Elon Needs a Hold-Me-Back Guy [00:00:00]
Shaan: He needs a hold-me-back guy. You know the hold-me-back guy? You’re in a fight and you’re like, “Hey, listen, I’m gonna go after these guys, I need you to hold me back.” So you’re not actually trying to fight — you need it to look like you’re trying to fight, and you need someone to hold you back. It’s gotta be a “if these guys weren’t holding me I would have kicked your ass” situation.
Shaan: He needs to find a hold-me-back guy. And I think Elon’s hold-me-back guy is going to be a hard sneeze. He’s one hard sneeze away from throwing out his back, you know what I’m saying?
Hampton Offsite and Sam’s Personality as an Event Guest [00:00:20]
Shaan: All right, we are live. What’s going on, dude? Amazing hoodie.
Sam: Sick hoodie, you like that?
Shaan: Hampton. Yeah, that is very nice.
Sam: I had a team offsite. We had all of our employees get together in Brooklyn, and the CEO — my CEO Jordan — organized this lovely event. He gave us all hoodies that say “Hampton” and then our city that we live in.
Shaan: You’re a stressful dude to organize an event for. I’ve never had to do it, but I’ve been a part of events where people are organizing for us, and they’re like, “Oh yeah, by the way, the venue changed and we forgot, there’s only one chair on stage,” and I’m like, “It’s cool, no problem.” And then you’re like, “What the hell?” So I would be very stressed if I had to throw an offsite where you were my core customer. Is that fair?
Sam: Yeah, that’s fair. But let me explain my reasoning. This is very business-related. Number one: I believe the way you do one little thing is the way you do everything. What that means is — once you’ve proven to me that I can trust you, I’m all in and I don’t question anything. Until then, I question everything. If there’s not a good answer, I doubt you. Once we get past that stage, I’m good.
Sam: The second reason — and we could actually talk about this for a second — the second time around, everything is so much calmer. My entire reputation, my entire net worth is not tied up into this one entity anymore, which is what many things I’ve done in the past have been. So I’m much calmer. Way more subdued this time.
How Financial Security Changes Founder Psychology [00:02:30]
Shaan: I think that’s true. Do you find yourself thinking bigger now? Like — you’ve got one win under your belt. Justin Mares said once, “You do whatever you gotta do to get your nut, and after that go for your Noble Mission.” You’ve gotten your nut. You’re financially secure. Not only are you calmer, but are you more ambitious or long-term oriented in some way?
Sam: Yes, 100%. I used to criticize founders who would sell secondary. You typically only read about it when it’s done in a bad way — a company that’s going to go bankrupt, founders took $50 million off the table, didn’t work out. The reasoning behind that I think is still great, though. You give an entrepreneur five or ten million and they’re like, “Wow, I can live a really nice life now.”
Sam: I think bigger now, definitely. I think significantly longer term — like, what does this look like in 20 or 30 years, as opposed to next quarter. And I don’t care if it fails, which is actually a good thing. I’m able to try more within it. It’s like they say, keep them keen — the less I care, the more it happens.
Shaan: The way I think about it: you see examples on both sides. Back Against The Wall, no other option — that’s when people rose to the occasion. And you also hear the other scenario: “Because I was secure I was able to play a long-term game, I was less emotionally invested in the ups and downs, I made better decisions.” You can see both examples.
Shaan: I think the reality is that success is not based on either one of those. It’s not based on how much money you had in your bank account — zero or a bunch. People tell themselves stories either way. Fundamentally, I think if a person is intrinsically driven, it doesn’t matter whether the fuel is because they’re a technologist who loves technology, or because Rachel dumped them in seventh grade. Either way, it doesn’t matter. As long as you have a driving force. And everybody’s got a “why” — there are examples of people with all kinds of chips on their shoulder.
Shaan: I think you do need to be driven. It’s just a question of by what.
Sam: Are you more calm now that you’ve had success?
Shaan: Definitely more calm. But “calm” isn’t really the word. I’m less desperate, and that has ups and downs. When I was desperate to prove myself, I worked in a really fancy office — and I slept in that office. I think one year I slept there 275 days out of 365. It was nice to sleep there, it wasn’t like sleeping under my desk on concrete, but nonetheless, I just didn’t have a life. I didn’t want to have a life. I didn’t want to care about friends and dating and other things. I cared about just making it.
Shaan: It’s not even that I was super productive all those hours. I was like, look, I’m going to throw all my hours at the problem, I will sleep here, I will wake up here. That seems more efficient. I did that for several years.
Shaan: But now that desperation has been replaced with a different asset. I lost the desperation, which was serving me — what do I have now? I operate more out of purpose. I’m actually driven toward things that have meaning even if there’s no short-term payoff.
Shaan: For example, right now I’m writing this newsletter every day. There’s no ads, no premium tier, no upsell, no business model. Why am I doing it? Because I really like writing, and more than I like writing I like finding interesting things to write about — things that scratch my curiosity. As I’m doing this thing that has no business plan, I’m seeing all these extra opportunities open up that I couldn’t have seen at the beginning. The 24-year-old me would have never been able to do this, because 24-year-old me was desperate and needed a quick payoff. Now I don’t, so I’m able to do things differently.
Internet Beef: All-In Pod and the Poker Challenge [00:08:00]
Shaan: Can we talk about — is there a new chip on your shoulder? There’s been a very public internet feud going on.
Sam: No, no, but my wife is not aware of it. She’s like, “How come you’re looking at your phone an extra 30 seconds longer?” — it’s because I’m coming up with a badass slam in my head. I’m word-smithing a seventh-grade insult right now. “Hold on Daddy’s busy, I’m coming up with a yo-mama joke to Jason Calacanis right now.”
Shaan: For background: there’s a podcast called the All-In Pod. They’re great, I think they’re good, but they’re different than us. A lot of people listen to both, so there’s some competition there, but we can all win. Last podcast, Shaan challenged them to a $100,000 poker bet — heads-up poker. I shared that on the internet, and Jason Calacanis came back at me. He said, “Sam, you’re great. Shaan, you’ll still learn.” He gave me a head pat. He said something like, “Smart of Shaan to punch up” — or something to that effect.
Sam: So the background is: we were making fun of him a little bit because in the Rogan debate thing, someone had raised $2 million for a scientist to come debate this guy — a famous internet challenge — and Calacanis was like, “I’m in for 10K,” which is funny because the ante was 100K plus. I’ve never made fun of Jason. If it comes down to it, you have my loyalty — I’ll die for you — but I’ve stayed mostly neutral. This is a you thing.
Shaan: Yeah, that’s fine. And I like Jason, for the record. I have nothing against Jason Calacanis. I listened to This Week in Startups for a long time back in the day. I like the All-In podcast. It’s sort of like two thoughts that are both true: I like their content, I have nothing against them personally, I’ve met them a couple of times in passing. No ill will.
Shaan: Also, I think some things he says are funny and cringey — funny in a laugh-at-you, not with-you way. Like when the joke I made that he didn’t like: I said All-In is billionaires talking about billionaire stuff, MFM is millionaires talking about millionaire stuff. And somebody goes, “Actually it’s more like three billionaires and their friend Jason Calacanis.” He came in to defend himself and said, “Actually I’m a centimillionaire.” I just thought that was cringe, which objectively and scientifically it is.
Shaan: My poker challenge to them is only for fun. I just think it would be a fun thing to do. I love playing poker, they say they’re great at poker, so let’s do a little celebrity challenge. Nothing’s been settled, we’re not doing it yet.
Sam: They didn’t take the bait?
Shaan: He was sort of like, “Well, you’re not famous enough for me to do this. I have more to lose than I have to gain.” Which honestly — fair point. The problem with that is it’s not entirely true. You could argue they’re more popular, but there’s a ballpark. I’m in the stadium. It’s not like calling a 5’10” guy tiny. You gotta be at least 5’6” to get that nickname.
Sam: Not small enough.
Shaan: But the funny thing is, as I was talking about it on the podcast I was joking — “Wait, is this fake internet beef?” I would love fake internet beef. This is how rappers for generations have gotten famous. They just have fake beef. We should do this as podcasters. So that was the fun behind it.
Shaan: We got one-upped big time, though. Just when I thought me and Jason Calacanis were getting some fake internet beef going, Palmer Luckey — founder of Oculus — comes off the top rope and body-slams Jason. People loved that. And then while that’s going on, Elon Musk challenges Mark Zuckerberg to a fight. And now I don’t even care about my own poker match. I need to see these guys fight.
Elon vs. Zuck: Breaking Down the Cage Match [00:13:00]
Shaan: Let’s break this down. We have to do this story. So basically — do you know how it started?
Sam: I’ll fill in when you get to the Facebook response.
Shaan: The origin, I think, was a presentation that leaked out of Facebook talking about a Twitter competitor they’re building. I think it’s called Project 92 or something. Their pitch was: it’s a Twitter competitor, Instagram users will immediately have their following on it, and it will be run “in a sane way” — something like that. Basically implying that Twitter is sort of insane and Elon’s running it recklessly.
Shaan: That internal presentation leaked — maybe intentionally, maybe not. So Elon started making fun of Zuckerberg, tweeting stuff like “Zuck my bling,” just clowning on him. Then somebody was like, “Watch out — Zuck’s been training.” And Elon replies: “I’ll fight Zuck in a cage match.”
Shaan: So Zuck screenshots it and posts it on his Instagram story with the caption “Send me location” — which, for those who don’t know, is an iconic UFC moment from Khabib. When he was in the buildup with Conor McGregor and McGregor was like, “He’s scared, he doesn’t want to fight me,” Khabib just goes, “Brother, I’m not scared. You want to fight me? Just send me location.”
Shaan: So Zuck hits Elon with the “send me location,” and this triggers a chain of events. I thought it was a joke at first. I’d never seen Zuck talk trash — that was already an amazing moment, he did a heel turn. Second, I was like, okay, there’s no way this is serious. Then Elon sees that story and goes, “I’m serious, I’ll do it if he’s down.”
Shaan: And then — Sam, did you see this? Dana White’s involved. Dana White, the president of the UFC, comes out and says: “I talked to Mark and Elon last night. Both guys are absolutely dead serious about this. This would be the biggest fight of all time. Floyd and Conor was one of the biggest fights of all time — this would triple it. There is no limit on how much this could make.” He said it would be in Las Vegas, pay-per-view, around a hundred bucks. You’d have 51-year-old Elon Musk against, I don’t know, 39-year-old Mark Zuckerberg, who’s a hundred pounds lighter.
Shaan: Is this real?
Sam: The Verge reached out to Facebook and a Facebook official replied. They just said, “The story speaks for itself.” Which is basically — you know that guy in the UFC who always says “It is what it is”? That’s exactly what Facebook said. It sounds serious. And I thought that was a pretty baller move.
Shaan: I think this is hilarious. I think this is awesome. I love a freak show. Sign me up.
Sam: All right, rapid-fire questions. Topic one: do you believe this will happen? Yes or no, and why?
Shaan: I believe Zuck will do it. I think Zuck would do it. I don’t think there’s any chance Elon does it. I think Elon would get very hurt just training for it.
Sam: So you think it’s a no?
Shaan: If I had to guess, I’d say it doesn’t happen because Elon realizes he’s going to lose — badly. He’s gonna get tapped out. His cool factor is really high and he can’t afford the optics of losing to Zuck. He needs a wiggle-out. He needs the hold-me-back guy.
Sam: You’re a hold-me-back guy. You’re in a fight and you’re like, “Hey, I’m gonna go after these guys, I need you to hold me back.” It’s gotta be a “if these guys weren’t holding me I would have kicked your ass” situation.
Shaan: He needs to find a hold-me-back guy. And I think Elon’s hold-me-back guy is going to be a hard sneeze. He’s one hard sneeze away from throwing out his back. A charley horse away from quitting.
Sam: Winner by TKO — Mark Zuckerberg.
Shaan: Second question: let’s say our dreams come true, the fight actually happens. What do you think goes down?
Sam: So I box for fun, I spar. What I’ve learned is it doesn’t really matter how in shape you are or how tough you are if you don’t practice the skill set and you go against another person who has. It’s just light years apart in terms of being comfortable getting hit.
Sam: I think Zuck would finish him within two minutes. He’d probably get him on the ground and Elon would tap from getting his arm wrenched.
Shaan: Now the counterargument: you’re counting Elon out? This guy has proven he can do anything. He could train.
Sam: He won’t. I don’t think he’ll train, and I don’t think any amount of training makes an overweight 51-year-old competitive. OIC — he’s already on OIC, he’s already lost like 30 pounds — doesn’t matter. Zuck is still 38 or 39.
Shaan: Some extra data — people on Twitter were like, “Elon, we love you, but Zuck would handle you.” Here’s what Elon said. Three things: one, “I don’t work out except for sometimes when I pick my kids up and throw them in the air.” He doesn’t exercise. Forget about fighting — the guy doesn’t exercise. Two, “I’m so much bigger than him.” Elon is 6’3”, 200-plus pounds. Zuck is probably 5’9”, 5’10” max, easily giving up 50 pounds.
Shaan: And then Elon’s master strategy: he says he has a move called The Walrus. “I just lay on them, they can’t do anything, they’re just pinned.”
Sam: None of that matters. You know what Jiu-Jitsu people want? They want to start on their back with you on top of them. It doesn’t matter.
Shaan: I’m not a Jiu-Jitsu practitioner, but I’ve watched enough to feel confident in this call. You could go to a Jiu-Jitsu gym for six months and you’ll still get your ass whooped by someone who was just one year ahead of you. The learning curve is very steep. Boxing I don’t think would be a factor. The fight goes to the ground. Both guys are too uncoordinated. Nobody knocks anyone out. And it ends with Zuck tapping Elon out.
Sam: You see this picture I put in the doc? Elon wrestling a sumo wrestler.
Shaan: Yeah. He said he’s briefly done karate, briefly done judo, and a little bit of Jiu-Jitsu.
Sam: If I had to bet on Elon versus Mark on most things, I’d choose Zuckerberg. Whether business or fighting. I think Zuck would be a better hang, I think Zuck would trump him in just about everything. Don’t you agree?
Shaan: On “better hang” — I think a lot of people would pick Elon. They think he’s looser and more fun. He smoked weed with Joe Rogan, so he must be awesome. I think he would actually be an awkward hang. Very uncomfortable.
Sam: Look, they’re both podium finishers in the awkward Olympics. Let’s be real.
Shaan: Zuck literally reads books on where to place his hands when he meets people. He actually studies it. But yeah, I think Zuck wins in every aspect.
Shaan: I really hope this happens. The Dana White thing gave me a slight hope. But Dana White is, famously, a world-class liar. If you go into the UFC communities on Reddit, one of the most famous taglines is “Don’t believe his lies.” He’s a promoter. He will drum up interest any way he can.
Shaan: This might also be the Hail Mary save-Twitter thing. Mayweather-McGregor did like $500 million. If this triples that, and Elon takes home whatever portion of a billion dollars — hey, that’s just another few months of runway for Twitter, which is currently unprofitable.
Sam: I also have to imagine there’s a life insurance policy these guys have. Like, they’d have to have security with them, they can’t just — you know what billionaires do? They’ll send in a proxy. “Here’s my bodyguard versus yours.” Isn’t that how conquerors fought in history? They didn’t fight themselves, they sent their best gladiator. The top engineer at Facebook versus the top engineer at Tesla.
Shaan: I would still bet on anything Zuck does.
Beehive: The Newsletter Platform Shaan Invested In [00:23:00]
Sam: Can we talk about Beehiiv?
Shaan: Yeah, let’s do it. Tell me the background.
Sam: What is Beehiiv? Beehiiv is a piece of software for creating an email newsletter. In my opinion, it’s the best way to do it. I’m biased because I invested in it, but I also used it before I invested. We used it for Milk Road, built our whole business off it.
Sam: When I asked you what to use for a newsletter, you said, “Well, you care about deliverability, you care about how easy it is for your writers to write, you care about a referral program, here are five tools — it’s complicated and it’s expensive.” What Beehiiv did instead was different. The founder worked at Morning Brew and built out their referral and growth program. He left and basically asked: how do I productize the internal tech we had at Morning Brew so that anyone can create a newsletter brand?
Sam: This was a constant discussion at The Hustle, and my constant answer was: no, let’s just focus on the one thing. I made the right decision because it’s incredibly challenging for a media company to be a software company, and vice versa. I had ad sales people — you can’t cross-train them to sell software. But he has proven me wrong. I predicted there wasn’t a market. I haven’t been totally proven wrong yet, but so far it seems like I was.
Sam: So he creates Beehiiv. You click a few buttons, you’ve got a newsletter, templates, segments, all the features. Great. We used it for Milk Road, built our whole business off it, sold Milk Road after about a year.
Sam: Along the way I got pitched by him — probably when you did too. He was like, “Hey, I’m thinking about this Beehiiv thing, we’re raising money, big fans of you guys.” I had the same opinion as you — I don’t know, seems small. There might be some big newsletter brands, but I don’t know if the underlying software is going to be that big a platform.
Sam: So we passed. I think the first valuation we looked at was maybe $10 million-ish.
Shaan: Yeah, I passed at that time too, for the same reason — market might be too small. And I thought it can’t work at a venture scale.
Sam: Classic lesson here: there’s such a thing as knowing too much. The people who know the most about an industry are either scarred — they just don’t want to be involved with it anymore, left a piece of their soul over there — or they’re too defined by how things are and can’t see where it’s going. This is why very few breakthrough innovations come from traditional industry experts. They come from beginners with a fresh perspective, not limited by prevailing wisdom.
Sam: So we passed, but I kept using it as a customer. And at first it was good, but I kept running into limitations. I’d be like, “Oh my God, you can’t filter by X, you don’t have this analytics for my growth side, the referral program only does this” — because we were one of their first users.
Sam: His reply was the perfect startup founder reply. He’d say: “I hear you, we agree, already working on it, but let me see if I can get you something a little sooner. We’re planning to release this in two months, but let me see what I can do.” And then he would manually create a workaround. “We don’t have the analytics thing yet, but here’s what I’m going to do — I put a button on your dashboard, it’s ugly, it’s gray, nobody else can see it, but it’s an export. It’ll email you a CSV. Can you run the analytics yourself for now until we build it?”
Sam: He’d take three hours and just make your life better. He’d ask a bunch of questions like, “What are you really trying to do here? Let me confirm I understand.” Good product person, understanding actual needs.
Sam: And then — I told Ben many times, “Startups say they’ll ship in two weeks, no way.” No engineer ever hits a timeline. But sure enough, two weeks later, he would proactively reach out: “Hey, the feature’s out, test it, I think it’ll work for you guys.” And he did that three times.
Sam: Over the course of three or four months I was like, “Changed my mind. Call Tyler, we need to invest.” Tyler said, “But what about your concerns about the market?” I said, “I don’t know, might still be true. But here’s what I do know: this guy is an animal, making a product that’s really good. The market might be bigger than you think” — like private black town cars on demand, or crashing on someone’s house as an Airbnb. These things can become a lot bigger than you initially squint at.
Shaan: I’ve heard so many people say the same thing about him. I follow him online, I’ve only talked to him once or twice, but I noticed him moving quickly, changing the product quickly. And whenever I saw that I thought, “Damn, he’s gonna do it. I don’t know how big, but something’s gonna get pulled off here.” You can tell that right away.
Sam: Two things on this. One is a framework from my very first startup, in the restaurant industry. There’s this weird phenomenon: provide what’s expected — no points. Mess up their order — minus ten points. But fix the mess up — plus five points. So if you had just given them the right dish, they don’t care, just move on. Mess up their order, they’re angry. But if you fast-fix it — not just fix the order, but give them a freebie, really make sure they’re all good, take it off the bill — all of a sudden they had a tremendous experience. They’ll tell their friends.
Sam: I called it the Fix-It Theory. Mistakes are going to happen anyway, and what you need to train instead of mistake minimization is: how fast and thoroughly can you fix it? Because that is what creates die-hard fans.
Shaan: He was doing that with software.
Sam: I’ll give you one other Beehiiv story — a little dark, maybe he doesn’t want me to share it. At some point the CTO passed away. And I was being a jerk — he had said two weeks, something didn’t happen, and I was like, “Come on, you said whatever, where’s that feature, don’t you understand how important this is?” — not in those words, but playing it up that way. He says, “I’m so sorry, we’re just dealing with something right now.” His co-founder had passed away during the startup.
Shaan: That’s a very hard thing for any entrepreneur to deal with. He handled it as well as a human being can. He was gracious and empathetic around what was going on, but also understood he’s got to keep moving forward. All kinds of crazy stuff you don’t even think about — you just don’t know the passwords to half the things.
Sam: Seeing how somebody overcomes adversity in really tough situations reveals character. And you see that, you think, “They’re going to figure things out.”
Shaan: He’s really young, too, right? Like 27?
Sam: Yeah, pretty baby-faced.
Beehiiv’s Series A and Growth Metrics [00:33:00]
Shaan: The reason we’re talking about it today is: yesterday they announced a raise. Twelve and a half million dollar Series A from Lightspeed. I think at a $50 million valuation, maybe a little more.
Sam: He posted a graph of their ARR. Hockey stick curve. Three million in ARR, looks like roughly 12 to 18 months maybe. Run rate is actually at four million right now, and he said they’re trying to end the year at 12 million. So going from four to twelve — that’s what he’s gunning for. Super impressive.
Shaan: He got a call-out in the TechCrunch article — “Used by Milk Road.”
Sam: Hell yeah. I’m in the ballpark, baby.
Shaan: So where does this go? I’m an investor, but I could totally see this still going one of two ways. This might be a great business that wasn’t quite venture scale — he gets to 25 million in revenue and sells for $200 million. That’s probably the expected outcome, honestly.
Sam: Would you be happy with that?
Shaan: I’d be happy for them. We’d make some money. It wouldn’t be the kind of return you’re looking for in a startup portfolio — you want billion-dollar-plus outcomes — but a win’s a win. That’s life-changing money for them. Great outcome.
Shaan: The question is: how big does the newsletter-media thing get? If they’re at four million trying to get to ten, and they ten-x from there over the next five years — that’s a billion-dollar company. Can it get there?
Sam: I don’t think that happens. If I had to bet, I think there’s a nine-figure exit that will make them wealthy and be a huge success. I don’t think a billion-dollar company is in the cards. Too challenging.
Sam: Look at ConvertKit. If you Google “ConvertKit Baremetrics” you can see all their revenue and churn. They’ve been doing it for eight or nine years — more focused on small businesses than Beehiiv, which is more freelancers turned one-man or two-man companies. And ConvertKit’s MRR right now is basically $3 million a month, so about $36 million a year. Churn is around 3.5% a month. And it just seems very challenging to get to $100 million in revenue in a venture time frame.
Shaan: Three and a half percent churn per month is not great, but it’s not bleeding either, by SaaS metrics.
Sam: And honestly, I’d rather be Nathan Barry and own 90% of that company. Of course Nathan had income coming in that allowed him to do it. As I said — everyone’s got to get their nut and get it how they can.
Shaan: The takeaway for me, for you, and for the listener: the speed of shipping, the speed of iteration, and more than anything — talking to your customer constantly. Asking not “what do you want?” but “why?” and then coming up with the solution. The Fix-It Framework is really, really good.
The “Animal” Framework for Evaluating Founders [00:39:00]
Sam: That’s what I call it. Let me give you two other frameworks on this.
Shaan: One is from Paul Graham. He wrote an essay where he said: one of the things most commonly linked with success in entrepreneurs — and he saw a thousand-plus come through YC — is whether you can describe the person as an animal. Not like, “Oh, he’s a giraffe, long neck.” Just: “Dude, that guy’s an animal.” It just describes the tenacity, intensity, and speed with which somebody moves and figures things out, breaks through obstacles, pushes through plateaus.
Shaan: That one piece of investing advice has really stuck with me. It’s easy to get analytical about the market, the product, the industry, the competitors — and you should. But whenever I can describe someone as an animal, I make a bet. Because that type of person figures things out. On balance, it’s a higher predictor of outside success.
Shaan: The opposite is also true. I’ve made mistakes investing when I’m in love with the market and the product, and I’m kind of projecting: “If somebody was just a beast and took this on, they’d crush it.” And I overlook the fact that the person actually going after it is soft and timid, doesn’t know their numbers when I ask, wonders about stuff for weeks without clarity, gets overwhelmed easily. I’ve talked myself into market investments and it didn’t work. For early stage investing, the “animal” test is just very important.
Investor Updates: The Anatomy of a Good One [00:43:30]
Shaan: I got an update from a company I invested in. They were talking about their new LinkedIn content series — that was the main thing. It’s a software company. I was like, “Okay, but how about revenue, profit, growth rate?” I don’t care. I also don’t care about the new hires.
Sam: I’m gonna talk about my own portfolio. I said to my investment partner Roman, “Maybe 15%, best case 20% of our portfolio writes good updates.” That makes me worried.
Shaan: There’s two buckets. People who don’t write updates at all, or inconsistent ones — they pop up when things are good or when they need something, then disappear for nine months when things are tough. Paul Graham has written about this too: when you stop talking is when things go bad. The people who survive are the ones who stay in communication even when things are tough. When you omit information — like you tell me your burn rate but not your cash balance — that’s a tell.
Shaan: We invested in one company early on that was pretty famous in Silicon Valley for a while, then people went sour on it. When it was really hot, they’d write very surface-level updates: “We hired this VP and this person and this person, we brought on this new investor.” Cool. But what about the business? How’s the business going? You almost got the feeling of “don’t ask about the business.” And sure enough, 18 months later: layoffs, bad press articles, “we need to raise money and it’s not looking good.” What’s your burn rate? “Oh, we burned $3 million a month.” Dude. Why haven’t you been saying this?
Shaan: And if you ask what the problem is: “The problem is the funding market right now.” No. The problem was you were burning $3 million a month for a long period without corresponding growth. That’s the honest lesson.
Sam: I might actually just release a template for all of our portfolio companies on this. Here’s the anatomy of a good update:
Sam: Start with: “As a reminder, we are Hampton, and what we do is this.” Not because investors forget, but you’re not top of mind for people. You want a really clear punchy thing you’re drilling in — “whenever you think of this word, think of us.”
Sam: Then say “Last month was X” — good or bad, answer that question. Then write your KPIs: revenue, active users or active usage, active customers, the churn or cost numbers associated with that, net burn, cash balance, how much runway you have. And not just the number — write how much it’s up month-over-month and how you’re doing against your own goals. “Our annual goal is $10 million in revenue. To hit that we need to be doing X. We are either above, below, or on track.”
Sam: That’s the honest way to start. Below that, you can write what happened and why. “Revenue is down because of blank.” “Revenue is up because we tried this affiliate thing and it’s working, we’re doubling down.” After that, your ask: here’s what I need from you. And below that, whatever other updates you want.
Sam: What you don’t want is: “Hey, a quick update. Good month for us! We made four new hires, I want to welcome Steve” — Steve, who used to work at Visa, now he’s here, great, that’s wonderful, blah blah blah. And then: “On the product side we released these updates.” That’s where you put patch notes? Your investors don’t care.
Shaan: When I see that I think you’re lying about something. This goes back to what I said — the way you do one thing is the way you do everything. If you’re not honest about this, I think you’re not honest about other things.
Sam: I think you’re right. I used to do this at The Hustle. I felt — and I think you used to get my updates — they were in exactly this format. I understood that people basically want to get rich, get laid, and have power. Most of what people want in life is rooted in those three things. And the problem with a lot of Silicon Valley companies is they think “but I learned a lot” is a good enough answer. No, man. You took my hard-earned money. I expect a return. Scott Belsky told me — he said, “You need to be a steward of capital.” And I was like, “Oh man, that sounds official, I sound like a knight deploying resources.”
Sam: But basically: I’m a small business owner trying to make money, and my business is investing in your company. You just took money out of my family’s pockets. If you’re not doing everything you can to give me a return, I get pissed. If you work really hard and fail, or make errors, I’m cool — I knew I was playing the lottery. But if you do soft stuff and aren’t honest about it, it kills me.
Shaan: I think if they’re lying to anyone, they’re lying to themselves. It’s usually lying by omission. Either you know the situation and don’t want to say it, you just don’t know the situation (which is really bad), or you intentionally withhold the information to misrepresent. None of those have a good explanation.
Sam: The only good explanation I’ll accept is the rare company that’s doing so phenomenally well they’re worried about a leaky bucket — they don’t want the rumor mill to get ahead. But out of a hundred, that’s one.
Sam: Let me tell you — that happened to me. The Hustle was supposed to close on, let’s say, February 5th. That’s also when the acquirer’s earnings call was scheduled — a big deal legally, SEC implications. If I told someone and they made a big trade on that information, that’s insider trading. You go to jail. So I only told a small number of people who were guiding me and who needed to sign paperwork. I explicitly said, “Don’t tell anyone. This could ruin the deal.” And on February 4th — the day before we’re supposed to announce — I get an email from a reporter. I think her name was Sarah Fisher. She goes, “I have a source saying you guys are selling.” And she knew details of the deal I was like, how on earth do you know this?
Sam: And it freaked me out. We weren’t a big company. I don’t know why this should be gossip. It didn’t ruin the deal, but it drove me crazy.
Sam: To this day I hold a grudge against all three of the people I suspect. Just as preventative measures. I check up on them constantly. I want them to know I see them. They’re like, “Sam always keeps tabs on me. What a great guy.” Oh, I’m looking. A lot. I have a feeling who it was.
Black Rifle Coffee Company Origin Story [00:54:00]
Sam: Can you tell me about this Black Rifle story? I have a little bit of information about them too.
Shaan: So a few episodes ago we talked about Black Rifle Coffee. For anyone who doesn’t know: it’s a coffee brand with a very American, patriotic vibe. The customers are mostly middle America or Southern, probably right of center. Started by veterans — I think three or four of the founders were former military, Marines, something like that. And they’re Hampton members, by the way.
Sam: Oh, there you go.
Shaan: So they started this brand, and it became a really popular brand. Not only do they sell a lot of coffee, they sold enough to go public. Let me see — the stock as of whenever it was said, three or four billion dollar market cap. Current market cap is actually about 1.1 billion. So they built a billion-dollar DTC consumer brand.
Sam: Do you know how they started? One of the owners had a bunch of Facebook pages — like 30 Facebook pages ranging from “stuff for moms” to “veterans” — and he started selling a ton of stuff. He looked at all the stuff they were selling and was like, “Damn, we should make our own thing.” And that’s how the coffee business started, I believe.
Shaan: I did a call with one of the guys — Richard. He told me something slightly different. He said he wanted to be an actor, went to Hollywood, it wasn’t really working out. He teaches himself to code, starts making iPhone apps really early in the App Store, does pretty well with that, ends up getting hired by Verizon or somewhere to do marketing. Along the way he starts doing YouTube fairly early on — both for the brand and for himself personally. Builds up a pretty big YouTube following.
Shaan: Then him and his buddies start trying out different products. They’re like, let’s try t-shirts, let’s try hats, let’s try this and that. Coffee was one of them, and the coffee took off. That’s how they rallied around Black Rifle Coffee.
Shaan: To this day I think they do tens of millions in merch sales — not even the coffee. Just the merchandise. There are t-shirt companies whose entire business is doing tens of millions. This is Black Rifle’s spin-off business. That’s how strong the brand is.
Shaan: When I was on the Zoom call with him, his background — I’ll put a picture on the YouTube channel — is just a great example of subtle branding. You’re on a Zoom call, your background and your clothes say everything about you. He’s got his camo thing, his gun, all the stuff with that same kind of American tough-guy military-veteran vibe.
Shaan: So we’re talking, he’s telling me this great story. The reason he called is: he said, “Dude, I was listening to the pod and I heard you talk about the Total Man thing.” He said, “That just hit me. I love that. I went and saw that somebody had the domain, and I bought it. I want to gift it to you. If you want to do something with it, great.”
Sam: That’s a baller move. Like when Darius bought you copy that.com for your birthday — I think that was like a $20,000 domain.
Shaan: He said what resonated was the way you and Sam talked about it — look, it’s important to me that I stand for something, I live by a code. I care about fitness. I care about being a man. And that’s important to me. And you’re right that society has really pushed this thing where if you’re trying to be a man, it’s “toxic masculinity.” It doesn’t have to be that way. You don’t have to be a jerk or rude. But why is it bad to want to be manly?
Shaan: So we got this domain. And we got a lot of grief for it. Some people were angry, and I think there was an understandable reason — when we talked about it, we brought up Andrew Tate as an extreme example of this type of content. People hate Andrew Tate so much they got blinded by rage and were like, “You guys are saying Andrew Tate’s awesome, this Total Man thing is about Andrew Tate.” No. I’m just saying — objectively, this guy is extremely popular, he’s the number-one most Googled man in America right now, and I’m asking what is the appeal.
Shaan: Part of the appeal — not the whole thing — is that he preaches: be hard, don’t be soft. Mentally be hard. Physically be fit. In your relations with people, don’t grovel, don’t keep apologizing, carry yourself like a man. And what we said was: I think the pendulum has swung too far in one direction, where a lot of people are preaching a sort of genderless identity thing where it’s not cool to be a man. And I think that’s building up a craving. So something resonated with this guy.
The Total Man Movement: Branding and Philosophy [00:62:00]
Shaan: When I mapped it out, I did a little five-minute brainstorm with Ben. I was like, what does the Total Man actually mean? I went down the path first of, what matters to me — I care about financial freedom, I care about fitness, I care about family. And I was like, “Oh, I think I just described something generic that appeals to nobody.”
Shaan: What’s the real appeal of this Total Man thing? It’s not this well-rounded stuff that appeals to everyone. And then I remembered something Sam said on the podcast. It’s gonna sound simple, it’s gonna sound dumb.
Sam: You said, “It’s important to me to be a man.” Like — what? Isn’t that obvious?
Shaan: You said that, and you go, “Yeah, it’s just important to me to be a man.” And maybe you didn’t even explain it — maybe that was the beauty.
Sam: I say it to Sarah all the time. I go, “I take care of business.” That doesn’t just mean money. I’m gonna provide — emotionally, financially, spiritually. I got you. Whatever you need, I’m here for you. I’m not gonna get too emotional. If you’re emotional, I’ll be your rock. I’ll treat you with respect. I’ll handle business.
Shaan: And I was like — I think that’s it. I don’t think it’s about this well-rounded checklist. Because that dilutes the message.
Shaan: And then there’s the thing you said that I wanted to make fun of you for, but I was also kind of jealous and fascinated. You told me, “When I like to exercise, I want to be able to either kill and eat everyone in the room, or outrun them.” You stole that from Galloway — from Scott Galloway. And you said, “Don’t you feel that way sometimes?”
Sam: No! I’ve never once looked around a room of men and thought, “I could eat and kill all these people or outrun them.” Not once.
Shaan: But when you said it, it stuck in my head. It was provocative. I wanted to make fun of you, but I was also like, “There is a negative truth in this madness.” And that’s where a real brand is built.
Shaan: That was my branding revelation doing this exercise. The Total Man brand is really simple: it’s about being a man. It’s about men who want to be a man. What does that mean? We don’t need to explain it. Someone who handles their business. In all situations, “Be a man about it.” That’s the philosophy. You can apply that to whatever situation you’re going through. Be a man about it. Take care of business.
Sam: That’s the brand, baby.
Shaan: So what do you do with it? Jesse Itzler — we’re gonna have him on soon — he’s got this cool thing where you run up this mountain a bunch of times, basically climbing Everest. An event is the obvious play, but you can go a bunch of ways.
Sam: Here’s the idea, fresh off the dome. It’s inspired by 75 Hard — which is also very Total Man. And it’s going to be called Man Month.
Shaan: What is Man Month?
Sam: Thirty days. You commit to working toward being the Total Man in a few specific ways. Here’s the thing: cold shower. Fifty push-ups right when you wake up — actually, a hundred push-ups. First thing. If you’re late, you’re 10 minutes more late. Can’t do 100 push-ups? We’ll stay here till you’re done.
Sam: So: push-ups and cold shower. That’s two. We need a third. And it’s going to be: you tell the woman in your life how you feel. Or the man. You tell someone how you feel. Could be kind, could be that you’ve been avoiding a confrontation and it’s time to have it. You got to send a message — voice memo, text, whatever — to your mom, your coworker, whoever. Every day for 30 days.
Sam: Tough conversation, tough shower, tough morning. That’s how we’re doing it.
Shaan: You gotta call it “Total” something. A total conversation, a total shower, a total morning.
Sam: I think it’s good. My own critique though: it might be a little too easy. It needs to be harder. The 75 Hard thing is pretty hard. People have to look at you and be like, “Are you nuts?”
Shaan: The cold shower, you’re onto something. That is challenging. But you need a few more hard things. Fifty push-ups if you’re fit — I can do 50 push-ups in one sitting.
Sam: The original thing I was thinking about was the Murph workout. Zuck did the Murph and I was like, “Whoa, Zuck’s kind of being a man right now.” Could I do that? I don’t think I can do 100 pull-ups.
Sam: So I started working toward it. Next morning I woke up and did my quarter-Murph. Quarter mile run, quarter of the push-ups, quarter of the pull-ups, quarter of the squats, quarter of the run. I’ll do that until it’s easy, then make it harder, keep inching it forward until I can do the full thing.
Shaan: You’re right. We need to workshop the difficulty level. It’s got to be something that other people think you’re crazy for doing. It can’t be reasonable.
Sam: You could also be a little self-serving and make it include a social media post. Get that hashtag going. But you’ve got to share the results. We’re not charging money. This isn’t a program you buy. It’s a movement. You’re either in or you’re out.
Shaan: That’s it. If you’re in, you do it. If you’re out, stay out.
Closing: Having Known Sam for 10 Years [00:73:30]
Shaan: I’ve known you for close to 10 years now. Did you ever think 10 years ago you’d be about this life?
Sam: Never.
Shaan: It feels good though, right? It feels good to be a man.
Sam: Yes. It feels good. Look — I agree. When I first moved to San Francisco, people would call me a redneck because I moved from Tennessee. I remember when I first got there, you had to interview for an apartment because they had so many applications. I went to one of these interviews — this was 2012, right after Obama — and people were asking me who I voted for in order to let me have the apartment. I had to hide a bunch of stuff about myself.
Sam: Not anymore. Things have changed, my friend. This stuff is actually a lot more popular now. If you go to San Francisco, things are a lot different. Muscles are more in than before. Fitness is more in. Hard conversations are more in. So I think it’s good you’re capitalizing on this.
Shaan: We’re not chasing trends here. This is timeless. People have been trying to be hard since the beginning of time. The only thing that turns me off is if this becomes a trend.
Sam: All right. Total Man. You’re sounding harder already.
Shaan: Do you have to wrap up? I see you looking at your phone.
Sam: By the way, I’m gonna do my Elizabeth Holmes and start talking with a deeper voice on purpose.
Shaan: Dude, people make fun of you on YouTube — they say you’ve got a high voice.
Sam: I’m thinking in my head I’ve got to talk lower too.
Shaan: Hey — I think that’s why Mike Tyson became Mike Tyson. He had to overcompensate for his voice and just turned into an absolute savage.
Sam: So you’re agreeing I have a high-pitched voice? It’s not low?
Shaan: Oh my God. That is ridiculous.
Sam: All right, that’s the pod.