manager blog barry and steve skyrun biz rentals

1.30.2018 - Ownership Matters: Skippy Mesirow GM

I sit back, move my foot to the left, put an earbud in and shut my eyes. It's 12:45 pm on a Sunday. Tomorrow's a workday, and I'm going to Japan. Not for work, golly no, to ski, like… with friends and stuff. And drink Whiskey. And yet, back home are five profitable properties, five happy homeowners, and currently seven guests. They are happy, and so am I. Comforted by a thriving business, elated at the opportunity to travel and expand my horizons, and gratified by the trust put in me to do both of these things simultaneously as I fly away over the Pacific.

How did this come to pass? One word, ownership.


A company's success or failure, measured in dollars or smiles or joy comes as the result often of the effectiveness of its leadership. Always the culture within the company reflects the ethos that that individual or those individuals bring to it. Never are leadership and the company completely at odds. And so, as I sit on this plane, club soda grasped in one hand, a smile creeping up my left cheek I have two men to thank. Steve Falk and Barry Cox.

Though new to SkyRun the presence of amazing leadership was quick to identify. In fact, it's one of the reasons I took the job. In light of this, I sat down with Steve over breakfast to learn more about his journey, what makes him tick, and how he thinks about the job of being numero uno (or numero .5 – Hi Barry… Sorry you missed a yummy breakfast!) at SkyRun, and where he sees himself and the company going next.

Growing up in a home with two professional parents, the dinner table was a place to hold familial court. This was a place of bonding and kindship but also a place to challenge, learn, and debate. Discussions were expected, and often lively. Challenging authority was not only allowed but encouraged, with no free passes. Backing up those challenges with hard evidence was critical to swaying the court. No matter how lively the discussion got, it always remained a safe place, just as quick to return to small talk and embraces as it was to escalate.

manager blog setting dinner table

Steve then, from a young age, had been trained to think like an entrepreneur. To challenge the status quo, to ask questions, to try new solutions to old problems. Critically too he was bitten by the entrepreneurial bug to do things his own way, to yearn for the day without a boss, and to make the world he wished to see.

After undergrad, Steve went on to law school, yet he always viewed it as his MBA, a way of understanding the world with a new lexicon to help navigate his entrepreneurial dreams.

Following law school Steve worked for a variety of tech start-ups, it was a boom time for internet companies, and Steve learned from each experience. Each success built the savings account; each failure built knowledge.

Upon meeting Barry Cox, SkyRun co-founder, and former IBM big cheese, the two struck up an instant friendship and an affinity for thinking big about business. Miffed at the service Barry had received from a company trying to rent out his apartment the duo hatched a plan to launch SkyRun.

This was visionary. Twelve years ago Air BnB was not even a thought bubble, and its founders were in high school. From the outset, the approach was simple and clear. Do service better. Give owners what they wanted. Invest heavily in marketing. Innovate.At the time, property managers felt they were doing the owner a favor. SkyRun would be different. Owners would be number one and make their experiences seamless. Caring was the top priority; this was their home for god's sake!

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Twelve years on SkyRun is in 25 communities with over 700 properties and growing daily. Why? Well, in a big part it comes down to Steve and Barry. At the start, they did it all. They mailed keys; they did inspections, they cleaned. Barry built the software and had the intuition and know-how from his days at IBM to think globally. SkyRun was the very first company to integrate with VRBO a full decade ago. Later it was the first and only property management company to have a proprietary integration with Air BnB. This is all Barry, in strategy and execution, and indeed set SkyRun apart. Steve was the sales guy. In their first season, he signed twelve properties, by the end of year one, an astounding fifty! This team was making a name for themselves fast.

But it was not all rainbows. As Steve said, they were leaning on the fly, drinking out of a fire hose, and in some instances failing to a solution, yet as Steve’s father would often say all those years back at the dinner table “perseverance wins over talent every time.” Eventually, their portfolio grew large enough where they could divide and conquer. Each founder would own a portion of the territories and self-manage; yet big decisions, like who to hire to launch a new location, remained a joint call. Critically they maintained a shared responsibility to one another and the product, sharing their unique skills, support, and tools with everyone in the SkyRun family, not just their own fiefdoms.

They had found the secret sauce, and it was all up from here. Barry and Steve's friendship became stronger than ever, and so did their business.As the years past and the business grew, Steve learned more and more. Some locations, like Keystone, worked right out of the gate. Others, like Vail, were more difficult. Steve has two simple rules that he lives by: 

#1 Find the right people. 

#2 Find the right people. Period.

In Vail, it took five GMs before he found one that made it work. Luckily, Steve remembered his dad’s advice once again, “perseverance wins over talent every time.”. Steve, undeterred, persevered. Now, Vail is thriving.

When asked if after all these years he has a sure-fire method for picking the right staff, he laughs. “No. You go with your intuition. Sometimes your right, sometimes you aren’t”. When I am hiring my first staff, he offers… “I guarantee you; you will be wrong… And you’ll be right”. He smiles, a glint in his eye. “You’ll crush it… and as long as you do, you can do whatever you want”. He gives me a wink and an excited wiggle that would make a Golden Retriever seem practically bashful and wishes me off to Japan, the day before a workday. And that interaction, perhaps more than Steve realizes, is the key to his, and SkyRun’s success.

Steve trusts implicitly, supports unconditionally, forms strong interpersonal bonds, wants the best for his employees, provides the tools necessary to succeed, is willing to try other options if things don't go well, and of course, has perseverance. Though this method does not necessarily deliver perfection on day one… or day five… over time, it matriculates into a strong cohesive team with a shared vision who will reach their goals.

manager blog skyrun teamwork
I for one am immensely grateful to work for and with Steve. At each turn, he shows me respect, appreciation, and support. He is wonderful to be with and around, and you can't help but want to succeed for him. Though not in a "Barritory" (eh, Barry Territory for those non-millennial readers) the support from Barry too is exquisite if more technical in nature. Anytime I have an issue, a feature request, or a question; he is always right there with the solution. The systems he has built streamline my workflow and create a guest experience easy to sell.

So what’s next? “Besides World domination!?" Steve jokes. "I'd like to be a brand." I don't know if SkyRun can be a verb one day, but He'd like that, "I want to SkyRun my place." Perhaps. For now, one thing is clear. SkyRun is growing.

For those out there who dream of running their own business, Steve says the more, the merrier. If you want to get involved, that’s great for you and great for SkyRun because every territory becomes more valuable with scale. To date, no one has ever re-sold a territory without profit, even without properties. It’s a great lifestyle, its fun, you get to work where you play, it’s a lot of hard work but where else can you work where you play? And it’s lucrative.

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Steve says you don't need to waste twelve years making the mistakes he and Barry made. All the bumps, bruises, and false starts have been dealt with and can be learned from. That's a big piece of what SkyRun is. You get to skip all that by joining the family. As they say, who is the smartest person in the room? The room. The collective brain trust and accumulated knowledge over those 12 years give SkyRun a broader perspective that gives each new location a big head start.

Hard to see why he was such a good salesman eh? :- )

I know for me, here in Aspen it sure is working, and I'm greatly appreciative as well. Perhaps this world domination thing won't be so hard… Though it will be more like world service with a smile.

That’s more fitting