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.

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.

Stay Connected: X / Twitter:

David Weisburd: @dweisburd

David Weisburd: https://www.linkedin.com/in/dweisburd/

Michael Loeb: https://www.linkedin.com/in/michaelloeb1/

Loeb.nyc: https://www.loeb.nyc/

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

(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