“A Guide to the Good Life”: What Entrepreneurs Can Learn From Stoic Philosophy

My Guest

My guest today is Dr. William Irvine, author of the best-selling book A Guide to the Good Life: The Ancient Art of Stoic Joy. He is the author of several other books, including The Stoic Challenge, On Desire, and You: A Natural History (among others).

Dr. Irvine’s work has been featured in countless publications over many years, and was most recently featured in Sam Harris’ app, Waking Up, where he authored and read a multi-episode feature called The Stoic Path, where he articulated the essential elements of stoic philosophy, including its applications for everyday modern living.

Dr. Irvine spent 38 years teaching at Wright State University in Dayton, Ohio, having recently earned Professor Emeritus status there. Dr. Irvine earned his BA in Mathematics and Philosophy from the University of Michigan and an MA and PhD in Philosophy at UCLA.

Listen in Your Browser

"A Guide to the Good Life": What Entrepreneurs Can Learn From Stoic Philosophy In The Trenches

Listen on Other Platforms:

Apple | Google | Spotify | Breaker | Pocket Casts | RadioPublic

Questions Asked


  • Please explain to us what stoicism is, as well as what stoicism is not.

Core Stoic Ideals

  • Core Idea #1: Gratitude for what you have: How compatible are the ideas of stoicism, gratitude, and ambition?
  • Core Idea #2: Live in the present moment, and don’t “suffer in advance”: What do you think Seneca meant when he said that “We suffer more in imagination than we do in reality”?
  • Core Idea #3: We don’t control what happens to us, but we do control how we respond to what happens to us: Are we indeed fully in control of how we think, and how we interpret external events?
  • Core Idea #4: The Value of Difficult Experiences: What can we learn from the Stoics about the power and importance of navigating ourselves through difficult circumstances?
  • Core Idea #5: Time is our most valuable asset: How do you ensure that you’re deliberate about using your time, and not wasting it or allowing others to control it?
  • Core Idea #6: Time is our most finite asset: Some advise others to “live each day as if it were your last”. Is this advise practical and/or realistic?
  • Core Idea #7: Play for the journey, never for the destination: What might the stoics say about the fact that, when entrepreneur’s sell their businesses and achieve a life-changing financial windfall, they’re actually more likely to be depressed than they were while running their businesses?

Your Personal Practice of Stoic Philosophy

  • Some say that humans require a “baseline” level of stress, and when no obvious stressor exists, we seek them out or create them in our own minds. How do you respond to this idea?
  • If you were to write the definitive book on stoic philosophy for 2023, would you add, subtract, or change anything? Why or why not?
  • What has been the most difficult, sad, or disruptive event that you’ve used the various stoic tools to endure?
  • What is negative visualization, and why is it such an important exercise?
  • How should people go about discovering their life’s purpose?
  • How do you maintain your desire to exemplify stoic ideals as much as possible on one hand, while simply allowing yourself to be a flawed human being on the other hand?

Download a Written Transcript of Our Conversation

Access a text-based version of our discussion to highlight, copy or take notes by clicking on the button below

Thanks to our Sponsors

This episode is brought to you by ⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠August Felker⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.

This episode is brought to you by Symphony: On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200.

Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you’re a listener of the podcast to receive this discount!

Leave a Reply

%d bloggers like this: