Wendell Holland: Lessons Learned from a Desert Island, Penn Law, and the Entrepreneurial Experience

Wendell Holland is an entrepreneur, Survivor winner, and a Philadelphia native who earned his J.D. from the University of Pennsylvania Law School in 2011. After clerking for the Philadelphia Court and Family Court, he took a leap of faith and built Beve Unlimited, a handcrafted furniture company. Years later, he achieved his goal of being cast on Survivor 36: Ghost Island and was sent to Fiji to compete for the million-dollar prize. Wendell quickly rose to popularity in the show and throughout the United States as the season was airing, and he was announced the Sole Survivor in 2018. Holland has most recently competed on Survivor 40: Winners at War in 2020. Wendell still works as a furniture designer for Beve Unlimited and has just booked his own HGTV home-renovation show called "Hot Mess House."

You graduated Penn Law and worked as a Clerk in Pennsylvania after you graduated, can you tell me a little bit about your experience at Penn Law and what guided the decision to pursue entrepreneurship after earning your J.D.?

My experience with law school was not the most fun experience of my life... I'll say that. I've always been someone that has been very creative and always needed an outlet–law school was a little different for me. I decided to go to law school because my father is an attorney and he suggested it. I did well in undergrad, and as a Philly boy, Penn’s the top place you’d want to go, and I got in and decided to go there.

What I will say is that one creative outlet that I found while at law school was a course called Visual Legal Advocacy, where we went out in the field and recorded documentaries about legal topics. I was able to scratch my creative itch so I still had my creative outlet in Law School. After I graduated, I went on to clerk in civil court and then family court. When I was in family court, I started building things for my house, and I’d post them on social media. People started having me building for them and buying pieces from them, so I had this cool little side hustle of mine where I was building and using that creative outlet again, which kind of organically turned into this business of mine.

Was it hard for you to make that entrepreneurial transition feeling the pressure from your father and going to a place like Penn Law?

I've always been the guy that did the things my parents told me. I constantly look for mentors, and my father was the most influential mentor I had growing up, so I always listened to everything he said…including going to law school, when maybe that wasn't my path or what was really in my heart. But I followed his advice, went to law school, started clerking and I think he knew that there was something different inside of me. He saw me start building things and what's funny is he was the person that taught me how to build things growing up– he showed me how to frame out our basement drywall, those kinds of things, because he is a very handy guy too, so I think because he saw that same inside of me, that wasn't something that he was willing to inhibit. He just let me do this as my side hustle that was making some good money on the side while my law clerk job was not paying much. My counterparts at Penn had these incredible jobs and I was working as a law clerk making okay money, but then there was this side business of mine that started gaining some steam, and I was making pretty good money doing that. I think my dad saw that I was able to juggle these two things. So, I think because he saw me do very well in college and do okay in law school, he wanted to kind of sit back at last and let me spread my wings finally as opposed to being the person that had more of an active hand in everything; it was time for me to spread my wings and fly, and I think he wanted to see if I could actually fly.

I’m a firm believer that everything happens for a reason, and it seems like your journey with entrepreneurship, law school, and Survivor was the perfect storm for you.

I think everything certainly happens for a reason with regards to all the things I did growing up. I was an International Studies major in college, and I've always been intrigued by other cultures and just someone that likes meeting and interacting with different kinds of people. Ultimately, I wound up on a desert island in the game of Survivor where I was able to draw on my experiences with so many different types of people and all of these lifelong lessons. I felt like I pulled from so many experiences in my past for me to do very well on Survivor. So it’s true things happen for a reason.

You are the winner of Survivor: Ghost Island and competed on Winners at War. While I'm sure you spent a lot of time focusing on your gameplay and strategy, you probably had a ton of time to reflect on your past and all your personal experiences. What were the main life lessons learned from your experience on Survivor?

I had two very different experiences on Ghost Island versus on Winners at War. On Ghost Island, I was coming in as a superfan who had been striving to achieve this goal for maybe seven or eight years. When I got out there, I was wide-eyed and ready to do whatever it took to win, but I just wanted to be myself out there, and I think that really helped me win. I was very "Wendell" out there and that showed in my edit. From that season, one key thing I learned was from a producer. I was sitting down in a confessional one time and we had just had a swap, which is when the tribes get mixed up, and this guy, Donathan, was on my tribe. He's this small guy, super country, and a white gay guy. I sat down with the producer in the confessional, and I'm like, Man, this guy Donathan is on my tribe and I don't know anything about him. He has this crazy country accent, and we couldn't be more different from one another, but I wanted to work with him and I'd love to be an ally with him. I just don't know if there's ice to break, and I don't know how to get through to him. The producer was like ‘Well, why don't you just go up and talk to him?’ So I went up to talk to him and we clicked like that. We ended up in an alliance that lasted the majority of the game.

From that, I took this fearlessness where I feel like I can talk to or interact with anyone or work with anyone, sometimes it's just a matter of you being willing to make that first call or open your mouth first and now I'm that kind of person. So, I will say one of the greatest things I learned from Ghost Island was that I shouldn't be afraid to say things first, or to volunteer things, or to make that first move regarding anything in life— great things come from making the first move. It’s a way of knocking down barriers, getting through to others.

Another entrepreneur interviewed through The Signal said that there's not a lot of transferable skills if you want to pursue entrepreneurship through formal education. What skills did you have to learn through your experience being an entrepreneur that a formal education could not have taught you?

Oh, that's a great question. I almost wish I would have got my JD/MBA when I was at Penn Law because I feel like I could have learned a lot more business-wise through business school. There are certainly things that I've started picking up or things that I have kind of had to pick up throughout my last few years as an entrepreneur. One of the more valuable things that I've learned in the more recent years is the power of delegation, and as an entrepreneur, especially when you're just getting started, you feel like there aren't enough hours in the day, and you're always working. If you can master how to delegate and how to put things into other people's hands, even if they're not as good as you, then you become way more efficient. So, learning how to delegate was very important to me. You don't always learn that in school. Sometimes you’d have group projects and stuff, but being the top person and then learning how to put things in other people's hands, or even how to hire people that are better than you at certain things to do those specific tasks, it really helps. I've also learned that it's very important to recharge your batteries sometimes and make sure you take breaks. Make sure you rest, make sure your mental health is taken care of, make sure those around you your loved ones are taken care of. You can't let this thing, this baby of yours that you created or that you are nurturing, you can't let that detract from other areas of your life.

You graduated Penn Law, went to Harriton High School and were raised in the Philly suburbs. How has being a Philadelphia native influenced your entrepreneurship journey?

I like that. Philly’s a blue-collar city and I consider myself like a real blue-collar kind of guy, and I have that hustler mentality, and I love that about Philly— it gives me some kind of a toughness mentally, physically and this ability to work long hours and work long days and lock in; that's why I haven't really left. I've left for undergrad, I've traveled a little bit, but I haven't really moved away despite certain opportunities, and that's because I love Philly. It's really me. Philly is me, and it's really shaped the person that I am.

At this point I saw you’re working on the show with HGTV and you have a growing platform, a huge following with a ton more to come. What’s coming up next for you and do you have any goals for the future?

I'm a goal-setter, I try to set these crazy-ish goals, like being on survivor was a crazy goal because so many people want to do it and so few people actually get on the show, and I was able to get on and win it. Then, from Survivor, even during and before Survivor because at that point I had been building furniture full-time as my job, my goal was to be on HGTV to have either my own show or to be a host on HGTV. I believe in the power of speaking things into existence and working towards goals, so I wasn't afraid of saying to the public that I want to be on HGTV.

About two months ago, a friend of mine Bryce Isaiah, who was on Survivor Season 26: Cagayan, invited me on his podcast and he asked me to manifest one thing. This was two months ago and I said Brice, I want to be a host on HGTV. This is something that I proclaimed on his platform literally on a random Tuesday. The next Sunday, I get a call from my agent saying, 'Hey, Wendell, an opportunity opened up in the ninth hour at the last minute for you for a hosting gig in New Jersey, New York and Connecticut. You'll be traveling and they need you up there this week like on Tuesday.'

I got a call on a Sunday and they wanted to meet up there for a Tuesday for a hosting gig on a an HGTV and this happened in one week. I literally proclaimed it and then on that next Tuesday, I found myself in an Uber with my bags packed on my way up to a home renovation show that I didn't know much about— my contract had hadn't even been signed yet— but I think it was because I put it out there. It was a goal of mine and I continued to work at it, and I stayed laser-focused on that goal. I'm just the kind of person that likes to set a goal and continue to work in that direction until I attain it.

At Penn, as you know, there’s a very prevalent pre-professional culture. However, especially amidst the COVID pandemic, students are realizing they want to pursue entrepreneurship or carve more meaningful paths fighting for causes they’re passionate about. However, there’s a leap from inspiration to creating a business, and a lot of people aren't really sure where to start. Do you have any advice for beginning entrepreneurs or Penn students who are looking to pivot into something they're more passionate about?

It’s important to keep the lights on and to keep your stomach full. From my law-clerking job I was able to keep the lights on, I was able to pay my bills while I worked on this project of mine building furniture, building my business and at a certain point, I was able to take a calculated risk take my “leap,” once this business had shown me that I can make money with it and once I had kind of my ducks in a row. I definitely encourage you to follow what's in your heart because to this day that's what I'm doing, and at the end of my long work days I feel invigorated. I feel motivated. It's a great feeling. But at the same time I just encourage people to make sure you're able to cover bases before making that “leap,” make sure you're able to take care of what you have to take care of while you build this business on the side.

I suggest this book called The E-Myth— it explains that just because you happen to be good at like baking pies or just because you're a great plumber or just because you're good at a certain trade, that doesn't mean that you'd be good at running a business doing that. So it's very important to understand the business side of what it is that you want to do. The E-myth kind of gives you steps on how to not just work in the business (in my case not just build furniture but how to work on your business so you handle other aspects of it), so if I can offer some advice, it’s to make sure that you're not just good at the thing that you want to do or the thing that you're selling, but you also understand what it's like to run a business and the various things that come with that–there's a lot more to it than just being good at it.

Editor's Note: Interview was condensed for clarity purposes.