Seasons

In June of 2019, I left Nike to build a members-only subscription service for fashion called Seasons. I took the idea from sketch to prototype and raised a $1.65M pre-seed from Initialized Capital, Notation Capital, BoxGroup, WndrCo, and several others. Three months after closing, we launched the first version of the service and it was very rough. Branded hangers cost a fortune and took forever to make so we ended up shipping out Stone Island jackets on plastic white hangers from Amazon. Still! We were signing up customers.

A few weeks post-launch, we were fortunate enough to raise a $2.75M Seed round from Kindred Ventures and other insiders. We had proved out the model and were growing pretty quickly into the holidays. Two months later, the world shutdown and we saw membership nose dive. Instead of pivoting, we doubled down and focused wholesale partnerships. When boutiques stopped buying during COVID, we swept in, took over their buys, and made these exclusive brands available to rent for the first time.

When things opened up again in the fall of 2021, we were ready. Memberships picked up, we kept shipping product updates, and reached over 1000 active members. These milestones came with some hurdles. Logistics, inventory management, customer service, warehousing, merchandising, and too many other things to mention. We had to navigate all of it.

Going into the Spring Summer '22 buying season, I realized we needed more money. Regardless of the time we lost during lockdown, COVID was no longer an excuse. We regrouped, put together a plan, and attempted to raise a Series A, twice. After the first try, we got an extension from our existing investors and bought ourselves 6 months of runway to improve our numbers. With $122K MRR, 1250 members, a healthy waitlist, and dozens of exclusive brand partners, our second attempt failed.

In hindsight, I realize how difficult the business would've been to scale. Inventory to service membership was getting exponentially more expensive and we just didn't have enough time to prove out the sales portion of the platform. At the same time, our closest comp, Rent the Runway was down 78% from IPO a few months earlier. Throw in Omicron, increased shipping costs, and inventory depreciation, it didn't make sense at scale. We had to call it.

Regardless of how it ended, it was one of the best experiences of my life and I'd do it all over again in a heartbeat.