Leap Academy Podcast · Episode 119 · Aug 5, 2025
Dan Shapiro
68 Rejections, One Yes: How I Built a $100M Startup Against All Odds
"After getting laid off from his corporate job, Dan Shapiro launched his first startup, Photobucket Inc."
69 minutes
Leap PodcastDan Shapiro68 Rejections, One Yes: How I Built a $100M Startup Against All Odds
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What's in this episode
After getting laid off from his corporate job, Dan Shapiro launched his first startup, Photobucket Inc. (formerly Ontela), but faced nine months of rejection from investors and no funding. Despite these setbacks, his persistence led to a successful partnership, which later turned sour due to a managerial dispute. He took these lessons and went on to build multiple successful startups, including Glowforge, a $100M company revolutionizing 3D laser printing. In this episode, Dan joins Ilana to share the secrets to startup success, how to navigate entrepreneurial challenges, and what it takes to build a company that not only thrives but also transforms industries.
Dan Shapiro is a serial entrepreneur, innovator, and CEO of Glowforge, a company that pioneered desktop laser technology, enabling creators to produce millions of custom products. He previously created Robot Turtles, the most successful board game in Kickstarter history, and founded Photobucket Inc.
In this episode, Ilana and Dan will discuss:
(00:00) Introduction
(01:56) Early Upbringing and Entrepreneurial Drive
(04:47) Corporate Experience at Microsoft
(08:14) The "Poop Umbrella" Leadership Principle
(11:42) The Darkest Nine Months of Dan's Career
(16:39) Securing Funding Against All Odds
(20:35) The Brutal Truth About Entrepreneurship
(24:32) The PhotoBucket Merger: What Went Wrong?
(27:56) From 67 Rejections to a Google Acquisition
(31:38) CEO Strategy: Delegate vs. Lead
(36:24) The Bold Strategy Behind Robot Turtles' Success
(45:16) Building Glowforge: From Idea to $100M Business
(51:47) Leadership Challenges and Ethical Dilemmas
Dan Shapiro is a serial entrepreneur, innovator, and CEO of Glowforge, a company that pioneered desktop laser technology, enabling creators to produce millions of custom products. He previously created Robot Turtles, the most successful board game in Kickstarter history, and founded Photobucket Inc. Dan also served as CEO of Google Comparison Inc. after Google acquired his startup, Sparkbuy. He is the author of Hot Seat and a prolific innovator with over 60 patents to his name.
Connect with Dan:
Dan’s Website: danshapiro.com
Dan’s LinkedIn: linkedin.com/in/danshapiro
Resources Mentioned:
Dan’s Book, Hot Seat: The Startup CEO Guidebook: https://www.amazon.com/Hot-Seat-Startup-CEO-Guidebook/dp/1449360734
Glowforge: https://glowforge.com
From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109: bit.ly/tim-oreilly-leap-academy
Bad Blood: Secrets and Lies in a Silicon Valley Startup by John Carreyrou: https://www.amazon.com/Bad-Blood-Secrets-Silicon-Startup/dp/152473165X
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Transcript
Full conversation
Transcript coming soon. In the meantime, watch the YouTube version above for closed captions, or listen on Apple Podcasts / Spotify.
About Leap Academy
Where ambitious professionals leap to their next chapter.
Founded by Ilana Golan — Forbes contributor, board director, investor in 100+ companies, and former F-16 flight instructor commander — Leap Academy has helped 70,000 people across 4 continents reinvent their careers and build lasting reputations.
- American Business Awards Startup of the Year, 2023
- Inc. 5000 Fastest Growing Company
- Featured on Forbes, Yahoo Finance, NBC, CBS, ABC

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Ilana Golan
Hosts every episode. Has guided thousands of professionals through career reinventions, leadership leaps, and brand building.
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