Jaclyn Baumgarten of Boatsetter: “Build a diverse and talented team”

Build a diverse and talented team. As I have built out the Boatsetter team, my goal is to bring together diverse talent with unique worldviews, insights, and language skills. I learned early on to have the maturity of character to invite and encourage challenge within the team and to hire people who think differently enough […]

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Build a diverse and talented team. As I have built out the Boatsetter team, my goal is to bring together diverse talent with unique worldviews, insights, and language skills. I learned early on to have the maturity of character to invite and encourage challenge within the team and to hire people who think differently enough from me to create creative tension within the team. This creative friction ultimately makes our product, communications, and policies better and helps us avoid mistakes. Your company is greater than the sum of its parts because of the effective collaboration of your team members.


As part of my series about the “How To Take Your Company From Good To Great”, I had the pleasure of interviewing Jackie Baumgarten.

With two decades of experience as a startup expert, seasoned leader, change agent, and founder of new industries, Jaclyn Baumgarten is an internationally-recognized tech entrepreneur and innovator credited with building peer-to-peer boat rentals into a globe-spanning industry. Jaclyn is currently Co-founder & CEO of leading boat sharing startup, Boatsetter, where her strong leadership birthed the peer-to-peer marine insurance policy that launched the industry.

Previous experience ranges from creating new cutting-edge technology 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, as well as tenures with PwC, IBM, and Westfield Corp.

Jaclyn has been recognized as one of Inc Magazine’s 2019 Top 100 Female Entrepreneurs and 2018 Endeavor Entrepreneur of the Year in Miami. She is a member of Young Presidents’ Organization (YPO) as well as a member of the Board of MasterCraft Boat Holdings, Inc. (NASDAQ: MCFT).

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 joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

When I was a child, some of my happiest experiences were when my father would take my brothers and me out boating on Lake Michigan. I always felt that experience shaped my life and love for all things water and outdoor leisure. In 2012, when I decided to launch my own company, those fond childhood memories of boating were never far from my mind. As I bounced business ideas around with my dad and brothers, who were also entrepreneurs, they mentioned how they were considering selling their boats because of how little they used them compared to the cost of upkeep. The idea behind Boatseter struck me there and then: wouldn’t it be amazing to make the water leisure experiences affordable and accessible to anyone while also helping owners offset the cost of owning a boat?

When I launched, I had been managing teams and launching in-house ventures for over 15 years and already had a strong professional network. My time working for PwC and IBM, in commercial real estate development, and as an intrapreneur for Westfield Corporation, gave me the foundation I needed to successfully build my own company. Throughout my career, I had always loved building things, be they teams, business divisions or actual buildings, and now I’ve gotten to spend the last decade building my vision that has become Boatsetter — something that not only connects people with experiences but gives owners a tool for earning money with their boats. I see Boatsetter as a marketplace of shared experience that keeps boating alive within families and cultivates the next generation of boaters.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Building a new marketplace company from scratch without any money was one of the first and one of the hardest problems I first had to tackle. I pulled together the first money to fund my idea by selling my condo, tapping into my hard-earned savings from 15 years of working in corporate America, and not taking a salary for two years. That was my seed capital. I was and will always be, all in on Boatsetter. It was very lean for the first few years — sleeping on a mattress on the floor in my bare little apartment in Silicon Valley and sleeping on friends’ couches when I traveled. Of course there were many times where I questioned whether I was going to be able to make it, but I firmly believe that to be a successful entrepreneur you have to fully commit to simply never giving up. Failure only really arrives when you stop trying. I pulled this company back from near-zero a number of times in the early years, and built back many times from what felt like they should have been death blows. But I am, at my core, someone with unwavering grit and tenacity. That has allowed me to survive and thrive in situations where most people would have folded and decided to step out. For example, early on, I had spent over a year and most of my remaining runway building and negotiating a partnership with a major manufacturer who was going to fund for millions of dollars and provide marketing access to their huge customer base. At the last moment, shortly before signing and as our remaining bank balance was getting perilously low, a competitor swooped in, and through a relationship with a board member, snatched up that partnership and funding. I felt defeated, and one of my advisors even recommended folding. But instead, I kept on building. Two years later, I acquired that competitor, and I now have the relationship with that manufacturer.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

Here’s the philosophy I follow: There are no right or wrong decisions, just the best decisions you can make in a given moment. Another way to put it is, you have to make the decision right. And, if you make enough decisions right, solve enough problems, you end up building something worth building. In hindsight, there are things I’ve learned and things I’d do differently, but I wouldn’t call anything a mistake per se, because I feel that at every moment, I’ve held myself to the practice of making my decisions right.

What do you think makes your company stand out? Can you share a story?

Boatsetter isn’t just a transaction between people and boat owners. It’s sharing the on-the-water experience and cultivating the next generation of boaters. I’ve always seen Boatsetter as a way to build and grow the entire recreational boating industry, bringing entirely new demographics and Millennials and Gen Z into what had, up until Boatsetter, been the rapidly greying world of boating.

We are creating a marketplace where people can share water and outdoor leisure with those who may have thought boating was out of reach, whether because of the cost associated with it or inexperience on the water.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Fiercely protect your time. It is your most valuable resource as an entrepreneur, and you only never can have more than there are hours in a day. Keep working hard and trust the data. Equally important, is investing in your company. I see myself as a servant leader and that means, investing in your tech, your employees, and your customers. Hire people smarter than you are in the areas you are lacking, let them explore their field and test and fail and then test again. Refine your tech with the end user always in mind so they are surprised and delighted with the ease of use and practicality.

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?

No one can do things alone so taking the time to make a social investment is a wise decision. Building a strong and effective circle of advisors and mentors is how you open up access to experienced professionals and expertise that is often costly. An effective group of advisors and mentors can help you avoid unnecessary mistakes, open up doors, identify partnership, employees, investors, funding, and other groups that align with your mission and can help you execute on that vision. I would recommend anyone thinking about starting a business to do this today, right now. Building your network of advisors is an investment you need to make; ask for help from those who have more experience than you do and are better at the traits you may lack. In my case, I’ve brought on advisors for Marine Industry Expertise and Product Expertise & Marketplace Expertise to help guide decisions, but also to help us think outside the box. Our goal is to open up access to a legacy industry and having that foundational expertise is important to mapping out where boating is going in the future.

Ok thank you for all that. Now let’s shift to the main focus of this interview. The title of this series is “How to take your company from good to great”. Let’s start with defining our terms. How would you define a “good” company, what does that look like? How would you define a “great” company, what does that look like?

For Boatsetter, our goal is to be the number 1 destination for on the water experiences. Boatsetter will lead the digital transformation in the boat rental industry and plans to expand beyond just boat rentals to include many verticals similar to the “Amazon of Boating.” That requires a continued investment in our technology, making it more intuitive and easy for the customer. When I first launched, I had the dream of taking the experiences of being on the water and making them accessible to everyone. I envisioned harnessing technology to completely shift the way people experience the boating world. Who you are, what your boating background is, and how much money you have in the bank shouldn’t be barriers to accessing boating experiences. The boating industry has an enduring reputation for being a luxury activity reserved only for an elite few with the financial means to access the water. Stats on boat ownership demonstrate the industry’s exclusivity and total lack of diversity: almost completely white, male, mid- to high-end net worth, average age 58 years old and rising yearly. Boatsetter is changing who the average boater is: Nearly 80 percent of our renters are under the age of 45, half are millennials, and more than a third are women. And our fastest growing demographic is Gen Z. As we’ve seen in industries like hospitality and real estate, technology has the ability to open access to experiences that were previously unreachable. Boatsetter was built with the vision that boating, and the incredible experiences people can enjoy on the water, should be available to everyone. That is what a great company looks like and what we are working to achieve.

Based on your experience and success, what are the five most important things one should know in order to lead a company from Good to Great? Please share a story or an example for each.

  1. Be a servant leader. This leadership style is the most important trait you can possess. I have found that hiring the most talented people, people who are smarter and better, and empowering them to succeed produces spectacular outcomes. An absence of ego, and an ability to drive consensus and collaboration all foster an environment where everyone knows that they have a voice and they are expected to contribute. That leads to the next four points.
  2. Build a diverse and talented team. As I have built out the Boatsetter team, my goal is to bring together diverse talent with unique worldviews, insights, and language skills. I learned early on to have the maturity of character to invite and encourage challenge within the team and to hire people who think differently enough from me to create creative tension within the team. This creative friction ultimately makes our product, communications, and policies better and helps us avoid mistakes. Your company is greater than the sum of its parts because of the effective collaboration of your team members.
  3. Surround yourself with a team of advisors. Building a strong and effective circle of advisors and mentors has been critical for our development. It has offered us access to experienced professionals and expertise that we would otherwise not be able to afford. An effective group of advisors and mentors can open doors and help you steer clear of unnecessary mistakes. Working closely with advisors in the marine space was important for learning what has worked in the boating and insurance spaces in the past and then bringing new perspectives to help evolve those ways of thinking. This allowed us to evolve a legacy industry and bring them into the future with me.
  4. Let data guide your decisions. Data drives all the decisions I make today. When I first started out, I leaned toward letting my gut guide my process. As you grow, you learn that the data must be the driver behind your decision making process. Data illustrates exactly what is working, what isn’t; who you audiences are or could potentially be; how back-end processes talk to one another and what could be done better. It’s the
  5. Be ready to sacrifice. A new business is demanding and problematic. As you are tenaciously solving all the problems and crises that are inherent in a new business, you will very likely find that it will consume all your time, all of your energy, and very likely lots and lots of your own money. The sacrifices aren’t just time and money. To keep Boatsetter alive and growing, I’ve had to sacrifice some of the most important moments of my life. Instead of going on my honeymoon in 2016, I flew to New York to meet with the investors to secure much-needed investment. If you want to be an entrepreneur, expect that for the first few years you will most likely have less space in your life for hobbies, vacations, relationships, family, friendships… even sleep. You will have to work very hard to keep your health and the health of your relationships in good shape. I’ve been very lucky that my husband is also an entrepreneur and he completely understands this life and totally supports me.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. Can you help articulate for our readers a few reasons why a business should consider becoming a purpose driven business, or consider having a social impact angle?

Boatsetter, at its core, is a community, and we believe everything stems from how we treat each other and our community. That’s why one of our core values is “Mind your Wake” — as we do our work, we always keep in mind the lasting impact we leave on our planet. We’ve focused on growing our social impact program which includes Boater Safety Education and Waterway Cleanups. With our investors, we created a fund that lets top owners direct money to the charity of their choosing to help with preserving our waterways and the environment. As a leader, I think it’s important to define values and systems that employees can look to and actively experience how their small, conscientious actions can add up to meaningful positive impacts.

What would you advise to a business leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth and “restart their engines”?

Invest culturally in supporting innovation, which means changing the dialogue with the team and giving them room to try news things and even giving them the opportunity to fail. Invest in your employees. It’s easy and often most comfortable to bring in and surround yourself with people who are pretty much like you. But, that creates an echo chamber. Having the courage to hire great professionals who challenge your way of thinking. That will make you a stronger team and it will help shake things up when you need it most. Investing in your employees is incredibly important. Let them be creative, let them go outside their own comfort zone and refine and learn new skills. That will lead to new ideas and new ways of thinking that will shake loose stagnation. You also have to invest in your technology. Reexamine how your tech is working and put your efforts towards improving it with the end user in mind. How can you make changes that will surprise and delight your customers? Doing so will pay dividends in the future and give you a leg up over our competitors that are investing in customer acquisition and driving lead generations for sales teams to close. But, this also ultimately goes back to the culture you create. When you are a servant leader — empowering your team and challenging them to go outside their comfort zone — you cultivate an environment that constantly evolves and innovates.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

During the first month of the pandemic, I was incredibly nervous about the impact this would have on Boatsetter. Now, more than a half a year later, it’s clear that the way we usually socialize has changed for the foreseeable future, if not irrevocably. It’s an intense, uncertain time and no one is immune to the stress of this moment, which is why identifying safe ways to reconnect with loved ones, and be outdoors, will be more important than ever to manage our physical, mental and emotional health this year. Instead of looking at this year as an insurmountable challenge, we decided to remember our core principles of investing in our people and our tech- and it paid off. Boatsetter provides a seamless way for people to reconnect at a time when our collective health and wellness is dependent on our personal safety. We recognized that as many of us have experienced the stress of countless hours in front of screens, social isolation, or the chaos of managing children out of school, the opportunity to spend a day on the water can be the perfect local refuge. We doubled down on what we know worked best for our team, and leaned into serving the fundamental human need to connect with loved ones and nature. The global pandemic has had a profound impact on how people travel and enjoy leisure experiences. More families are “stay-cationing,” travelling regionally and finding creative ways to take advantage of activities locally or regionally, evidenced by surges in planned RV trips and short term rental bookings. People are spending much less time planning vacations and more time spontaneously looking to escape the monotony of everyday life in isolation. That’s why Boatsetter saw a drastic change in booking behavior. Pre-COVID, bookings were made at least two weeks in advance — now, most bookings are made less than 48 hours in advance of the outing.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

How hard it is to successfully execute your vision. It requires maintaining cross-functional discipline and building the right processes and procedures to ensure consistency. Entrepreneurship is an opportunity to take a vision that you have, invest all your creativity, intellect, energy and passion in it, and create something amazing that changes your life, and possibly the lives of millions of others. But, without a well-thought out execution plan, without internal and external process, you can’t hope to bring that vision to life. Processes have to be crafted and tailored to your business. Crisis can happen when the wrong processes are put in place and you fail to execute on the right ones.

As you know, “conversion” means to convert a visit into a sale. In your experience what are the best strategies a business should use to increase conversion rates?

In order to optimize conversion the fundamental requirement is having data and visibility throughout your product. You can’t A/B test to see what works if you don’t have the data. But, more importantly, the greatest impact on the conversion rate is defining the perceived value of your product and its relationship to price. When the perceived value is greater than the price being charged, the result is an increased product conversion rate. The greater the delta, the larger the conversion rate improvement. Many startups skip the step of defining perceived value and generally force their attention to harder conversion rate optimization projects.

Of course, the main way to increase conversion rates is to create a trusted and beloved brand. Can you share a few ways that a business can earn a reputation as a trusted and beloved brand?

A business can earn trust and a positive reputation by building a product that works and works well, and through consistent and targeted communications with audiences. What this means is that you are not just pushing out messages about your company, but you create a dialogue between you and your customers. And that can be done through the more obvious communications channels like instagram and Facebook and through the media. However, this two-way communication is also achieved when you create a product that works for the customers. In fact, the latter is the most important way to build a positive reputation. If your tech doesn’t work, if your product isn’t created with the customer in mind, all the spin and Instagram-worthy creative in the world won’t change that. Great tech is a reputation builder. Ultimately, to have a great product circles back to being the kind of leader that paves the way for your team to create the best product.

Great customer service and great customer experience are essential to build a beloved brand and essential to be successful in general. In your experience what are a few of the most important things a business leader should know in order to create a Wow! Customer Experience?

Build-up, cultivate and constantly support the team of people behind your technology. Ensure that, behind your beautiful and seamless computer interface, are knowledgeable and emotionally intelligent human beings that are building technologies and systems based on years of expertise, industry intelligence, and an intuitive experience based on deep understanding, not assumptions. I don’t take this lightly, which is why I’ve invested in creating a user experience that is backed by years of groundwork that makes the peer-to-peer rental process easy and truly safe for owners and renters.

What are your thoughts about how a company should be engaged on Social Media? For example, the advisory firm EisnerAmper conducted 6 yearly surveys of United States corporate boards, and directors reported that one of their most pressing concerns was reputational risk as a result of social media. Do you share this concern? We’d love to hear your thoughts about this.

Social media opens up access to industries for all demographics. It opens doors into people’s lives to make a product, a lifestyle, or concept attainable. That’s what we are doing here at Boatsetter and social media has been a large part of allowing people know that the boating experience is now available to them through Boatsetter, all around the US and across the world. We strive every day to open up the boating industry to the next generation of boaters. Wealth, experience, gender and ethnicity should no longer be a factor in accessing the boating lifestyle. Boatsetter was built with the vision that boating, and the incredible experiences people can enjoy on the water, should be available to everyone. That message is something we want everyone to see, feel, and hear. Social media helps open that channel of communication between us and our customers. Is there risk of reputation harm if someone posts something negative? Of course, but that is a natural part of actually listening to, and being aware of reality, and having your company reacting to and serving the real world. I would personally rather know if someone had a bad experience so that my team can have the opportunity to fix it. It all goes back to dialogue. When you have two-way communications with your customers, when you are open and accessible, you can turn a negative into a positive experience. Being in the dark is the real reputation risk.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

For me, it boils down to not investing and trusting your team. You have to build a team that is filled with the most talented people in their fields. You have to bring together people from all backgrounds, experiences, and languages. Doing so gives you the best chance for amazing outcomes. Letting your team challenge the way you think. You want debate within your team. You want team members who see the world from different perspectives and can call out and fill in the blind spots in each other’s thinking so you are a company that makes fewer mistakes and creates a better product.

Homogenous teams get you nowhere — they tend to run you quickly, unchallenged, in one direction, and by the time you realize you’ve rushed down a dead end path, you’ve missed your opportunity to make a graceful course correction.

Thank you for all of that. We are nearly done. You are a person of great influence. If you could start 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. 🙂

We are doing it in so many ways here at Boatsetter. I have a deep love and respect for nature. Being on the water is the best feeling in the world. However, without clean water, without investing in our environment, that experience changes. At Boatsetter, we want to take care of the environment because it’s what makes this experience a spectacular one for so many people.

How can our readers further follow you online?

@boatsetter on Twitter, Instagram, and Facebook

Personal Twitter: @JaclynBaumgarte

Personal Instagram (although I don’t post as much as I should): @jaclynbaumgarten

This was very inspiring. Thank you so much for the time you spent with this!

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