E173: Billionaire Michael Loeb on Risk, Innovation, and Never Giving Up

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.

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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 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