Scot Wingo. He’s the CEO of Spiffy. He’s also a 4-time serial entrepreneur and industry thought leader in ecommerce and on-demand economy realm. He’s appeared on CNBC’s Today’s Show and contributed his expertise to The Wall Street Journal, New York Times along with many other publications. He previously founded Stingray Software which he sold to Rogue Wave Software, AuctionRover which was sold to GoTo/Overture, and ChannelAdvisor that went public in 2013, under the stock symbol ECOM. Famous Five: Favorite Book? – The Hard Thing About Hard Things What CEO do you follow? –  Jeff Bezos Favorite online tool? — LinkedIn How many hours of sleep do you get?— 4-6 If you could let your 20-year old self, know one thing, what would it be? – “To trust your instincts and invest even more in your own companies”   Time Stamped Show Notes: 00:44 – Nathan introduces Scot to the show 01:29 – Spiffy is an on-demand car wash and detail company 01:33 – Customers pay for car washes and Spiffy is full-stock 01:59 – Spiffy is a pay-as-you-go model 02:02 – Some customers would request to have their car cleaned on a regular basis so they’re currently working on a subscription plan 02:30 – Having your car cleaned is addicting 03:02 – Spiffy started in 2014 03:17 – Scot was 46 in 2014 03:26 – Scot loves building a company 04:00 – In 1999, AuctionRover started 04:14 – AuctionRover is a search engine for auction sites 04:16 – Scot always had a plan to develop software for sellers 04:20 – After getting acquired, they developed the software which turned into ChannelAdvisor 05:43 – They’ve raised $3M for AuctionRover 05:53 – AuctionRover started to get acquisition offers 06:16 – Scot was a fan of Goto 06:45 – Stingray put Scot in a position where it had to work 07:32 – Scot had accumulated personal debt to run Stingray 07:55 – Scot was 25 when he founded Stingray 08:03 – Scot had Stingray for 3 years before selling it to Rogue 08:11 – Acquisition price was around $7M 08:27 – It was software and Scot had a 30% margin 09:07 – Scot added $3M through fundraising 09:55 – Tim Draper was on Episode 129 10:17 – AuctionRover’s acquisition price was $20-50M 10:43 – The negotiation with Goto to buy back AuctionRover 11:18 – Scot bought back AuctionRover for around $1M 11:37 – They bought it back in 2001 12:00 – When Scot IPOd ChannelAdvisor, everything was new to him and he had never taken a company that big before 12:07 – Scot’s dad was a business person and was on Fortune Magazine 12:58 – Scot always has a higher goal 13:37 – “If you’ve raised a venture capital, you’re going to have an exit” 13:47 – Scot wanted to see what an IPO process looked like 14:02 – Scot raised capital for ChannelAdvisor 14:14 – ChannelAdvisor helps retailers and brands sell on eBay, Amazon and other channels 14:26 – ChannelAdvisor raised a total of $90M before the IPO 15:08 – ChannelAdvisor’s market price on Day 1 16:03 – Scot brought in a COO to help him 16:11 – After going public, the COO was promoted to president 16:20 – Scot felt he wasn’t learning much more and the president wanted to step into the CEO role 16:27 – Scot felt it was a great time for the president to mature and take on the CEO position 16:47 – Scot just simply sent a letter to the board about him leaving 17:35 – Scot is more of a tactical entrepreneur 17:47 – “I just really like solving hard problems and scaling businesses” 17:55 – Everytime Scot would have a career change, it was in a different space 18:05 – Since Spiffy is consumer oriented, Scot believes he can scale it faster than ChannelAdvisor 18:27 – Scot’s goal for Spiffy 19:35 – Scot had 2 physical car washes after selling his 2nd company 19:44 – Spiffy was an MVP in 2014 when it was launched 20:09 – There are reasons why customers don’t like detailing 20:40 – 70% of Spiffy’s revenue is from out-work consumers 21:11 – Spiffy just crossed the $200M runaway and is growing annually north of 100% 21:33 – Team size in the office is around 20 and around 60 technicians 22:06 – Spiffy has raised $7.5M on their series A 22:18 – Scot still gets excited raising funds 22:38 – Scot’s aspiration for Spiffy is bigger than his checkbook 23:55 – The Famous Five   3 Key Points: Always aim higher when it comes to your goals. Going through multiple exits boosts your learning and experience. Always trust your instincts.   Resources Mentioned: The Top Inbox  – The site Nathan uses to schedule emails to be sent later, set reminders in inbox, track opens, and follow-up with email sequences Klipfolio – Track your business performance across all departments for FREE Hotjar – Nathan uses Hotjar to track what you’re doing on this site. He gets a video of each user visit like where they clicked and scrolled to make the site a better experience Acuity Scheduling – Nathan uses Acuity to schedule his podcast interviews and appointments Host Gator – The site Nathan uses to buy his domain names and hosting for the cheapest price possible Audible – Nathan uses Audible when he’s driving from Austin to San Antonio (1.5-hour drive) to listen to audio books Show Notes provided by Mallard Creatives