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How the Freedom to Fail Led to Two Six-Figure Exits and Over $2 Million in Revenue for This Serial Entrepreneur

How often have you entered a store, fondled a product or two, and walked out again without buying anything? In Vietnam, if you were the first customer that morning, you’d portend a bad day’s sales. 

Shopify’s ecommerce entrepreneurs might not be so superstitious, but they know the pain of abandoned carts all too well. Serial entrepreneur, Joe Suh, thought he could eliminate this pain.

Joe began developing Shopify apps in 2016. His first app began as an experiment in big data sponsored by his employer. Overengineered and impractical, the app failed. Five years later, Joe’s second and third Shopify apps, Smart Facebook Messenger and WinBack, got acquired in six-figure deals. 

“I’d been working with some large Shopify stores on data projects,” Joe said. “When my boss suggested we build a Shopify app, I fell in love with the platform and started making apps on the side. The first few flopped, but over time, a couple took off. Over the past five years, I managed to grow them into pretty sustainable businesses that I eventually sold on MicroAcquire.”

One six-figure exit in five years is worth celebrating. Two would raise the roof. You might, therefore, spit out your coffee to know he’s already in talks to sell a third. Joe’s invested everything he learned with the first two businesses to create something so good, so patently sellable, he’s given up a comfortable, well-paid job to work on it full-time. 

“I left my day job for this third app,” Joe said. “It’s been in the app store for almost two years, and no one’s been able to copy it. I’m comfortable focusing on this 100 percent. Over the past few years, I’ve logged more than 10,000 hours making Shopify apps. Going back to Malcolm Gladwell’s 10,000-hour rule, I’ve spent enough time to know what works and what doesn’t.”

Or in other words: Do something long enough and you can’t help but get good at it. For Joe, it’s been helping ecommerce founders recover lost sales, automate their pipelines, and deliver enormous returns on investment. But the road hasn’t been easy in the Wild West of Shopify app development, as you’re about to discover. 

Not Your Average Programmer

Joe moved from Korea to the San Francisco area when he was just two years old. He recalls a childhood spent in the shadow of Silicon Valley, he and his schoolfriends riding the Big Tech express to giants like Intel, where Joe eventually won his first job. 

“I studied computer science at Berkeley, where I also got my MBA,” Joe said. “I planned on going down the technical engineering path, but then a few years into it, I realized I was more interested in the business side of things. And that’s when I started looking around to see how I could get involved in startups.” 

Joe’s interest in startups makes him an oddity among his peers. In Silicon Valley, graduates fight over limited places at giants like Twitter, Apple, or Google. Joe had already scored a lucrative tech job, but it wasn’t enough. He daydreamed about building a bootstrapped business rather than working for a bloated megacorp with money to burn. 

“I’m a Silicon Valley guy with a bootstrapped mindset, which makes me a fish out of water here,” Joe said. “The ethos of Silicon Valley is go big or go home, right? Raise a bunch of money and shoot for the moon. I love living and working in the Bay Area, but I’m very different from some of my friends who work for VC-backed startups. I like bootstrapped businesses.”

The Experiment That Changed Everything

Joe made the most of his time in big tech companies, switching from engineering to product management to product strategy and then back again. This breadth of experience fueled his curiosity in technology and how it creates economic opportunities. His big moment came in 2016 when his team needed a large data set to exploit a machine algorithm they’d built. 

“My wife at the time was running a Shopify store,” Joe said. “I thought ecommerce was a great use case for our machine-learning algorithm so I convinced my boss to sponsor the development of a Shopify app to see how our algorithms fared in the real world. For a year, we focused on abandoned carts and how to recover them with AI-generated texts and emails.”

Mention “abandoned cart” to a retailer and watch them wince. They cost the ecommerce industry as much as $18 billion each year. Recovering a modest chunk of these lost sales would return a smile to even the most cynical of vendors. Unfortunately, Joe’s app didn’t work. It needed time to gather data, and as recovery tanked, Shopify’s retailers pulled the plug. 

“Doing fancy AI machine-learning stuff didn’t fare well in that environment,” Joe said. “We needed an exploration phase to figure out what works, but these were real stores, real livelihoods. They told us recovery was getting worse, not better, and we’d try to explain that we needed more time, but they got impatient with us because we couldn’t prove the model.”

Joe needed a solution that Shopify retailers could install quickly and easily, and get immediate feedback. As Joe mollified frustrated retailers, Facebook introduced its Messenger chatbot and he wondered if he could ditch the fancy AI and instead send Shopify customers a recovery sequence using Messenger’s then-default opt-in.

“Before the Cambridge Analytica stuff kicked off, Facebook allowed a default opt-in,” Joe said. “We asked our Shopify stores to install a little plugin and about 90 percent of their customers who clicked ‘add to cart’ would then get automatically opted into an abandoned cart sequence. I think we were the first app developers on Shopify to figure out how big that was.”

The same retailers that had seethed at Joe’s earlier experiment rushed to install Smart Facebook Messenger. The solution was elegant, earning Joe around $40,000 per month at its height. But its success was short-lived. Copycats arose that hid the auto opt-in and customers complained of spam. Facebook pulled the auto opt-in feature.

“Facebook phased it out at first,” Joe said. “It made it default opt-out, but let us whitelist some of our stores as we were early partners. New stores would go through us and we’d petition Facebook on their behalf to get them whitelisted. But the writing was on the wall. We couldn’t send nearly as many recovery sequences after the changes and the app’s popularity waned.”

Build. Sell. Repeat.

Joe realized he couldn’t do much more for his first Shopify success and began speaking to business brokers about a possible sale. Weeks passed and no one bit. At one point, Joe had given up on selling when he noticed a new startup acquisition marketplace appear on the scene: MicroAcquire. Would he have better luck there?

Joe had also wondered how to recreate his Messenger success with another medium. Facebook might’ve made things difficult, but his business was still returning profits (although on a much smaller scale). If he could develop another way of delivering the recovery sequence, would he be even more successful? 

“I was just gonna let Smart Facebook Messenger die on the vine,” Joe said. “But then I found MicroAcquire, and it seemed a good place to sell where I could talk to buyers and be honest about the app’s limitations. I also started building a similar app for SMS. I took everything that had worked for Messenger and switched it to SMS, basically starting a new business.” 

Joe had pioneered Messenger as a medium for cart recovery, but SMS wasn’t as revolutionary. “The Shopify app store gets crowded quickly,” Joe said. “We were one of the first on Messenger, but copycats sprung up in weeks. It was the same with SMS. The Shopify app store listed 10 or 20 apps doing similar SMS marketing to us.”

Nevertheless, Shopify’s pie was big enough to feed Joe and the competition. Still, it wasn’t a big enough slice for Joe to justify leaving his job. That happened later, when he’d hit upon the idea of a third business and put WinBack on the market.

“In 2020, the Messenger app was on its way down and the SMS one on its way up, but I also launched a third app,” Joe said. “This one couldn’t be copied very easily. No one was doing it at the time and there’s no one doing it on the Shopify app store now. That’s when I divested of those two other apps and sold them on MicroAcquire.”

Two Million Dollars Later, Joe Quit His Job

Joe sold WinBack and Smart Facebook Messenger within weeks of listing on MicroAcquire. He’d sold a failed startup back in 2010 and remembers it as a slow, tedious process with little reward. But this time, he could speak to several potential buyers, even if only a few of those conversations became serious, and was able to connect directly rather than through a broker.  

“I had all these conversations in parallel at once,” Joe said. “It was over a one-to-two-month period, and I learned what buyers were looking for. I also established relationships with potential buyers of my other apps. I made friends with other people in the Shopify app ecosystem. So there were a lot of other benefits to listing the app on MicroAcquire.” 

Joe’s Shopify apps had generated around $2 million including revenue and acquisition proceeds. That’s a tidy sum for a four-year investment in side projects. But despite two exits, Joe never wanted to leave his full-time job until he was certain his next venture had legs. In 2017, his customers had inspired a new idea that he was ready to build in 2021.

“If I’m going to go all-in on something, I have to be super excited about it,” Joe said. “It needs to be something I’m willing to spend the next three to five years of my career on. My previous apps didn’t pass that Litmus test. But this time, I asked myself if I’d be willing to put in another 10,000 hours just on this and the answer was yes. And that’s why I’m pushing ahead.”

What was so special about this third app? Joe had listened to his previous customers and discovered a common theme: Admin was a time-sink and they wanted to automate everything from inventory management to customer responses. 

“You have thousands of merchants on Facebook Live selling everything from jewelry to clothing, and they’re doing it manually,” Joe said. “This third app automates all of that away, and I wouldn’t have known about this problem if it hadn’t been for the customers of my other two apps.”

Joe credits his past experience with Shopify apps for giving him the confidence to attempt a third. “All the trial and error was necessary to understand how the Shopify ecosystem works, how to make a good app, how to talk with customers, how to incorporate feedback. I think I got what I wanted out of those experiences.”

Despite being deeply entrenched in a landscape flooded with VC money, Joe needed the time and freedom to experiment. His side projects gave him the freedom to fail, and the income from his day job financed everything. You can’t get more bootstrapped than that. 

“Being employed is a great time to experiment on nights and weekends,” Joe said. “See what resonates with customers. Then once you get excited about something, that’s when you leave the day job – at least that’s been my strategy.”

Joe’s story might be atypical in Silicon Valley, but it sends a clear message to aspiring entrepreneurs: You might not be able to invest millions of dollars in your ideas, but you can invest time, and when you’re enjoying yourself, it hardly seems like work. Given the space and time to experiment, who knows what you’re capable of. 


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