In business, everyone wants to win. But sometimes it’s the people who refuse to lose who end up finding success. This is the mindset that food writer, author, and founder of the website Serious Eats carried with him throughout the ups and downs of his career. This tumultuous journey is also the primary focus of his latest book Serious Eater: A Food Lover’s Perilous Quest for Pizza and Redemption. In this interview, Levine shares the details of how he got into food writing, experimented with media platforms to diversify the way he told stories about food, and ultimately bootstrapped the money needed to launch Serious Eats. From struggling with being profitable to testing his tolerance for risk, Levine shares the sacrifices he had to make to keep his company alive for the eight years leading up to its sale. If you want an unflinching look at the challenges of entrepreneurship, this is your chance. Levine speaks with candor about the toughest aspects of launching a startup and dispels the most common myths around starting a business. Key Takeaways Why Levine published his first book, New York Eats, while working his day job at an ad agency How the book kickstarted Levine’s career as a food writer The various media platforms, from TV to radio, he experimented with to expand the way he told stories about food How Levine’s desire to control his own fate creatively and financially inspired him to launch his first blog in 2005 The journey to bootstrapping enough money to launch Serious Eats Levine’s struggles with making Serious Eats consistently profitable Why knowing the limits of your (and your partner’s) tolerance for risk is critical The financial and emotional costs associated with bootstrapping a business How Levine’s childhood experiences contributed to his “refuse-to-lose” mentality with Serious Eats How Serious Eats organically attracted up to 8 million unique visitors per month and was eventually sold in 2015 Why the startup mantra of “fail early and often” didn’t apply to this 52-year-old digital entrepreneur A sneak peek into Levine’s book Serious Eater: A Food Lover’s Perilous Quest for Pizza and Redemption, which captures the unspoken side of starting a business Why Levine believes the most important business lessons can’t be learned without starting a business How Levine defines success Final thoughts on what it took to build a tribe of people who are passionate about food