I Have $12M But I'm Broke Every Month

Summary

Moneywise Podcast Episode Summary

Episode Title: I Have $12M But I'm Broke Every Month
Air Date: July 28, 2026
Host: Daniel Burke
Guest: Brandon Harris, founder of Playmaker

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Episode Overview

In this radically transparent Moneywise episode, Daniel Burke sits down with Brandon Harris, who sold his sports media company Playmaker in a deal touted at $54 million. Brandon reveals the true, much lower post-earnout number that hit his account, and candidly discusses the stress, challenges, and lessons from his acquisition journey. The conversation gets personal as Brandon unpacks his early responsibilities supporting family, his current investment strategies, and why—even after hitting an eight-figure exit—he still feels “broke” every month and is driven to keep building. This is an unvarnished look at wealth, ambition, and the founder’s mindset rarely shared in public.

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Key Discussion Points & Insights

Brandon’s Background and Story

• Early Privilege and Abrupt Setback ([02:08])

  • Brandon grew up privileged, attending private schools until the 2008 financial crash hit his family hard: his dad went from making high-six figures in real estate to driving limos. At 18, Brandon became the primary financial support for his family.
  • “Everything I was getting in college went directly to them… I was paying their rent, my college rent and all that stuff at the same time.” ([02:53])

• Entrepreneurial Beginnings ([03:21])

  • Started multiple small ventures: basketball training, web design, then moved into e-commerce, selling millions of t-shirts online.
  • Discovered media/influencer marketing by buying $15 Facebook posts, which led to building a media empire with 20–25 million followers.

The Playmaker $54M Acquisition—The Real Story

• Deal Structure & Earnout Complexities ([05:34])

  • The headline $54M deal with Better Collective was heavily backloaded:
    • Upfront: ~$15M (at time of closing)
    • 3-year earnout: $10M each year, milestone-based, plus a $10M “stretch goal” tied to aggressive revenue/net income targets.
    • Earnout metrics linked to Playmaker’s and Better Collective’s North American performance, making them convoluted and difficult to track.

• What Brandon Actually Made ([06:59], [08:13])

  • Due to earnout conflicts and the acquirer poaching key Playmaker staff for other projects, Brandon negotiated a simplified buyout.
  • “So where we actually ended up is somewhere between 25 and 30 million... where I netted out was about 12 million total.”
  • Notable Quote:
    • “The press release said $54 million, but Brandon walked away with 12.” – Daniel Burke ([08:13])

• Earnout Misalignment ([09:21])

  • Brandon would do a similar deal again but would insist on simpler and better-aligned earnout incentives to avoid acquirer behavior undermining his ability to hit targets.

The Emotional Toll of the Deal

• Stress & Burnout Early in the Earnout ([10:15]–[13:14])

  • Initial six months post-acquisition were “extremely stressful” with overambitious targets and little runway to deliver.
  • “We were definitely trending towards not getting any earn out at all.” ([11:45])
  • Frequent tension, layoffs, and personal struggles with health, sleep, and stress.

• Success After Struggle ([13:19])

  • When the major deals (e.g., shows with Shaquille O’Neal, Jalen Brunson) landed, things turned:
    • “The back half of that year was amazing. It was the thrill of my life… creatively fulfilling. I got to work with some of my favorite athletes in the world.” ([13:19])
  • Main satisfaction: providing stability and wins for his 70-person team and investors.

• Key Reflection on Founders’ Mindset ([26:12])

  • Zero days off after the exit.
  • “In order to be a founder period, I think you have to have some screws loose... You probably have some trauma motivating that. Failure is a huge fear for me. You know, just like I'm always in survivor mode.” ([26:17])

Personal Finance & Current Life

• Net Worth and Portfolio ([16:24])

  • Current net worth: $12M (“every dollar... still in the market”).
  • Investment breakdown: ~60% equities (mainly index/direct indexing funds, S&P500), 40% bonds; small positions in crypto, PE, venture.
  • Uses a credit line against the portfolio for personal and investment spending to avoid triggering capital gains:
    • “I want to keep all my money in there growing... so I don’t like to sell it. I want to keep as much of it in play as possible.” ([18:21])

• Debt & Spending ([20:23])

  • $3M tapped on margin/credit line, $1M mortgage on his house.
  • About $20K/month in income from dividends and $75–80K/year salary at his new startup.
  • “I keep it about break even. I keep as much money as I can in the market and that grows.” ([21:37])
  • Main expenses: mortgage ($12K/month), travel, experiences, daycare for kids, and a few comfort luxuries (house cleaner, cars).
  • Continues to live with a “cheap” mindset except for spending on experiences/travel.

• Future Goal and Motivation ([24:13])

  • His “enough” number is $20–25M net worth, but acknowledges work is mostly optional at his level.
    • “I’m always going to work... I think I have just kind of an obsessive desire to keep building and not stagnating.” ([24:13])

Reflections on Purpose, Legacy, and Parenting

• Why Keep Working? ([25:17])

  • He works because he thrives on building, impact, evolution, and contribution, not out of necessity.
  • “What would you do with your time? You're gonna sit in vacation and my kids are in school all day. What am I teaching them all day? The question is, what is my purpose in life? If I'm just sitting around not contributing, not building...” ([25:18])

• Trauma and Drive ([27:13])

  • Candid admission that early struggles and feeling like an underdog fuel his relentless work ethic.
    • “I literally have a tattoo of a chip on my shoulder.” ([27:13])

• Estate and Kids ([31:07])

  • Has made arrangements for kids to inherit his wealth, not interested in the fashionable trend of giving it all to charity.
  • Aspires for his kids to have a head start but worries about raising them without entitlement.

• Views on Legacy ([33:31])

  • Not motivated by “legacy” for its own sake. Believes attention spans and memory fade quickly after one’s death.
  • “I’m just not a buyer of legacy... I think you should do what you want to do and help as many people as you can in the short term, but not with the motive being that one day you're going to be appreciated…” ([33:31])

• Living in the Present ([35:45])

  • Biggest career regret: not being present, always locked on the next goal.
  • “The easiest way to be unhappy is to always have your eyes on a future target and not be present. I built this really cool company... no wins mattered, no excitement. I went years just being stressed and chasing this thing. Then you have the thing, and then you're left with—to me—the same imposter syndrome questions.” ([35:45])

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Notable Quotes & Memorable Moments

• On the True Payout of a Headline Acquisition:
  “The press release said $54 million, but Brandon walked away with 12.”
  — Daniel Burke ([08:13])

• On Founder Mentality:
  “In order to be a founder period, I think you have to have some screws loose...”
  — Brandon Harris ([26:17])

• On Present vs. Future:
  “The easiest way to be unhappy is to always have your eyes on a future target and not be present.”
  — Brandon Harris ([35:45])

• On Using Margin to Fund Life:
  “I want to keep all my money in there growing... I don't like to sell it. I want to keep as much of it in play as possible.”
  — Brandon Harris ([18:21])

• On Legacy:
  “I’m just not a buyer of legacy... Attention spans are what they are. I think you should do what you want to do and help as many people as you can in the short term.”
  — Brandon Harris ([33:31])

• On Personal Motivation and Trauma:
  “I literally have a tattoo of a chip on my shoulder.”
  — Brandon Harris ([27:13])

• On Purpose:
  “I think it’s building. I think it’s making an impact… If you’re not evolving and you’re stagnating, what is the point?”
  — Brandon Harris ([25:37])

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Timestamps for Key Segments

• [00:00] Brandon’s philosophy on presence and ambition
• [02:08] Early privilege, family’s financial collapse, and supporting family as a teen
• [03:58] Early ventures: basketball, web design, influencer marketing, growth into media
• [05:34] The Playmaker acquisition: mechanics, structure, and complexity
• [06:59] The real proceeds from the exit and earnout negotiation
• [10:15] Emotional toll and stress of post-acquisition performance targets
• [13:19] Creative fulfillment and exhilaration once the company turned a corner post-acquisition
• [16:24] Brandon’s net worth today and portfolio allocation
• [18:21] Using a credit line to avoid selling investments and triggering cap gains
• [20:23] Debt, spending habits, and burn rate
• [24:13] “Enough” number, work optionality, and purpose
• [26:17] The founder’s drive, trauma, and survivor mentality
• [31:07] Estate planning for kids and attitudes toward “legacy”
• [33:31] Why legacy isn’t a motivator and living in the present
• [35:45] Regrets about not savoring wins and always chasing the next milestone

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Final Reflections

Brandon Harris’s story is a nuanced and unfiltered look at what life after a major exit feels like for a founder—financially, emotionally, and existentially. Despite $12M invested in the market, Brandon feels nearly broke every month due to his high burn and habitual drive to keep building. He chooses to leverage his equity portfolio instead of selling, maintains a “cheap” lifestyle except for experiences, and focuses on evolving, not legacy. The episode is packed with hard-earned insights on negotiating earnouts, the cost of ambition, and the reality behind the glitzy startup headlines—offered from a founder who’s still on the eternal hamster wheel, chasing both self-actualization and the next big thing.

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For anyone navigating high-growth startup life or eyeing an exit, this episode is a must-listen for its raw honesty and inside-baseball wisdom.

Transcript

[Brandon Harris]

The easiest way to be unhappy is to always have your eyes on a future target and not be present. I built this really cool company and I had, I should have had a lot of fun doing it, but I was always, hey, I need to have this exit. I need to have this thing. And so as a result, no wins mattered, no excitement. I went years of, like, just being stressed and, like, chasing this thing. And then you have the thing, and then you're left with those same imposter syndrome questions. You're left with identity questions. Yes, you had your win. Now what?

[Daniel Burke]

My guest today built his fortune buying $15 posts on Facebook. PA 15 bucks in millions out. Subscribing to this show is an even better trade. It costs you nothing, and you get an episode like this every single week. Okay, so Brandon Harris, the headline says he sold his sports media company playmaker for $54 million. In this episode, he tells me the real number that hit his account. He also tells me about being 18 when his dad went from half a million a year to driving limos and suddenly becoming the college kid that was the one paying the family's rent. And he explained how he pays for his entire life today without selling a single share of stock. He also has a literal chip on his shoulder. I get to talk to founders just like Brandon inside of Hampton every day. It's a private network for high growth founders who are doing 25 million a year on average. If that's you, you need to check it out@join hampton.com now, let's get into the show. I'm Daniel Burke. Here's Brandon Harris on money wise.

Brandon, thanks for joining us today on Moneywise. How you doing today, man?

[Brandon Harris]

I'm doing great, man. How are you?

[Daniel Burke]

I am doing well. I'm excited to learn a bit about you today. Tell me what brings you to the show and who you are.

[Brandon Harris]

I am Brandon. I was the founder of Playmaker, which had a. The headline says $54 million exit. I'm happy to be radically transparent about the specifics of that. And then generally, you know, I'm in the investing world. Love numbers. Learning a lot from you in the pod and just excited to share my story, talk the numbers, and learn a little bit from you.

[Daniel Burke]

Awesome. And before we get into the $54 million acquisition story, how was money like in your life and in your family when you grew up? Tell me about how that was as a child.

[Brandon Harris]

Yeah, I. I grew up very privileged, to be honest with you. I was in private schools most of my life Until I turned around 17, 18, my dad was in real estate during the crash of 08 and basically he owned 10 properties. They all were foreclosed on. Our house was foreclosed on. He went from making a year and like living it up to driving limos and just trying to kind of to make it work. And so it definitely like my relationship with money changed dramatically and my appreciation for it changed dramatically. And I had to at like 18 years old, start taking care of kind of my entire family a little bit. And so basically roller coaster.

[Daniel Burke]

That must have been hard taking care of your family at 18.

[Brandon Harris]

Yeah, yeah. We had the loans, grants, everything I was getting in college went directly to them. I had, you know, part time jobs. I was doing some online stuff to try to scrape together money. I was paying their rent, my college rent and all that stuff at the same time. But I think in a good way it forced me to go and find ways to make money and, and be more responsible than probably most 18 year olds have to be.

[Daniel Burke]

And so you were really already an

entrepreneur early on, it sounds like.

[Brandon Harris]

Yeah, I was doing basketball training businesses. I was doing web design businesses for people. It was, used to be WordPress was the cool thing when I was 18 and so, you know, here 60 an hour there teaching kids how to play basketball. And eventually we built a gym off of that, we built a marketing agency off of that and kind of got started in the whole digital media and online marketing space from a very early age.

[Daniel Burke]

And so walk me through the transition from 18 taking care of your family with grants to eventually launching this business that for all intents and purposes was wildly successful.

[Brandon Harris]

Yeah, so the first thing was that training business. So I went and learned WordPress to build and improve our SEO and get new clients in that and then got a gym started to run Facebook ads and do Facebook posts on Miami Heat related posts saying, hey, if your son or daughter wants to get better at basketball, come try next level basketball. And so kind of to do everything, I learned a new skill and, and kind of went and did before I really knew how to do. And over time that led me to E commerce. We were selling millions of T shirts online for a company called Hoop Culture. And then I was buying influencer ads and posts. They weren't really called that. Then I was literally buying $15 posts on big Facebook pages like Basketball above all or whatever saying, buy a shirt for this discount. And we were doing crazy numbers. We were selling millions of dollars. But what I found more attractive was the page side of the business because it's 100% margin. They were selling these all day. And you know E Comm margins are pretty competitive and tough. And so that led me into media. I started acquiring, building, growing those assets, grew to about 20, 25 million followers across those. And then from there built a real media business with events, E Comm shows, all kinds of things. The questions just became what's the next best thing I can do with these assets that I built.

[Daniel Burke]

Cool. And the Better Collective deal, that was a $54 million acquisition. Walk me through the structure of that, the mechanics, the earn out, you know, all the details.

[Brandon Harris]

Yeah, so I was parallel pathing investment or, or getting acquired. And so Better Collective came in with an offer that had kind of basically what I was going to be able to raise at valuation wise upfront which was just about 15 million and then on the back end the ability to earn up to 54. And that was structured basically every year had is one of the most complicated structures by the way, the doing business with the Danish over there. That they are very detail orient and they structured things I think in, in a way that is a little bit convoluted and can be almost tough to track. And so it was like basically 30% was tied to their North American total net income and about 30% of it was tied to Playmakers revenue each year. And then about 30% was tied to Playmakers net income. And then there was like some other incentive targets. So basically every year there was 10 million additional you unlock and then there was a stretch goal on top of that. So it was a three year earnout period. So 10 mil. 10 mil. 10 mil. And then the stretch goal of an additional 10 was based on hitting a total revenue of about 75 mil or total net income of 25 mil over that three year period.

[Daniel Burke]

Okay. And so what did you personally see from that initial pay structure and then the earnout period over time?

[Brandon Harris]

Yeah, so where we actually ended up is somewhere between 25 and 30 million. And basically after year one they were starting to try to pull kind of employees. They were trying to say hey, we want your COO to go and launch this for this one of our other companies. We want your head of YouTube to go and build our YouTube strategy for these other things. And so there was conflicts of interest because our earnout was tied entirely to our Playmakers performance almost entirely. And so they wanted to go and take this and use the parts, use the people and stretch us out. And so then there was a negotiation after year one and I was like hey listen, clearly we're trending towards hitting a lot of this. But there's like misaligned incentives. And I think we should just negotiate and we should just buy out some of this earn out. And so we landed about 25 the key employees. There was four or five key employees they were given. Basically if you stay for the full term of the earnout, you get this additional bonus. On top of that, the employees, all who are not key employees, split up a $1 million bonus pool that we negotiated where I netted out was about 12 million total.

[Daniel Burke]

All right, so the press release said $54 million, but Brandon walked away with 12.

Here's what happened.

Most of that deal was an earnout. An earnout means you don't get the money at closing. You get it over the next few years only if the businesses hit targets the buyer helped set. Brandon's targets were tied to revenue and profit numbers three years out while the buyer was pulling his best people to work on their other companies. Sometimes in earnouts like this, there are misaligned incentives. So what Brandon did was he negotiated an early buyout of the earnout and took the certain number over the maybe number. That, in my opinion is smart. Acquisition horror stories and earn out periods and all the different mechanics that go into a company sale are conversations I hear inside of Hampton constantly. If you are currently going through this or you've gone through this before and you just want someone to talk to about it, go to joinhampton.com it's a great community for high growth founders doing 3 million a year or who have

already egged exited for 10 million a year or more. Okay. And so looking back 54 million down to 25 million and some of the different milestones that come with a typical earnout period, would you do that again?

[Brandon Harris]

I think I would do it again. I think I would negotiate simpler earn out targets and I think we would be really kind of deliberate about aligning incentives. And I think that that was really the biggest issue was that they, they bought us not just to build this, but to go and build and help the other parts of the business, which is totally a fair and valid reason to do so. But then you, you should be considering that as far as protecting employees and assets and making sure that they're being used to hit targets or those targets should be kind of blended total group targets, in my opinion.

[Daniel Burke]

So about $38 million earn out and if I read correctly, tied to a $75 million target. So when you look back on those milestones, tell me how that felt during those periods, knowing there's this effectively a hundred percent earnout over the life of three years that was tied to such stringent milestones.

[Brandon Harris]

Yeah, I, I think the first six months especially were extremely stressful. And you're just. Especially because a lot of the plans take time to develop. Like, we came into this with, hey, we want to do these big events. We want to do these big shows with talent. And obviously, like, you're not doing a deal with Shaq over a period of a week. You know, there's like conversations and multiple drafts of offers and legal. And Shaq's on vacation. And let's come back to this. Let's circle back next quarter. And so the first six months, we had basically no product. We had these kind of lofty goals, and. And we were under delivering. Right. And a lot of the belief.

[Daniel Burke]

What was your revenue in the first six months?

[Brandon Harris]

What did that look like revenue against probably a $17 million target? I think we probably did 3 or 4 million in that first six months. And I think people were starting to be pretty stressed. And I think the. The feeling was that this is trending towards not being a successful acquisition. And then, then all those deals started to happen. And then we got Shaq, and then we got Jalen Brunson. Then we got a lot of these other shows, the OGs, and they all kind of came within a period of one or two months. And from a totally kind of stressful failure to. Now this is really, really exciting. We're buzzy, we're doing crazy numbers, like, where we may actually hit that stretch goal. But, like, those first six months, I think a lot of faith was lost. A lot of kind of tense things were said and. But yeah, we were definitely trending towards, you know, not getting any or not at all.

[Daniel Burke]

What are the conversations like in the room where it happens when you're sitting down with the company who acquired you, some of your peers and colleagues on the C Suite, and then you're stressed because you're at 3 or 4 million of the $17 million milestone. I mean, how does the. How does that feel?

[Brandon Harris]

Yeah, I think the other important thing to note is just like their business model was kind of a sports betting affiliate business model at the time. So the media model is very different. And so they didn't really understand the space too much either. So you compound that with the, hey, we're under delivering. And then, hey, we don't really understand that this stuff takes time. We haven't seen it be built. It got really ugly. There was, you know, a lot of Conversations, removing people about, you know, all kinds of different. The cutting budgets, layoffs, all kinds of different things. People almost like, accusatory, almost like, hey, like, you inflated your forecasts and all that stuff. And so it was. It was an ugly six months. It was very stressful. And I definitely, like, that was probably the least healthy I've been personally in my life.

[Daniel Burke]

Was that six months, like, healthy physically, mentally? Both.

[Brandon Harris]

Yeah. I couldn't. I couldn't get myself to work out. I couldn't really sleep, you know, wasn't managing stress well at all. Kind of was emotional and. And I. I look back at that period and kind of just regret how I personally handled that, navigated the stress, handled balance, all of that.

[Daniel Burke]

So it's interesting. You said you would do it again. Why would you do that again? That sounds terrible.

[Brandon Harris]

Well, then the back half of that year was amazing. It was like the thrill of my life. You know, I got to work with some of my favorite athletes in the world making some of the most creative and special content. And, you know, literally it was in Shaq's house at the studio, and we were. We were talking through things, and, you know, it was a total thrill of my career. It was like, it was. It was creatively fulfilling. It was a huge success, and so it made the rest of it worth it. And I think the other piece to this is, like, handling the weight of, you know, whatever 70 team members that we had and just giving them all a home that was stable, that had good benefits, that had, you know, all kinds of, like, they were able to go and work their sports dreams and all of that. And so for me, that was a big weight off of my shoulder, and that made me feel really good. They. They won, investors won, I got a win, even if it wasn't, like, the most I could have squeezed out of the business. Like, everybody won. So I had no overall regrets. Looking back.

[Daniel Burke]

So you mentioned the. The acquirer was not necessarily familiar with this media space. When you look back, were you going after them in the acquisition, or did they come inbound and you kind of entertained their offer? And would you recommend to other founders to go have someone that maybe doesn't necessarily understand their business model or their industry be the one that acquires them?

[Brandon Harris]

Yeah, there's. There's certainly pros and cons. Like, they wanted to go further into the media space and away from what they were doing, and we were a step in that direction. So it was kind of like a sexy, fun, you know, business that was a little bit outside of their Core model, but complimentary potentially. And they thought they could also bring us into their world a little bit and help the other businesses. And so I think, you know, now Playmaker is the flagship of their entire umbrella of brands. So I think they would look back at this as a huge success. And I would say they were an M and A based business. They were basically private equity, but their goal publicly was to be the world's largest sports media group. And so basically, like, I think if they were honest with themselves, I think they probably had really big, you know, vision and eyes at that time. And I think they, they've now been much like three rounds of layoffs and reorgs. And I think they're probably now focused on a less ambitious but more profitable business. And I think overall, like, I would, I would recommend going with like a, a business in your country, if you can, as an acquirer. I think there was a lot of kind of communication and cultural differences there. And then there was a US C suite and then a global C suite, and then they got rid of the US C suite. So everyone I was dealing with was gone. And so there's no relationship globally. And so there was a lot of complicated things to navigate with. Just dealing with the company that's headquartered in Copenhagen.

[Daniel Burke]

Yeah, yeah, sounds like it. It sounds like a really stressful front end for an incredibly rewarding back end. So that's great. So back to the personal earn out. You got 12 million. And where does that bring your net worth today?

[Brandon Harris]

12 million.

[Daniel Burke]

Okay, great. So walk me through where that money is. Is that liquid cash? Do you have it in public equities? Tell me more about where that is.

[Brandon Harris]

Yeah, so I have basically every dollar of that still in the market. It's about 60, 40 equities, bonds. It's not totally 60, 40. I have a few small bets in crypto. I have a few other, like private equity, stu credit. I have a little bit of venture and angel stuff, but the overall blend is like close to 60, 40. I'm a big believer in stocks and so all of that's in the market. I fund any kind of personal expenses and investments with my credit line that's secured on that to avoid, you know, the triggering capital gains taxes and things like that.

[Daniel Burke]

Okay. And so when you say into the market, is this like s and P500 or index? Like what, what is. Are you stock picking?

[Brandon Harris]

So I have a wealth manager that does the majority of the placements there. There's some. Most of it is in a, I think a tax loss harvesting Fund direct indexing called Parametric. And, you know, basically, like, we view that as it's basically S and P returns, but also the benefit of selling when they're down. And so you're kind of showing a paper loss. So to me, there's an advantage in the spread of like, yes, you're getting the 10 or 12% top line, but you're also, there's another couple percent you're squeezing out based on tax benefits. And so that's where the majority of it is. I have some kind of concentrated bets. I have 600,000 in a Robinhood account where I'm making bets, usually mostly AI and robotics and infrastructure around that. And then my wealth manager will come to me with like, for example, we just got into Nokia and there's a few other SanDisk we had a nice run with. And so he'll come to me with a few of those. But it's largely in the indexing.

[Daniel Burke]

Okay, cool. And you mentioned the credit line. Tell me more about your thinking behind the credit line.

[Brandon Harris]

Yeah, I want to keep all my money in there growing. I'm a big bull on, on kind of the stock market and where I think it's headed. And so I don't like to sell it. I want to keep as much of it in play as possible. I don't mind having kind of some leverage there. And then also the interest expense on that credit line that I'm using is another thing that goes against my taxable income. So there's a lot of kind of benef on the credit line. Yes, I'm paying like, let's call it five and a quarter in interest on that. But that's all going against my, my cap gains and everything.

[Daniel Burke]

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Yeah, and what's the actual total tapped credit there in the margin debt?

[Brandon Harris]

I. I have about 3 million tapped on that. And then I have a mortgage on my house is another million. So I have about 4 million in, in debt.

[Daniel Burke]

Okay, and let's move to like the personal spending then. If you have most of that, it sounds like liquid in public securities and you know, index funds. What are you spending? And is that coming from a different cash account not included in that 12 million, or do you use all of that on your credit line?

[Brandon Harris]

Yeah, right now I take dividends. I take 20,000amonth. I've gone into, I've started a new company. I pay myself about 75, 80. Just big discount from the corporate 250 that I was making previously.

[Daniel Burke]

So 80 a year then.

[Brandon Harris]

Yeah. Okay, so making about 280 in income and then. So that's where most of my, my spending comes from. I am very cheap, naturally. And, and I try not to buy a ton of like, material things, but I do spend on experiences, travel, stuff like that pretty aggressively.

[Daniel Burke]

So 2, 80 a year. And what are you spending per month?

[Brandon Harris]

Close to that.

[Daniel Burke]

Okay, so pretty much break even.

[Brandon Harris]

Yeah, yeah, I keep it about break even. I keep as much money as I can in the market and that grows.

[Daniel Burke]

What types of experiences are you spending money on?

[Brandon Harris]

Yeah, we travel with me and my family. I got two young kids. We go, we travel, you know, we go to the Bahamas every year. I go to Vegas pretty often. I go to the Boca Raton, is a beautiful place down here, Staycations. But we spend, we spend probably at least 30, 40% of my total expenses on just travel and, you know, restaurants and things like that.

[Daniel Burke]

So like 80, let's call it 80 to 100,000 a year toward experiences, travel, you know, family stuff, restaurants. So then what's the mortgage cost? You mentioned a million in debt on a mortgage. Is that Something you're paying monthly?

[Brandon Harris]

Yeah, my mortgage is about 12,000amonth right now.

[Daniel Burke]

12,000amonth. Okay. And then the rest of the miscellaneous spending then. Where does that go?

[Brandon Harris]

Not very many places. I don't spend a ton outside of those things. It's, you know, we got kids, school, we got a couple cars, but, you know, everything else is pretty minimal.

[Daniel Burke]

Yeah. So kids are in public school then. Do you have house cleaners?

[Brandon Harris]

Yeah, yeah, yeah, we got, we have a weekly house cleaner. I think we pay 400amonth for our, our house cleaning. Nothing excessive. And then one kid is in daycare, which is. I think it's about 1,200amonth. And then other kids in public school.

[Daniel Burke]

I've heard daycare. I have two kids of mine, I have a third on the way. You hear so many different. I talk to people all the time. How much does daycare cost? You hear 1200amonth. You hear 12,000amonth here. It's daycare.

Daycare is one of those things that

could totally break the bank if you're not careful.

Well, that's cool then.

So 75,000 a year then, from your current company. How do you arrive at that number?

[Brandon Harris]

I basically, I'm a believer that until I turn a corner and I'm, this company is profitable and growing at the same time, then I think 75 is an appropriate amount to take. I've raised, you know, about 1.5. I put in another million of my own, so companies well funded. But I, I'm not a believer in paying myself, you know, until I earn it. So this is, I'm taking basically what I, I deem to be a starter salary. It's less than most of my employees.

[Daniel Burke]

Yeah, I would say so. When you think of your, your threshold number on money wise, we ask what's the number you're. You're going for before you can kind of chill and stop working? Obviously, I would say you haven't arrived there yet. Given you're still paying yourself a salary and you have, you know, a new company, what is you.

[Brandon Harris]

Yeah, I think first of all, I think I'm always going to work. I think I have just kind of an obsessive, like, desire to keep building and not stagnating. I think that was. I didn't even give a second thought to stopping after this acquisition. I think I would have been bored and like unhappy with myself, honestly. But I think if for me, I'd like to get to 20 million, I think as long as you're over 15 in theory, it's work is an option in my opinion, no matter how aggressively you spend. But I think, yeah, for me, 25 would get me kind of my ambitious. Like I could have a crazy. I want to build this, this big compound farm thing with robots and drones and stuff, but I think I'm another exit away probably. Yeah.

[Daniel Burke]

Because I mean, with the 4% rule and given your fairly low spending respective to how much you could spend, you've sort of already gotten to the point where you could stop. So a lot of people would say, well, you have 12 million invested and you're still working.

Why?

Because you like it.

[Brandon Harris]

Yeah. What would you do with your time? You're gonna sit in vacation and my kids are in school all day. What am I teaching them all day? The question is, what is my purpose in life? If I'm just sitting around not contributing, not building, building.

[Daniel Burke]

So then what is your purpose in life?

[Brandon Harris]

I. I think it's, I think it's building. I think it's making an impact. I think it's, you know, creating and, and finding ways to help others and, and help my family. Like, I think always evolving is really kind of like, I think if you're not evolving and you're stagnating, you know, what is, what is the point? Like, what are you, what are you doing?

[Daniel Burke]

Yeah. When you think back on the playmaker deal and not taking time off or actually first I'll ask, how much time did you take off? I assume you at least took a week or two.

[Brandon Harris]

No, zero days? No.

[Daniel Burke]

No time.

[Brandon Harris]

No time.

[Daniel Burke]

Do you think there's some fear motivating that, like the, the constant go, go, go.

[Brandon Harris]

Yes, there's, there's. Yeah, I think the, I think where I've landed on a lot of this is that in order to be a founder period, I think you have to have some screws loose. Like, I think there's much safer ways to make a stable income. I think you take so much risk, you eat so much rejection all the time. You probably have some trauma motivating that. You probably have some major fears. Failure is a huge fear for me. You know, just like I'm always in survivor mode, I think is really the reality. And I think I told myself I'd do it differently. I told myself, you know, all these things and it comes time to it, like. And I just don't do it. I just, I just kind of. I'm thinking about what can I do next? How can I. How can this not be my final act? Or, you know, know, how can I

[Daniel Burke]

keep growing so you mentioned trauma. That's an interesting word. Why did you choose that word in respect to some of the fear that's motivating you now?

[Brandon Harris]

I, I think that's a lot of. To go through all of this stuff. I think you're, you're probably fighting demons or you know, you're. Hey, like for me it's really like a second act kind of thing. It's like, hey, I felt like I was kind of a failure in high school. I didn't get the grades, I didn't get the girls, I didn't get into the colleges I wanted. I think most people looked at me as somebody who was unsuccessful and not likely to be, you know, great at anything. And so I think there was a huge part of me that was like, hey, like let's get serious now. Let's prove them wrong. I have a huge chip on my shoulder. I literally have a tattoo of a chip on my shoulder. And so that's cool. Yeah, I think that's the reality of things is I got a lot of stuff tied up but I think like it's made me not be the lazy person that I think I maybe naturally was programmed to be. And because, because it's even just being still is just it, it can, it can be very challenging for me.

[Daniel Burke]

Why do you think you were naturally programmed to be lazy?

[Brandon Harris]

I just, I just have to assume that way because I was in high school and I was like, I was convinced I'd be in the NBA. I'd convinced I was going to do all these things. I got probably a two point something gpa. I didn't make any of the BAS teams I wanted and it was purely an effort based thing I think. And I just, I, I think I, I sent to some boarding schools. I had all kinds of stuff where like we, we went on these hiking expeditions and we had this, this three day thing with no food. You had to go find your own food, build your own shelter, all that stuff. And I, I think that was probably around the time where I kind of woke up and I said like what you're doing?

[Daniel Burke]

Yeah, I want to call back to something on the invested front. You said you put a million dollars in to Invested Inc. That's a lot of leverage of your personal money into this startup. Why'd you do that?

[Brandon Harris]

Well, it's like if I don't believe, who will? And I wanted to go faster this time. I'm committed to building something great and so I'm going to do as much of that as I can and I hope I don't go to zero doing. Doing it, but I hope I'm good as, as good as I believe I am as an operator and I won't go to zero.

[Daniel Burke]

Yeah, I think a lot of people hear you say that and can resonate with that. I know a lot of founders personally that will resonate with that. Tell me what happens after Invested Inc. What is success? If you were to paint a picture of two to five years from now and then what do you do? Do you just keep going? Or if you hit that 25 million that you've been talking about, do you stop and maybe just travel with your family and enjoy life for a while?

[Brandon Harris]

Yeah, I don't, I don't think I'm ever going to be cool with just traveling. Like I, I would love, I love traveling. It's my favorite thing to do. But I think like, I need to come back to some purpose and maybe when my kids grow up and it feels like I can teach them more and maybe influence more. But right now they're four and two and it's kind of like how much can I actually shape and teach them? So I think I'm going to keep building. I have a second side business that I'm incubating also with two of longtime friends that are also post exit media founders. So we have like at robotics, we have AD Artificial. We have a lot of these kind of AI and robotics usernames that we're incubating and growing and maybe it'll be an AI and robotics media company that we spin out. But I'm always kind of looking, I'm always like, you know, I'm inspired and I want to keep evolving. So I'll probably be building things until I die.

[Daniel Burke]

I also have two kids, 4 and 2, same ages. And I love asking guests on this show about how they think about their money and what they're leaving behind as it pertains to their kids. Have you thought much about that? I know 4 and 2, obviously they're not super old yet, but what are your thoughts on leaving money to your kids?

[Brandon Harris]

Good question. I have all the estate planning stuff set up. They're going to inherit a lot of money hopefully if I don't ruin things over the next, you know, however many years I'm alive. But the, the gist is, is like I'm not a. I, I have some money in, in accounts for them that's invested through Acorns and some of those other other tools and places. But the, my attitude is I think they're Going to inherit a good bit of money. I don't want to disadvantage them. I don't want to reroute it to some charity that's gonna, you know, eat 95% of it with their expenses and whatever else. And so I, I'm thrilled that I'm able to give them a head start and I am going to try to make them as not spoiled as possible and, and ingrain positive messages. But it'll be their money to do with whatever they want.

[Daniel Burke]

Yeah. Do you, do you imagine they'll take after their dad in the sense that they have to just work and they can't. They can't not. Or will you ideally set them up to where they maybe are work optional?

[Brandon Harris]

Yeah. Hopefully they have balance. But I know my 4 year old has got my competitiveness. Like she's, she's totally intense. So we'll see about the 2 year old. But I think they're were probably wired like me a little bit.

[Daniel Burke]

Yeah. Earlier you said Jaylen Brunson and are you a Knicks fan?

[Brandon Harris]

You know, no, I'm a huge Heat fan, but I've like through the show.

[Daniel Burke]

That's right. I barely saw in the background through the show.

[Brandon Harris]

I like out of all the athletes I worked with, those two are the nicest, like the most genuine, authentic nice. Like it's not an act. They're just like great people. And so I've learned to love the Knicks despite hating them most of my life.

[Daniel Burke]

Well, I think when it comes to leaving a legacy, I've talked to a lot of people who have very diff. Different opinions on this. I mean, some people will say I don't want to leave my kids anything because I don't want them to have the advantage that I personally would love to leave my kids an advantage. But a lot of people just. No, I want them to start and make, you know, struggle and experience what I had to experience to get here. You don't seem to think that way. And from your story you grew up sounds like affluently with wealth. Is there a part of you that is scared that your kids won't have to experience struggle?

[Brandon Harris]

I'm not scared of that. I think you can win with or without struggle. I think you can go and be affluent and just have the right kind of point of views on things and go get a solid job. And I think most people should not be entrepreneurs. And I think frankly it is not the right path for most people. I know it's glamorized and all of that, but I think most people are Going to lose money, they're going to be less happy, they're going to work harder than they need to. And you know, I'm big believer in balance. I wish that I could appreciate balance more, but I view that as actually, you know, a weakness of mine. But the to your legacy point, I've gone back and forth on this and I think what I have now realized, having seen, you know, great, great men and women die, you know, I, I think it's like, especially with how attention spans are and everything. I'm just not a buyer of legacy. I'm not a buyer of like long term thinking anymore. I'm not a buyer of like, I think you should do, you know, what you want to do and help as many people as you can in the short term, but like, not with the motive being that one day you're going to be appreciated or exalted or got to get a statue. I don't believe in that. All I think you do, you live for today. You maximize your time here on this earth and don't give two seconds thought to what they're going to say after if you're going to have a textbook or you're going to have any of those things that cover you. Because I just don't think the world is like moving like that anymore.

[Daniel Burke]

Yeah, I mean, it's incredibly rare for anyone to remember your existence two generations after your life. I mean, I mean, I don't know the name of my great great grandmother off the top of my head. I could go figure it out. Out. But you know, it's like, that's an important family member. Right. So it's like maybe three grades. I think the second grade I do know. But, you know, it's a legacy is an interesting thing. I think we feel like we have to leave a legacy. I think some of that comes down to what we're taught and how important it is in history books to read about people who left a mark on the world. But ultimately, you know, I think that's a good mindset to have like live in the moment, live with what you have, live with what you're given. I mean, tomorrow you might not see it tomorrow, you know, in some cases. So.

[Brandon Harris]

Yeah.

[Daniel Burke]

That's awesome.

[Brandon Harris]

Yeah. And I think the, the easiest way to be unhappy is to always have your eyes on a future target and not be present. I think that that was like if back to regrets on the acquisition or whatever. It was just like, I built this really cool company and I had a, I should have had a lot of fun Doing it. But I was always, hey, I need to have this exit. I need to have this thing. And so, as a result, no wins mattered, no excitement. You know, I went years of, like, just being stressed and, like, chasing this thing. And then you have the thing, and then you're left with, like, what? And then you're left with those same imposter syndrome questions. You're left with identity questions. Yes, you had your win. Now what? Could you do it again? Was it you? Were you lucky? All those things that you mentioned. But I think the key is, like, maximize today, and that's all you can really control.

[Daniel Burke]

Yeah. Awesome. Brandon. Well, this has been an incredible episode of Money Wise. I want to ask one final question I ask every guest. If you don't see tomorrow, you get hit by a bus today, and it is the end of your life. What do you want to be remembered for?

[Brandon Harris]

Just being a good person, you know, having good morals, helping people, making cool things and fun, content. But I think I feel really good about how I'll be remembered. I'm okay if I'm not celebrated or exalted. Like I said. Like, I know that most of the people who I've worked with and who I've built with will remember that I helped them advance in their careers or I helped them, you know, do something challenging. I know my family will remember that I was always there for them. And so for me, that's. That's enough.

[Daniel Burke]

Brandon has a pretty wild story. $12 million from the exit, and every dollar of it is still on the market. He borrows against the portfolio at around 5% instead of selling, and he has 3 million tapped on a credit line. He pays himself 75k a year at his new company, which is less than most of his employees. And he put a million of his own money into it. His number is still about 20 million. He's taken zero days off after his first exit, and he's still chasing that bigger number before he really calls it quits. But in his defense, he doesn't really ever want to call it quits. He's going to work until the day he dies. There's something Brandon said that I've been

thinking about since we talked while he was building Playmaker.

No wins really seemed to matter.

He was so locked on the exit

that he never really enjoyed the thing that he'd remember as the thrill of his career.

Career.

He got the money and was left with the same questions. That's really the whole episode. And really Brandon's story, conversations like this one with Brandon on moneywise are like conversations we have every day inside of the Hampton community. It's a private network for founders and CEOs doing on average 25 million a year in revenue. If you're doing 3 million a year or have exited for 10 million or more, check out joinhampton.com I think you're

going to love it.

And that's money wise.

I'm Daniel Burke.

I'll see you next week.