Inside Schedulefly: To fly or not to fly?

Yesterday I spoke to a long-time customer who is an absolutely awesome guy. He has been watching us for a few years to see if our business does well. Four years ago he probably figured that we had little chance to succeed. I wouldn’t have blamed him. After all, it’s not exactly a likely scenario that three guys in their 30’s with families and kids could make ends meet selling individual subscriptions for $30 or $40 or $50 per month, unless they have VC or angel funding. We have neither. But we’re fortunate enough that the stars aligned and we’ve been able to make this business thrive.

Anyway, our customer is pretty plugged into the restaurant industry, and he wants to help me get on the speaker’s circuit for state and national trade show events. It’s a GREAT opportunity, and I thanked him for offering to help! I also told him about a couple of concerns I have, one of them being that I would have to travel to be a speaker.

Eight years ago, I would have laughed at myself for being hesitant to travel. I used to fly all over the country in my previous career, and didn’t think anything of it. Three, four trips per month. No sweat. I pretty much had to travel to succeed at what I did. And the the time I had no kids, so why not see cool cities all over the country.

Well, now I have three kids and I don’t like spending day away from them and my wife, and I’m fortunate to be a part of a business that isn’t backed by guys and gals that have given us lots of money and have lots of expectations about how how quickly we should grow. If we were, my hesitation would be irrelevant. I’d have no choice but to jump at the opportunity to travel around and speak at these shows. The pressure would be high to travel, sell, speak, and work 100 hours per week if needed to meet lofty growth goals.

But we’re not funded or backed or anything like that, so that leaves me with the (very fortunate) dilemma of being on the fence on this topic. Would it help our business? Yeah, it most likely would. Would it be taxing on me? Being that I pretty much can’t stand airports and airplanes anymore, and that I absolutely don’t like being away from my family…yeah, it would.

I’ll probably wind up taking the opportunity if it pans out (which is no guarantee), but it was weird hearing myself tell our customer that I had to think about whether I even wanted him to pursue this. It’s funny how things change as you grow. You place value on different things, your perspective changes, and you view the world through different eyes than you did not that long ago.

I’m not sure what the point of this post is, other than to share a little glimpse behind the scenes at Schedulefly and offer a brain dump of what’s on my mind right now. I’ll let you know what happens…