Adam Robinson Interview

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What's up, Dtcpod? Today we're joined by Adam Robinson, who is the founder and CEO of Retention.com. So, Adam, I'll let you kick us off. Why don't you tell us a little bit about your background and what you guys are all about@retention.com.

So I'll give the three minute bio. I'm 42 years old. I graduated school from Rice University in 2003. I went to New York. I was a credit default swap trader at Lehman Brothers. My roommates in my apartment started Vimeo, the video sharing website. So I watched that happen as I was a trader for ten years. We were both kind of, like, killing it in different ways.

What they were doing seemed much more interesting. And the financial crisis happened. Like this job I had, they literally made a movie out of it's called The Big Short. It was a very interesting place to be at the time, but afterwards it was kind of like it was a shrinking market. I really wanted to do what these other guys had done, tried to get into tech. Somehow I found my way into the email marketing SaaS world, and I created a company. It was called Robley email marketing. It was a newsletter app, and we were, like, sweeping breadcrumbs off of the constant contact, sort of.

That's who we were positioning ourselves against. And it worked well to the extent that it was a decent lifestyle business. But that space was incredibly difficult to operate in. There was this MailChimp behemoth that had a free product that had an unbelievable brand and were bidding up all the channels. Like, it's amazing that clavio after the game appeared to have been won, came and did what they did. I mean, they got a couple of breaks along the way, but like unbelievable with how dominant typically it's like above 60% of a market in like that was the shape of it. It was like MailChimp was everything. There was like constant contact.

It was like the Pioneer, but they got crushed by MailChimp. And then there were like 150 vendors with 2 million in revenue, right? So it's like selling cola, like very commoditized, very mature, whatever. So I was trying to figure out how to grow a company in the space, watching people niche down and have success like ConvertKit or Clavio or something like that. And I just couldn't come up. Everything I tried didn't work. And I heard of this identity product, meaning when someone hit a website without them filling out a form, you could get an email address of that person. I immediately thought, how is that possible? If I could do that, I could sell that to anybody with a website. No fucking question.

I've been in the email market for five years. This is the biggest problem in email, right? Of course, the ethics of it are debatable. The compliance landscape is completely misunderstood. But I was like, screw it, I got nothing else going on. I'm going to try it. At the time, it was entirely a third party cookie solution. I thought third party cookies were going to expire 18 months later because that's what people were saying in 2019. But I was like, I'll just try this, whatever.

Make a couple of million bucks and beyond to the next thing. Turns out it's not illegal. Third party cookies have not been sunset yet, and we can do the identity without them. Two and a half years later, we honed in on basically large shopify stores, the direct consumer side of them being this perfect customer for this product. And then in addition to just having a top of the funnel tool where someone hit the website left and we give the Clavio account an email address, we also built out a whole suite of bottom of the funnel. Products because there's this major problem where in order to receive an email flow, the user has to be logged into the merchant store, which is a fucking terrible problem. On chrome it's hard enough. On safari.

It's impossible. Exactly. Like, you're logged into Amazon, you're logged into Facebook, you're not logged into feet.com for like socks or whatever, right? Like Love Taylor offer, but no one's logged into his fucking store, let's be honest. So with chrome, it's difficult. Maybe you get a purchase and then the cookie lasts for whatever, 30, 60, 90 days, maybe a little longer. With Safari, it's nearly impossible because those cookies expire in seven days. So, yeah, we can expand these abandoned cart audiences and product and checkout and category and like, whatever else. Price drop back in stock if you want it by a lot, and it works and it's incredible.

So the company was called Get Emails, which really makes sense when it's a self serve product that you're selling to anyone and all it does is get you emails of people on your website. Great name. Once we were like, we noticed sometime in the middle of last year, it's like, wow, these big shopify stores like BlendJet, Drift, Kitsch, Blissy. Not only are they consuming massive amounts of this data and really making it work, they're literally sending us like four or five brands each per month and not even asking for a commission or anything. Like, no, they're not churning. They literally can't stop talking about this. So then, like, we did this bottom of the funnel stuff. It worked better than any product I've ever seen.

Like, in terms of just immediate lift. It's like you turn it on and someone's abandoned cart. Revenue goes up by, like, two or three X. It's unbelievable. So I was like, oh, we should only focus on these big shopify stores. There's a nice shopify plus market. We can go after them. Get Emails don't really make sense anymore.

We had a ton of free cash at the time because we hadn't hired anyone. We had, like, six people, and we're doing 12 million arr. So I went out and bought retention.com the Domain for 800 grand last August. Just fucking whipped it out. And now we're trying to scale as hard as possible in dealing with the challenges of doing that. So, like, you know, I'm doing a build in public on LinkedIn. We're like 20, just shy of 20 million arr. Now we have 50 employees.

You're probably hired a little too fast. Everything's messy, but we're slowly improving the focus and what we're spending time on, the visibility through rev ops is getting better. I'm sure anyone who's gotten to this point, they're nodding their head. It's like, yeah, you went too fast, but you'll figure it out. So that's where we're at.

That's amazing. I'd love to dive in a little bit into the actual space you're in. So once you're able to get the emails, because there's all this talk about, like, you're saying cookies and privacy and what's okay and what's not okay. So if you're able to obtain the email, what are you allowed to do with it?

In the US, which is the only place our product will work for your US traffic, you could be a Canadian or European company and use it for your US traffic because these laws are based on the geography of the activity on the Internet. So if you're in the US, you are allowed to email these people. Why? Because the Cannes family of 2003 is opt out, not opt in. That is not debatable. That is a fact. Warby Parker, Dr, squatch, True classic teas, BlendJet, penske, media like Tonal, bulletproof coffee, all of them have in house counsel and they are currently our customers. This is not illegal, right? Like, why does everyone not spam everyone all the time is the next question. Because if you did, Gmail would not accept your emails anymore.

Yahoo would not accept your emails anymore. Email is a game. It's not about first party optins. It's about engagement. It's about high positive engagement and low negative engagement. So we have like reverse engineered email in a way to where it's the perfect non opt in email. And by the way, we have opt Ins through our we have implied consent into our identity graph. So if someone complains, we give the customer opt in date and URL and the complainer goes away.

That's just how it works. So it's like this is like news to a lot of people. Most are not aware that that is the actual law and most are not aware that this is a strategy that sort of can work, right?

Yeah, absolutely. I think there's a bunch of things that are really interesting here. One is, like, you were saying that brands are actually able to do this, right? I think that's really important to know. And the other thing is that, like, you were saying it's opt out instead of opt in. So what you're basically saying is that the goal if you're sending an email, you can send an email to anyone you'd like. But if they're saying, mark, this is spam and they're saying unsubscribe and all that, then that's sending a bad signal to Gmail and then your deliverability for your domain is going to get wrecked. So then part of the job is figuring out, okay, I've got this email. How do I send an email where I'm able to build trust? And I'm not just spamming these people because that's no good for everyone.

But I am, as a brand, allowed to send them an email.

You are allowed to, yes. So, like, by the way, we could give people 80% of their traffic to a plain text email. We end up on average giving somewhere between 15 and 17%. We throw out everybody else because they're not perfect enough. That's how high the bar is for a deliverable email. Like, we're buying signal from all over the place and if they meet this ten different criteria based on all the signal we're buying, we'll give them the record. They must be openers and clickers in the past seven days plus a bunch of other stuff to actually have it hit the brand account.

So you're basically saying, like, you're not going to pass over every single email if you know this is a type of person. Yeah. So if this is a type of person who maybe hit their page, but we know that they unsubscribe and they mark everything else as spam, those emails aren't getting passed. But if they're a good email and we know they're open to it, then we're going to pass those emails and the brand can try to win that relationship.

So you said I have to own the entire stack, basically. And is that when retention.com went from six people to saying, let's just go all out? First of all, having six people and like, 14 million in revenue is absolutely wild. So what clicked?

It was so great. Now I'm looking at this now and I'm like, what am I fucking doing? Because if I just would have gone one more year of that, I don't know, I probably would have made, like, $8 million of cash. Yeah, I don't know what that feels like. Yeah, be great.

You mentioned this quote that you said you bang your head against the wall for ten years, and then all of a sudden it's way more success than you ever thought possible all at once. Is that the moment that you said, we're going big?

Yeah, you know what it was? And I wonder if I can share my screen. I don't even have these anymore. So I mentioned that we figured out that shopify guys were, like, our best guy. And then we literally were, like, tracking performance of the abandoned cart flow audience expansion in a spreadsheet for BlendJet, Blissy and Kish three brands.

What did you mean by performance with those?

The old abandoned cart flow? And then literally the incremental from our audience that I see giving to Ryan. Right? And I had these snapshots of these spreadsheets. It was October or whatever. Maybe November. It was like, around a holiday season, so it was like the volumes were way escalated for everybody. But it was crazy. This thing was like I was like, dude, it takes an hour to set this up, and this guy's got $170,000 of incremental. You know him, you can ask.

And he's paying us five K a month. And I'd get off the phone with people and they'd send, like, seven intros on the wire. Because I'm also like, by the way, I think people buy this way in the shop value system. Like, I'll pay you 20% for life on any of these closes. Like, we have this great affiliate program, and it was, like, overwhelming, if you want to call that inbound. Like, the amount of inbound interest in this, which was just really different from the prior. We always had some decent inbound, but once I was able to show people that it was like, it got incredible product market fit on the affiliate channel, like, with anyone who knew brands because they could just I'd be like, dude, if you make me an intro, it's like a 30k ACV. It's a seven day sales cycle and an 80% close rate.

Like, I can show you salesforce. Anybody that who's trusted by brands, right? Just show them these spreadsheets and they'll show up at the door and they will buy. So it just opened this incredible spigot or whatever, and then yeah, decided to we thought that the market was big enough to create like a unicorn type. I mean I know that it is because like clavio yapo sort of Attentive, there's a handful of shopify type unicorns.

This reminds me of the Attentive days when they were just going gangbusters racing round after round and getting the market share. It seems though there wasn't much novelty and it was sort of a race to being first. Do you see some of the same here or there's? A little bit more like behind the scenes going on.

So that's a really interesting thing that's going this space. The blessing and the curse is the total misunderstanding of this compliance landscape. The blessing is that no entrepreneur worth their weight in salt is going to enter this space. VCs are too lazy to actually learn and even if they really believed it, there's like a couple percent chance that something really out of left field happens on the compliance landscape and we're fucked. Whatever. That's kind of always the case. I feel like with these early stage startups, like something can happen that just levels you that like you just were totally, totally not expecting. I paid a lot of privacy attorneys a lot of money, like 98% sure that we are fine for ten years, right? Almost no one else believes that.

You hear about the product and you're like, this is illegal. If it's not, it's going to be very soon. It doesn't matter how smart you are and people are very convicted in that but they have done no work. So like this is a beautiful environment to operate in because it keeps competitors out. Now I'm a jackass. I'm fucking sharing my financials on LinkedIn and everything. So now I got competitors popping up. Like there's this guy growbot or something who literally has taken my exact first marketing video for this product and like using all of my copies, recreate, whatever.

Like I take other people's copy too who are emulating. I appreciate the flattery but I would be surprised if you were able to raise real Venture Rounds just because of the name. It's going to make it hard for me to sell this business at some point I think unless we're very different than we are now. Because you really need someone who understands and who appreciates this dynamic that in exchange for this data privacy risk you are taking, you are getting unbelievable unit economics. That's the trade you're doing, right? So I didn't have a legit toe to toe competitor until we were 20 million arr. Now we're spending a million dollars in sales and marketing our products moving incredibly fast. He's trying to undercut like I don't know, that's generally not. It's like we're going to do next year, we're going to do 200 dinners.

That's how people buy in shopify. Also, is he going to be able to give people free trials instead of 60 day paid trials and undercut by 50% and make a dent? I don't know. I would bet that we'll probably continue growing at a higher growth rate off higher numbers. But I'm going to stay humble and hungry and appreciate the fact that we have a competitor. So that's sort of like the nature of our space right now. I would be very scared if somebody came in and raised $100 million to come after us. It would probably make me change my tune about doing primary. I'd be really fucking annoyed.

You ended up raising right.

No bootstraps.

I see.

I'm contemplating doing some type of secondary at some point. The business has to be we need to figure some stuff out and get a little more predictable before I'm comfortable making the promises that I would make for the valuation that we would want.

Before we dive in more into the business and those decisions. While we're on the privacy topic for brands that might be considering this, what is it that you, Adam, as the founder, tells the brand? So they have peace of mind that this is not going to affect their brand in any way whatsoever.

There's legal and then there's actually a brand concern that they all also have. It's really with these more sophisticated brands. It used to be with the entry level when we were starting out in a self service. Like, how is this legal? How does it work? What do I send now with these shopify guys who are bigger and, like, mid market? It's how's it legal? Will it hurt my deliverability and will it hurt my actual brand? Right. Because they care about that. Right. So, look, from a legal standpoint, it's just black and white. It's what I said about the social proof.

There is no way that these brands would be using it if what I was saying was untrue. It is legal, period. Right. There was a lawsuit a couple of weeks ago. Maybe it was like two months, actually. It's a class action against an indirect competitor that more or less does what we do, but in a different way, called Safe Opt. Pete's Coffee and every man Jack were named on the lawsuit. That freaked people out.

However, the lawsuit had nothing to do with the email part of our business. It had to do with pixel retargeting. There are 100 Pixel Retargeting companies. They're all getting sued for this right now. It's like hot jar. You know, Facebook's got 100 lawsuits against them. Right. But because it was Safe Opt and they're a small niche company, and because brands were named in the lawsuit, people are freaked out by this.

The lawsuit is not about email. It's not even a CCPA lawsuit, because there's no right to private action with CCPA. It's government only with CCPA. So it's going to be the big companies first. They're not going to get around to smaller brands for ten years, probably. Right? It's these ambulance chasers looking for a theory to sue around a wiretapping law, which is obscene, but the claim is that the consumers had no idea what was going on. There was no consent gathered. So like the direction all this shit is going is that if you actually put a cookie pro from one trust or whatever the GDPR cookie consent thing at the bottom of your site, and you say like we can give you language.

Something along the lines of we will take anonymous Identifiers and try to connect them to personally information, sometimes an email address. And we might try to mail you if someone accepts that there is absolutely no way that your brand is going to get a class action lawsuit against you for doing that, because the only leg they have to stand on is that the consumer was unaware and did not consent. So if you have proof that consumers consented to that, the only argument now with any of this privacy stuff, it's not whether or not you should be able to do it, it's whether or not proper consent is being collected for it. So I think that the end game of all of this state level stuff is just more banners and, like, more descriptive language. That's it. Nothing else is going to change.

And the cost of not doing that is the opportunity cost of not making the revenue dashboards like some of your customers have it.

Yeah, look, people who are concerned about showing up in a class action lawsuit, I don't think understand the way the world works. This was not, again, not to beat up on our boy Taylor offer, but it wasn't pete's clothing who was in this lawsuit. It was pete's coffee. It's a brand that everyone in America could see on a lawsuit and recognize. Anyone who's concerned about this is not at that point yet. Right. So it's kind of like this other thing. But yeah, I think it's like, look, it's not my place to make legal decisions for brands.

I'm just like making the claim that brands that are a lot bigger than you are are very comfortably doing this, and the way they are is they're collecting consent for it, and there's no debate about the legality of it. So back to the actual will it affect my brand adversely? I always said it's not a legal conversation. It's an ethical conversation. Or it's like whether or not you feel like this is a polite thing to do or whether or not it's aligned with your brand ethos that you would do such a thing. Right. And dr. Squash was on stage with me at grow la in March, and I'm like, bro, what were your hesitations? He's like, of course, the legal thing. But then he's like, well, I thought, there's no way it's not legal if they have these brands.

And sure enough ran it through our in house council, it's legal. And he's like, the deliverability thing. We had clavio audit our account as we started, small and scaled up, and you can just tell right? Like, if you start small, you can see that it's not adversely affecting you. And then he's like, on the brand front, we were like, okay, think about it from the consumer's perspective. If they just hit their promotions folder and you look at what's in there at any given time, if you just stuck an email from a website that you were just on, it's probably more interesting and relevant to you than anything else in there. I was like, I should have come up with that myself. That's amazing. But I agree with that.

He's probably right. You might have opted in for all of this stuff years ago or whatever. I don't know how it got in there, but something from a website that you were just on has to be one of the most relevant things in there.

Yeah, I totally agree with that. I think the other really interesting thing here is just like the power of email and how persistently powerful email continues to be as a channel, especially as everyone is thinking about, oh, I need to be doing this on TikTok, I need to be running ads. Like, email is so powerful, people convert, they read it, they open it, and the attribution and everything is there. It makes total sense why when you're able to get these emails for people who want to get them, you're seeing those numbers. My next question is going back to what you were saying about now it's on the brand and making the brand decision. Is this something we want to engage in and how do we go about doing it? What are some of the strategies that the brands are using when they're sending that email out? Like, what is that first Cold email where there hasn't necessarily been the defined opt in? What are they saying and what are some of the strategies behind that?

So this is going to sound very strange, but I used to own an email marketing SaaS app. The whole thing that we did was deal with deliverability and you learn a lot about it and you run across some dodgy people in email. I'm just going to open the kimono on how spamming works, right? When you are introducing cold emails into a bulk send, the relative importance of the content is very low. The relative importance of the aggregate negative engagement is incredibly high. So as a rule of thumb, if this makes sense, you're always trying to nurture this body of 30 day engagers. And what spammers will do is they will slowly add on Cold emails, like 10% of their 30 day engagers per send into a bulk send. That's very sort of generic. The complaints happen against that larger body of email, so it goes unnoticed by Gmail and Hotmail and like, whatever.

There's no way to fingerprint, there's no way. Then the positive engagers of that email get sent a welcome series afterwards. That seems totally counterintuitive, but what's important is the fact that the negative engagement gets lost and then you take the positive engagers of the cold emails out of that big send, then you start doing very targeted whatever you were going to do. Thanks for coming by the side, or like, welcome, siri, whatever, but that is the way that you make so, like, by the way, we weren't telling people to do that until probably three months ago and it was working fine. We were just saying, copy your welcome series. Like, the emails are okay. It's like the spam rate is a little higher than would otherwise be. But the way these ISPs look at it is of everything that went out that day, like, what was the total open click unsubscribe.

So it's like the unsubscribe of the welcome series might have been three or 4%, and that's too high. And like, the complaint rate might have been three out of a thousand or two out of 1000 instead of one out of 1000, and that's too high. If you were sending to that and that alone, it wouldn't work. It would it would get blocked. But that's in aggregate, it's like 2% of people's email flow typically. So that's how it works. The only problem you run into is if for some reason a CS person at Clavio is looking at your account, they're like, stop doing this. The engagement's dog shit.

It's like, it's too bad, wherever you're getting these leads from, don't anymore. So the solution is just move the welcome series to behind the first newsletter, then it's untraceable, really. So that's how you do it safely every time. There's nothing that can it's just math. Like emails in that regard. It's just math.

Yeah.

You're washing these emails.

I love that you're basically taking the emails, you're just blending them into your traditional flows. Your traditional flows have open rates that are totally acceptable. It gets lost in that and you get positive engagement and then you roll them right into your email list, just like you would had they manually opted in. Because there's plenty of people who maybe hit your site and they click out of the pop up or they don't enter their email in the footer or anything like that, but you're able to reclaim those and bring them into a top of funnel before you even knew you. Like a higher top of funnel almost, right?

Yeah. And just to be clear, it's like ten times more people than would fill out a form. It's like an unbelievable lift.

Oh, 100%. I mean, we see it on my sites. Like, I have a site with 100,000 hits a month on it and the conversion of actual customers and email subscribers like you're in the single digit percent, but the amount of total volume that we just don't know who they are and they hit and balance is gone. So that's my next question. Not maybe not as relevant to D to C, but just. As a quick sidebar, do you guys serve other verticals as well, or are there companies that serve different verticals? Or is it strictly an ecommerce focus?

We decided in October of last year to only sell to these shopify guys. And we're probably going to go upmarket into sort of competing with Wonderkind. And then I want to do this free product which does server side tracking for the conversion API. And basically, very simply, it's like the conversion pixel on Facebook is not capturing and therefore unable to label Safari conversions through a very simple third party integration. We can just send events for conversions for those people and the perception will be that the conversion rate will jump, which I think is like, that's just good to know for a lot of reasons, it will be a dopamine hit. And then I think it can be like a value ladder into we can do stuff in Clavio with server side tracking laying down first party because it's getting pretty technical, and then sort of work them up to our other stuff. So for now, it's like this ecom ecosystem we're focused on for this we're actually creating. We're going to try to beta test this B two B product, which is like, profiles of people on your high intent B two B page.

It's like a pricing page. And then it's like people who are engaging in your social presence. If you have one in the last 24 hours and show them, it'll show, like, how to just hit them back or whatever. And then there's this third party Intent data market, like bombora G two crowd, like, whatever. They're all really expensive and there's no aggregation of them, and they're very unqualified. And like, this guy Santosh, who's my CEO, he's like the B two B data god. He built some info and Apollo IO and stuff. And he knows this B two B Intent market, like, better than anybody.

So he thinks he can put together like, a third party intent data product of verified people looking at your space. That would be way better than what's out there. And we could do it for like $1,000 a month. So it would be, like, wildly disruptive because all these other companies are US based. They have US based salespeople, so they have to be 30, 40, 50K ACV on the low end. So we're trying to get that product in motion. That's kind of like the next S curve idea. It helps our business profile a lot to make something like that work because, like, there is such sensitivity in, like, shopify won't buy us.

Like, they have a different privacy ethos. Clavio doesn't want to touch it. We'll get a financial buyer, maybe we'll get a revenue premium. There are BDB companies who would pay like, billions of dollars for the BDB data side. It's like a totally different the ACVs are so high. It's like if you can it's like identity intent in that market is really interesting. I mean, that guy who knows it in the back of his head.

I've seen it firsthand from a good friend of mine, Nick Walden. I've seen him build in the data space recently. He's just starting to take off the thing with him when he explains that you have to be so deep into that world to find the unique advantages and opportunities. But they are there because it's still so early in the data game. And this is even like pre AI stuff. It's going to get even crazier in terms of finding loopholes because they exist. It's just willing to be unconventional. And then again, also, you have the advantage in being in the place of having the mindset at the right time, of having nothing to lose because you were profitable.

You grinded at it for ten years. Nothing else possibly worked. So I'm curious on this guy Shantos. It seems like he was a big sort of inflection point in your career. And when I started doing research on who he was because I found him on the video that you had. Yes, he is like a data god, b to B. He was a zoom info. And the thing that clicked with me is, for example, I have Pharrell Williams invest in my business, but I got lucky there.

But it's like something that I never thought would ever be possible, that I could work with someone like that. And so for most entrepreneurs, I'm like, how did you get someone like Shantos? Let's talk about who Shantos is. But you tried everything that wasn't working. And it's like people from the outside can think, well, how a guy like that would never want to help me out. Why is this guy taking the time out of his day to help me out? And it seems like you were in the weeds with him, so we'd love.

To hear more about that. Yeah, he's transitioning to full time COO. He should be full time COO by, I don't know, a month from now. He's winding down the engagement. He's co CEO of another company right now, and everybody that works at our company feels that way every single day. We're like, we cannot believe this fucking guy chooses to spend his time working on this. I mean, we're paying him a lot, a lot of equity, a lot of cash. But still, it's amazing because I wouldn't have had the confidence to do, like, every situation we run into, he has seen before.

He has navigated his way through it's amazing. So how did I end up with him?

How do you find the confidence to get someone like that to get interested, motivated?

So the story is like, the thing that set me looking for someone like him was I was about to sell this company and the guy walked. It was a lot of money. The guy walked and I was, like, devastated. And then Dave Chasper aye guy who I share an office with, he, like, connected me to to this CRO who he totally inspired me and was just like, dude, I had six employees at the time. One salesperson, 8 million arr. He's like, this is unacceptable. Hire three more salespeople. Like, I'm not telling you to do what we're doing, but you have to try harder than this, right? You're only hurting yourself.

And he's like, you have gotten far enough to where he's like, there was this thing that with my first company, if I wanted to build a sales organization, I would read a book on how to build a sales organization and then do it myself, right? And he's like, you and Dave have the same problem. Like you think like that. He's like, you need to hire someone like me who knows how to do this and can just do it for you, right? You've earned that at this point. So I sort of set off looking for someone like that. I thought I kind of found one. I didn't. I mean, I had him consult for a couple of months. It was like an enterprise sales leader kind of in the space, and it wasn't right.

And then one of the problems with that guy was I thought the move was like, up and hard. It wasn't like, our move now is kind of down. It's like not min market. It's like shopify first. But Warby Parker had been paying us like, 50 grand a month for like, two years, and we only have one of them. And we'd get Harry's on the phone for a demo, nothing would happen. Smile direct. Nothing would happen.

It's like, well, we need to figure out how to get more Warby Parkers. Because even if I had ten of them, then my business is in a totally different place. So I thought that's what the move was. I never understood the enterprise landscape for what we were doing. And even though this guy spent a couple of months on it, I had no idea what he was going to actually do. I didn't know who we were competing with. I would go to live ramp's website. I know they can do this.

They don't mention it, right? It's just very strange. So I tried to get on the phone with people who could help me understand what the landscape was way up market. And I asked a private equity contact, and she connected me with Santosh. And she's like, I'm not sure if this guy's going to know, but I think he's going to be really interested in what you're doing. Like, this kind of exactly his wheelhouse. He loves the 10 million. No systems, no team, no nothing. And then on the other end of it, he's disinterested at like 100 million arr.

But that is the most valuable, you know what I mean? But I didn't really know this going in. And then I just had, like, an amazing conversation with this guy and the things that he was telling me that he had done. I was like, holy shit. Literally. So I went home and I told my wife. I was like, I talked to this guy today and if I can get him to work with us, everything will have changed.

What are some of the things he'd done that he told you at that moment?

I mean, he just talked about some of his experiences with like Zoom Info and Apollo IO. Not even in a lot of detail because it was only 30 minutes conversation. But just kind of the way he was asking me questions, it made me feel like he knew exactly what to do to make this a lot bigger. You know what I mean? That was kind of what it was. And I was open to it as well, which I think he would tell you is the hardest problem is the executive team is not willing to do what it takes to be a big company, right? And I'm totally willing to do it. So I begged him to get another call and he's like, I'm not sure how I can help. I have another fucking job. Like whatever.

And I'm just like, dude, talk to me one more time. And I'm like, I just have this feeling that I don't even need you to work full time or anything. Like, if you just show me the direction I need to run in, I'll run faster than anyone. You know what I mean? I don't know what to do next, right? And he's like, okay, well, he's like, quite frankly, a company that's kind of boring, it'll be wrapped up with middle of next year sometime. He's like, I'm at a point in my career where I'm not just going to work for you. Like, I need to understand the business intimately well to join. But he's like, I will spend 3 hours a day on this for a year and then we'll know. And he's like, you know, whatever.

We can do a certain amount of equity over four years. He's like, by the end of one year, you will have gotten most the fundamentals will be in place for you to the the building blocks will be there for you to scale. And that is most of the value that I will provide. Product, creativity, whatever. He's like, I can do everything else, but so can everybody. He's like, this one thing you're stuck in a place to where after you get this, he's like, basically the point was if it ends up not working out after a year, you're going to win on this deal, right? And then sure enough, like two weeks in, he was spending 8 hours a day on it. And now he's got like seven direct reports and he's effectively been full time since October or something. And it's just been transformational.

But like, it's also he's just like a really good human being and like, sort of has these, like, Eastern values that I really embrace, like, you know, just mindfulness. And he just thinks that these views of companies and the roles that they serve in people's lives and how it's just so much more than just a job. If you do it in the right way, it can just create this amazingly positive loop or whatever in everyone that's associated with it. I had always had that belief ever since I started my first company, because it was so different than Wall Street. Wall street was like, you just fucking took your pound of flesh and then you went home, and the day you had enough flesh, you would stop going to work, right? So, yeah, it's a really serendipitous thing. And I'm actually, with him writing a book, he has so much wisdom, not just knowledge. He has so much understanding about business and how it works and like, these winner take all sort of dynamics and the thing that you said, it's like ten years in a row, you're banging your head against the wall and then all of a sudden it all clicks and it goes vertical, right? He just gets the mindset and the type of experiments you need to be doing all the time to end up in that environment, and you have to keep doing them because this will plateau and you need another one or whatever. Velocity is one of his key things.

It's so much more than just moving fast, right? Velocity creates all sorts of positive energy in your company that allows you to attract better recruits and make higher goals. And there's just 50 other second order consequences of Velocity that are the reason it should be your number one core value, you know what I mean, about all these different areas of business. He really understands these subtleties. One of his other things is, like, you shouldn't try to compete with revenue, right? You shouldn't optimize your business to make revenue. You should optimize your business to destroy competitors. It should be like, how do we get to the end of the year having eliminated someone on the playing field, right? Not how do we get to the end of the year with our revenue three X or whatever. It's just these amazing ways of behaving.

I love that, Ramona. I just wanted to go ahead for 1 second there. Adam, one of the other things that I saw you post on LinkedIn that I think is related to this notion was kind of the idea that you said before you had a certain conception about building businesses and now you're like, go for it. And if you're going to do it, you may as well build a big business instead of just building a normal business. So I'd love if you could just shed some light on what your thinking was before, what you're thinking is now, how you approach it and how you approach building big businesses.

I really liked this idea. I didn't see a lot of people. I had this idea in my head. My co founder, Diana Ross, used to work for this guy, Ross Paquette, who is his company, Mara Post. For, like, ten years, he had been doing he had been stuck, but he'd been stuck at 30 million top line, 20 million, bottom line. And he owned the whole thing. So the guy got really rich just cash flowing, this business. And that was like, I had a business that was a lifestyle business that was, like, fine for a single guy living in New York, but I've never heard of anything like that.

That was an unimaginable success to me. And as with anyone who is stuck and experienced success, that sucks too, right? To not be growing. Like, it blows. Like, you don't want to be making $20 million, like, trying to make it bigger and then not working. You're miserable because you almost have this feeling that you are God, and why isn't this working? Right? It's almost harder than when you're less successful in some ways. But I always liked profitable businesses. That was what I thought the sort of dream was. But that quote was kind of like when I first started my company after Wall Street, I've been reading, like, Tim Ferriss Four Hour Work Week and, like, 37 Signals Rework, and I was really sold in these small software companies.

I was like, make a million dollars, live in Aspen. What could be better, right? But it's not. Like, what I'm doing right now is like, there was a period when I was not working a lot because I had someone else managing it entirely, which, by the way, I could do now. I could not manage this. It's just, like, really fun to do. So I'm doing it. But Steve Schwartzman in this book, what it Takes. Excellent book.

He's the guy who created Blackstone, which is, like, the biggest private equity firm. It's publicly traded. He's incredible guy. He recaps his advice in this book, and there's, like, 40 things he recommends. And number one is it is not harder to create a big business than a small one. So you might as well create a big one because the rewards are so like, the position that it puts you in at the end of creating it in the world is just so much more desirable for so many reasons, right? In some ways, small businesses are probably harder. I don't know. And then Sanchos goes even further.

He's like, the bigger the vision, the better the people you're going to get to work on it, the better the people you get to work on it, the more likely it is to actually succeed.

How did you get over the hump of the biggest transition there, which is the one thing that really changes is people. You're dealing with people problems. You're managing. You're getting hires wrong. That's the one biggest difference. Between running a small business because the operations of it becomes easier, but yet you're just dealing with more people. So I'm curious, how has that transition been? And every problem has a solution. So I'm sure you've crossed that hurdle.

So it sucks. Especially senior hires. We've gotten a lot of them wrong because I think they're just really easy to get wrong. It's like so hard to know the people that we've gotten right. Almost everybody who's been around, of the top ten people, it's like seven of them started consulting for us, which is just really interesting. And then it sucked them in from their other shop or whatever. So, yeah, it blows the fire. People, fortunately for me, I hate doing it, so I'm not the one firing anymore for the most part because I only have a couple of direct reports.

But yeah, man, it's like people problems are problem. The problem and things related to people problems. It's the biggest problem. But I think it's just like, that's what you sign up for. It's messy. When santos walked us through what was going to happen, he's like, it's going to be messy. Like, we're going to do it way too fast. We'll probably end up hiring too much, too many people.

And then since they're people you take on, this whole layer of everything's going to be less efficient. People are going to get unhappy, annoyed. Some will love it, some will hate it. That's just what it is. And I thought I didn't want that because I hadn't really had it before, and I thought it was so nice to have this. My idea was create a business like Ross's with like I mean, I think he's got 100 engineers in india, but create a business like Ross's, like 30 million top line or something. 20 million bottom line, and have like 15. Right.

That sounds incredible even to me now, but it wouldn't I don't know. There's something about being all in once you're all in, that like, is very enthralling. It's just like it's the right way to live if you can. But it wouldn't have made sense to do it for me until all of these things aligned in the fall of last year and the signal was so clear that we should be doing it. It's a very interesting topic for exploration.

What I love about your approach is that you didn't have to sacrifice owning the business while in the case of bringing in other partners, but it's not a question about whether to race or not. Those are two very different things. And you decided to go big, bootstrapping it with the money that the business had already validated itself and making revenue. You don't need to race VC to say, I'm going to go big because that's where you can end up in the trap of being on it for five years and not have any kind of outcome or even longer.

Yeah. And one of the things that Santo said about these really successful companies is that they have a mentality as though they're founder led. And he's like, it allows them to do these type of crazy things that can lead to exponential outcomes. And he's like, so Apollo IO is another one that he joined when they were 5 million. After eight years, they were totally stuck. And then they were trying to sell 15,000 ACV deals versus zoom info, 30,000 ACV, and it just wasn't working. And Satosh was like, fuck it. $99, all you can eat.

And it just, like, created this insane inbound. It's like, if they built this thing that was like, if three or more people from the same business domain bought it, they would hit the VP sales and then do like, a mid market 40K MSA, whatever. And he's like, they were venture backed, but that go to market engine was so successful that it allowed them to still behave as though they were, like, founders. Like, the investors didn't care. You know what I mean? So they're still sort of doing things like that. And he's like, for us, it's just make more money than you spend, right? Like, having true financial freedom to do things that will eliminate your competitors rather than try to make more money to please somebody else. It's such a cool I mean, if you can imagine, I never thought that way. And this guy shows up at this.

He's like, we should do an executive off site. In his presentation, I was like, man, I've never been in a room with somebody this ambitious. But in this very non greedy way, he's just like, we're just going to go destroy people. We're going to invent this space, and we're going to make it impossible to compete with us. And it's like, holy shit, this is my company. How fucking cool is that? Somebody like this who has all this experience doing this is like, I'm going to help you make that. I'm like, I'm fucking in. Like, whatever you need.

Whatever you want. Whatever you need. It's go time.

That's amazing. I love that mentality. And I'm super pumped for you guys as you keep growing. So as we kind of wrap up here, adam, the last question I had is just this year. Clearly you guys are growing really fast. You've got your target on expanding with different brands and continuing to move up market. But what else are you guys focused on for the rest of the year? From a product side, from a company side, what keeps you up at night?

Yeah. Santos is like, if you can get hundreds of thousands of users, it has, like, the effect of billion dollars a year of marketing budget for mid market product. So we're trying to make, like, a free, very simple shopify app in implementation, which I think would be great. Like, literally just like, free for everybody. We want to do a b, two B thing, which I think I mentioned. So that's like very early experimentation phase. And then what keeps me up at night is just like, april and May were hard for us. They were hard for gorgeous, they were hard for triple L, they were hard for yapo.

There's some weird shit going on in D to C that like, I don't know, like, if this thing doesn't start growing how it was growing in February and March again, it's the wrong size. We have the wrong number of humans working on it, right? Which fucking sucks. That's going to blow. I will have just create gone from a Glorified, like the greatest cash flow situation ever to just creating this like $20 million a year churn machine where I'm not making any money. Great job, guy. So fortunately, I'm making a weekly docuseries about it that everyone can follow. And I am going to keep everybody up on it. But right now it doesn't feel great.

Look, it didn't feel great the last six weeks. I think we're on to a lot of there were external and internal reasons why the slowdown happened. Some of the stuff we couldn't control, some of the stuff we can, the stuff we can. I think we've identified and are doing some really smart stuff to get it moving again. And I think the nature of our product is we get a real tailwind in the summer in advance of Black Friday. Because people are like, I want those fucking emails for Black Friday. It's that simple. Who would not put the script on in July, right? Like, everybody would.

So I'm anticipating a big push in the summer. If not, you'll hear about it.

Love that. And where can our listeners tune in and hear more? I know you said you mentioned you have a podcast and you're doing the whole build in public thing. So where can we find you?

I'm doing most on LinkedIn retention. Adam. I'm about to pick up my Trojan presence is okay. It's also retention, Adam, the handle. But yeah, all of the stuff gets posted on my LinkedIn and Twitter. But yeah, the docuseries is called Billion Dollar Challenge. I think it's very weird for me to talk about it because it comes across as such an egomaniacal thing to do. I was on a podcast with the post pilot guys yesterday and they were like, so dude, you're making a show about yourself.

But for some reason it doesn't feel that way. It's like produce. Yeah, they're doing a great job with the storytelling. I think the episodes they've made that aren't out yet are fantastic. And yeah, it's this like a reality TV show about what it's like to be in the middle of the shit show. Like, is all this stuff happening?

I love that. Some of our favorite even that we've had on the pod I know in the CPG space, we had Jay from Midday Squares on and they were one of the brands on the CPG and snack side that did that and really embraced it and people are loving it. So as a go to market strategy and something to do, I think not everyone's willing to do it, but the people that are, I think it's the best thing to do.

I think it helps in a lot of ways. My whole thing was like, recruiting investors ecosystem, like in that order. Even though I wasn't planning on raising money, investors was kind of like sort of big secondary, possible exit at some point. And yeah, man, I think it's raised a lot of awareness. Some of the feedback that I have gotten is that a lot of people know who we are, but don't know what we do. So I'm trying to get smarter about actually talking about the problems we solve for brands a little more in the content I'm making.

Hey, it'd be a problem if nobody knew who you were or what you do. So that's a good place to be in.

Exactly. It's a good place to start. Yeah. I appreciate the good fortune that I have arrived. And believe me, I just feel so thankful. Regardless of whether it's growing slower or faster than I thought it was going to, it's still an amazing position. Sweet.

Well, thanks so much, Adam. Thanks for coming on the Pod. We had a great time.

Dude, thanks for having me.

Thank you, adam.