Greg Olsen

Hey 👋🏼 I'm Greg.

I'm a guy on the internet with too many interests. Most of them orbit around learning and writing and software and kids and books and business. This is the place I come to try to string words and ideas together and hold myself accountable.

Credentials are sooo boring. I like this list better.

  • 3 amazing kids and 1 amazing wife
  • Still goes to church
  • Splits time between Maryland and Delaware
  • Will choose a cigar and whiskey with friends over nearly any other activity
  • 45 and feels like a wide-eyed little kid
  • Like Erasmus, would choose books first over food and clothes
  • Wrote software or led software teams for a living for 20 years
  • Drove across the country in a rented RV. Twice!
  • Runs a lot
  • Raced cars and taught others how to do it
  • Has 3 half-written novel messes... a finished one will make this list someday
  • Helped build a company from 2 to 250+
  • Loves building things out of (wood | words | code | ideas)

I write on Substack too

If you've made it this far, you might like it.

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Things I've Written

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Things I'm Reading

Born Standing Up by Steve Martin
Timeless Way of Building by Christopher Alexander

6 books finished this year

Projects

  • Matreas

    Modern fundraising for schools with a story worth telling.

  • A Real Estate Project

    Coming soon.

  • The Furious Opposites

    A Both/And view of understanding technology.

  • Faradash

    Foreign spending dashboard based on FARA data.

  • CollegeValue

    Compare colleges by earnings vs. debt.

Things I'm Wondering

  • ? How are phones and AI changing the way we grow up?
  • ? How can small projects drive family revenue?
  • ? Can restaurants use spreadsheets as menus?
  • ? How do you get better at speaking?
  • ? What does it take to write a spy novel?

Recent Workouts

  • 2.36 mi Afternoon Walk, 1 day ago 44:49
  • 1.87 mi Afternoon Walk, 4 days ago 34:57
  • 3.87 mi Lunch Walk, 14 days ago 68:21
  • Afternoon Walk, 17 days ago 40:00
  • Lunch Weight Training, 17 days ago 50:00

Fresh Quotes

"When I was in justice, my ultimate vision for that part of the criminal justice system was to achieve, by means of AI and technology, what Jeremy Bentham tried to do with his Panopticon. That is that the eyes of the state can be on you at all times. Similarly, in the world of policing, in particular, we’ve already been rolling out live facial recognition technology, but I think there’s big space here for being able to harness the power of AI and tech to get ahead of the criminals, frankly, which is what we’re trying to do." — Shabana Mahmood, current UK Home Secretary
“I’ve really read all the time since I was a little kid, it’s been a lifelong thing. It’s basically trying to fill in all the puzzle pieces for the big discrepancies. A great term is ‘sense-making’. Essentially, ‘what the hell is happening and why?’ The world is an incredibly complex and erratic place and trying to figure that out ...is kind of a lifetime occupation.” — Marc Andreesen
“The advice I would give is to read everything in sight. And to start very young. It’s a huge advantage in almost any field to start young. If that’s where your interest lies, and you start young, and you read a lot, you’re going to do well.” — Warren Buffet

More in the Tumble →