Tips for Startup Success from Serial Entrepreneur Scot Wingo


Serial entrepreneur Scot Wingo doesn’t have your average Silicon Valley credentials. He didn’t attend an Ivy League school, and he isn’t from a big city. 

Wingo was, however, raised by dad who was an early adopter of the computer. His dad even devised a program that was used to manage local carpet stores.

Throughout his prolific career, Wingo has achieved success by following his instincts and accurately differentiating between a fad and a trend that sticks. He jumped into E-commerce early with his launch of AuctionRover. Wingo predicted the explosive popularity of software as a service with his launch of ChannelAdvisor. Most recently, he foresaw the automation of automotive services and purchases and started Get Spiffy, which provides on-demand car care, in 2014. 

“I haven’t failed at a company yet, because I fail at it on a small level every day. Part of the entrepreneurial journey is doing a lot of testing and being okay with failing a lot, but you have to learn from it,” Wingo says. 

On Jan. 19, Wingo hosted a webinar for Founders Network where he shared how he achieved startup success over the last three decades. 


To learn more about achieving startup success, see if you qualify for membership and check out the webinar from January 19.

A Family of Entrepreneurs

Wingo’s father was an entrepreneur. He did computer consulting and devised a program that helped optimize inventory for local carpet sellers. 

“So, at the dinner table, we would talk about customer problems. I was trained to be customer-centric … Customer-centricity is in my blood,” Wingo says. 

He also internalized his dad’s work ethic. Wingo remembers his dad worked intense hours and always attended to work emergencies, even if it required cutting a vacation short.  

“As an entrepreneur, you have to have this kind of ridiculous, almost absurd, positive attitude. You keep hitting your head against that wall, and Don Quixote-like, you get back up and take another run at the windmill,” he says. 

Wingo’s Paths to Exit

Between Wingo’s four companies, he sold two, went public with one and is still working on the fourth. 

In terms of charting a path for each company, Wingo adopts a “dual path mindset.” He focuses on growing the business toward an IPO; if an acquisition opportunity comes along, he evaluates it. 

With Wingo’s first company, Stingray Software, an IPO was unlikely due to the company’s revenue ceiling. 

“That was probably my biggest mistake as a first-time founder, not understanding what a TAM [total addressable market] is. We didn’t even know to use that phrase,” he recalls. 

Wingo sold AuctionRover during the dot-com bubble.

When it came to Wingo’s third company, ChannelAdvisor, the company was initially not acquirable, due to its position in its market. Because it supported vendors like eBay and Amazon, competitors did not want to acquire it, as the acquisition would mean supporting market competitors. 

ChannelAdvisor went public in 2013. It was acquired by CommerceHub in 2022. 

The Future for Get Spiffy 

With his latest endeavor, car care service Get Spiffy, Wingo is acting on his predictions for the future of automation in auto products. 

Spiffy is not SaaS; rather, it’s a tech-enabled service or digital service. Using the company’s website, app or phone number, customers can schedule and pay for car care, including car washes, detailing and oil changes. Spiffy operates in 45 cities and has about 500 technicians and about 300 vans on the road each day. 

While some contend that service businesses don’t scale, Spiffy has been doubling for the last three years, Wingo says. In fact, a company in the auto care space was recently acquired for $190 million. 

“The theory that we had in 2014 that the E-commerce trends would replicate and look similar here in the auto world are definitely coming to fruition,” says Wingo. We’re on the surfboard, and the wave is starting to really form right now.”

During his webinar, Wingo covered:

  • eCommerce trends
  • The ground floor of SaaS
  • Pitching and scaling a digital service
  • Paths to exit

To learn more about achieving startup success, see if you qualify for membership and check out the webinar from January 19.

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