Nick Huber returns to MFM to walk through how he scaled his self-storage portfolio to 61 properties and $103M in acquisitions — and how he’s used his 30M monthly Twitter impressions to build a portfolio of “sweaty startup” businesses including Support Shepherd (overseas staffing), Ari CostSeg (cost segregation), Tax Credit Hunter (ERC credits), and Titan Risk (property insurance). Sam and Nick also go deep on decision-making, the fear that holds entrepreneurs back, and what motivates them now that money is no longer the primary driver.
Speakers: Sam Parr (host), Nick Huber (guest, self-storage investor / sweaty startup operator)
Opening: Sam’s Investment and the Storage Portfolio Update [00:00:00]
Sam: What do you — I’m an investor of yours. I don’t remember exactly how much I invested, but you’re like one of the few — I think you’re one of three things I’ve done. How’s it going?
Nick: It’s going great. I see the returns. But how much do you have in total self-storage now — like $100 million or something?
Sam: I think last time you came on it was 15 properties or so and $20 million.
Nick: We now have 61 properties, 1.8 million square feet of storage. We’ve acquired it for $103 million. We’ve raised $41 million from people like you who invested in it. It’s been a whirlwind — the last two years have been crazy.
Sam: Would you say $100 million worth of — is that how much you paid for it?
Nick: I don’t know how much it’s worth. I don’t either. I mean, we could guess, but look — the real estate market has no mark-to-market. With Elon Musk, you can see how many shares of Tesla he has and the value of those shares. I have no idea. I can make educated guesses, but if we sold our portfolio today — I don’t know, six months ago we might’ve been able to sell it for $190 million or so.
Sam: Oh, that’d be awesome.
How Sam and Nick Met [00:01:30]
Sam: The way I met you — it’s kind of a creepy story. Years ago I dated this Polish girl, and I remember seeing your picture on Twitter. Your face reminded me of hers. Are you Polish?
Nick: I’m German. Huber — my mom is a Gottfinger, so yeah, very German.
Sam: I remember seeing your picture and being like, “Oh my gosh, this guy looks almost Polish.” And then I was driving cross-country and I did a Twitter Live or something, and you commented, and I just called you on your phone. I put it on speakerphone and we started talking — that’s how we met. Right?
Nick: Yeah. Now we know each other quite well. I think we’ve punched each other in the face, we’ve guarded each other and fouled each other in basketball, we’ve hung out at a couple of conferences, and we talk several times a week.
Sam: I appreciate it, man.
Nick: I appreciate you too. When he told me he was a decathlete, I was like, “Yeah, you’re not that good.” And then I looked up his times and was like, “Oh, he’s better than I was.”
Sam: You ran a 47 in the 400?
Nick: I opened 47. Splits are crazy — your coach wants to tell you that you ran really fast splits to pump you up, but he told me I ran a 46.7 split one time. I’d believe that. My fastest opens were only in the 48s and 49s and my splits were 47, so you’re probably a second faster than I was.
Building the Self-Storage Empire Through Twitter [00:04:00]
Sam: For those who don’t know — you went hard on Twitter when COVID started. There’s this text message group: me, you, Shaan, Austin Reef, Nikita Beer, Sahil Bloom, Greg Eisenberg. You were an addition that came on about six months or a year after the group started. But the reason the group started was you all went hard on Twitter around the same time and liked each other’s stuff — you were “thread boys.” Of that $40 million you’ve raised, how much came from Twitter?
Nick: 96% of it came from Twitter.
Sam: No way — is that real?
Nick: Yeah. My entire real estate private equity company was built on the back of Twitter. We bought our first self-storage facility, raised $500K — my dad took a mortgage out on our house to do it. He didn’t tell me that at the time because we were middle class, and he basically helped me raise the money for that first deal.
Sam: Everybody says “you’re not self-made” — what’s yours?
Nick: My not-self-made story is that my dad was the first investor in my first storage building. But then we ran out of money and had to buy our second, third, fourth, and fifth properties with our own cash from our moving company. Then fast-forward to Twitter — I’m tweeting about deals, tweeting about some of our properties, and people are DMing me asking to get on our investor list. Fast-forward to today: we’ve raised $40 million from 320 people, we have 2,000 people on our distribution list, and it’s changed my entire life.
Sam: What’s $40 million divided by 320 people?
Nick: About $125K average. We have some investors up over a million bucks.
Sam: That’s crazy. I wish I would have done a million dollars when I saw that check.
Nick: That deal you’re in is going to be a really good deal. We refinanced it in a really crappy refi environment, but we’re going to build some climate-controlled storage on that property. It was a big deal — uncomfortable. We bought it for nine million bucks, and then we bought another small property and another portfolio after that. Our basis is about $15 million. We put about 30% down, we have about $12 million in debt because we refinanced and pulled out some cash, but now it’s got a million dollars of net operating income and it’s a $20 million-plus property.
Sam: That’s crazy. I remember seeing that check.
Support Shepherd: How Nick Turned an Affiliate Deal into 15% Ownership [00:09:00]
Sam: What do you want to talk about today?
Nick: I want to talk about the Shepherd thing.
Sam: Yeah, let’s do it.
Nick: So that company is phenomenal and it kind of kicks off our discussion. My goal — real estate is in a really good spot, I still spend a ton of time on deals and strategy, but I have a lot of bandwidth. I also have 30 million impressions a month on Twitter. My goal right now is to build a portfolio of ownership chunks in great small companies — sweaty startups.
Austin Reef was supposed to come on today and had a last-minute board meeting, so he and I and you were in a group chat and he was like, “Let’s talk about non-advertising ways to monetize media followings.” And you did it. I don’t know exactly what your equity stake is worth, but you’ve done it to the tune of $100 million in real estate.
Sam: You’re also doing it in a bunch of different ways.
Nick: Yeah. Shepherd is the ideal story. Late 2020, November or December, I wanted to hire someone in the Philippines. I met Marshall Haas who owns Support Shepherd. I was his customer — I made a deposit for them to find someone. My goal was to get someone at my self-storage facility who could press one to accept payments. Very simple stuff.
They built the job description, got me three candidates, and I interviewed all three in the course of an hour. I was absolutely blown away and hired all three. Five dollars an hour, $800 a month per person — and they were incredible. Four months later I had 15 of these people working inside my company. They weren’t just doing simple stuff — they were answering sales calls, guiding logistics, doing exactly what our American reps do, except instead of paying $60–70K a year we were paying about $10K a year. Game changer.
Sam: What was the rate per hour?
Nick: Five dollars an hour, $800 a month.
Nick: So in May 2021, I went to Marshall and said, “Hey, I want to be an affiliate. Give me a cut of what I bring in and I’ll tweet.” At that time they were doing about $50K a month in revenue. I started tweeting and pissing off the woke mob and recommending Support Shepherd for a 15% cut of revenue.
Sam: What were those tweets?
Nick: I would say things like, “I’m going to weather this recession for one main reason — my employees all work for five dollars an hour in the Philippines and they’re absolutely incredible.” The woke mob would blow these threads up. We’re talking three to five million impressions. That accelerated the growth of Shepherd.
Fast-forward a year later: Shepherd had 7x’d. One year.
Sam: Just from you?
Nick: Not just because of me — they started offering folks in Colombia too, and that was a big part of the puzzle. But I went to Marshall and said, “This business is way too good. I’m not getting enough money. I want to own part of Support Shepherd.” He said, “No way, you’re just an influencer.” I said, “Well, I’ll go start another company that does exactly this — or I can be a partner of yours.” And he said, “Okay, you’re right. Let’s make a deal.”
We negotiated and I own 15% of Shepherd. The affiliate payoff was canceled. I got 15% of profits, and he just trusted me to stay motivated to keep doing what I do. Once a month I piss off the woke mob on Twitter, I send a newsletter ad, I sit on the board and do a little bit of ops, and I mostly just drive business.
Sam: Wait, I need you to redeem yourself really quick — because you’re saying “I’m pissing people off,” but the reality is these are good jobs for these folks, right?
Nick: One of my reps was talking the other day and she said, “Nick, I bought a house.” I said, “What are you talking about?” She said, “Yeah, it’s a three-bedroom house in the Philippines.” Me and my partner Dan talk all the time — our employees in Colombia and the Philippines are just as wealthy relative to their peers as we are. They used to commute two hours and work for two dollars an hour in rough conditions. Now they get to work for American companies and it changes their lives. The local mob has no idea what they’re talking about — this is an incredible opportunity for them and for us.
Sam: All right. And now?
Nick: Now it’s a multi-seven-figure profit business. I make $50K a month personally from my 15% ownership.
Sam: You would not have wanted to go start a competitor to them, would you?
Nick: I was mostly bluffing. It’s a super hard business — 150 employees, tons of great talent, sales reps, recruiting, interviewing, vetting, grading English. Marshall’s a pretty good entrepreneur. He’s done about eight companies and a few of them very well.
The Diego Clip Agency Story: Equity vs. Revenue Share [00:18:30]
Sam: I’ve had something similar happen. There’s this guy Diego — his website is ShortZy.co, I think. He kept DMing me wanting to make video clips for me. I get these DMs all the time. Nine out of ten are just really bad, but this guy kept at it and I said, “Screw it. Just make me 10 clips — send them to me.” Before the night was over he sent me 10 and they were pretty good.
I said, “I’m not going to post these. I’m going to make you post them.” I gave him my Instagram password, made him send me a picture of his driver’s license, his social security card — he lived with his girlfriend so I got hers too. And I said, “I know a lot about you. Here’s my password. Make it work.”
He kills it. I go from like a thousand followers to 10,000 in a week, then up to 50,000. I say, “You’re awesome, but here’s the deal — you’re going to do this for free for a while, and in exchange I’m going to tell all my friends about you and eventually tweet that I think you’re great.” Within a month we got him to about $20K a month.
I also do the same thing you do where I take a small cut. I’d rather have a revenue share than an equity slice. But he texted me yesterday and said, “Nick, what are your three biggest regrets?” And one of mine was not going to Marshall a year earlier and getting equity instead of a cut of profits.
Nick: Yeah, I don’t know if a clip agency is ever going to sell, though.
Sam: I love agency businesses, but sometimes they don’t need or want you involved in operations. Sometimes transactional is better. But by the way, Diego’s company is called ShortZy — ShortZy.co.
Nick: You should own 25% of his company.
Sam: Yeah, maybe I’ll end up regretting that. But we’re happy with the deal.
Nick: So what were the other two regrets?
Sam: Getting married a little earlier and having kids a little earlier — even though I did it when I was almost 30.
Nick: How old were you?
Sam: I got married at 27, had my first kid at 29. If that was three years earlier I would have been just as happy.
On Having Kids and What It Changes [00:23:30]
Nick: So many people I talk to say they wish they would have had their kids earlier, and I’m always shocked. Are you excited to be a dad at some point? I know you and Sarah have talked about it.
Sam: I’m pumped. I’m so pumped. A — I agree, I wish I would have done it earlier. And I think it’s going to be life-changing.
I was talking to Sarah about this last night. We’ve achieved a lot of interesting things at a relatively young age — professionally, financially. And parents always say “you’re never ready.” But I was thinking last night — dude, I’m totally ready. What else do I need to do? This feels like the next step.
I don’t really care about this, but I actually think it’s going to turbocharge my career. Before, I was earning for ego reasons. Then I got to the place where I make money because I do stuff that’s fun, and because of my fun hobbies the outcome is often income. I think after having kids it’s going to feel like I want something for my children, I want to impress them, I want to show them how to work hard. And it’s also going to be — I don’t want to spend all of my time working after 6pm. So I have to pick and choose my battles, and I think that’s actually going to force focus. The outcome will be better financially. Am I wrong?
Nick: You are right on the money with two things. Number one — you are going to get so much more emotionally mature when you have kids. I was highs and lows before. It just puts stress in relative form when you have a human you have to care for. The stress level when that human is sick, when they scream, when they fall and hurt themselves — it puts everything else in perspective. You just get better at dealing with stress.
The second thing is I got more focused. I could get more work done when I couldn’t travel the world or go play golf all the time or be spontaneous and fly to Europe for two weeks. Instead I would spend really good quality time with my family and then pop to my computer to tinker on the business. I was just more — does that make sense?
Sam: Yeah, it totally makes sense. And I’m pumped. We have three kids now.
Nick: Five, three, and nine months?
Sam: Yeah. I’m pumped for it. And I think the outcome will be a better career because of children — that’s my prediction.
Nick: I think you’re right.
Ari CostSeg: The Cost Segregation Business [00:28:00]
Sam: I want to talk about the cost seg business, because that seems like it’s going even better than Support Shepherd.
Nick: So cost segregation — we have engineers who go in and break out the different parts of a commercial property or income-producing real estate, and then give you a schedule of what you can depreciate faster to the IRS. Normally it’s 27 years straight-line depreciation. They take it and say, “The windows — those have a five-year life. The landscaping outside, that only has a five-year life. The ground improvements have these lives.” So you get way more depreciation upfront and save money in taxes.
Sam: I haven’t gotten my report yet, but let’s say on a million-dollar property — normally you’d depreciate, what, about $37,000 a year?
Nick: Something like that. With cost seg on a self-storage facility, you could get 20–30% depreciation in year one. An industrial property might be 10–20%. An RV park might be 60–70%, depending on how much ground improvements and landscaping you’ve done.
Sam: When do I pay that tax back?
Nick: If you sell the property before 27 years, it’s called recapture. Your taxable basis drops by the amount you depreciated, and when you sell, that gap is called recapture — you pay it at the recapture rate. So if you don’t plan to hold the property long-term, you need to keep some cash for that.
Sam: Where’s your team doing this?
Nick: My friend Mitchell Baldridge — you know his wife Mel — they’re my partners. My business partner Dan is a minority owner as well. I own 45% of Ari CostSeg. Mitchell had done 100-plus of these before we started this company and had never really thought, “Hey, we can find some engineers and do this really well.”
We created a Twitter account — @AriCostSeg — got really competitive pricing, and instead of flying somebody to your property in Texas, we do a FaceTime. You FaceTime with one of our guys and he walks around and takes screenshots.
Sam: What was that like? My property manager did it.
Nick: We have people in Miami, Colombia, the Philippines. We’ve hired seven people through Support Shepherd for this company. We have 23 employees. Mitchell’s wife Mel spent eight years at KPMG as a management consultant — she’s the CEO of the company.
We’re nine months old and we did $250,000 of revenue last month.
Sam: That’s crazy. My property is big — like 20 acres, a 4,000 square foot house, a barn with a gym — and she spent maybe 20–30 minutes walking around while this guy on FaceTime was like, “What’s that thing?” “That’s our water purifying system.” “All right, let me see that. Show me the windows. How many garage doors?” He had a checklist but also just kept spotting things.
Nick: There’s one other company in the space called Madison SPEC. They’ll fly someone out to your property and charge you twice as much because of the travel cost.
Sam: I read about this from Mark Jenny — the guy who has like a mid-eight-figure Airbnb portfolio. The Barstool guys rented one of his houses for Super Bowl week. He told me about accelerated depreciation and I started Googling how to do it, and I only found a couple firms doing it. I thought this was going to be a niche business.
How big do you think this is going to get?
Nick: I try not to make predictions because then I set expectations and get stressed. But I think we’ll do $3–5 million of revenue over the next 12 months, and over the next five years it’ll become a $10–15 million a year revenue business.
Sam: I think that’s undershooting it.
Nick: Maybe. You don’t have to set expectations, but I feel like there are so many other services you can begin to offer depending on how hard you want to work.
Sam: Yeah, we’re also launching recast.com and tax credit hunter dot com for ERC credits and employee retention credits, with the same leadership group — Mitchell and Mel. If you didn’t lay off employees during COVID and you own a small business, you can get employee retention tax credits back from the IRS. Very few entrepreneurs know about it. They expire in 2025, and it’s significant. The guys we know running companies with 150 employees are looking at $100,000 to $1 million in tax credits.
Nick: There’s a company called Main Street that does the exact same thing. Shaan either invested or knows the founder named Doug, and they were an advertiser with The Hustle. I think they raised $200–300 million. They recently laid off a ton of people — not because the business stinks, but they raised too much money and hired too many people. That’s just proof of concept. If I’m in your position, the audience is the key. The @AriCostSeg Twitter account already has 13,000 followers.
Sam: No way. What are you tweeting on there?
Nick: Just everything about cost seg, real estate investors, anonymous client examples of how much money we save people. It blows people’s minds when they realize that if you’re a real estate professional and you buy property each year and cost-seg them, you can have zero tax liability. Zero.
Sam: But becoming a real estate professional is a pain.
Nick: You need to spend — I think it’s 700 hours — and you have to be the person who spends the most time in the real estate business. You need a good CPA to log your time and build a rock-solid case. But there’s a loophole around short-term rentals right now — you don’t have to be a real estate professional, you just have to spend more time on that rental property than anybody else. Mitchell has threads on this at the @AriCostSeg account if you search “short-term rental.”
Sam: That’s sick. I think those businesses could potentially be bigger than your storage thing — and that’s just because that’s what I know.
Titan Risk: Buying an Insurance Company [00:43:00]
Nick: I’m also buying and rebranding a property and casualty insurance company. We’re calling it Titan Risk — titanrisk.com. They provide property insurance on commercial real estate: self-storage, multi-family, in case there’s a tornado, fire, or someone slips and falls.
Sam: I pay about $5–6,000 a year for my Airbnb.
Nick: We pay over $350,000 annually to insure our self-storage portfolio. And it’s a pain to work with these insurance companies — the brokerages operate like it’s 1950. My business partner Dan had to go into the top 10 brokerage firm we were working with and literally build a system for them to quickly get us quotes and bind our coverage. We can’t pay online, things move slow, nobody responds.
We found a guy in Kansas City who had really good contracts with carriers — that’s the key. He was doing about a million to a million and a half of revenue. He has four back-office people. We’re going to hire folks through Shepherd and some Americans as well, and we’re going to lean on his shop while spinning up the Titan Risk brand.
Sam: What did you pay for it?
Nick: This is in its infancy. I’ll have a lot more to share in six months. But I’m more excited about this business than I am about Ari CostSeg.
Starting a Web Development Company (Webrun) [00:46:00]
Nick: I’m also starting a front-end web development company called webrun.com — but that’s with another guy and it’ll spin up in the next month.
Sam: For the first three businesses — did you put up any capital?
Nick: We funded a checking account for Ari CostSeg. We put $50K in there, and two months later we were making distributions. That’s basically nothing to get started.
Sam: That’s crazy. Even if you hire a really good engineer for $100K, you’re only paying them $8,300 a month.
Nick: Yeah, and these aren’t easy businesses. Mel Baldridge is managing 23 people, doing a ton of sales volume, CAD drawings, breaking down properties. Marshall’s team is really hard to replicate. None of these companies are easy.
Sam: Who’s building the systems?
Nick: We’re using Airtable as a CRM. We have some cobbled-together tech, and we’re getting some web work done. Which is part of why I’m starting Webrun.
The Pest Control Acquisition [00:48:30]
Sam: What’s this pest control thing?
Nick: I have an LP — a good friend of mine who owns six branches of a pest control company. He needs capital to go buy additional companies and bolt them onto his platform. I might do a deal where I sit on the board, help them hire overseas talent through Support Shepherd and implement them inside the company, and raise the money from my real estate investors to buy the business. But that’s still in its infancy.
The Twitter Business Empire Thesis [00:50:00]
Sam: About two to six months ago, Shaan and I talked about this on the pod. On Instagram you have Rihanna and the Kardashians, who’ve built hundreds of millions or billions of dollars from their audience. On YouTube you have MrBeast. On Facebook you had BuzzFeed and others who built multi-billion dollar businesses. On Twitter, no one has really done it to the same scale. The reason might be that people haven’t taken it seriously, or that it’s only 350 million users versus billions on Instagram.
But that’s changing. What we haven’t seen yet is someone who’s built the equivalent of the Kardashians on Twitter — except instead of selling makeup, they’re selling B2B or professional services to a higher-end buyer. You might be one of the first. You almost already have. Do you think that’s accurate?
Nick: I think these companies are so in their infancy. It’s really easy to get to $250K of revenue, but ask guys like Andrew Wilkinson how hard it is to go from $250K a month to $250 million a year. Those types of jumps are on another level entirely. I don’t know if I have what it takes to do things like that. But give it 10 or 15 years to mature — I don’t know.
Sam: You’re not doing it the way they’re doing it, though. You’re kind of like the Ryan Reynolds of Twitter. He’s got Mint Mobile, the soccer team, the gin — he’s not operating those companies. Conor McGregor’s not operating the whiskey thing. But if you have 10 to 20% of a handful of things, one of them could hit.
There’s this guy named Felix Dennis — have you read the book “How to Get Rich”?
Nick: I love that book. I recommend it to everyone.
Sam: Horribly titled, best book. His bulk wealth came from owning 10–20% of Micro Warehouse, which went public for multi-billions. He had the same setup — “I own the magazines where I’ll promote you for free, and I’ll be a co-founder and advisor, but I’m not running the day-to-day.” I don’t see why you couldn’t do that with a few more things.
Nick: The power of blowing up a brand is one thing. The power of spotting and hiring and delegating to really good operators is another — and that’s underrated. That’s something I think I’m good at. I can find people who really think about business the right way. I can’t operate these companies — I’m an investor, an advisor, I pump their stuff on Twitter, I’m a customer, I help. But you’ve got to find somebody who’s really good at running a company.
Sam: I’ve been doing angel investing so I can see how founders think, how they make decisions, how they write their updates, how they fight through problems. You can just tell when somebody’s different. When somebody’s really got it.
Nick: Austin Reef is an amazing operator. I remember the first time I met him — I was probably 29 or 30, he’s four years younger than me — and I remember telling him, “I’m a lot better than you at a few things. You are so much better than me at a few other things.” The way he thinks about business problems, the way he paints a story in a clear and concise way — that’s the 10x operator. And Andrew Wilkinson’s a great friend of mine. I don’t know what his empire’s worth — somewhere in the $500 million to a billion range. When I talk to him I don’t feel outmatched. You were just bolder and smarter than me to believe it could actually become a thing, and you did it for years and didn’t give up and always did it your way.
Sam: He understands leverage and delegation unlike anybody I’ve ever met. His brain is so good at analyzing the pros and cons of a bet. He does business like a poker player — when the odds are in his favor, he goes big. And he’s an undercover killer. He comes off really humble, but the dude is definitely a killer.
Nick: He always dresses really nice, slick-back hair, designer look. I always tease him like, “Quit acting like you’re not a killer.”
Nick’s Personal Finances and Liquidity [00:58:30]
Sam: What do you invest in for yourself?
Nick: Real estate — and I’m not that liquid. I personally guarantee $50 million-plus of debt and I only have $3.6 million liquid. It would be foolish to start spending that on houses, cars, and boats. So I keep about a million in cash, another $2.5 million in public equities.
Sam: Are you trading or just buying and holding?
Nick: I’m way too dumb to try to guess what’s going to happen in these stocks. I bought some dumb stocks early on — our friend Austin Reef had a thesis on Zillow, we bought in at $150, it went to $200, he was texting that we were going, and then it went to $30. But now — Google, Facebook, Microsoft, Apple, all the best companies in the world all got 50% cheaper, so I bought a lot of those and I’m going to hold them for five years. I’m sure I’ll do fine.
What Motivates Nick Now [01:01:00]
Sam: What’s motivating you right now?
Nick: I just think it’s fun. The building is really fun.
Sam: I want to talk about you too, Sam — how many years post-exit are you?
Nick: Wait, I was going to ask you that.
Sam: Two years. I built something, I sold it, the event happened — and when it’s over you’re like, “Oh damn. I love building. I love tinkering. I love entrepreneurship and business.”
I gave myself one year where I basically wrote the rules: I’m going to read anything that interests me — I read a lot of fiction, I don’t read business books anymore. I’m just going to search and plot and whatever interests me I’m going to pursue. Like a dog on a walk, following my nose without guilt. After about six months I was ready to roll again.
I made some irreversible decisions at my company — some culture decisions. When I started at 25 and sold around 30, I was a different person. I’m more solid on who I am now. I would have had different values going in. But anyway, I made some mistakes and basically had to sell the company to get out of the situation. I was pumped about it, but at the same time I was like — I wish I wasn’t wealthy when I started the business. I had nothing. I would have liked to own it forever, but I was very happy to get that time to relax and seek.
After about six months I was like — I need action. I need to gamble. I was watching a James Bond movie thinking, “Should I become a cop? I need to get into trouble.” It’s the uncertainty — making a decision where you don’t know what’s going to happen and then waiting to see. That’s incredibly addicting.
I love being with my friends in the group chat when it gets spicy. When I’m with my partner Joe and we’re like, “We can’t pull this off, can we? Ah, screw it, let’s go try it.” That adrenaline — that’s my version of a car chase. And it just so happens that the outcome is typically money. So that’s what I’m motivated by. The thrill.
I don’t give a damn about legacy. When people talk about legacy I’m like — I don’t care. I want to leave something for my children because I love them, but I don’t care what everyone else thinks. I just want to have fun and excitement in the moment.
Nick: These calculated bets — you put the money in and you just never know what’s going to happen when you try to sell, when you start to get customers, when you start to solve problems. It’s addicting for sure.
On Decision-Making, Insecurity, and Getting in the Game [01:07:00]
Sam: I’ve been thinking about what holds people back — the fear of failure, the insecurity. I have insecurity, and it holds me back from making big decisions. The problem is, the more insecure you are, the fewer decisions you make. And decision-making is something you have to practice to get really good at. If you don’t make decisions with a lot on the line, you’re never going to get better at it. Then you have unmade decisions, and that equals stress — because stress is a decision that hasn’t yet been made. It cycles and snowballs.
People who have insecurity and anxiety around making decisions get stressed out, and it’s a big compounding snowball. It holds people back from kicking so much ass. Every high performer I know makes a ton of decisions. They make some of them wrong. They lose some money. But they just make them, and make them, and make them, and they get better and better at it. That’s when the leverage kicks in.
My parents — when I was a kid I would sell CDs or used stuff on eBay, and I remember making mistakes and they’d say, “You can’t get a hit unless you’re in the game.” That changed my life. So now whenever I screw up I’m like — whatever. A .300 batting average in baseball is great. And in business you actually need less: try a hundred things and one works, it makes up for all 99. I always tell people, “You gotta be in the game.”
Nick: I’ve been asking high performers about this because now I have a five-year-old and I’m thinking about what I can do for my kids to help them get better at making decisions. Did your parents just let you struggle a little bit?
Sam: That’s something I’ve found is very common among entrepreneurs. A lot of parents nowadays mess up because they shelter their kids from decision-making, make the decisions for the kids, keep them from any pain. They’re going to keep them from dealing with the discomfort.
My parents would make me make the little decisions when I was a kid so that I got better at them, and then when they were bigger I wasn’t overwhelmed with fear and insecurity. I was always skateboarding and rollerblading, going to skate parks. I had a unicycle. I would try to ride it downstairs. They were like — this kid is crazy — but the only rules were: you have to wear a helmet. I was in and out of the hospital — broken fingers, stitches on my eye, broke my arm, broke my collarbone. And they were supportive.
When I left school and told them I was going to join this thing called Airbnb, they were like, “This sounds like a multi-level marketing thing.” I was like, “No — I think it’s legit. Two or three hundred people work there.” They said, “You’re going to leave school to do this?” I said, “Yeah, it’s legit.” And they said, “That sounds horrible, but we’ll see you Saturday — we’ll come help you move.”
A lot of my friends who don’t take risks — their parents were quite neurotic. Instead of saying “of course this can work,” they would default to “this will never work because of X, Y, Z” or “you can’t study abroad, Mexico is dangerous, haven’t you seen the news?” That was usually the default versus “screw it, we’ll handle it when we get there.”
Nick: Yeah. Putting your kids in a bubble — I have a five-year-old and it sucks to watch him struggle. But like, let’s say he’s riding a bike wearing a helmet and he’s about to fall off a curb and scrape his knee. If I’m watching, I’m not going to sprint over and coddle him. I’m going to let him figure that out.
And it bleeds over into everything. If an employee walks into your office with a problem and you say “get out of my way, I’m going to solve that” — that enables them. It prevents them from learning how to solve problems on their own. And it enables them to bring you more and more problems and be completely unable to get anything done without you.
Sam: Do you — you have all boys, right?
Nick: A five-year-old boy, three-year-old boy, and a ten-month-old girl.
Sam: Are you going to raise her the same way?
Nick: Oh yeah. I’m going to raise a strong, secure daughter for sure. I’m going to show her that I treat her mother with a ton of respect and that her mother should never take crap from me just because I’m a man. You mess women up in the long run if you enable or lead them to be insecure. I’m going to try to raise a really strong, confident, secure girl who knows how to struggle with grace.
Sam: Absolutely. So when she falls down on her bike, not going to run over there either?
Nick: Not going to run over there either.
Closing and Nick’s Portfolio Links [01:19:00]
Sam: Well good, dude. I’m glad you came on. I like talking to you.
By the way — we have this thing we call The Gentleman’s Agreement. We’ve been growing our YouTube subscribers — last month we grew by about 20,000. The pitch is: unlike everything else on YouTube, our content is not free. We work for you. The way you pay us back is like when you go to 7-Eleven and see the jar for Muscular Dystrophy and you take a piece of candy and leave a quarter. Except instead of a dollar, all you gotta do is click like and subscribe. It’s called The Gentleman’s Agreement because we’re not there — it’s a handshake. That pitch changed everything. We started seeing close to a thousand people a day clicking subscribe. So you have to subscribe if you’ve watched more than one video.
Nick, what’s the promo?
Nick: sweatystartup.com, boltstorage.com, supportshepherd.com, recast.com, taxcredithunter.com, webrun.com, titanrisk.com, and @sweatystartup on Twitter.
Sam: I appreciate it, man. You always bring real value.
Nick: I appreciate you too. You’ve always been incredibly supportive. I remember when I was trying to launch a little community around real estate and you got on a call when you were busy as hell, and I wasn’t that big of a deal, and you helped me set that whole thing up. The generosity, Sam — it’s awesome.
Sam: Well, maybe one day I’m going to ask to be an affiliate of your affiliate or something.
Nick: Anything you need, man. Let me know.
Sam: All right. I appreciate you. Thank you very much. That’s the pod.