177: “Don’t scale too soon” — On Books and Mission-Based Business-Building with Readwise Cofounder Daniel Doyon

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 💻 Access Free Time episode transcripts on Podscribe » 🌟Enjoying the show? The best way to thank us is by leaving a rating or review. ❤️ Join Jenny’s private BFF community for access to a monthly Q&A call, a private podcast feed with bonus content, and a community forum to exchange ideas and feedback with fellow Heart-Based Business owners. 💌 Subscribe to the Time Well Spent newsletter: http://itsfreetime.com/join 🛠 Get instant access to the Free Time Toolkit: http://itsfreetime.com/toolkit 💬 I’d love to hear what’s on your mind! Take the Free Time listener survey ☎️ Submit a voice question or comment for future episodes: http://itsfreetime.com/ask 🎧 Make sure you’re subscribed wherever you listen to podcasts 📝 Check out full show notes from this episode and share it with a friend: https://itsfreetime.com/episodes/177 Learn more about your ad choices. Visit megaphone.fm/adchoices