Episode 3: Dan Shipper

Episode 3: Dan Shipper

The Scorecard is Learning

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Dan Shipper

Dan is a Wunderkid entrepreneur who has been building web apps since he was a kid. He went to Penn as a Philosophy major and bootstrapped his startup Firefly which he sold the same month as his graduation. So what happens to your internal monologue when you sell your company at a time when most grads are starting their first jobs? There’s the common story that says “When X happens, my life will begin.” But you wouldn’t say “I’ll start exercising once I get promoted to Managing Director?” Dan vulnerably shares deeper insecurities of social rejection, the emotional drain of self talk, and how a relentless drive to improve can be destructive. We riff on writing (how it’s like compound interest and creates serendipity), the dangers of putting off working on yourself, not doing “half a push-up” (when it comes to experimentation), and the lumpy nature of progress. And together we have a good laugh comparing how Dan and I, both nerdy, skinny and insecure teenagers hatched up detailed plans for social acceptance.

Learn More about Dan

Show Notes (in minutes)

  • 1 — First tech project
  • 3 — First “real” program, file sharing
  • 5 — First paid app FindMyPhone (on blackberry), pre-iPhone
  • 6 — Friendly Hackathons in college (pre Hackathon)
  • 9— Why major in philosophy? Some of the smartest people we know majored in Philips
  • 12— Khe did the reverse, majored in Computer Science and Econ
  • 15 — How do u think about being deliberate in building a business
  • 17— Bezos on building on 3 vs 7 year cycles
  • 19 — Boot strapped by design
  • 21 — Negative self talk; can you still optimize for learning with negative self talk?
  • 23 — You sold Firefly at 24, what’s next?
  • 28 — Don’t put off working on yourself Xxxx
  • 29— Drive to always be improving can be destructive
  • 30 — Social rejection as a motivator
  • 36 — The “problemization” of the universe
  • 38 — What are we hoping to get from the question “What is a meaningful life?”
  • 39 — Are you religious?
  • 41 — Exploring transcendence through meditation and silent retreats
  • 43 — The realization about how much “we make ourselves upset”
  • 44 — The impact of writing on Dan’s life
  • 45 — Why should I write if no one’s going to read it?
  • 48 — Importance of “routine” and a practice vs Goals?
  • 49 — Do you set goals? Khe’s challenge of “outcome” goals
  • 51 — What’s next for Dan?


Khe Hy
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Khe Hy is the creator of RadReads.