Life never gave us lemons (Ricky Weekly #101)
This is where I share 3 things every week with my friends and anyone else interested.
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A picture from my life:
I went on a bachelorette party trip! I feel special being part of a bridal party. Boys and girls can be so different it’s a fun topic to think about.
A thing on my mind:
Whenever I’m down about work, I like to say to myself, “I CHOSE this.” It’s a powerful reminder of my tremendous luck and privilege to do what I love to do, and that I can always choose something else.
Then I ask myself if I still love what I do. People have asked me, “is this your life’s work?” I hope it’s not that serious. Sounds like a trick question to me, as if we are only meant to do one thing. My answer is always, “who knows!”
I fell in love with startups in college. 15 years later, I know much more about it and I still love it. Most days I wake up excited because I get to do something challenging that has potential to teach me something about how to shape our world. Business is a big, competitive game with very few rules that affords me maximum degrees of freedom and scorekeeping to tell me what I’m made of. Can I fall out of love with it at some point? Sure. It’s really hard and I’ve sacrificed a ton. So I have to always be checking to make sure it’s still worth it.
Am I good at it? No. Not yet, at least. I’m not nearly as good as I believe I could be. One of the hazards of this job is that you can’t easily get the reps to improve a particular skill (ie if your startup isn’t scaling, you don’t get to work on hiring skills). Another one is that the actually important skills are too meta* and hard to work on (eg seeing opportunities and knowing how to capture them). Either way, regardless of how good you get, luck plays a very significant role in the outcome, which makes this all very unsettling but also very appealing. You have to constantly be working to figure out what actually matters for your business, charting paths to your best ability for those around you, and being willing to run full speed ahead of everyone knowing where you’re going is most likely off the cliff.
Should you succeed as a founder, you’d have created a system. You can hire employees to operate with reduced uncertainty for a predictable result, and they get to showcase and refine their skills in that context to produce the result more effectively. But at the end of the day, the uncertainty is only reduced for everyone in the system to the extent the business is successful. Job security is a fantasy. Markets are alive and changing faster than ever. Just over the last few years we went from one of the longest bull markets in tech to massive layoffs due to economic uncertainty and AI disruption. The founders are the ones staying up every night in good times and bad studying the market and thinking about the customers to figure out how to move in the direction of opportunity. Founders trade certainty and security for resilience and agency.
Still, founder life is hard. I’m plagued by insecurities. What’s been useful for me over the years is to stop believing in the successful founder archetypes. Bill Gates. Steve Jobs. Jeff Bezos. Mark Zuckerberg. Elon Musk. Their successes have led to an entire industry pattern matching for roughly the same type of brilliance: intellectual horsepower/rigor, precociousness, brazenness/daring, visionary-ness, a little unhinged with a side of the tism. As an ambitious nerd, this is admittedly what made Silicon Valley feel like home to me. These are qualities historically undervalued by society. But it’s a trap to think they’re the only attributes that hold any predictive power. For too long I’ve discounted many of my strengths for not matching up to this archetype. Now I know better. Among all the pattern matching, founders and companies need to be differentiated enough to win. I think for me to really do that well, I need to embrace who I am.
*Footnote: the “meta” skill of business is not so meta according to this article by Cedric Chin. It’s a different type of learning that you can think of as “sensemaking” — useful when learning from real world experiences where feedback loops are noisy, delayed, might not even exist. There are ways to get better at “sensemaking” through constant reflection and being agile enough about updating your priors. Here’s a related article from Brian Lui on the dangers of tight feedback loops. Really, really cool stuff.
A piece of content I recommend:
Why Relationships Die & Which Ethnicity is WORST in Divorce on Flagrant by Andrew Schulz and Akaash Singh
I’m a new fan of Andrew Schulz and Akaash Singh, so I’ve been gobbling up all their content. The podcast’s pretty sweet. Good comedians have superpowers because they can cross the line and take conversations to places they don’t normally go. The topic of divorce is not something people like to talk about and here’s two and a half hours of it in exhilarating depth with a wide variety of perspectives. Another good episode is the one with 50 Cent talking about…Diddy. Yup. They’ve also talked to politicians like Bernie Sanders, Pete Buttigieg, Eric Adams, Vivek Ramaswamy if you’re into that.
Bonus Content: I have a bunch this time, so a sentence to introduce each.
If you love San Francisco, you’ll love this explainer of SF’s map and how it came to be.
This is like Jiro’s Dreams of Sushi but for ramen lovers.
A Chinese YouTuber interviews her grandfather about growing up in the communist revolution. I think this is a pretty rare first-hand account.
A very adept conversation about trauma between Peter Attia and Jeff English.
A fun reminder that we are the source of our problems (and the title of this newsletter).
If you’re looking to eat better, Eric Topol interviews Kevin Hall who used to be a Senior Investigator at the NIH and looked into ultra-processed foods, among other things in our food environment.
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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.