I Lost $65 Million In One Day… And It Changed Everything- Dan Fleyshman

23 Jan 2026 · 1 h 23 min · 38 chapters

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In short

Earn Your Leisure Podcast Episode Summary: "I Lost $65 Million In One Day… And It Changed Everything - Dan Fleyshman"

Episode Overview In this episode of the Earn Your Leisure Podcast, hosts Rashad Bilal and Troy Millings interview Dan Fleyshman, a serial entrepreneur and angel investor. Fleyshman shares his unique journey, including his record as the youngest person to take a company public at 23, the challenges he faced, and the lessons learned from losing $65 million in a single day. The discussion covers various topics including entrepreneurial success, branding, social media, investment strategies, and philanthropy.

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Key Points

Dan Fleyshman's Background

  • Early Ventures
  • Fleyshman began his entrepreneurial journey by taking a clothing line to a major trade show at the age of 17, which led to significant sales.
  • He trademarked the phrase "Who's Your Daddy," which gained immense popularity.
  • Taking a Company Public
  • At 23, he took his energy drink company public, making history as the youngest to do so.
  • Discussed the dual nature of being a public company:
  • Pros: Access to capital, leverage through stock deals.
  • Cons: Extensive legal and financial documentation burdens (hours spent on 10Qs and 8Ks).

The $65 Million Loss

  • Fleyshman recounts the day his online poker site was shut down by the federal government, resulting in a loss of $65 million.
  • This pivotal moment forced him to reassess his business strategies, leading to diversified investments and the creation of new revenue streams.

Investment Philosophy

  • 40/40/20 Strategy:
  • 40% in low-risk investments (e.g., bonds, stable companies).
  • 40% in medium-risk (e.g., real estate, cash-flowing businesses).
  • 20% in high-risk (e.g., cryptocurrency, startups).

Entrepreneurial Lessons

  • Importance of capital management: The number one reason businesses fail is running out of money.
  • Advice to entrepreneurs:
  • Don’t put all your eggs in one basket.
  • Diversify investments without losing focus on the core business.
  • Seek capital when revenue is flowing, not when in crisis.

Social Media and Branding

  • Creative Marketing: Fleyshman's innovative marketing strategies helped his brands compete against much larger companies.
  • Personal Branding: Emphasized the importance of building a personal brand and leveraging it to create opportunities.
  • Influencer Model: Discussed how to monetize social media followings through direct outreach to brands rather than waiting for companies to approach influencers.

Philanthropy

  • Fleyshman runs a large toy drive and encourages community involvement and self-funding for charitable activities.
  • Emphasizes the impact of teaching financial literacy and entrepreneurship as a form of charity.

Final Advice

  • Get Started: Emphasized the accessibility of resources available via smartphones and the internet.
  • Engage Your Audience: Create content that informs, educates, and entertains rather than focusing solely on oneself.

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Conclusion This episode of Earn Your Leisure offers listeners deep insights into the entrepreneurial journey of Dan Fleyshman, highlighting the risks and rewards of business, the importance of adaptability, and the power of community and personal branding. Fleyshman’s experience serves as a masterclass in overcoming adversity and building sustainable wealth.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Introducing Dan Fleyshman

1:46 to 3:46

Hosts introduce Dan Fleyshman, highlighting his entrepreneurial accomplishments.

“Jesse Mills, host of the Mailroom Podcast.”

Early Entrepreneurial Journey

3:46 to 4:50

Dan shares his experience of starting a clothing brand and his early successes.

“Got our guy Dan Fleischman in the building.”

The Path to Going Public

4:50 to 7:58

Dan discusses the process of taking his company public at a young age.

“Life is short, so I'm trying to do as much as I can while I'm still here.”

The Challenges of Public Companies

7:58 to 11:40

Dan explains the difficulties and experiences of being a CEO of a public company.

“and I just took that magazine and said, we're the best tasting drink.”

The Aftermath of Going Public

11:40 to 14:00

Dan recounts the events leading to his resignation from the company on its 10th anniversary.

“He was this icon that knew all the guys in the public markets.”

The Challenges of Early Business

14:00 to 15:00

Learn about the slow and frustrating processes in early business operations.

“And every single one of them, if there's one change, you're talking about a month or two of just waiting around.”

The Rise and Fall of a Company

15:00 to 16:32

Explore the journey of a company from success to eventual decline.

“I was the Hoosier Daddy guy for a decade.”

Navigating Youth and Credibility

16:32 to 18:06

Discover how youth can be perceived as both an asset and a liability in business.

“And so I would use it for the novelty that it was with some things.”

The Poker Venture

18:06 to 20:14

Hear about the launch of an online poker site and its unique marketing strategies.

“Because I couldn't afford to go against Full Tilt Poker and PokerStars.”

The $65 Million Loss

20:14 to 22:11

Understand the shock of losing a significant investment and its implications.

“He was already living that life off the grid.”
Show all 38 chapters

Lessons from Loss

22:11 to 23:32

Learn how a massive loss can lead to new entrepreneurial opportunities.

“And I found out what they were doing was miscoding merchant transactions.”

Creative Marketing Strategies

23:32 to 26:50

Explore innovative marketing tactics used to compete against larger brands.

“They bought 3.2 million of drinks per year for three years as a base minimum.”

Diversification in Business Strategy

26:50 to 28:00

Discuss the importance of diversification and strategic business planning.

“So you said your philosophy on business changed and you'll never put all your eggs in one basket.”

The Importance of Diversification in Business

28:00 to 28:45

Learn why it's essential to diversify investments without losing focus on core businesses.

“And so when I talk about diversification, I don't mean necessarily I'm going to go do the other thing.”

The Evolution of Sports Betting

28:45 to 30:08

Discover how the landscape of sports betting has changed dramatically over the years.

“executives or partners or staff to help you run that thing because you're not going to be able to scale it fully yourself.”

The Math Behind Gambling Odds

30:08 to 33:55

Understand the mathematical principles that make winning at gambling nearly impossible.

“That's how bad sports betting has been in my mind because that's what it was.”

Personal Stories of Loss and Consequences

33:55 to 35:06

Hear personal anecdotes about the negative impacts of gambling and substance abuse in sports.

“is there an emotional reaction from you?”

Funding Challenges for Entrepreneurs

35:06 to 37:15

Explore how access to capital is a crucial factor in the survival of new businesses.

“Last night in the Jake Paul, Anthony Joshua fight, you could bet on, are they going to mention Logan Paul, the commentators?”

The Impact of Early Financial Support

44:51 to 46:34

Dan shares a personal story about the financial support from his mother.

“My mom was making$2 ,200 a month for a family of four.”

The Importance of Sales in Business

46:34 to 47:11

Dan discusses how focusing on sales is crucial for business success.

“And a lot of them are in Marcus's group and Hymn 500's group because I've met some of them.”

Transition to Social Media Discussion

47:11 to 47:21

Dan shifts the conversation towards his involvement in social media.

Early Social Media Strategies and Experiences

47:21 to 49:57

Dan recounts his initial experiences with social media and influencer marketing.

“And let's start there, because I have a multi-level conversation with social media.”

Diversifying Product Lines

49:57 to 50:26

Discussion about the importance of diversifying products in business.

“Are you multitasking, diversifying the products?”

Hiring a CEO and Business Growth

50:26 to 53:10

Dan explains the significance of hiring a CEO for scaling his agency.

“or I'm spending money for Pretty Little Thing and Boohoo and Nasty Gal, all these brands, if they gave me money, Siroc Vodka, if I got money from Siroc Vodka, I learned what would work.”

Building a Personal Brand and Networking

53:10 to 54:31

The importance of personal branding and networking for success.

“That was eight years or nine years of running around with the social media agency.”

Investing Strategies and Event Facilitation

54:31 to 56:00

Dan discusses how he finds investment opportunities through networking events.

“The powerful thing in that has kind of been the theme throughout your story thus far is that these relationships that you have are fostering new opportunities to you.”

Identifying Investment Opportunities

56:00 to 57:50

Learn how Dan Fleyshman identifies and invests in profitable companies.

“There was a one called Dollar Beard Club, monthly box for beards.”

The Power of Transitioning Roles

57:50 to 1:01:00

Discover the importance of transitioning from operations to brand ambassador roles.

“what what was the biggest difference for that jump in that year one i was running the entire business myself.”

Financial Discipline and Risk Management

1:01:00 to 1:02:50

Dan shares his financial strategies and risk tolerance in investments.

“So I've disciplined in the sense that I'm obsessed with investing.”

Proactive Strategies for Influencers

1:02:50 to 1:07:30

Learn actionable strategies for influencers to monetize their platforms effectively.

“It's not just going to show up in their bank account.”

Common Pitfalls in Social Media Engagement

1:07:30 to 1:10:00

Understand the mistakes influencers make and how to create engaging content.

“You talked about, I mean, that's interesting, right?”

Creating Engaging Content

1:10:10 to 1:11:25

Learn how to create content that captures audience attention effectively.

“If you don't want to see someone's salad, don't post your salad.”

Monetization Strategies for Influencers

1:11:25 to 1:15:06

Explore strategies to monetize your online presence and community effectively.

“I really want to buy from EYL University.”

Building a Brand and Community

1:15:06 to 1:17:54

Understand the importance of storytelling and community engagement in brand building.

“Wednesday, you're posting fitness and with your kids.”

Event Management and Its Impact

1:17:54 to 1:22:04

Gain insights into organizing impactful events and their role in community growth.

“how to invest, how to trade, you're showing them other characters through your podcast.”

Philanthropy and Giving Back

1:22:04 to 1:24:00

Discover the significance of philanthropy and personal motivations behind charitable actions.

“But I'm at your stadium and you're selling the shirts.”

Toy Drive Initiatives and Community Impact

1:24:00 to 1:25:42

Learn about the extensive toy drive efforts and their positive effects on families.

“And so we got Allen Iverson in Virginia.”

The Power of Getting Started and Creating Content

1:25:42 to 1:27:00

Discover the importance of starting projects and leveraging social media for success.

“Definitely any last words or your social and any thing that you want to leave the audience with?”
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Transcript

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0:00This is an iHeart Podcast. Guaranteed Human.

0:31a.k.a. Neuro Linguistic Programming. Is it a self-help miracle? A shady hypnosis scam? Or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year we're talking honestly about mental health, relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

1:14Hey, it's Joel. And Matt. From HowToMoney. If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is Dr. Jesse Mills, host of the Mailroom Podcast.

1:49Each January, men promise to get stronger, work harder, and fix what's broken. But what if the real work isn't physical at all? I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the valley of despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to The Mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows. This episode is brought to you by PNC Bank.

2:21A lot of people think podcasts about work are boring, and sure, they definitely can be. But understanding a professional's routine shows us how they achieve their success little by little, day after day. It's like banking with PNC Bank. It might seem boring to save, plan, and make calculated decisions with your bank, but keeping your money boring is what helps you live a more happily fulfilled life. PNC Bank, brilliantly boring since 1865. Brilliantly Boring Since 1865 is a service mark of the PNC Financial Service Group, Inc. PNC Bank, National Association, member FDIC. When I did the podcast with you all, I was telling you, probably the most impactful interview I've done in my career.

3:09Heroes now. Real heroes. I heard Rashada Troy talk about the tax letter. We talk about finance, but we talk in a language that is common to the people that's from the community that we grew up in. You all are the bright spot of real estate and entrepreneurship for black Americans. This is the knowledge that actually matters. I applaud both of you for this. Thank you. Policy isn't a country issue. It's not an American issue. It's a world issue. He came to earn our leisure.

3:45All right, guys, welcome back. Yeah. Special episode. Got our guy Dan Fleischman in the building. Long overdue. Joining us. So happy to be here. Yeah. It's a pleasure. If you're not familiar, serial entrepreneur, angel investor, author, philanthropist. You were the youngest founder to take a company public on the stock market. Yeah. That's correct. 20 years ago. Okay. At 23 years old. Yep. Okay. Made history, invested in over 40 companies, and really big, I guess, people in the online world might know you for what you've been doing on the branding and social media and kind of really trailblazing that space as far as online marketing and funnels and different things of that nature.

4:29So we got a lot to talk about here as far as the world of entrepreneurship, your journey, what's happening now with social media, online marketing. But first and foremost, thank you for joining us. Appreciate it. It's a pleasure. Did we leave anything out? I feel like the love for animals, the events, father. A lot of moving parts. A lot of things going on, man. Happy to have you here. Thank you. Thank you. It's fun. Life is short, so I'm trying to do as much as I can while I'm still here. Why not? So, OK, so where does this journey start? Like I said, you took a company public 20 years ago, you said, 23 years old, and was the youngest.

5:04Is that still a record? Yep. The youngest ever to take a company public? Yep. Michael Dell was 24, so he beat me by$8 billion, but I got him by like eight months. So talk about that. Talk about where you started and specifically that journey of taking a company public so young. So high school, I was working three jobs to save up money because we didn't have any money. Where are you from? I was born in Riga, Latvia. Moved when I was six months old. and I grew up in Long Beach. And my brother was going to Pauly High. I was just saving money to go to college. And instead, I ended up using that$43 ,000 I saved during those three years.

5:39So it was like$12 ,000,$15 ,000 a year. Saved that money, and I put in to go to Magic, the clothing convention. Vegas. And I thought it was going to be big time. I got 20 feet instead of 10 feet. And on my left is this brand called FUBU. And on my right is a brand called Sean John. That was their debut in 1999. so million dollar booth million dollar booth i spent my 43 000 thinking i'm gonna be a rock star but i got lucky because hello cool jay and damon everyone's walking by there's a line waiting to go into his booth sean john's got a line waiting to go in their booth the line was in front of my booth and so i did over a million dollars in orders oh wow 17 years old and close and close and i just owned the catchphrase who's your daddy like the slogan who's your daddy oh that was you You came up with that?

6:23This is after Pedro or before Pedro? No, I sued them. So you started with your daddy. Yeah. So the catchphrase was out there. I trademarked it. Okay. So 1999, 16 classes of trademarks, 300 products all over the world. At what age? This is when I was 17 and a half. Wow. And then I became 18. I became big boy. And that's when I really got, luckily magic was when I was 18. And so that's where the journey started. at 19 we did a deal with starter apparel for 9.5 million a licensing deal they gave us uh that deal for three years so that helped fund the ups and downs of an entrepreneur i would we keep making some money losing it getting screwed over on our samples we opened up an office here empire state building with we had the fubu ladies brand in there we had kevin garnett's brand in their official block family we had rough riders in there so we were doing the rough riders clothing brand This is the year 2000 And it was just like all six brands were all in one Office here in New York And then I wanted to do an energy drink Because there was 900 drinks But they all tasted like cough syrup That thick taste Because of one ingredient called taurine Makes that thick taste So we turned down the taurine Turned up sucralose and some other ingredients to make it taste good We won flavor of the year Out of 900 drinks on the cover of DevNet magazine And I just carried that magazine everywhere I went Is that the Who's Your Daddy energy?

7:47And so that's the company I took public. So we had the clothing as licensing, and Energy Drink was the main core product. Went public on April 1st, 2005, and for four years I didn't sleep. I just sold 43 distributors, 55 ,000 retail stores, and I just took that magazine and said, we're the best tasting drink. And I carried the drink everywhere. And that's where it all started from. Okay. 18 years old. Multi-millionaire. Where are you getting the – I mean, when you're even talking about trademarking and suing, like at that age, I mean, that's not even in my lexicon at that point. Like, how are you managing that?

8:25And how did you even become familiar with that type of jargon at such a young age? I wasn't familiar with it at all. I just, you know, there was no cell phones. I didn't have a pager. You know, I think a cell phone started coming out around that time. But there's definitely no smartphones yet. And so I was just surrounding myself with people that were like, some were taking advantage of me and some were really helpful. so like one guy made us sweaters he made 36 000 of sweaters for 12 of them so he stole most of our money the guy we met because of him ended up doing the 9.5 million dollar deal so the bad guy got me to the good guy right does that make sense and so the mentors around me some screwed me over some helped me a lot and the journey happened because of certain guys there was one named christopher wicks he owned fender guitars english laundry hang 10 ocean pacific and body glove and la gear He owned licenses to all these brands back then.

9:17And he was the one that helped us with the manufacturing and dealing with all the retailers. And then we met a guy named Elliot Levine who was running FUBU Ladies. And he was the CEO of Jordash. And he was running all these big brands back then. And he was also the CEO of Donna Karan for like a few years. That guy helped us a lot to get into a lot of these retailers. He ended up getting into a lot of trouble with Steve Madden, that whole Wolf of Wall Street situation. so there's a lot of interesting dynamics that happened during that time which would take hours to get into but those guys the good guys and the bad guys are what helped me learn the jargon learn and understand what was going on as far as so okay you take the company public right um what was the journey after it went public like how did that actually impact the business you as a ceo what was the journey of of being a ceo of a publicly traded company so it takes about two years and two million dollars to go public the accounting and legal fees back then now there's things that are faster and slower based on regulations but this is 2003 to 2005 it took us two years two million the day we went public we got in 3.75 million so it helped us a lot with cash flow and we had now access to do deals because we have a public company our market cap was small at the beginning like 30 40 million we got to like 65 million 70 million and we were able to do trades and deals with our stock.

10:39And so I do sponsorship deals with NASCAR. I could never afford it with cash. I would give them stock. I would do a deal with the Utah State Fair. Well, Coca-Cola, it was called the Coca-Cola State Fair. I went there with stock. So I did a lot of deals with my stock, which helped us a lot to do trades and deals. But the worst part was I was hours and hours and hours and hours and hours a week dealing with the 10Qs and the 8K filings. And those were torturous. Like I still have PTSD. How many hours you have to go through it? If you're wrong, you go to jail. And I don't really know it. I'm depending on my CFO to know what's right.

11:16I'm depending on accountants to tell me what's right. But I'm the CEO of the company, of a public company. I'm the one that would get in trouble ultimately. And so the hard parts of being publicly traded is the paperwork part because it is a nightmare, especially back then. The good parts is you can use it for assets. You can use it for strength. You can use it for leverage and credibility. and being one of the only publicly traded company at the time for beverages it helped us a lot i don't regret going public but it's also i still have fear of going public now just because of the memories of how many hours go into the legal and accounting process but i will say the power of being public is it's monumental you can do so many deals with your stock i wonder like twofold question at the time this is your 18 19 obviously 23 the youngest still to do it was going public a goal and the second part of it was obviously you said ptsd so what are the ugly parts that people don't talk about yeah that are giving you that angst so it wasn't the goal we were actually going to go public when i was 21 there was a gentleman named james morris he was like the legend of penny stocks back then and legend of that that world living on yachts with 19 year old girl is in his 70s.

12:29He was this icon that knew all the guys in the public markets. He was going to take us public and on the day that it happened, I never told this story before, we're in Malibu at the old Red Bull office and he was in that office in this meeting with us and we're literally about to sign, we've been working on this paperwork for seven months with these guys that are taking us public. He's got the paperwork out and as we're about to sign, I still have it in my head, that's part of the PTSD, he falls over and has a heart attack. We are laughing because it feels like an actual joke. Like he full-fledged has a heart attack.

13:07We've been seven months in preparation. He's a funny guy. So we are actually laughing as he's on the floor having a heart attack, thinking that it's a joke. We realize it's not a joke. We get him over to Cedars-Sinai Hospital and he passed away that night. Those guys obviously don't want to move forward. Like they're out. And so I didn't think I was going to go public. I didn't even know what going public really meant. And then other investment bankers that were friends with him, because he was my mentor in this whole scenario, they came to us and made us an offer to go public. And so going public was never the goal.

13:41The only PTSD real true part of being public is the paperwork. It is torturous because you do your accounting to give to an auditor. The auditor gets audited by an auditor. The SEC audits the auditor. The auditor audits your auditor who audits your auditor. I'm not exaggerating. And every single one of them, if there's one change, you're talking about a month or two of just waiting around. Especially, remember, this is back then, 20 years ago. It's not like the internet was the same. It wasn't like you just group chat. There was no group chat. There was no smartphones. And so things were much different there and slow and frustrating.

14:18And so there was no software programs and platforms that you can use now to do things quickly. and so i never planned to go public um i've now i sit on some public boards but i don't i don't plan to go public again just because i still think about all those moments um okay so and then the company did the company stay on the stock exchange did it get yeah delisted at some point like how did the story end with the company so on the 10 year anniversary 522 2009 is when i resigned i started 522 1999 i only know because that's we put on our hats and our shirts to the date. On the 10th anniversary, I resigned.

14:58I wanted to put another feather in my cap. And I'd done the same thing. I was the Hoosier Daddy guy for a decade. And when I left, it went from 55 ,000 stores to 18 ,000 stores to 4 ,500 stores to gone. Because I was the driving force. I was the crazy guy flying around to every single Costco, Ralph's, Albertson, 7-Eleven. I went to every headquarters. I knew Johnny and Jennifer by name. Like, I knew everyone. I was there in the streets to all 43 distributors, all of them. I was training the reps. We had Budweiser, Coors, Miller, and Pepsi distributing for us. I was there with them. And so once I left, there was still a sales team.

15:36It's just much different, especially, again, back then. You sold your shares when you left? Yeah. What was the price of the shares when you sold it? A dollar, a dollar oh six, a dollar oh six. Yeah. I'm thinking now, like, there's a couple of things running through my mind. This is really interesting. So in this world, right, we see young people having success and they're kind of figuring out. But your success is different at a young age. Like, I wonder in the world that you were living in at that time, did age work to your benefit or was it a detriment? Right. Like, because in the business, especially going public and taking a public company, you have to have a certain level of credibility.

16:14Your mentor has just passed. How did you navigate that at a young age? Did it work against you? so in some rooms it was like a novelty right like the retailers liked it the people i'd work with liked it some investors loved it others would never touch me right because i'm wouldn't come to me because they didn't trust in a 23 year old 25 year old 26 year old running a public company and so i would always reference the fact that i had 40 50 60 70 year olds helping run the company i hired cfos i hired a president i hired a national sales manager i hired executives so I would reference them to the people that I couldn't get past the fact that I was young.

16:54And so I would use it for the novelty that it was with some things. And the ones that gave me pushback or went and talked to me, it didn't matter because there's so many other deals to do. There's so many other retailers to go to. There's so many other investors to go to. I just brushed it off. I literally don't remember someone saying no. Out of the 43 distributors, 55 ,000 stores, you can put me on a lie detector test 30 times a month. I don't remember someone saying no. whether that's delusion or passion i don't know but i went to every distributor and said we're the best tasting magazine we're already in costco 7-eleven how many would you like to order i didn't say would you like to order how much like how many do you want to order you have to have us it was what is in my mind and so the youngest thing the youngest guy thing that was my that was my shtick that's what i used to go out there confidence yes so once you once you More delusion.

17:44Both. Once that ended, what did you do next after that? So I liked poker a lot. I was playing a lot of poker. And so I started an online poker site. I was looking for voids in the market, whether when I created hoverboards or energy drinks or poker sites, I would find something that wasn't working. So in poker, there was 550 sites, but Bodog was the only cool brand, and they had just left to focus on sports. So I said, okay, i'm never going to be the biggest energy drink or the biggest poker site But I can get a niche I can carve out a niche And so I went and signed this is 2009 The cool guys in poker and then I brought in other characters that were not necessarily Considered poker players, but like poker Dan balzerian steve aoki a bunch of playboy playmates So I took balzerian steve aoki and playboy playmates put them into a poker site Got professional poker players that were young like young hot shots and placed them all on television.

18:41Because I couldn't afford to go against Full Tilt Poker and PokerStars. They were doing$4 million a day and$8 million a day in revenue. I started the whole company with$2.4 million. I didn't raise money. I just put in$2.4 million. Started this company, again, out of delusion, to fight with two companies that do$4 million, $8 million a day. The way I was going to combat it was, I have all the cool kids. I'm going to take this DJ, an interesting character in Bilzerian, make them more famous, and add in the hot models and Playboy Playmates and make this a global brand. Within 10 weeks, we were live.

19:14I moved to a place called Malta, never even heard of Malta, put on a backpack and moved to Malta, literally just booked a hotel room for a week, ended up staying for two and a half years and got my gaming license. Within 10 months, we're the fifth biggest site in the world. I'm doing six figures a week net in revenue with five employees making five grand a month each. Nothing else. I had no office, no other staff. and that's how it online gambling yes this is you know what you're saying this now and for years i'm trying to figure out where did we know dan from like he just kind of appeared he was the cool guy he had a lot of women around and we just could not figure it out we were living at panorama towers in vegas he went and rented the biggest penthouse there i lived in the townhouse by the pool and every friday night he would literally have 40 girls that was a real thing he had dan Damn Brazil.

20:04Yeah, yeah, yeah. So you, you, you found, we didn't find him, but you, you kind of made him. Yeah, I didn't invent him, but I installed social media on his phone and he made it his own. It went crazy. Yeah, but that was. You made him a social media thing. Yes. He was already living that life off the grid. Correct. And you, you made it the social media thing. Yes. And he made it, and he made it humongous, obviously. We did the first thing called a tag a friend. Yeah. Or tag three friends. we put 30 xboxes on a table and said whoever tags the most friends wins the 30 xboxes and that got like hundreds of thousands of comments we then did a charity thing where he said i'm going to give 10 families ten thousand dollars each secretly he actually ended up giving dozens of families extra ten thousand dollars each tag your friends it was like 116 ,000 comments we were going through all these applications and so his page he grew virally from those initial things and then making that content was unreal what i did was i was placing him on youtube videos and twitter we didn't have instagram back then it was just getting started and uh that content helped us go viral because we were getting youtube videos with him and hot girls but then also we had poker videos of them playing these big poker hands i was playing on tv poker they were playing on tv poker we had a playboy playmate go win a fox television show like there's all this different action but it was like 10 seconds later basically like i think it was a year and a half was april 15th 2011 i lost the 65 million dollars in one morning online poker got shut down by the federal government in america on april 15th i was living in malta but i was at the bellagio i get a phone call from bilzerian at 10 10 in the morning i'll never forget where are you not the bellagio where are you and he's asking me why aren't you in malta poker got just shut down just got shut down by the fbi if you go look at full tilt poker poker stars absolute poker go look at their websites the cover of the website says property of the federal bureau of investigation i go to my website luckily it was just my website nothing had happened.

22:11And I found out what they were doing was miscoding merchant transactions. So let's say you deposit$1 ,000 on PokerStars. It would say PS3. You deposited three grand on PokerStars. It would say mattresses.biz on your credit card statement. Mine, I had one bank account at Wells Fargo, KPMG accounting, and one merchant account. So I never got in trouble. But April 19th, four days later, I was supposed to get in a$3.5 million deposit at a$65 million valuation for the company. I just rented out the Gaia Resort in Costa Rica. I was flying in models and playmates and poker pros. We're all flying to Costa Rica April 19th to do this huge photo shoot campaign.

22:53April 15th, I lose$65 million. That moment changed the rest of my life. I manually paid back 41 ,000 players. we had hundreds of thousand players withdraw 41 ,000 that didn't withdraw so we had to manually pay them back and that loss that 65 million dollar loss was the best thing that ever happened for my career why yeah everything started from then I'm never gonna have all my eggs in one basket again I started my live events I started my charity I started angel investing I started my social media agency everything that i started then i still have to this day all stemmed from losing it all i don't know if i would have become the poker guy or been whatever still doing poker many many years later i have no idea but that moment changed how i invest how i think because i ran one company for 10 years and i thought i was going to run this company for 10 years but after a year and a half i lose everything overnight that's that's a lot but there's still lessons that are there right because even with with the dance situation in ioko in the world of marketing right it is there's a line of making things look good and having things that convert and i feel like you kind of mastered that and blended it but it's carried on through your career talk about that process right because people are attracted to the things that they see right but we got to figure out how we can get those people to become customers at a certain point how did you how did you become a master of that each category i'm fighting with 800 pound gorillas i can't outspend these guys there's no chance you can't outspend in the clothing industry energy drink business poker business how are you going to outspend these brands i can't and so each time i try to figure out creative marketing tricks the nascar example it was 3.2 million to do the nascar i was using stock but i also did a deal with circle k Circle K, if you look at my NASCAR, if you look at the pictures, you'll see my energy drink name on it.

24:56And the side said Circle K. Why? They bought 3.2 million of drinks per year for three years as a base minimum. That means I was making around half, so 1.6 million. That's what I used as cash in stock to NASCAR. How am I going to go fight with Red Bull, Monster, and Rockstar who have 5, 10, 20 NASCARs that they just write a check for? I had to get creative. The Utah State Fair example. that that deal was two million dollars per year for two years i made smith's grocery store buy four million dollars of drinks so i made around two million which was my cost basis the people of utah could buy their drinks from smith's grocery store if you bought a four pack or a 24 pack you got four tickets for five bucks each the normal ticket is 18 each so you were literally printing money and making free money.

25:49If you bought my drinks, you got free tickets for your kids. You're already going to go anyways. Smith's loved it because it was bringing all these people to buy the drinks and buy other stuff while they're there as the loss leader. The fair was like, holy shit. We just went from normally having 80 ,000 guests to 104 ,000 guests. You brought us 24 ,000 extra guests. I'm ecstatic because I'm getting a free sponsorship all over the state. Like, how can I fight with Coca-Cola? For 16 years, it's the Coca-Cola State Fair. I had to get creative in making the fair want me because from the fair's perspective, Coca-Cola just cuts a check.

26:22I said, I'll bring you more people. I'm going to get the streets to come out. I'm going to get people to show up. I'm going to get them to buy the drinks, show up, bring the can. I'm going to do cross-marketing, billboards all over town. And so I've done that my whole life. Again, hoverboards, energy drinks, clothing. It's all the same game of how do you fight with these guys that are 800-pound gorillas? Whether you're a brand-new artist, How do you fight with the household names that are getting all the radio play? You have to do creative marketing. And so that's been my whole life. So you said your philosophy on business changed and you'll never put all your eggs in one basket.

26:56So just talk about that as far as like even advice for entrepreneurs. Most people say like you should hyper focus on one particular thing. Right. Even Warren Buffett said diversification for people that don't know what they're doing. so talk about your philosophy as far as like anti yeah like focusing on one particular thing so in the beginning you have to focus on the one thing to to build a base once you hit a certain point whether that's 100 000 a million five million ten million it's all relative to your situation or your type of industry there's only so much you can invest cash wise back into the business not just diminishing returns but it's just you're not as good as the original you meaning the 27 year old when you're 32 it's a different person you don't necessarily know how to go from 10 million to 100 million and you shouldn't be putting all your cash in that's why you should be raising capital that's why you should be doing leverage that's why you should be getting loans credit debt facilities etc to go the next chapter and not you putting your own money in i'm not saying you necessarily have to go start one two three four other companies you have to either be the time wise to be able to do that the teamwork to actually go do that and the distraction sometimes can actually hurt your core business however when I say I don't want all my eggs in one basket is I don't go run the other companies I bring on a quarterback to run it so if you guys said hey let's start a vodka brand today if we didn't have a CEO for it and you said and you guys were going to put up 15 million to do it I still wouldn't say yes unless there's me someone to run it.

28:32And so when I talk about diversification, I don't mean necessarily I'm going to go do the other thing. I want to put my money, a little bit of time and capital into the other thing, but I don't necessarily want to go run something else because it'll hurt your core business. The hyper focus has to happen the first year or two, but at some point you need other executives or partners or staff to help you run that thing because you're not going to be able to scale it fully yourself. But my PTSD also comes from, I had a company for 10 years and then it As soon as I left, it went away. I had a poker site that was doing great.

29:04It's on television. It's on Fox Sports Travel Channel, ESPN. And now it's illegal all of a sudden? Like, I couldn't even, how could I account for that? And so in any industry, we just saw it happen to solar. We know hundreds of thousands of people working in solar. The big, beautiful bill just changed the whole thing. And so I don't ever want to be all in on a solar company in case something were to happen. so the long the long-winded answer is once you have some extra capital or some extra time you should have something else to bring in extra capital for you i wonder when you look at the landscape of gambling now it's wild right like you obviously you are early you look at i mean predictive markets i mean it's fan duel flutters oh it's all draft kings how do you i mean when you first saw this happening over the past i feel like during a pandemic it really spiked in your mind are you like i can't believe this shit or like i can't fathom it for a couple reasons one i would have gone to federal prison if i did sports betting during my poker site days the same reason that cannabis was so illegal back then and now it's on every street corner and every billboard sports betting was so illegal that calvin air the guy that owns Bodog, the brand I mentioned, wouldn't fly over America just in case he needed to stop because the FBI would have arrested him.

30:28That's how bad sports betting has been in my mind because that's what it was. Literally people wouldn't fly over. The guys that were bringing that deal for me that put up the$3.5 million, those guys had like 100 charges against them in America. If they ever come to America, they're all going to jail. Sports betting was demonized in America. And it kind of should be because no one can win sports betting. I don't care how smart you are. I don't care how good you are. There's a reason that the Wynn Casino has Encore. There's the reason that the Venetian Casino has three towers. Gambling, by definition, is a 53 % to 47 % game.

31:05Doesn't sound like a lot, that little 3%, 4%, 5%, 6 % difference when you're playing blackjack, sports betting, etc. On sports betting, they're taking a 5 % to 10 % for every transaction that you do. How can you fade that? in a game that's supposed to be 50-50, the house has 5 % advantage. Again, 5 % doesn't sound like a lot, but let's say that the three of us were playing coin flipping. You get 56 quarters, and you get 54 quarters, and I get 44 quarters. Can I beat you on some flips? Of course I can. But if you and I flipped for the next 10 hours, it's literally impossible because you've got 56 quarters and I have 44.

31:39You've got 53 quarters, I have 44. I can't beat you over the course of time. And so people that are sports betting and these prediction markets, are literally going to bankrupt so many people in our society. They're going to be in massive debt. They cannot win at sports betting. Talk about, explain this, the difference between a 54 and... So when you go to the casinos in Las Vegas and you play blackjack or you play craps or roulette, most of these games don't have that big of an edge. If you play perfect, by the way. If you don't know how to play blackjack, they obviously are going to terrorize you.

32:11But when you're playing these slot machines, blackjack, roulette, et cetera, they really only have 2, 3, 4 % advantage. That's also why if you want to get your free hotel rooms or free comps, you have to play four hours. Because over four hours, you can't beat them. You're flipping quarters with them for four hours. They've got 54 quarters. You've got 46 quarters. You play that game. They've got 55 quarters. You have 45 quarters. You can win any blackjack hand. You can win any roulette hand. You can win any sports bet. But over the course of four hours, over the course of 1 ,000 bets, if you've got 550 quarters and i've got 450 quarters how can i beat you at coin flipping that little five percent edge three percent edge four percent edge is why they have multiple towers at these casinos it's why caesar's palace has multiple towers it's why mgm like all these major properties have so many towers you can't win at gambling it is not possible over time it's just math i don't care if you're a wizard a genius it doesn't matter if you're the smartest blackjack player in the world and you're counting cards if you're counting cards they still have an advantage They just have less of an advantage.

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33:14And so it's hard for me to watch on the sports betting side because you're thinking about 18-year-old kids that are just like watching their friends bet. And they're like, I won a three parlay and a five thing parlay. That is a once-in-a-while situation. And you can win anything once in a while. But over the course of time, you literally cannot win at sports betting. You have no chance at blackjack. You have no chance at craps. This isn't an emotional thing. It's just math. Let's just all grab a thousand quarters and play. If you have 550 quarters and I have 450 quarters, how can I beat you over the course of time?

33:48It's not possible. That's the reason why they want to keep you there longer. Yes. Yeah. So as you're watching this table turn, is there an emotional reaction from you? Sure. Is it like middle finger to these people? I can't, like, what's that time like for you? Well, we're seeing it happen across the board. Again, I grew up with Ricky Williams living with me and I'm watching him lose his whole career. I grew up with Daryl Russell who passed away The people that had drug situations back then lost their careers over it Ricky Williams lived with you? Yeah In Vegas? In San Diego Oh Yeah, we went to Patrick Henry High School together Okay Why did he live with you?

34:24We lived on the same street And then when I was 18, I got an apartment right by the stadium And so him and Daryl Russell were both staying with me for months at a time And I remember he left the Ferrari Medina Spider in the year 2000 Which was like an impossible car He left it in my garage for like five months and I couldn't get out and uh, he At that time That was like around the same time he was signing with master p and he was doing these different deals He liked to smoke a lot and he ended up losing 8.8 million dollars He had to pay back to the miami dolphins like I so for me when I Watch what happens with cannabis or I watch what's happened with sports betting and now Everything is flipped.

35:02I do have an emotional reaction to it because I watched it ruin Darryl Russell who was my roommate passed away you know he's number two guy on the Raiders and now he's gone I watched Ricky Williams who would have broke every NFL record possible the way he broke every college record he doesn't have the same career that he would have had simply over cannabis and now look how big it is and so I'm seeing that happen in sports betting where people are gonna lose everything they cannot win at sports betting it is a mathematical impossibility I don't care how smart you are I don't care how sharp you are you cannot win over the course of time because you're paying 5 to 10 percent so even if you're really good you still have to pay the house draft kings and calci and all these different polymarket etc they take a percentage of every single bet as they should it's a huge operation for them they spend tens of millions of dollars in regulation they need to make a ton of money but the 18 year olds and the 26 year olds and the 70 year olds that think that they can win at betting it's not physically possible it's not mathematically possible it is not possible over the course of time anybody can win one or two or three bets.

36:04Last night in the Jake Paul, Anthony Joshua fight, you could bet on, are they going to mention Logan Paul, the commentators? You could bet on, are they going to mention the word YouTube or YouTuber? You could bet on Jake Paul by knockout, Jake Paul by decision. Over a hundred million dollars would bet on just one platform on Jake Paul. He can't beat Anthony Joshua outside of a lucky punch. Think about the massive amount of people that bet last night. Their hundred is never coming back. And the people that won, it's even worse. The people that won think that they know how to bet now. And they're going to go do it again and again.

36:41It's just like when you see slot machines. Someone wins a slot machine, they win a$600 jackpot, they end up losing thousands of dollars. Because they remember the time that they won. They can't wait for the college football today. It's confirmation bias, right? You talked about, like, at a certain point, you shouldn't use your own money anymore. Yes. And you should be raising capital or getting leverage or loans explain that because that capital is something that you know a lot of entrepreneurs struggle with and it bankrupts a lot of businesses because they don't know how to go about raising yes capital they don't know what the different tools that's available to them so talk about that so far and away hands down the number one reason that companies fail is they run out of money point blank end of story there's a lot of great entrepreneurs, a lot of great ideas, a lot of great passion, but most restaurants that fail run out of money.

37:34They might have two or three bad months. They don't have two or three months saved up. They're running a clothing brand. They crush it. They actually get a bunch of sales. They can't afford to factor. They can't afford to wait. I'll give you a real life example. With the energy drink, I got an order from Costco and the opening order was$1.8 million. Sounds great. I need around 900K to manufacture it. So let's say that the order purchase order came in January 1st. That means you don't ship until March 1st or April 1st. That's when they're ordering for us three to four months out. Once they get the product, they pay you on net 30 or net 60.

38:10So let's say they pay net 30. That means by May 1st, if I'm lucky and everything goes perfect, I get paid. But I put up the 900 grand January 1st. Let's say May 1st comes around, but my drinks did well. I actually sold. Let's say we did it, which is actually what happened. they made a new order for 5.5 million dollars i didn't get paid on the first order i needed to try to figure out how do i get 2.7 million to fund the next order i haven't been paid yet at the same time i had ralph's albertson's save on cvs walgreens tens of thousands of liquor stores that were slow paying me think about how much capital i needed even though i looked successful i needed capital at all times this happens in clothing happens in shoes.

38:55It happens in almost any physical product business. You need so much capital to be successful. That's why you see so many of these food and beverage brands and clothing brands, etc. raise capital all the time. It's literally waiting for money. The cash flow part of it. Nowadays, there's a lot of options. You get an order from Costco, you can factor it. Factoring will pay. It's very expensive. They can charge you one to two percent per month, but they know they're getting paid because they're buying the papers, what they call it. They're buying the invoice from Costco or Walmart or Target. It helps you with your cash flow.

39:29Back then, that didn't happen. So you can factor the paper. If you have sales, the second you have any good sales, you should be getting different credit cards and any type of loan from a bank. Not necessarily you have to draw down on that line of credit, not necessarily you have to use those credit cards, but when you've got sales, when you've got revenue, is when everyone wants to give you money. When you need money and you don't have money and you're waiting around and your bank account has$600 in it, even though you got 200 grand orders, what banks are going to give you money? They're not.

39:56And so what I tell the entrepreneurs or what I tell the companies I invest into, when you can raise capital, when you can get debt, when you can get a line of credit, when you can get credit cards, please, by all means, get it. You don't have to use it, but get it. If you try to go raise capital when you've got the 600 bucks in your bank, do you want to invest in my friend's company that has$600 in the bank? Probably not. If I told you that they've got 250 grand in the bank, a million dollars in orders, I could text you guys about investing You wouldn't be that excited if I told you Well, they got 600 bucks, they actually can't make payroll On Friday, but they got a million dollars in orders That's a gamble, right?

40:31That feels a bit sketchy And so when you have capital is when you should try to get capital Now, clear that slate If you're just starting up The only true options are Go get sales Leverage yourself, which is A big gamble and most people don't want to do it Or friends, family, and fools The Friends, Family, and Fools are the only ones that are going to give you money in the beginning. You're not cutting a check for$100K into some guy's brand new clothing brand or brand new selling palm trees. Their new thing, we're not cutting the first check because we're not in the Friends, Family, and Fools category.

41:05They have to go get money from the Friends, Family, and Fools. When I first started the clothing brand, I was getting$25K checks and$50K checks. A new year doesn't mean erasing who you were. It means honoring what you've survived and choosing how you want to grow. It means giving ourselves permission to feel what we've been holding and knowing that it's okay to ask for help. I'm Mike Dallarocha, host of Sacred Lessons. This podcast is a space for men to talk openly about mental health, grief, relationships, and the patterns we inherit, but don't have to repeat. Here, we slow down. We listen. We learn how vulnerability becomes strength and how healing happens in community.

41:47not in isolation. If you're ready to let go of what no longer serves you and step into the year with clarity, compassion, and purpose, Sacred Lessons is your companion on your healing journey. Listen to Sacred Lessons with Mike De La Rocha on America's number one podcast network, iHeart. Follow Sacred Lessons with Mike De La Rocha and start listening on the free iHeart radio app today. New year, new goals, and in this economy, a better money plan is more necessary than ever. I am Matt. And I'm Joel. We are from the How to Money podcast. And every week we help you to spend smarter, save more, and make sense of what's going on out there.

42:25If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice to help you make it happen. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey, what's up, y 'all? This is Questlove. Recently, I had the opportunity to sit down with A$AP Rocky ahead of his album release, Don't Be Dumb. He reflects on his journey from his Harlem roots to global icon status, discovering the hip-hop origin of his name. The ledge was on the TV. Rakim had the bucket hat Kangol during it. Pops was like, that's Rakim.

43:00That's who you named after. I just was like, damn, that f***er got swag. Rocky offers a window into not only a boundary-breaking artist, but as a man committed to fusing creative ideas, community, and remaining unapologetically himself. Have you ever gotten roasted for any of your outfits? For sure. Some people don't be getting the vision. Look, they can roast me, they can cook me, they can deep fry me, they can saute whatever they want. It's nobody who can f*** with my fashion sense and my taste is impeccable. I'm just like, I impress myself a lot. It's an amazing conversation. One you definitely don't want to miss.

43:38So listen to the Questlove show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

43:47What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. NLP, a.k.a. Neuro Linguistic Programming, is a blend of hypnosis, linguistics, and psychology. Fans say it's like finally getting a user manual for your brain.

44:24It's about engineering consciousness. Mind Games is the story of NLP, its crazy cast of disciples, and the fake doctor who invented it at a New Age commune and sold it to guys in suits. He stood trial for murder and got acquitted. The biggest mind game of all? NLP might actually work. This is wild. Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. My mom was making$2 ,200 a month for a family of four. So for her to give me, the money she gave me was three grand. And I still hear about it today. She still talks about it 26 years later, right? That was such a big deal for her.

45:03And it changed my life because that three grand helped get me that my first convention before magic. Like the only way at the very beginning is to friends, family and fools, credit cards, go get sales because sales cures all. If you go get sales, you can get investors. You go get sales, you can get loans. You will get sales. People will flock to you, whether it's staff, executives, partnerships, deals. And so I focus my life in every business that we can talk about. I focus on getting sales if I can make it famous if I can get retailers to buy into me People will then give me money Other retailers want to buy from me and it goes across every category and too often people just have an idea or a business plan And they don't go try to sell it first If someone pitched us on a clothing brand that they had on a business plan, we're unlikely to invest But that same guy came to us and said hey I went and met with 40 stores last week 26 of them said yes Six of them actually wrote me an order.

46:01I got 80 grand in sales I'm down. I'll invest and maybe you guys will too. The difference is someone else just brings a business plan. We don't know that they're actually going to go try to sell it. And so there's a lot of ways to get capital now. And on top of that, more than ever, is grants. The grant industry is wild because so many of these major corporations, funds, cities, etc., they have to deploy the capital. And so you see a lot of people that are doing grant writing as a whole business now because these grants are real. Like they are very, very real. And a lot of them are in Marcus's group and Hymn 500's group because I've met some of them.

46:40And they're crushing it, helping teach people how to go out there and get these grants. Grants are literally free money. And it is prolific now because of how much capital has to be given away to certain categories, whether you're a woman, different culture, different age group. there's so many different categories that you can go apply for different sections different businesses what county you live in etc go applying for these grants is literally free money you should have someone dedicating an hour a day just applying for grants if it shows up great if it doesn't you have no risk involved besides the time okay and and um okay now let's talk about social media yeah Let's navigate to that.

47:20How'd you get involved in that? And let's start there, because I have a multi-level conversation with social media. How'd you get involved in social media? When I first started, it was MySpace, right? And then Twitter. And I was just posting on social media, watching people post. And I was trying to get my brands out there because it was free. the difference was after the Black Friday which shut down online poker I started angel investing in some companies and I wanted to help them get more famous and so we went and paid different influencers to post but the word influencer didn't exist in 2011 I would pay celebrities to post or I would drive like that refrigerator you have in the corner I remember driving to Britney Spears' house to bring my energy drink refrigerator I used to drive to Omarion's house and bring the refrigerator there and I would go replenish it with drinks and I would drop off clothing.

48:14I would drive to music studios all over LA and put it in there. I would just implement. Why? Because the social media was free and I just wanted to be around. I wanted them to wear my clothes, have my drinks. I would just implement it into them. So when I started paying people to post on things, I noticed how much for like a thousand bucks, five grand, 10 grand, they could get millions and millions or tens of millions of views because it was the wild, wild west back then. And so I started a social media agency called One Penny Ad Agency. The concept was every penny was worth 100 views back then.

48:50Now it's obviously tiny based on the algorithms. There was no real algorithm back then. And so for like 10 grand, 25 grand, I could give people millions of views. And so I started the agency and I was driving around Fashion Nova dresses to Kylie's house and Kim's house. I was dropping off Fit Tea and having Kim post about Fit Tea for like 25 grand, 10 grand. Now it's half a million or a million dollars. And so I was just embedding myself and go to Tyga and Blac Chyna and literally just drop off products. Hey, will you post about Fashion Nova? Hey, will you post about Fit Tea? Hey, Amber Rose, here's 10 grand.

49:25I have so many stories in my mind of making her a rose full of cash to do her posts for fashion brands and then bring her products to post about supplement companies, tea products, fashion brands, etc. And so I just was embedded into the space because 2011, 12, 13, 14, who was my competitor? No one. And so I was just making up prices and driving around brands, making my own random products. I was selling like curve control bras for girls. I was doing eight grand a day in sales selling bras. I don't know anything about bras. I just knew that if I post about bras on social media, we were averaging$8 ,000 a day in sales, spending$1 ,000.

50:04Spend$1 ,000, do$8 ,000 in sales. Our cost basis was$4 ,000. We're netting$3 ,000 a day. That's a good business. Do more of that. Are you multitasking, diversifying the products? Because it's the drink, but then it's the merch. And as you're seeing more things work, you're like, wait, we need more products? Yes. And so because I got experience. As an agency owner, you get experience because you're spending other people's money. If I'm spending money for Fashion Nova, I'm spending money for Fit Tea, or I'm spending money for Pretty Little Thing and Boohoo and Nasty Gal, all these brands, if they gave me money, Siroc Vodka, if I got money from Siroc Vodka, I learned what would work.

50:39I learned what the engagement would be like. I learned what the captions should look like. So for the first nine years, I would write all the captions. For the first nine years, I would drop off the products to the people's houses. I was going to be out in front of Tiger's house and make sure he got paid. I signed the contract. I gave him the product. I would sit at Blac Chyna's house and Amber Rose's house. I was going to sit with them and make sure the post, I would take the picture if I had to back then because who was going to do it? There was no videographers or photographers back then. That wasn't a career back then.

51:08It wasn't a thing. And so that's why I got into it. I was living it. I was just there spending the money for these brands, and I started to make my own products along the way. And then that evolved into you doing it for yourself. Yes. And you becoming an influencer. Talk about it. So where did you see the pivot from actually just doing it for other people or doing it for yourself? and then doing it for yourself because even that as far as business that's something that came later on as far as like a business influencer courses click funnels that did that wasn't always part of the online thing either yep and i still regret there's a lot of time i just didn't do it for myself i'd be in a lot of rooms a lot of situations a lot of celebrities and i didn't take the picture i didn't do the video i didn't post about it i was doing it for everyone else and there was times where I was spending millions of dollars a month for brands, like Bilzerian's Ignite brand.

52:01That campaign was$650 ,000 a month to pay influencers to post about it. The Fit Tea and Happy Tea and those brands, those were$300K,$500K a month. At the same time, there was business guys that wanted to get famous. Tai Lopez, Grant Cardone, a lot of those type of characters were spending six figures a month to get famous on social. Why? Because then they could leverage it to sell courses, products, books, raise capital. A lot of things would happen because they were able to get fame and personal brand. I started running contests. I started doing all these different things to help people build their personal brands.

52:36We did follower contests. Jake Paul is going to post a giveaway. Kim Kardashian posts a giveaway, giving away purses or giving away prizes. All you have to do is go follow Ian, go follow Troy, go follow Rashad, go follow, earn your leisure. If you go follow that, you have a chance to win these purses. You have a chance to win these cash prizes or a car. And so I was running it with Jake. I was running it with Kim. I was running it with these follower campaigns. And I was watching what would happen when these guys got famous. Well, we've seen what happens. They become huge brands now. So the turning point for me was 2019.

53:08I finally hired a CEO. That was eight years or nine years of running around with the social media agency. It was called One Painting Agency. I changed to Elevator Studio around 2015. this ceo had 30 years in the tv game and so i didn't know that i could afford him i didn't know i could bring him on i was doing 18 million in the influencer space with elevator studio he's mid six figures plus equity and i never gave up any equity in elevator studio i never raised any money because i was just doing influencer campaigns that was the biggest turning point this guy was the ceo for beuna murray so the first eight years he created real world, simple life, road rules, all those shows.

53:49He was the CEO for eight years. Bringing that CEO on changed everything. We went from 18 million to 60 million in one year. It allowed me to start my mastermind group. It allowed me to start my personal brand. I started speaking at events. I started throwing events. Everything started when I brought on that CEO because I became unshackled from the office. I could finally leave the office, go out there and be on stages, network, bring in clients, and everything changed from that moment. That's when I really started the personal brand. I had my social media out there the whole time since 2011, 12, whatever.

54:21But it really didn't get big until 2019. That's when the turning point happened because throwing events, making content for myself, speaking at other people's events, that's when it all changed. The powerful thing in that has kind of been the theme throughout your story thus far is that these relationships that you have are fostering new opportunities to you. number one from a working standpoint, working capital, but also from the standpoint of brand ambassadors, right? And opportunities to invest. I know you said you invested in over 43 companies. Are you finding them at this time? Then saying, hey, this is a cool product.

54:56Not only do I want to be part of this campaign, how do I get equity? How do I get ownership? Are you doing that at this time as well? Yeah. So some of the clients I've tried to invest into are trade for equity. I was throwing an event called Elevator Night for free, which I still throw to this day 58 times. free event, 300 to 1 ,000 guests, come there and pitch kind of like a shark tank for five minutes each. If you raise any capital here, I take nothing from it. So it's free to attend, free to present. I just wanted my excuse to get my investors to come there, get speakers to come there. So I've had Russell Simmons and Jake Paul and all these guys speak at the event for free because it was a free event and it was just good for the community.

55:36I would throw those events and I was cherry picking. I would find a food and beverage brand. I would find a clothing brand. I would find this new snack company. I would find a shoe brand, etc. From during these events. So the events would bring people to me. Everyone's posting about me and the company's there. They post about the Elevator Night brand. Elevator Studios, my agency. Now they post about Elevator Night. And so the free events was what brought everyone to me. And then I would find these deals. There was a one called Dollar Beard Club, monthly box for beards. they obviously got sued by Dollar Shave Club later but we had 77 ,000 subscribers along the way paying 20 bucks a month so it was a good business I found that from an elevator night I found a snack company which I later put in 4 million into that brand because it started to crush it I found them when they were this big from throwing the events and so I like now only focus the last 3 years on companies doing 2 to 20 million revenue the reason is 0 to 1 million is super hard 1 million and 2 million are the same thing but 1 million and 2 million is when I know that they have some processes 2 million to 20 million is when they're starting to get it together starting to find the right flow the failure rate is much less when someone's doing 9 million than doing less than a million so I don't invest in startups anymore I just find companies that are doing 4 million, 8 million, 15 million, that range I raise them 3 to 6 million dollars for the company and I've raised 56 million the last 2 and a half years on this exact model.

57:07Finding companies doing that$2 to$20 million is my sweet spot. It's not that I wouldn't gamble on a startup company. It's that I wouldn't feel comfortable asking you guys to invest with me. And so I'm only finding companies that are doing over$2 million so that I can get smart friends, strategic investors to invest in the companies with me. If Dan wants to gamble, throw in$100K onto a deal, I'm gambling, but I've never texted you guys like, hey, invest in the startup ever. Because if it doesn't work out, it's on me, right if it coming to 7 million and goes bankrupt it's less likely you'll be mad at me because they had a real shot at it they're a real business they really went for it if i brought you into a deal because my boy's starting a company i try to avoid those situations because i had those situations in the past when you said when you got the ceo i went from 18 million to 60 million yeah what what was the biggest difference for that jump in that year one i was running the entire business myself.

58:00I literally wrote every caption. I literally did every contract. I literally drove the products to these celebrities and influencers' houses. I shipped the product. I did everything. And so the biggest difference was I wasn't doing the little stuff anymore. I wasn't running the day-to-day operation. I was now being at events. And because I'm at events, I'm meeting clients. Because I'm speaking on stage, people are asking if they can do social media through me. when they ask about doing social media through me I can pass them on to the CEO now and so me being out and being the brand ambassador for Elevator Studio allowed me to bring in more clients and more deals we ended up doing partnership deals with other agencies so we started doing influencer marketing video content for BET Television 2019 that came from me speaking at an event another big agency was doing other work for them for BET and boom, Oracle.

58:57Same agency was running Oracle, running one division of it, but they didn't do influencer marketing or video content. I got the Oracle exclusive for the last half a decade because I was speaking at events. Those guys were there. We ended up doing a deal together. They still did what they did. We did influencer video and all of a sudden, we're getting all this work because I'm out there in the streets. I'm out there in the field. I'm out there on stages. Me being the social butterfly out there allowed to bring in more clients while having a CEO run the operation. And so a lot of times people worry about doing partnership deals or having a partner.

59:33Your partner should be very different than you. If you have two partners that are the same, that are either both introverts or both extroverts or both love accounting or both love to be in sales, you need to have that counterbalance. And so I had a CEO that just loves running the business. He doesn't want to be on stage. he doesn't I didn't notice I didn't even mention his name here he doesn't want to be known in that like he wants to be the guy running the show running the operation I want the name for the not for the ego part of it the function part of it I want to be famous for function the same way Damon John needs to be famous for function the more famous Damon John gets the more famous I get the more deals come in the more partnerships come in the more brands come in the more clients come in the more stages the more speaking events everything happens from fame from personal brand problem.

1:00:18It's a lot. I'm sitting here and I'm thinking number one Dan must have a photographic memory because he hasn't missed the details since 99 but i also wonder how financially disciplined or how did you get so financially disciplined because we're not talking about small sums of money 65 million dollars deal going in 2009 you're talking about hey we went from 18 million obviously the company did to 60 million how are you managing money or have you always been strategically disciplined when it came to it so i'm disciplined in the sense that i i have a intense value of money but i'm also a gambler i'm willing to take risk and i know that if something doesn't work out i'm going to figure out how to make my comeback i've had it what happened with online poker losing 65 million overnight didn't mean i had another 65 million it mean i had nothing and i started the agency and the the deals and consulting like built myself back up.

1:01:20So I've disciplined in the sense that I'm obsessed with investing. I have this one thing that I talk about at every event and every speech and podcast is called 40-40-20. I invest 40 % low risk, 40 % medium risk, 20 % high risk. I've talked about the same strategy my whole life because that's my only thing that keeps me balanced. If it wasn't for 40-40-20, I would be so all in on the high risk because I don't care about being broke I don't care about making a comeback I have no emotion or ego about failures I'm going to have failures because I take a lot of shots and so because of that I would be so heavy investing in just high risk because I have such high risk tolerance I've been through the hardest things in the world I've lost millions, I've had people die I've had all the situations that can come from it so I have no emotion to losing it all so the 40-40-20 thing is I want 40 % low risk that does like 5 % to 9 % for the year.

1:02:16I want those things to be boring. I don't touch it. That's my discipline part. The medium risk is what most people like, 10 % to 30 % for the year. Real estate, stock market, cash flowing businesses. That's what I enjoy. That's what most people enjoy. That's investing in things like that. Real estate, stock market, cash flowing businesses. The 20%, the reason it has to be 20 % or lower is this is high risk. This is cryptocurrency. this is angel investing i have passions for these things but i would be very heavy into those if it wasn't for me having discipline over here very strategic um okay social media back to social media a lot of people may have followings everybody wants to be an influencer these days but very few people really have figured out how to really really make money online a lot of people have followers or they are influencers and they they have podcasts and they um they don't they haven't figured it out right they're waiting for ad deals that's then that's their way or they're trying to find how to get brand partnerships to do commercials if you are advising somebody somebody has a following somebody's an influencer break down you know a business model for them in 2026.

1:03:29You said the perfect few words. They're waiting for ad deals. It's not just going to show up in their bank account. They're not just going to knock on the door from Coca-Cola or Gatorade or Fiji Water. It doesn't just happen like that unless you're a big, big, big name. To stand out as a social media influencer, a podcaster, anyone that makes money from brands, you have to actively reach out to them. It is free to do. you have access to them through social media linkedin twitter email carrier pigeon i don't care how you get a hold of them you actively reaching out as an influencer you will make some money you actively reach out because you want a podcast deal or you want people to endorse your podcast you can get people to do that i'm not saying you're going to go get millions of dollars but can you ask for 500 bucks an episode when you first start out yes and you might get three or four people do that well if you put out four podcasts a month two grand episode and you're making eight grand a month, that's a hundred grand a year.

1:04:27And you're outpacing most people in our society to do a podcast an hour a week. People don't reach out. In the influencer game, I've been preaching this for the last 15 years. If you want to get with a clothing brand, DM them, message them, tag them. If you want to get with a beverage brand, message them, DM them, tag them. It's easy to find the executives of every brand in the world. If you go through LinkedIn, in, go through Twitter, search online. You can get a hold of anybody you want. You can get a hold of any buyer, any brand, etc. Most people do exactly what you said. They're just waiting.

1:05:02They're waiting and expecting it to work out. It literally doesn't work like that. The influencers that go out and make money are the ones that just go after it. They want to get a fashion deal, they go message 40 different fashion brands and four of them respond. How much does it cost you? Nothing. You just copy and paste it. If you want to go out there, I will also say this very practically. Make a one-page PDF about you. Here's your Instagram, your Facebook, your LinkedIn, your Twitter, your Snapchat, your TikTok, your YouTube. You put all your major platforms on one page. I've got 12 ,000 followers here, 100 ,000 followers here, 3 ,000 followers here.

1:05:41You put all your platforms there. one paragraph about your story, your phone number, your email, how to get a hold of you, and what your three rates are. One post, one month, one year. If you send out to brands and you send out to 50 brands, some of them will respond. If they don't, it costs you nothing. But what if they do? And I've watched it work so many times. And if you just send those out on a daily basis, so the brands that you want, and the next thing I'll say is, also practicality, think of yourself of what you eat what you drink and what you wear what you use on your phone those are the brands you should reach out to you like certain brand of shoes go get a hold of them you like certain types of pants there's eight brands that you like message those eight brands repeatedly I'm not saying to annoy them every single day but every single week or month keep messaging those brands and look at yourself as what you eat drink and wear and use that should be your categories Try to get a hold of Cash App, Wells Fargo, or Stripe.

1:06:43Try to get a hold of Gatorade, Fiji Water, etc. Try to get a hold of this brand, that brand, or that brand. Try to get a hold of the brands of every category for sunglasses or earrings or hats or shoes or socks. You like to wear socks a lot? Everybody wears socks. Is there certain brands you like? Go get a hold of Bombas from Damon John. Go get a hold of Nike because you like Nike. Look at yourself at every category and try to get someone to sponsor your food, your beverage, your protein, your credit cards, whatever the things you use. You like Robinhood? Get a hold of Robinhood. You don't like Robinhood?

1:07:14You like Polymarket? Go message and tweet at Polymarket. The downside is zero. But what if two of those brands hit you up and say yes, and they pay you two grand or five grand a month? Too often, people are just waiting and hoping that it's going to come to them. Waiting and hoping is not a strategy. It's not work. You talked about, I mean, that's interesting, right? You talk about alignment, that's what I'm hearing. you talk about consistency and being optimistic right having that idea like yo this could work waiting game obviously is something that's not going to work what are some other things that the people who are doing the influencer marketing what are they doing right that the others are doing wrong right so like if i'm not getting this right right now what are the things i should look inside myself self-reflect and say oh i gotta change that yes most people's social me to post about themselves, not about their fans, not about their audience.

1:08:09They're focused on their ego. They're posting the perfect, look at me, I was working out. Not, hey, I lost 18 pounds because I took first form supplements. I did 75 hard. I drank water every single morning. I did this to sleep. Not teaching them anything. They just showed them that I'm buff. Girl posted a hot girl bikini picture. Doesn't say, oh, this is how I lost 11 pounds. This is how I keep my bikini body like this. This is the supplements I take. This is what I do. That post will do really, really well because you're making it for your audience. If you make it for yourself, we're not going to keep engaging.

1:08:44There's only so many times we're going to put the fire, fire, fire emoji. There's only so many times we're going to tell you how good you look or how hot you are. You've got to teach us. You've got to make us laugh. You've got to show something interesting as your followers. Most people's content is for themselves, not for their audience. and they wonder why it goes down and down and down in engagement because what are we supposed to say on your seventh selfie? What about your 70th selfie because we're following you for a year or two? What about your 700th selfie? What do you want me to say? I'm not going to keep doing that over and over and over.

1:09:14Tell me where you bought that shirt from. Tell me why you did this. Tell me why you're going to this movie theater. Tell me why this funny thing is happening. Tell me why you thought Anthony Joshua was going to win. Tell me why you thought this happened in politics or government. Talk to us. Most people do it for themselves. Most people do it for their own ego. The other problem is their captions are way off. Captions are based on human psychology. If we cannot read the sentence or the paragraph, we're not going to read it at all. And so when people are tagging, here's the photographer, here's the makeup artist, here's this, here's that.

1:09:50I don't know to go follow Fashion Nova or Pretty Little Thing. I don't know to go buy from this product or brand because you tagged five other things. if you're trying to get us to buy from you like buy your course or buy your product or buy your personal training program if you tag for the things I'm not going to see that if you give us too many options we choose none and so people's comments and captions section it's just bad because it's unreadable they're putting in inside jokes or they're tagging multiple people in it we are not going to read it if we're not going to read it we're not going to take an action Instagram stories If you wouldn't want to see it, don't post it.

1:10:27If you don't want to see someone's salad, don't post your salad. If you don't want to see someone posting the floor for six seconds before they pan up, don't post the floor for six seconds and then pan up because the human that's scrolling through makes a decision within three seconds if they're going to watch. So in the first three seconds, we're going to make a decision. Why are you starting off with showing the floor before you show us the nightclub you're at or before you show us the office you're at or before you show us New York City or Paris? make your content about things you want to see make your content of what you want your audience to learn from you make it valuable and people will follow you so as far as um monetization you talked about like from an influencer standpoint reaching out to brands in our world as far as like people that have businesses or like online business people right talk about that as far as it's become very popular over the last six years click funnels and events and courses and ebooks what is your advice to people to galvanize a community and actually have some level of monetary compensation for value add so you have to do what's called setup shop you have to choose a platform like click funnels or go high level i use go high level now you have to find a platform to be your back end like fan basis or one of those brands set up shop so that you can accept money easily set up every single social media platform because you have to build what's called omnipresence you know if people if you love Twitter if you love Facebook and I like Instagram that means that he needs to be on all those platforms because you don't know where your audience enjoys to take your content in and I might follow you on multiple platforms but not see you on every platform because of the way the algorithm works so you have to be on all six major platforms you have to have your own website so it's easy if I want to go down the rabbit hole because I'm like oh man man, I really like your content.

1:12:19I really want to buy from EYL University. I need to be able to go to that website, that landing page, and make a decision. Your purchase order, the way to buy your add to cart, has to be what's called above the fold. Meaning, if I go to EYL University, for example, on the top of the website, if I'm on my phone, it should be on the very first page. It's called above the fold. If I have to scroll even a little bit, your engagement's way down, your conversion rate's way down. even to scroll which takes me no effort besides doing this above the fold so if you guys are building it you need to have your website your social media your bio your photo everything seamless because we as a community have add and it's getting worse the reason that vine and tiktok and short form video youtube shorts it's called youtube shorts for reason because we have a short attention span.

1:13:12Because of that, you've got to make it very simple. When someone sees your social media on every platform, they see your website or they see your checkout page, it has to be easy to buy from you. You can't have just one option. You need to have Apple Pay or Bitcoin or Cash App. Any way that they can pay you, you should be able to accept money. Too often, people have one way to check out. You've got to have multiple options for the payment processing. That part is super, super important if you have a high ticket like you're selling a course thousand dollars or more you need to have something that allows you like a fan basis type company that allows you to do payments that allows you to for people to pay you 100 bucks a month instead of a thousand bucks up front for example you need these things to happen because you need to act as if they're going to buy from you and we know if there's any friction it's unlikely we're going to buy what do you do when you go and you add the cart and there's some pop up and this happened that happens you exit you leave.

1:14:08You have to have no friction for someone to purchase from you. And so this is super important. So when someone first sees you, it's easy to understand who you are. When they first see you, something's appealing about it. So your bio should have some highlights in it, what you've done or what you care about. When they actually take the step to go to your website or click your link or click on your stories and go to want to make a purchase decision, they have to make a decision right away. If someone has come to your website to make a purchasing decision. You've got to offer it right at the very beginning above the fold.

1:14:39Below that, you're then justifying who you are, why they should buy from you. Buy my fitness course, buy my stock trading course, buy my credit repair course, whatever that thing is. You've got to explain all that below the option because a lot of people are going there ready to make a purchase. So the long-winded answer is setting up shop, making it very easy to find you. Once they found you make it easy to make a decision once they made a decision make it really easy to pay you this is a tricky part because before that it's like you have to build a relationship you have to build a community but you don't want to always sound like it's transactional no so like how to does one balance that yep so the famous gary v line the jab jab jab right hook that book that concept is very good the jab jab jab right hook concept is monday you're posting fitness Tuesday, you're posting with your dogs.

1:15:33Wednesday, you're posting fitness and with your kids. Thursday, by the way, I have this program. I can help you lose 15 pounds in six months by my course. Friday, you're posting with your friends, going out to the club. Saturday, you're posting hiking and yoga. Sunday, by the way, guys, guess what? I have a 50 % off by my course. Posting from church at 1 p.m. Have your Sunday night, blah, blah, blah. Monday, you're posting the jab, jab, jab is you're posting your content, teaching them, making them laugh, showing your lifestyle, making them buy into you because there's hundreds of thousands of people selling the same exact type of fitness course.

1:16:07Hundreds of thousands of people can offer how to lose 15 pounds in six months. Lots of options for that. They are buying into you. And the way to build you is to make people want to listen to you. They want to watch you. The reason we buy from certain characters and the reason we buy certain products or programs is we like that person, that storyline. We have this in our minds, something about their story. Us, as humans, remember stories. We all know 50 Cent got shot nine times. Why? We all know Lil Wayne's the greatest rapper alive. They tell us it in the songs, on social. That's burned into our minds.

1:16:41There's a storyline to them. And because of that, we want to buy their products. And the product is fungible. It could be anything. Whether they're selling vitamin water, whether they're selling products, whether they're selling movies and TV shows like Power. We think of 50 Cent for different parts of his brand, but we all remember this famous thing from 25 years ago about him getting shot nine times that is a story that we are bought into and so when you think about certain characters you have to build that brand up the way that you build community is that you are teaching them making them laugh showing them something interesting or showing them something timely it's four things funny interesting something timely or something also in their in their space meaning can it be something that's going to help them in their life.

1:17:25If it's not, they might refer you to someone they're never going to buy from you. If you teach them something, they'll afford it to their friends, they'll repost you, they will buy into you. If you make things about yourself, they will not think about you in the community because they think of you as selfish. If you are teaching people and making them laugh, you guys obviously are teaching people in VestFest, University, etc. Because of that, you have very passionate people that will buy from you. Very passionate. Because day after day, you're teaching them about stock market, how to invest, how to trade, you're showing them other characters through your podcast.

1:18:00You guys are the perfect example. That's why I'm always so passionate about your brand over these years. I've been obsessed with what you guys are doing. You're throwing these live events, you're teaching people, and the butterfly effect is far greater than you'll ever know. When you teach people and they go out there and make their own money, or they build their own business, and they open up their four restaurants in their community, that creates jobs, that creates things in their community, in their city. to me it's almost like a form of charity what you guys are doing almost has a form of charity to it because you're creating people to make their own money far greater than you'll ever know 25 ,000 people go to invest fest 600 of them go out and create businesses make partnerships and deals 200 of them start dating and creating babies and get married there the butterfly effect of live events and teaching is why you have such a strong passionate community that's also why i've been one of your biggest fans watching you guys because of the butterfly effect of what it does everything i just said, think about the emotion of how I said it.

1:18:52It's because I am a follower of you guys. I've been learning from you guys. I have watched what you guys do. And so I'm the perfect example of I would buy from you because I've watched what you do for other people and I've watched what you taught me. Anyone that's listening can create that same thing only if they're actually really good at it. You have to be really good at real estate to teach real estate. You have to be really good at fitness and helping someone lose 15 pounds because you actually know how to do it. But competence leads to confidence. If you get really smart and really granular and get really good at a topic, whether it's stock trading, credit repair, fitness, health, et cetera, people will believe you and people will buy from you.

1:19:29But you have to get really good at it. You cannot fake it until you make it. You have to actually get good at it. Before we leave, talk about events. Talk about your events. I don't know. You do events. Yeah. You recently just did an event, right? Oh, yeah. So talk about that as far as how you got into the event space, how you've scaled that and your thought process around doing events So I throw 42 events a year and I call it free Cheap affordable. Holy shit So free is elevator night totally free throwing it 58 times 300 to a thousand guests. It's a pop-up event. So we don't tell anybody until a few days before it goes because it's free Cheap is Aspire tours like 100 bucks to 500 bucks.

1:20:10Those events are 12 times around the country I have what's called the man in the arena tour. It's an all-men's event We get a couple thousand men in there one day intense experience We bring in david goggins and bring in very intense to help men get better and stronger for their households and communities 100 bucks to 500 bucks. So that's the cheap affordable type Affordable on the mastermind side is we do like 2k to 5k boot camps we do a 20k mastermind like things that are affordable to help people really grow their business that are already doing a million two million five million holy shit is i have one called the 100 million mastermind experience it's a hundred thousand dollars per person it's a hundred people that do 10 million or more in revenue though that's my seventh year coming up in january is my seventh year of throwing that event that also started back in that story of the hiring the ceo i started it right after i hired the ceo hundred thousand dollars per person i sold 100 spots in two months.

1:21:03That's$10 million in revenue. So I thought it was too expensive to hire that CEO, but it changed my life because I created this mastermind from finally having more time. The live events to me is something I'll be doing for many, many years. And live events will be more important than ever. You heard recently the owner of Endeavor and Gary Vee keep talking about it and Elon Musk. Live events will be the only true commodity soon because if people don't have to work as much or people their jobs give them more time they're going to go to live events more than ever if they're scrolling through and dealing with ai and social media too much in person becomes the true commodity people are going to go to events more than ever so i've quadrupled down on events i partnered with events.com it's a huge company in san diego i'm throwing these 42 events a year as often as i can because i truly believe that people need this they need to come together they need to come to invest fest they need to come to these events and so i'm going to keep doing these events for the rest of my life incredible you talked about before the who's your daddy thing yeah so as a yankee guy we we know 2003 pedro says that just for shit to get how did that how did that come it was interesting scenario because i loved it right it was on the cover of every newspaper magazine television it was like chanting who's your daddy like it was great and um but i do own the trademarks and i do own the clothing the brands I own it for barbecue sets and physical products, greeting cards, paper, everything.

1:22:3216 different classes, 300 products. And so I went to the MLB. I'm like, I want you to do this. This is great. But I'm at your stadium and you're selling the shirts. You can't do that, right? Unless you give me a percentage. And they basically told me to buzz off like I'm just a little kid. I came back. I'm like, no, no, really. Like we're doing tens of millions of dollars in sales. I wasn't public yet. It was a couple of years before I went public. You were actually impacting our business. You're actually hurting us. You can't do that. And so they ended up settling. So it worked out okay. But I basically said, whatever you're selling, we want 6 % of gross sales.

1:23:08They're already such an expensive product that we kind of fit into their model. They changed their shirts from like, back then it was$26. They changed it to$29 to basically afford us. And that's all that ended up happening. They were basically saying they were going to sue us. It would take two or three years and they're going to crush us. I said I don't mind spending millions of dollars to fight you because I know how important this is and I don't know if this is going to be a brand for years I knew my brand was around for many years. I didn't know if they were going to keep doing this And if I didn't stop them, they could just keep selling year after year, which could have truly hurt the business And so luckily they ended up settling and it worked out.

1:23:42Okay, and then we lost to the red socks in 2004 Yeah, we weren't their daddies anymore What about the philanthropy part? That's my true obsession so I throw the world's largest toy drive that's happening right this second this is our 12th year I self-fund the whole thing because it's my passion I do one-on-one coaching people wired to charity instead of wired to me so I can get even more capital to put into the toy drives this year we're doing almost a quarter of a million toys we're at 210 ,000 right now three cities to go I fly around like a psychopath to 10 cities in 17 days and I try to find partners or big venues to host these toy drives.

1:24:24And so we got Allen Iverson in Virginia. We did Raider Stadium, Miami Heat Arena. We're getting these big venues to do these toy drives. And my goal is to get other people to host their own toy drives. I don't really post like donate to us or rent. Go buy your own toys. Go give out toys in your own community. You can replicate the same way we're doing it. When I first started, 12 years ago, there were just eight of us on the floor wrapping toys. now we get a thousand two thousand three thousand families per city to come pick up toys and then we donate to the boys and girls club or the city of watts um black sam just did the event we just donated a couple thousand toys to him like i give it to the communities to other people's toy drives so someone's doing it in their community so we'll donate to five or ten toy drives um we're doing for tony tungis the coaches um his charity he's throwing a big toy drive i just find people that They're throwing their own toy drives, and then we'll give it to them to go give out.

1:25:20So boys and girls clubs, churches, other toy drives, or people can come to us in person. I keep doing 10 Cities because I'm obsessed with it. When you see the reaction from these children and also the relief on the parents to get toys that they don't have to buy now, that's why I'm putting in three weeks of my life every year to go out and physically go in person to do these. Love it. I appreciate you. I appreciate you taking your time. a lot of gems, a lot of information. Definitely any last words or your social and any thing that you want to leave the audience with? I mean, the main thing I would say is just get started.

1:25:57You have access to the world now from your cell phone. The platforms are all free and cheap. Social media is free to do. You've got the power of the world on your phone. Creating content is very real. I've watched it change lives. And when you're listening and learning from guys like you, it's just you're getting the fast forward button to success. not just of what to do, but of what not to do. And the things that you can help people avoid, and that's why, again, so passionate about you guys and your brand, is like you're literally changing lives and you don't even realize the mass effect. You might know the stories that are in your head, and you're like, damn, no, I know.

1:26:30You don't realize how big it actually is. Because when you change a household, you change a community. You help someone go make$100 ,000,$200 ,000 a year, it literally changes that ecosystem. It changes whether kids are going to college or not. It changes how they live, how they eat, how they breathe. Do their kids go to school? like the things that happen in those communities. And so to me, investing in knowledge and teaching, like those things that I do and the things that you guys do on a grand scale, that's my passion. Like listening to this will change people's lives. Appreciate it. There you have it, ladies and gentlemen.

1:27:00We'll see you guys next week. Peace. Ernest, what's up? You ever walk into a small business and everything just works? Like the checkout is fast, the receipts are digital, tipping is a breeze, and you're out the door before the line even builds. Odds are they're using Square. We love supporting businesses that run on Square because it just feels seamless, whether it's a local coffee shop, a vendor at a pop-up market, or even one of our merch partners. Square makes it easy for them to take payments, manage inventory, and run their business with confidence, all from one simple system. One of the things we love most is seeing neighborhood businesses level up.

1:27:37There's this West Indian spot right in our community that started with a small takeout counter. Now with Square, they've been able to expand into a full sit-down restaurant and even started catering events across the city. That's the kind of growth that inspires us, and it's powered by Square. Square is built for all types of businesses, from the corner bagel shop that turned into a local chain, to the specialty market with thousands of unique items, to the stylist who's been holding you down for years. If you're a business owner or even just thinking about launching something soon, Square is hands down one of the best tools out there to help you start, run, and grow.

1:28:15It's not just about payments. It's about giving you time back so you can focus on what matters most. Ready to see how Square can transform your business? Visit square.com backslash go backslash E-Y-L to learn more. That's square.com backslash go backslash E-Y-L. Don't wait. Don't hesitate. Let Square handle the back end so you can keep pushing your vision forward. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings.

1:28:52Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. Mind Games, a new podcast exploring NLP, a.k.a. neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release.

1:29:37If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is Dr. Jesse Mills, host of the Mailroom Podcast. Each January, men promise to get stronger, work harder, and fix what's broken. But what if the real work isn't physical at all? I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the valley of despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward.

1:30:14Our two-part conversation is available now. Listen to The Mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows. Hey, it's Joel. And Matt. From HowToMoney. If your New Year's resolution is to finally get your finances in shape, we've got your back. prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Yeah, each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence.

1:30:47Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed human.

From the publisher

In This Earn Your Leisure Interview, We Sit Down With Dan Fleyshman To Break Down One Of The Most Unconventional Business Journeys Ever. From Becoming The Youngest Person In History To Take A Company Public At 23, To Building Multimillion-Dollar Businesses, Dan Shares What It Really Takes To Win Early—and Stay In The Game Long Term. We Dive Deep Into The Real Pros And Cons Of Running A Public Company, How A $2.4 Million Investment Turned Into A Six-Figure-Per-Week Poker Business, And Why Losing $65 Million In A Single Day Ended Up Being The Best Thing That Ever Happened To Him. Dan Also Explains Why Most Companies Fail, The Importance Of Capital Management, And Why Creative Marketing Is The Only Way Startups Can Compete With Conglomerates. Dan Breaks Down His 40/40/20 Investing Strategy, How He Identifies Winning Companies, The Business Model Behind Influencers Making Real Money, And How To Successfully Pitch Brands. This Episode Is A Masterclass On Risk, Branding, Social Media, And Building Sustainable Wealth In A Noisy World. Invest Fest Tickets: investfest.com #EarnYourLeisure #DanFleyshman #Entrepreneurship #Investing #BusinessGame #IPO #PersonalBrand #SocialMediaBusiness #StartupLessons #WealthBuilding #MarketingStrategy

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