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Kieran and Deborah O’Keeffe :” Don’t rush hiring, make sure you get the right people”

Don’t create an echo chamber, create a team that isn’t afraid to challenge you when necessary. Look outside regular recruitment avenues and find people who think differently than you do. Create an environment that fosters involvement in every aspect of the business, where everyone learns from one another, and you’ll create a sum far greater […]


Don’t create an echo chamber, create a team that isn’t afraid to challenge you when necessary. Look outside regular recruitment avenues and find people who think differently than you do. Create an environment that fosters involvement in every aspect of the business, where everyone learns from one another, and you’ll create a sum far greater than its parts.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Deborah and Kieran O’Keeffe, COO and CEO of SkiBro. SkiBro is a marketing, aggregation, and booking platform for ski lessons headquartered in Val d’Isere, France. Kieran O’Keeffe is a former British & Irish Universities Boxing Champion and UCC Guinness Sports Star award-winner, after leaving university Kieran worked in software roles for Barclays, Lufthansa, and Deutsche Bahn. He founded his first internet company in 1998 which grew to have offices in Germany, the UK and India, but unfortunately folded during the dot-com bust. Since then, Kieran has founded 3 successful companies, the largest of which — MobileWebAdz — served 45 billion ads per month in real-time across 130 countries, competing directly with rivals such as Google’s Admob and Apple’s iAds. MobileWebAdz also ranked in the top five places in the Sunday Times Tech Track 100 for three years in a row as well as placing in the HSBC International 200 for Fastest-Growing International Sales in 2016. Currently Kieran lives between his native Ireland and Val d’Isere, France which is the headquarters for his newest venture, SkiBro, a platform marketplace for ski instruction. After leaving university Deborah O’Keeffe began her career as a bond broker for Cantor Fitzgerald before becoming a Senior VP at CEB where she spent 12 years working directly with and advising CFOs, Heads of Corporate Strategy and COOs at corporations with minimum 50 billion dollars revenue. At the same time she managed a team of 60 people and a 70mm dollars P&L, growing their primary market from 2mm dollars to 35mm dollars in 5 years. She also was a primary investor and NED at MobileWebAdz before becoming co-founder and COO of SkiBro.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

We both come from working class Irish families. Kieran is from Killorglin — a town of just over 2000 people in County Kerry, Ireland — where his father was a police officer, his mother was a nurse, and he grew up working as a farmhand on his uncle’s farm. Deb is from Carlow which is about 50 miles from Dublin and, with a population of 24,000, is a booming metropolis compared to Killorglin. Both her parents were factory workers and her first — and toughest — job was picking strawberries.

Our respective backgrounds definitely gave us both a deep appreciation for the value of hard work but they also made us both look for ways to work smarter; opportunities we could forge for ourselves to create something bigger.

Another common thread to both of our upbringings which has enormously helped both of our careers is the importance of storytelling in Irish culture — it’s an innate part of who we are and is an extremely powerful tool in today’s business environment.

Stories help to solidify intangible, abstract concepts and make sense of complex ideas. The power of a strong, authentic, story is invaluable when you’re pitching a very-early stage business — it enables people to truly ‘see’ your vision and become emotionally invested in your journey.

Of course, your numbers still need to add up but whether you’re raising capital or building an outstanding team don’t underestimate the importance of narrative to motivate, unify, and inspire loyalty.

Looking back at where we started and where we’ve ended up, it’s really been an incredible journey in more ways than one, especially when you consider Ireland’s got tons of rain but absolutely no snow!

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

We both love the mountains and Kieran’s convinced that he was Ireland’s first-ever snowboarder so starting a new life in the Alps is a dream come true. Coming from rural backgrounds ourselves we also wanted our young son to experience growing up in the countryside, but at the same time we loved our careers which kept us tied to cities.

The idea for SkiBro came to us three years ago from our French co-founder, Benjamin, who is a London-based banker and had been involved in the potential flotation of our London-headquartered tech business. He knew how much we love the mountains and came to us with the idea for “Uber for ski lessons”.

The “Uber for X” model was very hot at the time and we were sure that there would have already been a massively-funded player in Silicon Valley, but we did some digging we found that (almost unbelievably) there wasn’t.

We saw a major opportunity, with no American competition, that would allow us to live in the mountains and snowboard everyday; it was a no-brainer. We flew straight to the Alps to do some quick on-the-ground research and we haven’t looked back.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

Don’t overthink it, just get stuck in. Your idea probably isn’t perfect, but by launching quickly and making changes on the fly you eliminate dead-time that might allow other entrants in the market to take your place.

Also, the best way to find out what’s wrong with your model is in the marketplace. SkiBro has come a long way from being “Uber for ski lessons” and will evolve even more in the future, both in ways that are on our current road-map and ways we likely haven’t even thought of yet.

Get to market as soon as you possibly can and quickly incorporate what you learn into the next iteration of your offering. Also, try to surround yourself with the best possible people to make the inevitable transitions along the way as smooth as possible.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

You need to check that the market is large enough to sustain a business of the size you think you’ll need to get to in order to be satisfied. You need to really evaluate what makes you happy. If you know that running your own small business, living simply, and enjoying your hobby will make you happier than your current job then what are you waiting for?!

However, if your definition of happiness means you’re going to have to build a good-sized company then you need to either find an unfilled niche or be better than everyone in an existing niche. Both are much easier said than done but if you think you’ve got the idea to make it happen there’s only one way to find out… Unless you’re happy to live your life wondering ‘what if?’ you’ve just got to get yourself out there and take the risk.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

What’s been good for us is being involved in the industry but still remaining one step removed from the activity we love. For example, if you come from a banking background but love cooking and become a chef, it’s easy to see how you might get bored. What might be a better fit would be to become a restaurateur — you get to be involved in the food side whilst at the same time using your existing passions and skill set.

That example might not hold true for everyone — some people would love life as a chef — but for us setting up a tech platform in the ski industry has allowed us to be very close to the activity we love, but still keep it as a hobby. The day to day skills we use are closely aligned to what we did during our previous careers and getting out on the mountain still feels like an incredible treat. It’s impossible to not love snowboarding every day during your lunch break with your friends and loved ones.

One of the most important criteria for us when hiring was a genuine passion for winter sports and life in the mountains. We used some unorthodox recruitment methods to find our team but the people we’ve assembled are truly outstanding and a big part of our company culture is that everyone has the freedom to go out skiing or snowboarding for a couple of hours every day if they want to. It reduces stress, increases camaraderie and helps offset the heavy workload necessary to make any startup a success. You’d also be surprised how often you have a real ‘eureka!’ moment while you’re sitting on a chair lift.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

The positives and negatives to running your own business are really two sides of the same coin:

You have complete freedom to determine your path, but if you make poor choices you have no one to blame but yourself. You have the opportunity to create a significant amount of wealth for yourself, your family, your investors, and your team (who quickly become your second family) but if you don’t, you feel like you’ve let them all down.

There’s an immense sense of liberation to being your own boss but it’s sometimes overshadowed by a consistent existential stress; 49% of all entrepreneurs deal with mental health issues as a result, so making sure you are mentally resilient and prepared to bare the weight of your world on your shoulders is crucial.

Find an outlet where you can let go of everything, even if it’s just for an hour a day. For us that’s going snowboarding, for others it’s yoga, meditation, or going to the gym. Whatever it is for you, make sure you take care of your mental and physical well-being — the rest will fall into place.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

The additional layer of uncertainty involved in this industry. Because skiing is a relatively niche, and very traditional, industry there’s a real lack of tangible data to base your decisions on, so you often find yourself relying on educated guesses and gut feelings.

Of course, this is true for many businesses but we’ve felt it more with SkiBro than we have in the past. Luckily, the team we’ve built in Val d’Isere is better than we could have imagined and we’ve been right a whole lot more than we’ve been wrong.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Ha ha — we each think that at least once a week.

Kidding aside, entrepreneurs put our lives and souls into our companies — you can’t just walk away like any rational person might do when things get hard. You have to think outside the box and find a way forward — people rely on you and you have to keep going.

It’s normal to daydream a little now and again but if we really wanted to have a ‘normal’ job we never would have started this journey in the first place, we were ‘comfortable’ before but comfortable wasn’t enough for us.

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?

When we first started to drive around the Alps to do our initial research Google Maps often sent us to use a tunnel that turned out to be closed or suggested we drive over a mountain pass that was so full of snow it was actually being used as a ski run. It cost us so many hours of driving. Last winter one of our new developers actually tried to drive over one of these passes and had to reverse a couple miles back down a narrow, windy, snow-covered mountain road with a sheer drop off one side…

“Never trust Google Maps” has become a maxim around the office. It’s a good metaphor for the unexpected problems we sometimes face as a tech company operating in a very traditional space. As much as Silicon Valley is about ‘moving fast and breaking things’ that’s not how things work in traditional Alpine villages that have largely been populated by the same handful of families for the last millennium.

We’re scaling very quickly but our aim isn’t so much to disrupt as it is to integrate with — and improve upon — the existing infrastructure, to grow the market as a whole and make things run more smoothly for both consumers and providers.

Who has inspired or continues to inspire you to be a great leader? Why?

For us, Bill Gates is the epitome of a great leader. Not only has he created a company that has quite literally changed the world, he’s also using the profits he’s earned to make the world he’s helped shape a better place. From eradicating preventable disease, to fighting against global warming — if every leader were a bit more like Bill Gates, then the world would be a better place indeed.

How have you used your success to make the world a better place?

We contribute to a couple of charities that are close to our hearts and the industry we work in, namely:

Protect Our Winters — the leading climate advocacy group for the winter sports community.

SnowCamp — a very unique British charity that introduces youth from urban areas to skiing and snowboarding as a means to gain life skills, qualifications and work experience.

ShredSafe — which provides free avalanche safety education for seasonal workers in the Alps.

In a less concrete sense our platform helps to democratize the ski-instruction industry so that independent, freelance instructors are listed next to even the biggest ski schools and are on an equal footing for how they’re marketed.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Jump in with both feet. If you try to hold on to ties from your past life or have some kind of safety net, you’ll only distract yourself.
  2. Don’t rush hiring, make sure you get the right people. If you need to get something done right now and don’t have the right person for the job, farm it out to a contractor. It may be more expensive in the short term but hiring the wrong person will be far more costly in the long run.
  3. Don’t create an echo chamber, create a team that isn’t afraid to challenge you when necessary. Look outside regular recruitment avenues and find people who think differently than you do. Create an environment that fosters involvement in every aspect of the business, where everyone learns from one another, and you’ll create a sum far greater than its parts.
  4. Plan your route to profitability and don’t be afraid to share it — the days of chasing nothing but growth are over. We’ve always placed a lot of value on getting profitable quickly and being explicit about these plans has helped immensely with investment.
  5. Your character will be tested just as much as your competency. Hard decisions have to be made on the road to creating a successful business, but that doesn’t mean you need to abandon your scruples.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. 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.

Human beings are incredibly creative and intelligent, but many are incredibly risk-averse. Everybody should roll the dice and change their life completely at least twice during their lives. Move to a new country, start a company, run for office — do whatever it is that you feel needs to be done! We can’t change the world unless we change ourselves.

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

It’s a bit cliché but Kieran’s dad always used to say, “If it was easy, everybody would be doing it”. It’s a simple sentiment but there’s a lot of truth to it and it’s kept us going forward when the risks are high and the workload seems impossible.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Robert A Katz, Chairman and CEO of Vail Resorts Inc which owns and operates nearly 40 world-class ski resorts in three countries, including household names like Vail and Whistler.

He has the best job in the world and does an amazing job at it. He’s not only revolutionizing the ski industry but also business leadership as a whole, from his corporate-leadership training program to his generous donation to Wharton to be used for research into emotional intelligence leadership, a woefully neglected area of leadership even in the ‘modern’ corporate culture landscape of 2019.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

Thank you Phil and Yitzi, it’s been our pleasure.

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