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Mike Kennedy of KOALA: “Fall in love with the problem, not the solution”

“Fall in love with the problem, not the solution.” Many have heard this quote before, and it obviously wasn’t stated directly to me. Yet it’s the simplest, most-effective mantra I’ve come across, and it has kept me from getting in my own way. Coming from a creative background, it has been critical for me to […]

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“Fall in love with the problem, not the solution.” Many have heard this quote before, and it obviously wasn’t stated directly to me. Yet it’s the simplest, most-effective mantra I’ve come across, and it has kept me from getting in my own way. Coming from a creative background, it has been critical for me to not conflate a consumer product with “art” and ensure that we are continually iterating to solve the fundamental problem we set out to address.


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Mike Kennedy, Cofounder and CEO of KOALA, a groundbreaking vacation marketplace that is set to disrupt the $30.5 billion timeshare industry with new tools and technology to empower timeshare owners and draw a new generation of guests. Kennedy oversees all aspects of KOALA, including product development, owner and guest relations, marketing, operations, and leading fundraising and finance efforts.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Like a lot of entrepreneurs, my ‘backstory’ winds all over: Born and raised in Queens, an abbreviated turn at college, short-term success in the music industry, and ongoing success in restaurants with a couple of neighborhood hotspots in Prospect Heights, Brooklyn. The one constant is that I’ve always approached things from a creative perspective, which honestly made me an unusual fit for real estate. Indeed, my Myers-Briggs score indicated I didn’t belong in the industry, and it was only because the wife of my current business partner at KOALA told the boss “you need to hire this person” that I landed at Hilton Grand Vacations at The Hilton Club. Once there, I looked at Timeshares through a creative lens and realized how broken the system is, how owners are struggling, and how I could transform it to benefit owners and draw guests who’d never contemplated it.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Introducing secure peer-to-peer technology into Timeshares is highly disruptive, particularly for an industry that focuses on keeping customers “in the ecosystem” as much as possible. Timeshare exchange companies act like middlemen, controlling inventory and making it challenging if not impossible for owners to resell or rent their Timeshares to defray costs. KOALA provides tools and resources to empower these owners to utilize or monetize their vacation ownership.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Trying to raise money on the “Audacity Of Zero” — that is, with no revenue, customers, or publicity. It didn’t work for us, and it’s funny to think that we actually pitched real Venture Capitalists and Angels on a concept based around Timeshares, an industry that most people, much less investors, don’t even take seriously. Zero tech (this was pre-MVP or minimum viable product) + zero successful exits as founders + zero customers = zero investors…you get my point. But we knew we were tapping into something, and that alone gave us reason to keep going.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

My O.G. mentor is my mom: She always pushed me to follow my path and instilled me with a great work ethic. She taught me two things in particular. First: “No work is below you when you need to earn a living, and if you need to earn a living to take care of yourself and remain solvent — then you do it.” She worked nights as a waitress in a diner to support my brother and I. Clean toilets, bus tables, grill burgers…whatever: There is no shame in hard work, there is only shame in being unreliable and insolvent (if you have the choice to be otherwise). The second thing she taught was: “Do whatever you are passionate about, just do it well and work hard”

My other mentor would be David Maundrell, now Executive Vice President New Developments at The Corcoran Group in NYC. He taught me so much about the hustle and “closing the sale.” If you can’t sell, it’s hard to be an entrepreneur: How can you raise money or even get your team to believe in your vision in the first place? These two taught me a strong work ethic and the art of selling, which ultimately helped set me up to be an entrepreneur.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

I think the term “disruption” can mean so many things and, when it comes to today’s startup market, it’s sometimes overused or even banal. Quite simply, disruption happens when a startup upends or even supplants the status quo.

Generally speaking, industry disruption is good: It means innovation is happening. That said, it also depends on what side of the disruption you’re on. If you were a somewhat-tech-savvy New Yorker looking for transportation in 2011, Uber was a great form of disruption. If you were a taxi driver, or worse, an owner of a notoriously expensive taxi medallion, then ride sharing was a very very bad type of disruption for you.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

  • “You are mining gold at exactly the right time.“ Shaun Stewart told us this before he joined KOALA as an advisor and then took a seat on our board of directors. It was reassuring to hear support from someone that understood supply and demand acquisition in the travel space.
  • “Fall in love with the problem, not the solution.” Many have heard this quote before, and it obviously wasn’t stated directly to me. Yet it’s the simplest, most-effective mantra I’ve come across, and it has kept me from getting in my own way. Coming from a creative background, it has been critical for me to not conflate a consumer product with “art” and ensure that we are continually iterating to solve the fundamental problem we set out to address.
  • “A person who never made a mistake never tried anything new.” — Albert Einstein. Love this quote. It may be played, but it’s essential to the mindset of any entrepreneur. One cannot be afraid to fail and learn over and over until one prevails. Failure and success are not mutually exclusive.

We are sure you aren’t done. How are you going to shake things up next?

You mean dusting off an industry that hasn’t seen innovation in 45 years isn’t enough?

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

The Lean Startup by Eric Ries has had a massive impact on our behavior and culture as a company. We encourage new hires to read it. The Build-Measure-Learn cycle Ries puts forth is a simple technique to understand your customer and what they actually want, not what you think they want. I’m also currently obsessed with startup podcasts, which I consume constantly. I love stories about company founders: Hearing how they floundered, struggled, and ultimately prevailed is so inspiring. The more you listen, the more you realize you need to fail consistently to find success and why so few are prepared or willing to take that journey. Podcasts like: ‘Y Combinator’, ‘Masters of Scale’ hosted by Reid Hoffman, and ‘How I Built This’ with Guy Raz — I cannot get enough of them.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Do. Or do not. There is no try” — Yoda. Never mind that it came from a Star Wars movie — it doesn’t make it any less true and fundamental to the spirit of entrepreneurial “grit” and mental fortitude. Follow through with what you set out to do and make things happen beyond the scope of ease and reason. As Henry Ford once said: “Whether you think you can, or you think you can’t…you’re right.”

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

There are the obvious answers like climate change and protecting our natural environment — but as important as those topics are, it’s not a space in which I can currently have any major impact. I can however, help millions of struggling Timeshare owners overcome real financial burdens — particularly those of an older age group — and that feels really good.

How can our readers follow you online?

My Linkedin and Instagram accounts are the two places I share my passions and progress. Follow me!

This was very inspiring. Thank you so much for joining us!


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