Editor’s note: This is the third in a series of interviews from WRAL TechWire featuring “Legends – The men and women who helped create and build North Carolina’s technology and life science ecosystem.”  These leaders will join Jim Goodnight, Monica Doss, Dennis Daugherty, Charles Hamner and Venessa Harrison as members of WRAL TechWire’s virtual Hall of Fame, which named its first members in 2017.

Since this story was originally written sometime ago, Scot Wingo has seen GetSpiffy, where he is CEO, make several acquisitions and double in size, enter new markets and win a prestigious award from auto research firm, Frost and Sullivan. He stepped down as executive chair of Channel Advisor, the company he co-founded in 2001, but remains on its board. His 2019 Tweeners list added several more companies and saw a number of exits. He also podcasts regularly.

Paying it forward

The first time I interviewed serial entrepreneur Scot Wingo, currently CEO of on-demand car care company Spiffy, his border collie Mack greeted me at the door of AuctionRover. It was the year 2000 and AuctionRover was already Mack’s and Wingo’s  second startup.

Wingo had early exposure to both the world of the entrepreneur and to computers. His father, Dale Wingo, was a computer programmer and consultant in Aiken, South Carolina, where Wingo was born in 1968. “I had computers in my DNA and vicinity since I was born,” Wingo said, adding, “and I saw my dad as a startup guy.”

He says a lot of his own drive comes from growing up that way. “I remember dinner conversations where he would talk about a customer being unhappy and how to make them happy or how to solve a problem. I attribute a lot of my work ethic, drive, and curiosity to my upbringing and my parents.”

He adds, “I thought was cool that Dad could take his dog to work.”

A border collie. Pixabay photo.

One-third pizza, two thirds beer

After graduating from North Carolina State University with a Master’s degree in computer engineering in 1991, Wingo interned with a large company, then joined a startup in Connecticut. “I realized I loved startups,” Wingo said in an exclusive interview with WRAL TechWire, “but I didn’t like the cold weather.”

So, in 1995, he moved back to Raleigh and launched the startup Stingray with partners Aris Buineviscius and another friend from college, Dean Hallman. Stingray made developer tools for Microsoft  Visual C++. “It was sort of a precursor to open source,” Wingo explains. “We sold the source code with the software so developers could get in there and tinker with stuff. It was a fun company. We were developers selling to developers.”

The Stingray budget, Wingo quips, “Was one-third pizza and two-thirds beer.” Actually, however, the company grew to a $12 million run-rate in two years, “And we got offers,” Wingo said. It eventually sold to RogueWave Software for around $21 million in 1997. Wingo stayed on until 1999, but was unhappy with the direction RogueWave was taking, he said in news reports at the time.

Then, briefly between startup gigs, he was playing “With that web browser thing,” indulging his hobby and buying a lot of Star Wars collectibles from auction sites, including eBay, which  Pierre Omidyar founded in 1995.

That sparked the idea for Wingo’s next startup, AuctionRover, launched in 1999 to help people shop auction sites. “I was on these auction sites,” Wingo said, “shopping across sites manually, and I thought it would be cool to have a robot do it for me, so it turned into a business idea.”

Taking venture money for the first time

Early on, AuctionRover listed hundreds of auction sites, not counting eBay initially. It helped users find the best deal for a specific item. Its Morrisville offices reflected its origin. A Star Wars spaceship model hung over the receptionist’s desk and other Star Wars collectibles were prominently displayed. He has continued to collect Star Wars items, among other items.

A Star Wars X-wing fighter used by the rebels.

Founded in October, AuctionRover insured its success when it inked a licensing deal with eBay in December. That was a key differentiator from many of its competitors at the time, some in legal disputes with the giant site that controlled 70 percent of the auction business.

While Stingray had been bootstrapped, which included Scot taking on debt to run the company, AuctionRover, raised $3 million from marquee investor Draper, Fischer, Jurvetson and was in line to raise a great deal more and possibly head toward an IPO.

AuctionRover, then up to about 50 employees, began considering buyout offers. It finally sold to Pasadena, California-based GoTo.com/Overture, a web portal Wingo liked, in a stock transaction valued at about $175 million.

In  the rapidly changing Internet world of 2001,, Google began to compete with Overture. Although AuctionRover had developed software for eBay sellers, large companies such as IBM and Motorola had begun using it to liquidate overstocks. Overture was going to focus on competing with Google. So Wingo bought back AuctionRover for about $1 million and transformed it into ChannelAdvisor.

Launching an IPO

ChannelAdvisor raised about $90 million in venture backing, a sum Wingo said “Is miniscule by today’s standards.” The company connected to eBay and several other ecommerce sites and made a smart early choice to include the Amazon marketplace. “At the time, you could have made a valid argument that Amazon would never sell anything but books,” Wingo said. “We chose wisely, and things went our way. Ecommerce went our way and we were able to ride that wave.”

In 2015, ChannelAdvisor launched a successful IPO, something Wingo had been interested in for some time. “I remember talking to my father about it when Microsoft went public,” he said. “Taking a company public after 12 years was rewarding.” However, Wingo found that once the company went public, he wasn’t learning as much and missed one of his primary motivations: solving problems and scaling a business.

The company had brought on David Spitz as chief operating officer to help prepare for the IPO and after it went public, promoted him to president. He also wanted to be CEO. “So I kicked myself upstairs,” Wingo said. He remains executive chair of the board and a large shareholder, but “I stay out of the CEO’s hair.’

Ecommerce is “A fast-moving space and to stand in front of it is tricky,” Wingo said, summing up his experience in that sector. So far, every one of his startups has been in a different space and his next venture, the on-demand car care company, Spiffy, was a step into yet another sector.

Spiffy provides on demand car washes and detailing, and is adding other services, such as an oil change. It comes to the customer at work or otherwise. “Customers love convenience,” Wingo said, “So we focus on convenience. It lets them take the car off their to-do list.”

The next big thing?

“I think services are going to go digital,” Wingo said, pointing out that 80 percent of the U.S. GDP is in the service sector. “The question is how to deliver it economically.”

Exclusive: Spiffy’s Scot Wingo talks about doubling the size of his company overnight

While car care may seem an unusual choice for a technology entrepreneur, Wingo notes that “There is a lot of technology behind every customer experience at Spiffy. Everyone knows the front end app, but the technicians have a separate app on their smartphones and there is backend software orchestrating everything.”

About 100 Spiffy technicians currently serve about 400 vehicles daily, including trucks, in five cities at offices, car rental companies and fleets. “There are a lot of pieces to the puzzle,” Wingo said, “Knowing where the technicians are, the app telling which steps to perform, all with a lot of coordination on the backend.”

Spiffy raised a $7.5 million A round, and is growing north of 100 percent a year. “We’ve had three waves of innovation I was lucky to get my surfboard into,” Wingo said, “PCs with Stingray, the Internet with AuctionRover, and ecommerce with ChannelAdvisor. Next is service going digital.” Service areas he expects will go that route  include the house, the car, personal appearance, and maybe pets and loved ones, he said.

An avid reader

On a personal level, Wingo said his wife, Kristin, whom he once called “CEO of the house,” makes it possible for him to spend as much time working as he does.”Starting all these companies is an all encompassing thing,” he said.

He has three children, two in college and one in middle school. His oldest son, Sean, is following in his footsteps, studying computer science at NC State, although Wingo notes, “I didn’t push him to that, it was his choice.” His daughter, Dillon, is studying nursing. His youngest, Rory, is in middle school.

Wingo, far right, with his wife and children.

Wingo’s mother was a librarian and he said he’s an avid reader. He reads “A lot of science fiction and biographies “of founding fathers and billionaires.” He read Ron Chernow’s biography of Alexander Hamilton before the hit musical caused a Hamilton sensation and admits to being into “Hamilton mania.”

He also enjoys Walter Isaacson’s work.  Isaacson wrote a best selling biography of Steve Jobs, and Wingo is currently into his biography of Leonardo da Vinci. He avoids reading business books. “They get me so fired up I can’t sleep,” he said.

Wingo is active in the Triangle entrepreneurial ecosystem and remains bullish on its prospects. He blogs, does a podcast, and is on the Forbes Technology Council. Working in digital media has its pros and cons, he admits.

“The good thing is you get your message out there faster and the feedback is awesome. That’s also the worst part. You put an idea in social media and it comes right back at you at 80 miles and hour. You get instant feedback, positive and negative.”

Impact of co-working spaces

He adds, “It’s always surprising to me what captures people’s imaginations. It gives you direction on what to do next.”He sees a number of developments over the past decade as important to continuing the Triangle’s entrepreneurial culture.

Among them: the rise of co-working spaces such as HQ Raleigh and the American Tobacco campus in Durham. “These work spaces enabled a whole new cohort of startups to exist. They have done a ton for entrepreneurs and the Triangle. You see a lot of teams form up there. An engineer and a business guy start chatting over lunch and get together on a business idea. Magical things happen around the water cooler or at a beer party.”

He sees the Triangle’s “diversity” as an important aspect of its ecosystem. “We have a diversity of tech, biotech, software, edtech, agtech. We have a diversity of universities. We don’t have this old boy network you see in Silicon Valley. Our startup system is very open. It will let anyone in. I’ve mentored Tar Heel grads, painful as it is (jokes the NC State grad). We have a fair number of women-led companies. That diversity is what makes the Triangle special and I love seeing it reflected in our startups.”

He also credits the Goodmans of Capitol Broadcasting for their support of the American Tobacco campus, the Durham Bulls, and the Fox building. “It radiated out from there,” Wingo said,  helping transform Durham into a vibrant city attractive to recent grads and millennials with a growing national reputation that it is now.

Startup advice

One of his primary pieces of advice to startup founders is “Get a mentor.”

When he started Stingray, he connected with Richard Holcomb, a serial entrepreneur and venture capitalist in the  Triangle (currently executive chair of Cellarian, co-founder of StrikeIron, and also a farmer at family venture, Coon Rock Farm.)

“He spent a fair amount of time with us,” Wingo said, “and I asked, how can we compensate you?” He said, ‘Pay it forward.’ I was in my late 20s and it made a big impact on me. I’ve tried to live up to that.”

Another way, among others, that he does this is by maintaining a “Tweener” list of Triangle-based startups with at least 10 employees or a $1 million run rate, which get these scaling companies in front of potential executive hires and venture capitalists, who use it to optimize their time in the Triangle. “New York City and Austin can have Amazon and Apple,” he said. “Let’s grow our own $1 trillion megacap companies.”

“We need more Red Hats,” he said. The idea behind the Tweener list is to promote more companies to scale to $80 million and beyond. “It helps me focus on companies where I think I can help the most. Many investors come to the area and use it as a hunting list.”

2019 Triangle Tweeners: Investor Scot Wingo adds 31 firms to emerging stars list

These days, Wingo said, 99 percent of the time, you’ll find him at the Spiffy offices off Miami Blvd., and if you visit, you’ll likely be greeted by Kit, his latest border collie.

Back story: Why, how Scot Wingo turns startup Spiffy into a national car maintenance player