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 stifling the growth of their businesses. They don’t know when to quit and let others push the company forward. This summer is when it really hit me that I was reaching that point. After having put together a lengthy and clear plan to present to the management team in summer of 2024 about a path forward, this year I was at a loss. I knew the team was right about where the company needed to go, but I didn’t have that vision on how to take it there. So, I began to make plans.
Fortunately, I didn’t have to look too hard to find our new fearless leader. David Hotz is someone I’ve known his entire life. More importantly, he has been with Cranky Concierge for more than a decade. He started off helping look for award travel options for clients, but most recently he’s been our VP of Operations. And now, on January 1, he will step into the role of President. Here we are celebrating his sister’s wedding a few years ago.
With that, my 16-year run in active management will come to an end. I will continue to own the business, so it’s not like I am completely severing ties. But I won’t have anything to do with the day-to-day operation. As mentioned, I had long ago stepped back from much of the fun work on the front line anyway, but now I’m ready to let Hotz and his team take the lead on the future. I am not worried.
To be clear, the core service isn’t going anywhere. We are still here to help air travelers when plans go sideways and to make sure someone is watching out for them when no one else is. But Hotz has long pushed for more than that, and he’s the one who led the evolution of our services into a full-service travel planning operation. We still help clients keep their air travel on track as much as possible, but we also work closely with top hotels and partners around the world to create experiences that travelers often cannot access on their own. We even design full custom itineraries from start to finish and make sure as many details are covered as they desire. Hotz has been the driving force behind that expansion, and I am excited to see where he takes it next.
As for me, well, I will be focusing on everything else Cranky that I do already. That means more time building up Cranky Network Weekly and the Cranky Network Awards. I will also be thinking about Cranky Flier itself to figure out what I should be doing differently, if anything. And of course, there’s The Air Show podcast. These are the things I just haven’t been able to focus on with any great effort because of the amount of my time that Cranky Concierge has occupied. I’m looking forward to this.
If you’re looking to travel and want that extra helping hand that only real, live humans can provide, Cranky Concierge will remain the best place for you to go. Actually, it’ll be even better as Hotz and the team keep expanding into other parts of the business, getting more benefits, creating more relationships, and improving travel for even more people. I can’t thank them enough for what they’re about to do, but also for making it as easy as possible for me to leave knowing the business is in good hands.
