How Retention.com Bootstrapped to $22M ARR in 48 Months and Why It Is Pivoting to B2B (Conference Talk by Founder and CEO Adam Robinson)

Adam Robinson

00:00>> This is our January p and l. We actually got to 12,000,000 with six people. Well, mean, I I paid myself $4,000,000 last year, pirate domain burning email strategy that you can do.

Nathan Latka

00:15Hey, folks. If we haven't met yet, my name is Nathan Latka. I launched and sold my first software company back in 2015 and went on to write a book about it, which you guys made a Wall Street Journal bestseller purchasing over 30,000 copies. Thank you so much for that. After the book, I launched this show and went on to create founderpath.com. I raised a large fund to do non dilutive deals with B2B software founders. So far,

00:42we've invested in over 400 software founders totaling $150,000,000. Here in 2024, we're doing three to four new deals per week. So if you're looking for capital and don't wanna give up equity, go sign up at founderpath.com for free to get your offer. Alright. Let's jump into the interview.

Opening: Have You Ever Been Stuck?

Adam Robinson

01:00>> Alright. What do we got? Okay. So the ringer's turned off. Let's go. Okay. Question for the crowd. How many people here have ever been stuck?

01:11>> Come on. I mean, is my experience as an entrepreneur. It's getting stuck and getting unstuck. So how many people have been stuck and gotten unstuck?

Adam's Entrepreneurial Journey and Getting Stuck

Adam Robinson

01:21>> That's really good. And then how many people are stuck right now? I mean, when I was stuck, and I still am, by the way. My hand is up. I was coming to these things all the time, like trying to figure out what to do next. So I've been on this entrepreneurial journey for eleven years, and I started this company that's now 22,000,000 ARR four years ago. And before that, I was stuck at 3,000,000 ARR for four

Stuck at $3M ARR and the Search for Answers

Adam Robinson

01:46>> years. I had a company called Robly Email Marketing in Ryan Allis's space actually. It was an email newsletter app. And couldn't get it going. There was this company called Mailchimp that was just decimating everybody. And look, the feeling of desperation in reaching for any type of information that would help me grow it was all that I was doing. I had this weird feeling of inadequacy like, is this the biggest startup that I can create? Right? Am

02:13>> I just a $3,000,000 guy? And there was a lot of frustration because I don't know everybody's experience whose early stage, but like I was stuck at this 3,000,000 number and then somebody would show up in my life that ran Facebook ads. And they'd be like, the solution for you is Facebook ads. I can get Facebook ads going. None of it would work, no matter what. Facebook, UX, UI, knew this, knew that, none of it worked. And

The Three Pillars of the Talk

Adam Robinson

02:38>> I'm gonna just tell you how I got unstuck. This company well, you could argue whether I'm stuck again now. But all of the lessons I learned along the way in doing so is what I'm going to share today. So let's start. The key pillars of this speech are going to be getting to 22,000,000 ARR bootstrapped in forty eight months. And then why I am now launching a new company. It's not quite a pivot because my team

03:04>> is still growing in that business. And then this whole thing that everybody talks about me, this LinkedIn thing. By the way, like five months ago, nobody would have said that about me and I wouldn't be on stage right now. So it's a really interesting thing that I'm like now the LinkedIn guy. But I'll talk to you about how I co created this product and go to market strategy that I'm doing now with this LinkedIn audience. So

Surviving the Plateau: $240K to $260K MRR

Adam Robinson

03:29>> number one, this is the journey and it looks good. But if you zoom in on some of the parts of this, it's not. Like, there are three stocks even in this beautiful graph of getting to 22,000,000 ARR bootstrapped in four years. So that sentence sounds really good. But I'm telling you, in Q3 2020 and Q4 2020 and Q1 2021, that is nine months of a really early stage startup when I was oscillating between $240,000 and

04:02>> $260,000 MRR. It really felt terrible. I'm not going to lie. I was over it. I thought I was going to start some other SaaS and I'll talk about that later. But look, this is my experience of the entrepreneurial journey. And it's one of the reasons that I advocate for bootstrapping because I think this is generally what people experience unless you have like the perfect product in a perfect market at the perfect time. And I don't know.

04:27>> If I were dependent on external funding for this journey,

04:33>> I don't know what I would have done a few of these times, you know. So when you're bootstrapped and you're trying to run a profitable business, when you get stuck, you have options. And a lot of times, if you're raising VC, you just don't. So I just wanted to share that that little piece of the journey. And then people always ask. It's like, man, bootstrapping 22,000,000 ARR in four years is incredible. But like, how did you

04:57>> go zero to one? You know, like, where did you even start? So and then when I tell how I got zero to one, it's how did you go one to 10? So first zero to one.

Zero to One: Facebook Video Ads Strategy

Adam Robinson

05:09>> I think Facebook is an incredible first thing that you can do to like spread awareness for your startup. I don't think it's a great later on thing for many people, but a lot of SaaS has to start. And I've heard Nathan say this. You start by selling something for $9 a month. And then you gradually realize that you have to just move up market as quickly as possible, and that is most people's journey. When you're selling

05:31>> something for $9 a month, you can sell it on Facebook. So taking it back to 2019, this was when, like, Snapchat was happening and, like, you know, Instagram stories were coming out. And I just, like, saw people walking around, like, doing, you know, doing this and taking these, like, amusing videos of themselves with interesting backgrounds. And I was like, you know what? Like, I wasn't even on social media, but I was like, I wonder if I

Weekly Amusing Videos with Helen

Adam Robinson

05:58>> can make a one minute amusing video every week that answered the sales questions of this product and have an interesting background. So me and my wife, Helen, tried that. And I was like, if I can get people anticipating these videos, then I've won the game. And like lo and behold, somehow it worked. If you wanna see these videos, my team won't let me put them in a playlist because they're so outrageous. But that's our our YouTube

06:23>> page. Scroll all the way down, and there's like 10 of them or 15 of them up. That worked incredibly well. And

06:32>> the interesting thing is, as I mentioned, I tried a ton of Facebook ads before. But the nature of this product and what I was saying was so interesting to people that these actually worked while the other face Facebook ads did not. So number one, the offer that you are making people is like the most important to making an ad work. The second thing that I learned and this is kind of a bit of an evil thing

06:56>> to steal Andrew's term. Our product has this just inherent privacy thing where we're de anonymizing people who hit your website, who don't fill out a form, and resolving it to a deliverable email address. There's like a small vocal minority who really, really hates this. So these ads were inflammatory to them. And they would just literally write like, you are a scumbag. Like, you should die. Like, they'd be like, you should die. And then from the brand

07:25>> account, I'd like make fun of their sweater or something. And and it just it was blew their mind that like somebody from a brand account would like insult you personally on Facebook, and they write back a novel. And that's what social social media wants. Right? So it like made these ads do incredibly well. And people like, oh, you're such an idiot for like, you know, torching a brand. Lesson two is like, you don't have a brand

07:46>> when you're zero MRR. Like, you can do outrageous things with zero consequence as far as I can tell. Like, the worst thing that happens is you just start over and everyone forgot what you were doing in the first place. So that was lesson number two. And then lesson number three, I think it's a big one for using Facebook in general to get your zero revenue start up off the ground. It created an unbelievable awareness for us,

08:08>> and it also had a really fast cash payback because we sold big plans and $9 plans. So, like, the dynamic was I'd run ads, you know, 100 people would sign up and basically churn 20% a month, and then one guy would pay us $5 and, like, immediately pay the ads back. So that was a dynamic. It was a great strategy to go from zero to one, but it really didn't last at all after that because that

Scaling to $12M ARR with Six People

Adam Robinson

08:28>> wasn't the people that we were gonna make a company building software for. So those are my three lessons from going from zero to one on Facebook ads. And then number two, this is a really interesting stage for me. And I I just loved running that business. And I'm like trying to do the same thing now because I loved running the stage so much. We got we actually got to 12,000,000 with six people. I mean, it's crazy.

Diana's Cold Email Machine in the Philippines

Adam Robinson

08:56>> And the core part of this was like the Facebook strategy had spread this awareness and the product was good and had some some kind of inherent word-of-mouth to it in general. And my co founder Diana was just running an outbound machine with five people in The Philippines. And she had these like untested, unscientific beliefs that you shouldn't use emails from Apollo or ZoomInfo because everyone's spamming them. And then you shouldn't use these automation products because everyone's

09:22>> using them. And how could something work that everyone was doing? Right? So like, I didn't have enough time to test that or tell her she was wrong. And like the price of this five person Philippines team is like, you know, $2,000 a month or something or 3,000. So that was what we were doing. They were spending half of their days doing lead gen, finding emails that were specifically not in ZoomInfo. So like, we build this

09:43>> in ZoomInfo and then cheat out these people go and find another email for these people somewhere else on the Internet. And then they were literally sending emails from her name is Diana Ross, which is interesting. But like dross, Diana r like whatever. They'd send a bunch of different emails from our Gmail accounts. And then when people responded, she would deal with them and get them on a demo and close them. So that was a really interesting

10:06>> cold email machine. And we're doing something different now because the cold email landscape has changed and there's just like pirate domain burning email strategy that you can do which email me and I'll tell you about it. But this was literally what the org looked like. And there's a few things that I want to emphasize here. With the right product and the right team, you can get a really long way with very few people, which I think

10:31>> it's really helpful to just internalize that because everyone wants you to have more employees. They just do. It's a really weird thing when you say you have six people and you think you're kind of far along at 12,000,000 ARR. And people are like, oh, that's cute. Like, you're just getting started. It's like, well, mean, I paid myself $4,000,000 last year, but I don't know. And, you know, it takes a lot of discipline to not add employees

10:57>> when you have traction. And kind of like what I just said, I truly believe this. It's so hard to do what we do. If you create a successful startup, I believe that you should make millions of dollars every year and not just be waiting for this maybe exit or maybe secondary that maybe will happen, but maybe will not, probably will not. That's just something that I believe. So, yeah. Everybody here, millions for everyone. Right? And I

Losing Discipline: December 2020 and the Jasper Story

Adam Robinson

11:28>> don't think you should have to sell your equity to do it. So, you know, I kind of thought that way at this stage and it was such a great phase that I'm trying to recreate it for myself. But then, I lost discipline. Like, why? Why would I ruin this beautiful life that I had? Because we're idiots, humans. Like, we are so dumb. What happened to me? So I'll take you back to December 2020. I had two

11:55>> startups. I had Robly and I hadn't sold it yet. And then I had started GetEmails, which is now retention.com. They were both 3,000,000 ARR. They both had six people, and they were both making a million and a half of free cash. So I had been sharing an office with the Proof team, which started Jasper AI for two years. This CEO Dave was stuck at 2,500,000 ARR. And I was like showing him these companies in our p and

12:17>> l and I'm like, Dave, I think the answer is we need to just have five of these. Because then eventually you have enough 3,000,000 ARR companies that are making a million and a half dollars. You're like living at Aspen or whatever. So Dave and I had this plan and my company GetEmails was the leader of the three companies that we had at $268,000 a month. Right? So this is outrageous. This is a text from Dave on 12/29/2020.

12:49>> It says, first paying customer had the idea seven days ago. Hopefully, this is my GetEmails.

12:57>> Does anybody know what happened one year later?

13:04>> So, like, this like, it's like heartbeat still gorgeous. Right? Like like, I have never seen I mean, despite raising money, I would like to do without. Like, I can't even explain to you what this was like. I was sitting on Brazos Street in this loft office with these guys. There were six of them on one side of the room, and then I was in a conference room on the other. And from January '21 to January of

13:26>> next year, they went from 100 to 50,000,000 ARR. Unbelievable. Right? So there's good and bad to this. You know, I'm sitting there with my one salesperson doing 12,000,000 ARR, and I'm like, this has got to be unicorn. How I you know, like, just need to try harder like these guys are because they raised a bunch of money from all the top tier investors. They started hiring these people that were like, so inspiring to be around. And,

13:55>> you know, one of this this guy, Shane Orlick had a meeting with me. He's like, I think he was at 8,000,000 ARR at the time. He's like, we're sitting in a conversation. He's like, what are your metrics? Like, no. No. He's like, that that is not acceptable. Like, what are you talking about? Like, we're making tons of money. He's like, you have one salesperson? Yes. Hire one more, please. You know? So what happened to me?

Chasing a Unicorn at $13M ARR

Adam Robinson

14:23>> At 13,000,000 ARR, I decided that it was my turn to try to create a unicorn. And thank God I didn't go out and raise money. But as I mentioned, at that point, we had just a ton of free cash. It was $6,000,000 $7,000,000 in free cash that I could spend on this, what would turn into a somewhat fruitless endeavor to pursue a unicorn. And if you just look at the before and after and how quickly that

14:49>> occurred, and if anyone's been a part of a company that did this the right way, you can imagine how terrible this was. Like, it it was so sloppy and we didn't have processes and, you know, I'm still only learning what that meant. But it was a very, very fast sprint to something that I felt we had to do. I was so confident it was going to happen, especially after the early indicators that we were getting from,

15:18>> you know, the sales we were doing and all the inbound and all the hype that I was creating that I decided to make a docuseries about it declaring in January that I was going to grow this company from 15,000,000 to 50,000,000 ARR, and I called it billion dollar challenge. We made $1,810,000,000 dollar episodes. And what happened?

15:35>> Not even close.

High Churn Reality in Martech and the Pivot Decision

Adam Robinson

15:40>> And why? Right? One thing that I just didn't get before, like, kind of a year and a half ago is that there are product categories within SaaS that are just intrinsically higher churn than other product categories in SaaS, especially in Martech. So the golden goose in Martech is systems of record, email service providers, CRMs. Right? If you're storing data from somebody, they're never gonna quit. On the exact opposite end of the spectrum is when you are

16:11>> selling leads to people, which is effectively what we're doing, or intent data, and you're trying to get them to pay you a SaaS contract. So we also added a bunch of expensive senior people with no processes. And the biggest mistake that I made, which I really, really regret and I will never do again. Please, if I do it again, just kick me in the face. I got FOMO and I started behaving like a VC backed company.

16:33>> What does that mean? I was like spending money on literally everything, losing all disappointment. Was setting a bad example for my employees. It was horrible. So what happened after that? Oh, yeah. Public service announcement. Don't make a show and miss by 50%. One or the other, guys. If you're gonna make a docuseries, don't miss by 50%. If you're gonna miss by 50%, don't make a docuseries. Simple lesson.

16:57>> So now we're pivoting to b to b and like really the reason why is and why I say I'm stuck again is this unbelievably high churn paradigm. And I'm talking like 60% gross per year. And then we have so much competition now that I was modeling an expansion revenue and it's just like a price war. So it's like the the the revenue retention is just as bad. But on the other hand, another reason I advocate for

Bootstrapping Advantage: Surviving Mistakes

Adam Robinson

17:19>> bootstrapping. This is our January p and l after the executives have paid themselves fat salaries. Right? You can make a horrible mistake if you are bootstrapping and still be in a beautiful place. Right? I'm not complaining. So why we pivoted to b and b b to b? Number one, I got this guy to come work for us a year and a half ago. If you wanna look at his LinkedIn real quick, he's a g. He is

17:41>> like the godfather of contact data. And the entire time we were growing this ecom business, he kept telling me, oh, Adam, you know, the leads are worth so much more to the b to b community. Right? So he was pushing like, as soon as the business got to the point where I could take my attention off it and so could he and we could start focusing on this b to b universe, we basically did. And then

LinkedIn Founder Brand and Content Pivot

Adam Robinson

18:04>> number two, I'm not gonna go into exactly how I do LinkedIn because that just wasn't what this presentation was supposed to be about. But I pivoted my content from trying to attract Shopify store owners to trying to attract b to b revenue leaders. And it's a little hard to see, but it's pretty obvious. Like, it it just 10x. And if you wanna see when that happened, that's my LinkedIn. And you can go back to Labor Day.

Cost and Structure of the LinkedIn Strategy

Adam Robinson

18:27>> Like, of last year is when I literally went from trying to attract e com people to attract b to b people. And it and and it's just the content. There was like a author product platform fit that just caused everything to take off. And by the way, I wanna say one thing. I'm spending a ton of effort and money on this. Like, the the consultant I use is $12,500 a month, but we're using it for four

18:51>> people. It's an integral part of our PLG. So I'm paying somebody who works with him $15 to manage outbound communication off of my profile and set meetings and move people along their journey. And I have a video element, and I have a filmmaker, the girl who made billion dollar challenge, and a video editor on staff. So it all adds up to, like, $50,000 a month and a ton of my time. But the output that what it's

19:14>> doing for us is just unbelievable. I'm I'm literally standing here because of it. Right? Like, it's just it's incredible. So what is novel about this? Has anybody read this book? I think it's the best book about building startups. That's a a link to it there too. It's little hard to see. It's a QR code. But we pivoted our content and didn't launch this product for six months. Customer discovery is building an audience either before or while

Audience-First Product Development and Waitlist

Adam Robinson

19:40>> you build the product. And I believe that this mechanism allows you to do the modern day four steps to the epiphany. We've had over 300 discovery calls. There are 1,600 people on the wait list. And my killer closer to LinkedIn posts is like PS, if you want to identify your anonymous website visitors and push their LinkedIn to Slack in real time, DM me. It's a 100% free. Not kidding. So you wanna do that? There's a QR

20:04>> code for that too. We'll call it action. So interestingly, because the megaphone was so strong, you know, I'm like obsessed with trying to create a startup that's not super high churn because I haven't done that yet. I was originally thinking we'd go after the, like, mid market because I kind of had this brand from LinkedIn. And typically, you can't start a startup in mid market because you have no brand. But I was like, let's go to

Free Product Offer and B2B Go-to-Market

Adam Robinson

20:29>> the mid market, have a sales led motion, try to go 30 to 50 k ACV, and then that would be a lower churn buyer persona. But this LinkedIn megaphone was so prolific that I was like, you know what? If I have an insane free offer, I'm and heavily influenced by this Mailchimp situation, it's gonna help me with this megaphone a lot more than it would help someone who did not. So now my the the the offer's

20:50>> insane. It's like if you use it, you talk to people about it. So I'm focused on trying to make incredibly viral products and have incredibly viral content. And it's just interesting how that evolved over time. So over the last twenty minutes, I shared how I bootstrapped 22,000,000 ARR in forty eight months, told you how and why we pivoted to b to b, and how I co created my audience with LinkedIn. And if you take nothing else

Closing Lessons and Key Takeaways

Adam Robinson

21:14>> from this talk, take these three things. You are not stuck. It just feels like you are. And keep throwing spaghetti against the wall. You never know how how big something's gonna get. I mean, Jasper thing to me was just like, I will never forget being a part of that even though it wasn't my company. And you do have what it takes to create a bigger SaaS. Like, when I was stuck at 3,000,000, I literally didn't know.

21:34>> And now I'm here and it's just it's something we can all do. So keep building.