Spiffy Founder Scot Wingo Discusses the Unique Set of Skills it Takes to be an eCommerce Entrepreneur

Welcome to this edition of Founder Focus, where we dive into the inside stories behind some of the most impressive entrepreneurial journeys. Founder Focus takes us on an intimate conversation with innovators and entrepreneurs and the great companies they’ve built. Host Steve Greenfield, CEO of Automotive Ventures, sits down with Scot Wingo, the founder of Spiffy, a technology-enabled on-demand service that allows consumers to request and schedule vehicle service and repair through a mobile app.

Spiffy offers on-demand carwash, details, and mobile oil changes. Wingo is a serial entrepreneur who successfully started four startups, creating hundreds of millions of dollars in value along the way. Wingo most recently exited ChannelAdvisor, which IPO’d in 2013, which is listed on the New York Stock Exchange. Wingo has received numerous awards including Ernst and Young’s Entrepreneur of the Year and Triangle Business Journal’s Business Person of the Year.

Transcription:

Steve Greenfield:
So with that, let’s welcome Scot to the show, Scot, how’s it going today?

Scot Wingo:
I’m good. How are you, Steve? Good morning. It’s good to see you again.

Steve Greenfield:
Good to see you. And thanks for joining us.

Scot Wingo:
Absolutely.

Steve Greenfield:
So tell us a little bit about the company.

Scot Wingo:
So started Spiffy in 2014. Really is just kind of an experiment to poke around with this kind of trend that I saw as an eCommerce person, as you mentioned in the intro, for 13 years, I started ChannelAdvisor, so 2001 started, went public 2013. ChannelAdvisor is in the eCommerce space. So we help brands and retailers sell on marketplaces like eBay, Amazon, Alibaba, etc. So we grew that from nothing to about, at that point of the IPO, about 100 million ARR. So I’ve been in the eCommerce world for a long time.

Scot Wingo:
And then I had my first Uber experience in 2011. And as an eCommerce entrepreneur, what that meant to me was, the light bulb moment was, I think we’re going to have, once you have that experience of using your phone and pressing a button and someone comes to take you somewhere, it’s so much better than a taxi or anything else that I thought this, once people have this experience, it’s going to be game over in every services industry. So therefore, all services will go digital.

Scot Wingo:
And then I have a lot of strange hobbies. One of my hobbies is I’m kind of an armchair economist, so I love to read about the economy. And when you study GDP, you look at the pie chart of GDP, consumer goods is about five trillion while consumer services is 10 trillion. So simply for me, we’ve seen eCommerce create trillions of dollars of value. Amazon’s a one and a half trillion dollar company now, for example. So I thought, there’s going to be a huge value creation event here when these services go digital, and how can I kind of poke around in that space, and that was the general idea of Spiffy.

Steve Greenfield:
That’s great. That’s great. Well, very exciting. Any surprises, I mean, from that initial interaction in 2011 till now, have you been surprised by the way things have played out faster or slower than you would have expected?

Scot Wingo:
Yeah, so some of it has been faster. So if you look at ride sharing, that has been just amazing, from that first Uber experience to where we are, that one has I would say surpassed all expectations. There’s still an open debate, is it a sustainable model and that kind of thing. As an entrepreneur, I kind of take a longer-term view of that, I think there’s so much demand that a model will be figured out there. But there’s also a bunch of naysayers that disagree.

Scot Wingo:
I would say the thing that surprises me most from that 2011, within the topic of digital services is, I still don’t have my electrician, anything around my house is still, I have to call a dispatch, and I still have that terrible customer experience of, here’s the delivery window, they missed the delivery window, I have no visibility, I’m completely put out by the whole thing. They show up, they have no idea why they’re there, they don’t have the right part. So I still feel like there’s a lot of work to do in the digital services space in general.

Steve Greenfield:
Yup, yup. A lot more innovation to come I’m sure. So there’s a debate around whether entrepreneurs are born or made. What’s your perspective, given you’re a serial entrepreneur, I would imagine the spark hit you fairly early. Do you consider yourself an entrepreneur that was born or did that happen at some point and what was the trigger?

Scot Wingo:
It’s hard for me to differentiate because my dad was an entrepreneur. He kind of likes to call himself the original geek, if you will. I’m from a little town in South Carolina called Aiken. You’re in Atlanta, it’s not too far away from Atlanta. So it kind of goes Atlanta, Augusta and then Aiken is right next to Augusta there. So just right on the Savannah River, so we’re very close to Georgia. Very small town, middle of nowhere, South Carolina. But I had a digital computer VAX in my house. For the younger folks, computers used to be big, these were like room size, picture four refrigerator sized cabinets in my house.

Scot Wingo:
So my dad was a software entrepreneur and he developed a system for carpet stores to a point of sale system, and then also, in the carpet industry, it’s very hard to optimize how you lay out the carpet in a house, so he developed software for that. I’ve kind of had entrepreneurship just kind of as part of my DNA since I was born I guess, or since very early days. I guess I was born with it. Our conversations at dinner were my dad talking about some customer problem, or he actually took me on several business trips to California when I was like 14 kind of a thing. I’ve been pretty, just kind of immersed in it for my entire life.

Steve Greenfield:
That’s great. So as you look back at your entrepreneurial journey or your multiple entrepreneurial journeys, what was the hardest decision you ever had to make as an entrepreneur?

Scot Wingo:
For me, when you start these companies, you put your heart and soul into it. And one of the hardest decisions is that exit, especially selling a company. So, I just kind of frame it a little bit. So I’ve had four companies, as you mentioned. The first one was in 95 to 98. So three years, called Stingray Software. Started that at zero, bootstrapped it, got it up to 12 million and sold it. And the second company was called Auction River, started that in 2000, sold it in 2001. So that was a short one during the internet bubble. And then ChannelAdvisor from 2001 to 2013. And then spiffy.

Scot Wingo:
Selling Stingray, my first company, I spent a lot of time talking to entrepreneurs about this because I think at the time you’re really excited to sell the company, but then you become like, any smart acquirer is going to keep you around for at least a year, many times now the standard is two. And you become kind of like, even worse than an employee. So as entrepreneurs, we don’t like to be employees basically. So now you’re an employee, which is okay, I guess, but you now get to see a front row seat of, most companies, most acquisitions don’t work out. Or even if they do, you’re going to see someone kind of dismantle the company that you built. And that’s the hardest thing to go through.

Scot Wingo:
I always counsel other entrepreneurs when they’re selling their company, you really need to make sure you’ve thought through the dollar signs part of that because there is this tail piece that can be quite painful. That’s the hardest decision I think. And then you have to be able to step back and say, is this the right thing for shareholders? Is my timing right? If you’ve created this asset over years and put your heart and soul into it, you want to optimize that asset. So there’s a lot that goes into that decision. That’s the hardest decision I think as entrepreneurs we make.

Steve Greenfield:
Not very many people get a chance to take companies public. What were the biggest learnings from that process?

Scot Wingo:
I just loved the whole thing. The whole thing from baking off with the investment bankers, choosing an investment bank, working with them on the S1 document, doing the road show, watching how the book develops, it was really fascinating. And then the day of the IPO, the pricing, the day of the IPO watching, we did the New York Stock Exchange because it does have a human component. The NASDAQ is pure machines, and the New York Stock Exchange is kind of a hybrid.

Scot Wingo:
So being there at our stand, doing a big launch event, everyone was wearing ChannelAdvisor paraphernalia. We had a big banner up where they ring the bell, I got to ring the bell. And then watching the pricing action as it started to open, all that was just, as an entrepreneur, I remember every second of it and that was just really amazing to live through all that and to do that. It makes me want to do it again.

Steve Greenfield:
As you look back, any regrets during any of these entrepreneurial paths?

Scot Wingo:
Hindsight’s 2020. So in my world of eCommerce, there’s a company called Shopify, I know you’re familiar with them. They basically do a pretty simple software as a service store. We had many opportunities to do something like that at ChannelAdvisor. And we kind of said, totally kind of a noisy space, high churn, not sure that we could be successful at that. Let’s go do some other stuff. So Shopify created like a, I guess they’re like a $50 billion company now from something that I didn’t think was a great idea.

Scot Wingo:
I also remember, I’m up here in Raleigh, North Carolina, and I’m a graduate, I did grad school at NC State, and we have a really rich engineering program. This professor came to me one day, he’s in computer science but he also studied ants, and he kind of said, “I’m going to create a robot and I’m going to put it in a warehouse and I’m going to turn all warehouses into robotics, and the robots are going to use an ant algorithm.” I was kind of like, whoa, this guy’s cuckoo for cocoa puffs.

Scot Wingo:
He started a company called Kiva, and sure enough, he built all that and then got acquired by Amazon for like 500 million. And I could have been like a very early angel investor, but I thought it was just a little too out there for me, and I didn’t really connect ants to robots.

Steve Greenfield:
But he did. There you go. Who was your most influential mentor?

Scot Wingo:
I mentioned my dad. Growing up with an entrepreneur in the house, there was a downside to that. So I can remember we went to some family trip somewhere, and my dad had a customer call, having a problem, and he had to leave in the middle of a family trip. That’s where you kind of learn, any startup runs on customers, and if you don’t put the customers first, you end up not having a business. So I definitely put my dad there.

Scot Wingo:
And then at NC state, I had a professor on the engineering side. And even at South Carolina, I had a professor, Dr. Pettis. They were kind of clandestinely entrepreneurial instead of the engineering. At that point in time, when you’re an engineer, your life’s going to be in a cubicle, here’s how you fit into these things, you’re a cog in the machine. So these guys were always like, well, you could be an entrepreneur.

Scot Wingo:
And then Dr. Tom Miller appeared NC State. He actually started a whole entrepreneurship initiative inside of engineering that’s gone campus-wide. I know down there, now it’s very much in fashion for every technical school to have a pretty deep entrepreneurial thing, like Georgia Tech has a really rich program there as well in Atlanta. He was a really good mentor about the pros and cons.

Scot Wingo:
You asked earlier, are entrepreneurs made or born? One of the things I find when I try to mentor, especially people that are coming out of big companies and thinking about entrepreneurship, is they really worry about the risk component of it. And one of the things Dr. Miller did that was really helpful was, he kind of explained, I remember going to him, one of my first, as I was graduating, I had a job at Motorola, and then one at a startup. And I was trying to think through that.

Scot Wingo:
His basically advice was, look, you go to the startup and if it doesn’t work, you’re going to have way more experienced than you would have gotten in, let’s say it’s two years at a big company. You’ll always have a big company option, but you’re going to learn so much at a startup, and there’s so much upside compared to, if you go to Motorola, there’s no upside.

Scot Wingo:
One of the things that was depressing about Motorola is they lay out your entire 20 year career in front of you in the interview process. And it was just kind of like mind numbingly. If you work really hard, you’ll get to be a member of technical staff eight and you can get to a hundred thousand dollars or whatever. So it was kind of like, wow, that’s actually kind of depressing that my whole life is, by signing up with you, my whole life is kind of essentially planned out. So he was really good at helping me think through that. Even today, I go to him for a lot of advice.

Steve Greenfield:
That’s great. That’s great. For the entrepreneurs or want to be entrepreneurs that are listening in today, what’s the best piece of advice you can give them?

Scot Wingo:
Let’s see. So, I have a pretty simple playbook, so I’ll just kind of give you a couple of pages of my playbook. Number one is, find a customer, solve their pain, and then go and solve more pain for them. It’s always easier to sell stuff to an existing customer than a new customer. The other one is, hire really smart people. When you’re in corporate America, it’s easy to hire smart people and then have them become your boss. So people tend not to. So you really can’t have that kind of thinking in a startup, you have to hire people that are smarter than you. Don’t be threatened by that. And then just unleash them and listen to them and kind of nurture them and get out of their way essentially.

Steve Greenfield:
If we fast forward five years and hopefully we have a good outcome for Spiffy, you’re public, and you can decide whether it’s the New York Stock Exchange or the NASDAQ. Post-Spiffy, what do you think you’ll be doing?

Scot Wingo:
I think Spiffy will be my last startup. I’m a real active member of the entrepreneurial ecosystem up here in the triangle. I created something called the Tweener list, which is where, what I discovered is, if we kind of split it up into like 20 years, the first 10 years, we just didn’t have enough entrepreneurs in our ecosystem. So, it was a lot of encouraging people, go ahead and take the plunge, start a company, you’re not going to starve, you’ll be okay kind of thing.

Scot Wingo:
And then the last 10 years, we have so much entrepreneurial activity, it’s been hard to focus on which companies to help scale. So I created a list called the Tweener list, which is companies over a million, kind of between a million at the bottom and then 80 million at the top. So it’s kind of a Goldilocks phase where if we can take more of the companies in our ecosystem here in the triangle and get them from a million to 80 million, that will accelerate the flywheel.

Scot Wingo:
So that’s what I really focus on when I’m not doing Spiffy is helping those companies in that cohort. And the list is so popular, I have this kind of, if I had more time, one of the things I would love to do is take this concept to a lot of other places because there’s, I just did it kind of selfishly so I could have a little list. And then if people move to the area, I could point them to great companies to go work for. But it’s ended up becoming much bigger than that. We’ve been doing events and it’s really formed a really nice community here, which I’ve enjoyed. So I think I’ll do a lot more around that in my retirement, if you will.

Steve Greenfield:
Well, Scot, thank you for joining us today. Really appreciate you making time and it’s great to dive in.

Scot Wingo:
Yeah, thanks for having me. I love what you’re doing for entrepreneurship. I think getting these stories out there is really important. The more we can help entrepreneurs, the better. So, I’m 100% supportive.

Steve Greenfield:
Great. Thanks, Scot. So that’s it for this week’s Founder Focus, our dive into the inside stories behind some of the most impressive entrepreneurial journeys. Please feel free to contact me any time. I look forward to catching up to discuss the industry. Thanks for tuning in for this week’s Founder Focus, and we’ll see you next week.


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