Nov. 8, 2022

60: Mike Gardon - Investment In Loss

The trading life nearly destroyed Mike Gardon. Since stepping away, he’s obsessed with creating “life options.” At the core is the idea of “investment in loss”: to make significant changes, we often need to step backward. Today, his mission is to “break our mental constructs for what it means to make a living.” Enjoy!

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02:17 Ironman mentality

06:37 Compounding personal gains

09:48 Stratify your goals

12:31 Mike’s childhood → career start

17:56 Rebelling against the default path

20:06 Investment in loss

23:31 Portfolio mindset

25:34 Passion for career coaching

27:50 Mike helping his former self

33:47 Involving your family in major change

34:52 Risk mindset for personal growth

37:00 “Is what you’re pursuing big enough?”

40:02 Life options

41:50 Skin in the game

47:03 Money, time, & energy

52:30 Uncaged = ownership



1. Pushing yourself with a new venture is not just about the accomplishment. It’s the person you become in the process.


2. “What’s your Ironman race?” Find the near-term thing in your life that forces your growth.


3. The entrepreneurial journey starts with a flicker inside you (an inclination) before you take tangible action.


4. The ultimate safety isn’t choosing the “right” path; it’s creating life options.


5. Portfolio mindset: make multiple concurrent bets and see what sticks. Even with the “failures,” you’ll grow tremendously.


6. Slow down (even step back) to speed up.


7. In managing the risk of major life decisions, too many remain stuck protecting what they have instead of pursuing what’s possible.


8. “Don’t tell me what you think, [show me] your portfolio.” —Nassim Nicholas Taleb


9. “Every decision is an investment decision.” You must devote appropriate money, time, and energy to the transformation you seek.


10. Choose yourself.



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