The idea behind the Chicago-based Trunk Club is appealing, simple, and very consumer-friendly. Say you’re a time-starved man with a hankering to dress better. Just sign up on Trunk Club, one of whose style experts will call or email you shortly after to talk about your vision for your wardrobe. A few days later, a bemused FedEx employee shows up at your door bearing a trademark "trunk" (made of cardboard), which contains 10 or so items of clothing. Keep what you like (and pay for it), send back what you don’t (and don't pay for it), and you’re on your way to a more stylish future.
That is, assuming you have cash to burn—to have kept all the clothes in my trunk would have cost me over $1,500.
FAST COMPANY: You’ve said that using Trunk Club will lead to guys having better sex. In what way "better"?
BRIAN SPALY: Probably what we meant was more sex. But in general, Trunk Club has among its central goals making a guy feel more confident, more comfortable in his own skin. We want to give that feeling you have when you walk out of your house in your favorite outfit, with some pep in your step, and that feeling of, "I look good today, I feel good today." In the context of actually having sex, it’s a familiar refrain from our customers: "I got the trunk, went through it with my wife, did a little fashion show, opened up a bottle of wine... I love Trunk Club." So I’m not sure if it’s better, but it’s hopefully more.
Speaking of sex, You named your first clothing company Bonobos. Isn’t the bonobo a kind of hypersexual, swinging monkey?
It’s not a monkey. It’s a chimpanzee, or great ape. It’s a promiscuous chimpanzee. I came across the bonobo when I was in my second year at Stanford Business School. I had this pants idea, and hadn’t picked a brand identity for the product yet. The bonobo loves to have sex, is very peaceful, and unlike many apes, never fights. They use sex to defuse tension. That just makes a lot of sense to me. A lot of people at first were like, "I don’t know how to say that. What is that." Now they say, "What a great name!"
It seems like Bonobos caters more to the stylish guy, Trunk Club more to the novice?
To the naked eye, that might seem like a fair generalization. But Trunk Club actually caters to guys across the style aptitude continuum. Three things drive someone to use Trunk Club: you don’t have time to shop, you don’t have access to shopping, or you don’t have the desire or inclination.
My own experience sampling Trunk Club this week was mixed. My style expert, Lindsey, was very attentive, but many of the shirts didn’t fit quite right. That’s mostly because I’m a weird size. I’m shaped more like a different kind of ape, an orangutan.
It’s not uncommon to hear this, and certainly we’re much more proud of guys who say, "Oh my gosh, I’m keeping everything!" But what differentiates us is that if you had that experience shopping online, and nothing fit, it’s really frustrating. If you use Trunk Club, we’re the ones that did all that work. We’re gonna get feedback, and it’s a process of getting to know each other. No one at Nordstrom.com is seeing what you’re sending back and saying, "We can do better on the next iteration." We find that each trunk has a higher keep rate.
It also was out of my price range.
Our service is not inexpensive, it’s not a discount service. But the most expensive shirt in your closet is the one you don’t wear.
You’ve likened Trunk Club to, of all things, wealth management services.
I like to say it’s wardrobes under management instead of assets. It’s the same concept: If we do a great job, they’ll give us more assets to manage; if we do a wonderful job, they’ll tell their friends. We’re somewhere in between Charles Schwab and Goldman Sachs. Guys in the $75K-plus income range are eligible to feel like they can afford the service.
How many style advisors do you have? Do they all have retail experience?
We have between 40 and 50 now, and 90% are women. They tend to have a background that includes sales, but rarely retail. One in three of my friends who are girls could do the styling part of the job, but only one in a hundred could do the sales piece. Finding someone who knows style is less important than finding someone who understands sales and relationship management.
I read your style experts may even friend customers on Facebook to check out their style?
We use myriad tools to get to know you better. If in our introductory conversation, the style expert decides it would be helpful, she may say, "Hey, is it cool if I friend you on Facebook to see what you do, and what you like?" It’s a powerful tool to help us get the right clothes your way.
You’ve reached some milestones—your first million-dollar month in revenue, your 10,000th customer—but are you profitable?
Not even close. But I would say our profitability aspirations mimic those of a venture-backed startup. We’re investing a lot in the future. We have 10 full-time software developers who are building features that will help us cater to 100,000 guys, not 10,000. We’re not burning a ton of cash. I’d say we have two to three years of cash in the bank.
Back when you were in private equity, you used to come home and sew pants. Do you still have that habit?
No. The wonderful thing about Bonobos and Trunk Club is that I now find my day-to-day responsibilities bring so many opportunities to innovate and create. That was largely missing from my days as a management consultant and investor. I was looking to satisfy an urge to make stuff, build stuff—and that’s what I do at work every day. Now, actually, sometimes I come home and make investments on the Internet in my spare time. The tables have turned, in a very positive way.
This interview has been condensed and edited.
Follow Fast Company on Twitter.