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How a 21-Year-Old Student and Friends Acquired Their First Startup to Help Founders Avoid the Spam Folder

If you read Bootstrappers regularly, you’ll notice our stories usually trace a startup from its foundation to its first six figures (or more) in annual revenue. 

This meandering journey from zero to one richly rewards those who succeed. But with uncertainty hanging over founders like a sword of Damocles, few persist long enough to build profitable businesses. Many never even start. 

But what if you could skip the growing pains and go straight to profits? 

You might argue you need the bloody nose to know when to duck, but battles are won in the mind before the field, an idea exemplified by three young yet intrepid entrepreneurs: Roman, Alex, and Pepe.

Rather than starting a business, the trio pooled their expertise and resources to acquire one instead: Mailivery, a SaaS startup that leverages artificial intelligence to boost email sender reputations and increase sales by as much as 16 percent. 

Now, through their holding company Another Acquisition, Roman, Alex, and Pepe will test their entrepreneurial mettle as they apply past learnings to future growth. 

Will their gambit pay off? And how did it all begin? 

In Entrepreneurship, Age Is Just a Number

At 21, Roman is among the youngest founders I’ve interviewed, but he’s as curious and driven as someone twice that age. While studying Business Management and Digital Innovation at City, University of London, Roman interned as a sales development representative (SDR) at a contact center. Before long, he spotted an opportunity too good to ignore. 

“During the pandemic, I discovered LinkedIn as a sales channel, but I couldn’t find any easy way of tracking its performance,” Roman said. “I decided to found a lead generation agency using technology I’d developed to track everything we were doing, and that snowballed into me starting a software company, Dashed AI. I’ve learned more doing this than I have at uni.”

We’ve all been there: the moment you realize nothing edifies like real-world experience. While Roman got some much-needed context outside of the lecture hall, his friends Alex and Pepe worked full-time jobs in private equity. They began to wonder whether they could coax Roman into flexing his sales muscles on an acquisition of their own. 

“My background is in technology investing,” said Pepe. “I work for a financial institution on the digital side. We do lead partner (LP) stakes in VC companies and direct investments in the technology space. I’ve had exposure to different types of technology businesses, but specifically SaaS, which I thought would be a good fit for acquisition as it’s easier to scale.” 

Alex recognized the same opportunity. He and Roman had been friends for some time and often debated which startups would make great acquisitions in between uni assignments and cheap campus beer. With Pepe, another friend they met at university, they formed a formidable triumvirate of entrepreneurship, sales, and M&A experience. 

“Roman and I have been good friends for a long while,” Alex said. “I met Pepe through university, and we’ve always been aligned on our goals. Pepe and I come more from a financial background and Roman understands the technology and sales side. We wanted to combine our knowledge and create a powerhouse that acquires and grows businesses.”

Acquiring a Startup That Helps Founders

Roman had built Dashed AI out of necessity, but as customers flocked to his product, he began to wonder how much it was worth. Like many forward-thinking founders, he researched the acquisition market for similar startups to see what people paid for them. But when he stumbled upon MicroAcquire, what began as valuation research quickly became a hunt for synergy. 

“I’ve been a fan of MicroAcquire since I started Dashed AI,” Roman said. “It gave me a rough idea of what multiples I might get once my MRR scaled. I was curious about valuations and asking prices, but I also wondered if there was anything like Dashed AI in the space. I was thinking of partnerships and collaborations, but then Mailivery appeared in the search results.” 

Mailivery solves a problem that Roman had encountered with Dashed AI. When Roman founded his side project, his email address and domain had no reputation so his emails – even sign-up confirmations – landed in spam folders. Since most B2B founders rely on mass email campaigns to sell, a poor sender reputation means they acquire fewer customers. 

Mailivery’s algorithm beats the spam filter to help you sell more.

“Mailivery fixes a problem all founders face,” Roman said. “Some might not even know why their emails are bouncing or never getting read, and it’s usually because they’re landing in spam folders instead of their prospects’ inboxes. Mailivery solves this problem by creating realistic email conversations using AI that boosts your sender reputation, which is transformative – it could genuinely mean the difference between growth and stagnation.”

Mailivery’s price was right. It solved a problem Roman was familiar with, and it was SaaS. Was this the acquisition opportunity they’d been waiting for? With Roman still at university and Alex and Pepe working full-time jobs, they had to think long and hard about whether they could commit the time and effort the acquisition deserved. In the end, their ambition prevailed. 

“We needed to acquire our first company to know if we had the right instincts,” Roman said. “Any acquisition was always going to be a side project until it grew large enough for us to work on it full time. It was a risk, an experiment – a test of our abilities. If we scaled Mailivery, that would be our permission to acquire more companies under Another Acquisition.” 

A risk, yes, but a calculated one: “Mailivery made money, had customers, and was listed at an attractive price,” Pepe said. “Also, we’d been digging around MicroAcquire for some time and knew the acquisition process would be easier than if we’d gone elsewhere. The platform handles a lot of the legal stuff, so we could spend more time finding the right startup.”

Once the trio had narrowed down their search to Mailivery, they had to establish rapport and trust with Mailivery’s founder. “It was so easy to connect with the seller that we built a great relationship with them before making an offer,” Alex said. “They understood what we wanted to do, where we added value, which is reassuring when you’re passing the reins to strangers.”

Can You Bootstrap an Acquisition? 

Do you need capital to become an entrepreneur? A little seed money is helpful, but you don’t need millions or even hundreds of thousands of dollars. You’d be surprised what you can acquire for just a few thousand, which begs the question: Is it better to bootstrap your idea to market or acquire something small, proven, and profitable? 

“The classic bootstrapping route is to build an MVP, bring it to market, and then grow from there,” Roman said. “You’re worrying about product-market fit, what features to build, and how to attract customers. We wanted to skip those stages and get to the fun part, which, for us, is maximizing profitability using skills we learned elsewhere. They’re very different approaches.”

Both approaches need time and money. But most would agree that acquiring a company that’s already profitable is a simpler and faster path to success, especially when the startup and skill sets align. All Roman, Alex, and Pepe had to do was find a business whose weaknesses aligned with their strengths, that justified the risk of their experiment failing. 

“We used the MicroAcquire filters to get a list of SaaS companies with recurring revenue and then we focused on where we could apply our skills to accelerate growth,” Roman said. “Budget was also a big consideration. We’re three young guys and don’t have unlimited amounts of money or VC backing. Mailivery ticked all the boxes.”

Where did that budget come from? Credit cards? Loans? Mom and Dad?

“We used our savings,” Pepe said. “We didn’t get any outside money. We just pulled together what we’d saved over the years. Even with a modest budget, we still had plenty of startups to choose from on MicroAcquire. We just narrowed down our search and luckily could acquire Mailivery within that budget.”  

Two Weeks Later, Mailivery Was Theirs

In many acquisitions, aligning with a seller can take weeks. You might be going through an intermediary, for example, or playing email pingpong with time-wasters. But since MicroAcquire connects buyers with founders within a community-driven marketplace, the trio could pursue an open and collaborative conversation that might not have happened under other circumstances.

“The seller was a serial entrepreneur who’d started a bunch of businesses,” Roman said. “It’s great being able to have founders sell to other founders. It’s not like we’re a fund or they’re a fund – it was a really nice process. The seller had had higher offers, but as we had similar backgrounds and were committed to moving quickly, they appreciated that.” 

MicroAcquire promises sellers a letter of intent (LOI) in as little as 30 days. The next phase is due diligence, where the buyer audits the business to verify all is well before they and the seller sign the purchase agreement to close the deal. The whole process can take months, but Roman and his team acquired Mailivery in just two weeks – almost unheard of in the industry. 

“We signed the purchase agreement just two days after sending the LOI,” Roman said. “We sent the LOI on Friday, and then went to escrow, which finished the following Wednesday. Because we were buying a startup domiciled in Germany, we had to convert our pounds to euros, and with the conversion rate fluctuating, escrow took a little longer than we’d expected.”

Alex recalls the mad rush to finalize the deal, Zooming at all hours to draft documents: “I remember at one point I was on the floor at 3:00 AM outside my apartment in Paris. I had no internet at home and people must’ve thought I was crazy. We had to register an entity in the UK and then transfer everything over, which was a lot of work but we did it in under two weeks.”

How to Become What’s Missing 

Roman is happy to have already built a business from scratch. The skills he learned building the product and acquiring customers revealed where he might add value to other startups. When you become what’s missing, Roman argues, you expedite your return on investment. Identify where your strengths lie and then align them with a startup whose mission you believe in. 

“One thing I’ve learned being a founder is that I’m a bit of a salesman,” Roman said. “Mailivery was put on the market because they weren’t getting the sales. They had a sales strategy, but maybe they just weren’t salespeople. Being a founder developed the salesman in me, and I’m excited to help Mailivery grow because I know it’ll help founders like me succeed.” 

It’s easy to empathize with Mailivery’s founders. If growth stagnates and you’re at a loss on how to move forwards, often it’s better to pass the baton to others and start a fresh challenge. MicroAcquire is more than an acquisition marketplace. It’s also an entrepreneurial crossroads: an opportunity to switch lanes or move in a new direction.

For Alex and Pepe, who’ve participated in but not led private equity transactions, Mailivery’s acquisition is an opportunity to test their nose for good deals. “We’re learning a lot about how to scale businesses, how to accommodate bigger clients, and how to scale back-end operations,” Pepe said. “All of which we can translate into skills that we apply to other businesses.”

Start, and Learn as You Go

What’s extraordinary about these entrepreneurs is their ordinariness. Nothing about Roman, Alex, or Pepe suggests they’ve enjoyed any special advantage. They’re determined, ambitious, and unafraid of hard work: the raw materials of any aspiring entrepreneur. But what sets them apart from others who share the same passion is that they dared to begin. 

“We’re not the smartest guys in the world, but we’re very ambitious,” Pepe said. “We’ve got this vision for what we want to do in the future, and we’re doing it together as friends, which is lots of fun. If you’re wondering whether to do something like this, just go for it. Even if it doesn’t work out, you’ll learn a lot. Then you can start again without making the same mistakes.”

More people are turning to side projects to make ends meet or to chisel their way out of the office and reclaim some control over their lives. As the nation takes up the entrepreneurial mantle, Roman, Alex, and Pepe’s M&A experiment charts a new path to success. One that will hopefully prove lucrative for the fearless trio and those that follow in their footsteps. 

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