By the time former Argyle Social founder Eric Boggs and I got halfway through our first beer last night, we realized we were on somewhat divergent paths, and probably had a lot of advice for each other.

One thing was for sure, this whole entrepreneurial thing can get pretty cyclical.

Boggs is launching RevBoss this week, a services consultancy with a core deliverable of helping companies navigate and perfect the process of moving from site visitors to repeat customers. RevBoss is the focus he’s settled on roughly one year removed from being the founder and CEO of Durham startup Argyle Social, a product company with which he still has significant ties.

On the other hand, I’m now in year four at Automated Insights, who initially was a client of a product/services consultancy I built and had grown to $1 million in annual revenue before putting it on hold to make machines write professional-sounding personalized narratives out of data.

One more thing we figured out. The second startup (or in my case, the 10th), is exponentially easier than the first (or even the ninth). Counting Bronto and Argyle, this is Boggs’ third.

And a final similarity. Boggs and his wife Kelly had their first child during the growth phase of Argyle, and had another on the way during his tenure there. When I officially started my consultancy, I had 18-month-old twin daughters and a son on the way.

Having a family, we agreed, makes you a different kind of entrepreneur. Not in a risk-averse way, but it keeps you from making stupid mistakes and it also forces you to prioritize what you’re working on. In any case, we both feel like we’ve got better at startup after having kids.

Who knew?

This time around, Boggs isn’t building a venture, he’s building a business. It may become a venture over time, which is exactly what happened with Argyle, but for now, if he can build it up to a dozen people with a seven-figure recurring revenue pipeline, he’d be incredibly happy with that.

And like all good entrepreneurs, he’s leaning on what he’s learned over the last ten years bringing customers into Bronto (where he was the first hire and built out the initial sales team), to Argyle, to the dozen or so clients he currently has on board at RevBoss, including Ignite Social Media, UserVoice, and Adzerk.

“It’s really, really hard to get a customer,” he answered when I asked him what was core to RevBoss. ” We want to work with SaaS companies and eCommerce companies to get customers and revenue through online marketing.”

He’s definitely onto something. With the dearth of financing here in the Triangle (although, it’s not limited to the Triangle, this could essentially work anywhere), customers and revenue are not only of the utmost importance, they’re critical to survival.

“Only a handful of startups here have gotten beyond the first 10 customers,” he said. “Not being able to get to 10? You can attribute that to a number of things — founder incompetency, product-market fit. But getting to customer 100 and 1000, those are very different problems to solve. And I’ve done it twice.”

The goal is not for RevBoss to be an irreplaceable resource, rather, Boggs wants to build capacity internally so companies can insource their sales. For example, with Adzerk, Boggs developed a prospecting program that their sales team now runs on their own.

He’s had a solid 2013 on his own, and his goals for 2014 with RevBoss are significantly higher.

“Half of my SaaS clients have technical CEOs,” Boggs said. “They write code, think like a developer, they’re charismatic, empathetic, but they’re not sales guys. RevBoss has found a real niche isn helping fill those gaps.”