile now look like? How long will it take to redirect the team? These and many other questions will need to be answered by many founders in the next year to eighteen months. I’m curious to see how founders handle this dilemma—I suspect that many will shrink their teams to reduce burn until they have more clarity on these questions.

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.

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?