How Adam Robinson Bootstrapped 3 Multimillion Dollar SaaS Companies

Adam Robinson has a picture on his phone that belongs in a museum somewhere. It’s from early 2020, when his company, GetEmails, was making about $3m ARR.

In the picture, his friend Dave (also a founder – the two shared an office) texted him a screenshot from his Stripe account, along with the words, “First paying customer. Had the idea 7 days ago. Hopefully this becomes our GetEmails.”

That Dave was Dave Rogenmoser, that product was Jasper, and it went on to become the fastest-growing software startup of all time.

“I watched those guys do it,” Adam told me in a recent interview. “[I] came in every day and watched that happen.”

That’s not the only time he had an uncanny ability to pick iconic roommates. 

In the early-2000s, long before GetEmails, he shared an apartment in New York with Jake Lodwick – the first developer at CollegeHumor, and co-founder of Vimeo – back when the video platform was just a mockup in Dreamweaver. He got to watch that company take shape too.

Robinson had gone to New York to build a career on Wall St., a decision that worked out well financially for years, but left him searching for something more fulfilling.

“When you’re in a Wall Street sort of world, you can’t see out of it,” he told me. “But I had a glimpse into these people (Lodwick & co.) that were doing something totally different. I didn’t have vocabulary for it. But they were just getting a lot more out of it than I was. Now I know it's because they were building.”

Around 2012, he took the leap, leaving his job and starting a company with his brother.

Their first product, Robly, was an email marketing platform modeled on a recently-deceased SaaS product called, RatePoint.

“They just shut down out of the blue,” he told me. But they’d raised millions, and had a bunch of loyal users that were suddenly in the lurch. So he and his brother decided to build a replacement.

They caught a lucky break early on, when RatePoint’s founder, Neal Creighton, caught wind of their project, and offered to advise them.

“He wanted to see his vision carried out by someone,” Adam said.

So the brothers went to Boston, met him live, and he laid out a growth strategy that changed everything for them.

At the time, Constant Contact was the eight-hundred pound gorilla in the email marketing space. It was possible, Creighton said, to identify their customers by scraping websites for their forms (this was before the days of BuiltWith and similar tools).

“Then cold call those customers,” the plan went, “and get them to switch with a better-priced offer.”

They grew to 7-figures in their first eighteen months, and at one point had a group of almost forty salesmen working out of Adam’s apartment every day.

Bootstrapping a SaaS business to millions in revenue is impressive on its own. Even more-so for a first-time founder. By 2016, Robly was doing ~$3m in revenue, and profitable.

But there was a problem, and it was called Mailchimp.

As their initial outbound sales strategy dwindled, Adam and his team couldn’t figure out how to differentiate themselves.

“Mailchimp was amazing,” he told me. “They had this completely free offer at the time that was incredibly difficult to compete with.”

Indeed, that offer is now a classic case study for SaaS founders. Within a year of launching it in 2009, Mailchimp had 5X’d their user base from 85k to 450k. By 2016, a few years into Robly, Mailchimp had 16m users, and $400m in revenue.

Other email platforms, like Klaviyo or Convert (formerly ConvertKit), had made a place for themselves by tapping into niches that later blew up.

“Klaviyo made the best email app for Shopify,” Adam said. “Then Shopify grew from a $150m company to a $100B company over ten years… ConvertKit built the perfect tool for creators, and the creator economy sort of took off.”

But Robly’s angle remained elusive. He specifically remembers Thanksgiving that year, thinking through a marketing exercise, and coming to the same dispiriting conclusion over and over:

“I was like, ‘There’s not a single thing that I could say my business helps our target persona achieve that MailChimp isn’t better-suited for,’” he told me. “Like, if they knew about MailChimp, they should be using it.”

Rock bottom came in 2018, at the Traffic and Conversion trade show.

He and his team had spent an entire year building a new app, specifically designed for companies with large email lists. They were calling it Lead.com, and launched it at the conference with a big publicity stunt, to more or less crickets.

“I was just laying in bed with my wife, and was like, ‘I just wasted another year, probably spent a million bucks building this fucking software, and we’re gonna throw it away,’” he said. “Literally no one cares.”

On a whim, he decided to try one more idea.

“I had heard that you could get an email address from someone [on your website] who didn’t fill out a form,” he told me. “I didn’t know how to do it, but had heard it was technically possible.”

“So the next day, when I was pitching people, their eyes would glaze over, and I’d be like, ‘By the way, what if I could get you email addresses from people on your site who don’t fill in a form?’”

The feedback was instant and enthusiastic. People were suddenly asking buying questions.

Looking into it, he found that it was not only possible, but there was an additional benefit too – regulations barred players like MailChimp from offering this feature because of the way they sold data.

So he had a strong signal from customers, plus a mote from his biggest competitors. After three years of being stuck, he thought he’d finally found the feature that would help take Robly to the next level.

But in one of those funny twists that seem to define life as a founder, that too proved wrong. The feature was popular, but customers still weren’t using Robly for their email marketing.

Instead, they’d sign up, use the email-capture feature, download the list, and dump it into Klaviyo – a bummer for Robly, but an important signal on its own too.

“If they’re willing to endure that bad of a user experience, that’s a pretty good indication that you’re onto something,” Adam told me.

So the feature was eventually spun out as its own product called GetEmails (later renamed Retention.com), quickly grew to 7-figures in revenue, and Robly was later sold to private equity for $10m.

That brings us up to 2021-22, when Jasper.AI’s meteoric success led Adam to wonder if he might also have a unicorn on his hands with Retention.com.

There was something so relatable about watching his office-mates build a billion-dollar business. It seemed within reach.

By the time Jasper did their big $200m fundraise at a $1.2B valuation, Retention had grown to $12m+ ARR, bootstrapped, with just six employees. Jasper was spending a million dollars a month on ads. Adam wasn’t spending anything.

“I was like, ‘Maybe if I could spend a million dollars a month on sales and marketing, I’d be at $50m ARR too,’” he said.

He and his team started gearing up to raise.

“We talked to a ton of investors in ‘23, and the plan was to do a growth equity round,” he told me. “Thank god, the market melted down [before we could].”

What came next wasn’t easy – it included multiple downsizings of the team. But there are two reasons he’s happy they abandoned the unicorn path:

First, the raise might have killed his company. Turns out, they already owned more of the target market than they thought – big Shopify sellers ended up being their ICP, and most of the biggest were already customers.

And second, failing to raise has left him and his co-founder with an incredible, cash-flowing business that makes millions in profit every year.

“It’s a great lifestyle business,” he said. “One of the best I’ve ever heard of; which I think more people in tech should do.”

This has now become a big part of what he talks about publicly – encouraging founders to bootstrap and keep their independence.

The reason most don’t, he says, is because founders either fool themselves into thinking  their idea is too ambitious to build without funding, or more often, investors show up along the way, and try to sell the dream.

“They talk about the other companies they've invested in that have had unicorn exits, or whatever,” he said. “[But] you are not rich, if you raise at a $50m valuation, own half your company, and they let you take one million dollars off. Let me tell you, as someone who has children, that million dollars will last until your next round, and it will be gone. But they make you feel like you are wealthy.”

Even just the take-home pay of a boot-strapper, Adam says, often dwarfs that of VC-backed founders of much larger companies.

“To make as much as you would make if you bootstrap a $10m ARR [business] in a super lean way – which is so much easier than going this venture path – you would have to be the CEO of like, a $500m revenue company,” he said.

“There's a lot of reasons why that money gets so seductive,” he continued. “I've fallen victim to it a few times. I’ve been in that state of mind, and just wish I never had been. So I advocate for bootstrapping and founders maintaining their independence.”

Another silver lining of the 2023 fundraising attempt was that Adam and his COO realized that there might be a big opportunity for a product similar to Retention.com, but focused on B2B SaaS clients.

That led to RB2B, which launched early this year, and has grown to almost $4m ARR in its first eight months, making it one of the fastest-growing (perhaps the fastest-growing) non-AI SaaS products of 2024.

One secret to that growth is what Adam calls Inbound-Led Outbound.

He’s spent the last two years building a reputation and following on LinkedIn, and now uses that as the top of the funnel for his companies. The big difference between what he does, and typical “influencer marketing” is the system he built below the LinkedIn posts, to collect and qualify leads long before his BD team spends time with them.

It looks something like this…

Inbound-Led Outbound starts with activity designed to drive traffic back to your site – in his case, that includes LinkedIn posting, podcast appearances, and conference keynotes.

Then, they use their own product (RB2B) to get user-level insights on who’s visiting, and send AI-generated personalized outreach to high-intent prospects.

BDRs only manage people who are low in the funnel. That’s allowed them to use a leaner team, and also, BDRs are happier, since they only deal with high-signal prospects.

He’s laid out the details in several webinars (examples here, here, and here), and is more transparent than most – sharing revenue figures, conversion rates, growth charts, and more. All of which only serves to improve the flywheel, winning him more and more attention from other founders – perfect prospects for Retention and RB2B.

As he’s grown, he’s started to mentor other members of his team through the process of building an audience.

He also recently announced the $10m ARR Club, a group he’s launching that gives a handful of founders direct weekly access to him and his team, to learn how to build their own personal brands.

“Thought leadership only helps,” he says, “it never hurts. There is no situation in which it does not facilitate whatever you are trying to accomplish.”