Scot Wingo is co-founder and CEO of ChannelAdvisor, a public company in Morrisville, N.C. that helps e-commerce retailers optimize sales across channels. Wingo and team took the company public in May 2013, providing an important success story to the Triangle startup community.

Flash back to 1995-I was 27 and the CEO of my own company, living the entrepreneurial dream. After getting an undergrad degree (University of South Carolina) and a master’s (North Carolina State University) in Computer Engineering, I went to work for a software startup in Connecticut. While I loved the startup lifestyle, I wanted to a) move back to the Triangle and b) take a shot at starting my own company with a couple of friends. We called it Stingray Software.

About six months into it, we were doing great-we had hundreds of customers, revenue was flowing in and we were profitable very quickly. On the surface, everything looked great, but I was somewhat freaking out. The challenge was that we quickly grew from three founders to ~15 employees. The sales people were in-fighting. Their comp plans were not well thought out. Some employees wanted to know about their ownership/stock options while others wanted to know about our inclement weather policy.

As an engineer by trade, these topics were way out of my league. Why couldn’t we just create a great product and sell it?! Did we really need all these team members?

Help! I picked up the phone and called my entrepreneurial professor from NCSU, Dr. Tom Miller, and asked what I should do. He suggested I call a serial entrepreneur, Richard Holcomb, and see if he had any advice. Richard had sold a company called Q+E Software and had started his second company HAHT Commerce.

I remember it like it was yesterday, Richard said he could come by for an hour and he stayed for three. He attacked the white board like a wild man-drawing sales comp plans, talking about the pros/cons of different option plans, the importance of employee agreements (What? We need those?) and how to use a system called a CRM to tie it all together. It was so valuable, I asked Richard if there was some way we could/should pay him-his answer was, “Nope. Someday when you are successful just help the next guy.” 

Richard introduced me to a lawyer, Walter Daniels, who did a ton of initial work for us around all of the documents we needed and charged us what I knew was substantially below his normal rate. I thanked him profusely and he said, “Scot, someday you will be successful and what we need in this area is more folks like Richard that help other entrepreneurs to be successful. I just want you to remember this and make sure you give back to this community.”

Fast forward-we sold Stingray to a public company in 1998, started our second company, AuctionRover in 1999, sold that in 2000 to a public company and then spun out a company called ChannelAdvisor in 2001. Over the next 13 years we raised ~$90m in venture capital and went public in 2013 under the symbol ECOM.

Over that three-company, ~20-year career, I’ve seen a little bit of everything. Most importantly, I’ve made every mistake in the book.

I’m a huge fan of ExitEvent and have really enjoyed what Joe and Laura have been doing lately. I met Laura recently and was sharing how great it is that we have a TechCrunch-like resource here in the Triangle area now. She mentioned that they are always looking for new content.

Over the years, I’ve tried to do as much as possible to give back to the community by speaking at CED events, coaching startups, serving on boards and participating in local investment groups. But one thing I haven’t done is write about entrepreneurship, because there hasn’t really been a vehicle for something like that. I do a lot of blogging with ChannelAdvisor, but that is really ChannelAdvisor-oriented and thus tends to be really focused on e-commerce and what trends we are seeing there vs. broader entrepreneurship.

Putting together our area’s awesome culture of selflessly giving back with the awesome new ‘channel’ provided by ExitEvent, I thought it would be fun to tie those together and do a Q+A type column here on a regular basis. My marketing playbook has three words: Keep It Simple, so I pondered it for hours and came up with: “Ask Scot”.

How do I raise a seed round?
What’s the best way to pitch?
What are pitfalls in term sheets from VCs?
How do I find a founder?
How should I think about stock options?
How should I price my product?
Does your name really have only one T? Why?

All of this is fair game. All I ask is that you provide a bit of context by answering these questions:

Name and contact info
How big is your company? (number of employees)
What stage are you in? (idea only, prototype, < $1m, $1-5m, $5m+)
What industry are you in? (consumer oriented, healthcare, finance, don’t know)
Are you ok with me sharing the above as part of the answer or would you prefer to stay anonymous?

Part of my philosophy on blogging is to not reinvent the wheel. So as I answer your questions, I probably will frequently link off to great reference content from folks like Fred Wilson, Brad Feld, Marc Andreessen, etc. But I’ll always put a personal/Triangle spin on it.

Finally, what I think we’ll find as we go on this journey together is there are no black/white answers, but lots of shades of grey. I’ll try and help you think about that by sharing pros/cons and what I know has worked/not worked. And hopefully that helps you settle on the shade of grey that is right for you.

To kick it off, there are a couple of ways to ask questions:

*You can throw them right in the comments for this or any post. That will obviously be public.

*If you prefer email or to be anonymous, you can email them to [email protected]

I’m really looking forward to hearing what’s on your minds out there in Triangle startup-land and helping as best I can.

Follow Scot on Twitter @scotwingo or LinkedIn.