Search for a command to run...

Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this special edition of the Money Mondays podcast, host Dan Fleyshman interviews serial entrepreneur David Gutman, who has achieved both 8 and 9-figure exits, and his 18-year-old protégé Anna. The episode takes a dramatic turn when Gutman literally smashes his Wharton MBA diploma to make a point about the value of traditional education. (17:14) Anna, fresh out of high school, chose to skip college and instead received 51% ownership of a new company to learn entrepreneurship through real-world experience under Gutman's mentorship. The conversation covers entrepreneurship, alternative education paths, investment strategies including Gutman's significant Bitcoin holdings from 2015, and the importance of taking calculated risks. (02:44)
David Gutman is a serial entrepreneur with over 35 years of experience, holding an undergraduate degree in computer science from Brown University and an MBA from Wharton Business School. He has achieved both an 8-figure and 9-figure exit from his companies and has been recognized as a three-time Inc. 500 entrepreneur. Gutman is currently launching his first course called "The Anti MBA: What the Wharton Business School Never Taught Me" and actively mentors young entrepreneurs.
Anna is an 18-year-old recent high school graduate who chose to forgo traditional college in favor of real-world entrepreneurial experience. Originally brought on as a summer intern, she impressed Gutman so much that he offered her 51% ownership of a new company along with mentorship. She comes from a family where financial constraints would have required community college, but she seized the opportunity to learn business directly from a successful entrepreneur.
Dan Fleyshman is the host of the Money Mondays podcast, focusing on how to make, invest, and give away money. He started his first business at 15, saving $43,000 over three years, and by age 19 was running a company doing $9.5 million in sales that eventually went public. He also organizes the world's largest toy drive and brings a wealth of entrepreneurial experience to his interviews.
David Gutman emphasizes that approximately 80% of people suffer from a scarcity mindset that prevents them from making money. (05:50) He compares this to Duke basketball players who remain confident even when trailing, versus poker players who become overly protective of their chips when facing elimination. The key insight is that truly successful people focus on optimism about winning rather than fear of losing. This mindset shift allows entrepreneurs to take calculated risks, invest in themselves, and pursue opportunities that others avoid. In practice, this means viewing challenges as growth opportunities rather than threats to your existing resources.
Rather than spending four years in college studying a field you might not enjoy, Gutman advocates for "tasting" different industries first. (08:10) This means seeking internships or entry-level positions at companies you admire - working for Damon John's clothing brand if you're interested in fashion, or Universal Records if music appeals to you. The goal is to discover what genuinely excites you before making major time and financial commitments. This approach prevents the common scenario of switching majors after two to four years, essentially losing valuable early career years. Anna's father implemented this same strategy when she considered becoming a dietitian, having her spend a month interviewing professionals in that field before making any educational commitments.
Gutman challenges the conventional wisdom that formal education is the safer path, arguing instead that building practical skills and experience creates more security than theoretical knowledge. (08:04) He points out that you're building your "talent stack" through hands-on experience rather than listening to professors who may have never actually implemented what they teach. The most successful people often dropped out of prestigious schools (Mark Zuckerberg, Michael Dell) because they were already talented enough to gain admission - it wasn't the education that made them successful. This approach allows you to always return to school if desired, but provides immediate value and skill development.
Successful entrepreneurs think about their end goal from the beginning and work backwards to achieve it. (09:22) Gutman explains that many companies generate significant revenue but never successfully exit because they didn't plan for it strategically. The key is running an exceptionally profitable business while maintaining awareness of exit opportunities, but not being married to any particular outcome. This approach maximizes your options and allows you to exit on your own terms when market conditions are favorable. Companies with capital constraints often have to exit or merge at suboptimal times, while profitable businesses can choose the best timing and terms.
Both Gutman and Anna emphasize investing in relationships and business opportunities with people they respect rather than traditional assets like real estate. (14:49) Gutman's strategy involves mentoring teams while investing in their companies, creating a "retirement plan" of businesses he enjoys with leaders he appreciates. This approach provides both financial returns and personal fulfillment through meaningful relationships. For young entrepreneurs, this means prioritizing network building and learning opportunities over immediate financial gains, understanding that relationships and experience compound more significantly than money alone.