Stewart Gold on Shark Tank, Entrepreneurship, and Reinventing Baby Products

In this episode of Uncorked: Wine-Business-Life with Bill Green, we sit down with entrepreneur and former corporate attorney Stewart Gold, who left the legal world to follow his passion for innovation and entrepreneurship. His journey led him to create Dingle Dangle Baby, a game-changing baby product designed to keep little ones entertained during diaper changes—by strapping it to a parent's head! Stewart takes us through his incredible adventure, from moving his family from Florida to England to landing a deal with Kevin O’Leary on Shark Tank. He shares the highs and lows of entrepreneurship, the risks he took, and the lessons he learned along the way. Whether you're a parent, an aspiring entrepreneur, or love a great business story, this episode is packed with inspiration, insights, wine talk and a few laughs.

Introduction

Welcome to Uncorked: Wine, Business, and Life with Bill Green. I’m Jerrold Colton. We are in beautiful Boca Raton, Florida, and as always, we have a great guest today.

Somebody has a story that a whole lot of people will want to hear. Stuart Gold, our friend from Boca Raton, is so inspirational. I think our audience is going to love listening to Stuart's story.

He was a corporate lawyer for a bunch of years and made a pivotal change in his life after being married and having two children. He decided he wanted to follow some passion. That is what Uncorked is all about.

It turned out that his passion was to be an entrepreneur. He invented an amazingly cool product, and you're going to hear all about it. He went on Shark Tank and got a deal from Kevin O'Leary, an iconic global investor. We're really excited to have you on the show, Stuart.

I’m excited to be here. I followed a pretty typical path for a Jewish kid in South Florida. I went to a private school and then the University of Michigan. I wasn't positive what I wanted to do out of college. I got a political science degree and then went to law school at the University of Florida.

I got my first job at a law firm in New York, but unfortunately, it was during the financial crash in 2009. I saw the law firm was going under, so I made a jump to an in-house job at a hospital. That eventually brought me back to Florida where I was in-house counsel and then general counsel for a number of healthcare companies.

Relocating to Northern England

In 2019, we made a big life change and decided to move from Florida to Northern England. The circumstances were really sad. My wife's sister had passed away tragically at 29 years old, which was devastating for her family and myself.

When you have that sort of event happen, you take inventory of where you’re at and what you’re doing. It took a while for us to get our heads together and figure out the next move. My wife actually spent a number of years in England growing up.

Her dad was at one of the army bases out there. They have a big base in a small town called Knaresborough, England. She had her fondest memories from growing up there, and it was always a goal of hers to try to get back.

She suggested moving to England. I didn’t know how we would get there, so I told her if she could find a job and get a visa, I would go. I was a general counsel at the time and doing well. We were young parents with a one-year-old son.

I never really thought much of it; I thought she was just going through a difficult time and needed a change. About 18 months later, she woke up one morning and said she got an email from DLA Piper. We had a visa and had to be in England in three months.

I try to be a man of my word. I was following this really straight path, doing everything the right way, and this opportunity came up. I said to myself that my wife really needs this, and quite frankly, I was feeling antsy myself.

It was difficult because I was working for my father's company at the time. I had a department and very close colleagues, so that separation period was a difficult few months.

His father was a doctor, medical school trained, and then pivoted to being an entrepreneur. The apple doesn't fall far from the tree. At first, it was such a shock to the family because it came out of nowhere.

There was a bit of anger and grief about the situation because I was taking their young grandson. But to their credit, both my parents were incredibly supportive. Once they let it sit for a second, they said I had to do what I had to do.

Northern England was a beautiful town called Harrogate, which is like the Boca Raton equivalent in England. It was an old spa town, but it was a three-and-a-half-hour car ride from London. Door to door from Florida, it was about a 22-hour trip.

The Inspiration for the Dingle Dangle

Then COVID comes. I went to England initially with the idea that I would do some writing. I had sold some movie scripts in the past and wanted to take a writing course and take care of my young son.

England had one of the worst lockdowns in the world. You needed to show ID anytime you left the house and you had one hour where you could walk your dog. It was like something out of the movies where people were spraying their grocery bags with Lysol.

We didn’t see family for about a year. We were eventually allowed to go back to the States for my sister's wedding. We took a 747 and there were only six people on the plane. It was the greatest thing ever, but it was just a strange time to be in England.

You’re in England without a formal job, your wife is working, and you’re raising a young son. Then you have another son, Westyn. During COVID, we had a little garden out back and became close friends with the neighbors.

One day, my neighbor was changing his daughter's diaper on the grass outside. He had this crazy thing on his head, a covered coat hanger with a little plush toy at the end. I saw his daughter giggling and responding and being really happy.

It hit me because changing diapers is just impossible sometimes. They are kicking and rolling and squirming. Nowadays, parents are taking phones and putting them in the baby's face. I’ve done that and actually dropped the phone on my baby's face.

We saw other solutions on the market where the baby is restrained or tied up. We didn't want to restrain the baby. A lot of dads are taking a very active role in raising their babies now, especially after COVID.

We saw an opportunity to create something geared toward dads. When you look at the baby product market, there's really not much out there geared for dads; it's all pretty much for moms.

There is a product called SnoofyBee, which is a mat where you tie the baby down. It’s a nice product, but it lacked the interactiveness we were looking for. With so much technology, everyone’s answer is usually more technology.

We wanted to introduce something fun and playful that makes parents and babies smile without that. It’s cool to have something to entertain your kids that doesn’t have to be charged. We’ve had thousands of years of changing babies without technology.

Product Development and Sensory Design

If you can just add a little improvement and make the experience more enjoyable, it’s worth it. The product is a modular system. We spent six months going through different designs and looks.

Everything is custom designed with baby-safe Velcro. So many products on the market aren't safety-tested, so it was important that every piece was the highest quality. That’s the lawyer in me.

I’ve become shameless wearing this in front of thousands of people. The baby sees this, and since the first colors they see are black and white, everything is sensory for them. You might look stupid, but the baby is seeing your face and this sensory thing moving around.

It has a baby-safe chime, black and white colors, and moving legs. It captures their imagination for those 30 seconds and freezes them. If the baby yanks on it, you just turn it off and give it to them as a toy.

Branding and Market Strategy

The name came from my partner's daughter. She couldn't really speak yet, but she would call it the Dingle Dangle. It’s funny, memorable, and it stuck. The next phase is to get licensing with sports teams.

The idea is that it's modular, so you could turn this into a rattle. If you’re a Philadelphia Eagles fan, you could introduce your favorite team to your baby from day one. Instead of a plush bear just sitting on a shelf, you’re in their space and in their face.

Wine Selection: Saddlehill Cabernet Sauvignon

It is time to have some wine. We’re drinking the 2022 Saddlehill Cabernet Sauvignon by Ashenfelter Vineyard. We’re really proud of this wine. We did a blind test against two Napa wines, and this was the best of the three.

Intellectual Property and Patents

As a lawyer, the intellectual property aspect comes to mind. People are so quick to say they have to get a patent before they even have a product. It’s expensive; it’s easily 10 grand to even start prosecuting a patent.

We didn't actually file for a patent until we knew we had a viable product. Too many early-stage businesses make the mistake of spending way too much money up front before they've seen if there's a product-market fit.

People get so focused on the patent that they aren’t moving the product along quickly enough. We filed about a year after we started. We did a systems patent for the interlocking modular design.

We received our U.S. patent last year. It’s a powerful tool for an e-commerce product. If somebody on Amazon tries to knock us off, we can get that taken down right away. It is a sprint to get out there fast.

The Shark Tank Experience

My journey to Shark Tank started with a form online. It took me about two minutes to fill out. I got a call back about four days later from a producer. They liked that the product looked crazy because it’s a television show and needs to be entertaining.

The process to get on the show is rigorous. There’s a lot of background checking and testing to make sure you can talk well and there are no issues with the product. They have a reputation to uphold.

It was about a year from when I first applied until I filmed. There are something like 100,000 businesses that apply each season. I felt very proud that we got through. You do a lot of audition videos because they want to make sure you aren't going to stumble on national television.

The part that aired was about 10 minutes, but filming took about an hour. The Sharks were all lovely and positive. It is intimidating when you are 10 feet away from Mark Heumann, Daymond John, and Lori Greiner.

My approach to the ask was very pragmatic. I talked to seven or eight other people who had been on the show. The feedback was to be self-aware. The entrepreneurs who get beat up are the ones who ask for way too much money or overvalue themselves.

If you ask for $2 million for 5% of a business doing $100,000 in revenue, they sniff that out quickly. I went in with something reasonable. I looked at it as a 10-minute commercial for my brand.

We had a little bit of a social media following before, but nothing crazy. We did a full year of sales within two nights of the episode airing. My Shopify app was going off every three seconds.

Securing a Deal with Kevin O'Leary

Everyone else went out, and I had a moment where I realized I didn’t want to go back to my family without a deal. I knew the risk of begging and getting chewed up, but I decided to take my shot.

I ended up getting an investment from Kevin O'Leary. It was very fair and upfront. My business is a small one, so it was a flyer for him. I feel responsible now that he is a partner, and I want to make sure he makes money.

He actually dropped out of the negotiation at one point, and that was my moment. I just laid my cards on the table. He saw the fight in me and that I wasn't willing to give up.

It was $75,000 for 20% and a dollar royalty until he’s whole. He’s the master of royalties. He’s an incredibly smart man, and I have nothing but respect for him and his team.

Transitioning from Law to Business

The skills you learned as a lawyer have come together to make this product a success. You worked your ass off to get educated, so you could take that risk. You knew if you had to, you could be back in the legal game with two phone calls.

I’ve been very privileged with my family who supported me. Most people will never be in the position to take these risks. I felt that if you are in a position to do that and you don't, you squander it.

Wine Selection: 2018 Aperture

We should taste the 2018 Aperture. It’s 100% Cabernet Sauvignon from Napa, California. This is a beautiful wine.

Lessons from a Family Business

I worked for my father's company, which was a family business. My dad is one of the most successful people I know, but he’s also one of the most humble. He will spend as much time with the night janitor as he will with his COO.

I want to model my life after his way of living. He has a real joy for life and has battled some hard times, including cancer. There was a drive in me to make him proud by stepping out and following in his footsteps.

The Reality of Entrepreneurship

Entrepreneurship is not for the faint of heart. Some days I wonder why I got out of a stable job where I was making great money. You don't know how to run a business until you practice it, and I’ve made so many mistakes with manufacturers and marketing.

If I knew then what I know now, I’d be ten times farther along. That’s why many entrepreneurs succeed on their second or third business; the first is a training ground. I’m doing the packing and shipping myself. There’s no one else to pass work to.

Future Innovations and Technology

I’m looking at the AI revolution now and how that could revolutionize service-based businesses, especially healthcare. I have a friend who does technology for the PGA, and we’ve been talking about developing something in that space.

Technology has shortened the time between having an idea and figuring out if it’s good. We used a 3D printer in 2020 to print prototypes and end caps. It was so loud it would hum through the building at night, but it saved us thousands of dollars.

Getting the rights to sports entities is costly, but you look at the value they bring. Recently, A.J. Brown of the Philadelphia Eagles was on the bench reading a book. That book went from number 500,000 on Amazon to number one overnight.

The NFL charges huge rates for those logos, but you look no further than that for the value of being associated with a property. Stu, this was absolutely fabulous. We really want to thank you for being on the show. We will see you next time.