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