Journalist Tim Struby spent 20 years traveling the world, penning stories for the likes of ESPN the Magazine, The New Yorker, and Outside magazine. When COVID lockdown hit, Struby found himself with the time to finally fix up his place. The only problem? He really didn’t know anything about interior design, and the last thing he wanted to do was spend hours looking at couch options.
It was a pain point that he realized many people shared, which led to his lightbulb moment and the founding toTree, which bills itself as “the company you think about when you don’t want to think about furniture shopping.”
“Compared to writing, the life of a CEO and founder couldn’t be more different,” Struby told Entrepreneur. “The biggest challenge hasn’t been the work, but rewiring my brain. I spent most of the past two decades at a far slower pace thinking, researching, talking, and listening to people. Today? It often feels like a blur, going 100 mph — managing people, managing budgets, holding meetings, and wearing more hats than I’d ever imagined possible. Every day is an adventure.”
Read on to learn more about Struby’s journey from journalist to founder and to get his best advice for first-time entrepreneurs.
Please give us the elevator pitch of your business.
For millions of people, myself included, furniture shopping sucks. Too many brands, too many options, little to no guidance, and it’s generally an exhausting/frustrating waste of time, energy, and money. toTree is revolutionizing the furniture shopping experience by solving those problems. Our secret? We’re the first-ever furniture shopping service, combining just the right amount of interior design expertise with a remarkably fast and easy online process.
What inspired you to create it?
During the COVID lockdown, I was dating someone who had a great eye for interior design. I asked her to help me fix up my living room, which I’d been putting off for years. As we discussed the project, I realized that I knew so many people in the same boat. Especially guys. I literally declared, “I think this has potential for a great business.”
What advice would you give entrepreneurs looking for funding?
The traditional VC route isn’t for everyone, so get creative and unconventional. When I was looking to do a friends and family raise, I turned to a poker player I’d written about 10 years ago for ESPN the Magazine. That conversation led to eight of the world’s best poker players investing in toTree.
Please share a breakthrough moment that let you know you were on the right path.
Last year, we were really struggling to get users through the entire survey process, where people provide information about their needs, tastes and budget preferences. After months of testing and research, and then another few months of implementing changes, we’re now seeing a 900% increase in survey completions. Survey completions lead to conversions.
What does the word “entrepreneur” mean to you?
Ferocity of spirit. A spirit that includes passion, curiosity, determination, drive, imagination, fearlessness, and self-determination.
What is something many aspiring business owners think they need that they really don’t?
Deep knowledge of the space they’re looking to disrupt. Specifically, a deep knowledge before starting out. Take furniture, for example. You don’t need to have been a furniture expert with years of work experience to solve a significant problem in the space. In fact, I think it can be a liability because of the subconscious biases and prejudices that develop over time. To disrupt an industry, you often need an open mind, a tabula rasa. Only then can you step back and see that there might be a better way of doing things that no one else has seen.
Is there a particular quote or saying that you use as personal motivation?
I have two. “Be bold and mighty forces will come to your aid,” and “That which does not kill you makes you stronger.” The first gets me out of bed every morning, excited to change the world. The second helps me sleep at night!
Journalist Tim Struby spent 20 years traveling the world, penning stories for the likes of ESPN the Magazine, The New Yorker, and Outside magazine. When COVID lockdown hit, Struby found himself with the time to finally fix up his place. The only problem? He really didn’t know anything about interior design, and the last thing he wanted to do was spend hours looking at couch options.
It was a pain point that he realized many people shared, which led to his lightbulb moment and the founding toTree, which bills itself as “the company you think about when you don’t want to think about furniture shopping.”
“Compared to writing, the life of a CEO and founder couldn’t be more different,” Struby told Entrepreneur. “The biggest challenge hasn’t been the work, but rewiring my brain. I spent most of the past two decades at a far slower pace thinking, researching, talking, and listening to people. Today? It often feels like a blur, going 100 mph — managing people, managing budgets, holding meetings, and wearing more hats than I’d ever imagined possible. Every day is an adventure.”
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