I spent part of today talking through—in depth—some complex ideas with a friend. These were ideas I’ve been thinking about on my own. I shared what I believe, and why. He challenged some of my thinking, which I appreciated. And he gave me his perspective, based on his experiences. All this led to some insights neither of us anticipated. I walked away with some great insights, more clarity of thought, and increased conviction.

Looking back, some of my greatest breakthroughs weren’t the result of my thinking about something in isolation. They came from using sounding boards—that is, from sharing my thoughts with people I consider strategic thinkers. We fed off each other in those conversations, and the result was something better than I could have come up with on my own.

If you’re trying to do something great, make sure you have sounding boards. Two heads (or more!) are usually better than one.

This weekend, I’ve listened to friends discuss the macro environment. One of my big takeaways is that there’s an aversion to risk right now. Everyone is focused on the downside and avoiding losses. This happened fast. Eight months or so ago we were at all-time highs in public markets. Many were leaning into risk as valuations continued to rise. They were focused on the upside.

It's fascinating to watch risk tolerance change so quickly. For many, it took years to warm up to embracing risk and upside. But it was only a matter of months before the focus shifted to risk avoidance.

I can’t predict what’s going to happen with the macro market, but I’ll be watching closely. I’m curious to see when people will begin to lean into risk again. I suspect that those who take a contrarian position and embrace risk before the masses will set themselves up for outsize returns.

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

• Differing perspectives – This week was a reminder that there’s value in hearing differing perspectives. Hearing someone else’s perspective helped me think about something differently and slightly adjust a strongly held opinion.
• Contrarian viewpoints – I spent some time listening to successful people who’ve taken contrarian views that led to outsize success. It’s a very interesting approach. I’m curious about these folks and intend to study them more.
• No meetings – I blocked off a day with no meetings. It was great. I was able to go deep and be productive. I want to work in one of these days every week.
• Leveling up – I want to make sure I’m always learning and leveling myself up. I need to continue putting myself in uncomfortable situations so I can grow. This week was a reminder that discomfort leads to insights and growth.

Week one hundred seventeen was a steady and productive one. Next week will be busy. Looking forward to it.

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I was listening to the author of The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley. Jimmy Soni conducted countless hours of interviews to understand what happened at PayPal and what made it such a special place to work. One of the interesting insights from his research was that brutal honesty was a superpower. A few takeaways from his interview:

• Disharmonious – People at PayPal challenged each other regularly when they saw things differently. To this day, these people challenge things they believe are incorrect, and they’re not shy about it.
• Intensity – They believed it’s dangerous to say critical things behind each other’s backs. They shared critiques directly with the person in question, and it made the company better.
• Not personal – They didn’t take disagreements personally. Disagreements are not about the person—they’re about the flaws in the analysis or thinking around an idea. They wanted to get to the best idea.
• Respect – You want people you care about to improve. Being direct and honest is a sign of respect and care that helps them improve.
• Rare – It’s rare to find an environment where people are totally honest with one another.

I’m a fan of people being honest and direct with others in a respectful way. Debating differing perspectives leads to better outcomes overall. I personally enjoy it when people around me provide honest, direct feedback that doesn’t require interpretation.

Based on this interview, I’ve added Soni’s book to my reading list. Can’t wait to check it out.

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I talked to someone today who was an early employee at a now publicly traded company. He shared an observation that stuck with me: some companies won’t ever be more than what they are today because they won’t (or can’t) level up.

He elaborated on this: Having big goals and dreams are great. But to do the impossible and enjoy outsize success, you must level up as a founder and as an organization. If you don’t level up, you will stall or struggle. As an early employee of a company that went on to be worth billions and to be publicly traded, he saw firsthand what it means to level up and how it can lead to success.

I totally agree. A buddy framed it well: the biggest throttle on your success is how fast you can improve yourself. This applies to founders and to companies.

I enjoy talking to founders about how they see the future because they see it differently than everyone else does. To them, it’s not predetermined. Or even filled with limiting factors. It’s white space. Meaning that whatever they can dream up, they feel they can turn it into reality. They end up working hard to create the future they envision. It’s a different mindset that has an impact because it drives innovation and change in society.  

Founders, what future do you want to build?

I listened to an investor share the best pieces of advice he’s been given. The one he discussed the most was about choosing whom to work with. His mentor told him life’s too short to work with people you don’t love working with. The investor went on to describe how that piece of advice shaped his selection process across the board (LPs, founders, team members, etc.).

I agree with this investor’s mentor. Life is short. You want to spend time working with people you enjoy working with. One thing that the mentor left out, though, is that working relationships are bidirectional. As much as you may want to work with someone, they must want to work with you, too. The feeling may not be mutual—at first, at least. If you’re in this situation (and lots of people are), work to position yourself in such a way that others will want to work with you. And understand that can take time. Sometimes an interim step is working with people who aren’t your first choice so you can gain credibility to set yourself up to work with your first choice. The important thing is to have a target—to know whom you want to work with—and understand what you need to do for them to want to work with you!

I’ve been doing all kinds of entrepreneurial things since I was a kid. Some of them were crazy. As long as they weren’t too far out there or unsafe, my dad supported my pursuing my ideas, even though he wasn’t an entrepreneur. He did whatever he could and even got his hands dirty to help me get some of them off the ground. His encouragement was pivotal and led to my embracing entrepreneurship. I’m thankful and appreciative that he’s always been so supportive.

Happy Father’s Day, Pops! I appreciate the love and support. Couldn’t have done it without you.

Having strong opinions can be a positive trait for successful people. The tricky part is that no one is right 100% of the time. No matter how strong your opinion is about something, you could still be wrong. Actually, depending on your line of work, you can be wrong a lot and still be successful. For example, if you’re an investor and wrong 50% of the time, you’ll be considered a great investor with a strong track record because you can make many times more than you invested on winners, while losses on losers are capped at the amount you invested.

If you have strong opinions, try to have the humility to recognize when you’re wrong. It’s easier said than done. One way to do it is to stay curious and keep learning about the topic you’re so confident about. Talk to people (ideally people whose perspectives differ) about it. Read about it. All while keeping an open mind. As you learn, your conviction will increase or decrease. If it decreases substantially, you should consider the possibility that you’re wrong.

There’s nothing wrong with having strong opinions about something and being wrong. It happens to everyone. Recognizing that your strong opinion is incorrect and course correcting quickly is what sets you apart and earns you respect.

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

• Growth – I was reminded this week that growth comes from being in uncomfortable situations. Going forward, instead of focusing on the discomfort I’ll remind myself that I’m growing. I think this mental reframing will help me lean into more situations that will help me grow.
• No meetings – Last week, I blocked off an entire day with no meetings. I was hoping to repeat that this week, but I gave in to meeting requests. What a difference! I want to work toward consistently have one meeting-free day every week.

Week one hundred sixteen was a good one. Looking forward to next week.