Jess Pittman has crafted the perfect blend of vintage goods and meaningful client care with Flipside Estates and Consignment Concierge. Estate sales are a perfect way to find quality, eclectic items and furniture at a great price. But more importantly, the items sold in her estate sales capture a life well celebrated. PATTERN had the opportunity to sit down and connect with Jess about the ins and outs of her business.
Emily Coy: Tell me a bit about yourself.
Jess Pittman: My name is Jess Pittman and I am the owner of Flipside Estates. I started this business almost exactly four years ago. I was working at another company that provided high-end online auctions and I noticed that people needed the service side of auctions. I wanted to incorporate more services like donation and trash removal. There is more involved than just the liquidation of property. In order to liquidate, Flipside Estates typically hosts estate sales, online auctions, and consignments.
EC: What sparked your passion for helping others with their estate needs?
JP: Everybody needs a hand. I think it is an overwhelming experience when people are grieving a family loss. It’s a stressful situation, even when people are simply downsizing and going through different stages of life. We provide a service that can be completely hands-off—our clients trust us to come in and get the job done for them. I am passionate about the people we work with and providing the most perfect customer service possible. That service gives the opportunity to trust in the system. We are taking care of people’s belongings that they have collected their entire lives, so we always want to take care of their items the same way they did.
EC: Cleaning out a home and personal belongings can be an intimate and emotional task for your clients. How do you create a positive and meaningful experience for them?
JP: It is great to be able to explain to people that their belongings are going to have a second life. They’re not just going to be dropped off at your local donation bin and ignored on the shelves. It is really cool to see somebody come into an estate sale and demonstrate, “I want this item and want to give it new life.” We are at the point of being able to get this new generation to shop estate sales and buy items that come straight from the source—straight from the family. You are supporting a locally owned business, a local family. It is really important to me that our clients are taken care of and feel comfortable with the process. They know that their things are cherished and appreciated, as well as their home.
EC: How does Flipside Estate stand out within the Indianapolis community?
JP: I think being a woman-owned business makes us stand out. The online auction and estate sale field is mostly male-dominated. We bring a creative touch to what we do and have a sensitive approach. There is a lot of trust that goes into this line of business and we want to make customers and clients happy with their experience. We have creative events with our consignment program like Sip and Sales and other themed events. We even had a DJ at our last event. Creating an inviting environment is really important to us.
We also have just partnered with an organization called Coburn Place that helps support victims of domestic abuse. They house about 150 clients at a time and they set up these apartments with everything from a sofa to Tupperware. We are trying to find ways to donate specific items straight to the source and support people who really need it.
EC: What was the most memorable estate sale you have hosted?
JP: We did an interesting online auction for the Indiana Medical Society a couple of years ago. They had items from an estate in Indianapolis that were donated to them. We got to sell some really cool art from a local Indiana Hoosier artist. But every estate is unique; there is something special in every property. I studied art, so that is my specific specialty. I get really excited when I walk in and see a T.C. Steele hanging on the wall. There is something new to discover in each property. That’s what I love about this business: I am constantly learning.
EC: What do you love the most about owning Flipside?
JP: I love our team, it’s awesome. Our customers are just amazing. They keep coming back and they look forward to our sales and say how much they love them. It is good to hear that people are having a great experience. I mean, I would not do this if people were having a crummy time—it wouldn’t be fun to own and operate a business if no one enjoys it.
EC: What is the greatest challenge you face running your business?
JP: We have grown a lot in the last few years. After year one of running the business, I became the sole owner. Then the pandemic hit, which slowed everything down. But the pandemic helped me grow the business exactly the way I wanted to and at the speed I wanted. Now the speed is ramping up hardcore. We have two full-time employees and three part-time employees. It’s crazy. There are other companies that are franchises that are more established, but we are working to change the face of marketing and honing in on what is important to Flipside Estates.
EC: Where do you see Flipside in the next five years?
JP: Hopefully we are having sales every week and growing our team to be even larger. Also, having a storefront would allow us to feature really nice objects that we are selling for our clients.
EC: Can you tell us about your upcoming events and ways to shop Flipside goods?
JP: We have a few online auctions coming up and an estate sale on November 11 and 12. Our website is a great source to check out our sales. We have consignment stored at a warehouse in Fountain Square that we open to the public to shop from once or twice a month. We also have a couple of retail spaces too, so there are lots of opportunities to shop Flipside goods. The best way to keep up on our events is to follow us on Facebook and Instagram.
