OP #322: Be the Person Who Shows Up

How being on the ground, watching a few too many mid-major games, and knowing when to trust what you've seen won me the bracket pool... and reminded me why showing up still matters.

Author

Darren Herman
April 07, 2026

We're going to go in a different direction today. Let's see if this works... and if so, or not, please let me know. Just reply to this email. I read and reply to each note. May take me a minute, but I'll get back to you.

For those wondering, no, I’m not going to Watches & Wonders this year. I will have severe FOMO next week when y’all are there enjoying all the new releases and celebrating Tudor’s 100th Anniversary. However, I’ll be at Possible in Miami for a hot minute - if you are there on Monday April 27, I’ll be glad to say hi. I am moderating a panel that early afternoon before heading to the airport.

Before we begin, here a few links to get us started:

If anyone is interested in trying my new gym training app, check out DudleyGym and request a waitlist spot and I’ll admit you. This is an app that’s meant to provide workout recommendations, taking the hassle off of writing your own routines. Happy to explain more if anyone has questions… just reach out.

Be well, do good.
Darren

Information Asymmetry Won Me My Bracket

So... I won my NCAA men's bracket survivor pool at work. And most interestingly, contrary to what you might think, I did not use any AI to help me achieve this.

How did I win?

A ton of luck. But one bet paid off the entire bracket. What was the bet? I picked a 12 seed I'd seen play two or three times. I knew the story. I knew their heart. I saw the writing on the wall for the upset.

But…this isn't a story about winning an NCAA pool. It's about putting in the time, effort, and diligence to set yourself up to succeed in whatever it is that you’re doing.

Early in my career, I was everywhere. There wasn't a tech conference or MeetUp in NYC that I wasn't at... and frankly, many were a waste of time. But for the ones that weren't, I was there, I met a ton of people, and I knew what was happening in the market. I was on the ground.

One of my mentors used to tell the story of a fashion company that would send staff to parties. Why? The CEO wanted to know what everyone was wearing and drinking. If the alphas were all gravitating toward something, it was a good bet that brand or item would be next season's hot product. But to get that information asymmetry, you had to be there.

For this year's pool, I had a shot at selecting High Point University in their first round matchup against Wisconsin. If you've never played a survivor or eliminator challenge, it's different from a traditional bracket. You pick one team per day of the tournament. You can't select the same team twice. The key strategy is to try and predict an upset early as you’ll need the safer bets later in the tournament.

I'd seen High Point play multiple times over the last couple of years. I knew the team. I knew their heart. And I knew how badly that school wanted a first round win. They'd never won one before, and this was their second straight year in the tournament.

They won. It wasn't a blowout. It was close, right to the end. But HPU wanted it and the school needed it.

Because I'd put in the work, I knew it and believed.

Here's the lesson for operators and investors: get out of the office. Get off the Zooms. Get into the field, the store, the product, the room where the customer actually is. There is an enormous amount of insight sitting in the world, uncaptured, waiting for whoever shows up. Most people don't show up.

Be the person who does.

** btw, luck is more important than anything. but second to luck, is showing up and putting in the work.

*** HPU won by 1. The game could have gone either way. Heck, the kid who hit the game winning shot had not hit a 2-pointer all season (he was a 3pt specialist). BUT, I knew they wanted it.

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Tokenmaxxing (Tomasz Tunguz Blog)

AI's Bundling Moment (Tomasz Tunguz Blog)

Modeling The AGI Economy (Continuations)

Thanks again for subscribing to the OP. I hope you enjoyed this letter. Feel free to reach out if you think I can make it better. Or just want to say hi.

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