SaaS Interviews with CEOs, Startups, Founders
Was my $22m ARR bootstrapped good enough? I felt pressure to be a unicorn, tried, and failed miserably
30 Apr 2024
Chapter 1: How did Adam Robinson bootstrap to $22 million ARR?
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This is our January P&L. We actually got to 12 million with six people. Well, I mean, I paid myself $4 million last year. Pirate domain burning email strategy that you can do. All right, 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? Come on. I mean, this is my experience as an entrepreneur.
It's just getting stuck and getting unstuck. So how many people have been stuck and gotten unstuck? 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, trying to figure out what to do next. So I've been on this entrepreneurial journey for 11 years.
And I started this company that's now 22 million ARR four years ago. And before that, I was stuck at 3 million ARR for four years. I had a company called Robley Email Marketing. in Ryan Alice'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? Am I just a $3 million guy? And there was a lot of frustration because,
I don't know everybody's experience who's early stage, but I was stuck at this 3 million 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 I'm going to 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 million ARR bootstrapped in 48 months. And then why I am now launching a new company. It's not quite a pivot because my team 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.
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Chapter 2: What challenges did Adam face while growing his company?
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 lo and behold, somehow it worked. If you want to see these videos, my team won't let me put them in a playlist because they're so outrageous. But that's our YouTube page.
Scroll all the way down, and there's like 10 of them or 15 of them up. That worked incredibly well. 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 Facebook ads did not.
So number one, the offer that you are making people is the most important to making an ad work. The second thing that I learned, and this You know, this is kind of a bit of an evil thing to like 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. 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 account, I'd, like, make fun of their sweater or something.
And it blew their mind that, like, somebody from a brand account would, like, insult you personally on Facebook, and they'd write, like, a novel. Yeah. And that's what social media wants, right? So it made these ads do incredibly well. And people are like, oh, you're such an idiot for torching a brand. Lesson two is you don't have a brand when you're zero MRR.
You can do outrageous things with zero consequence, as far as I can tell. The worst thing that happens, 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 startup off the ground. It created an unbelievable awareness for us.
And it also had a really fast cash payback because we sold big plans and $9 plans. So the dynamic was I'd run ads. 100 people would sign up and basically churn 20% a month, and then one guy would pay us five grand and 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 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 like a really interesting stage for me. And 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 actually got to 12 million with six people. I mean, it's crazy. And the core part of this was like the Facebook strategy had spread this awareness. And the product was good and had some kind of inherent word of mouth to it in general. And my co-founder, Diana,
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Chapter 3: What strategies helped Adam get unstuck in his entrepreneurial journey?
And, you know, we're doing something different now because the cold email landscape has changed. And there's this, 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 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 million ARR, and people are like, oh, that's cute.
You're just getting started. It's like, well, I mean, I paid myself $4 million last year, but I don't know. And it takes a lot of discipline to not add employees 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 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 startups. I had Robley and I hadn't sold it yet.
And then I had started Getemails, which is now retention.com. They were both free millionaire. They both had six people and they were both making a million and a half dollars 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 $2.5 million ARR. And I was showing him these companies in our P&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 million ARR companies that are making $1.5 million. You're like living in Aspen or whatever. So Dave and I had this plan. My company, Get Emails, was the leader of the three companies that we had at $268,000 a month. So this is outrageous.
This is a text from Dave on December 29, 2020. It says, first paying customer had the idea seven days ago. Hopefully, this is my Get Emails. Does anybody know what happened one year later? So it's like heart be still gorgeous, right? I've never seen, I mean, despite raising money, I would like to do without. 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 was six of them on one side of the room, and then I was in a conference room on the other. And from January of one year to January of next year, they went from $100 to 50 million ARR. Unbelievable, right? So there's good and bad to this.
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Chapter 4: How did Adam pivot from B2C to B2B?
August of last year is when I literally went from trying to attract e-comm people to attract B2B people. And it's just the content. There was an author, product, platform fit that just caused everything to take off. And by the way, I want to say one thing. I'm spending a ton of effort and money on this. The consultant I use is $12,500 a month, but we're using it for four people.
It's an integral part of our PLG, so I'm paying somebody who works with him $15,000 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 what it's doing for us is just unbelievable. I'm literally standing here because of it. It's just 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 link to it there, too. It's a little hard to see. It's a QR code. We pivoted our content and didn't launch this product for six months.
Customer discovery is building an audience either before or while 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 were 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 100% free. Not kidding. So you want to do that? There's a QR code for that, too. We'll call to action.
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Chapter 5: What lessons did Adam learn about Facebook ads for startups?
Interestingly, because the megaphone was so strong, I'm 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 mid-market because I kind of had this brand from LinkedIn, and typically you can't start a startup in the mid-market because you have no brand.
But I was like, let's go to the mid-market, have a sales-led motion, try to go 30 to 50K 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, and I'm heavily influenced by this Mailchimp situation, it's going to help me with this megaphone a lot more than it would help someone who did not. So now the offer's 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 20 minutes, I shared how I bootstrapped 22 Millionaire on 48 Months, told you how and why we pivoted to B2B, and how I co-created my audience with LinkedIn. And if you take nothing else 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 big something's going to get. I mean, that 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. When I was stuck at 3 million, I literally didn't know. And now I'm here, and it's something we can all do. So keep building.
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