We were lucky to catch up with Ali Gilbertson recently and have shared our conversation below.

Hi Ali, thanks for joining us today. Let’s start with the story of your mission. What should we know?

The mission of my secondhand shop “Happy Hours” is to create a welcoming & easy-going environment where customers can find (or just enjoy perusing) special treasures that have otherwise been outgrown, discarded or forgotten. Whether it’s clothing, art, or a weird little knick-knack that makes you laugh, I believe that STUFF can play such an important part in our lives and our memories, made even better if this stuff has history and a story! There’s so much out there. Happy Hours is filled with used things that caught my eye or spoke to me one way or another. I collect my wares by driving cross country— stopping at random little thrift shops coast to coast, going HAM at an estate sale, helping someone downsize before a move or after losing a loved one, or digging through trunks of my dad’s clothes from the 70s/80s in the folks’ attic. I find so much joy in finding and respecting these items, dusting them off, merchandising them in a way that gives them fresh desirability, and then watching as someone new picks it out, gets excited and decides to take it home to live a new life. For me, this is such a sweet reward!

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

Happy Hours is something I’ve created that’s all my own. It’s a secondhand shop with clothing and home decor, but it’s also a source of support for the community, a place to take Mom while she’s in town, and/or meet a friend and have a laugh.
I’ve always had a passion and eye for design. Thrifting was a way of life from infancy that became a career in my 20s. I grew up in a family bar and those jukes and vibes have always been strong in me. My goal (and what inspired the “Happy Hours” name) has been to create that same comfortable & good-time atmosphere your favorite pub provides but like, there are sweaters & art for sale and I get to go to bed early.

I devote myself to this (otherwise discarded) STUFF and the environment I’ve created to bring it to my customers. Getting to admire & thoughtfully showcase these special treasures while they’re mine… well it might just be my favorite thing. Possessions, whether they’re old or new, have a story and a vibe and I want to see that live on! Resale to me isn’t about finding something ‘for cheap’ and ‘flipping it’ to squeeze out a profit… it’s about stretching out the story.

I come from a family of artists & whack-os. Wisconsin bred. I went to school for acting, moved to NYC and promptly gave up theatre FoR ThRiFt. I found Cure Thrift Shop in the east village and spent 9 incredible years in Manhattan as their Creative Director. I absolutely loved NY, until I didn’t. I moved back to WI, traveled a bit, bartended a bunch of weddings, found my way to Madison, Wisconsin’s capital, did interior design for awhile and then a global pandemic wound up giving me the space and motivation (unemployment) to reach outside the box.

My business model is unconventional. My shop is a little, secret shopping spree hole-in-the-wall inside an old residential home built in 1897, since made commercial. My social media is run solely by myself with the goal of being authentically me and making my presence personal (while still being entertaining). I sell stickers of my dog, Redford, who is my sweet boy, number one friendliest greeter, and my ONLY employee now & forever. I limit my scheduled shop hours to only 2 days a week. I want to be free to travel and enjoy my hobbies, but I find most importantly, I want to enjoy my job! I accomplish this by keeping a schedule and prioritizing work that I have come to find works best for ME.

Any fun sales or marketing stories?

This summer I had a non-profit sale in my driveway at home that benefitted the National Alliance on Mental Illness. The gimmick was that after somewhat recently being diagnosed with ADHD and working with a specialized councilor, I was attempting to rid my garage and storage of ADHD-brain clutter, unfinished projects and once “wise ideas.” I was very open and shared my mental health experience/journey with the community and that I have learned so much about myself in the process of this diagnosis and self-work. I really wasn’t sure anyone would care, but I thought that donating the profits to NAMI was a win-win, more attractive way of saying, ‘Here— come buy some sh*t I don’t think is good enough to take to my shop.’

The sale wound up being a great success! :) People cared. A lot! Local businesses made donations of food & drink to be served or raffled off. I was contacted by many people wanting to drop off sellable contributions to the sale, and so many people came to shop generously! The event wound up bringing in $2500 and it’s something I hope to make an annual shindig.

As I wasn’t sure what to expect, I did the whole thing on my own. The community’s enthusiasm rapidly snow-balled in the last day or two before the sale and by the time it became too big for just me, it was sort of too late. Next time I know to have help. Haha! But the event became overwhelming and taxing for all very positive reasons.

The most rewarding part for me personally, were the number of people who privately reached out to me to tell their own mental health story, ask for resources, or say thank you for sharing my experience and/or choosing to benefit those with mental illness. This was unexpected and intensely moving. I feel so incredibly honored to have been able to give inspiration and motivation. To have spun the self-work of my own difficulties into helping others struggling was more full-circle and fulfilling than I ever anticipated.

This experience has motivated me to be more generous and collaborative in my business. Truly— the more we reach out to others, the more we receive.

What do you think helped you build your reputation within your market?

I think that my reputation has benefitted most by striving to always present my authentic self to my customers and online followers. I have gotten such a positive response from approaching my business honestly, unapologetically, and with mega confidence and trust in my eye, years of experience, and natural ability.

Contact Info:

• Website: shophappyhours.com
• Instagram: @happyhoursmadison
• Facebook: Happy Hours Madison

Image Credits
Ali Gilbertson