Leap Academy with Ilana Golan

68 Rejections, One Yes: How I Built a $100M Startup Against All Odds | Dan Shapiro | E119

05 Aug 2025

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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 Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

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