The Grass Isn't Always Greener on the Entrepreneurial Side

Cables to Clouds. Published 13 June 2025. Hosts: Tim McConnaughy and Chris Miles.

Tim and Chris had recently talked with Scott Robohn about leaving a corporate job to start his own thing. They wanted the other side of the coin: someone who had done that for eight years and then gone back. That is me. We spent the first stretch on the USNUA, which Tim has been to in Raleigh, and the rest on what running a company is really like.

How the USNUA happened

It started as the Ohio Networking User Group. There were VMUGs and Linux groups and vendor user groups, but nothing general for network engineers, so a few of us in Cleveland started meeting, then Columbus, Cincinnati and Toledo. COVID pushed us onto Zoom and gave us time to think, and we used it to build an enablement package so people in Indiana and Michigan who kept asking "how do I do this" could run their own. Now there are 30-some chapters. The format: a local organizer, ideally an account executive paired with a sales engineer because one knows the content and the other knows how to throw a party; a non-selling presentation on an open technology; a panel; and a moment at the start where we ask who is hiring. Beer matters. The team handles the logistics so the organizers do not have to.

Starting WAN Dynamics

I had spent thirteen years at a Cleveland service provider when it was acquired, and I gave the new owners an honest six months. Meanwhile I had just turned 40 and kept telling a friend about this SD-WAN thing. I had plugged two circuits into a VeloCloud box, yanked the primary and dropped one ping. He said, why don't we just start a company to deploy and manage that? He had hired me for my first dial-up support job in 1999, and this would be the fourth time we worked together. We incorporated four months before I quit and landed a retailer as a consulting customer first, because I was not jumping with zero revenue.

The first two years were rough. I made half of what I had made before. Cash flow is the thing nobody warns you about; the bigger the customer, the longer they take to pay, and 60 to 90 days on a 30-day invoice is normal. I lost sleep over hiring the first employee, someone I had talked out of another offer. Then SD-WAN went mainstream around 2017 and 2018, Ohio's conservative buyers came around, and we grew. COVID was explosive for us: three to five maintenance windows a week getting people onto remote access, and we gave the whole team a raise to stick it out.

Why I left

The managed SD-WAN market saturated. Carriers bundled it with circuits and voice as a loss leader, and an over-the-top provider cannot match that. My partner and I started to disagree on how to grow. And the sales job kept landing on me. We were excellent at engineering and operations and terrible at telling the world about ourselves, and every attempt to hire that away came back to my desk. Being seven feet tall does not mean you want to play basketball. We gave it an 18-month plan with a new sales leader, it did not work, and as 50/50 partners we took the company to market and sold it. He went to run the USNUA full-time. I went with the acquirer, inherited three jobs, flew 40 legs in a year and burned out completely.

Why I took a job

I took four months off, the first two doing nothing at all. I already had Bits in Flight as an LLC and seriously considered building it out. But I remembered the ramp, the chasing invoices, and this time without a partner to take the back office. And health insurance without an employer is very expensive. So I joined Laketec as CTO, a 36-year-old company I had admired since almost taking a job there in 2008. The adjustments were real: back in an office, which we negotiated down to three days; not having the final say when I have a strong opinion; and none of the institutional knowledge. The relief is also real. My day can end at five, the hardest calls about people do not roll up to me, and I get to do the CTO job I never actually got to do as an owner.

Two things I would tell anyone considering the leap. The pressure to keep growing is partly societal, and I regret not being more at peace with a flat year, because flat with recurring revenue is fine. And "your own boss" is a myth: your employees, your customers and your vendors are your boss, all at once. It has real rewards. It also requires thick skin, because some seasons just suck and you get through them.

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