The $100M Entrepreneur Podcast

Episode: Lost $65M OVERNIGHT: Here’s What Dan Fleyshman Did Next!
Host: Brad Sugars
Guest: Dan Fleyshman
Release Date: January 28, 2026

Episode Overview

This episode features Dan Fleyshman, a serial entrepreneur and investor, as he sits down with Brad Sugars to reflect on his stunning loss of a $65 million company overnight—and the even more remarkable comeback that followed. They dig deep into the lessons of resilience, the mindset required to bounce back, and practical strategies for scaling to $100 million, including sourcing excellence, investor relations, and the architecture of high-growth ventures. Dan’s journey is packed with raw insights into failure, reinvention, and the systems behind building world-class enterprises.

Key Discussion Points & Insights

1. Losing $65 Million Overnight

• The Shock: Dan recounts the moment he lost his online poker site, a $65 million business, due to the 2011 FBI crackdown (“Black Friday”).
  • "It was April 15th at 10:10am. I just lost $65 million company in one phone call." (Dan, 00:47)
  • Impact: All major poker sites were seized, but Dan’s platform was spared punitive action; nonetheless, the business was over.
• Integrity and Responsibility: Instead of folding, Dan manually paid back 41,000 players within four days.
  • "There was hundreds of thousands of players. But 41,000, I had to manually pay back. 2011. Try it now. But 2011, it was like the ice ages for technology." (Dan, 03:20)
• Lesson on Resilience:
  • "Best thing that ever happened...never put my eggs in one basket again. I became an angel investor in 43 companies... everything started when I lost everything." (Dan, 02:37)

2. The Value of Relentless Action & Innovation

• Dealing with Loss: Dan explains the importance of acting rather than wallowing after failure.
  • "I could have sat on the floor and cried about it. But… I just wanted to fix it. Once that week went by, I didn’t have emotion about being sad. I just had to figure out what was going to be next." (Dan, 03:20)
• Catalyst for Diversification:
  • He immediately began investing, hosting events, and starting a charity, emphasizing how disaster can demand transformative action.

3. Getting to the First Million: Start-Up Hustle

• Early Lessons in Entrepreneurship:
  • At 17.5, Dan wrote $1M in orders at the Magic clothing convention without even having a manufacturer lined up.
    • "We wrote over a million dollars. I literally didn’t have a manufacturer...17 year old version of me had nothing set up…I just knew that I had a funny catchphrase. Who's your daddy. That's what I was selling." (Dan, 05:02)
  • Advice to New Entrepreneurs:
    • Balance between "just start" and making sure basic infrastructure (corporation, contracts, payment methods) is ready.
    • "Set up shop before you go out there." (Dan, 06:47)

4. Demand Generation vs. Supply: Sales Cures All

• Dan’s Superpower: Creating demand via marketing before supply.
  • "Most business owners, their genius is supply. They're 80% supply focused... how did you become a genius at demand?" (Brad, 07:03)
  • Tactics: Aggressive brand marketing, high-profile sponsorships, and creative deals (e.g., using ticket incentives at fairs to boost grocery sales).
    • "Marketing caused demand. When I did the Utah State Fair deal, it was Coca Cola for 16 years and they switched to a little energy drink for two years." (Dan, 08:30)
  • Key Quote: "Sales cures all." (Dan, 07:18)

5. Raising Capital: It's About Sales and Belief

• Why Dan Sought Investors Early: Needed working capital to produce and grow (long payment windows with big retailers).
  • "I knew we were gonna be great in my mind. And so I was going to where the puck was, right? The hockey theory, Wayne Gretzky." (Dan, 10:39)
• Raising Capital is Sales:
  • "Raising capital is the same as selling anything. It's just a sale. You're gonna meet with a bunch of people and you're gonna sell them." (Brad, 11:16)
  • The real “first round” is friends, family, and fools.
  • Only raise after proving there’s consumer demand; otherwise, it’s a lost cause.
  • Product Quality Is King: Marketing can get you shelf space, but bad products kill any hope of recurrence.
    • "If someone buys and they taste the drink and doesn't taste good, that's it. No amount of marketing gets past bad product." (Dan, 12:52)

6. Scaling—Who to Hire and When

• Agencies vs. In-House:
  • Use agencies for highly specialized, scalable tasks (media buying, etc.) with proven track records.
    • "Rather an agency that’s got 42 guys like that...they have wisdom of the crowd." (Dan, 13:57)
  • Build your core C-level and mission-critical admin internally, people who “live and breathe” the company.
    • "I want my C-level executives to be my main...if they are not bringing in sales or making an impact for me, I’m not as concerned." (Dan, 16:10)
• Salaries and Retention:
  • "Pay peanuts, get monkeys. 30% more money and you get someone who's twice or three times as good...they don't leave, waste months trying to hire someone new." (Brad & Dan, 16:26)

7. Letting Go to Grow—The People Challenge

• Scaling Issues: Early employees and even co-founders may not make it to $100M.
  • "A lot of times you're hiring your friends and your uncle and your dad...it's really rare they can get you to 10 million...none of them will be there at 100 million." (Dan, 17:35)
• Executive Hiring: Must bring in proven talent from larger organizations to reach the scale of $100M+.
  • "Go steal the CMO of Red Bull...often it’s the number two or three at that place because they're capped." (Dan, 24:37)

8. Strategic Growth through Deepening Relationships

• From $10M to $100M:
  • Better to double down with a few big customers than stretch thin across many.
    • "Going from 10 million to 100 million is typically with the same clients, just going all in with them." (Dan, 19:17)

9. Ecosystem Domination: Getting the Attention of Giants

• Before courting Walmart, Dan built brand presence by sponsoring local schools, sports teams, and key community touchpoints around Walmart headquarters.
  • "I sponsored the high schools within 10 miles because guess who their parents are. They work in Walmart... They thought I was everywhere." (Dan, 21:57)
• Creating Perceived Omnipresence:
  • Using targeted billboards and community presence to project the illusion of a dominant brand.
    • "On the way out, I’m sweers. They called me and the meeting's a lot different when they call you..." (Dan, 22:55)

10. Delegation and Value of Founder’s Time

• Don’t Waste Time: CEOs should ruthlessly delegate all tasks under their highest value.
  • "How dare you sit in meetings for three hours each. That's not a three hour meeting. It's twenty-four hours. You got eight of my staff for three hours each." (Dan, 27:22)
  • “Do you mow your own lawn?” A reminder that founders should offload low-value activities.

11. The True Price of Success

• Relationships vs. Ambition: Accepting that not everyone will come along for the ride; some relationships fade under the relentless pursuit of big goals.
  • "The price of success is a lot of your relationships...But would I do it again? Yes. Because my greater purpose and my ultimate goal is if I go do these things, I will help the world." (Dan, 29:37)

Notable Quotes & Memorable Moments

• "Sales cures all." (Dan, 07:18)
• "Best thing that ever happened in my business life...never put my eggs in one basket again." (Dan, 02:37)
• "Pay peanuts, get monkeys. 30% more money and you get someone who's twice or three times as good." (Brad, 16:26)
• "If you believe you make hundreds of dollars hour for your company, how dare you spend $25 an hour of your time mowing the lawn, cleaning the pool, etc." (Dan, 28:58)
• "What got you here won't get you there." (paraphrased, 17:14)
• "Go kidnap the best executives you can. You want the best... Go get the vice president of Monster." (Dan, 24:37)
• "Do something once, get great at it, but have customers that can take you to that [next level]." (Brad, 20:25)

Important Timestamps

• 00:47 – 03:20 | Dan’s $65M loss story, immediate aftermath, and lessons
• 05:02 – 06:47 | Early entrepreneurship, first million, need for infrastructure
• 07:03 – 08:30 | Demand generation vs. supply: Marketing and sales as drivers
• 09:42 – 12:52 | The realities of raising capital (and when not to)
• 13:57 – 16:10 | When and why to use agencies vs. building in-house teams
• 17:31 – 19:17 | Letting go of early employees to scale to $10M and $100M
• 20:46 – 22:55 | Ecosystem strategy & landing big retailers (Walmart story)
• 24:37 – 26:43 | Hiring top executives for breakthrough growth
• 27:22 – 28:58 | Founder time management; delegation
• 29:37 – 31:14 | The cost of entrepreneurial success and the drive for impact

Conclusion

Brad and Dan’s conversation delivers a masterclass in resilience, expansion, and the inner work behind high-stakes entrepreneurship. Dan’s story of massive loss and greater comeback provides actionable lessons on leveraging adversity, the primacy of sales, strategic team-building, and the true personal cost of success at the highest levels.

Connect with Dan:

• Charity: trinaskids.org
• Social: @DanFleyshman on all platforms

Whether you’re struggling to get your first million or scaling towards nine figures, this episode is packed with road-tested strategies and hard-won wisdom from two of the best in the business.