How to Be Ready for a Big Break

I’m delighted to welcome Daniel Doyon to the pod this week, co-founder of one of my favorite software services, Readwise. Every morning while I have my coffee, I look forward to checking out the daily email roll-up of five serendipitous snippets pulled from my entire library of Kindle highlights.

In this conversation, we cover: how Dan and his cofounder handled the famous “hug of death” from Tim Ferriss recommending their service in his 5-Bullet Friday newsletter; the perils of premature optimization and why you should do things that don’t scale; what to do when you do slam against a scale ceiling; the benefits of running a mission-oriented business; how we’re handling the progressive atrophying of our attention for reading books, and our favorite page-turners that spark joy and as Dan says, “whisk you to the end.”

More About Daniel: Daniel Doyon is the cofounder of Readwise, a reading tool that helps readers revisit the highlights from their ebooks by synchronizing and then sending a daily email resurfacing the best highlights from Kindle, Instapaper, iBooks, and more. He is also an expert in creative real estate acquisitions and partnerships, bibliophile, oenophile, and sailor.

🌟 3 Key Takeaways

• Be wary of premature optimization: Do things that don’t scale without trying to predict how your systems will break. Only once you “slam” against a ceiling should you work on solving for the next level of scale.
• Hire from your user base: You’ll find the most passionate, mission-based people to work with from your own community, people who already love what you’re creating and what you stand for.
• Minimize meetings by taking a page from Readwise’s playbook: No more than 1.5 recurring meetings per person per week. That means one weekly, and one bi-weekly—that’s it!

📝 Permission: Reset the expectations around whether or not you reply to inbound messages, and the amount of time it takes you to do so.

✅ Do (or Delegate) This Next: Sign-up for Readwise if you haven’t already! It’s a game-changer for carrying your favorite highlights forward from the books you read. Every day you’ll get a round-up email of five random highlights and a sixth suggestion from an adjacent book that you haven’t read yet.

🔗 Resources Mentioned

• Daniel on the web, Twitter, LinkedIn, Facebook
• Dan’s “whisk you to the end” book recs: Trader Joe’s Book, Doctor Dealer
• Jenny’s favorite true story page-turners about large-scale drug ops: American Kingpin by Nick Bilton (on the DPR/Silk Road build-up and bust), The Mastermind by Evan Ratliff (verticalized prescription drug and arms kingpin), Dreamland by Sam Quinones (decentralized drug trade, “Uber of heroin”)

📚 Books Mentioned

• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Rework by Jason Fried and David Heinemeier Hansson

🎧 Related Episodes

• RadReads x Pivot & Free Time
• 111: Building a Second Brain with Tiago Forte
• 084: Sprinkling the First 1,000 Serendipity Seeds of a Launch
• 017: Serendipity as Business Strategy with Leanne Hughes

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