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"Recovering Entrepreneur" Jacob O'Bryant on Building Products Full-Time, Why He Got a Job Again, and Invention as a Career Path
What happens when you chase your entrepreneurial dream for four and a half years and then realize it's not actually what you want?
In this episode, I sit down with Jacob O'Bryant, creator of The Sample (now Yakread), to talk about his journey from quitting his job in his early twenties to going all-in on building his own products, only to discover that entrepreneurship wasn't the path he thought it would be. Jacob is refreshingly honest about the psychological toll, the gradual realization that he valued invention over business-building, and why going back to a full-time job wasn't defeat, it was clarity.
We also explore the framework that sits between pure research and entrepreneurship: invention. It's a way of thinking about your work that doesn't require monetization or academic rigor, just meaningful exploration. Plus, we dig into unbundling social media: what it means, why it matters, and practical steps you can take as an everyday person to support a more open internet. If you've ever wondered whether the "quit your job and start a company" narrative is really for you, this conversation might give you a different perspective.
Resources Mentioned:
- Jacob's website: https://obryant.dev/
- Jacob's "Invention" resource page: https://obryant.dev/invention/
- Jacob's product: https://yakread.com/
- Jason Crawford's "We Need a Career Path for Invention" essay: https://blog.rootsofprogress.org/a-career-path-for-invention
- "You Can Help Unbundle Social Media": https://obryant.dev/p/you-can-unbundle-social-media/
- "Wherever you get your podcasts is a radical statement": https://www.anildash.com//2024/02/06/wherever-you-get-podcasts/
Chapters:
- (00:00) Intro
- (01:40) Being a "Recovering Entrepreneur"
- (04:30) College Was a Waste
- (07:00) The Initial Itch: Ambition and Meaningful Work
- (09:20) Planning the Leap: Money, Marriage, and Runway
- (14:50) The Sample and Yakread
- (19:10) Not Going All In Again
- (21:00) Invention is Between Research and Business
- (26:30) The First Months: Euphoria to Reality
- (29:30) Why You Shouldn't Monetize Your Passion
- (31:15) Hustle Culture vs. The Messy Middle
- (34:00) Going Back to a Day Job Wasn't Defeat
- (36:30) How Entrepreneurship Changed Jacob's Work
- (38:30) Job Searching with Entrepreneurship on Your Resume
- (42:30) Unbundling Social Media
- (46:00) What Everyday People Can Do About It
- (51:10) Final Takeaway and Resources
View all episodes
By Michael CarruthersWhat happens when you chase your entrepreneurial dream for four and a half years and then realize it's not actually what you want?
In this episode, I sit down with Jacob O'Bryant, creator of The Sample (now Yakread), to talk about his journey from quitting his job in his early twenties to going all-in on building his own products, only to discover that entrepreneurship wasn't the path he thought it would be. Jacob is refreshingly honest about the psychological toll, the gradual realization that he valued invention over business-building, and why going back to a full-time job wasn't defeat, it was clarity.
We also explore the framework that sits between pure research and entrepreneurship: invention. It's a way of thinking about your work that doesn't require monetization or academic rigor, just meaningful exploration. Plus, we dig into unbundling social media: what it means, why it matters, and practical steps you can take as an everyday person to support a more open internet. If you've ever wondered whether the "quit your job and start a company" narrative is really for you, this conversation might give you a different perspective.
Resources Mentioned:
- Jacob's website: https://obryant.dev/
- Jacob's "Invention" resource page: https://obryant.dev/invention/
- Jacob's product: https://yakread.com/
- Jason Crawford's "We Need a Career Path for Invention" essay: https://blog.rootsofprogress.org/a-career-path-for-invention
- "You Can Help Unbundle Social Media": https://obryant.dev/p/you-can-unbundle-social-media/
- "Wherever you get your podcasts is a radical statement": https://www.anildash.com//2024/02/06/wherever-you-get-podcasts/
Chapters:
- (00:00) Intro
- (01:40) Being a "Recovering Entrepreneur"
- (04:30) College Was a Waste
- (07:00) The Initial Itch: Ambition and Meaningful Work
- (09:20) Planning the Leap: Money, Marriage, and Runway
- (14:50) The Sample and Yakread
- (19:10) Not Going All In Again
- (21:00) Invention is Between Research and Business
- (26:30) The First Months: Euphoria to Reality
- (29:30) Why You Shouldn't Monetize Your Passion
- (31:15) Hustle Culture vs. The Messy Middle
- (34:00) Going Back to a Day Job Wasn't Defeat
- (36:30) How Entrepreneurship Changed Jacob's Work
- (38:30) Job Searching with Entrepreneurship on Your Resume
- (42:30) Unbundling Social Media
- (46:00) What Everyday People Can Do About It
- (51:10) Final Takeaway and Resources