Writing

“One man with conviction will overwhelm a hundred who have only opinions.”-Winston Churchill.” Have I ever told you my favorite venture capitalist joke? (h/t Kristy M) Why…

Today Valinor announced it has raised $13m in funding from Pelion, Harpoon, CRV, and others. We could not be more thrilled to co-lead this round with several incredible investors.…

Honey Health announced it has raised $7.8M to build AI Agents for the healthcare back office. Pelion is fired up to lead the round and I could not be more excited to join the…

Redo announced it has been named as a Forbes / Bessemer Rising Star - one of the top 20 startups best positioned to join their famous Cloud 100 list. It’s an incredible list with…

Today Vector announced it has raised over $61m, with a vision to build the next great modern defense tech company. We at Pelion are very proud to have led Vector’s series A, and I…

For the past year I have tried to compile the top lessons I have learned from my Dad. There are so many. Everyone who knows him will agree that he is a uniquely amazing person.…

I have been fortunate enough to work for 3 exceptional startups, invest in a few more, interview several on our podcast, and over the last 3 weeks, attend the board meetings of…

In December 2024 I was perusing twitter (as I am fond of doing) and came across this company, Agree.com. Not long after I sent a DM to Marty Ringlein, the co-founder and…

I’m excited to share the 2025 Exceptional Startups List today. You can see the list here. A few quick highlights to share: 240 startups made this year’s list - up from…

Everyone who invests in startups has their own set of criteria. This is mine. I call it the captain and the current. It goes without saying, but the goal of this framework is to…

Venture capital is like a dating pool, and I believe there are two ways to “win” the dating pool. Buckle up. This post is going to piss a lot of people off. But I think it’s…

There is a certain type of startup executive that I’ve developed an allergy to. It is what I call the empty suit executive. These are the types of leaders who are above the…

It might surprise you to hear that the most common advice I share with founders - by far - is that they should avoid venture capital altogether. And it’s not some test, or a…

We’re excited to share a few announcements about our plans to invest at the seed stage at Pelion. But first, some quick context. Pelion has been around for over 30 years…

Redo announced some incredible things today: a $24m dollar series A from great investors, unbelievable revenue growth over the past 18 months, a suite of 4 live products on the…

Remi announced a $21m Series A today, led by Pelion, after an incredible year of 650% growth and strong profitability. I am extremely excited to join the board along with Todd…

“Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win.” –Sun Tzu I have come to believe that one framework is more…

Over the past several years I’ve learned a valuable lesson over and over again: world-class is just the best we’ve seen. What do I mean? Let me give you a few examples. I…

Jump announced today that they’ve raised $4.6m from Sorenson, Pelion, and other angels to bring incredible AI experiences to financial advisors. We are fired up about what Parker,…

“I can carry on playing at this level because I like hitting the tennis ball.” -Novak Djokivic Have you ever watched the show ‘Alone’? It’s wild. They put a bunch of…

I’ve seen the future and it is electric. In 2021 I hopped on a zoom to catch up with my friend, Nate Walkingshaw. I had followed Nate’s career for many years - he is one of the…

My next “what I learned from…” series is from one of the best venture capitalists of the last 20 years, Peter Fenton. My learnings come from two sources. I watched his…

I have written about the elements of exceptional startups. This post is slightly different. I want to share what I think is the most important trait of a successful startup. By…

A few weeks ago I listened to a podcast with Alfred Lin on Turpentine VC with Erik Torenberg. It was excellent. Here are the top 17 things I learned, with a few sentences of my…

Something weird happens to people when they get an important job, like becoming a manager at work or a politician: they start talking differently. Weirdly. Less like a human. It’s…

One of the most common venture capitalist beliefs is that a product must be 10x better than the alternative to be an interesting investment. I have spent many hours thinking about…

Why does someone invest their cash into a tech company? Or into anything, for that matter? The answer, of course, is so that they can get more cash back, later. Funny…

I’m going to start a new series of posts where I share my learnings from the most interesting people I study. This will help me retain what I learn, and I hope it’s also fun to…

In his excellent book “Margin of Safety”, Seth Klarman tells a story of a famous bubble you probably haven’t heard of: the sardine bubble in Southern California. There is an…

A few months ago I posted this on LinkedIn: Several people wanted to know what I meant by “exceptional startups”: I have been a part of 3 exceptional startups…

There’s a common question that many founders often obsess over and ask of VCs: “What metrics do I need to hit for you to invest?” It’s a logical question. After all, if I can…

“Greater love hath no man than this, that a man lay down his life for his friends.” -Jesus (John 15:13) I have been thinking a lot about what it means to be a friend. This…

There is a good scene in Men in Black where Will Smith and Tommy Lee Jones talk about aliens living among the humans. The full clip is here, but the notable part is this: Will…

One of my favorite leaders is Mike Krzyzewski, the former head coach of Duke basketball. He consistently yells the same phrase at his team, after nearly every possession in a game…

8 steps to operating excellence The word “operator” is often used to describe someone who works on the business day-to-day (as opposed to, say, an “investor”). But what defines…

[This story appeared in Quillette in March 2019] At dinner not long ago my daughter and I had a standoff. She refused to eat something — a calzone in this case — because it…

Be careful about the customer An interesting question any product person faces is “when should I rely on my customers for product feedback, and when should I not?” After all,…

The lucky story of how I wound up at my dream job(s) in Silicon Valley In June it will be 2 years since my wife and I moved to Silicon Valley with our 2 kids. We absolutely love…

This is the second post in a series about Product Management. Click here to read the first In a 1997 developer conference Steve Jobs was confronted by an upset attendee. Steve’s…

My learnings as a PM, part 1 In many ways product management is counterintuitive. For example, your product is more likely to succeed if it strongly appeals to a small segment of…

“I drove by the fork in the road and went straight.” -Jay-Z Why do humans gravitate to and obsess over politics? Simple: our brains are wired this way. It’s…

When I played baseball and we had team conditioning, there was one workout that many of us dreaded the most: wall sits. For those who aren't…

Last month I wrote about my list of favorite mental models. Perhaps my very favorite, and most commonly used, is adverse selection. There’s a reason for this: adverse selection…

One of my favorite thinkers and investors, Charlie Munger, said this: "Worldly wisdom is mostly very, very simple. There are a relatively small number of disciplines and a…

[Disclaimer: This post represents my personal learnings on the subject of valuing companies through various sources like twitter and the CFA curriculum, and is in no way…

I recently watched the movie 'Whiplash' after reading that Kobe Bryant called it one if his favorites and Kyrie Irving wrote the movie title on his game shoes. It's an incredible…

So, you're trying to better compare the CFA exams vs. a top-tier MBA? Some articles argue that the CFA has a chance of replacing the MBA, and others think that's not likely. The…

A few months ago I read a tweet from Elon Musk, CEO of Tesla, that had me shaking my head: The guy was going to push a button to release some new software code and have it…

It's not every day you get a chance to learn from a four-star general. So when I received an email from the MBA registrar at Cornell University's Johnson Graduate School of…

I’m not an investing guru, but I love learning about investments and was crazy enough to take the CFA exams. Among my friends, several of whom don’t share my passion for finance,…