Sean McCormick: A True Entrepreneur With Every Single Op

Jon Birdsong
See Profile
January 24, 2018

Today, when many people think of the word “entrepreneur,” there is a tinge of baggage. The age-old question at a cocktail reception of “What do you do?” responded with an “I’m an entrepreneur” will leave the questioner more perplexed than prior to asking the question. The range of entrepreneur goes from selling Cutco out of your parents’ basement to scaling billion dollar software companies.

This continuum presents even more questions.

The barrier to being an entrepreneur is much lower these days. True entrepreneurs see opportunity where others do not, and the best ones build amazing businesses out of them. Online stores have become copy-and-paste simple. Hosting costs are a fraction of the price they once were. T-shirt prints can easily be made for the masses.


That is where the entrepreneurial story of Sean McCormick starts. Who doesn’t love making T-shirts? From T-shirts, the journey traverses through a 6 year MBA, dipped with a funded startup in the automotive space, and out the other end with a thriving CRM and field service SaaS business.

We meet Sean in his new SingleOps office on the west side of Atlanta, in the aptly titled, Lumberyard Lofts. A Mexican restaurant with graveyard flair is a stone’s throw away from the new SingleOps HQ. As I knock on the windowed-door to meet Sean, I’m immediately introduced to the unofficial office mascot, Reggie, a blonde German-shepard, husky, and lab mix.


After a tour of the office and introductions to the team, we settled in for what planned to be 20 minute interview, but turned into 90 minutes of storytelling, lesson sharing, and good ol’ fashioned reminiscing.

Back to T-shirts.

The Early Days: ViralPrints

That’s where we’ll pick up SingleOps CEO, Sean McCormick’s story in 2007 -- his junior year at Northwestern University in film class. A professor-provoked idea turned into a full-fledged business selling T-shirts. In class, the professor explained how much more revenue was generated on merchandise than the actual movies themselves. Mixed with his New Media class and relentless YouTube exposure, Sean put two and two together. Eventhough YouTube had only been out a few years, viral videos were picking up steam with classics like “Charlie Bit My Finger” and “Chocolate Rain.” Many viral video sensations began selling shirts but had clunky store fronts and poor operations. Most didn’t want to streamline T-shirt manufacturing, they wanted to create amazing videos.

Seeing this gap in an rapidly growing market, Sean started ViralPrints. Traction was quickly gained as viral video creators provided easy access and a willingness to sell more T-shirts. The video creators were more than open to the idea of selling more merchandise with less hassle. Prior to YouTube doing any ad revenue share, merchandise was the main way to make money. ViralPrints took off. Their specialized e-commerce technology, catered specifically towards viral video owners published on YouTube, made for a profitable start as an entrepreneur.

In the early years, ViralPrints was making hundreds of thousands of dollars a year. Then, the team of three went through some life changing events. The lead engineer, still in highschool at the time, headed off to college and works in Silicon Valley today. His business partner ended up attending Emory Law School after undergrad. The market was heating up with well-funded leaders like Spreadshirt and Teespring, but the economies of scale for ViralPrints were not as seamless as originally predicted. Sean was left with an always difficult, but must-make decision: spend less time on ViralPrints and focus on a new venture.

JB: When did you know ViralPrints was not going to be a $100 million business?

SM: We could have pivoted ViralPrints into a real competitor against companies like Spreadshirt, but it just wasn’t worth it. The core team was getting their law degree at Emory or undergrad degree at Brown. We would have had to really rebooted a lot. It did not make sense to pivot into a vertically integrated solution, which would include physical printing of the shirts. It would be like starting from scratch, and quite frankly, I was burnt out. When I look back at ViralPrints, I look at it as a missed opportunity. My biggest mistake was not focusing on growing the team, instead I tried to get the most out of the team with the limited resources we had.

Leveraging What He Knew, Paired With The Start of a 6 Year MBA

ViralPrints was put on the back burner, and Sean began leveraging his deep industry knowledge with YouTube influencers at an Advanced Technology Development Center (ATDC) startup called KontrolFreek. His six months in marketing at KontrolFreek allowed him to develop as an entrepreneur under Ashish Mistry and add immediate value to their partnership marketing strategy. All the while he continued to network with Atlanta’s entrepreneurs and investors in and around midtown, years before Atlanta Tech Village. Sean also wanted to hedge his entrepreneurial ambitions with an MBA from Georgia Tech. It was an incredibly friendly program for an entrepreneur who was working on campus (ATDC is in Tech Square which is on the edge of Tech’s campus). After the first year, Sean took a hiatus to start a few more ventures before graduation, but recently completed the final few classes to earn what he calls “a 6 year, full-time MBA.”

“I’ll proudly place the diploma in the SingleOps office when it’s ready.” he says.

With the first year of his MBA complete, an internship was the natural course for the program. Instead of interning, Sean met an investor in Tech Square who had an idea and seed capital to start a company in the auto industry. Enter Fat Joe’s Cars.

“The investor sold me on the idea and I thought it was a great idea.” Sean shared.

Fat Joe’s Cars Pivots to Driverly

Mid MBA, Sean had an idea, an investor, capital, and a real problem to solve. Fat Joe’s Cars was an online dealership for cars. Before you think AutoTrader, know Fat Joe’s Cars’ vision was to be the end-to-end solution for the dealer, where AutoTrader is a robust listing of cars. The realized vision of Fat Joe’s Cars is what Carvana is today -- which included $300 million raised and superb execution. Sean saw the writing on the wall, and knew the initial vision of Fat Joe’s would be capital intensive and pivoted the business to Driverly.

The long term end-to-end solution for the dealer was still the goal, but a new go-to-market strategy that required less capital became Driverly’s focus. Instead of raising millions of dollars to build the online infrastructure for dealers, they focused on one core problem for the consumer: “What is the best way to sell your car?”

Answering this question was going be the sticky, viral consumer play that would eventually lead to revenue through dealership partnerships. Aggregating and analyzing numerous proprietary data sets most dealerships purchased, mixed with public buying trends and places to sell your vehicle -- all while layering over a consumer friendly way to answer the question: “What is the best way to sell my car?” was Driverly’s initial value prop.

Starting 2012, Sean had whipped together a great team, with veteran advisors, in an exciting market, on a shoestring budget -- spending less than $100,000. He had engineered enough value that an extended warranty company was very interested in investing in Driverly. On the 11th hour, however, the deal fell through for many reasons.

It was soul-crushing. They lost momentum. Key advisors left. Money ran out.

Soon after, Sean shut the business down.

JB: What’s one key learning from Driverly?

SM: Focus on one idea and treat your brand as a sacred valuable.

JB: What’s a key learning on fundraising from Driverly?

SM: Raising money in a non-competitive market is tough. When there is just one person who’s looking to invest, the dynamics do not favor the entrepreneur; there is no leverage. Overall, it’s still important maintain good relations with investors, assuming you like them, and they align from a value and personality perspective.

JB: Do you still own Driverly.com domain?

SM: Oh definitely. I get hit up weekly for the domain. It’s one luckily purchased for $10.99 on GoDaddy, and recently I was offered $7k for it. I’m going to keep it for a bit longer and see where it goes.

JB: Where was the best place to network with entrepreneurs -- was it one particular event?

SM: Unquestionably, the best place to network was in the hallways in-between coffee refills and bathroom breaks. I would run into great entrepreneurs like Andrew Ibbotson, who is still a mentor of mine, and they’d offer the support and inspiration to start and build.

These are the stories that rarely get told at the cocktail party when the answer to your occupation is “I am an entrepreneur.”

Five years since starting ViralPrints in his dorm room, Sean had gone through two companies, three different names with five or more pivots, raised money, built teams, pushed product. All while in the middle of his 6 year, full-time MBA.

SingleOps Is Spawned

Undeterred by previous scars, Sean got back in the arena. He started first with people in 2013. In this case, it was with his friend and mentor, Matt Lowe. Matt is the CEO of SwiftStraw, an Inc 5000 company that is disrupting the pinestraw industry. Sean had known Matt for years and respected his work ethic, values, and business acumen. Matt and Sean had been getting quarterly coffee together over the years since his returned from Northwestern.

A friendship soon turned into a 6 month consulting gig for Sean and SwiftStraw.

The consulting gig was focused around finding a better system to run and operate a landscaping business. Traditional CRMs that many of us think of today, like Salesforce.com, were not built for landscaping businesses.

Matt said about the consulting project, “if you can’t find a good solution, would you be interested in building one?”

Sean replied, “Absolutely.”

Sean worked out of the SwiftStraw office for 6 months. In the first couple of months, he realized there was not a good solution. He participated in demos with dozens of potential vendors, and none of them fit the needs of SwiftStraw. At the time, they were using Salesforce.com and customized it dramatically to fit their needs -- but as the business grew, they needed more. Example features included scheduling, obtaining field data, job costing, route planning, time tracking, and much more. Sean quickly learned managing a field workforce required a unique set of tools.

After two months of research, Sean got some of the band back together, including his lead engineer from ViralPrints, to start building. Mixed with Matt’s infectious enthusiasm and vision, SingleOps was born. At the end of the 6 month period, the Minimum Viable Product was built. SwiftStraw was their first customer, and they had 10 more who were providing feedback on what features to build. One key go-to-market benefit, unique to this industry, was the tight-knit web of contractors and subcontractors. If a product is valuable, customers will share it.

Through Matt’s reputation and industry relationships, finding the first 10 paying customers was a quick email or ride-along away.

The product became so desirable to SwiftStraw’s circle of vendors and contractors that Sean was able to pre-sell deals under the assumption that they would build a particular feature, knowing it was applicable to hundreds of other potential customers. There were even two deals valued at a total of $25,000 that he was able to sell before the product was even built!

JB: Were there existing competitors that SingleOps faced on day one?

SM: There were competitors out there, but no one I was speaking to or any of their friends were using them. This let me know there is a huge opportunity, as this industry is gigantic.

JB: How did you know the product was a “need to have” for the first customers outside of SwiftStraw?

SM: A ton of meetings with potential customers. A lot of educating and updating. They also saw how well SwiftStraw is run from an operations perspective. This was a key selling point. Those first customers knew how well SwiftStraw ran their operations, but it was only after they understood how they did it, that the product become a need to have. Also, in our market, we were talking with leaders that were the most forward thinking from a technology perspective. This is proven because one of the customers was thinking about building their own solution.

One other big factor that made our product a “need to have” in the market was after diving into the market, there had been rumblings in the industry for years about how a product like SingleOps needed to be built -- which is a fully integrated solution that connects your sales to your backoffice to your field workforce in a simple, easy-to-use software product. Lastly, the final piece that made it a need to have was the compelling event. Many of our customers have had steady growth over the past few years, but every one of the CEOs wants and believes they can grow faster and be more productive. The smart and forward thinking CEOs know that technology can help them make that productivity leap and grow the business by working on the business.

Many of our customers have been building their business for the past 20 years. That’s 20 years of getting the right people in place and the right processes in place. Now they are realizing technology is the greatest area of opportunity to improve that will grow their business. Overall, a cool, simple, easy-to-use product had to come down to dollars and cents backed by a reputable and proven story of success (SwiftStraw). These factors made it a must have for the early adopters.

JB: A 6 month consulting project turned into 2 months of research and 3 to 4 months of building a minimal viable product, yet you’re selling a fully integrated suite of features including CRM, scheduling, backend integration, and more. How did you prioritize which features to build first?

SM: Ha! I wish we would could have built all of that in 4 months. What SingleOps does now is not what I said it did back in 2013. We started with scheduling. This focused our attention much more on the backend office piece. The very first version had no CRM, no sales tools, or any of those features. At that time, we were thinking that SwiftStraw would still use Salesforce for the CRM piece and we’d just integrate with it. So our first few “killer features” were: 1) scheduling 2) being able to send a proposal 3) syncing with Quickbooks. Back office operations is where we started.

JB: How did you convince a company who’s been doing the same thing for 20 years to change their ways?

SM: We just kept telling the SwiftStraw story. We told it over and over and over again. But let me also be clear, SwiftStraw’s team didn’t completely embrace SingleOps at the start. It takes time, belief, and salesmanship. The golden hammer was SwiftStraw’s reputation and results in the industry. People want to be on the Inc Fastest Growing Companies list like SwiftStraw.

2013 was a year of learning and building for Sean and the SingleOps team. He believes that 2014 was the year SingleOps truly began. It was no longer a consulting project -- they were incorporated and hired their first employee. It was then that they built the first version to take to market, not the MVP version they had built for SwiftStraw. Of the first three companies they had developed relationships with, two of them bought it, implemented it, and succeeded. Even today, that one company that passed is still using an old Microsoft Access database. Sean and his team have let that business know that they will be standing by when they are ready to make the switch.


JB: When did you start thinking to yourself that SingleOps could be a very successful business?

SM: It was in the earlier side of 2014. The amount of market response we had was phenomenal. Potential customers were searching us out and word got around that we were building this product. But there was never a singular moment where I thought, “SingleOps is going to be successful.” It was more of a gradual feeling. What motivated me through hard times was seeing the success of our first customers, SwiftStraw. Also, the market played a big role because we were having 5-10 new conversations a week with potential customers. That constant interest will fuel your growth. Two years later, the companies that didn't like us at the beginning, because they preferred pen and paper, are now saying "now we get it.”

JB: Did you enter an existing market or did you create your own?

We entered an existing market which was “Field Service Software” but Field Service Software didn’t have all of the components we’re offering or going to offer. Companies who traditionally adopted field service technology were HVAC technicians or pest control. There was a large category of field service customers who used that type of software before it was available on the smartphone, or was even really user friendly, like SingleOps is today (smiles).

Developing the Product and Processes

2015 was all about the product -- actually building what Sean and the team promised their current and future customers. Because the platform is a fully integrated solution with many bells and whistles, it took a year to build out everything the five to seven early customers wanted. They had a long list of pre-customers, but now they were in every entrepreneur’s ideal spot: if they build it, they will come (and pay). The team included two contract engineers, one full-time time engineer, and Sean. Introducing the CRM features really made it sticky for customers, because it transitioned their entire workflow into SingleOps.

Early 2016, SingleOps raised their first round of small capital (less than $200,000) from SwiftStraw and Matt Lowe. The first customer became the first investor and in turn, continues to be one of the strongest sales resources today. Around the same time, SingleOps hired their first go-to-market employee: a jack-of-all-trades sales and marketing team member. Focusing on the product for an entire year before hiring the first sales rep was critical to making sure there was repeatable, customer acquisition model.

2016 was spent getting to profitability, which included Sean compensating himself enough to pay rent and cover the basic costs of living,which is still his modus operandi today, even after raising a $1 million seed round. SingleOps’s great success in the middle of 2016 was achieving product-market fit. He knew they’d reached it because they were able to sell large ($20,000+) deals to non-friendly customers. The customer base was no longer companies in Atlanta who knew Matt Lowe and the SwiftStraw story. Another indicator was their first six-figure deal, which occured in 2016 as well.

Peyton Turner,  SingleOps  - Sales Development Manager

Peyton Turner, SingleOps - Sales Development Manager

Product-market fit is a huge accomplishment for every entrepreneur. Yet, Sean knew the bigger question to answer: “Can we create a repeatable customer acquisition model?” Just Sean selling deals was not repeatable. To answer this question, Sean hired a full-time SDR, along with 4 student interns to set appointments. Between the full-time sales hire and the interns, they were able to fill both Sean’s and the recently promoted AE’s calendar with demos. They closed more than 20% of those demos. At the average price point per customer, Sean knew he had achieved a repeatable customer acquisition model.

Growing at a strong clip and defining a repeatable customer acquisition process, Sean had no plans to raise money in 2017.

JB: Why did you raise money from Atlanta Ventures?

SM: It was in early 2017, I went to a panel discussion at ATDC that included David Cummings. The title of the panel was“Should Entrepreneurs Raise Money or Bootstrap?” The panel actually looped me into the discussion, because of where we were with the business, and it was a question I kept going back and forth within my mind.  I had met David in my ViralPrints days and would periodically email him questions and proactively send him my one-page strategic plans. That consistency and persistence was key, especially after failing a couple times.

After the panel discussion, we set up time to meet together. David saw our progress and the bigger vision of SingleOps for the next 5-10 years. In May, we raised a $1 million seed round to increase the repeatable acquisition model and improve the product.

The Journey to The Magic Number

Sean and his team are on the cusp of reaching the magical $1 million ARR number.

When walking into the SingleOps office, it doesn’t feel like a shiny new startup with hopeful growth plans. It feels like an established software company with a solid business model in a large market, run by an entrepreneur with his fair share of battle scars, rightfully and proudly worn.

The next time Sean McCormick is at a cocktail party and someone asks “What do you do for a living?” and he answers “I am an entrepreneur,” we’ll all know what that means.

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