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My First MillionMy First Million

My $100M Mistake + 6 Company Exit F**k Ups To Avoid (#522)

Episode 522: Shaan Puri and Sam Parr play the drinking game “Never Will I Ever,” revealing all the painful mistakes they made when selling their +$10M companies.

Shaan PurihostSam Parrhost
Nov 24, 202351mWatch on YouTube

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Transcript

  1. 0:00 – 2:30

    Intro

    1. SP

      Today, we are playing a drinking game on the podcast, and we're playing Never Will I Ever. And it's a game where we're talking about all the mistakes that we made when we were selling our company and saying, "Never will we ever make this mistake again." And if you ever wanna sell a company or you've sold a company, if you sold a company, you're gonna be able to relate to some of these mistakes, I'm sure. If you wanna someday sell your company, it's good to listen to so that you don't have to pay the same price that we did and make these mistakes. So go ahead, grab a drink. We're playing Never Will I Ever. [upbeat music] Today we are talking about how to sell a company, and in fact we're talking about how not to sell a company. These are mistakes that we made, uh, selling our company. So Sam sold The Hustle to HubSpot in a big deal, sold to a public company. Um, I've had two exits now under my belt, and I've sold one to a big company, Amazon, and one to a small group of private buyers. And every time you sell your company, you learn a bunch of lessons. But we're gonna make this fun. So if you've ever played the drinking game Never Have I Ever, we have a new drinking game for you, MFM style, right? This is Never Will I Ever, and Never Will I Ever is a game where we say, "Never will I ever do blank again," um, because we made so many mistakes. We made these mistakes so you don't have to. We died so you don't have to here. And, uh, if you listen to this, you're gonna be a lot smarter when it comes to selling your company. Sam, are you ready to play the game?

    2. SP

      What are you drinking? What's your drink?

    3. SP

      I mean, I only have a little bit left here.

    4. SP

      Green juice?

    5. SP

      But I got some greens this morning. I'm, I'm looking a little athletic and I got some greens. Not sponsored, but you know.

    6. SP

      [laughs]

    7. SP

      Send me a free box.

    8. SP

      Yeah, that'll save you 8- 80 bucks a month.

    9. SP

      [laughs]

    10. SP

      Um, dude, I have a, I have a ton of it. I drink it once in a while. It's really hard to stomach for me. Do you like... You can just drink that plain?

    11. SP

      I love it plain, and I love that it doesn't taste that great because to me, I don't want my healthy shit tasting good, right? I don't like my hot people to be funny too. I don't like when things-

    12. SP

      [laughs]

    13. SP

      ... are not supposed to go together go together, all right? Like that guy Matt Rife, the comedian? Nah.

    14. SP

      Yeah.

    15. SP

      Too good looking, I'm not watching that special. Number one on Netflix? No, thank you.

    16. SP

      Yeah, he's got it all. Well, you're pretty funny. What does that make you?

    17. SP

      [laughs] Pretty ugly. [laughs]

    18. SP

      [laughs]

    19. SP

      As the world should be. [laughs]

    20. SP

      Um, all right. What, how do we wanna go about this? We have a bunch of points here. Which one... Do you want... Let's start with the, the s- most straightforward thing.

  2. 2:30 – 7:30

    Ignoring QSBS

    1. SP

      Okay.

    2. SP

      N- uh-

    3. SP

      Go

    4. SP

      ... s- so never will I ever, you both, we both have this one, ignore QSBS.

    5. SP

      Ig- I'll drink to that, yes. Now explain when you say ignore QSBS.

    6. SP

      So-

    7. SP

      What happened here?

    8. SP

      QSBS, for those who don't know, I didn't know about it until, like, a year before I sold. My friend Jack Smith told me about it. QSBS, I'm gonna try and state the law here, but it says, so it stands for qual- qualified small business stock. QSBS protects up to 10X of your investment from long-term capital gains taxes of $10 million, or 10X your, uh, initial investment. What that means, and a lot of people only pay attention to the $10 million thing. So with QSBS, how long do you have to hold it, your stock?

    9. SP

      Five years.

    10. SP

      Is it five years?

    11. SP

      Yes.

    12. SP

      So you hold a s- a small business stock, so a privately held company that's a, a C corp, and you have to hold it for 10, or five years, and it has to be valued originally, or the assets of the company, which is the value, has to be 50 million or less. You hold it for five years, and you can save $10 million in capital gains tax-

    13. SP

      The first 10 million when you sell. So, like, let's say you sell for 10. All 10 would be tax-free for, at a federal level, and many states also honor QSBS. Not California, but many states also do. So you could walk away paying zero in taxes if you sold for $10 million, which is remarkable.

    14. SP

      Or, now here's the or part that a lot of people forget. Or you can save up to 10 times your investment, whichever is greater, the 10 times or the 10 million. Now what that means is let's say that theoretically you start as an LLC, or you don't have a, your company isn't valued, but let's say you start as an LLC and you convert to a C corp, and when you convert, you value your company, and it usually has to be done by a third party, so it has to be reasonable. You value your company. Let's say you're doing, uh, 15 million in revenue. Let's say you're doing 20 million in revenue, and you say, "Great, I think we're a $40 million company." You get a third party that does it. So you can save 10 times $40 million-

    15. SP

      Yeah

    16. SP

      ... in taxes.

    17. SP

      $400 million. That's a $400 million tax shield right there.

    18. SP

      Yes, and I know friends that are doing this. Now, this, this, this, this law, a lot of people don't know about it. It's maybe w- besides real, some of the real estate laws for tax savings and real estate, it's probably the greatest thing there is.

    19. SP

      [laughs] It w- it's better.

    20. SP

      Better. You think it's better?

    21. SP

      It's better than real estate because in real estate you have, let's say, uh, depreciation or the 1031 exchange. These are great, but they're deferrals, whereas this is not a deferral. This is simply, you just have a z- you know, you have a exclusion on 100% of your gains up to some number. So it is way better than a deferral. It's way better, uh, than real estate. I was talking to a real estate guy yesterday and I said, "I have the greatest tax thing that no real estate guy has." He go, "What are you talking about? Real estate's the most tax advantage." I said, "Yes, but you don't have QSBS 'cause real estate is not eligible for QSBS." There's only certain types of businesses can do it. But like, like Sam's saying, you could stack it. So for example, what some people do, they have QSBS for themselves, but it's per tax return. So you could do it for yourself. You can create trusts for your kids and give each of them equity, and then each trust gets a $10 million exclusion in addition to your own. So you could have, uh, you know, I was joking around with a, a QSBS guy and it's, he's like, "Yeah, if you have three kids, I can get you f- I can get you 40 million, 50 million in QSBS." And I was like, I was like, "Oh, this kid I have, you know, this next kid, uh, you know, I'm gonna have, this is, this is just a walking QSBS shield here. [laughs] Like, this is awesome." And, uh, it used to be- That it wasn't 100% exclusion

    22. SP

      But does that mean that your kid, when they're... But will your, your kids at the age of 18 have say and control over your business?

    23. SP

      When they're 18, I mean, you, you know-

    24. SP

      I think so

    25. SP

      ... have exited by them by then, right? Like, but they're gonna have-

    26. SP

      But maybe not

    27. SP

      ... but they're gonna have a, just a small equity stake. They're not gonna get the majority, right? Like, you're just giving them enough so that they have a shield. They have like, you know, they have less, less, uh, tax. And you, you know, while they're minors, you control the estate. You can always, you know, uh-

    28. SP

      Sure

    29. SP

      ... I don't know. Though I don't think what a lot of people having is like little kids that 18 years later are like Succession hostile taking over, like, the company as they band together. I don't, I don't think that's the, that's the thing to worry about. [laughs]

    30. SP

      And we'll wrap this one up by... With there's a big asterisk here, which is this, I don't like calling it a loophole, 'cause that sound like a... First of all, I hate that word loophole, 'cause loopholes are good. Loopholes are legal.

  3. 7:30 – 13:00

    Shutting down a company

    1. SP

      f- um, half. Uh, I don't know if this is gonna be in play for how much longer. Uh, this is not like real estate where it's gonna last forever.

    2. SP

      Right. Right. Yeah. And it's, but it's, it's been out for a while, um, and it's, it's amazing, e- especially in the, in the tech industry. [upbeat music]

    3. SP

      I can't find this client info.

    4. SP

      Have you heard of HubSpot? HubSpot is a CRM platform, so it shares its data across every application. Every team can stay aligned. No out-of-sync spreadsheets or dueling databases. HubSpot, grow better.

    5. SP

      All right, so my turn. Never will I ever just shut down a company without trying to sell. So-

    6. SP

      We'll drink?

    7. SP

      Yeah, have a drink for that. I, uh, before I sold, before my first exit, I had built many companies, many products before that, and they all had reached some version of like, you know, an outcome. Some really had no, no momentum. Some had like some momentum, but not breakout, and it wa- either wasn't worth our, our time or it wasn't able to get funding or whatever. I specifically remember one app that we made that was... If you remember Bitmoji, we had basically made an app that was like way better than Bitmoji. It just like w- we-

    8. SP

      And Bitmoji was giving you an, um, like a, a personal avatar

    9. SP

      ... a little character for yourself that would be in these, and then it, it would give you like kinda like these stickers that were in funny, like, positions or phrases. And we had made an app that was even better.

    10. SP

      Making the world a better place one emoji at a time.

    11. SP

      Exactly. Emojis are, emojis are one of the greatest products ever, right? Self-expression there. Um, so you, we had made an app that created a character of you, um, and then you could, and then you could type any word. You could just type hashtag whatever, uh, boogie down, and it would make your character boogie down. And we had every, like whatever you could think of, like you could put, you could say, hashtag single ladies, and it would dress your character up like Beyoncé right away doing the Single Ladies dance. Like, whatever you could think of, we would, we had, because we would just every day we would rank the top tagged terms, and our artists would create like hundreds of these per day. So very quickly we had tens of thousands of combinations. It was really fun 'cause you could just type something in just to see does it do it or not. And people did this. We got half a million people to download the app in the first month. They were just pounding like tons of these little stickers. It didn't have great longevity, but it had this like amazing novelty factor. And we were trying to do it as its own messaging app, which was too hard. Like people wanted WhatsApp, they wanted Facebook Messenger, they wanted all these things. And I wrote this blog post called My $100M Mistake. 'Cause we took that and we said, "Well, this is not really sticky as a messenger. It's not big enough where you're gonna get all your friends to switch and, and start t- texting you here. People love the character. They love these stickers. We don't wanna build a sticker company. So I guess we'll just crumble it all up and just Kobe and just throw it away." And, um-

    12. SP

      [laughs]

    13. SP

      ... that was so dumb in retrospect. What we should have done is taken that little app to all of the existing messaging companies and be like, "Hey, this feature is unbelievable. Building this is not easy. We've already built it. We've proven that people really like to do this. Look how many, like the average person is doing 60 of these. Um, you know, just buy this and put this into your keyboard." And shortly after, Bitmoji sold for $100 million to Snapchat doing exactly that 'cause they, they couldn't make it as a standalone app either. And, um, I have no idea why our instinct was just to like, just pivot, just turn it off and pivot versus like take 30 days and have like five conversations. Even if it doesn't go through, like you owe it to yourself after, you know, nine months of hard work or a year of hard work, uh, and creativity on something. So never will I ever just shut it down.

    14. SP

      You said we got 100, or sorry, we got 500,000 downloads in 60 days and had a brief moment at number one on the charts before falling into mediocrity. Uh, how much could you have sold this for?

    15. SP

      Easily tens of millions. Easily. Like, you know-

    16. SP

      You think so?

    17. SP

      ... it, it either wasn't gonna sell at all, 'cause there's only like eight buyers for this. There was like eight mes- messaging apps that were major at the time. It was like Line and Kik and, um, you know, WhatsApp and Facebook Messenger and Snapchat. There was all, you know, there was eight players that like could benefit from something like this. And either it just wasn't gonna sell at all, but like that's actually unlikely. There's a price, there's a kinda like a price for every buyer. Um, the hard part would've been our team wouldn't have wanted to go with the acquisition, and so we would've had to like either try to just sell the tech, which is really hard, or sell the whole company, including the team, and then disband for a year, then come back together. And we, uh, dis- you know, we didn't... But we, the thing is we didn't even really get to that point. Like, we should have gone and s- seen what our options were, right? Like in, in poker If you've already paid the blind, well, just see the flop. Maybe, maybe something good will come out of it. And we didn't do that.

    18. SP

      Did you... By the way, your, if you Google $100M Mistake Shaan Puri, there's, uh, you have a Medium blog. Uh, you've got a lot of good posts here, so if you're listening, go check it out. Did, did you not... And this might bring me to my, my point. Did you not sell because your main investor didn't give a shit?

    19. SP

      No. It, it literally just didn't come up. It's not like we had a conversation and one g- one side said yes and one side said no and we debated it, and then one side said, "No, I have the voting control." Hell, we didn't even think about it. We just moved o- we literally had lunch, and then we just moved on. Like, it was just-

    20. SP

      [laughs]

    21. SP

      Like, it's the worst types of mistakes. The worst types of mistakes are the ones where you didn't even really explore the possibilities. You didn't even ask yourself, "What could I do here?" You just sort of quickly glossed over it, didn't, uh, didn't even give it the thought to make a decision. It was a non-decision decision.

  4. 13:00 – 17:30

    Putting out desperate vibes

    1. SP

      That's like your third or fourth or fifth multi, like ten, multi tens of millions of dollars mistake. The first one being not joining Stripe as employee 30 or 50 or something like that, and not selling this app. And I think, I think you might have a few more.

    2. SP

      Dude, I'm, I'm Shooter McGavin in Happy Gilmore when he says, "I eat pieces of shit like you for breakfast." And then Happy Gilmore goes, "You eat pieces of shit for breakfast?"

    3. SP

      [laughs]

    4. SP

      That's me. I've, I've made mistakes more expensive than your net worth. And it's like, you've made mistakes like this? And it's like, yeah, multiple. Multiple. [laughs]

    5. SP

      Um, all right. Here, I've got one. Never will I ever act desperate. You have-

    6. SP

      Oh, man

    7. SP

      ... on here you will only have one option, that is the way that not act desperate. That is one way. But when I was building my company, I wanted an exit so badly.

    8. SP

      [laughs]

    9. SP

      Like-

    10. SP

      Give me an analogy. On the spot analogy. You wanted an exit as bad as...

    11. SP

      Like, a 12... Like, when I was 12 year, 12 years old and, like, a cute girl, like, you know, like, complimented my braces. It's like-

    12. SP

      [laughs]

    13. SP

      ... I wanna close this so badly. I'm emotionally invested. If you don't like me, no one will like me, and I'm a piece of shit.

    14. SP

      [laughs]

    15. SP

      I was so desperate. I had all of my personal, uh, net worth, my emotional net worth tied into this exit, and I acted like a little bitch.

    16. SP

      [laughs]

    17. SP

      And one of the ways not to do this is to have multiple options. That's the easiest, most, most tactical one is to have lots of options. The second one is you just don't... You, you basically have to act like a hot girl. You're like, "Look, I, I don't care."

    18. SP

      Right.

    19. SP

      Like, I'm gonna be fine regardless. And I remember there was one point. Do you track your, like, your finances somewhere?

    20. SP

      Mm-hmm.

    21. SP

      I have, like, a, a spreadsheet. And I remember one day I just added, like, 10 million... Like, you have, like, an other account, so you can link all your accounts, and I just had other. And I just manually typed in $10 million. And I would stare at that for, like, six months.

    22. SP

      [laughs]

    23. SP

      And it actually helped me believe that I already had it, and so I was a little bit less desperate. But I remember being desperate. And when you are desperate, you have zero power. And when you have zero power, that is the worst part to be in when you negotiate. And the, the best part when you can negotiate is to walk away. And the, and, or to be able to walk away. And to be able to walk away you typically just don't give a shit, so you're just, like, passionate about whatever you're doing, and you don't need the money, or you have other options. And I remember being desperate in that just, like, to that 12-year-old girl who was into me, Erin, uh, you know, like, they could sense it.

    24. SP

      [laughs]

    25. SP

      They could, they, they could smell the fer- the, the, the hormones on you. Like, anyone could... Any hot girl could tell when you're being desperate. They can tell what a confident man is like, and I was not a confident man.

    26. SP

      [laughs] Can you put your retainer back in, please?

    27. SP

      It's the same thing, right?

    28. SP

      Yeah. The, um-

    29. SP

      [laughs]

    30. SP

      You've nailed it in that last bit, which is the rules, the rules of a neg- of negotiating when you are, when you're trying to sell your company. Number one, the most important rule is you must be okay if no deal happens. Meaning not just like, "I'll, I'll be all right," like, you know, like a funeral has happened. But you mu- well, the, you know, option one should always be we do no deal and we're totally fine. I would love to keep going. And whether that's true or not-

  5. 17:30 – 22:00

    Choosing the highest offer over the best offer

    1. SP

      Right.

    2. SP

      Something. You wanna do the deal that will close. That is the best deal.

    3. SP

      That, that is one of mine as well. I put, uh, never will I ever go with the highest offer. Sounds confusing. [clears throat] Like, what do you mean? Maybe, you know, why would you not take the highest offer? You wanna take the best offer, not the highest offer. And the best offer and the highest offer have a lot of differences. One of the differences is what you just said, the likelihood to actually close. Will they do what they say they do, they say they will do? Um, I'll give you a story from the Milk Road sale. We had a high offer, and then we had a fair offer. And at first we were like, "Hell, hell yeah, we got the high offer. This is great."

    4. SP

      Did, but they, they did a bunch of weird stuff, though.

    5. SP

      There were some red flags, but hey, dude, it's like, you know, like anything else. You know, when, when something's really attractive, a red flag just starts to look just like a- It's like, is that maroon actually? Maybe that's, maybe that's orange. You know, like-

    6. SP

      [laughs]

    7. SP

      ... it's not so red. You, you start to overlook and talk yourself out of a bunch of things, right? So, like-

    8. SP

      What was one of those red flags? Can you say?

    9. SP

      [laughs] They had a lawyer that would jump on the call that refused to ever turn his camera on, had no LinkedIn. Sent us a document that was, like, the term sheet that was like... Our lawyer was like, "There's no way a lawyer wrote this." And we were like, "Okay, it's probably not good that their lawyer's not a lawyer, but, um, we don't understand also why-

    10. SP

      [laughs]

    11. SP

      ... why they would not have a lawyer." It's like, it's this guy's friend. He says he's a lawyer. So it's, like, so strange. It's like, you know, they're not, like, scammers, but it's just like, can you just turn your camera on? And, uh, you know, like, it was weird. Uh, it was just, like, a little bit weird. That was, like, one-

    12. SP

      But I think they sent you money. Didn't they s-

    13. SP

      Well-

    14. SP

      Did, you were sent money, right?

    15. SP

      We, we went down the p- we took the offer, and, um, there was a time to close. But the f- the, the, again, one of the stupid things they did, they wrote the offer as when we sign the t- the term sheet, which is not, the deal is not closed until you sign the term sheet. Uh, they wired us all the money. They had to wire us all the money on day one, which again was like, are these guys idiots? Why are they doing that? That's not how this is supposed to go. Um, but we were like, "Well, I guess we're getting money, so like, what, what do you know?" And it was during that kind of closing period that we started to get a little sketched out and said, "Look, I don't think this is the right deal for us. Maybe we should just go back to options one. We'll just keep running our company. We don't have to do this deal." So we wired back millions of dollars voluntarily because we had made the mistake of going with the highest offer first. And the best offer is a combination of it's likely to close, I'll tell you a funny story about that, um, the people involved are high quality, and they're people you wanna be around, 'cause it's not a, a sort of hit it and quit it, you're never gonna see these people again. Like, business, even if your deal is kinda like you walk away f- clear, like, I don't know, the business world is actually kinda small. You run into people. They now own your company, your brand. Like, you don't want it in the wrong hands. You'd rather do business with great people who you might do more business with in the future, um, which is what we ended up doing. So the best offer is different. Now, let me tell you a story about, [laughs] uh, about, um, likelihood to close. So we get this high offer, and we're comparing the high offer with the fair offer, and I call, uh, Balaji, and people know Balaji. You know, he's one of the smartest people on Earth. So I call Balaji, and I say, "Balaji, what would you do if you were me?" And he's like, "Well, that's a higher offer, um, but let me ask you a question. Have you..." He, of course, like, intelligent people can get to the heart of the issue right away. Like, he just, like a metal detector, just knew. And he goes, "Are you negotiating these on the ta- same timescale?" And I was like, "I don't know what that means." He's like, "Who did you talk to first, and how far along, how long have you been talking to them, and how long have you been talking to the high offer?" I said, "Well, I've talked to the fair offer way earlier. We've negotiated it, renegotiated it. They've done diligence, and the high offer is new," blah, blah, blah. He goes, "Oh, okay. So this is not the real offer." And he's like, um, "You need to apply a discount." And I said, "Well, what do you mean?" He's like, "Well, you don't know if this deal's gonna close. You don't know if this number's gonna stand. You don't know if they're gonna change their mind." He says, "This is all fresh, and a fresh deal is not the real deal." And so he's like, "You need to just mentally apply some discount factor for if this even, even is gonna be the final offer that gets sent to your bank account." And so I was like, "Okay, so like 10%?" He's like, "Tell me what you know about this person." I told him everything I know. He's like, "50%." [laughs] And so we had to cut the offer by 50% mentally to, to, to, you know, compare apples to apples, and that was some of the best advice we got was

  6. 22:00 – 27:00

    Assuming you’re talking to the decision-maker

    1. SP

      that one piece of advice. So now I always, in any deal, I have to ask myself, "What's the discount factor here?" Meaning, how likely are they to close? Um, have they done all their diligence yet? Have we already had the deal f- have we already negotiated this to a stalemate where kind of both sides feel like they've gone as far as they're willing to go? 'Cause that's when you can reduce the discount.

    2. SP

      When we were selling to HubSpot, I remember the, just like I said, the, the, my contact, the woman I was speaking with, she sensed weakness, and she sensed, uh, uh, she sensed that I was in a tough place emotionally.

    3. SP

      [laughs]

    4. SP

      And she, and I, 'cause I was constantly asking her-

    5. SP

      'Cause you were sobbing [laughs]

    6. SP

      ... "All right, what else do you need? Where, how do, h- how do we move this forward?" Yeah, she could like, she could, she's like, "Are you, are you laying down when you're talking to me?" [laughs] Like, she could just, like, sense that I was, like, laying on the floor. And, uh, and the difference between what you did and what I did was two things. One, I sold to a, a public company, which meant basically the decision-maker was not the CEO or the owner of the company. It was the person who reported to the person who reported to the person who, who reported to the person. It was, like, four, you know, ladders down, probably, the decision-maker. The CEO was probably, like, they just saw it on their, like, board meeting every once in a while.

    7. SP

      SWAT team. [laughs]

    8. SP

      Like, you know, quarterly, and they're like, "Okay, cool. Whatever. Now can we talk about important stuff?" And this woman, she was like, "Look, we don't care about you." Well, you know, she basically said, she's like, "Our company is worth, like, $20 or $30 billion, and this is a rounding error for us. Our reputation matters more than, than this little deal, and it would hurt, it would hurt our reputation more than the, than the cost of this deal in order to dick you around. If we say we're gonna do something, we're gonna do something. Now shut up and relax." That's basically, like, what she was saying to me, and I remember feeling, and I was like, "I feel so much better."

    9. SP

      [laughs]

    10. SP

      And, uh, so I think there's a difference between selling to, like, like, selling a small business to a sole proprietor or to a PE company or to a really large strategic company. I think the way that you deal with those sellers is different-

    11. SP

      Well-

    12. SP

      ... or buyers are, is different

    13. SP

      ... I'll tie that in. I have and never will I ever, never will I ever assume the person I'm talking to is the person who's buying my company. So this is when we sold to Twitch, uh, which is owned by Amazon, I'm talking to corp dev. It's very easy to think, I th- I'm assuming you're talking about somebody in corp dev?

    14. SP

      Yeah, in corp dev. She, this lady was wonderful. She was like my therapist for three months.

    15. SP

      Right. And corp dev is very helpful. They're, they're the, they're the router, they're the project manager of any acquisition. But they are not the decision-maker. And actually, the thing you described I actually think is not that true, meaning I actually do think there is a decision-maker. They are pretty high up. It's either the CEO or it's the, the VP or the SVP who runs like, you know, or somebody in the C-suite who like matters to sign off on a, on a transaction-

    16. SP

      Right

    17. SP

      ... of, of, of, you know, a multi eight figure transaction. That's not... It's actually not, uh, it, it actually, the decision actually does ladder up. But by design, these companies design it so you're never actually gonna get to talk to that person 'cause they need good cop, bad cop. They need the person whose job is it to move the transaction along or find out information, and then that person can't actually be the one who's negotiating with you. They're gonna be like, "Cool, I'll go back and find out." And that layer, those layers of bureaucracy are actually a huge negotiating advantage that a startup typically doesn't have, um, unless you're working with bankers and whatnot, where you, where you do have an intermediary that's able to do that for you. And so one of the most important things you gotta figure out is who's actually buying this company. It's not a company that buys a company. There is a person in a company who needs something for their job, and you have to figure out who is that person and what is the fire under their ass f- uh, you know, what is the thing that, you know, are they in trouble for their job and they need to do something 'cause the competitor is getting ahead? Are they super strategic and they had a dinner with somebody and they, they had an epiphany and now they're, they, they're Steve Jobs, they're a visionary, and they're trying to make that vision come true? You need to fit that story. Like, um, you know, you have to figure out who is that person in the company and what is the fire under their ass if you ever, if you wanna have a chance of being able to sell a company, 'cause you're selling to that person, that champion alone, not to a multi-billion dollar corporation.

    18. SP

      Right. And, and so the buyer really matters and understanding what motivates them. A lot of times the people in corp dev, they just wanna keep their jobs and they wanna look good. And so as the seller, you have to sell a company and you have to make them look great. You have to make it easy for them to look wonderful.

    19. SP

      You, you have such different incentives. They are just trying to not fumble the bag. You are trying to get your first bag, and you are gonna behave totally differently and you're gonna value different things. And if they ever said to me something like, "Oh, this is kind of a rounding error" or like, you know, "This is, we're huge, this is not, this is n- not a, this, you know, this is a small, small piece of it" I'd be like, "Cool. Round up. The price just went up 10 million then." Right? Like, [laughs] you know, if, if-

    20. SP

      [laughs]

    21. SP

      ... if this money don't

  7. 27:00 – 37:00

    Not getting uncomfortable in a negotiation

    1. SP

      matter to you, it matters a hell... Every dollar of this matters to me, and so maybe we have the price wrong actually then. Uh, let's get the price right before we, we continue. All right? Like, that is, um... A- a- and by the way, you saw this. Uh, we just renegotiated our deal with HubSpot, and like, you know, without going into the, you know, the guts of the details-

    2. SP

      Everything mattered

    3. SP

      ... everything mattered. And you saw how I approached that. We, me and you have very different approaches to negotiation. [laughs] What did you see or describe, describe that?

    4. SP

      So this is like a Midwestern values thing-

    5. SP

      [laughs]

    6. SP

      ... which is if, if I order a steak and you send me out a pizza, I'm just gonna shut up and eat it-

    7. SP

      [laughs]

    8. SP

      ... and I ain't gonna complain. The way that you did it-

    9. SP

      This steak tastes different. [laughs]

    10. SP

      Yeah. Yeah. I love my steak with mozzarella and, uh, pasta sauce.

    11. SP

      [laughs]

    12. SP

      This is exactly how I like it. You handled it differently, and I, and frankly I, I, I, that was, uh, one of, that was a, an example when I learned from you. I think you said something great. You said, um, "Whoever can be most uncomfortable will win." And you needled these fucking guys for everything.

    13. SP

      [laughs]

    14. SP

      And in my head I was like, "What? Why? Who gives a shit?" And you're like, "This word needs to be that." And I'm like, "What are you doing?"

    15. SP

      [laughs]

    16. SP

      And, and you were like, "It all matters. It all is really important." And frankly, you got your way, uh, at least for the big important stuff, and when you got your way, I got my way too.

    17. SP

      To get the negotiation done, both sides have to get their way, but you have to figure out what really matters to them and what really matters to us, and those two things are not gonna line up. And you need, um, like Sam Altman, uh, you know, he's, he's all in the news right now, and he said something great about negotiation. Uh, he goes, "I am not interested in binary negotiations. There's nothing interesting there." Where it's just a number and you want it to be lower and I want it to be higher, that's just a tug, that's just a tug of war. That's like, you know, that's not interesting. That's not a sport. It's like slap fighting versus MMA, right? Like, the slap league is literally just one guy standing there with no defense and one guy's gonna sma- slap him as hard as he can. It's kinda interesting to see, but like it doesn't have the same, uh, it's not as satisfying to, to, to the sophisticated barbarian like us who likes, you know, UFC instead. And so, um, the sophisticated barbarian cares about a, um, a non-zero sum negotiation. And so it's like, how do I give them what they want?

    18. SP

      What's that French word? Je ne sais quoi?

    19. SP

      [laughs]

    20. SP

      What is that? What is that, Ari? Am I saying that right?

    21. SP

      There's an art there, and so you have to figure out what are the things they really care about that I only kinda care about? What are the things I really care about that they only kinda care about? How do we all get what we want in order for this to work? Um, but you're right that I was willing to be more uncomfortable than you or maybe most people, just because, I don't know, this is our baby and this is like one line item for them, but this is like our, this is like the basis of what we do and it has, has potential to be like such an awesome part of our lives. Like, uh, you know, I have to get this right. This is my kid. It's like, you know, my kid versus, uh, you know, how my teach- how when they go to school, how a teacher's gonna teach, treat my kid. Like, they care, but not the same way I do about my baby, right? It's different. There's levels to that. And so, uh, yeah, you know, the, the party that's willing to be more uncomfortable generally will win. Or the way my dad taught me was the more stubborn person wins in any negotiation. Uh, can I tell you a, a dad negotiation story?

    22. SP

      Yeah.

    23. SP

      So I worked with my dad for about, um, nine months I think in my life, and I, I, I'm really happy-

    24. SP

      Yeah, and your dad does everything, right? He's like-

    25. SP

      Um-

    26. SP

      Like, he does projects

    27. SP

      ... he started as an, a engineer, a lowly engineer, and he has like, you know, he is like office space or like, uh, Dunder Mifflin or something. Like, he was sitting in his cubicle and it, he kept getting patents, so his wall had like 22 patents on the wall. Um, but his salary stayed the same, and he's like, "How come like, you know, this... Like, the guy who dr- dresses up nice, uh, he works for me for six months, I get this patent, he gets promoted, I stay here? Like, wait, am I in the wrong job?" So it took him 10 years to figure that out. He's like, "Maybe I should move to the business side." He works at a... He works at BP for like 30, 40 years, and he finally like leaves, and he does... Then he started doing more entrepreneurial things. One of which was, uh, we both worked together in this company in Australia. And, um, when we were working there, I got to w- see my dad in action. And like it's so funny. Like, you see your dad at home, and dads at home are just like these like totally different creatures when they're like done with work for the day. I had to see him like interacting with other people, especially for an immigrant dad, it's like, it's like, "Oh, you have this level of polish? Why at home do you turn into just like a caveman?" Um, and so I got to see him just act totally differently. And one of the s- things that happened was they, uh, we were negotiating with, uh, this other party. The other party was this slick talking Australian guy who literally ha- looked like Leonardo DiCaprio. This guy's on like, uh, the Australian CNBC every week-

    28. SP

      [laughs]

    29. SP

      ... and he's super polished, just an amazing talker. And I just think, "Oh my God, my dad's... I'm gonna have to get watch my dad get beat up in this negotiation." This guy's like Mr.-

    30. SP

      [laughs]

  8. 37:00 – 43:00

    Being disorganized

    1. SP

      And then if, you know, if it's been three years, you have to call Zenefits and be like, "I don't have access to my account anymore. Do you guys even have these records?" And I thought this was stupid, and I was like... I remember telling Kipp, the CMO of HubSpot, I was like, "Kipp, I used Fiverr one time. I paid $150 out of my PayPal account. I even paid it personally." And he's... I was like, "Why does this matter?" And he's like, "Well, you know, I can't hire BBaller84-

    2. SP

      [laughs]

    3. SP

      ... on Fiverr because that goes against Fiverr's terms of service, and that would be like, I can't... Like, I have to make sure that everything was by the book, because every little thing matters." And, and that made a lot of sense to me, but I was a fool and I was disorganized. I would use PayPal for some stuff. Every once in a while I would just Venmo someone. I'd be like, "Here's 500 bucks. Thanks for the freelance." Or I wouldn't track, uh, confidentiality agreements. It was a fucking mess. I used Google Drive to store some stuff, Dropbox to store some. It was a mess. And I'm telling you, wh- when you're selling a company for what I sold it for, I only had 40 employees, and you can't tell anyone that you're selling the company. So it was basically me and Edie, this woman who worked with me, and we went through all of these documents to find all of this shit, and it literally took three months to find documents. That's... And three months working every day for 12 hours a day. It is so hard to get all the documents. It is so challenging, and you don't wanna give them anything that's messy, otherwise you'll look not buttoned up, and if you look not buttoned up, they'll say, "What else are you missing?" Or like, "Are you lying about something?"

    4. SP

      Right.

    5. SP

      And you need to present things in a really nice, orderly fashion. And so start being organized from day one is really, really important, and not like being a maverick and being like, "I'll just... Here, I got 20 bucks. I'll pay you for this. I'll use PayPal for this." Uh, like it's a mess.

    6. SP

      Well, I gotta drink to that because I made that same mistake, no surprise. I'm like the most disorganized guy on Earth. And, uh, you know, I made mistakes like I thought, uh, you know, hey, startup, you guys gotta move fast. Don't waste time incorporating and getting trademarks and, um, doing all that. And, you know, that could be the difference between long-term capital gains or short-term gains, or having to, you know, explain why, you know, the IP is over here but it should be over here. Um, or you know, we made a mistake of, um-

    7. SP

      Did you mail in your 83 (b) ?

    8. SP

      I... One year I did, and then for one company I just didn't do it and I was like, I was like, "Oh, I gotta like go to the post office?" And I just didn't do it. Now luckily that company failed and I didn't have to pay the price of that, but like, you know, the 83 (b) election basically, but for anybody who doesn't know, is like a... You can basically get shares in a company and you can tell the IRS, "Hey, tax me now this year on the gain of these shares, um, because I'm gonna exercise them now."

    9. SP

      And it's like $100.

    10. SP

      I'm gonna exercise these shares now. Um, tax me n- you know, so it's like the, the original strike price was one cent and then they're valued at one and a half cents. And so you're like, "Tax me today on that gain so that I've exercised the shares at this price, so that when I sell y- I don't have to, uh, ha- pay this huge markup on the, on the exercise, uh, of the gain."

    11. SP

      And you only have like 30 or 60 days to mail it in, and you basically literally have to write a letter. Is it 90 days? You have to write a letter and you wanna like postmark it, and then you wanna like you, you write in the letter like, "Send me a receipt of this."

    12. SP

      Right. [laughs]

    13. SP

      It's like a really manual process. And you're like, "Dear IRS, please send me proof that you received this." And you have to store that in your records-

    14. SP

      Right

    15. SP

      ... in case you ever get audited.

    16. SP

      And I think now there's like, I think there's some automation around this, but yeah, I, I was messy about that. Uh, you know, I had this great meeting when I wanted to sell my company. I didn't know how, and I went and I met with five people who had sold com- multiple companies and I was like, "Okay, just hey, I don't know what the fuck I'm doing here. Um, can I explain to you what I'm currently doing and then you tell me what I'm doing s- that which, which parts... Point out the dumb parts, okay? Can you do that?" Uh, 'cause I was like, "If I just ask you for your advice, who knows what you'll say? But if I draw you a picture of what I'm doing and you can point to the ugly part, that'll help me." And so that's what I did. I had, uh, lunch with this guy, Fuad, and uh, he's the CEO of this company called Array now. And he had sold, I think he sold like five companies or some shit like that. And um, he pointed out two mistakes that I was making. Number one, he goes, uh, he's like, "Oh wow, you got like, okay, you have an actual offer on the table?" And I was like, "Yeah, dude, it's been so hard, such a long road." You know, even though it had only been like 40 days, but I was like, "Dude, I, yeah, it's just been ups and downs, but finally we're here." And I was talking like I had arrived at some destination. And he goes... He just looked at me, he's like, "This is not over. Actually, you just reached the starting line. Now it's time to sprint."

    17. SP

      [laughs]

    18. SP

      And I, I've repeated that advice to so many people of now it's time to sprint, because so many times this happened. Let's say you're fundraising for a company and you've spent, you know, three months trying to fundraise. You finally get money in the bank and you're so happy, so, so satisfied. Your whole body just wants to relax. And it's like, oh you... No, welcome to the start of the race. Now, now it's time to run. You ready to run?

    19. SP

      Yeah.

    20. SP

      And like-

    21. SP

      The work starts

    22. SP

      ... especially true when it comes to closing, uh, uh, M&A. It's like when you have the offer-

    23. SP

      And what a lot of people don't realize is it, it, it takes from getting the offer to actually getting the money, that can take six months. That could take-

    24. SP

      Exactly

    25. SP

      ... for, for me it took, they emailed me in, they emailed me in September or October. I got paid in February.

    26. SP

      Yeah, exactly. Three months, six months is very common. And so you, um, yeah, that's the time that's super the hardest. The second thing he said was he goes, um, "Show me your data room." And I was like, "Oh, uh, we have a Google Drive, but like it's kind of messy right now." And he goes, um, he goes, "You're selling your company. Think of it like a product on Amazon. How does Amazon sell a cr- product?" I'm like, "Uh, they have like a page and a one, like a one-click buy." He goes, "Exactly. You need to turn your entire company into a giant buy button." And I was like, "What is that?" He's like, "You need to like- Answer all the questions now. Get it all organized now. Put it all in place now, so that when they look at this stuff, they are ready to one-click buy. If th- the more questions they have to ask you, the more you have to go dig stuff up, the more half or incomplete information you have, uh, to give them-

    27. SP

      Uh-huh

    28. SP

      ... the more reasons that this deal could fall apart. Turn your company into a giant buy button.

  9. 43:00 – 47:00

    Muddying your margins

    1. SP

      That's the other advice I've get- given, which is like, what are all the, the ducks I can line up here so that this just becomes a, you know, easy to understand, easy to consume, y- uh, you know, process for them? And, like, it was the one, you know, 30-day period of my life where I became Marie Kondo. I organized the shit out of my company. I took everything, and I was like, "Look, this need, needs to be bulletproof."

    2. SP

      [laughs]

    3. SP

      And, uh, I'm so glad that I did 'cause it was, it was extremely necessary.

    4. SP

      Do you wanna do one last one?

    5. SP

      Yeah. Oh, b-by the way, I have one... Never will I ever, uh, run my company like a personal piggy bank. So, uh, I made this mistake before, and I have a story of a friend of ours who, uh, made this mistake before. So what a lot of people do when they run their company is you start to make some money, and then you're like, "Oh, I have to pay taxes?" And then they're like, "Fuck, taxes suck." And you're like, "What can I do to, like, reduce my..." Uh, uh-

    6. SP

      Spend it all

    7. SP

      ... they're like, "I think smart people, um, smart people have, like, tax stuff they do. So why don't I do- let me start doing some tax stuff." I was like, "Okay, what's the tax stuff?" And they're like, "Oh, let me, uh, uh..." Like, we talked to a guy recently that was like, "Oh, I created my own captive insurance program, and then I bought this property that we're using as, like, a, a office." And I'm like, "I- I mean, what are you doing? You're just trying to save, like, 200 grand of taxes, and what you're doing is actually you're ruining your books." So, like, when I looked at his business, the business looked like it had no profit. And he's, like, you know, so happy that he's, you know, has this, like, shitty margin, s- shitty net profit margin, 'cause in that year it saved him on taxes. But the reality is, if you're building a company that you want to sell, you need to take some short-term pain of having clean, simple books that you pay, you know, legit taxes on in order for you to have a big exit at the end, 'cause they're gonna see a track record of multiple years of solid profits that, that you're gonna sell in the end, right? Like, that is just generally better. There's, of course, exceptions to both cases, but, like, generally that is a better approach. We have-

    8. SP

      And if you don't wanna sell, there's a, th- there is, like, a bullshit category on QuickBooks that you can put stuff into.

    9. SP

      [laughs]

    10. SP

      But that is not ideal if you're trying to sell.

    11. SP

      Yeah, exactly. It's, if you're trying to sell, you wanna ha- you wanna be able to show a track record of, of success and, uh, versus, like... You know, I had a friend who [laughs] would go to the bank on December 30th and take out a bunch of cashier's checks that they were gonna use to pay vendors, and it's like, um, pre-pay vendors for the next year. And then the next year they're like, "Ah, I g- I wanna s- quit this vendor, but I've already pre-paid 'em." Or they'll, like, take two of the checks they never even paid and then put it back in the bank a, a month later and hope nobody notices. It's like, dude, just don't do this shit. Like, don't treat your company like a personal piggy bank if you wanna sell this someday, because nobody wants to buy your hot mess. And, um, I think it's very... And you can't undo that. You see, you can't really unwind that. These are, like... It's in the, it's in the history books. Every year that you're doing that, you are kind of, like, making your... You're adding a bunch of asterisks to your own books that, like, you need a buyer who's willing to go and do a bunch of add backs and try to figure this out in order to feel confident that they should buy this business.

    12. SP

      When Dave Portnoy sold the... You know, he sold Barstool Sports a couple times, but the first time he sold it, he was like, "I was an idiot." He's like, "I owned a racehorse that I bought [laughs] through Barstool Sports." And so Barstool Sports owed, like, two racehorses-

    13. SP

      [laughs]

    14. SP

      ... uh, a trailer for the racehorse. Uh, they owned, like, the house I was in. Like, he said all this stuff that the business owned, and he's like, "We got docked so hard for all those things."

    15. SP

      Like, 3,000 liters of gin that we acquired, like [laughs]

    16. SP

      Yeah. [laughs] And that's what he said. He's like, he's like, "Chernin didn't wanna buy, like, Skippy the racehorse."

    17. SP

      [laughs]

    18. SP

      Um, but the business owned it, and we... It was really hard. You know, when he first sold that business, he sold the first portion of it, and at the time Barstool was a big deal. He only sold it at a $15 million valuation-

    19. SP

      Crazy

    20. SP

      ... when it was worth way more than that, and it's probably because it wa- he was just sloppy. Uh, a lot of it was sloppy. And he was like, "I also, like, made so much profit, and I didn't put any of the

  10. 47:00 – 51:36

    Closing a deal remotely

    1. SP

      profit back into the company. I just would buy horses and shit like that, and gamble." He's like, "And gambled like crazy 'cause it was content." Um-

    2. SP

      [laughs]

    3. SP

      Is that it?

    4. SP

      I got one more. Never will I ever just s- just stay at home when there's a deal to be closed. So this is the rule of just get on a plane. Go meet, go meet people in person. Don't do Zoom calls, or if you're doing Zoom calls, add in the in-person afterwards. Uh, the in-person meetings are so important. Um, you know, uh, I'll, I'll tell one story, which was, uh, uh, just a deal we closed recently. Uh, the... You know, o- one deal that we didn't close that I got on a plane for, and, like, you know, for me, I, I, my, the running joke on the spot is I, I don't leave my house, and it's true. I really don't leave my house. I don't like to do that. I got little kids, and I don't know, it's, for our family life, it's very disruptive to travel if I go, if I leave the house for, like, five days or whatever. But I did for this one deal. It didn't f- the deal didn't go through, but I could sleep easy at night 'cause I'm like, "I did everything." Like, I made multiple offers on this deal. I got on the plane. I met them in person. Like, you know, uh, we did everything that we could p- we could do. Uh, we did what was in our control. Um, with a d- deal that we just recently did, the other party was like, "Cool." Like, after the initial conversation of interest, they were like, "Cool. Uh, would love to just next chat, would love to do it in person. I'm happy to fly out to you wherever you are. Let me know which day works. I'll fly in same day, fly out same day. It, it'll be easy." Um, and I was like, I respect this person and I trust doing business with this person 'cause they understand this principle of, like, you just gotta get on a plane and you gotta go meet somebody, and you should be willing to do that. When we sold to Milk Road, I had a similar situation where we, um... Remember I told you about the high offer and the fair offer? We had said no to the fair offer, took the high offer-

    5. SP

      Yeah

    6. SP

      ... then regretted it. So we went back to the fair offer months later And we were like, uh, I was like, "You know what? I wanna see what those guys are up to and see if there's a deal to be done here." And, uh, I kind of called or emailed, and it was sort of like we, we just had, like, a quick ch- or I texted, I think, and it was like there really, really wasn't an opening. But I was like, "Hey, I'm gonna be in the city tomorrow, um, you know, for my niece's soccer game." Um, so I was like, "I'll go see my niece's soccer game, but I'm gonna... I'm really doing this to meet you." But I made it sound to him like I was going to the soccer game. And I was like-

    7. SP

      Right

    8. SP

      ... uh, you know, "Would love to catch up." And he's like, "Yeah, great. Let's do it." And so we drive into the city. Um, car breaks down on Van Ness, and my car literally just shuts off in the middle of the road.

    9. SP

      Your car breaks down?

    10. SP

      The car literally shuts off.

    11. SP

      What type of car breaks down?

    12. SP

      Uh, I don't know what happened. The car stop, stopped driving, and I, like, w- and the momentum t- let me just get it to the side of the road, but I'm there with my w-

    13. SP

      Don't you have, like, a brand-new Escalade?

    14. SP

      This is the BMW before that. So, um, this is... You know, I'm with my wife. My two kids are in the back in the car seats. Car's broken down. I got this meeting in, you know, 10 minutes. And, um, I'm like, "Shit, uh, I guess I gotta cancel this meeting," you know, whatever. Who... Like, who knows what w- if this meeting, anything would've even come of it anyways, but, like, whatever. We'll wait for AAA. And my wife is like, "No, you gotta go. You told... You've been telling me all morning how this is an important meeting. Like, you think that... You have a feeling that you could be able to, to get this deal back on. Like, you know, go." And, um, I was like, "I'm just not gonna leave my wife and kids on Van Ness in San F- in the middle of San Francisco in a broke-down car." And she's like, "Just go. We'll be fine." I was like, "Okay, you don't have to tell me twice." And so I hop out, and, uh, I just literally run.

    15. SP

      [laughs]

    16. SP

      I s- I run down Van Ness, like, you know, a mile basically, get to the coffee shop, meet the guy. Deal comes back to life by the end of that coffee meeting, and we end up selling to them. You know, and I'm like, I, I think I'm, I'm actually, like, 100% sure if I hadn't gone to that coffee meeting, that deal doesn't happen. And, um, 'cause in that meeting we were able to clear up some things that, like, were not as exact transactional, but, like, you know, kind of what his fears were and what our hesitations were and really kinda suss it out and get, get comfortable with each other in person. So yeah, insane. Insane that that happened and, uh-

    17. SP

      This is like a, this is like an anti-ad for BMW.

    18. SP

      Yeah. Don't trust them. [laughs]

    19. SP

      Yeah, don't trust them. They're, they'll ruin your deals.

    20. SP

      [laughs]

    21. SP

      Um, well, that's sick. Um, hopefully people dig this. We did a little Q&A for this episode, except on one topic. I think we're gonna keep doing these every other Tuesday, right, for now?

    22. SP

      Yeah, we're, we're trying to come up with great topics that we can kinda shoot the shit on and then share maybe, you know, either our answers or, or, uh, s- stories that, that we've been through. So I think that was good. I think people will like this one. But let us know. Let us know in the YouTube comments what you think.

    23. SP

      All right. Well, we'll end there, and that's the pod

Episode duration: 51:36

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