Backed by
The Top Global VC Podcast for Founders & Funders
10M+
Monthly Reach
1M+
Impressions
Top 5%
Global VC Podcast
50k+
Global Community
Billion Dollar Moves is the first and largest traveling venture capital podcast-meets-live show, taking you inside the boardrooms and behind the scenes with unicorn founders, funders, and the power players shaping the future.
Filmed live across global innovation hubs—from Silicon Valley to Singapore—it’s where capital meets conviction, and the conversations catalyze action.
Trusted by governments, family offices, and institutional investors, Billion Dollar Moves doesn’t just talk about the future—it helps build it.
Lead, build, and invest better.
Join us as we hit the streets globally to uncover billion dollar ventures of unicorn founders & funders.
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.
Billion Dollar Moves is proud to be part of the Hubspot Podcast Network with 10 million downloads a month as a group.
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:
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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:
In venture, every move can make—or break—a billion-dollar outcome.
In venture, every move can make—or break—a billion-dollar outcome.
Panu Maulaheimo
- "We've worked with Sarah & her team to promote investing in and from Helsinki, leveraging ad spots and a sponsored series of episodes showcasing our nation's best unicorn founders and funders. Sarah's compelling storytelling combined with her targeted reach has resulted in an oversubscribed program for international investors. This was our second year working with her, and we are excited to continue working with her."
Monsha’at
- "Sarah Chen-Spellings brought her signature energy and commanding presence to Biban 2024, making her the ideal host and moderator alongside the Shark, Robert Herjavec. Her deep insights into investing in innovation and women-led ventures resonated powerfully with our audience of entrepreneurs, business leaders, and global investors. With her polished media expertise and natural ability to engage across cultures, she elevated the event, ensuring impactful takeaways and amplifying our reach across platforms. We were honored to have a globally renowned name join our stage, and we are excited to continue to work with her to drive entrepreneurship in our country and beyond."
Ann Cairns
- "We at Mastercard are delighted to be working with Beyond the Billion to address the massive gender venture funding gap holding women innovators back. Too much of our world was designed without women in mind and without women involved. Shelly, Sarah, and their team have done an excellent job of raising awareness about this issue and creating a network of VCs pledged to do more by investing in female-founded startups to address the problem. Working with our team, they seamlessly created an impactful dialogue based on Mastercard's gender balance narrative."
Why Our Sponsors Love Working With Us
This show is about unfiltered conversations about success, failure, fear and courage, in the pursuit of the next big thing in tech and venture.
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.
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.
Disclaimer
This podcast is an expression of personal opinion and does not represent the opinion of the host Sarah Chen-Spellings (SCS) as an investor personally, her firm Beyond The Billion (BTB) or any company discussed. These discussions are for informational purposes only, including any mention of securities or venture funds; and does not constitute any investment, legal, tax advice. SCS or BTB may hold currently, or in the future, direct or indirect interests in the featured companies or funds. No guarantee of any kind is implied or possible where projections of future conditions are attempted.