At just under 5 years, my time at Trunk Club has been one of the longest and most formative experiences of my career thus far. The people, challenges and industry taught me a lot about how to build, how to act and how to thrive in a space that I had never been a part of before.

What was done so incredibly well by everyone at Trunk Club, was that our entire team was on the same page and believed in the one mission put in front of us. So, I thought it would be fun to share some of my favorite quotes and what I learned from some of the leadership that I very much respected and looked up to.

Act like an owner.

— Trunk Club: Brian Spaly
 // Original: Unattributable

Everyone who has been inside the Trunk Club walls has likely heard this said to them at one point in time. At this point in time, everyone has their own interpretation of what this means to them but to me it meant caring enough about EVERY SINGLE THING so that we could always put our best foot forward as a team. This meant that if you saw something, you said something. This infused itself into everything we did at Trunk Club… From wiping down the bar on the 7th floor and serving our customers drinks, to showing up to count inventory at the warehouses, to speaking up when you believed we were making the wrong decision. We all cared enough to speak up and make sure we were always putting out best foot forward.

Now, we DEFINITELY disagreed and had to talk through every idea proposed… But it was all clearly from a place of passion and excitement to do the best we can. Because of this, we always figured out a path forward together.

Everyone has a plan, until they get punched in the mouth.
— Trunk Club: Mike Cruz // Original: Mike Tyson

We’ve all likely heard some version of this in life. “The best-laid plans of mice and men often go awry.” And oh boy, did they go awry and did we get punched in the mouth… As a part of the technology team we constantly broke things and put them back together. We were frustrated every time we took a step forward, and two steps back. But, we were always excited to pick ourselves back up, dust ourselves off and move forward. Our team always favored progress, innovation and excitement over all else. That very much took its toll on the organization at that moment, but the amazing work that it produced alongside it was well worth anything else at the time. It was invaluable to hear that you can plan as much as you want, you can prep for days/weeks/months and things will STILL fail… But that it was okay to do so if we learned, picked ourselves back up and tried again. We won together, we lost together, and along the way we figured some shit out together.

As a leader, you are either an example or a justification.
— Trunk Club: Michael Barkin // Original: Unattributable

Someone is always watching. You have no idea who looks up to you, draws inspiration from you or looks to you for an example. So be one. Michael once said that to me, following the quote above, and it has always stuck with me. At Trunk Club (and in life) someone is likely watching what you do, and you have the opportunity to be an example or a justification each step of the way. As a leader, if you pick up a piece of trash and throw it away or clean out the sink (you know who you are), people will see that as an example of how to act and behave. You can make small but powerful choices that elevate everyone around you. As a leader, you could also leave that piece of trash or exclaim, “It’s not MY job to clean this sink”, and people will see that as a justification that they do not have to do that as well. How you choose to make each of these decisions has a small cascading effect on everything around you, you might not even realize it. So I always tried to make it the right choice.

People will forget what you said… what you did, but people will never forget how you made them feel.
— Trunk Club: Zuzana Kajuch // Original: Maya Angelou

This applies to SO MANY different aspects of Trunk Club. From how we develop relationships with our members to how we treat each other as employees each and every day. Trunk Club (and I imagine most organizations) was built on both of these relationships. We had always touted that selling something to a member was easy if you had a relationship with them and they trusted you. We always talked about the first time a member put on a custom suit and they stood a little taller and shined a little brighter. These were all moments in which we made our members FEEL great about Trunk Club.

When it came to our interactions day to day, the teammates that made us feel inspired, needed, successful and useful were the teammates that ALWAYS had the help they needed. It was a GOSH DARN compliment fest from the moment you walked in the Trunk Club doors because we were just so excited to tell each other how much we enjoyed working together. I always tried to build the relationships with the people around me first, then we could figure out the best way to work together now that a little trust had been established.


I wrote this all down with a few goals in mind:

  1. Give myself a moment to reflect on the things I have experienced, learned and all that I'm thankful for.
  2. Remind myself never to forget these lessons going forward.
  3. To help remind/ignite the same learnings and feelings in anyone that is interested in doing so, old Trunk Club and new.

There are FAR too many people I would like to thank, so I will do that in person and show you how much you all matter to me. If you got this far, I am incredibly impressed and humbled, so thank you. Say the word 'flibbertigibbet' to me and I owe you a coffee!

Please stay in touch, I will continue to need your help and support, and I hope to return that favor any which way I can. I love Trunk Club and all of you very much. Looking back on it, I would say 'Mission Accomplished', and I have someone here to help me share the sentiment.

IG: @drishay

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