Trunk Club CEO Brian Spaly Discusses Trunk Club and the Chicago Startup Scene

Brian Spaly, CEO, Trunk Club

Brian Spaly, CEO, Trunk Club

Brian Spaly defines the crossroads of business and men’s fashion. As Trunk Club‘s CEO, his mission is to ensure that members are always the best dressed man in the room. Trunk Club delivers hand-picked clothing right to your doorstep, taking the hassle out of shopping. Based out of their River North (Chicago) office, Brian oversees a team of 100+ stylists. Prior to Trunk Club, Brian co-founded Bonobos, and attended Stanford’s GSB. He has been a FoundersCard Member since 2012.

1. You were approached to become Trunk Club’s CEO and founder. What did you love about the concept of Trunk Club at the time, and how has that idea evolved into what the company is today?

Trunk Club was the first to offer the stylist-member model, and I think it’s an awesome one. I love that we solve problems for guys and make it easy for them to get new clothes. Over time we’ve gotten a lot smarter about how to execute, improving our product assortment, our stylist team and our operations. Things run smoothly now but it’s been a long hard slog uphill to get there.

2. What were some of the greatest challenges that you encountered when building Trunk Club?

Hiring the first 10 sales people was tricky – we weren’t exactly sure what we were looking for and they weren’t sure what they were signing up for. Another challenge was getting the word out to sign up the first 1000 members – we’re still not well known and working hard to spread our name across the country. We’d rather invest in providing a great service than in great marketing without substance, so we’re just moving a bit more slowly than some of our e-commerce brethren.

3. What is the best piece of advice that you received when starting either Trunk Club or Bonobos?

Fail fast and cheaply. The idea is that you want to figure out as quickly as possible if you have a product/market fit versus investing a ton of time and money in building something before you know if the customers actually want in. In fact, I took a class called Product/Market Fit at Stanford GSB in my 2nd year MBA program and enjoyed it a ton. Credit to Andy Rachleff and Bill Barnett for creating such an impactful class for aspiring entrepreneurs.

4. How has Trunk Club been able to effectively utilize social media to help increase exposure and its customer base?

Pretty simple here – just be present, proactive and reactive. We’re not the cutting edge social media company or anything, just aware of the medium and finding ways to show up and drive interest with our constituents.

5. Do you view yourself as more fashion or business minded?

I’d like to think I fall somewhere in between product and business. I’m obsessed with our brand and our physical space and our culture, but I’m also aware of the exigencies of being a venture-backed startup with limited resources. We are scrappy and clever when it comes to building things. I don’t ever use the word “fashion” at Trunk Club; we’re not a fashion company, we are a technology-powered apparel service.

6. What is the startup scene like in Chicago, and which companies from the Windy City should we be on the lookout for?

Chicago is picking up steam, but there are some key ingredients we are lacking and one of them is simply quantity and quality of startups across all life stages. I remain cautiously optimistic that we’re moving in the right direction and volume is increasing. I’m a huge fan of Braintree and GrubHub, but you already know those businesses well. On the up-and-coming end of the spectrum I’d say ShiftGig (I’m on the board, so is Sam Yagan) has a great founding team and getting better traction in a huge space. Protein Bar has the potential to be a $1B public company, and Future Simple is another company that is compelling and likely to emerge a winner.

7. What is the hardest part about your job on a day-to-day basis?

Figuring out what to prioritize. Having to say no to a lot of ideas that are great and interesting but would diffuse our efforts in too many directions. Managing a sales team of 100+ stylists is also a tall order.

8. How many days a month (or year) do you spend traveling?

I’m on the road 5-10 days out of each month. San Francisco/Stanford about once a month and then Vegas, L.A., and NYC for meetings, investors, trade shows, etc.

9. What is the #1 fashion fail that you refuse to allow Trunk Club members to be a part of?

Looking like they are trying too hard. We emphasize the importance of finding clothes that work well for you and flatter your figure, but we strive to ensure that our members (often in their 30s, 40s and 50s) don’t look like those joker tourists that buy Abercrombie and Fitch even though they are 30 lbs overweight and 30 years older than the target customer for that brand.

10. What percentage of males would you say are in desperate need of a new wardrobe?

Tough to say, perhaps 20-30%. Most of our members actually know what they look good in and have solid fashion sense. They just don’t know how to shop successfully, waste a lot of time and money on gear that they never wear, and just don’t enjoy the process of shopping. Trunk Club is not all about helping guys that are clueless. It’s much more about convenience, high quality service, and saving time. Many of our best members are super stylish guys that are just over going to the mall or Michigan Avenue to deal with the awful experience of shopping at a place like J.Crew or Barneys.

11. Can you ever imagine expanding into a female version of Trunk Club?

Yes. We talk about it all the time. We’re a little schizo on this, but today I woke up on the no one ever failed by focusing too much side of the bed, so I’d say it’s not coming any time soon. There are a few competitors in that space but none that have been well-funded and anywhere near our scale.

12. What is one startup that FoundersCard members should keep an eye on?

You know I’m a huge fan of Houzz and Waze (editor’s note: interview conducted prior to Google’s acquisition of Waze). Maybe it’s the Zs in their names, but both are super cool companies that I find myself using almost daily now. I love Houzz because I’m in the middle of a home renovation, and it’s such a compelling app and way to interface with my contractors on design-related issues. I love Waze because it helps the average guy outsmart traffic cops. Is there anything worse than a traffic cop in a speed trap town?

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