Gabby Rosen was skeptical of Nomad Cloud when she first saw it listed on Acquire.com.
The digital nomad newsletter was only bringing in a few hundred dollars a month. Its million-plus email addresses, all scraped from the web, were cold leads. If only a small percentage of them reported marketing efforts as spam, her account would get suspended.
Nevertheless, Gabby decided to acquire Nomad Cloud and grew subscriptions from 5,000 to 250,000 through cold emails to potential new readers. She also boosted engagement by 67 percent, turning the newsletter into a profitable, low-maintenance, ad-based business. Then she turned around and sold it on Acquire.com for 18 times her initial investment.
Gabby had an unfair advantage – she also co-ran Email Outreach Company (EOC), a firm specializing in high-volume, high-conversion email marketing. And when it came time to sell, Gabby managed to create a bidding war that doubled her asking price.
Keep reading to discover Gabby’s strategy for growing her newsletter and attracting buyers along with her three biggest lessons for aspiring entrepreneurs.
Turning a Passive Email List Into an Engaged Audience
By the time Nomad Cloud came across Gabby’s radar in 2024, she’d already spent three years as a digital nomad traveling around the US and Europe.
Along the way, she met Adam Rosen, a fellow entrepreneur who had already built and sold his first tech startup Door of Clubs, in 2019. Adam’s specialty was in cold email, and together with Gabby’s experience as an account manager, the two teamed up to build EOC, a business helping high-growth startups and Fortune 500 companies develop targeted email campaigns. Adam led product and Gabby partnerships.
EOC’s infrastructure afforded Gabby and Adam a distinct advantage with Nomad Cloud. They’d designed it to be capable of sending large volumes of emails using common techniques like rotating domains to maintain sender reputation and get around spam filters and strict privacy laws.
By doing so, Gabby and Adam were able to convert a significant portion of cold contacts into engaged subscribers. And their personal experience as digital nomads informed them exactly what to write to get their audience interested. The two were, after all, living the nomadic dream, running two successful businesses and living where they pleased.
Soon, with a growing audience and regular content, Nomad Cloud’s newsletter began generating steady revenue from sponsorships and partnerships. They eventually trained an employee to use AI-generated drafts that were then refined and proofread, allowing them to maintain consistent output with minimal effort.
And while Gabby claims most newsletter operators pay between two to four dollars per new subscriber, she says they were acquiring them for just a few cents due to their robust email system.
At its peak, Nomad Cloud was paying Gabby and Adam thousands of dollars per month while requiring only about an hour of work per week. It was the perfect time to look for an exit.
How Gabby’s Pricing Strategy Led to a Bidding War
After 11 months of ownership, Gabby and Adam decided it was time to sell. Instead of listing the business at a high valuation, they deliberately priced it lower than market expectations.
In her podcast with Andrew Gazdecki, Gabby explains:
“We purposely underpriced it to get more offers, which we knew would increase the price. I think most people do it the other way around, which can push the price down.”
Gabby also presented revenue and engagement metrics conservatively, leading to happy surprises during due diligence. For potential buyers, Nomad Cloud appeared to be an undervalued asset, prompting multiple competing offers.
“What’s the number that would take this off your hands today?” Gabby’s first serious buyer asked. That buyer ultimately doubled their initial bid, raising funds from investors to close the deal. In just three days, the business was sold for 18 times the original purchase price, effectively seeding their new business.
Three Key Lessons for Aspiring Entrepreneurs
According to Gabby, the first (and most crucial) step in buying a business is ensuring that the industry and business model align with your interests and expertise.
“For me, it made sense,” she says. “I’m a digital nomad, so I was naturally curious about the newsletter business,” she says. “It was something I found interesting.”
Gabby also saw Nomad Cloud as the perfect opportunity to refine her skills in email marketing, audience building, and digital media monetization. Instead of spending $10,000 on business courses, she suggests investing that money into acquiring an actual business.
“Be okay with losing that money, just as if you were just paying a business coach to learn those skills,” she says.
Perhaps the most critical lesson Gabby shares is that founders should leverage their skills, network, or competitive edges that others lack when buying startups. For Gabby, her advantages were her ability to craft strong pitches to attract large advertisers along with her and Adam’s shared expertise in mass mailing.
Gabby’s added benefit of having a SaaS project in the sales space cannot be overstated either.
Nomad Cloud had limited reach and no clear path to large numbers of new subscribers. Most founders would probably have found it prohibitively expensive to contract an email service like EOC with a startup of that size. However, Gabby and Adam were able to use EOC as a free internal tool and added thousands of dollars in instant value.
Now, with Nomad Cloud sold, Gabby is focused on growing the Email Outreach Company and helping clients scale their own newsletters. She also continues to monitor Acquire.com for new business opportunities and hasn’t ruled out acquiring and flipping another newsletter in the future.