02 Jun Episode 3: Dan Shipper
The Scorecard is Learning
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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
- Follow @danshipper on Twitter
- Dan’s blog: danshipper.com
- This 23-Year Old Built and Sold his Startup While he was in School (First Round Review)
- Why are you in Such a rush? (Danshipper.com)
- Would I do this for 10 years? (Danshipper.com)
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?