A New Leader Takes Over Cranky Concierge at the End of the Year

It’s been more than 16 years since I started Cranky Concierge to help travelers with air travel problems, and things have changed a lot since those early days. Now, the biggest change yet is coming... I’m stepping down as president at the end of this year. When I first started the business, I relied on readers here to help me test out the idea that people would pay for someone to monitor flights that were booked elsewhere and help if things went wrong. It didn’t take long to prove that model worked - the very first person I monitored had an American delay that wreaked havoc on their plans (some things never change). In the early days, it was just me monitoring flights 24 hours a day. But soon we had Patrick and Andrew as the first concierges to help me. And then we grew into actually booking the flights ourselves as a travel agency. We had some great highs, including the eruption of Eyjafjallajökull in Iceland where we worked some near-miracles to get people where they needed to go. We also had some devastating lows, none lower than the COVID pandemic where bookings disappeared overnight and we struggled to stay afloat. But we did survive, and soon enough we were growing again. During those 16 years, we’ve had 87 different people work for Cranky Concierge by my count. When I pulled the numbers recently, we had more than 68,000 one-way trips where we sent Cranky Updates to clients. Those numbers are staggering, but it’s the fact that I remember so many of them from so long ago that really hits me. When we got someone to a dance competition just in time or to a cruise or to a wedding, the travelers were thrilled... but we were just as excited. It was like a personal victory every time we solved a problem, and that was beyond gratifying. Over the last few years, a few things have become apparent to me. As we’ve grown, I’ve gotten away from doing the fun work of actually helping people. I have instead been mired in things like my personal nemesis: finding health insurance for our people. But I was also looking at things on a strategic level, and it quickly became apparent to me that I needed to think about moving on. My team had long been beating the drum that our focus on air travel wasn’t enough. We had relationships that could provide remarkable benefits to travelers well beyond just flights. Further, diversifying the business could help protect us against airlines that unilaterally decide to quickly and arbitrarily change their models to penalize agencies. (Yes, you, American, even if you reversed course, and United is doing its own work in that area.) The direction became clear to me, but the problem is... that’s not really my thing. And that brought me to consider what I’ve always wanted to avoid. I find that founders can stay on for too long and end up...

Preview: ~500 words