Editor’s note: WRALTechWire publishes today the second in a new series: In-depth interviews with Triangle entrepreneurs, each of which will include multiple parts. Our second package focuses on Eric Boggs, founder and former CEO of Argyle Social who recently launched RevBoss. WRALTechWire Insider columnist and entrepreneur Joe Procopio will be having candid conversations over a beer with our profile subjects throughout 2014. Also included with each package will be a Q&A that goes beyond standard business and video interviews with WRALTechWire Editor Rick Smith.The Q&A and video interviews will be published later today.

DURHAM, N.C. –  Here’s the concept. I sit down with a startup founder and we drink one beer. During that beer, we have a normal non-journalism, non-marketing, authentic conversation. That’s all it is. When the beer is gone, we’re done.

  • Site: Mez, Durham NC
  • Boggs ordered: Green Flash West Coast IPA.
  • Procopio ordered: The same.

Joe Procopio: Sorry I’m late. Today’s been one heck of a day..

Eric Boggs: (laughs) Why was today so hard?

Procopio: Well, first of all, you’re not supposed to be asking the questions, but thank you. No one ever asks me questions. Today was just one of those days where nothing went right. We had a miserable roll to production at 5:30 in the morning on the worst possible day to have a bad roll. We got it cleaned up and it was fine, but it was not fun.

But also, I’m in this place where I’ve got a dozen things I’m supposed to be working on and I can’t figure out how to get past any of them. It’s like “Get me someone, and get me someone while I’m waiting!”

Boggs: Classic Christmas Vacation reference, by the way.

Procopio: You caught me. I just watched that with the kids. I know Thomas is still real young, but the day you can watch that movie with your kids will be an awesome day. That and, oddly enough, the Three Stooges. My daughters gave it a blank stare but my six-year-old son was rolling and crying he was laughing so hard.

Boggs: For me it was the Little Rascals. Visceral, stupid, and hilarious. Thomas is still way too young for the Stooges or the Rascals. He repeats everything now. Kelly and I are at the point where we really have to watch what we say.

Procopio: Anyway, enough about me. So. I’ve never asked you about your departure from Argyle Social.

Boggs: Yeah.

Procopio: I’ve always kind of treated that as none of my business.

Boggs: I can’t share too much, in part because I’m still a significant shareholder in the company. I will say it was a weird feeling waking up the day after I was no longer CEO and not having to do anything Argyle-related. You get whiplash. It’s like you’re running 150 miles an hour towards a goal and suddenly you stop. It was an odd feeling for a while.

That said — I will freely admit that it was oddly liberating to no longer worry about the intractable problems that start-up CEOs have to solve every single day.

Procopio: Part of why I never asked was that the way you went out was class. You sent an email around that kind of answered all the questions without getting too deeply into it. And I’m not saying you have to broadcast something like that, but still, there’s that, “Hey, my email address isn’t going to work anymore.”

Boggs: So I sent one email to my professional friends, most of whom are in the start-up game, and another to my friends and family that are decidedly not in the game. The one you got was the professional network — I didn’t have to explain, it was just like, “Hey, I don’t work here anymore. Love the team, wish them the best, still invested in their success.” The email I sent to my parents or the friends who have no idea what I do, that was more complex, it took a lot longer to explain.

It was funny — the responses that I got. I wrote a post about it online. A lot of my local friends were flummoxed.

Procopio: Well, you were the face of the company.

Boggs: As the CEO that’s the job you have to do.

Procopio: But it was more than that. You wore the pants, those… beautiful argyle pants.

Boggs: I still have them — several of them in fact. I actually got the for free from a golf apparel company. I was effectively a sponsored athlete — more or less just like Tiger Woods.

Procopio: Ha! So you were pretty much Eric Argyle to a lot of people. It wasn’t just a CEO thing – you were synonymous with the company – at least here. So it was shocking.

Boggs: Yeah, externally shocking. The funny thing is that the response locally was “Oh my God! How will you go on?” whereas my friends who work in California were like “Oh, OK. Great. What’s next?” It was mind-boggling the difference between local and California. Then the third group of friends of family really didn’t get it.

Procopio: So you’re kind of hinting at this, or maybe you’re not, this failure thing that we still don’t deal with well here.

Boggs: Yeah. No one talks about it. EvoApp got the spotlight shined on them a little bit — maybe warranted, maybe not. But there are plenty of other companies in town where things didn’t go so well and things aren’t going so well. It would be a big deal if it weren’t the norm for things to actually not go well for the overwhelming majority of start-ups. You just have to experience it to understand it.

Procopio: So the times I failed happened to be the times here when no one really gave a **** about startups. What do we have to do differently here to lose that stigma of failure? I still feel it today, sort of an overarching fear.

Boggs: To a large extent, failure can drive you. If you don’t let it cripple you, it can spark a lot of positive behaviors. You eventually get to a point in your career when you know who you are and you know what you’re good at and what you’re capable of doing. Then you just kind of play the game the best you can, with the understanding that ultimately the market and luck will decide your fate — they can be an overpowering, soul-crushing force or they can make the sun shine awfully bright.

Plus — I don’t fear failure at all really…because well, I know I can just get a job.

Procopio: Right. But it isn’t even that.

Boggs: What’s the worst-case scenario of failure? You could lose your house I guess…

Procopio: Yeah, but the… scarlet letter of failure, which you have to do. You have to fail in this profession.

Boggs: Yeah but like nine out of 10 people who start companies fail. It’s hard not to take it personally but you can’t. Like many things — I like to use a basketball analogy. I’m a Tarheel — I’ve worshipped them my whole life and retain the expected deeply-seated hatred of Duke basketball…including JJ Reddick. But I gotta admit that I’ve kind of always secretly admired JJ Reddick because he’s fearless. He can go oh-for-eight and still keep chucking up shots until he hits them.

You have to be that way. And its funny because I played basketball the same way from 6 years old through high school, taking shots because I knew I could hit them. My high school coach would jump on my case fairly often and, with youthful ego, I guess, I’d say, “Look. If that shot had gone in, we wouldn’t be having this conversation.” (Laughs)

But getting back to failure…I never thought about that – the people whose opinions matter, they get it. Anyone who would disparage failure, their opinion doesn’t really matter anyway.

Failure is a cloud that hangs over every company, even big companies. It’s a race against the clock and a race against the market, sometimes it’s a race against physics that you just can’t control.

Procopio: So good segue. Let’s talk about RevBoss.

Boggs: What do you think of the name?

Procopio: (pause) I don’t know. Tell my why you chose it.

Boggs: I’ve only worked for two companies, Bronto and Argyle, both of which have tangible brands and logos. I wanted a short name, and I landed on RevBoss…but I’m not sure what the logo might look like just yet.

Procopio: But you’re going service this time.

Boggs: Yeah, well, Argyle was actually services company for the first eight months. I did email marketing consulting for Duke, Lulu, an online tools-and-hardware company, a lingerie company, plus a few more odds and ends. And that work bought me enough time to crystallize the Argyle concept and sell Adam (Covati) on getting involved.

RevBoss is much different as it’ll be a services company for a good long while. We’ve had meaningful clients from the outset — I’m billing 50-60 hours a week and actually turning away work. I attribute RevBoss’ early to success to me being a former-slash-failed-I-guess CEO, you learn to do things and see things in a way that are enormously valuable to companies.

Procopio: So that’s where I came to Automated Insights from. I had founded a product/services hybrid company that I built to $1 million in annual revenue. Then Ai came along. Maybe I’ll do a services company next, but probably not.

Boggs: It’s cyclical. One of my friends runs a studio and he’s killing it and he’s transitioning into a startup CEO as I’m transitioning into services president. And it will probably flip back three to four years down the road. If you hustle, services companies can create significant revenue to do what you want to do. And plenty of amazing products spin out of services companies, MailChimp being a great example. Services to product is a natural ebb and flow for an entrepreneur.

How long did it take you to get to a million in revenue?

Procopio: Ah… from the time I hired my first person… two-and-a-half years.

Boggs: I hope that my path with RevBoss is similar to yours. If I can build RevBoss into a consulting company that has a small team of highly talented, well-compensated people that create amazing results for our clients, then I would be incredibly happy with that. For now, my focus is on building a business, not a venture. 2013 has been very, very good, and my goals for 2014 are significant. RevBoss might turn into a product company down the road, but I’ll spend the next 18-24 months moving heaven and Earth to help our clients find scalable ways to grow their companies.

Editor’s note: Joe Procopio is a serial entrepreneur, writer, and speaker. He is VP of Product at Automated Insights and the founder of startup network and news resource ExitEvent. Follow him at Twiitter or read him at his website.