generic 17 Money Experts Reveal Their Best and Worst Purchases Ever
Some purchases bring you joy, while others leave you feeling nothing but regret -- and even financial pros and celebrities aren't immune to these highs and lows. GOBankingRates spoke to money experts like Rachel Cruze and influential personalities like Deepak Chopra to get their picks for their best and worst purchases of all time -- here's what they had to say.
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Cheryl Casone, Host of Fox Business Network's 'American Dream Home'
My Best Purchase: The best purchase I ever made was buying my first home when I was 22 years old. My great-uncle passed away and he left me a small inheritance. Instead of going out and buying a new car or clothes or jewelry, I wanted to buy a home.
My Worst Purchase: The worst purchase I ever made was an overpriced pair of boots. Let's just say they were/are very uncomfortable. So lesson learned -- if you can't wear something or use something, then why buy it?
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Deepak Chopra, Co-Founder of Never Alone
My Best Purchase: A magnet I bought as a teenager. [It] convinced me that reality is mostly invisible.
My Worst Purchase: A black tie outfit I bought to visit an Obama White House ceremony. I never wore it! I hate ties, so I went as usual in casual [clothes].
Mallika Chopra, CEO of Chopra Global
My Best Purchase: My iPhone -- it keeps me connected, captures my memories and organizes my life.
My Worst Purchase: My iPhone -- it allows me to escape uncomfortable situations for growth, distracts me from experiencing the now of special moments and restricts my ability to live free of my schedule.
Rachel Cruze, Author of 'Know Yourself, Know Your Money'
My Best Purchase: When it comes to best and worst purchases, we've all done it. Sometimes something we think is important is a waste. A good question to ask yourself when debating a purchase is, "If no one sees it, do I still want it?" Meanwhile, there are a few things I have bought and haven't had buyer's guilt over. For example, things I use every day are what I consider a good investment. Some of my best purchases include a nice hair dryer, good makeup brushes and an extra-long phone charger.
My Worst Purchase: On the flip side, some of my worst purchases include expensive designer shoes, beauty product subscriptions and streaming services we don't even watch.
Tori Dunlap, Founder of Her First $100K
My Best Purchase: The best purchase I've ever made is Friendmoon, the honeymoon-style trip I always take with my friend. We've traveled to Costa Rica, Italy, done a national park road trip, and last year we spent two months in Europe.
My Worst Purchase: The worst purchases I ever make are when I spend a lot of money on food and the food ends up tasting disgusting, or when I spend a lot of money on food and it's microscopic and I leave feeling like I need to have a burger. It feels like you need double dinner.
John Eringman, @johnefinance on TikTok
My Best Purchase: My best purchase, by far, was buying a duplex in 2020. I lived in one unit and rented out the second unit. This significantly lowered my living expenses.
My Worst Purchase: My worst purchase was buying a sports car in college. People don't understand that with a more expensive car comes more expensive maintenance, gas and insurance. It's one of the worst financial decisions any college student can make.
Nick Ewen, Director of Content at The Points Guy
My Best Purchase: $1,949.94 for a six-night trip to Ireland for me and my wife. We saw a special on TravelZoo several years ago, and for less than $1,000 per person we got six nights in hotels -- two each in Limerick, Castlebar and Dublin, daily breakfast, an automatic car rental with unlimited mileage and GPS, and round-trip flights from New York-JFK to Dublin. Even better? Both flights were oversold in economy, so we were bumped to business class (for free) thanks to my Delta elite status.
My Worst Purchase: I once redeemed 47,500 Delta miles to fly from Florida to New York round-trip, with one of the legs in domestic first class. For such a short flight, it was really silly to reserve a seat up front, as I could've saved a bunch of miles by flying economy.
David Greene, Host of the 'BiggerPockets' Podcast
My Best Purchase: A fourplex apartment building in 2012. [I] bought it for $250,000 and rents for each unit were $700. Ten years later, rents are now $1,750 but my mortgage is the same!
My Worst Purchase: A much nicer car than I ever needed. I spent $20,000 on it in 2003 when I could have bought something for $8,000. I ended up being $10,000 short to flip a house the next year and that cost me $50,000 in profit! Had I not bought the expensive car, I could have flipped the house. Lesson learned!
Pat Hiban, Co-Author of 'The Quitter's Manifesto'
My Best Purchase: TSA PreCheck and Global Entry. The time I save waiting in line during such stressful times is worth the cost 100 times over!
My Worst Purchase: A lifetime subscription to TIVO. This was the future of TV where I could record any show I wanted to for the rest of my life. The cost was five times a yearly subscription, but I knew I'd be winning on that deal! Within a year DVR came out from cable companies and streaming services arrived not long after that.
Mindy Jensen, Co-Host of the 'BiggerPockets Money' Podcast
My Best Purchase: A tile saw. We do live-in flips and lay a LOT of tile. Buying a $99 tile saw about 17 years ago has allowed us to smoothly cut all types of tile, including stone and glass, to give our rehabs a high-end look without paying high-end prices. We still have the same saw, which has paid for itself over and over and over again across the years. Another great tool purchase is the flooring nailer. We've used it less frequently, but it cost $150 to purchase and would have been $125 per week to rent. It was a no-brainer to purchase because I didn't know how long it would take to install the floor, and I didn't want to rush through it to try to get the tool back in time.
My Worst Purchase: A lake house in Wisconsin. Super high taxes, problematic rehab. It was our seventh live-in flip -- so we knew what we were doing -- but it was our first pop-top, meaning we took a single-story house and added a second level. It was one disaster after another. We purchased it in the fall of 2006 and the housing market crashed during our renovations -- and so did our potential profits. Our $350,000+ profit dwindled to $100,000, and it took more than 18 months to sell.
Dustin Lemick, CEO of BriteCo
My Best Purchase: I bought tickets to game seven of the World Series, Cubs versus Cleveland. As a lifelong Cubs fan, it is an experience that no price can be put on.
My Worst Purchase: In my 20s, I thought buying a timeshare would be a good idea. It wasn't. Don't do it.
Samantha Melting, SVP, Head of Consumer Bank at Synchrony
My Best Purchase: My best purchase has been a dream vacation to Europe with my daughter. We set a financial goal and saved for an entire year to make sure that we'd have a trip of a lifetime without going into debt to pay for it. When the time came, we had enough money saved to pay for our trip. We made many wonderful memories and will never forget the people, food and experiences we had.
My Worst Purchase: My worst purchase was leasing a brand-new car so the monthly payments would be affordable. At the time, I didn't fully understand that I would be making monthly payments on a car I'd never own and would ultimately spend more money through fees and depreciation to keep the car when the lease ended. I learned this was a costly financial mistake, and now I prefer to buy a certified pre-owned vehicle that I can pay for in cash.
Taylor Price, @pricelesstay on TikTok
My Best Purchase: I've spent a lot of time, money and energy on education, particularly books, involving self-help, career, finance and health. Educating yourself is the best way to guarantee a better life than you could otherwise. It's important for me to be able to help others as well as myself, so that I can also impact their lives positively -- or at least inspire them to do better things with their lives, too!
My Worst Purchase: The worst purchase I've made was buying a used, faulty washer on Facebook Marketplace for my new home. The first floor of the house became somewhat of a "lazy river" and I had thousands of dollars in water damage. Note to self: Always buy a new washer.
Bobbi Rebell, Author of 'Launching Financial Grownups'
My Best Purchase: I splurged on a very expensive Moncler coat. I had read a review of it in a magazine that went through the way the coats were made and why they were worth the high cost. I bought it in a dark purple color and loved it for about five years with many compliments. The best part: I re-sold it on The RealReal for almost as much as I paid, and in turn bought an updated style in black that I still have today!
My Worst Purchase: A Hamptons share right after I bought my apartment at age 23. I had equity in my new home and took out a home equity line of credit to pay for the Hamptons share -- and all the nights out and expensive meals/cocktails/cute outfits that came with it. I didn't want to ask my parents for help because I wanted to be independent, so I was independently in debt!
Kennedy Reynolds, Chief Education Officer at Acorns
My Best Purchase: My best purchase has been my passport, and almost every trip I've taken with it. Those experiences have paid off in spades, without expiration.
My Worst Purchase: If I could, I'd take back just about every clothing, shoe and accessory splurge, and almost every toy I've bought for my kids! Imagine adding those up and investing the total instead. Kids play with toys for a day. The material stuff goes out of style. If I had invested that sum in my Acorns diversified portfolio, I'd have way more than a fancy pair of jeans.
Jaspreet Singh, Founder of Minority Mindset
My Best Purchase: Business class airline tickets to India. Growing up, I would make the 20-hour journey to visit my family in India in economy class. It was brutal. Sitting in business class made it a whole new experience. It's expensive, but the flight is actually enjoyable now (plus, I can get a lot of work done in the air).
My Worst Purchase: A tricked-out Toyota with custom rims, HID lights, subwoofers and an upgraded sound system. In high school, anytime I made money I spent it upgrading my Toyota. I was trying to look rich but in reality, I was just making myself broke.
Tom Wheelwright, Author of 'Win-Win Wealth Strategy'
My Best Purchase: A CPA firm I purchased in 2001. One of the clients was Robert Kiyosaki, and he has become a great friend and mentor to me.
My Worst Purchase: A CPA firm I purchased in 2003 in Virginia. The clients did not match our normal profile and the staff could not handle our normal work. [It's] best to purchase businesses that better match your brand.
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Jaime Catmull contributed to the reporting for this article.
This article originally appeared on GOBankingRates.com: 17 Money Experts Reveal Their Best and Worst Purchases Ever
