#21 - Jake Singer: Embracing Serendipity on the Internet
Listen Here: Apple | Spotify
My guest today is Jake Singer. Jake recently left a successful career at Amazon to pursue the serendipity of the internet. One of his first pursuits was starting a Substack titled The Flywheel. In it, Jake uses the concept of a flywheel as a framework to understand and analyze companies he finds interesting. In each article he explains how and why a company has gotten to where it is today, and what their flywheel suggests about its future. Jake has written pieces on companies like Zillow, Stitch Fix, and On Deck, among others. While he only started writing in August of this year, Jake already has about 2,000 subscribers. I'd say he's onto something.
In this episode, Jake and I discuss serendipity on the internet. We talk about his decision to leave Amazon, his experience with On Deck, and some of the companies he's written about. After you listen, I highly recommend signing up for The Flywheel and following along on Jake's journey. I guarantee you’ll be seeing more of him.
Selected links from the show:
Find Jake on Twitter, read The Flywheel, check out his personal website
Serendipity on the Internet by Jake Singer
What's On Deck for Business School by Jake Singer
Zillow and the Innovator's Dilemma by Jake Singer
Stitch Fix's Long Thread by Jake Singer
Show notes:
01:45 - The potential of serendipity on the internet
07:25 - Why Jake left his career at Amazon
18:26 - Designing your lifestyle to be able to take risks
24:00 - Jake's experience with On Deck
"The most tangible thing I'm walking away with are relationships with really awesome people."
32:55 - What are flywheels and why does Jake write about them?
36:22 - On Deck's flywheels and how they feed into one another
44:00 - Zillow's flywheel and how it could be potentially disastrous
52:35 - The Stitch Fix flywheel
56:41 - How Jake is thinking about monetizing The Flywheel
1:03:35 - The opinion Jake changed his mind about
1:05:45 - Jake's unusual interest
1:06:56 - Jake's thoughts on social media
1:11:18 - Jake's advice to a recent college grad
1:12:40 - Where you can find and connect with Jake
