Podcast Summary: The Money Mondays

Episode: "This $500,000 MBA Degree is WORTHLESS" – David Gutman 💰 EP140
Host: Dan Fleyshman
Guests: David Gutman (serial entrepreneur & course creator), Anna (mentee/intern)
Release Date: September 22, 2025

Episode Overview

In this provocative episode, Dan Fleyshman hosts serial entrepreneur David Gutman and his young mentee, Anna, to dissect the true ROI of elite business education versus real-life entrepreneurial experience. David dramatizes his conviction by smashing his own $500,000 Wharton MBA degree, arguing most business schools are no longer the key to success. Anna represents a new generation opting out of the traditional college path, seeking mentorship and practical experience instead. The discussion spans mindsets, making money, investing, giving to charity, and how to carve out alternative, more empowered career paths.

Key Discussion Points & Insights

1. Who Is David Gutman?

• Bio (01:44):
  • Experienced entrepreneur (35+ years), Brown CS undergrad, Wharton MBA
  • Multiple successful exits: one eight-figure, one nine-figure
  • "Three-time Inc. 500 entrepreneur"
  • Launching a new course: The Anti-MBA: What the Wharton Business School Never Taught Me (02:09)

2. Anna's Journey: The Unconventional Path

• Anna was an intern hired for “grunt social media work,” but impressed David enough for him to offer her a majority stake (51%) and full control over a new venture while she’s still in community college (02:19).
• Anna: "I was planning to go to college...just so happened that I couldn't afford it...David showed me that...my lifelong dream...of becoming an entrepreneur...can actually come true much earlier than I thought." (03:56)

3. The Mindset Behind Making Money

• Scarcity vs. Abundance (05:51):
  • David: "Something like 80% have a scarcity mindset...that's the biggest thing that holds most people back, is mindset."
• Anna on Risk:
  • "No risk, no reward, that is my mentality...rather than working the 9 to 5." (06:46–07:43)
• Dan on “Tasting It” (08:10):
  • Intern, try projects, don't just guess at your career. Experience before committing.

4. Building & Exiting Businesses

• Exiting:
  • David stresses knowing your end goal from the start and running a truly good business keeps your exit options open and on your terms (09:18–10:32).
  • "If you're running a business that's really profitable now, all of a sudden you can exit on your terms when it makes sense." (09:57)
• Dealing With Golden Handcuffs, Stock, Timing:
  • Cited real-world examples from the 2008 crisis and how careful planning protected sale value (11:08–12:53).

5. Youth & Money: The Perception Versus Reality

• Anna: "It's not about the money. I'm doing this for experience, I'm doing this for knowledge, I'm doing this for the people." (13:16)
• Chasing money versus chasing opportunity, experience, and relationships.

6. Investing Strategies

• David:

  • Major early believer in Bitcoin; now keeps an “insane percentage” of his liquid net worth in crypto and angel investments where he mentors teams (14:13).
  • Invests in people and founders, not just asset categories.

• Anna:

  • Inspired by David, wants to invest in businesses and leaders she admires, not interested in real estate or traditional assets (15:09).

7. The $500,000 MBA: Why It’s "Worthless"

• Cost Analysis (16:23):
  • David breaks down the all-in cost of his Wharton MBA — now double what he paid, about half a million dollars.
  • (Glass-smashing moment): David physically smashes his degree as a statement:
    • "Here’s what I think about my Wharton MBA." (17:19)
    • Dan: "That's your actual degree."
    • David: "This is my actual degree that I spent a quarter of a million dollars on." (17:31)
    • Dan: "Well, there's a half a million dollars on the floor." (17:52)
• Core Message:
  • "The reason people that went to Harvard were successful was because they got into Harvard, not because Harvard taught them useful things...It's the selection criteria." (18:06)
  • Elite education is an "illusion"—success comes from personal qualities, not the institution.
  • "The best security is investing in yourself and your capabilities." (19:12)

8. Advice for Parents & Students

• David’s Daughter:
  • Tried to dissuade her from college, suggested investing the money instead.
  • Encourages students to network with professionals, “taste” the industry before investing in a degree (19:39–21:33).
• Anna:
  • "If you really think about the data and the logic...it just makes so much sense. But yeah, [my friends] wouldn't approve." (21:38)

9. The Anti-MBA Course & Mastermind Model

• Filtering for Entrepreneurs:
  • 4.5-hour course leading to mentorship calls; the top students are invited to an exclusive mastermind, with funding (up to $500K) for the best ideas.
  • "I'm really evaluating them and their business idea." (22:24)
  • "At the end...we're going to evaluate...and invest in no less than one and no more than three..." (23:57)

10. Philanthropy as a Life & Leadership Ethos

• David:
  • “Servant leadership” and mentoring provide personal fulfillment.
  • "Nothing feels better than being useful to people." (24:15)
• Dan:
  • Details of his world record-setting toy drive, emphasizing that giving time/energy matters as much as money (25:11–26:10).
• Leadership-by-example in philanthropy:
  • "You have to lead by example, right? People...pay attention to what you do." (26:10)

11. Inheritance Philosophy

• David won’t focus on percentages, but on ensuring his daughter has enough to be secure, free, and self-reliant—calculating $5–8 million as a trust “to never have to worry about money” (26:59).

12. Money & Motivation for the Next Generation

• Anna:
  • Observes friends with trust funds split into two camps: those who want to build their own wealth, and those who coast.
  • “...those who want to supersede their parents...and those who believe their parents' money is their money. The ones I do have...are the most driven.” (28:16)

Notable Quotes & Memorable Moments

• David on Mindset:
  • "I think that's the biggest thing that holds most people back, is mindset." (05:51)
• Anna on Risk:
  • "No risk, no reward—that is my mentality...that's why I want to spend my life building something great rather than working the 9 to 5." (06:46)
• David on Elite Schools:
  • "They're benefiting from the illusion that it actually matters...It's the selection criteria." (18:06)
• Glass-Shattering Moment:
  • Dan: "That's your actual degree."
  • David: "This is my actual degree that I spent a quarter of a million dollars on." (17:31)
• David on Parental Advice:
  • "Let me put the money I was going to spend in bitcoin. She'd be sitting on $8 million right now." (19:39)
• Anna on What Drives Her:
  • "I'm doing this for experience, I'm doing this for knowledge, I'm doing this for the people." (13:16)
• David on Life’s Meaning:
  • "If people understand that...for your life to have any meaning whatsoever, you have to focus on something that's bigger than yourself." (24:15)

Important Timestamps

• Intro & Purpose: 00:15–01:42
• David’s Background: 01:44
• Anna’s Introduction: 02:19
• Avoiding the College Path: 03:56
• Mindsets & Barriers to Wealth: 05:51
• Learning by Doing / "Tasting It": 08:10
• Exiting a Business: 09:18–12:53
• Investing Approaches: 14:13
• Cost of Elite Business School: 16:23–17:52
• Elite School “Illusion”: 18:06
• David’s Advice to Parents: 19:39–21:33
• Anti-MBA Course Structure: 22:24–23:57
• Charity & Leadership: 24:15–26:10
• Inheritance Philosophy: 26:59
• Wealth, Motivation, and Upbringing: 28:16
• Closing Remarks/Find David: 29:09

Summary Takeaways

• Elite business degrees are far less valuable than most realize—real-world experience, the right mentors, and risk-taking are more critical for success.
• Mindset matters more than credentials—most are held back by scarcity thinking.
• It’s no longer risky to skip college or take the path less traveled; in many ways, it’s safer and more rewarding.
• Investment—whether in assets, companies, or yourself—should prioritize people and purpose, not just profit.
• Giving back, mentoring, and servant leadership are vital for personal and business fulfillment.
• Career and life pivots are not just normal—they’re necessary as you grow and change.

Find David Gutman: The David Gutman Podcast on YouTube (Linktree in bio) (29:09)
Audience: First-time founders, failed entrepreneurs, corporate professionals seeking transition.

“The reason people that went to Harvard were successful was because they got into Harvard, not because Harvard taught them useful things...It’s the selection criteria.”
– David Gutman (18:06)

“No risk, no reward. That is my mentality…that’s why I want to spend my life building something great rather than working the 9 to 5.”
– Anna (06:46)