She Saw What NO ONE ELSE Did: How Lindsay Kaplan Build a $1 Billion Company
Thu Jan 15 2026
What does it take to turn a so-called “cringe” idea into a billion-dollar company?
In this episode of 30 Years in 30 Minutes, host Michael Oved sits down with Lindsay Kaplan, co-founder of Chief, the premier executive network for women, to unpack how she saw opportunity where others saw embarrassment. From her early days in publishing and brand storytelling, to helping build Casper into a breakout direct-to-consumer giant, to ultimately co-founding Chief and scaling it into a $1B company, Lindsay shares the real lessons behind modern entrepreneurship.
This conversation dives deep into founder mindset, storytelling as a business weapon, building powerful networks, choosing the right co-founder, raising venture capital, and why great entrepreneurs don’t chase trends — they redefine them. Lindsay explains how embracing discomfort, leaning into “uncool” industries, and understanding human psychology helped her build brands that people actually care about.
If you’re an aspiring founder, operator, marketer, or investor looking to understand how billion-dollar companies are really built — this episode is a masterclass in vision, conviction, and execution.
🎧 Listen now to learn how Lindsay Kaplan turned a “cringe” idea into a category-defining company.
Don't forget to like and subscribe. Follow us on Instagram, X, and LinkedIn: @30in30pod.
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What does it take to turn a so-called “cringe” idea into a billion-dollar company? In this episode of 30 Years in 30 Minutes, host Michael Oved sits down with Lindsay Kaplan, co-founder of Chief, the premier executive network for women, to unpack how she saw opportunity where others saw embarrassment. From her early days in publishing and brand storytelling, to helping build Casper into a breakout direct-to-consumer giant, to ultimately co-founding Chief and scaling it into a $1B company, Lindsay shares the real lessons behind modern entrepreneurship. This conversation dives deep into founder mindset, storytelling as a business weapon, building powerful networks, choosing the right co-founder, raising venture capital, and why great entrepreneurs don’t chase trends — they redefine them. Lindsay explains how embracing discomfort, leaning into “uncool” industries, and understanding human psychology helped her build brands that people actually care about. If you’re an aspiring founder, operator, marketer, or investor looking to understand how billion-dollar companies are really built — this episode is a masterclass in vision, conviction, and execution. 🎧 Listen now to learn how Lindsay Kaplan turned a “cringe” idea into a category-defining company. Don't forget to like and subscribe. Follow us on Instagram, X, and LinkedIn: @30in30pod.