Raising Capital, Deal Structure, and Scaling Multi-Million Dollar Companies with Dan Fleyshman – EP 99

Interview with Dan Fleyshman

Raising Capital, Deal Structure, and Scaling Multi-Million Dollar Companies with Dan Fleyshman

Dan Fleyshman is a serial entrepreneur and the youngest founder of a publicly traded company in history.

At 23, after selling $15M worth of clothing in six department store chains and getting a $9.5M licensing deal with STARTER apparel, he went on to scale his “Who’s Your Daddy” energy drink into 55,000 retail stores.

He later launched Victory Poker, which scaled to $65M within 10 months and became a top 5 international poker brand. Unfortunately, poker was banned in the US during that time, and overnight the business imploded. Dan lost everything and was forced to start over from scratch.

While it was a tough blow, he describes it as the best thing that ever happened to him. It led to him building the largest social media influencer agency in the world (Elevator Studio), becoming an angel investor for 37 different companies, starting multiple mastermind groups, and launching an investment fund, as well as an investor syndication group, among many other accomplishments and ventures.

In this episode, we dig into Dan’s entrepreneurial journey and discuss the most significant lessons he learned from building and scaling multi-million dollar companies.

You’ll get to hear his framework for investing in startups, how he attracts investors and funds major deals by structuring unique terms, and the story of starting a modern sports card store during the pandemic that has done $18M in sales in the first year.

Featured on This Episode: Dan Fleyshman

✅ What he does: Dan Fleyshman is the youngest founder of a publicly traded company in history. At the age of 23, after selling 15 million dollars worth of clothing in six department store chains and getting a 9.5 million dollar licensing deal with STARTER apparel, he went on to scale his “Who’s Your Daddy” energy drink into 55,000 retail stores and military bases. He co-founded the “100 Million Mastermind Experience”, spoken at over 200 business events, angel invested in 36 companies, and his agency “Elevator Studio” has spent over $60 million dollars with social media influencers for fashion brands, film studios, mobile apps & consumer products.  In 2010 he launched Victory Poker and built the third largest team of professional players out of the 550 poker sites on the market. Dan is also a passionate philanthropist and created his charity, www.modelcitizenfund.org, which creates backpacks filled with over 150 emergency supply items for the homeless.

💬 Words of wisdom: I have a quarterback for every company, for every investment, and for every event. And so, if you see me throwing a charity event, a business event, a mastermind or anything in between, there’s someone specifically running that thing. If you see me investing in a new company, a new project, a new deal, there’s a quarterback running that specific thing. I don’t do anything unless I have a quarterback for it, because otherwise, I just physically can’t.” – Dan Fleyshman

🔎 Where to find Dan Fleyshman: LinkedIn | Instagram | YouTube | TikTok

Key Takeaways with Dan Fleyshman

  • Placing “quarterbacks” in your businesses so you can accomplish more without sacrificing your time.
  • How Dan scaled a $15M clothing brand and took his energy drink public by age 23, becoming the youngest founder of a publicly traded company.
  • How his $65M online poker company failed overnight, and why it was the best thing that ever happened to him.
  • What it was like for Dan to get a $9.5M licensing deal with STARTER apparel.
  • Becoming the largest social media influencer agency in the world (Elevator Studio), and how Dan leverages this business to make equity deals with his clients.
  • Dan explains how he uses a “rolling fund” to raise capital. This is a fascinating disruption to the traditional fund model that allows accredited investors to commit with a lot less risk.
  • Learn about Dan’s investor syndication group (now 800+ members) and the criteria he uses to de-risk deals and invest in companies with big potential, including Sneaker Con, which was recently acquired by eBay.
  • Partnering with the world-famous DJ Steve Aoki and DJ Skee to open Cards & Coffee, a modern sports card store that did $18M in sales in the first year.
  • Raising capital using the “7, 8, 9 deal structure” and how Dan used this model to attract investors (including myself) and finance Black Site Ranch—an $8M commercial property with a ton of utility and perks!
  • Learn about Dan’s 100 Million Dollar Mastermind Experience AND the Avengers Real Estate Mastermind.

Dan Fleyshman on Turning Passion into Incredible Success with Cards & Coffee

Dan Fleyshman Tweetables

“So, for me, taking equity in companies is way better because if I get 1% here, 5% there, 10% or 20% of a smaller business, or 50% of a brand new start-up, I have a real shot at glory.” - Dan Fleyshman Click To Tweet “I’m never planning on selling Elevator Studio. It’s just not going to happen. Even if you offer me 2x or 3x, I’m not going to sell it because it's who I am, it’s my business, it’s my passion.” - Dan Fleyshman Click To Tweet


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Read the Full Transcript with Dan Fleyshman

Justin Donald: All right, Dan, I’m so excited to have you on the show. Welcome.


Dan Fleyshman: Thanks for having me.


Justin Donald: Well, we talked about having you on a little while ago, and I’m glad that it all worked out. Summers are always kind of tough. And for those listening, this is not going to come out in the summer, but we’re recording it in the summer. You’ve had a lot going on in your world, so welcome.


Dan Fleyshman: Yeah, there’s definitely a lot going on.


Justin Donald: Yeah. So, I am curious how a guy like you can juggle so many things. I feel like people say to me all the time, how do you get so much done? And then I look at someone like you and I’m like, how do you get so much done?


Dan Fleyshman: I have a quarterback for every company, for every investment, and for every event. And so, if you see me throwing a charity event or a business event or a mastermind or a free event or anything between, there’s someone specifically running that thing. You see me investing into a new company, a new project, a new deal, there’s a quarterback running that specific thing. I don’t do anything unless I have a quarterback for it, because otherwise, I just physically can’t.


Justin Donald: Well, that’s good business practice from the standpoint of scaling and keeping you in your zone of genius, which is great. I’d love to hear some of the early years for you. How did you become the entrepreneur that you are today? Did you always know you were going to be an entrepreneur? Or did that come later in life? Like, how did you figure that out?


Dan Fleyshman: It all started early, so it’s kind of like, if I throw you in the pool, you’ve got to swim or you’re going to die. I was working three jobs in high school simultaneously to save up money because we just don’t have any money. And so, I saved up $43,000 to go to college, but instead, I started my company. I trademarked the catchphrase, “Who’s your daddy?” for over 300 products, at that time, mostly clothing and accessories.


Eighteen years old, we did our first million in sales. Nineteen years old, we did $9.5 million in sales. And then when we went public, we were 23 years old to launch energy drink. From 23 to 27, I literally don’t remember. All I did was sell, sell, sell, sell, sell. While we were public, I got us into 55,000 retail stores, just all of this cranberry, pineapple, and green tea energy drink. And we did the very first, like zero-sugar, zero-carb, zero-calorie energy drink.


So, things went great. On the 10-year anniversary, I resigned from the company when I was 27, starting when I was 17. And I want another feather in my cap. So, I started an online poker site with Dan Bilzerian, DJ Steve Aoki, Playboy playmates, and like the cool kid’s poker site.


Within 10 months, we’re the top five poker site in the world. And then online poker gets shut down in America. So, there was a $65 million company overnight. I only had five employees. That’s a very low overhead, but I got started from scratch. I can’t sit on the floor and cry about it.


And so, that terrible business moment actually became the best thing that ever happened to me for the future and for a lot of other people because I started my social media agency, which is the largest social media agency on the planet. I’ve done 110,000 paid posts just in the last year. I started my charity. I started angel investing. I angel invest in 37 companies now.


So, losing that company ended up changing everything in my world of not ever having to have all my eggs in one basket ever again. And that’s my focus now. I’m angel investing. I’m throwing events, doing charity stuff. So, it all started from that.


Justin Donald: Well, that’s interesting, Dan, because I feel like you went from the highest highs to the lowest lows. So, you are the youngest founder of a publicly traded company in history, which is quite the accomplishment at 23. By the way, I was causing trouble trying to figure out my life at 23, you had a company that went public at 23. That’s just unbelievable.


And it sounds like you rolled the profits from that exit with that company into the online poker business where you had, like you said, all your eggs in one basket, and then that shut down overnight because there are just some things we cannot control. And this is a great case study for the value of diversification, right?


Dan Fleyshman: Yeah, for sure.


Justin Donald: So, what was it like at the highest of highs? And what was it like at the lowest of lows?


Dan Fleyshman: So, at the highest of highs, you don’t actually feel much different. You’re still in the zone. That’s why I said I don’t remember anything from 23 to 27. We’re publicly traded. I’m on CNN and Fox. Social media is not really a thing back then. This is, remember, 2005 to 2009. I got MySpace, right? But I’m in it. I’m in the zone like the money difference didn’t change anything to me. I didn’t buy stuff. I was just in it.


On the poker site, I was so much fun because now, social media just getting started, 2009, 2010, 2011. Social media is going crazy. I’m surrounded by people that have huge social media followings. We’re on TV every day, and then everything crashes.


And so, when you’re in it, I don’t necessarily know that you feel that you’re like in it. You’re just kind of you’re working, you’re feeling it, you’re growing, you’re scaling. But when it crashes, things get real quiet because you stop getting on the phone calls and texts, you stop having everyone invite you everywhere, you stop hanging out with everyone because it’s over. The party stopped, the music stopped.


And so, that was an interesting moment in my life. But I always say, don’t sit on the floor and cry about it. I should have. Just lost a $65 million company. There’s justification to cry, to be sad and sit there.


Justin Donald: Totally.


Dan Fleyshman: But instead, I went the opposite way and I went hyper-focused on working again. I proactively called every media outlet. I did like 80 interviews in a week. Like I did everything from ESPN to the local guy that has 14 followers. I didn’t care. I wanted everyone to hear what just happened because we were the only poker site that paid every single person back within four days. Other people took them years. Some of them never got paid back. And I was so proactive to pay everyone back that I wanted to get this story out there because I wanted the other sites to do the similar thing.


And so, in that moment, I’m losing everything and the lowest of lows. You have to think about what are you going to do with your life because normally, you’d wake up the next morning, you go back to work, but instead, work is not there. And so, in that moment, I just put on my hat and said, you know what? I’m going to do these interviews. I’m going to start consulting, start my social media agency. I’m just going to get back onto the horse and go full steam ahead.


Justin Donald: Well, I love it because your business implodes. And I feel like most people would say, oh, my goodness, my livelihood is over. I need to hold on to everything that I’ve got here versus you’re actually paying everyone out, make sure they get their money back, which you have. I mean, depending on where you’re located, where that business is domiciled, depending on different things, that may not be something that you have to do. I think it’s the right thing to do. And I know a lot of companies did not do it.


So, I think it’s great that you did and that you kind of created a marketing campaign around like, hey, do right by people here. And even though it’s the right thing, I’m sure and I know you did it because it was right. I’m sure that probably, long term, that benefited you with some of those relationships, too, right?


Dan Fleyshman: Yeah. I wanted to be able to sleep at night and I wanted to be able to walk through a casino, not worry if some poker player was mad at me because they lost 40 bucks or 400 bucks or $4,000 or $40,000. And so, that was a big deal for me, is that it wasn’t a decision. Like other sites had a decision, other of them even just like waited a year or two and made interest on the money because when you’ve got hundreds of dollars, making a couple of percent interests is a lot. And so, some of them just took their sweet time to pay people back. Other sides literally just couldn’t or didn’t. And they use that player’s money for their own overhead or to keep for themselves and disappear.


I was based in Malta. I’d kind of done bad things. Didn’t even cross my mind for one second because, one, I know I’m going to get back on the saddle. So, paying back these 41,000 players was the only choice for me. Two, I’m in this for the long run. I want to be able to do things in the future. And some of these guys that didn’t do that, when they walk into a casino, people are literally throwing eggs at them. Like, that’s an actual story. Like, people are throwing tomatoes, and then people are throwing sandwiches at them. Like they try to walk into the World Series of Poker, it’s not good.


And so, I don’t want to say I foresaw that, I just foresaw the fact that, one, I want to make sure everyone gets paid back because I want other sites to pay people back. And two, business is a long-term game, it’s all about your name. And the best thing that I did was pay everyone back really quickly because in the poker world, everyone still remembers that a decade later.


Justin Donald: That’s cool. And by the way, you are a poker player. You have won many tournaments yourself. You are an avid player, right? You still play?


Dan Fleyshman: Yeah. I played till 4 a.m. last night.


Justin Donald: Wow. So, where do you play these days or these local card games? Do you go to the casinos? A little bit of both?


Dan Fleyshman: A little bit of both.


Justin Donald: Yeah, that’s fun. Now, something I wanted to bring up. I thought this was really cool. With your company that you took public, you had a licensing agreement with Starter apparel, right? There’s a big licensing agreement, I think almost a $10 million licensing agreement. And what’s so cool about that is as a kid, I remember buying Starter hats. The only hats I would buy were Starter hats. And I had a collection of them, I would go, and I mean, I just loved these Starter hats. Nothing fit me the same way. Nothing looked as nice. They were just kind of in a league of their own.


Dan Fleyshman: Yeah, Starter was a great company for us. So, they paid $9.5 million over three years just for the UK.


Justin Donald: Wow.


Dan Fleyshman: And the best part about the deal was, besides the money, it helped us because there were quarterly royalties. We got to use full rights for whatever they designed. And so, they were making jeans and shoes and all these things that I could never make. That was like, you needed guys who are getting a quarter-million-a-year salary to design shoes. Those are like, super high-level shoes are really hard. So, I got to utilize their shoes and their jeans and their shorts and their jackets, things I never would have made that saved me so much money, but also gave me so much expertise because it’s coming from the Starter apparel executive that had been there for 14 years is now, not working for me, but kind of working for me because I’m getting to use all their designs.


Justin Donald: That’s cool. Yeah, that’s a neat experience, and having that international bend to what you were able to figure out in your younger years, I mean, you’re well-traveled. So, it’s cool that you have been able to experience business on an international level, right? There are so many positives to that.


And then, as an influencer and having the agency of the most influencers, you’re going to have them all across the globe. So, I think, it’s just good to have that international focus. So, give me an idea, like, why do people search out your agency to partner with and to work with? What is your differentiating factor? You said you’re the largest, but why? What is it that makes you guys so great?


Dan Fleyshman: Sure. So, we’re not largest by staff. There are a lot of companies that are much larger. We’re largest by execution and amount of influencers. So, we W-9 over 3,500 influencers in the last year. There are lots of agencies that say, oh, we’ve got over 100,000 influencers. Well, they’re on an app that you don’t have their phone number, you don’t know them.


I physically have the W-9, like they filled out forms and they have their driver’s license. Like I’ve paid them their bank accounts, like 3,500 influencers of all sizes from the Kardashians to the local fitness and beauty influencer. And so, from a brand perspective, knowing that we’ve done eight years of some of the biggest campaigns, some of the most prolific brands, we’re the only agency of record for Oracle, BET Television. These are humongous corporations.


And to trust us for years, it’s not a one year, I’ve been with them for three, four, or five years each. It’s why people come to us. I don’t solicit clients because I don’t really take on too much clients. The last couple of years, we’ve said no to most clients unless they’re medium to large brands, specifically large brands.


And I recommend to other people, hey, use this agency or use that agency. I’ll send off referrals all the time to other agencies that are small, medium, and large, simply because our agency is really focused on mass branding scale. And so, it’s mostly from referrals. It’s because when I’m out there on stages or speaking or even here on the podcast, I’m not saying, hey, come work with Elevator Studio. I’m not looking for clients. It’s really meant for brands that fit us or that I can invest into or take equity in or trade for more than getting a client that spends a couple hundred thousand or a couple million.


Justin Donald: Yeah. And so, to take that step further, you have advised companies, you invest in companies. A lot of these probably came originally from this network, your influencers. You’re getting deal flow, but you’ve got your own company called Elevator Studio. I’d love to hear you kind of share some thoughts about that.


Dan Fleyshman: Yep. So, the agency is interesting. So, we make money from people spending budgets, right? Say, here’s 25 grand, 100 grand, a million, whatever the budget is, and we make 20% of the ad spend. So, that’s the basic cash of the business, how it works. So, you can do the math that we’ve spent 60 million bucks, you can do the math on the 20%.


What’s more interesting and more important is that we’ll take equity in certain projects as trade, or we’ll invest to buy extra equity into a brand that we know is working. So, let’s say someone spending 100k a month with us and they increase to 200k, well, we know that it’s working, we know that it’s growing, and we know we’re helping with that business. When I go to them say, hey, let us invest 500k or a million bucks, or instead of paying us 200k in the next three months, we’ll do it for free, and trade us $600,000 in equity. We’ll do different types of unique deals like that because the equity is the real play.


Agencies on average only sell at a 1x multiple. And so, I’m never planning on selling Elevator Studio. It’s just not going to happen. Even if you offer me 2x or 3x, I’m not going to sell it because it’s who I am, it’s my business, it’s my passion. And I have Elevator Nights, Elevator Syndicate, Elevator Rolling Fund, Elevator is who I am, it’s my whole world. And so, I’m not going to sell it, but I’m also not going to get a good multiple if I wanted to sell it.


So, for me, taking equity in companies is way better because if I get 1% here, 5% here, 10% or 20% of a smaller business, or 50% of like a pure brand new startup, I have a real shot at glory. And I can help with the success to make sure that it works out more often than not, simply because it’s part of our world.


Justin Donald: Yeah, that’s one of the things I love to do when I invest in a company is if they can give me influence control, just having some expertise in a certain space, it de-risks the deal because I know how to help move them along. I know how to connect them. I know how to help them scale in certain niches or in certain genres. And so, I feel like you have that going for you where it’s like, well, hey, this company, we’re just going to have them pay us. We’re not going to do any sort of engagement of equity or whatever.


But this one over here, they’re doing stuff. I have the social clout or the experiential know-how where I can protect my investment. And in your case, sometimes, it’s a trade, but sometimes you’re putting your own cash into it if you want to double up. And it’s nice to have the ability is the one plus one equals three type of experience, right?


Dan Fleyshman: I’ll only invest into a company that I can help.


Justin Donald: Yeah, that’s good.


Dan Fleyshman: I don’t take on deals that I can’t help, even if it’s like really good money. Like, this company is in the medical field and they’re doing the heart, blah, blah, blah, I can’t help your heart surgery company. If you’re making T-shirts that have hearts on them, I mean, they can sell lots of T-shirts with hearts on them, but God bless you if you’re doing heart surgeries, thank you for your service, but I can’t help you and I really want to invest. It doesn’t matter how good the deal is, I can’t help you.


Justin Donald: Yeah, so Elevator’s kind of like the parent company, and then it’s broken down into these different other companies. So, you’ve got Elevator Studios. You’ve done these events called Elevator Nights, which are big events that you host for entrepreneurs. You’ve got your Elevator Rolling Fund, which is just deals that you’re kind of scooping up based on the fund that you’ve created. And then you’ve got your one-offs, which would be your Elevator Syndicates. So, instead of investing in a fund with multiple companies, you’re investing in a single deal through a syndication that you’re putting together via AngelList, right?


Dan Fleyshman: Yep.


Justin Donald: And so, why have you, I guess, gone the route of doing all the syndicates, doing the fund? Why AngelList? I’d love to hear your thought process because you and I, we’ve kind of worked on a handful of things here together and we’ve looked at some deals that each other are doing and we’ve kind of walked through. You showed me kind of the platform and the way that you built things out on AngelList, which I thought was brilliant. So, I’d love for you to share with my audience just some of why you’re moving in this direction.


Dan Fleyshman: So, I did 37 angel Investments personally, and 11 of them through Elevator Studio, and I didn’t reach out to friends very often. So, for the most part, I did a syndicator and bring in friends to the deals. Towards the last, like number 34, 35, 36, 37, friends kept wanting to jump in because they keep seeing me post about this brand and that brand, this business and that chain and this, etc. And so, I was syndicating kind of, where it was more like I would get, Justin, an area like, hey, I want you guys invest in this thing and I’ll introduce you directly to the founder. Wasn’t exactly syndication, it was like some friends of mine would invest directly into the companies knowing that I was investing.


I then talked to AngelList about the Rolling Fund because I’ve always wanted to have a hedge fund. Everybody always told me I should have a hedge fund, except they’re hard. It takes one or two years to put together a legal paperwork wise and to do like a full what’s called a roadshow where you go pitch all the investors all over the country or international.


And then once they commit to you, let’s say you’re raising a $50 million fund and Justin says, I’ll put in $5 million. Erick’s like, I’ll put in $2 million. I then have to go back to you and circle back in a year from now and say, okay, now, I’m ready to take the money. So, it’s almost two roadshows, two pitches, not really the thing I wanted to do, but with a Rolling Fund, it allows me and allows investors to invest quarterly, a smaller amount of money, and they can raise it or lower it at any time after the first year.


So, let’s say Justin’s like, you know what, I’ll throw in 200k into your fund, Elevator Rolling Fund. He’s just going to send $50,000 a quarter, and then in a year or two from that, he was like, you know what? Let’s increase to the 200k a quarter. And he’s like, you know what? I’m going to buy a house. Let’s go down to 50k a quarter again, like he can adjust it.


With a hedge fund, if he says 5 million bucks, that’s 5 million bucks, and he’s got to wire me 5 million bucks. It’s a big difference and a different type of commitment. And so, the Elevator Rolling Fund was a good fit for me and my style. And it’s good for anyone out there that’s an entrepreneur that knows how to raise capital. It’s really meant for a solo entrepreneur.


So, let’s say, Justin wants to go raise 1 or 2 million bucks. He doesn’t have to. He can raise 25k, 50k, 100k, 300k, 200k at a time, any time throughout the year, and it just kind of rolling. That’s why it’s called the Rolling Fund. So, I like that a lot and that made it easy for me to be able to invest in deals. We’ve done over a dozen investments there.


And then the Elevator Syndicate is the syndicate deals. That’s also done through AngelList. I use AngelList because they’re the biggest multibillion-dollar company. They’re fast, they’re fission. They take care of legal and accounting and K ones and wire transfers and documents. They’re fantastic. And so, the syndicate is now, I can go out to my friends and say, hey, I’m investing into this water company or this restaurant, etc., would you like to invest? Yes or no?


I have 846 members of my syndicate now, and so, I can now text them and email them, like, hey, do you want to invest in this beverage? They can throw in 25k, 50k, 100k. If they say yes, they’re going to get wire info. If they say no or say nothing, they don’t hear from me again about that deal.


And so, I made it frictionless. Let’s say I text Justin about four deals, he doesn’t respond once, no problem. Deal number five, he wants to throw in 100k, great. I’ll send you the wire info. Literally, that simple. And so, the whole passion for me is we are now investing $3 to $6 million a month in the deals. We’ve done $36 million total just this year. Funding comes within two weeks. Where it only takes an entrepreneur 6 to 12 months, we’re now funding a company in a couple of weeks.


And so, emotionally, I like it because it’s fast and effective. It’s easy for my friends to invest and my followers to invest and my syndicate members to invest. And from an entrepreneur’s perspective, they can get money in a couple of weeks instead of taking 6 to 12 months.


Justin Donald: Yeah, that’s a huge value add to the entrepreneurs, to the business that typically needs money ASAP. Hopefully, the businesses are at a point where they are kind of forecasting, hey, our burn is high enough that we’ve got X amount of months or we’re running out here and five months, six months, 12 months, and that you can proactively do it. But the nature of entrepreneurs is they often don’t have that in place. They don’t have a CFO, they don’t know that’s happening, and they need money ASAP. And so, that’s great.


So, what type of track record, I know it’s hard if you have just invested this year, I mean, these are generally going to be longer deals. If you had any gone full cycle yet, if not or any close, I’m curious what that looks like because on the angel investment side of things, you’ve got the highest return profile, but you also have the highest risk profile. So, I’d love to hear some of your thoughts on how you (a) kind of de-risk a deal, (b) how you use your expertise and superpowers to find deals that are better for you and your community, ones that you can help, and then (c) obviously, have any gone full circle yet?


Dan Fleyshman: Yep. So, the main ways we de-risk is we only invest in companies that are already doing $2 to $20 million sales. And so, the 2 millions are low mark because that one business is kind of like figured it out. They got through the system, the processes. We know that enough people care to spend a couple of million bucks with them. So, it de-risked us a lot compared to a pure startup. It’s just a great idea or great founders or great celebrity or influencer running the business. It’s way different no matter how famous they are on $0 in sales versus $2 million in sales. It’s two different worlds.


And so, we de-risk a lot by that. We de-risk it because we’re bringing in front of strategic investors a bunch of Justins to come in to invest to help the business. And so, yeah, we’ve had some full circle. One is called Sneakercon, Sneakercon is a traveling festival. It gets 12,000 to 18,000 people per event. There is a really small company called eBay, just acquired it in December, which was great, and that was like…


Justin Donald: It’s awesome.


Dan Fleyshman: That was a quick turnaround because the business had already been around for nine years when I came in. But then, because I came in so late, a year later, boom, eBay comes and acquires one side of the business. Then sold a company called Dollar Beard Club. It’s a monthly box for beards. That was also in December, actually in the same week.


And then Everbowl just had a big financial transaction a few weeks ago. So, I helped raise $5 million plus I invested on top of it, plus I bought a chunk of 23 stores. And then Drew Brees threw in $2 million and then he bought 85 stores and a lot of stuff packed with Everbowls and acai bowl chain. But then just recently just took in an eight-figure round and is really going for it now. We’ll be announcing it shortly, but it’s all happened now officially. And so, there’s been some cool ones like that. And then within the Rolling Fund, our very first investment just got this next round at 700% higher valuation.


Justin Donald: Wow.


Dan Fleyshman: A much bigger round two. And so, that’s an education company that they set up the education for Elon Musk for his kids. And so, they use that exact same profile for Elon that they did for his kids to teach children more interesting art design, science-type learning from home. That company now just got 700% higher evaluation, big financing round. Anthony Pompliano @pomp is the one that helped lead that whole round and brought me in, and it’s just been great to see.


Justin Donald: Oh, it’s awesome. Well, it’s neat that you’re getting so many exits. Obviously, your criteria helps where you’re $2 to $20 million so that they’re more proven. They’re not trying to prove market fit. If they fit, it works. But a lot of the time in angel deals, you don’t know if you did well or didn’t do well. You’re crossing your fingers. I mean, you may not know anything for 10, 15, 20 years. You may not even know that you lost money for 20 years, right? So, it’s cool when you have criteria, and I talk all the time about having investor criteria and I think when you have that, it just makes you smarter and then you’re less impulsive, less emotionally making decisions versus logically from a good point in time when you laid out exactly what it was that you needed to see before you could invest.


Dan Fleyshman: Yeah.


Justin Donald: So, something else that I thought was really cool that you’re doing is these stores that you’re opening. You got an online store for cards, collectible cards. And I’m not sure if it’s just cards, if there’s memorabilia, but I think you just opened your fourth location and you’ve got your online location. I’d love to hear more about that because this one’s taken off for you.


Dan Fleyshman: Yep. So, this was fun. So, Gary Vaynerchuk, GaryVee is the one that named it. It’s called Cards and Coffee. And it was just in a group chat where we’re talking about sports cards with a bunch of people. Gary and I started a couple of years ago, and he’s like, you know what? Someone should start like the Apple of sports cards, like the Netflix of sports cards, like super cool modern because most sports card stores are old school like 20, 30 years old style.


And it was middle in COVID. My office is closed. My employees are all working remote. I was like, I’ll do it, and everybody was like, yeah, yeah, Dan, I’ll do it. And that’s it. It’s kind of like when you’re with your buddies at the bar, like having a beer is like, you know what? One day, we show up in a sports card store, and then nothing ever happens. You’re sitting with the same buddies six years later saying one day, we should open a sports card store.


Well, I was born, I did it. And so, I opened up here in Hollywood Boulevard with DJ Steve Aoki and DJ Skee as my co-founders. So, I put up the money. I started with $1.6 million, just self-financed, and said, you know what? I’m going open a sports card store in October 2020 when LA’s shut down. So, we end up doing a million bucks in the first eight, nine weeks. I’m like, okay, this is working. People like it. This is fun.


And we started doing a million a month and we started doing $1.4 million a month. I was like, wait a minute, this is interesting. And we opened up a store in Salt Lake City. Then on month eight, we’re at $10 million in sales. I say, okay, well, now, this isn’t a hobby or fun little project just to make Gary proud of me. Like right now, this is something that’s like, we’re going for it.


So, I do a small round, I raise $4 million, but I do a 100k cap. So, no one, no matter how rich they are, can put in more than 100k, except for Ed Mylett, because it’s Ed Mylett. But everybody else and there’s a lot of billionaires in there, I only let do 100k each. And I wanted strategic investors involved in this business and it wasn’t about the $4 million, it was about the people.


So, I was like the owner of Forever 21 and the guy that owned 6 million square feet in New York and sports team owners and executives and post Malone’s management, like all these interesting characters were the investors. And then that’s when it became scale time. And so, our first year, we did 89 sales. Now, I just acquired a company called Rizzo Sports who had done millions and millions of dollars in sales. And they have their own multiple stores, but they also have online operations, like we do. Great brand, been in the game for decades. So, I bought a big chunk of them.


And so, now, we just opened our sixth store and I literally like, right before I go on this podcast, was working on a lease for our seventh store, and then I’m going in for eight and nine, so I’m trying to get to nine this year, and then next year, who knows what will happen, how many we’ll get? My goal is to have nine this year. I want to add Calabasas. I want to add Boca Raton. And I am adding Dubai in December.


And so, it’s sports cards and Pokemon. It’s football, baseball, basketball, wrestling, F1, UFC, Pokemon, Magic: The Gathering. So, we’re the first true national chain store. So, we’re at six now, but I’ll feel better saying national chain once we get to over 10 locations.


And then, we’re the only true 24-hour-a-day live operation. It’s called Live Breaking. So, it’s like QVC but for cards. So, that’s on TheCoffeeBreakers.com or Instagram is thecoffeebreakers. And you can see 24 hours a day, you want to buy football, baseball, basketball, wrestling, whatever, we’re selling it.


And that becomes twofold. One, retail chain, so people feel comfortable that we’re a big chain, that they can come see us in person. Two, we’re on 24 hours a day where most people are working out of their apartment for four or five hours or live from retail stores 24 hours a day. And that to me is my true passion project. So, for the most part, I only invest in the companies. I don’t start anything new. This one I started as my baby. It’s my passion.


Justin Donald: That’s awesome. And by the way, you had a passion in collecting baseball cards and different types of sports cards, right?


Dan Fleyshman: Yes.


Justin Donald: Yeah, that’s cool. So, what type of a collection do you have today? Not your store, you personally?


Dan Fleyshman: I don’t have a single card anymore. I put every single thing into the store because I know myself, like I can’t buy one Kobe Bryant card, I want to buy 30 of them. I can’t buy one Michael Jordan, I want them all. So, what I did was I swore to myself that I wouldn’t buy any cards for myself until after the exit. And also, it removes any wonder of, like, Dan, why did you buy that card for yourself, not for the store?


Justin Donald: That’s good.


Dan Fleyshman: I didn’t have investors to begin with, but once I had investors that made even more sense, like, why did Dan buy that collection personally or buy that famous card personally when he could have bought it for the store? That doesn’t happen with me. It’s not an option. I don’t have a 10-cent card, let alone to know a $10 million card.


Justin Donald: Yeah, that’s cool. Well, I’m excited about that. It’s interesting, as a kid, I collected all kinds of stuff, and one of my favorites was actually the Marvel comic cards. I just love those. I never got into comics, but I got into the comic cards because one of my buddies when I was young, when I was in elementary school, had them, was collecting. And so, I actually have a pretty big collection of that still and, of course, my baseball, basketball, football cards. So, yeah, that’s awesome. I love that.


And I love just fresh ideas going in a path. I don’t think anyone before you did this would say, yeah, that’s a great business. We should start a national chain for sports cards. That’s the beauty of it. When you have this idea and it lands, it’s just incredible. So, long term, do you think this is something where most major cities are going to have one? Or is the goal not full scale?


Dan Fleyshman: So, there are a few hundred stores that are out there in the mainstream cities, but they’re mostly old-school stores. So, I don’t think I’ll be in every city simply because of staffing. This is not like my acai bowl chain where I can hire high school and college kids. It doesn’t take a rocket science to make an acai bowl. It just takes a smile and you have to have fun with it.


In sports cards, you got to know a lot, a lot, a lot. And so, I’m only opening and sitting as if I have a quarterback or someone that can run that operation for me and I got to trust them and then got $500,000, a million bucks, two million bucks with the cardboard in glass cases. So, I have to be able to trust them to manage the operation, trust them to want to work morning, noon, and night. It’s not a six-hours-a-day-type business. This is a morning, noon, and night-type operation because there are thousands of cards coming in and out of the store and they’ve got to really know their stuff.


And so, I’m only opening in cities that I know people can be there to operate it, so I don’t know how many stores we’ll end up with. My guess realistically is in the 10 to 20 range of enough people that I know that are really good and I trust. And then, I might acquire some other stores like I acquired the two in Riverside because that’s a great operator. I trust Rizzo Sports. They’ve been around for years and years. That’s a great business, but there’s not that many of them out there for me to go acquire.


So, I don’t know how many I’ll have. I do know that a lot of people are copying me, which is fantastic, which I want, by the way, I’m not saying it like an egotistic way. They’re making good versions of stores all over the place. Even right next to me in Los Angeles, there are multiple stores that just popped up in the last few months. And so, I like the fact that the business is coming out there and I want people to go out and replicate because this is a fun industry.


Justin Donald: Yeah, that’s awesome. Well, I’m excited about that. You did a deal recently that I got involved in that I’m really excited about. And it was the Black Site Ranch that you bought. I’d love to have you share a little bit about this and even about some of the terms of the deal because I love when you can invest in a deal where, as the investor, you get utility from that investment. And so, this was kind of a no-brainer for me, but I’d love to hear you share this with my audience.


Dan Fleyshman: So, last year I did an event called Operation: Black Site with a guy named Bedros Keuilian. Bedros owns hundreds and hundreds of gyms called Fit Body Boot Camps, and he does these events, one called The Project, where it’s like really intense for 75 hours of military training like Navy SEAL trainee and does one for kids called The Squire Program. So, it’s like high school kids with their parents that go through a one-day version of this.


And so, I was like, you know what, I want to do Operation: Black Site. I’m going to bring in UFC champions like Michael Chandler and Tim Kennedy, and then the guy, Robert O’Neill, who shot Bin Laden in the face. That guy is going to come out here and teach us and train us. I’m going to bring in FBI experts, and we’re going to do fight training, military training, shooting training, and mental training for three days. So, that was Operation: Black Site. Boom. We did our event. That was super fun.


Then, at the same time, I’ve been wanting to get a ranch. My wife’s obsessed with animals and saving the animals. And so, it has been my passion project, so trying to find a ranch, but it’s been almost two years trying to find a ranch. And a couple of them fell out of escrow because the buyers changed their mind. They wanted to raise the price at the last minute, went through a lot of interesting things in this real estate market where I had it locked in for $4 million and they wanted 4.6, like the week of closing.


And another one for 5.7, they wanted 6.2 in literally the last three days of closing when it was already done. And so, I kept searching and searching and I finally found like the one. Actually, the very first one I ever wanted is the one that we got.


And so, the concept was I was going to raise capital to help improve on this property. So, the ranch, obviously, I’m going to live there my life and have animals there, but with Bedros, we’re going to build Operation: Black Site on the ranch, so Black Site Ranch. And you can come there and get military training for a couple of days straight. And there are also Airbnbs on property, and it’s near Pechanga Casino so lots of people could stay at the casino because it’s a billion-dollar casino down the street.


Justin Donald: So, you’re in Temecula, California, which is also a nice location, the wine country out there.


Dan Fleyshman: Yep.


Justin Donald: And this ranch is massive because you can have all these different operations going on in the same land, just four massive different events that could be had at the same time, right?


Dan Fleyshman: Yep. So, we’re going to build a thousand-person mega barn so we can host large-scale events, business events, entrepreneur events, comedy shows, etc. We’re building a 300-person wedding venue. There’s already a flat space there overlooking all of Temecula for outdoor venue plus indoor rent on the same plot of land up there, going to build an American Ninja Warrior course.


Justin Donald: That’s cool.


Dan Fleyshman: That’d be so fun. Military obstacle course, a football field, a basketball court, racquetball, pickleball, all the different sports you can do. So, it’s a fun place to be. Plus, there are a bunch of animals there. The most famous influencer for animal space, his name is the real Tarzan. He’s got hundreds of millions of views about his animal rescues and his passion. He’s actually moving there to help set up shop.


Justin Donald: Wow.


Dan Fleyshman: To build up the whole animal experience. So, you got a guy with 6.6 million followers who are going live on property to help me set up what’s called the Wyld Jungle, W-Y-L-D. So, why do we raise capital and how do we do it? So, I wanted to raise capital because this is something that I’m going to be doing forever. I wanted to really fast forward how much I’m building on this space, and although I could still finance it, I’m normally and typically an investor into private equity deals and projects.


And so, I want to keep a lot of my capital to keep investing into those type of deals. I’m still spending millions of dollars on the property, but I wasn’t going to go spend $8 million on the property person, right? So, we did a financing round for $8 million paying 9% interest per year, but we gave people three different options.


So, we call it a 7, 8, 9. And the guy name Kent Clothier is the one that kind of popularized it. He raised $40 million between two funds on the same exact structure with the same exact paperwork. So, 7, 8, 9 means you can choose. And as an investor, let’s say, it’s Justin, I want to invest for one year and make 7% for that year or Justin can say, I want to do it for two years and make 8% a year for two years, or I’ll lock in for all three years and make 9% a year for all three years.


At the end of that term, whether it’s one-year or two-year or three-year, Justin is going to get a balloon payment on his entire initial investment that he made monthly interest. He was receiving monthly interest the entire time. So, let’s say he did, let’s just use $100,000. He’s making $9,000 a year for three years, but he’s getting them $800 a month checks every single month for the whole three years. So, he’s getting that $9,000 a year, makes a little more than $27,000 because it compounds a bit, and then boom, gets his entire $100,000 back at the end of the term.


The perks on top of that is now, Justin can not only go himself to the ranch and experience that whenever he wants to, he can send family, he can send friends. If he needs to send employees there for a retreat, he wants to rent out the barn to throw an event, he’s now going to get those fees waived. And so, we’re normally charging for this venue or that experience or this thing or that thing, Justin doesn’t pay that. And so, he’s making interest on his money, has access to this really cool ranch, not just for himself, but now he can utilize it for his friends, family, and staff.


Justin Donald: Yeah, that’s awesome. And I just love that perk. By the way, we’ve got to be careful because you just told all my friends who may be listening that they have a chance to be able to go here. But in all seriousness, I’m excited to send people there. The property is gorgeous. I’m excited to go experience it with my family and I think it would be cool to do some of these trainings, and more over than anything, to have utility of the property into perpetuity. That’s incredible. So, I love it. That, to me, is more important than the return itself. Though I don’t want to lose money and I like getting a return, I love when I can actually gain more than just the monetary reward of an investment.


Dan Fleyshman: Absolutely.


Justin Donald: Yeah, that’s cool. So, you’ve got a couple of masterminds. It’s funny, sometimes people will say to me, hey, you’ve got a very high ticket, high priced mastermind. And I say, yeah, it’s to attract a certain person. And when they’re a right fit, then they’ll generally kind of just fall into place. And if they’re not, they’ll kind of weed themselves out. They’re not ready yet.


And so, it’s funny because your mastermind, your flagship mastermind, the 100 Million Mastermind, is $100,000 a year. So, I’d love to hear, you just kind of share some thoughts on that mastermind. I met you through my friend Eric Van Horn. That’s how we originally connected, who is part of that mastermind, along with several of my friends. I probably have like 20 friends that have been part of it.


I know you cap how many are in it, and then you’ve got your lower ticket one, which is the Avengers. We do a lot of these, I guess, the deals that you talked about earlier with some of the AngelList deals, some real estate, some different things. I know you’re looking to open that up to different things. But talk about the 100 Million Mastermind because I know that’s kind of experiential.


Dan Fleyshman: Yep. So, the concept was I was speaking a lot of other masterminds and I was watching people liked and didn’t like what they cared about, what they didn’t care about so much. And I wanted to make the most high-end mastermind in the planet. It was only 100 people cap and I wanted to be mostly for people that are doing $10 million or more in sales in their business or they’ve had the next 10. So, $10 million is kind of like the main number, and most of them are in that 10 to 15 million range from the membership. Some of our members are doing a couple hundred million in sales.


And then I wanted to bring in instructors that are not just based about me. So, I brought out 22 different instructors that have all either done over $100 million sales, have been seen by over 100 million people, or spent over $100 million on ads. So, that’s how the name 100 Million Mastermind experience came from.


The reason I added the word experience, it’s 100 Million Mastermind experience was the experience is how people create memories. And so, Justin and I are at an event together at the Marriott Ballroom. It’s very different if Justin and I were at the same exact event at a mansion or at Dallas Cowboys Stadium or Shaquille O’Neal is up on stage, like I want to create experiences and I was the concept behind it.


And so, I started bringing in celebrities and athletes, people I wanted to interview so that people can hear. What does Mark Wahlberg think about this? What does Floyd Mayweather think? What does Hulk Hogan think? Kris Jenner, all sorts of interesting characters, what are their thoughts about investments? What are their thoughts about their career as a personal brand? Last, we just had Charlie Sheen. This is not a typical person interview, right? But I want people to get in different types of dynamics of different types of characters from business moguls, celebrities, and athletes.


And then The Avengers is very similar, except it’s a larger format. They have 174 members and growing that can go up to 200 or 300 members because we can do large-scale venues, unlike 100 Million Mastermind where we’re doing mansions and smaller venues. It’s like a wedding every time. I got to plan out five different wedding dinners, basically, we think about it. So, I need smaller venues.


The Avengers is half real estate and half investing, so half people are learning about real estate and half people are there to learn about investing in deals that it’s a lot more large-scale mastermind. And then I’ve Elevator Nights which is free. I’ve thrown that 48 times, totally free. There are 300 to 1,000 entrepreneurs at each event. There’s no cost, there’s no sponsorship, there are no tickets, there’s no sales from stage, nothing. Just smile like Robinhood, like I like to give back and it causes a lot of community in each city that I go to as my excuse to rally the troops and let people network in those cities.


Justin Donald: I love it. Well, I appreciate you sharing that. It’s funny, I have people on my show and I always want them to share all their stuff. And I’ve got friends that are like, why are you letting them share their mastermind? They’re a competitor. It’s a competing mastermind, right?


But I look at it as like we all help each other out, like the whole idea of a mastermind, I think everyone should do it. Everyone should find a group or a community like you could form your own and you could do that a lot cheaper. So, if it’s a financial kind of constraint that you have, then find your own and make sure you find people that are super disciplined and people that play the game of life and business and learning and education and leadership at a higher level than you, and do that.


But for most people, they’re not going to do that or they’re not going to find the people. And it’s just easier to show up to someone else’s event where they can mix and mingle and learn and get access to different deals. And I just think, everyone should have a tribe or a community of like-minded people that they can learn and grow with and experience life with. So, I love what you’re doing. I think it’s so cool. Where can my audience learn more about you? Where can we go to find you?


Dan Fleyshman: So, all my social media is the same. It’s just @danfleyshman. And it’s also important for you guys who are listening, your bio should be the same, your screen name should be the same, your photo should be the same across all platforms. So that kind of like that game memory. Oh, here’s the girl with the blue shirt and glasses. You want to be on the blue shirt and glasses on every single profile so people remember.


Justin Donald: That’s good. I like that. Well, I know we’ll have people come check you out. One thing I’d love to say is just for anyone that really wants to learn the lifestyle, investor skills and strategies apply to the world’s most exclusive mastermind of savvy investors looking to upgrade their lives, take control of their time, and build their wealth, and find invisible deals that you cannot find anywhere else that are de-risks, that are set up in a way where you win going into the deal. So, check that out at LifestyleInvestor.com/mastermind.


And I like to end my show with the same question and that is this, what is one step that you can take today towards financial freedom and towards a life by design, not by default, but one that is inspiring and exciting and it’s one on your terms? Thanks. And we’ll catch you next week.

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