What happens when you get fired from one of the most prestigious media companies in the world at age 36? For Michael Loeb, it meant inventing a new category in subscription services, launching one of the earliest venture studios, and incubating Priceline—one of the internet’s first great successes.
In this episode, I speak with Michael Loeb, founder of Loeb.nyc, about how getting fired from Time Inc. led to the $800M sale of Synapse back to Time, his early partnership with Jay Walker to incubate Priceline, and what makes a great entrepreneur. We also dive into how Loeb.nyc works, the role of trust and pivots in building companies, and why pattern-matching VCs often get it wrong.
Michael doesn’t hold back. He’s honest, funny, and full of war stories from decades of building companies—and backing founders through multiple lives.
Highlights:
- How getting fired from Time Inc. pushed Michael into entrepreneurship
- Reinventing subscriptions with continuous service and beating inertia
- The origins of Priceline and early internet innovation
- Why successful entrepreneurs are often “unemployable”
- The venture studio model behind Loeb.nyc and its high hit rate
- How to know when an old idea is worth reviving
- Why safety and trust are essential for early-stage teams
- Navigating pivots and replacing founding teams
- The evolving role of small teams in the AI era
--
Guest Bio:
Michael Loeb is the founder and CEO of Loeb.nyc, a venture collective that builds, funds, and operates startups. Through Loeb.nyc, he has helped launch and scale dozens of companies by combining capital, talent, and shared services in a single ecosystem designed to dramatically improve the odds of success.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
Stay Connected: X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Michael Loeb: https://www.linkedin.com/in/michaelloeb1/
Links:
Loeb.nyc: https://www.loeb.nyc/
--
Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.
(0:00) Episode preview
(0:09) Michael Loeb's journey from Time Warner to entrepreneurship
(2:17) The birth of subscription services and Time Warner acquisition insights
(4:07) The essence of entrepreneurial disagreeableness and innovation
(7:40) The story behind Priceline's creation with Jay Walker
(20:06) Recognizing the right timing for business ideas
(23:16) Key factors for a company's sudden growth
(27:00) The importance of adaptability and pivoting in business
(32:00) Leadership strategies in emerging companies
(34:47) Embracing reinvention for achieving product-market fit
(35:41) The role of small teams in company scaling
(38:13) Debunking the starving entrepreneur myth
(40:03) Understanding the entrepreneurial drive to succeed
(43:22) The American entrepreneurial ecosystem
(46:03) Work-life balance for entrepreneurs
(48:36) The impact of success on perception
(50:43) Michael Loeb's parting wisdom and call for ideas
(52:16) Analyzing success rates and VC partnerships
(53:53) Impact of the NYC mayoral race on the entrepreneurial scene
(56:53) Lessons from founding billion-dollar companies
(57:16) Closing remarks
