Making Money in Retirement: How This Couple Made $6,800 Flipping Items

retirement life

Flipping more items. Yep, that’s my plan for making money in retirement AND staying healthy. Melissa and I have literally picked up and sold thousands of dollars worth of free items on our daily walks in the morning.

Flipping is flexible, fun, challenging – and an added bonus – I can make some pretty great money doing it while I’m getting in my daily exercise.

Jack and Joan are retired and are two very active, productive people – logging in up to 38 miles of walking per week!

For a few years, they have been throwing around ideas for a side hustle that would fit their retirement lifestyle of staying fit, traveling, and some pretty amazing financial goals for an inheritance to pass on to their kids!

Then they discovered flipping!

We are super stoked they are making money in retirement by flipping used items!. In between their travel adventures, daily walks, and stretching routines, they have been killing it with their flipping hustle – adding $6,800 to their retirement income!

We hope you are as inspired by their story as we were!

How it All Began

Growing up, I lived in a farming and coal mining region southwest of Pittsburgh, PA. So, after the passing of my Grandfather, and at the age of fourteen, my single uncle asked me to help at the family dairy farm. 

Through high school, college, and after college I was a Jack-of-all-trades on the farm and loved the work. Yet seven days a week was not my desired destiny. 

My wife, Joan, grew up in Allentown, PA as the second of five children. She lost her father from cancer at the age of ten. This is where she learned how to be thrifty at an early age. 

On our first date, Joan impressed me in a number of ways. During a full moonlit walk, she shared that the beautiful suede jacket she wore was just $1 from a yard sale! 

I chuckle about it now that I knew then she wasn’t going to be a high maintenance partner! 

Together, we found that we shared a fondness for bargain shopping from the beginning. Just a month into our relationship, we had visited a flea market where Joan managed to purchase a down-filled sleeping bag for only $5 and a variety of other items using her bargaining skills. 

That afternoon, surrounded by the great bargains we found that day, I proposed to her and she said yes!! We were married in March 1998. Together, we both have been and continue to enjoy milling through flea markets, yard sales, and popping into thrift stores. Joan is still relentless, in a nice way, of getting the bottom dollar!

In July 2000, we relocated from Central Pennsylvania to Cape Canaveral, Florida for an important employment opportunity for me.  I stayed with that position until I retired at the end of 2018 while Joan formally retired exactly one year later. 

staying fit

We have two successful daughters, Jaclyn and Gina, and two pre-school granddaughters, with a grandson due when we flip the calendar into 2021.

An “Aha” Moment

We have been enjoying our retirement life and I just recently turned 66. You know what that means? I can figuratively put the “pedal to the metal” on my earnings without additional income impacting my social security income!

Joan and I had been mulling around ideas for making money in retirement for quite some time.

We threw around ideas of what we could do as a side hustle. A few years ago, I had heard Rob “The Flea Market Flipper”  on Nick Loper’s “Side Hustle Nation” podcast. I was intrigued then, but never pursued it further.

This year, on Nick Loper’s program he had another guest, Stacy Gallego, enumerating her successes and challenges as a professional flipper. I made the connection that this was one of Rob’s Flipper University students.

There is an old saying: “When the student is ready, the teacher will appear.” In 2020 we decided that now was the time to start making money in retirement with a lucrative side hustle to add to our already enjoyable and active retirement life!

We were bouncing ideas off of each other but nothing got us excited for more than a couple days. 

That day, when I listened to Stacy, “bingo!” I thought this may be our pathway forward! Stacy related her experiences in a down-to-earth, matter-of-fact tone. I called Joan and said,  “I have to share something with you!”

After we repeatedly listened to that interview, we let the thoughts ruminate for several days. We realized, this was a great way to make money in retirement and the side hustle we had been looking for! That is how impactful the message was and how we could relate to this becoming our reality for ourselves.

My personality is that of a Doberman with a bone-in-his-mouth. That’s pretty much how I’m wired. With that said, once I get something in my jaws, it is hard for me to give it up. 

Joan on the other hand is calm, compassionate, and likes the thrill of the hunt. So as we thought tossed around flipping as a viable side hustle option, we thought about how flipping could take her passion for “shopping” and wrapping a “business” around it.

It was on our way to Savannah, GA to visit our oldest daughter’s family that I told Joan, “If we are going to move forward, I want to move forward the right way and that means getting the proper education.” Joan had us signed up for Flipper University before we hit the Georgia border and were on our way!

Continuing the Family Financial Legacy

Our social security and pension income totals $4,500 per month. Some might say, “Yo dude, take a stool.”  But sitting on our duffs in our retirement just isn’t how we are wired. 

We chose flipping as our side hustle because we felt it would be a really nice fit to our retirement life. With that said, it’s our goal to grow our reselling endeavors to equal our passive income.

Why? We love to travel and want the financial freedom to do it if we choose, while continuing to grow our hard-earned savings. 

Our travel goals currently include the Grand Canyon, which is at the top of the list, then Portugal when Covid-19 is in the rearview mirror! I also want Joan to experience Capulin Mountain National Monument – an extinct cinder-cone volcano in New Mexico. On a trip around the US in 1981, I drove to the top of it!   

We are looking forward to making some serious money in retirement to meet our travel adventure goals.

Flipping to Provide an Inheritance

In addition, we also have a desire to provide a significant inheritance (shooting for seven figures each) for our daughters and their growing families.

Making money in retirement

My late mother was a product of the Great Depression and a good financial mentor in her own way. She grew up on the family farm and was very frugal. During her and my father’s retirement of thirty years, they combined frugality with the miracle of compound interest, to grow a modest five-figure savings into a six-figure nest egg for me and my brother.

This was an amazing gift and we want to pass on that family legacy to our own kids.

Joan and I are willing to take more of a risk and replicate that legacy for our girls. We are both big givers and enjoy benevolent acts for family, friends, and neighbors.

I see those that are involved with Flea Market Flippers earning well beyond our current goal. We have no reason to think we can’t make money in our retirement doing exatly the same!

We plan to join them sooner than later and grow our nest egg to pass on a nice inheritance to our daughters.

Flipper U Gave Us Knowledge and Tools

Before getting involved with Flipper U, we just saw a disparate conglomeration of stuff out there in the marketplace. For us, we did not envision a profitable pathway forward by flipping random items. We knew we enjoyed yard sales, flea markets, and the like but never thought about it as a way to meet our financial goals.

Flipper U has provided the fundamentals with specific tools and techniques, while figuratively removing the mental clutter and doubt.

We now see the world around us with a fresh set of eyes, and it is a big, big world! And then when you add in the resources provided by the Flipper group on Facebook, it gets even bigger! 

These are some great people sharing their successes, techniques, and answering our questions. We consider Flipper U to be the “Master’s Program” and we are ready for any challenge that comes our way.

Sourcing Coupled with Staying Fit!

We’ve found that sourcing and fun and staying fit in our retirement go hand in hand and that makes for the perfect retirement side hustle to make money in retirement! 

We recently drove to Cape Canaveral to pick up a resale item. After the transaction, we ambled down the Astronaut Hall of Fame walk. We held hands along the shores of the Indian River estuary while we viewed the NASA Vehicle Assembly Building and Rocket Launch Pad across the bay.

We both love nature and science.

After our romantic walk, we topped off our excursion with some of the best homestyle ice cream ever. We realized we were having fun while we were making money.. 

To us, this is a very profitable and healthy way to stay fit and to enhance our retirement life by mixing a little business with pleasure! 

Turning Our Daily Walks Into Cash!

Every morning since the mid-80’s, I’ve gone for a walk to stay fit and healthy. On January 1, 2017, I began logging my miles with the help of a Fitbit. 

On average, I walk 38 miles per week! And since Flipper U, my eyes have been opened and Lord only knows how many items of value I have walked by in these past decades!

But not anymore!

Since Flipper U, I realized my walks could serve a dual purpose – I could stay fit and make money! Joan and I enjoy going to new areas and walking in a variety of settings such as neighborhoods, downtowns, and upscale communities. 

On our daily retirement walks, we’ve run across quite a few free items sitting on the side of the road that were worth money! Since we started our flipping side hustle in 2020, I am seeing things that I was oblivious to before!

I’ve nabbed tables, chairs, rattan swivel chairs, a gasoline powered Ryobi leaf blower, boxes for shipping items, and even an entire roll of bubble wrap for packing my shipments!

Just last week, I picked up a two drawer Bush file cabinet curbside that only needed a minor cleaning. These cabinets retail for over $250! 

Joan and I plotted the solid waste pickup schedules for our area and we added these two days  to our exercise routine. Now we travel short distances to these areas for our morning routine and have found lots of treasures awaiting! 

For us, staying in good physical condition helps us with the lifting and carrying that we do with our new side hustle. My father passed at 90 and my mother at 93, an uncle at 98, and my mother’s oldest sister will be 103 in March of 2021! 

Joan and I want to live a long and productive retirement life – but it takes work! Now our conditioning activities have taken on a whole new level of productivity and it has added enjoyment (not to mentioned making money in retirement!) to our healthy lifestyle!

Developing an Eye for Treasure and Negotiating

Though we are not too long-in-the-tooth as professional flippers, we have learned quite a bit since being in Flipper U. In past years, we’ve flipped several mobile homes, motorhomes, motor bikes, and household furnishings. So we aren’t totally new to flipping. 

But Flipper U has helped us develop new, valuable skills for the long run!

We have sold a top quality inversion table, bicycle carriers and exercise equipment. Last weekend we sold a Yakima Rack and Roll trailer (it transports bicycles and kayaks). Not too bad for beginners!

Our eyes have been open to a whole new way of sourcing and selling – freight shipping!  

Making money in retirement

I recently picked up a 5th wheel truck hitch off of Craigslist. It retailed for $1,500 and I picked it up for $150. The seller had no need for it and his wife was pressuring him to get rid of it!

I also went to a yard sale the same day and found a unique item. After looking it over for some time, I figured out that it was a pull-down attic ladder! Not one of the old ones, but a brand new one made in Austria!

She sold it to me for $7 and it retails for $950!

A few days later, I picked up a Scoota Trailer and a Jazzy Elite ES Power Wheelchair as a package deal. A family had lost a family member and by  them selling these, they would remove one more perceived burden off their plate.

These items were in great condition, but I still put a “new car’ luster on both of these guys. This will be our largest flip to date and will be marketed in the $5,000 range! 

making money in retirement

This was a win-win for us and the teaching contained in the Flipper U course and the people we interact with in the Flipper Group helped us make this a reality! 

Flipping is not a get rich scheme, it takes time, courage, and commitment to become more tomorrow than you are today. But we are up for the challenge.

Education is Cheap Compared to Ignorance

Joan and I have a saying:  “Education is cheap compared to ignorance.”  We knew with flipping if we were going to tackle something new, we needed to understand how the professionals do this business.

We realized if Stacy Gallego was meeting success with reselling items and she was so down to earth and real, then with the formal training she received, we could do this too. 

Happily, we are now creating our own path in this business! Get this, there is not one or two paths in this profession, but multiple paths to pursue based on your interests and passions. 

All of us select the paths we lead in life for we each create our own success in flipping by continuing to educate ourselves and do what interests us. 

Luck is often defined as when preparedness meets opportunity. Flipper U and the live Facebook feeds offered by Rob and Melissa and the like-minded participants continue to prepare us. And we look forward to what retirement life has in store for our future!

What We’ve Learned on Our Flipping Journey

For us, learning to assess what items were worth buying so each item produced enough value to earn solid profits when it resold. 

The bicycle analogy fits this period well. Did you ride a bicycle perfect your first day out? Of  course not, none of us did! As with flipping, the more you do, the smarter you get and the smarter you get the more your profit margins grow. 

We have also realized that space can be a bit of a challenge for us. We live in a 3-bedroom condominium that fits our senior lifestyle but does not afford us a ton of space to accumulate bigger items. 

We stepped up to one rental unit – 30 x 10 and soon followed with a second unit – 20 x 10. One is climate controlled while the other is not but has a roll up door with immediate outside access. This has helped us stay organized and have the space to store when amazing opportunities to source arise!

When we started flipping, we had a full range of emotions from “what have I done?” on the low side to “OMG, I can’t believe I just did this, I am so excited”. These little emotions will come, and the Flipper Facebook Group helps keep you focused and in proper perspective. 

Yes, this is a business where we are in business by ourselves but there is ample support and comradery when you hang around like-minded people!

We would conclude that it starts at the top, and the Founders of Flea Market Flipper University, Rob and Melissa Stephenson are honest, generous and dedicated individuals that are tireless in their support of those of us who are out here doing it.

I was asked the question recently, “Knowing what you now know, would you pay to go through the Flipper U course again?

Consider this from the family horticulturist: The best time to plant a tree was twenty years ago and the second-best time is NOW. We are extremely thankful we got our tree in the ground! We are very happy where we are and are looking forward to a long and productive retirement life filled with flipping in our future!

What a great success story on how to stay fit in retirement and make money while doing it! We look forward to hearing how flipping enhances your retirement years!

How about you? Are you nearing retirement and trying to figure out what to do to stay active and productive? Flipping might be for you! Check out our free intro webinar TODAY!


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Robert Stephenson

I grew up in Central Florida and have lived here my whole life. I first got into buying and selling items when I was 16 years old, and have been hooked ever since. It has mostly been a hobby that makes some extra cash, but sometimes it serves as my main income as well. I don't plan on stopping any time soon. I find too many fun toys for my family (or myself), and just love the whole process.

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