Startup Spotlight #75: Season Three

Season Three is a contemporary apparel brand influenced by art culture and an outdoor ethos.

Jan 20, 2021

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I got the chance to speak with Adam Klein, co-founder of Season Three, about what he’s working on at his startup, and any advice he has for emerging entrepreneurs.

Traditional retailers are not keeping up with Millennial and Gen-Z values and wants, especially as the definition of work continues to change at warp speed. The feeling that one is not being represented by what exists in the world is present, and the overall frustration that comes from traditional shopping has left many consumers to settle for fast fashion, hype, and low quality.

Startup Spotlight: Season Three

Season Three cofounder Adam Klein.

Problem: Traditional retailers are not keeping up with Millennial and Gen-Z values and want, especially as the definition of work continues to change at warp speed. The feeling that one is not being represented by what exists in the world is present, and the overall frustration that comes from traditional shopping has left many consumers to settle for fast fashion, hype, and low quality.

Market: The U.S. imports over seven pairs of shoes for every person in the country, and annual sales now top $85.6 billion. However, footwear alone is not where our ambitions end. As we delve further into this world, we want to break into new verticals and create products that stand the test of time from a design and material standpoint.

Solution: Season Three is a DTC brand making heritage footwear for a new generation. We are driven by a deep passion for lasting, well-made products, and with enough time believe that we can build the next brand holding company. One that actually represents the people who buy into our community and products.

Team: I created Season Three with Jared Johnson, whom I met while we were pursuing our MBA at MIT. We have been helped/guided/advised by a countless number of wonderful people along the way, but I always like to give a special shout out to Ben Taylor, Archie Lee Coates, Jeffrey Franklin, and the entire Playlab team, Quinnton Harris, Eva Gildea, Hannah McNeill, Mackenzie Smith, Olivia Yao, and Anj Fayemi, for putting up with our insanity and being the best collaborators and friends anyone could ever hope for.

Recent Success:

Klein: We have all been through that one shitty job experience in our lives, and if we are fortunate it stops there at only the one experience. Shaped by my own shitty experience, I wanted to approach work at Season Three differently. While we get a tremendous amount done with our small team, we also have plenty of fun and keep it light. We do this by hiring for one trait above all others, which is the ability to handle conflict. Everyone has different points of view and almost all of them are valid, but what gets lost in translation now more than ever is the nuance that all issues brought forth.

We have been successful at vetting partners, contractors, employees, and interns and attracting talented individuals who have no problem speaking their mind, being proven wrong, and allowing the best idea to win out. This has created a great culture internally with our small team and of our extended ecosystem, which we deeply rely on. Because we have been so successful at the human element and capital allocation, we have been able to accomplish many things on a shoestring budget and stretch our initial capital raise much further than we thought possible, which turned out to be imperative once the pandemic hit.

Recent Struggle:

Klein: While Season Three has done a lot that we are immensely proud of, one area with plenty of room for improvement is raising capital. Our initial pre-seed raise happened after the boom of the 2010’s DTC frenzy when venture capital finally realized that brands take a longer time to grow than SAAS (software as a service) and traditionally don’t have as big of an upside. Then, we launched two weeks before the pandemic began, so it’s safe to say that our timing wasn’t great. I have such respect for founders who can sell, create tremendous enthusiasm, and close quickly, but it happens to be a different skill set than what I am naturally equipped with, but one I hope to get better at with time.

Founder Advice:

Klein: Don’t forget that even though you took a chance to create something special, many others will not fully understand how lonely and frustrating this journey can be at times. Remember what defines you is not success or failure, but that you had the will to follow through on your ideas. Through this process, you will find out much more about yourself and your interests than any normal job.

I have also been thinking a lot about how people no longer admit when they don’t know something, instead of simply asking for help. No one builds anything by themselves and it’s not a sign of weakness to ask for assistance. One could make a very compelling argument that it’s a sign of strength to surround yourself with excellent people. The only way to better yourselves and your company is to create an atmosphere where opinions are heard, ideas are debated, and the best one wins out regardless of who proposed it.

Three Cool Founders You Should Know About:

Klein: Here are three founders you should check out next!

Bruno Lucas, Founder of Zippi: Zippi is a fintech credit startup in Brazil.
Karina Akib, Founder of Well Nested: WellNested brings personalized postnatal care to new moms, both at their fingertips and in the home.
Eilon Shalev, Founder of elphi: elphi is a FinTech, SaaS company, streamlining the mortgage lifecycle from origination to securitization, leveraging cutting-edge technology to cut the mortgage origination process from 45 days to 15.

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