Do you remember when it was rare to have a computer at home?

For Scot Wingo, growing up in Aiken, South Carolina, having a computer wasn’t just a luxury—it was a unique advantage that would shape his entrepreneurial journey.

“We were the only people that had a computer in my town,” Scot Wingo said, “And not only do we have a computer, we had a mainframe in our house.”

This early exposure ignited Scot’s entrepreneurial spirit, leading him to set ambitious goals, including dreaming of owning a Lamborghini and even contemplating an IPO after reading about Bill Gates’ success.

In the latest episode of Founder Shares, Scot shared insights into his entrepreneurial ventures and the invaluable lessons he learned along the way. From his humble beginnings in Aiken to his journey through various startups like Auction Rover, ChannelAdvisor and Spiffy, Scot’s story is one of perseverance, innovation, and a relentless pursuit of his dreams.

His first venture, Stingray Software, was a bit of a wake-up call, though.

“We tried to raise venture capital, but we were really bad at it, me especially,” Scot said. “And that ended up being what we would call a bootstrap company.”

Despite facing numerous challenges, he persevered with the help of mentors who guided him through the rough patches. Whether it was navigating the complexities of raising venture capital or pioneering the concept of software as a service (SaaS) in the early days of e-commerce, Scot remained undeterred in his quest to make an impact.

“I’ve made every mistake in the book,” Scot said, “but fortunately, none of the mistakes have been company-risking mistakes.”

And from navigating the dot-com bubble to achieving his childhood dream of taking a company public, he still said that one of his most important jobs as an entrepreneur is to give back to the community. Inspired by the guidance he received from mentors and the supportive ecosystem of the Triangle region, Scot has made it his mission to pay it forward and support the next generation of entrepreneurs.

“It’s just part of our DNA in the Triangle,” Scot said, “and it’s what separates us.”

As we delve deeper into Scot’s remarkable journey, we uncover lessons that resonate with aspiring and seasoned entrepreneurs alike. Join us in this enlightening conversation as Scot shares his wisdom, experiences and vision for the future of the Triangle.

Don’t miss out on this insightful episode! Tune in to the Founder Shares podcast to hear the rest of the story, available wherever you like to listen.

The blog content should not be construed as legal advice.

Hosted by Trevor Schmidt, Founder Shares is brought to you by Hutchison PLLC.