Rebuilt From Rejection Into a Billion-Dollar Model w/ Michael Loeb
Billion Dollar Moves™ with Sarah Chen-Spellings | Global Venture Capital
Incubating Priceline from Synapse
Michael describes how Synapse incubated Priceline, the Piggly Wiggly analogy for self-serve travel, and early IPO volatility.
Fired at 36 from his dream job at Time Inc., Michael Loeb turned rejection into the billion-dollar spark behind Synapse and Priceline.com.
A true serial entrepreneur, Michael shares how he reinvented industries—from magazine subscriptions to online travel to healthcare—and why he believes the entrepreneurial gene shows up long before the first startup pitch.
In this week's episode, we unpack the mind of a founder who built and sold multiple ventures, now running Loeb.nyc, a venture collective redefining how startups are scaled.
Packed with wisdom on resilience, reinvention, and legacy, this episode is a masterclass in building with capital and conviction you won't want to miss!
Timestamps/Key Takeaways
0:00 - Intro
01:48 - From Firing to Fortune: Turning a corporate setback into an $800 million exit
05:12 - The Entrepreneurial Gene: Why the lemonade stand still predicts success
09:30 - Synapse to Priceline: Inside one of the internet’s most iconic startups
12:03 - Betting on Healthcare Before GoodRx: How ScriptRelief scaled to millions
14:39 - Reinventing the Model: Building The Loeb.nyc — a venture collective under one roof
17:44 - Legacy & Family: Raising entrepreneurs and building impact that lasts
20:23 - Billion Dollar Questions
About Michael Loeb
Michael Loeb is a serial entrepreneur and the founder and CEO of Loeb.nyc.
After starting his career at Time, Inc., Michael co-founded the Synapse Group with then partner, Jay Walker. Under Michael’s direction, Synapse grew to become the largest seller of consumer magazine subscriptions worldwide, with its revolutionary and patented Continuous Service Model. Michael and Jay went on to form and incubate Priceline.com together at Synapse, leveraging a shared team of operators and capital.
When Synapse Group was sold to Time Warner in 2006, Michael formed Loeb Enterprises with partner, Rich Vogel to ideate and develop new business concepts. The largest of those ventures was ScriptRelief, a pharmacy discount provider that has a membership in excess of 12 million Americans.
In 2019, Loeb Enterprises rebranded to Loeb.nyc and boasts a portfolio of over 18 direct investments, most of which execute from Loeb.nyc headquarters in Manhattan. Under Michael’s visionary leadership, Loeb.nyc has established a new model for startup investments. By pairing exceptional strategic and executional talent with passionate founders, Loeb.nyc significantly de-risks startup launches.
Michael sits on the board of several non-profit organizations and is an avid philanthropist. He currently resides in New York City with his wife and children.
Follow Michael:
-
Billion Dollar Moves Podcast | The Top Global VC Podcast for Founders & Funders | Backed by HubSpot Podcast Network
In venture, every move can make—or break—a billion-dollar outcome. Hosted by Sarah Chen-Spellings, award-winning entrepreneur, investor, and venture insider, Billion Dollar Moves pulls back the curtain on the strategies, stumbles, and breakout moments that define the world’s most iconic companies.
From boardroom power plays to investor backchannels, you’ll hear the untold stories behind iconic companies like YouTube, Canva, and Vimeo, and go inside the minds of those moving capital at firms like Sequoia, Lightspeed, and beyond.
Whether you're chasing your first $10M—or your next billion—this show is your front-row seat to how the smartest founders and funders win. Think raw, unfiltered, no-BS insight—designed to help you move faster, smarter, and bolder.
This isn’t just another business podcast. This is your billion-dollar playbook.
PODCAST INFO:
Podcast Website | Watch on Youtube | Join the Community
FOLLOW SARAH:
The AI-powered Podcast Player
