Episode 323: How to Declutter Your Home and Make Money Selling Pre-Loved Items with Jessica James
You Did the Decluttering. Now Here's What to Do with the Piles.
The piles are done. You sorted through the closets, cleared out the garage, and set aside everything you are finally ready to let go of. Now you are staring at all of it, wondering what actually comes next.
That is the exact moment Jessica James built Madilyn James for.
Jessica is a serial entrepreneur with a background in tech. Before launching Madilyn James, she built and sold a background screening company that worked directly with court systems across the country. After taking a year to regroup following that sale in 2020, she came back to entrepreneurship with a clear focus: make it as simple as possible for anyone to sell secondhand items online, turn clutter into real income, and do it without juggling multiple platforms or paying anything upfront.
In this episode of the Game On Girlfriend® podcast, Jessica walks us through exactly how Madilyn James works, how she built it, and what it actually looks like to set up a free storefront and list your first item in under a minute. We also get into the decluttering process itself — where to start, how to decide what to sell versus what to donate, and why clearing your space can be just as good for your mental clarity as it is for your bank account.
If you are new here, welcome. The Game On Girlfriend® podcast is for women entrepreneurs who are building businesses on their own terms. Whether you are just getting started or well into your journey, you are in the right place.
Watch the Full Episode
How to Sell Secondhand Items Online With Madilyn James
When Jessica was researching the resale space before launching, she kept running into the same problem: every type of item had its own platform. Clothing went one place, art went another, and handbags somewhere else entirely. Keeping up with multiple accounts, multiple logins, and multiple sets of rules was enough to stop most people before they ever listed a single thing.
"No matter what someone was trying to sell, there were different platforms you had to go to sell that item. Art: you might lean one way; clothing, another site. How do you take a platform and create a platform for everyone so they don’t have to have multiple accounts? So that was the point of Madilyn James." — Jessica James
Madilyn James was built to solve that. One account, one storefront, every category of item — all in one place. You set it up once, tell your story, and start listing. There is no upfront cost, and no commission is pulled from your earnings until an item actually sells.
Beyond the listing process, the platform also takes care of something a lot of sellers do not think about until it is too late: getting found. A dedicated Madilyn James team handles search optimization, paid ads, and social media so your items get in front of buyers — without you having to build a whole marketing strategy on top of everything else. For sellers who want even more visibility, there are also opportunities to be featured on the platform's own social channels and podcast.
Because Jessica came from a tech background, she built the platform with everyday users in mind, not just people who are already comfortable with technology. The feedback she has consistently heard from early users is that it is intuitive — and that the AI built into the platform feels like a helper, not a takeover. As Jessica put it, it is your co-pilot, not the pilot.
Where to Start When Decluttering Feels Overwhelming
Jessica talks with professional organizers regularly, and the approach she recommends is one of the most straightforward I have heard.
Start with the area of your home where you feel the most stuck. Not the biggest area, not the one that has been bothering you the longest — the one where you feel it most right now. Finish that space completely before moving on to anything else, both clearing it out and organizing what stays.
"I walk around my home, and I feel where do I feel cluttered, where do I need to cleanse? That’s where I start. I don’t move onto another area until I have finished that area." — Jessica James
Once the area is cleared, the next step is sorting. Jessica recommends getting donations out of the house first—drop them off, schedule a pickup, whatever gets them out of the house the fastest. From there, take the items that have real value and organize them by category or price point before you start listing.
For anyone who gets to that pile and immediately feels behind, there is also an option to skip the listing process entirely. Simply ship the box to Madilyn James, and their team will build the storefront and list the items for you.
"There are health benefits to not living in clutter and to being organized. I do believe that it brings our anxiety levels down, which we could all use in this day and age." — Jessica James
Starting a Business Does Not Have to Be Complicated
Jessica never saw herself as an entrepreneur growing up — even though both of her parents ran their own businesses. She watched the stress and the pressure and decided early on it was not for her. Then she built two companies anyway.
Her first business grew from spotting a need that was not being met. The second one followed the same instinct. What she tells anyone thinking about starting something — whether a side hustle on Madilyn James or anything else entirely — is that the biggest mistake most people make is overcomplicating the start.
A large investment is not required. A full team is not required. In fact, you do not need everything figured out before you take the first step. Start with two items listed on a platform that costs you nothing until something sells, and go from there.
"You start simple. I think that's the problem — everyone overcomplicates it. You really can start small and start simple without much spend." — Jessica James
The Listener Offer — And Why Secondhand Is Worth Your Attention
Before wrapping up, Jessica shared a specific offer for Game On Girlfriend® listeners. Sign up for a free account through the link here, and you will be locked in at a 7.5% commission rate. That means if you sell something for $100, you keep $92.50. No setup fee, no monthly cost, and nothing pulled from your earnings until a sale goes through.
For anyone who has been meaning to clear out the closet, move the kids’ outgrown clothes, or sell quality items that are just sitting in boxes — there is very little standing between you and taking the first step.
On the secondhand side of things: I wore a secondhand sweater for this very recording. Pre-loved clothing has been part of my wardrobe for years, and that is not changing. There are already more than enough great pieces out there in the world. Giving them a second life rather than sending them to a landfill is the kind of small, consistent choice that adds up over time — for your wallet, and for the planet.
"It's not scary, you have nothing to lose. It's incredibly simple but intuitive at the same time, where the system will actually assist you." — Jessica James
Listen to the Full Episode
About Jessica James
Jessica James is a serial entrepreneur in the tech industry, now launching her second venture in e-commerce with a mission to reinvent the retail experience by curating unique, pre-loved, and sustainable fashion finds while fostering a vibrant community of sellers and shoppers. She founded Madilyn James with the clear purpose of empowering entrepreneurs, providing sustainable shopping opportunities, and giving back to the community.
After successfully building and exiting her first venture, she has applied the same principles around simplicity, service, and client focus to Madilyn James. She has built a team of experts across industries to redefine retail and put more profit back in sellers' pockets. Madilyn James was chosen as the company name because it is a family name, reflecting values of work ethic, empowerment, and community. Like its namesake, Madilyn James gives back by supporting future leaders and the veteran community. Jessica values family time with her husband and two boys and loves spending time outdoors.
Connect with Jessica
- Website: Madilyn James
- Instagram: @themadilynajmes
- TikTok: @madilynjames
- Facebook: @madilynjames
Jessica's Free Gift for Game On Girlfriend® Listeners
Sign up for a free account at Madilyn James and list your first items using this link here. As a podcast listener, you will be locked in at a 7.5% commission rate — that means more money stays in your pocket from every sale. No setup fee. No upfront cost. Nothing is pulled from your earnings until your item sells.
Related Episodes You'll Love
Episode 259: How Building an Email List Helped Increase My Revenue 10X with Sena Wheeler — Sena built a product-based e-commerce business selling wild Alaskan seafood direct to customers — and learned the hard way that building something great and actually getting people to find it are two very different things. If Jessica's conversation got you thinking about selling online, Sena's episode is the next practical step. Listen here
Episode 80: Your Business Is NOT a "Hobby" with Nicole McKay — Nicole launched AugiDog Art — a product business turning pet photos into custom canvas art — three months before COVID hit. She kept going anyway. If you have been sitting on an idea you have been calling a side project, this episode will give you permission to take it seriously. Listen here
Episode 174: Committing Until It Takes with Kimberly Spencer — Kimberly's path included an e-commerce startup that did not go the way she planned — and what she built next because of it. Her message about starting one step at a time and not waiting until everything is figured out runs directly alongside what Jessica shares in this episode. Listen here
Let's Keep This Conversation Going
Ready to build a business that actually supports your life instead of consuming it? Let's talk.
I offer free 15-minute consultation calls. We'll talk about where you are in your business and see if working together feels right.
Connect with Sarah
- Instagram: @thesarahwalton
- LinkedIn: Sarah Walton
- Free resources for you
- Join the Game On Girlfriend® community — subscribe to the podcast on Apple Podcasts, Spotify, or YouTube
Love This Episode?
If this conversation gave you a push to finally clear out those piles and do something with them, pass it along to a friend who has been putting off the same thing. Sometimes, just hearing that the first step is simpler than expected is all any of us needs.
About Sarah Walton
Sarah Walton is a business coach and the host of the Game On Girlfriend® podcast. Her mission is simple: to put more money in the hands of more women. She helps women entrepreneurs build profitable, sustainable businesses without burnout — working through both the mindset and the strategy sides of growth. Because when women have more financial power, they don't just keep it — they use it to take care of their families, support their communities, and build something bigger than themselves. Through her programs — including the Abundance Academy and The Art of Receiving — along with her online courses and one-on-one coaching, Sarah works with women who are ready to build profitable businesses and use that financial power to make a real difference in the world around them.
Binge More Game On Girlfriend™ Podcast Episodes
GRAB MY FREE FREEDOM CALCULATOR SO YOU CAN:
Learn the exact number you need to feel FREE!
Know exactly what you need to do each day to make more money.
Make tracking your numbers easy with my revenue tracking tool (the same tool I use every day in my own business!)
Learn the TOP 2 mistakes most business owners make when it comes to tracking revenue
It's time to move from "fingers crossed" to clear and successful.