Part of the reason Jay Garmon chose Louisville. From left to right, wife Jenni, daughter Quinn, Jay and daughter Rylie.

Jay Garmon is about as close as Louisville has to a start-up nomad.

That specie of homo technicus so common in San Francisco and Silicon Valley is vital to creating, then sustaining, any city’s entrepreneurial culture.

The swashbuckler who jumps from big corporation to start-up, start-up to big corporation.

At the Louisville level, it’s extremely rare because there aren’t that many viable startup-to-corporate-to-startup opportunities.

Though there are notable exceptions.

For example, last week, Jason Falls – who gave up a gig at Doe Anderson back in 2007 to found Social Media Explorer – departed SME after five years to become vice president of Digital Strategy at CafePress.

Jay just turned down a staff position with Backupify after working remotely here as director of content marketing for the Boston-based cloud storage company, which started in Louisville.

Before that, he worked at VuPal, Game Jabs, TechRepublic/CBS Interactive/CNet and TechTarget.

Jay has been at the center of Louisville’s entrepreneurial community for more than a decade, and was co-founder of the Louisville Digital Association with Jason Falls.

We thought this would be apt juncture to get Jay’s view of why he would, in essence, bet on Louisville over Boston. Also, we wanted his insights into the symbiotic relationship between startups and large corporations, which often compete for the same people in a talent pool that’s small compared to East and West Coast innovation centers.

Insider Louisville: You could have gone to Boston to work with Rob May at Backupify, but you’re not. You moved from startups to established companies and back again. Seems like a logical move.

Jay Garmon: I’ve had plenty of opportunities to relocate in the past. San Jose, California. Boston. I won’t do it. That confuses a lot of people.

Why wouldn’t you jump on those opportunities?

There are a whole lot of reasons. But at the end of the day, I want my children to know their grandparents. All of my family is here. The other part of it is, I’ve been around he block and know enough people to realize that 95 percent of the people who live here end up back here. Because it’s never greener on the other side. The story I always tell is, I got laid off from CNet in 2008. The VP who had unenviable task of laying a bunch of us off … not for cause. CNet got sold to CBS, and the condition of sale was, 10 percent of the workforce goes away. Whether they’re doing a good job or not, just get rid of them.

He all but said in my exit interview, “I’ll be calling to hire you back in less than six months.” Which is exactly what happened. The issue was, in order for him to hire me back, I had to move to San Jose. What I said to (him), “You’re senior vice president. Been with the company forever. I know you make serious money. Yet every meeting we had started with, ‘Thank you for riding with CalTrans’ in the background.’ Because you’re on the train for an hour, going to the office. And you live with your in-laws. You make good money. You have a beautiful wife. Wonderful kids. And YOU can’t live like I live! Other than the opportunity to do this kind of work, what are you offering me? On a horrible day, I have a 15-minute commute. And you can’t tell me you have better restaurants. Unless I really want to go to a town with pro sports, what are you offering me? The money is a wash. The money you’re paying me I’m losing in never owning a house.

 So, what are you going to do now?

I’m separating from Backupify, amicably. They’ve offered to reduce me to part-time. Two things happened. One, I wasn’t willing to move to Cambridge (Massachusetts) Two, because I’m not willing to move to Cambridge and be the guy in the office who solves random problems … getting on the white board and white-boarding things … doing jam session meetings and being a strategic employee. They don’t need a full-time writer, the other thing I was doing for them. That just wasn’t working for the new SVP. At the end of the day, it’s his department to run. I’m still friends with the CEO (Rob May) and the VP of product and security. We’re at the point now where you’re all in, or you’re not.

 Did Rob say, “Gosh, Jay, what the hell are you thinkin’? “

No, Rob gets it. He totally understood. And he said, “My next start up, I’ll be calling you.” In three years, when he’s out of there, they’ll bring in a next-level president or they get acquired by somebody else. … he’s never going to stop doing what he’s doing. He’s going to call me. He’s going to call Ben Thomas, who’s the VP of product over at Backupify. There’s a point in a startup’s life cycle where it gets real. You have to be in the meetings and at the white board. That’s really, really hard to do on a Google hangout. I’ll totally concede that.

 Do you think this is what (tech people) get used to? The start-up thing is adrenaline-versus-stability, right?

It is. Those of us who’ve been laid off from corporate jobs … this notion being in a corporate job makes you safe. There’s a greater illusion of security there. I’d been at CNet seven years and seven days when I got the ax. They flat out told me in the exit (interview), “You didn’t do anything wrong. We just have to cut a number, and you’re in the number we’re going to cut.”

To me, this is almost a Louisville economic-development issue. It’s good and it’s bad. You’re still here and you’ll probably do something with someone’s startup.

If I can.

And then you’ll get picked up permanently by someone in a bigger deal. But you can’t see it yet.

That is the one difference. If I’d been in Cambridge, and I’d been there long enough to have a network, I would have just rolled into someone’s starup. There’s a lifestyle like that. There are people who are never founders – I may be a founder someday – who just are “Employee 10” at seven consecutive startups. That’s just their gig. They like the lifestyle. They like the energy. They like working at that kind of company. There aren’t enough startups on the ground to live like that here. Humana has called me, or at least recruiters on behalf Humana. I’m not afraid to say that. Humana is hiring like crazy, all kinds of talent. But the issue is, do I go to Humana for two years, and I’m out of the game for two years? Then, I’m in a position of, “Do I leave a good job at Humana to talk a risk on a startup? You get used to those golden handcuffs, I’m the kinds of guy who, having lived on both sides, could make the jump easily. Shawn Morton great example, who moved back to town. Shawn tried to start up Prophylactic, a FriendFeed competitor that lost to FriendFeed for various reasons but was a very good product. He had to go get a real job and had to move to Columbus, Ohio. Got a good job at Nationwide. Has a great job at J.P. Morgan Chase. But’s really hard for him with six kids to jump back into the startup game . Which is a shame because in his blood, Shawn is a startup kind of guy! Who really gets it. And whoever reads this, talk to Shawn if you’re looking for a really great user interface guy! He’s a genius at it!

Okay, (venture capitalist) Bob Saunders calls and Humana calls, which call do you take first?

Bob Saunders.


Oh, yeah. Humana is always going to be there. That’s the nice thing bout the golden handcuffs. Humana’s always going to be there. It’s not going any where. Really, that’s the big contribution they make to the start-up scene beside drawing great talent to town … If there’s not another startup to jump to, you jump to those.

Let’s talk about what no one is going to tell the young startup guys. You’re saying, “You can leave a corporate job to join a startup, then come back if things don’t work out.” You’re saying, “You can do that if you don’t stomp out in a snit.”

As long as you don’t burn the bridge when you walk out the door, I think you’re fine. More importantly, smart corporations … love the idea of bringing in knowledge from outside their organization. As a matter of fact, the easiest way to get promoted in this town is to change companies. There are plenty of guys who can’t move above a certain level at Yum! or at Papa John’s or Brown-Forman, but if they went from Brown-Forman to Papa John’s they would go up a level. If for no other reason than Papa John’s wants to know what Yum! knows. Brown-Forman wants to know how Ford does supply chain. That’s healthy for them. I’ve had three conversations with some of the recruiters.

Recruiters are important to allowing startup people to move back into big corporations ….

I was at CNet for seven years. I’ve been at Tech Target. I’ve been at three startups. I’ve talked to a lot of people. I’ve done a lot of things. When they see that, my detriment to working at corporate is I don’t have a plug and play resume. “I’m looking for five-to-seven years in search engine marketing with this specific kind of software.” So I have a barrier to entry in getting past their automated resume system. But if I go to a recruiting firm, they say, ‘Oh, you’ve done these five things. When I go to call the head of HR, I get it.”

You’re talking about the difference between the aggregate knowledge you’ve collected for 10 years versus finding a round peg for a round hole. You’re saying, get the right recruiter.

Yes. Don’t worry about having a plug and play resume. That’s how it works in Cambridge. All these guys who move between startups. They never directly interview. There are eight or 10 startup talent brokers who know who’s moving, they know which startups are doing well. They know who’s not happy where. They know the director of marketing who wants to be VP of marketing next time around. They know the VP who wants to be COO the next time around. But nobody has the perfect resume. I get tired of hearing about this skills gap in this country. There isn’t a skills gap. There’s an “exactly perfect fit for exactly what you want” gap. If you’re willing to spend 90 days on-boarding somebody, you can have the perfect employee in 90 days. What you can’t have is the perfect employee in seven days. There’s no skills gap. There’s an “oh my god, I can’t use an automated resume to get 100 people to apply for this job” gap.

What we’re really talking about is changes in corpoate dynamics.

Especially at the top. I’m lucky because I’m a dozen years into my career. I’m in my mid-30s. (Companies) are willing to take a flyer on a guy in his mid-30s who’s done a lot. They’re not willing to take a flyer on a dude in his mid-20s who’s done a lot. I will totally concede that. The guy coming out of Speed School. Two years of coop. Thinking about getting his masters in electrical engineering. If he’s a coder, he’s going to get certain coding jobs, but no one is going to walk in and make him a department manager. That’s why startups are such a great deal for those guys because they can get legitimate management experience from day one. Especially if they start their own company. Alex Frommeyer (CEO of Beam Technologies), whatever happens with Beam … because he started his own company, he’ll never be anything less than a department director for the rest of this life. Same thing with Adam Fish and Chris Vermilion at Roobiq.

That’s my best argument for getting in the startup game.