“Have extremely clear expectations of performance and clear KPI’s you can hold your division leaders accountable to. In addition, have one common KPI — like GMV, for example — that everyone in the company can look toward as the indicator of their shared success.”
I had the pleasure of interviewing Jaclyn Baumgarten, Co-founder and CEO of boatsetter.com, the # 1 boat rental community. Closing in on two decades of experience as a startup expert, Baumgarten is a seasoned leader, change agent, founding member of new industries, new divisions, and always leading the charge for scalable growth. She is the current Co-founder & CEO of leading boat sharing startup, Boatsetter, where her strong leadership led to the creation of the peer-to-peer marine insurance policy that launched the industry. Previous experience ranges from creating new divisions in Fortune 500 corporations to growing startups into $1B entities to spearheading one of the largest commercial real estate developments in the City of Los Angeles, including PwC, IBM, and Westfield Corp. Jaclyn holds a Bachelor of Arts Degree from Wellesley College (Cum Laude) and an MBA from the Stanford Graduate School of Business.
Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?
I come from a family of entrepreneurs going back a number of generations. Since I was a little girl, I had always foreseen myself launching my own company one day.
After I did the grueling NYC consulting thing at PWC and IBM, I spent a number of years as a commercial real estate developer with Westfield and then was in healthcare with Davita. In both of those latter two companies, I played the role of an “Intrapreneur”, launching new ventures under the umbrella of those corporations.
In 2012, I took time to focus on doing the research to figure out what business I wanted to launch. I decided I wanted to launch an internet marketplace. Some of my best childhood memories were of being out on the Great Lakes with my dad and brothers. I wanted to see if there was an opportunity to make that incredible experience of friends, family and nature more available to people. At about the same time, two of my brothers each mentioned to me within the space of a few days that they were considering getting rid of their boats, since they were costing them a lot of money, and were using them just a few days each year. I naively asked them why they didn’t just rent them out to cover their costs. They told me how that was impossible, since renting out their boats would void their recreational insurance coverage, and getting commercial coverage was prohibitive for such occasional rentals. There was no way at that time for them to make owning a rarely-used boat even remotely affordable. Right there, the idea for Boatsetter dawned on me. I could make it so that it was legal, safe, and easy to connect boat owners with people who wanted to get out on the water and make boating more accessible and affordable for everyone. I decided to build the “Airbnb of Boats”.
What do you think makes your company stand out? Can you share a story?
Our team is made up of people who really love being out on the water and have a deep understanding of boating that allows us to make the experiences simple, safe and amazing for our users.
For example, one of our customers wanted to propose to his girlfriend on a sailing catamaran out on San Francisco Bay, then sail with her down to the world-renowned Post Ranch Inn overlooking the Pacific Ocean on the cliffs of Big Sur.
That sounds just beautiful and romantic, but the reality of that sail is that, while San Francisco Bay at sunset is gorgeous, from there it’s a 150 mile overnight slog at 5–10 miles an hour upon the often cold, foggy and rough waters off Northern California. Even then, you can’t pull up the wave-thrashed cliffs beneath the hotel and get out — you’d have to dock at Monterey and take a car for an hour from there.
So instead, we helped him set things up to propose to his future wife in the warm, mid-day sunshine out on the Bay, sail to a little heliport, then take take an exhilarating, quick and comfortable helicopter ride down the beautiful California coast and land right at the hotel for a late lunch in their suite overlooking the water.
We make sure that our Boatsetter users have a truly wonderful and memorable time on the water, regardless of how much or how little previous boating experience they have; whether they are doing a dramatic and extravagant proposal like this gentleman, or simply taking a 24-foot runabout out with friends for the afternoon for $250.
Are you working on any exciting new projects now? How do you think that will help people?
We have an amazing collaboration going with Airbnb to provide their professional-quality on-the-water experiences for our customers all around the world. Our “Experiences” service that we run together with Airbnb allows people to spontaneously join a group of other individual travelers on really wonderful outings that provide them access to experiences that are truly unique to the cities that they take place in. For example, in Miami you can do wakeboarding lessons with a former national champion, on the nicest wakeboarding spot in the US — the warm, flat, open waters of the intracoastal waterway under the blue skies of south Florida. In Barcelona, you can join a 5th-generation vinter and sommelier aboard a sailboat and enjoy a sunset over the Mediterranean while tasting and learning about the most delicious wines Catalunya and Spain have to offer. In Los Angeles, you can set off into the Gulf of Santa Catalina with a marine expert and have an up-close and personal experience with the resident dolphins (sometimes hundreds) and the whale population along the way.
We have many, many more of these experiences available and in the works. With our “Experiences” service we’re even further expanding our ability to make life out on the water truly accessible to anyone with a smartphone and the desire to have a day they will never forget!
What advice would you give to other female leaders to help their team to thrive?
Remember that, above all, your job as a leader is to create the structure and environment that allows your team members to excel to the best of their abilities in their pursuit of fulfilling your vision. You must always be able to clearly articulate your vision to every person you are expecting to contribute to you achieving your goals and be able to explain to them how what they are doing contributes to your shared greater goal. Be generous with your knowledge and proactive with your communication. Always be thinking about the longer term objective and be creating the setting your team is going to need to continually move toward that objective. Keep funding and resources available, ensure the right people and skills are on board, line up the critical partnerships that will drive strategic growth, clear obstacles, and make sure that the culture you feel your team should have in order to thrive is understood, accepted and cultivated by all. Do not shy away from the hard decisions and difficult conversations; tackle them directly and without delay. If anything is threatening to poison your company, take care of it quickly and decisively. The well-being of your organization is your responsibility; be ready to make hard choices to protect it and enable it to thrive.
What advice would you give to other female leaders about the best way to manage a large team?
Hiring right matters enormously. Hire slowly and carefully. When you must, fire quickly and decisively.
Build a structure where you have good leaders who are able to very effectively motivate, steer and take full responsibility for their divisions. They should be your “one throat to choke” for everyone under them.
Have extremely clear expectations of performance and clear KPI’s you can hold your division leaders accountable to. In addition, have one common KPI — like GMV, for example — that everyone in the company can look toward as the indicator of their shared success.
As the leader of your company, ensure that there is effective and efficient cross-collaboration throughout the organization and that no division or group is getting siloed.
Envision, communicate, and nurture a strong and distinctive culture that you believe will empower your team to thrive. A clear culture provides gentle, but effective direction to the thousands upon thousands of micro-decisions your team will be making every day as they interact with each other and your clients, and as they build the systems that make up your company. As humans, we instinctively and automatically operate within the guidelines of cultures we chose to be part of. Set and cultivate your culture with deliberation and care and you will eliminate many problems before they can even arise.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
I had the good fortune of being taught very early the incalculable value of good mentors. Throughout my career, I have made it a point to seek out people who I knew could be great mentors for me, and boldly and humbly asked for their help. There is a group of brilliant and accomplished women and men who have said “yes” to my requests for their guidance, and their support and direction have been priceless to me. Their experience and wisdom has allowed me to avoid untold numbers of mistakes and their generosity with their networks has opened doors that would have otherwise been closed to me.
Among my mentors, I am fortunate to count Andy Sturner, the Chairman of my Board of Directors and the co-founder of Boatsetter; Laurence Tosi, former CFO of Airbnb and The Blackstone Group, Sandy Warner, former Chairman of J.P. Morgan Chase; Bill Anderson, President of Westrec Marinas; Peter Warnøe, CEO of Nordic Eye; Greg Ennis, MD of Peninsula Ventures and Director of the Stanford University DAPER Fund; and Laura González-Estéfani, Founder & CEO of TheVentureCity.
I would not be where I am today were it not for the help of others. I can’t recommend strongly enough the benefit of reaching out to people to ask for guidance.
How have you used your success to bring goodness to the world?
I’ve found that I am best able to contribute to the planet by supporting and mentoring other entrepreneurs who are building their own ventures to make the world a better place. I am fortunate enough to have been invited to work with a number of really incredible and effective organizations that nurture entrepreneurs like TheVentureCity, Endeavor, Women’s Startup Lab, 500 Startups, LAB Miami, and Miami Dade College. These are organizations that support the work of those entrepreneurs aiming to solve our world’s problems, providing them education, funding, and mentorship, and building ecosystems in which innovative entrepreneurship can flourish.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Eleanor Roosevelt was a brilliant mind and an inspiration to millions over the past century. Two of my favorite quotes from her are:
“Nothing has ever been achieved by the person who says, ‘It can’t be done.”
And its corollary,
“A stumbling block to the pessimist is a stepping-stone to the optimist.”
As a little, tiny girl with three much larger brothers who I wanted to play and compete with, I internalized a worldview very early on that much in life — especially the fun and satisfying stuff — is going to be difficult and is going to require a lot of effort. The phrase, “You’re not going to be able to do that,” came up a lot when I was trying to do something my large brothers were doing. It was so constantly evidenced to me as untrue when I went ahead and just did whatever it was, that that sentence very quickly became an empty and truthless inanity in my little mind.
This worldview has served me well. I really have a hard time believing there is anything at all I can’t do. I’ve always just assumed that obstacles are a natural part of any given path and in turn, a natural and even fulfilling part of any journey is getting over those obstacles.
How can our readers follow you on social media?
Thank you so much for these inspiring insights!