“Find amazing co-founders. I have the best co-founders in the world. They’re my best friends. We love problem solving, we love working and putting our minds together. Make sure you find your dream team. And then go find a problem you want to tackle together.” – Skyler Logsdon

Found-er (noun): a person who establishes an institution or settlement. 

Behind every company is the story of a founder or team of founders who came together with a vision and persevered to bring an idea to life. Every founder story has its wins, but it also has its challenges. At the heart of every founding story, one theme is common: resiliency. How do you make the hard decisions? What motivates you to keep going when things get tough? 

We sat down with Skyler Logsdon, Co-Founder of Boomerang, to share his c0-founding story and hear about how they’ve turned some of their greatest challenges into important learnings for the company. 

A Simple Problem Yet to Be Solved (Backstory)

It’s been said that some of the greatest ideas come while you’re traveling. For the team at Boomerang, this is how their story began. While Augustine Dipe-tran, Philip Inghelbrecht, and Skyler Logsdon were traveling in Mexico, Philip shared a big idea with Augustine and Skyler, that he realized had yet to be solved – lost & found. For anyone who has taken a plane, train, or automobile while traveling, you or someone you know has been the unlucky participant in losing something they’ve wanted to recover. For the lucky, you’re able to get your item back, but for many, that same fate doesn’t always happen. 

As Logsdon and his co-founders sat around the table post-Mexico, they decided the Lost & Found problem was worth solving. In the United States alone, Americans spend $2.3B per year rebuying lost items, many of which are lost at businesses. So, to help those in need, Boomerang was born and launched in May 2022. Boomerang allows businesses to find lost items (and catalog them) and through the Boomerang portal, owners can retrieve their items thanks to the help of AI. 

The Early Days of Boomerang

UC: What were some of the early wins you and your team saw that gave motivation to keep building Boomerang? 

Skyler: Our team is 12 people (as of this interview) and our seed round went well ($2.8M seed round). We finished fundraising extremely fast which was a great signal. Everyone knows it’s such an annoying problem to lose items; they’ve all been there. Investors have been instrumental in our early wins with customer intros to hotels, airlines, and other businesses. Also, the sheer amount of businesses who respond to us keeps us going. We’ve had airline companies, sports teams, universities, and more asking us to finish building the product when it was in its early stage because they all wanted to use it. WeWork was one of the earliest partners along with the Cleveland Browns (First Energy Stadium) and UC Berkeley. 

UC: What have been some of the hardest challenges that have turned into the greatest lessons in your entrepreneurial journey?

Skyler: Selling into the travel industry – think airlines, ride shares, cruises, hotels – was touch and go in 2022; COVID hit us hard and we didn’t know what would happen in the world like everyone else. The travel industry in itself has many inherent problems which can make things unpredictable for us: oil prices, labor shortages, all of it affects our customers. We had to learn to prioritize and tackle things we knew we could get through. 

Trying to disrupt a space that has constant meltdowns is a constant challenge, but we continually learn how to be patient. You can’t be all gas. If the greater industry you chose to work in is going through something really big, you need to hang around and get through it. Don’t be tone deaf with clients; have empathy for what they’re experiencing. Stay kind, circle back. We tell many of our clients, once they come out the other side, we’re here to pick up the conversation. Rome wasn’t built overnight, and we’re doing the same with our company. 

Another lesson we’ve learned is patience and selectiveness in hiring. Big tech was overpaying talent, and seed-stage startups just couldn’t compete with the offers. In those times, as a founder, we had to really focus on the right hires for us. The kind of talent that love building startups from the ground up and wouldn’t ever want to be at a big company, even if the pay is greater.

A Growth Trajectory

UC: When and where did scale come into play? 

Skyler: We had strong product-market fit early on and phenomenal case studies in various categories. From the beginning, we’ve built ourselves to be set up for scale and are ready to go. We could sign 10 airports tomorrow for example. We’re not leaving anytime soon. 

UC: How do you look at the next 5 years? 

Skyler: Airtags are a top seller on Amazon. Individuals have transparency on where their items are at which is creating massive winds in our sails. Businesses can’t sit on lost items for a long time and customers are creating a big shift in this for businesses. We’re past the days of business and venue owners throwing lost items in a box; customers are expecting more and Boomerang will be here to power the comms and shipping behind all of it. Take Japan for example, their match back rates are phenomenal. In 5 years from today, all lost items will be powered by a smart L+F platform – it will be an expectation and we’re here to build that foundation. Found an item? Want to get it back to its owner? Boomerang solves that. 

Thoughts on the Future

UC: The work world is changing – how are you leading the charge to meet those changes with how your team works? 

Skyler: Boomerang HQ is in Miami and we’re a fully remote team. We’d love to get an office one day and bring our great talent together regularly. The more time you can spend with your team not only in problem solving mode, but the more you can be off script and get to know each other, that’s where the personality comes through. You need to find ways to get to know each other. 

For us, we do happy hours once a week. Team story time where everyone chooses a topic and shares stories. We know the importance of setting up the space to allow our team to talk with each other outside of work. Bi-Quarterly bonanzas where we bring the whole team together and spend a week with each other off site somewhere. Continuing to think of creative ways to get to know people. The more you know your colleague, the more empathy you have. Don’t leave any of your teammates with the bag.

Words of Wisdom

UC: Any other words of wisdom or advice you’d like to share with those embarking on founding journeys of their own? 

Rome was not built overnight. First-time founders may not expect how hard it actually is. You have to have thick skin. You have to be able to shake off your losses. You hear mostly no’s, but be resilient. You will learn. All you need is a few yes’s. If you come into being a founder assuming a rocketship emoji, you’re in for a rude awakening. Having experience in hardships and adversity is key. Being a founder is hard. You’re underpaid, you don’t sleep much, you make a lot of sacrifices – a lot of personal sacrifices. This isn’t a career you choose for lifestyle or salary, you do it because it’s hard and it’s going to take blood sweat and tears. 

There will be more hard days than great days. When the great days come, enjoy them and celebrate them and get ready for the next hard day. You get addicted to the thrill of the yesses. Early on, no one cares about you. The world doesn’t know your company’s name. Your cold emails go to spam. Your calls don’t get returned. It’s a total game of resilience. Take care of your mental health. Take care of your physical health. Keep showing up every day, compounding days of resilient effort. Eventually, things swing in your favor, and you get a lucky break that can change your business. When you get those lucky breaks, lean in and enjoy that shift in momentum and parlay it. You earned it. Carpe diem. 

Find amazing co-founders. I have the best co-founders in the world. They’re my best friends. We love problem solving, we love working and putting our minds together. Make sure you find your dream team. And then go find a problem you want to tackle together. Be grateful for co-founders everyday and don’t discount how important they are to you and your relationships with each other.