The Jen Gottlieb Show Thriving Through Failure: How Losing $65 Million Became Dan Fleyshman's Greatest Gift
When Dan Fleyshman says "losing 65 million dollars was literally the best thing that ever happened to me," he speaks from hard-earned wisdom. As the youngest founder to take a company public at 23, Dan rode high on his early successes—until a government regulation in 2011 wiped out his business overnight.
In that moment of crushing loss, Dan had to make a choice: stay busy building or sit and wallow. Diving headfirst into new ventures, from consulting to angel investing, he discovered a life-changing truth - imperfect action will always triumph over paralysis.
Since then, Dan has launched over 40 companies, invested in dozens more, and become one of the most connected people in business. The secret? Treating relationships like his most precious asset. From saving contact info to planning meetups on the go, Dan breaks down his unique system for building a world-class network.
He also gets candid about dealing with loss, why ego is the silent killer of success, and how becoming a dad has radically shifted his priorities. Plus, Dan reveals his ambitious mission to solve homelessness and hunger - and why he believes entrepreneurs, not governments, hold the key.
"When the room is quiet and you're not working on anything, all you do is reflect on the bad stuff...But if you're busy working, none of that's in your mind because you're busy." ~ Dan Fleyshman
In This Episode:
- Dan’s impressive achievements
- Losing $65 million overnight! And the secret to bouncing back
- How ego destroys personal brands and influencers
- The untapped power of personal branding for lasting success
- Building and keeping relationships that matter
- The right (and wrong) way to pitch your big ideas
- Is there a common thread in businesses that fail?
- What’s next for AI, and how will it impact the future?
- How becoming a parent shifted Dan’s perspective on life
- Why in-person events are evolving and what it means for you
- Dan's life on a ranch
- The question on imposter syndrome: personal branding with flaws and all
- Understanding human nature in business
- “Baby Girl Boss” - bringing more women into business
- Dan’s world-changing mission: what’s next?
About Dan Fleyshman:
Dan Fleyshman, the youngest founder of a publicly traded company, began his entrepreneurial journey at 19 by licensing his apparel for $9.5 million and expanding energy drink distribution to 55,000 stores. His diverse career includes launching a top online poker site, founding "Elevator Studio," which has invested heavily in social media influencing, and co-creating the "100 Million Mastermind Experience."
Fleyshman has also made his mark as an angel investor, keynote speaker, and podcast host of "The Money Mondays." His business ventures extend to the sports card industry with "Cards and Coffee," while his philanthropic efforts include breaking the Guinness World Record for the largest toy drive, operating a 26-acre animal sanctuary called "WYLD Jungle," and running a charity that provides emergency supply backpacks for the homeless.
IG: https://www.instagram.com/danfleyshman/
YouTube: https://www.youtube.com/@themoneymondays
Twitter: https://twitter.com/DanFleyshman
Where to find me:
IG: https://www.instagram.com/jen_gottlieb/
TikTok: https://www.tiktok.com/@jen_gottlieb
Facebook: https://www.facebook.com/Jenleahgottlieb
Website: https://jengottlieb.com/
My business: https://www.superconnectormedia.com/