Success Story Podcast with Scott D. Clary

Episode: Lessons - Why Passion and Grit Aren't Enough | Michael Dermer - From Wall Street Lawyer to Serial Entrepreneur
Date: September 18, 2025

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In this “Lessons” episode, Scott D. Clary talks with Michael Dermer about how entrepreneurial thinking is not just beneficial for startups but crucial for individuals and organizations at any stage. The conversation centers on why passion and grit aren't enough for sustained success, and explores the importance of bringing entrepreneurial skills and perspectives into both startups and established companies. The discussion also covers handling innovation inside bureaucracy, finding trustworthy mentors, and Dermer’s “Four P’s” framework for understanding entrepreneurial mindset traps.

Key Discussion Points & Insights

1. Entrepreneurial Mindset Isn’t Optional—It’s Essential

• Entrepreneurship is a Skill for All: Dermer argues that thinking like an entrepreneur is not just for those starting companies, but is an essential skill for employees in any organization, especially large, established ones ([00:54]).

  • Quote: “Entrepreneurism is not nice to have. It's a skill that must be unlocked in every company.” — Michael Dermer ([00:00])

• Why Big Companies Fail to Innovate: Traditional organizations are focused on quarterly numbers and struggle with innovation. The lack of entrepreneurial thinking leaves them vulnerable to being disrupted by more agile competitors ([00:54]).

  • Example: “Amazon should not exist, right? Walmart should have created Amazon, and Blockbuster should have created Netflix, and Sony should have created Spotify…” — Michael Dermer ([00:54])

• Need for Training: Dermer discusses his “Think Like an Entrepreneur” program, which helps corporations bring entrepreneurial principles into their culture ([01:40]).

2. How to Present Innovative Ideas in Bureaucratic Organizations

• Deliver Results, Not Just Ideas: Advancement in corporations comes from delivering measurable results. Senior leaders seek credible innovations that can produce outcomes ([02:24]).

  • Advice: “Do your homework...come up with a business plan, come up with a business case...but say this, I believe that this can deliver us revenue, competitive differentiation, significant cost savings. And I'd like to have the opportunity to present it to you.” — Michael Dermer ([02:24])

• Initiative Pays Off: Even within red tape, employees are encouraged to gather evidence, make a compelling case, and proactively seek an audience with decision-makers.

  • Quote: “The people that rise to senior levels...are the ones that are able to deliver results.” — Michael Dermer ([02:24])
  • Scott’s summary: “You'd be surprised at what you can accomplish if you start going out there and, like you said, acting like an entrepreneur within a company...” ([03:52])

3. Breaking Rules & Getting in Front of Senior Leaders

• Proactive Outreach Works: Dermer shares a personal story of leaving voicemails late at night for CEOs of large health organizations—an unconventional method that paid off ([04:26]).
  • Quote: “If you go to somebody and say, this is how you really win or this is how you really lose...they will break all the rules for you.” — Michael Dermer ([04:26])

4. Finding the Right Mentor

• Beware of Self-Serving Mentors: Many purported mentors are more interested in their own business interests than truly helping mentees ([05:55]).
• Seek Objectivity: Dermer recommends involving a trusted, objective outsider to vet a potential mentor or hire, serving as a sanity check to avoid decisions colored by stress or emotion ([05:55]).
  • Quote: “Go ask a colleague of yours...whose business judgment you respect and say to them, hey, listen, I'm thinking about getting involved in this mentor. Can you talk to them for a half hour, an hour? Because they're completely objective...” — Michael Dermer ([05:55])

5. The Four P’s: Pressure, Passion, Pleasure, Pain

• Influences on Perspective: After selling his company, Dermer identified four forces that skew an entrepreneur’s outlook: pressure, passion, pleasure, and pain ([08:29]).

  • Pressure: External expectations, deadlines, financial constraints.
  • Passion: The founder’s deep belief in their vision (sometimes to a fault).
  • Pleasure: The euphoria of early wins.
  • Pain: Rejection and setbacks.
  • Quote: “We're always under the influence of these four P's that make us do the wrong thing when we're under pressure...when we're feeling our passion...sometimes we’re not listening...So we just always have to be really cognizant of the fact that we’re kind of under the influence of these things...” — Michael Dermer ([08:29])

• Real-World Examples:

  • Hiring mistakes made under pressure.
  • Ignoring market feedback due to passion.
  • Emotional swings after both wins and setbacks.

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |---------------|-------------|-----------| | 00:00 | Michael Dermer | “Entrepreneurism is not nice to have. It's a skill that must be unlocked in every company.” | | 00:54 | Dermer | “Amazon should not exist, right? Walmart should have created Amazon and Blockbuster should have created Netflix and Sony should have created Spotify.” | | 02:24 | Dermer | “The people that rise to senior levels...are the ones that are able to deliver results.” | | 02:24 | Dermer | “Do your homework...put it in a package...say this, I believe that this can deliver us revenue, competitive differentiation, significant cost savings.” | | 04:26 | Dermer | “If you go to somebody and say, this is how you really win or this is how you really lose...they will break all the rules for you.” | | 05:55 | Dermer | “Go ask a colleague of yours...to talk to them for a half hour, an hour. Because they're completely objective...” | | 08:29 | Dermer | “We're always under the influence of these four P's that make us do the wrong thing when we're under pressure...when we're feeling our passion...sometimes we’re not listening...” |

Important Timestamps

• 00:54: Dermer explains why entrepreneurial thinking is essential for large organizations
• 02:24: Tactics for presenting innovation inside bureaucratic companies
• 04:26: Story about cold-calling health insurance CEOs, illustrating the power of bold outreach
• 05:55: Discussion on finding and vetting mentors, and the value of objective second opinions
• 08:29: Introduction and explanation of the “Four P’s” framework

Episode Takeaways

• Entrepreneurial thinking benefits anyone, anywhere—whether launching a startup or driving change inside a Fortune 500.
• Tangible results and preparation are key to getting buy-in for new ideas in established companies.
• Seek mentors and new hires with input from trusted outsiders to avoid emotionally-driven mistakes.
• Pressure, passion, pleasure, and pain all distort perspective—recognizing their influence is crucial for resilient, strategic decision-making.

This episode offers practical wisdom for entrepreneurs and corporate professionals alike, advocating for an active, results-driven approach to innovation and decision-making, while remaining self-aware of the emotional landscapes that all leaders navigate.