Regret Minimization, $120 Million Collapse, & More
The Friday Five: Episode XLIX
Welcome to the 897 new members of the curiosity tribe who have joined us since Wednesday. Join the 85,535 others who are receiving high-signal, curiosity-inducing content every single week.
Today’s newsletter is brought to you by Outer!
If you know me, you know that I am inspired by being outdoors. Something about the fresh air just opens me up and makes the creative juices flow. I do almost all of my best thinking and writing outdoors.
That’s why I am such a fan of Outer–the NEW outdoor furniture company with purposefully designed furniture that will help you get outdoors more. Outer makes the world’s most beautiful, comfortable, innovative, and durable outdoor furniture - ALL from sustainable materials - and is the ONLY outdoor furniture with a patented built-in cover to make protecting it effortless.
I’m sitting on an Outer sofa as we speak. You’re going to love it.
Today at a Glance:
Quote: Comfort with discomfort.
Framework: Regret Minimization Framework.
Tweet: Lessons on health and life.
Article: Managing the water crisis.
Podcast: Domm on the Fast collapse.
One Quote:
“If you have everything under control, you're not moving fast enough.” – Mario Andretti
Peak performance is found at the edge of control.
Develop a comfort with discomfort.
One Framework:
The Regret Minimization Framework
A framework developed by Jeff Bezos as part of his decision to leave a lucrative hedge fund job at D.E. Shaw to pursue founding Amazon. The foundational premise is that the goal is to minimize the number of regrets in life.
When faced with a difficult decision:
Project yourself into the future (imagine yourself at 80-years-old).
Look back on the decision you are currently faced with.
Ask simply, "Will I regret not doing X?"
Take action accordingly.
This is one of the core frameworks I use for making big decisions.
In my mind, there are two key nuances here:
Ask both sides of the regret question and evaluate them against each other. Will I regret *doing* it? Will I regret *not doing* it? Reflect on each side of the question. Turn it over in your mind. The inversion is useful.
Identify the principles and values that you will never regret pursuing or furthering. This clarifies the lens through which you think about regret in the context of Step 3. As an example, if your core principle is to provide for your family and create an environment of stability, you might regret taking a risky entrepreneurial leap much more than someone whose core principle is to leave a lasting legacy. Neither core principle is “right” or “wrong”—just very different, so require a different perspective on regret.
Note that there is definitely a hint of survivorship bias when you hear this framework mentioned by highly successful people (like Jeff Bezos). It’s often used to justify a risky decision that worked out well. Be aware of the bias and think objectively about base rates of success as you use it for your own big decisions.
One Tweet:
Really enjoyed this short thread. Three key lessons (that apply well beyond fitness/health):
Live in the Present: Stop comparing to your past or future self. You are where you are—embrace it and try to improve from that baseline.
Consistency is Key: Intensity will only get you so far. Most people need consistency more than they need intensity.
Small Things Become Big Things: Do the little things well, over and over again, or suffer the consequences.
One Article:
A Farmer’s Quest to Beat California’s Waves of Drought and Deluge
Fascinating Wired article on farmers getting creative to pull water from subterranean reservoirs in California to manage their crops during the historic droughts the state has faced.
Water shortages are becoming more and more prevalent globally—this is an issue to keep a close eye on as we continue to build towards a world of increasing abundance.
One Podcast:
Fast’s Domm Holland on What Really Happened at Fast
If you’ve been following startup or technology news the last few weeks, you’ve definitely heard about the collapse of Fast—the one-click checkout company that had raised $120 million.
I’ve been fascinated by this story ever since I saw the CEO of Fast enter a weird press conference Tokyo drift style wearing a pink blazer. I actually sent a text to a group chat asking whether Fast was a fraud immediately after watching that video, so clearly it set off my alarm bells…
This interview is worth a listen—impressive that Harry was able to get him to join right after the collapse. I’ll hold on sharing my view for now. Listen to the short discussion and you be the judge.
Listen to it on Apple Podcasts or Spotify.
Where It Happens Podcast
How to Leverage Nostalgia and Win at Marketing
Watch it on YouTube and listen to it on Apple Podcasts or Spotify.
Special thanks to our sponsors for providing us with the support to bring this episode to life.
This episode is brought to you by Outer. Spring is in the air in both NYC and Miami, and we can’t get enough of our Outer outdoor furniture. Their furniture looks incredible and is durable. Personally, we love the Outdoor Loveseat.
Right now for our audience exclusively they are offering $300 off any product + free shipping until May 1. This is one of the most generous offers of any sponsor we’ve had. Did we mention they have a 2-week free trial? Go to liveouter.com/room to get the deal.
This episode is also brought to you by MarketerHire. MarketerHire provides on-demand access to pre-vetted, top-tier marketers who can freelance as much or as little as needed.
They’ve made it easy to hire great marketers. With pre-vetted talent and expert hand-matching, you can add a proven marketer to your team in less than a week.
Go to marketerhire.com to learn more.
Sahil’s Hiring Zone
Talent Collective
Excited to announce the launch of my new talent collective! Members of the collective will get exclusive access to opportunities at my favorite high-growth startups across the tech landscape.
Completely free for candidates. Use the link here to apply!
Companies can get exclusive access to these terrific candidates by buying a collective pass here.
Featured Opportunities
Practice - Product Designer
Clipboard Health - Engineering Manager
DaoHq - Founding Solidity Developer
Artifact - Product Designer
Clay - Growth Manager
Assemble - Software Engineer
The full board with 20+ other roles can be found here!