In this episode of The Eric Ries Show, I'm joined by Jess Mah, an extraordinary entrepreneur who launched her first six-figure business in middle school and went on to co-found more than 10 companies collectively valued at over $1 billion.
Jess rose to public acclaim and earned a spot on Forbes' 30 Under 30 while privately facing the reality that her startup, inDinero, was far from profitable. That moment of failure became her turning point. Without VC funding, Jess had to rethink everything: her approach to building companies, her work methods, and her true priorities. What emerged was a more sustainable approach to entrepreneurship that prioritizes long-term thinking, authenticity, and mental health.
In our conversation, we explore:
• The hidden upside of failure and how it transformed Jess's career
• Why inDinero's failure to attract VC money was ultimately a blessing in disguise
• How AI is lowering barriers to starting a business with less capital and fewer workers
• Why authenticity beats performative positivity
• How Jess manages her mental health and her iterative learning approach inspired by 'kodawari'
• The “independent director problem” and how investor-beholden directors can undermine long-term strategy
• Why funding private companies is a frequently overlooked way to create global impact
• Jess’s 90-day trial method for evaluating executive talent
• Jess’s work supporting other female founders
• And much more!
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Where to find Jess Mah:
• LinkedIn: https://www.linkedin.com/in/jessicamah/
• X: https://x.com/jessicamah
• Website: https://jessicamah.com/
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Where to find Eric:
• Newsletter:https://ericries.carrd.co/
• Podcast:https://ericriesshow.com/
• YouTube:https://www.youtube.com/@theericriesshow
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In This Episode We Cover:
(00:00) Intro
(02:30) Why happiness eludes so many high achievers
(10:15) Why Jess considers herself lucky that inDinero was not a rapid growth company
(14:20) How Jess discovered that habits like meditation and exercise drive success
(17:10) Silicon Valley Bank: why short-term thinking and exploitation are bad business strategies
(24:00) Why it’s so hard to break out of the default culture of rapid growth
(28:30) Why Jess walked away from the Silicon Valley playbook
(33:11) Where Jess’s strength comes from
(40:25) Why true accountability doesn’t require a combative board
(44:43) What good governance looks like—and why it’s different for every company
(50:10) Jess’s long-term approach to goal planning, both in life and work
(51:34) Jess’s barbell approach: balancing cool businesses with world-changing tech
(58:15) Jess’s approach to hiring and spotting well-matched talent
(1:04:20) Strategies Jess uses to manage her emotions and learn from failure
(1:10:54) Lightning round
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You can find the transcript and references at https://www.ericriesshow.com/
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Production and marketing byhttps://penname.co/.
Eric may be an investor in the companies discussed.
