Decisions, Discomfort and Confrontation
Your life experience is a sum of a million tiny decisions. Often it takes a long time for the impact of many decisions to show themselves. In my life, it’s...
Your life experience is a sum of a million tiny decisions. Often it takes a long time for the impact of many decisions to show themselves. In my life, it’s...
Every Valentine’s Day there are random people in front of a gas station selling last minute gifts. Last weekend it was a couple with a table in the parking lot of a...
What it means to be human in 2025.
This is a post from my regular friends newsletter.
Your life experience is a sum of a million tiny decisions. Often it takes a long time for the impact of many decisions to show themselves. In my life, it’s...
Most of the amazing outcomes in my personal and professional life have come when I favor an interesting path over a sensible one and most of my regrets can be...
Earlier this year Zack Kanter introduced me to Andrew Youderian who is, among other things, the founder of Ecommerce Fuel. Later in the summer, at the tail end of my...
According to Facebook a lot has happened since I last logged into Facebook. Strangely, I feel fine. On a random Sunday a few months ago I decided to break a habit loop...
One of our company managers sent a note to shareholders the other day that included an ask for advice. Several underperforming team members had recently resigned and he was considering...
Derek Thompson is one of my favorite writers. His work criss-crosses between economics, psychology and marketing in often wild ways. His piece on the history of the construct and perception...
The New Yorker has a great profile of Clayton Christensen, author of The Innovator’s Dillemma. I’m not sure when it came out, like many things it may have been sitting in my...
The nav said turn right. It was a dirt road. It went straight down and disappeared into trees. I checked around. There’s no other road. It had to be that...
Note: this is a part of an email and real life conversation I am having with a friend about people living with terminal diagnoses. After sharing my thoughts on When Breath Becomes...
I stumbled across Edge.org last fall thanks to a friend’s recommendation. Each year it presents a question to a group of experts across a massive number of scientific fields. Last...
I learn so much by reading annual reports. Most of the reports I read are from companies whose size dwarfs anything we have ever invested in (or might ever invest...
This was part of an internal discussion about advice to give a SaaS company that I felt worth sharing. There is a limited lifespan for microservices built with an outside platform dependency....
I wear a $10 watch. It’s a Casio. It tells time. It doesn’t display the date. It has a scratch on it from a recent surfing crash in Ventura…the same...
I’ve been thinking about this topic a lot recently. Since a large part of our thematic focus (and portfolio share) is focused on the configuration of the retail store the...
I’ve been doing detailed blood tests every quarter for the past year. The first test was a part of a 30 day measurement experiment to quantify the impact of eliminating alcohol from my...
Recently I’ve been enjoying the Hardcore History podcast from Dan Carlin. It’s an odd podcast as each episode averages 3-4 hours. Each episode is the equivalent of a short audiobook. I listen...
A journalist emailed me a question about our view that founder health is as if not more important than anything else. From Our View: Healthy people build healthy companies. A...
Here’s another email I sent to our portfolio company leaders last week. When I checked in last week I failed to include an additional company we’ve had the pleasure of...
I’m en route to spend a week with startups in Tbilisi, the capital of Georgia (the country not the state). I was invited to join a group from Silicon Valley...
I sent this email to our portfolio company leaders today. Hi everyone, I hope you’re having a great summer. I wanted to take a minute to welcome a few new...
As commerce seed investors an important factor for us to consider is whether the company will be able to raise a later Series A. This isn’t a popular thing to...
Seth Godin is among my favorite thinkers. He has a way of whittling down subjects to their critical essence. He cuts the bullshit with a very sharp knife. He recently did...
From The Off-Price Market Is Switched On, Apparel News He also estimated that in the last two decades the competition has driven down the price for off-price goods. Goods are at...
Kevin Kelly is a fascinating figure. His work and how he organizes his life always inspires me. I’m almost finished with his newest book, The Inevitable: Understanding the 12 Technological...
I have this light friendship with a person, let’s call him Bob. And every time I ask Bob what’s new, he replies “Oh, you know, millennials.” He analyzes millennials for a living. I don’t...
Last week I was traveling in Boston to spend time with two of our portfolio startups. I spend a fair amount of time with Ministry of Supply. It’s one of...
Last week my good friend Peter posted an interview with me on his epic podcast Slow Hustle. I was his first guest last year and came back for a round...
This morning I read a fantastic New York Times including the email correspondence between Natalie Portman and the NY Times correspondent. Apparently, Hotmail was responsible for the loss of years...
I enjoy observing politics through a behavioral lens. Regardless of the issue the way we do things can be baffling if you can separate yourself from the issues and just...
For the first time in my life I’m conflicted about the prospects for the future. I’ve always felt that sanity could overcome hype. Or least contain the impact. In news, election and...
Amazon Link Read Jan 2016. Review June 2016. This review is late. I incorrectly assumed I wrote down my thoughts on this book some time ago. I can’t believe I...
A founder asked me what benchmarks we want to see before we consider a company ready for seed investment. This was my answer.
Investor/company relationships are for the long-term.
I obsess over the magnitude of the global logistics industry. In the startup world we focus so often on consumer-facing companies because they make sexy stories…they’re relatable. As technologies and efficiencies have improved, the demand...
I encountered a strange phenomenon starting last fall. When I ran into people I don’t see often or otherwise communicated with them, they would say “I didn’t know you still...
Amazon Link Notes from Audiobook listening: Keystone habits are things like a regular gym routine. Around that, if executed well, healthy eating, less smoking, less drinking occur. YMCA example of...
To figure out the best way to meet investors, take lessons from dating.
There is nothing I can do right now with results of a primary in a random state other than post a snarky Tweet. Since I'm not an active day trader,...
We are not programmed to want things that are bad for us. We do not specifically need Jack In The Box.
I’ve had an intense week thanks to a scheduling snaffoo that essentially booked a meeting every hour, on the hour, several days this week. So my writing has been sporadic as has...
A few weeks ago I bought something from a startup. The company is two years old but thanks to a big bump in exposure was surely seeing an unexpected surge...
What do you do if you have a nagging problem you simply can’t figure out how to solve? You try a new approach. You rinse, repeat and try again. Imagine standing at the...
Yesterday I hung out with my good friend Lorenzo at Geekdom / 80/20 Foundation in San Antonio. As always it was a ton of fun and inspiring to see the growing...
Consultants have a habit of saying “we” when talking about company strategy. They co-opt themselves onto your team and make suggests like “we should target that market” or “our revenues are...
Last August, after a few months into living my optimized nutrition lifestyle (I need to come up with a better name) I wanted to start exercising more frequently. I needed accountability and a...
I notice patterns and cadences. It’s something I’ve always had a thing for. Travel is full of patterns. The only thing keeping the ballet of chaos that is the American air...
I recently did office hours with 500 Startups. Their most recent SF batch is astoundingly awesome. I met with a few SaaS companies and we talked about pricing. I’ve given...
Hi everyone - I hope you had a great week. This week I nerded out a bit more than usual, spending more time on topics that will make dinner guests think...
Every Valentine’s Day there are random people in front of a gas station selling last minute gifts. Last weekend it was a couple with a table in the parking lot of a...
Jeremy Phillips missed a very important point in his Friday NYTimes piece The Rise and Fall of the Unicorn. It’s a point most overlook when considering the impact of a number...
When you sell memberships that guarantee a physical service, you are mostly in the business of financial engineering. The price you charge has to cover your costs and generate a profit but has...
I stumbled onto this question on Quora: My startup has traction, revenue ($600k/year), and profit! It is a scalable model in a multibillion dollar industry. We are based in the...
The role of government regulators grew in the early part of the 20th century. Regulators serve two purposes, sometimes but not always concurrently: Protect workers and protect consumers. Their rise made sense at the time....
To be a great company a company must first be a company. Companies that redefine industries were first good at one simple thing. Southwest changed how people view airlines and...
Elon Musk wasn’t the first to discover that trashing multi-million dollar rockets is inefficient.