Josh Opperman is the co-founder of I Do Now I Don’t, a digital platform that leverages the power of the sharing economy to connect buyers and sellers of gently used engagement rings and other wedding accessories.
Opperman, a graduate of Ithaca College in upstate New York, founded I Do Now I Don’t in 2007 after a painful personal experience that led him to reassess his priorities. Opperman returned home one day that year to a house completely abandoned by his fiancée of three months — with the exception of the engagement ring Opperman had gifted her. Opperman’s attempts to return the ring were equal parts insulting and Kafkaesque; in the end, all he had to show for the effort was a laughably low buyback offer from the original retailer.
The experience got Opperman thinking about the glaring gaps in the wedding jewelry resale market and the clear opportunities available for an entrepreneur willing to put in the work to address them. As he puts it: “Rather than get mad, I decided to break even, and that’s when I launched I Do Now I Don’t.”
Resolving to develop and scale a more humane way for people to buy and sell previously owned engagement rings (and, later, other wedding accessories), he teamed up with his sister, Mara, and set in motion a chain of events that all but removed the middleman from the process. The Oppermans settled on a starting price point that was fair to both buyers and sellers: about 50% of original appraised value, on average, with I Do Now I Don’t taking a modest cut of each sale.
Upon its launch, I Do Now I Don’t caused an immediate stir, with favorable coverage from the likes of Whoopi Goldberg, Anderson Cooper, and Rachel Ray. The growth of the peer-to-peer economy fueled I Do Now I Don’t’s expansion, and a strategic merger with DELGATTO in 2015 turned the company into a true jewelry resale powerhouse.
Today, I Do Now I Don’t hosts nearly 2 million sales totaling more than $4 billion each year. Opperman remains involved in the company’s day-to-day operations in his role as a senior partner in DELGATTO’s diamond finance fund. He lives in the New York City area.
Where did the idea for I Do Not I Don’t come from?
I came up with the idea after my ex-fiance broke our engagement. All I was left with was the engagement ring I no longer wanted and needed to return. To my dismay, however, I discovered that many stores do not accept such returns and would present a buyback offer that was a fraction of what I paid for the ring. I concluded that there should be a better and safer way to sell diamond engagement rings. So, with the help of my sister, Mara, we launched IDoNowIDont.com.
What does your typical day look like and how do you make it productive?
There is no typical day at the office for me. Every day is different and varies — from conference calls to meetings to even brainstorming with the team for new ideas. I wear multiple hats and enjoy taking part in all the different aspects of our business.
How do you bring ideas to life?
We have weekly brainstorming sessions with the team. We use a whiteboard and everyone participates by contributing new ideas. We then talk through the ideas and see what is profitable and what works best for the business. After that, we talk with the development team to see if the proposed idea is something that we can implement on the platform.
What’s one trend that excites you?
I really love technology and appreciate how far technological advances have come. These days, I have been spending time using the Oculus virtual reality technology. Virtual reality’s capabilities are redefining the way we do business, education and even healthcare. I find it all fascinating.
What is one habit of yours that makes you more productive as an entrepreneur?
I make sure to set aside time for myself and my family. Because I am technically always working, it’s important to turn off everything and just be present with my family for a few hours each day.
What advice would you give your younger self?
I would share with my younger self the importance and the power of perseverance. As Thomas Edison put it, “Many of life’s failures are people who did not realize how close they were to success when they gave up.”
Tell us something that’s true that almost nobody agrees with you on.
I am really good at cooking. My daughter may agree but I doubt anyone else would.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
I aspire to do better year after year, first and foremost. Because I’m an early riser, I’m able to enjoy a cup of coffee and catch up on the news before starting my workday. I truly believe that no matter what line of business you’re in, it’s important to catch up daily on what is going on in the world, politics, technology, entertainment and, of course, business. I like to be knowledgeable on all subjects and be at the forefront of technology.
What is one strategy that has helped you grow your business?
It’s always important to remain relevant. But, even while staying on top of the latest trends/technology in our space, we have always maintained our core business model. We simply expanded the things we offer and added more value to it.
What is one failure you had as an entrepreneur, and how did you overcome it?
When we first started our business, we hired a business consultant to help with our expansion. The consultant thought it would be a genius idea to turn our ecommerce site into a social networking site as well. We wasted time, money and resources on this project and I think the actual addition to the site only lasted about two months or so. I was never keen on the idea and should have been more vocal about it. But, when we tested it and concluded it didn’t work, we removed it from our site and moved on.
What is the best $100 you recently spent? What and why?
The best $100 I recently spent was a donation to a charity on behalf of a friend.
What is one piece of software or a web service that helps you be productive?
I am a big fan of Salesforce. It helps us integrate all the different areas of our business into one platform. Salesforce’s CRM software keeps everything related to managing your customer relationships — data, notes, metrics. It is an essential part of the business.
What is the one book that you recommend our community should read and why?
“The Tipping Point,” by Malcolm Gladwell. This book shows how small actions performed at the right time, in the right place, and with the right people can create a “tipping point” for anything. The “tipping point” is “that magical moment when an idea, trend, or social behavior crosses a threshold, tips, and spreads like wildfire.”
What is your favorite quote?
“I have learned that success is to be measured not so much by the position that one has reached in life as by the obstacles which he has overcome while trying to succeed.” – Booker T. Washington
- Realize the importance and the power of perseverance. As Thomas Edison put it, “Many of life’s failures are people who did not realize how close they were to success when they gave up.”
- Virtual reality’s capabilities are redefining the way we do business, education and even healthcare.
- No matter what line of business you’re in, it’s important to catch up daily on what is going on in the world, politics, technology, entertainment and, of course, business.