Lessons from Failing His Way to Building 10+ Businesses, The Sweet Spot For Finding Co-Founders, And The Software Flops That Positioned Him for the AI Revolution, With Deepak Shukla
Tue Jan 27 2026
Today, I’m speaking with Deepak Shukla, serial entrepreneur and CEO at Pearl Lemon Group, a diverse portfolio of 10+ companies, some of them very brick and mortar, like pet transport and event catering.
We talked about:
* why going into business with old friends often doesn’t work
* what the sweet spot for finding business partners and co-founders actually is, and how to align expectations upfront to prevent painful breakdowns later
* how a string of software company failures actually turned out to be good luck
* how persistence, even with two years of zero traction, led to breakthrough success
Enjoy my conversation with Deepak!
Learn more about your FounderEQ and get your score for free in 5 minutes here.
If you enjoyed this week's episode, please consider:
* Subscribing to the podcast on Apple Podcasts, Spotify, or wherever you listen.
* Giving a rating and reviewing the podcast on Apple Podcasts. (Even a short two-sentence review helps!)
Want support in leveling up your leadership? Send an email to hello@renitakalhorn.com to learn how we can work together.
Get full access to The High-EQ Founder by Renita Kalhorn at renitakalhorn.substack.com/subscribe
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Today, I’m speaking with Deepak Shukla, serial entrepreneur and CEO at Pearl Lemon Group, a diverse portfolio of 10+ companies, some of them very brick and mortar, like pet transport and event catering. We talked about: * why going into business with old friends often doesn’t work * what the sweet spot for finding business partners and co-founders actually is, and how to align expectations upfront to prevent painful breakdowns later * how a string of software company failures actually turned out to be good luck * how persistence, even with two years of zero traction, led to breakthrough success Enjoy my conversation with Deepak! Learn more about your FounderEQ and get your score for free in 5 minutes here. If you enjoyed this week's episode, please consider: * Subscribing to the podcast on Apple Podcasts, Spotify, or wherever you listen. * Giving a rating and reviewing the podcast on Apple Podcasts. (Even a short two-sentence review helps!) Want support in leveling up your leadership? Send an email to hello@renitakalhorn.com to learn how we can work together. Get full access to The High-EQ Founder by Renita Kalhorn at renitakalhorn.substack.com/subscribe