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 [email protected].

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-- 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 [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