How asking a “What if…” Question Helped Me Launch a Surf Travel Company in Brazil
I spend a large share of my executive coaching time helping leaders make the shift from being a “manager” to being a “coach” to their teams. This applies to first time managers as well as long-tenured CEOs. The ability to ask powerful, thought provoking questions is one of the critical skills to master as a coach. Asking a team member the right question at the right time can create awareness of blockers that might be getting in their way or uncover new possibilities they had never considered.
As individuals, we can also use questions to challenge assumptions we have about ourselves and tackle self-limiting beliefs. In The Savage Leader, I shared the story of how serial entrepreneur Michel Kripalani used a “How might that work…?” question as the jumping off point to start a mobile app company around the Dr. Seuss series of books. Doing so helped him beat back his self-limiting belief of his readiness to start a company and basing it on a child’s classic.
I used a similar question as the genesis to launch my first company, Nexus Surf, a surf travel company based in the South of Brazil.
Overcoming Doubt and Fear: How Asking a “What If…” Question Led to the Launch of Nexus Surf
In 2005, Hans and I emerged from the early morning surf at El Porto in Manhattan Beach and started walking to our cars and back to our busy lives in the corporate world. Hans was working for a large, New York-based law firm doing mergers & acquisitions work for some of the world’s largest companies. This meant 100-hour weeks grinding in the office, a sunless induced vitamin D deficit despite living in LA, and a cell phone that never stopped buzzing. For me it was helping large, successful companies become even more successful. The lifestyle and lack of purpose prompted us to turn to each other and exclaim almost simultaneously, “There has to be a better way?!” Our respective commitments to the tried-and-true path infused that statement with a sense of doubt as neither of us were sure that there was another way. Working in consulting and law was the “sure” path, but also the soulless path, at least for the two of us.
At the time, Brazil was on the come up – Havaiana sandals were all the rage, acai was a hip menu addition at local restaurants, Brazilian bikinis were a thing (well, they always have been a thing), and Brazil was lined up to host the Olympics and the World Cup.
Meanwhile, the surf industry was blowing up as kids across the globe donned Billabong, Quiksilver, and Hurley logos to connect to the adrenaline fueled and awe-inspiring world of surfing.
Our discussion quickly shifted from our morning surf session to new business ideas. “Surfing has really taken off and Brazil is on fire,” Hans said. “How could we combine the two as part of a business and get us out of the corporate grind?”
After a long pause, I asked, “What if we started a surf travel company in Brazil?” Rather than ask, “Could we start a surf travel company in Brazil?”, which would have sparked doubt and fear, the focus was on an inspiring question leading with a bold “What if…” question. Narrowing to a “Could we…?” type of question surely would have led us to focus on the facts that we were still newbie surfers, we both lacked experience starting companies, and that Brazil’s perceived safety issues might scare off tourists from the United States.
Instead of getting bogged down in why this wouldn’t work, we shifted to testing the idea. “Let’s call Ryan!” Hans suggested. Ryan was also slogging long-hours as a lawyer and we thought he could be our ideal customer. “Ryan,” we started immediately after he picked up the phone. “How much would you pay for a week of beachfront accommodations, daily surf excursions or surf lessons, VIP nightlife access, and daily breakfast delivery?” His answer stunned us and validated our idea, though not exactly scientifically. “Let’s do it!”, we both exclaimed buoyed by our newfound entrepreneurial hubris. This was the beginning of The Nexus Surf adventure, which provided both painful lessons as well as experiences that changed what I value in work, love, and life. Lessons about the importance of alignment, the importance of values, and how purpose outlasts passion that I’ll cover in future posts. Stay tuned as there will be more to come…
How to Apply This Lesson
The next time you are faced with an exciting new opportunity that might spark a bit of fear or doubt, ask yourself a question that starts with “What if….” or “How might that work…” instead of “Could that work….” or focusing on all of the reasons why an idea, project, career move, or life change is doomed to fail. Doing so will help you start to overcome your self-limiting beliefs and make meaningful changes in your life.