Bobby Brannigan: How I Went From $250k In Debt To Bootstrapping A $100M Business

The Dealroom with Shamus Madan

In this episode, Shamus Madan chats with Bobby Brannigan about his entrepreneurial journey, from his father's grocery store to stock trading and textbook business. They discuss Bobby's innovative strategies, business financing, handling lawsuits, and market competition. Bobby shares his personal journey, including a life-changing backpacking trip and the influence of mentorship. The discussion ends with insights into scaling a business and Bobby's decision to sell his venture.

Not too long ago, Bobby Brannigan was over $250k in debt, and at the same time, his new company was being sued by four of the biggest textbook publishers in the US. The business was on the verge of bankruptcy. But he climbed out of this hole and built his business to $100 Million in sales. Here's how he did it.

Learn more about his new business, Mercato, here: https://www.mercato.com/

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(0:00) Introduction and Bobby Brannigan's journey into entrepreneurship (7:55) Insights from Bobby's early experiences, including working at his father's grocery store and stock trading (11:54) Bobby's start into the textbook business and strategy for success (18:40) Bobby's realization leading to a new business idea and its initial success (22:30) Discussion on market changes, competition, and innovation in Bobby's business (26:45) Financing the business, facing lawsuits, and navigating challenges (34:17) Bobby's personal journey: from a backpacking trip to reassessing the company's direction (36:16) Overcoming age-related challenges and implementing a student-to-student marketing program (40:17) Scaling the business, customer feedback, and decision to sell the business (46:59) Bobby's advice to young entrepreneurs and the importance of finding a mentor (50:23) Wrap up and end of interview