JackThreads Founder & CEO Jason Ross Reflects on Bootstrapping, Company Growth and Street Style

JackThreads Founder & CEO Jason Ross

JackThreads Founder & CEO Jason Ross

Jason Ross, Founder and CEO, launched JackThreads in 2008. Since then, he has built a members-only men’s apparel brand that continues to perform in a competitive retail environment. Curating and showcasing street, skate, surf and contemporary fashion brands at exclusive prices, JackThreads is now a Thrillist Company that offers the best from classic labels as well as up-and-coming designers. Jason has been a FoundersCard Member since 2011.

1. What was the “aha” moment that spawned JackThreads?

I’ve always been really into fashion and finding great deals, but I think the aha moment came a couple years after I graduated from college. The private shopping club model was taking off in Europe and I thought it was such a great way to make brands more accessible and affordable. I set out to do the same, but with a focus on guys like myself, looking for better streetwear and contemporary merchandise in the U.S.

2. You worked on JackThreads for two and a half years before hiring a second employee. How were you able to single-handedly remain so focused on your vision, and what was the hardest part about getting JackThreads off the ground?

It was definitely difficult those first few years finding the time and resources to really build this thing. I spent a lot of time working odd jobs and bartending at night to make sure I could work on the business during the day. I also maxed out a few credit cards (which I don’t necessarily recommend) and called in a lot of favors. The first version of the site was actually built with the help of a former professor at Ohio State University, who assigned the coding to his students as a class project. 

3. What is the best piece of advice that you received when launching JackThreads?

I know it seems sort of obvious but I feel like for many entrepreneurs it’s not always the case — it’s so important to create something you’re truly passionate about. When I began my career, I launched a sports marketing company with a friend. We had some moderate success, but I just didn’t have a strong enough interest in what we were doing. It made it really hard to want to dig deep and put in the effort we would’ve needed to make the company truly successful. Basically, don’t just start a business to start a business – make sure it’s something you love and believe in. 

4. Based on your experience at JackThreads, what are some of the key ways that you were able to drive new member acquisition?

I think the main reason we’ve been able to drive guys to the site, is that we deliver a very niche and curated product and work hard to make sure we’re bringing the most relevant product and brands to our audience. Beyond that, we’ve had a lot of success come through our referral program, which offers guys $10 every time they get a friend to sign up for our site and make a purchase using their referral link.

5. Some companies thrive on mobile apps, while others tend to put theirs on the back burner. What role has the JackThreads app played in the company’s growth?

Mobile has played a huge role in our growth. Over this last year especially, we’re seeing a significant amount of our revenue (over 40 percent!) coming through mobile and have had close to two million app downloads. Plus, we’ve held a top ten spot in iTunes’ Top Free Apps list for over a month now.  It’s definitely been a game changer for us.


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

It really varies depending on the tradeshow seasons and production of our private labels, but on average I probably travel eight to ten weeks out of the year. 

7. What is the hardest part about your job?

The hardest part about being an entrepreneur is that at the end of the day the successes and failures of your business are on your shoulders. Even though I have an unbelievable team behind me, this is my baby and my dream, so it’s hard to take time away or take a day to myself without worrying or thinking about something I should be working on.

8. How would you define your personal fashion style, and how has it influenced the brand?

My personal style has definitely been influenced by comfort and my hobbies growing up like snowboarding and skateboarding, and you see a lot of that style in the brands we choose to sell on the site like Vans and Goodale.

9. What is the #1 fashion fail that you’ve seen recently?

One word: jeggings

10. What sort of side projects are you working on now?
We’re definitely going to have some exciting news with our private labels coming up and our recent international launch, but nothing I can talk about yet. Stay tuned!
11. JackThreads caters to young, stylish, street-wise males. What sort of activities outside of work keep you young, stylish and fit?

Since my work life is so hectic, I try to exercise as much as I can in my off-time by getting outside and running or snowboarding. Outside of that, I spend a lot of time exploring New York (since I only moved here a few months ago), which is always an awesome opportunity to check out the great street style in this city.


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