How This Vending Machine Entrepreneur Followed a By-the-Books Approach to Growth

“A lot of vendors out there operate on handshakes; they think it’s really cool not to have a contract. I’m not one of those people.”

Aug 31, 2021 · 8 min read
Dan and Tricia are two employees at Wicked Healthy Vending.

When a vending machine eats your dollar, Tina Paine is the person who comes to the rescue.

“I’m there in, like, two minutes,” jokes the owner of Wicked Healthy Vending, one of the fastest-growing healthy vending companies in Massachusetts.

The daughter of a small business owner herself, the 60-year-old got into the vending business in 2014 after a long career working in corporate compliance. Today, Wicked Healthy has nearly 50 machines across the state with a focus on providing access to healthy snacks to disadvantaged communities.

Hello Alice caught up with Paine to discuss her path to vending, how she has managed her company’s growth, and the lessons about contracts, professionalism, and business etiquette that she’s carried from her corporate life. The following conversation has been lightly edited for length and clarity.

What kind of business did your dad run?

My dad was a meat wholesaler in Everett, Mass. He passed away when I was 11, and we shared the same birthday. He used to bring us into the meat wholesale place, and I remember all the carcasses in the cold freezer and all the sawdust on the floor. We would go along with him when he was trying to make deals with restaurants — me and my little brother would eat the sugar cubes off the table while he was trying to get a contract. I remember he used to come home with all these papers. I would jump down the stairs to greet him and ask if I could play with his adding machine and pretend like I was working for the business. I loved it!

Vending machines are everywhere, but most people rarely notice them. What did you know about the industry before you started Wicked Healthy?

I didn’t know anything about the industry! It’s not like I wanted to be like, ‘Oh geez, I always wanted to be a vending lady!’ I just knew I wanted my own business. When I was searching for an idea, I found a company called Naturals2Go. That gave me a jumpstart. I bought my initial machines from them, and they supported me with training and teaching me about the business. From there, I expanded and located machines on my own. That guidance into the industry was great before I jumped into it.

How exactly does your business work?

I started with five machines at the end of 2013, and I was working a corporate job all the way to the end of 2018. Then I decided to focus on the business full time. I’m currently growing by about eight machines a year, although the pandemic set me back a bit. Today I have about 46 machines.

I have two employees and a warehouse. Each employee is assigned their own van, and they primarily fill the vending machines. My husband recently retired, so he’s helping out. There’s a lot of shopping involved, a lot of purchasing, and a lot of putting away stock. As for me, I run the business, I grow the business, and I reach out to the community. Starting in July, we’re starting to see a lot more interest again, so we have new locations coming up.

Tina Paine and her husband, John.

Was this a turnkey operation, or did you have to figure everything out with stocking, deliveries, etc.?

Naturals2Go sold me an initial five machines with the credit card readers, and they had a three-day training explaining everything. You would play with the machine and learn what to do, but after that, I was on my own to grow the business and stock the machines. I actually had one machine delivered to my house so I could mess with it. At first, we went to Costco and Sam’s Club and Walmart, and we were experimenting with all the snacks. I pretty much learned on the fly as I went along.

How quickly did you bring on employees when you started a business?

When I got to about 16 machines, I got my nephew to help. He was in his early 20s, and he hadn’t found his career. It helped him, and it helped me to handle filling machines, going to the bank, going shopping. Then he left for his real job, and I hired Dan, who is the husband of a woman from my corporate job. When it got to about 32 machines, I was looking to leave my office job because the business was getting to be too much. That’s when I hired Tricia, who I found through my local Facebook community group. The hours are great for working moms or working dads because it’s all in the morning. You do your vending, you’re done by 1 or 2 p.m., and pick up the kids. Tricia’s been working out great.

Wow, it sounds like you’ve had great hiring experiences!

I’ve been very, very lucky! Thankfully, I have my big Italian family to fall back on. My other nephew — he’s in his 30s — is actually helping me shop right now.

Some might be under the impression that a vending machine is a vending machine — that they’re interchangeable. But your entire business is about countering that notion, right?

Oh, absolutely! We’re a value-added partner. This is just more than providing one vending machine. It’s a lot about community, too. I try to go into disadvantaged communities that want to have me in their location, so I can get healthier options for them. We have some YMCAs that are more financially disadvantaged, and that’s where I try to get involved. It’s really important to me to feature woman-made products in my machines, too. I kind of want to start a Women in Vending group!

Interesting! Have there been obstacles as a woman in this industry?

Yes, definitely. Typically, this is an old boys’ club type of business. A lot of the vendors that have been established for years are still out there. I joined a local vending association, and the whole board is men. I can’t seem to get any communication from them. However, the tides are turning because a lot of the decision-makers out there are women, and a lot of locations are looking for healthier options. Some of the old vendors are throwing in a couple of Baked Lays in their machines and calling themselves healthy, but I don’t think that’s going to fly. Companies and organizations are really moving to healthier options for their employees or customers or clients, and they’re going to be seeking out the ones that are truly committed. They’re going to look for somebody like me.

What were some of the big lessons you learned as a first-time business owner?

The actual vending business is a really simple concept, but it’s hard work. The biggest thing I learned is that when someone wants my services, I need to ask the correct questions to make sure that the location is profitable for me. Initially, when I heard a potential location had 100 employees on-site, I was jumping at the opportunity. But that could be a slow location! For example, I had a gas company where 100 employees were all drivers, which means they were out all day and not buying snacks. That more sophisticated understanding means that I have to turn some customers down. That’s a big shift. In the beginning, I didn’t want to say ‘no.’

What lessons did you bring from the corporate world that have helped you with your business?

Everything you do in life is a lesson for later. I was a senior manager in regulatory in the mutual fund industry, and I have a lot of background in legal compliance. That means contracts. The thing is, a lot of vendors out there operate on handshakes; they think it’s really cool not to have a contract. I’m not one of those people.

Being able to do a contract, just having the wherewithal to be professional in my writing and my business plans — it’s definitely helped. Even though I have two employees, we have staff meetings. I try to run things the way I would if we were a business of 100 people. We’re a small group, and we’re like family, but at the same time, I tried to put structure around it. That’s legitimized me and given me business; I differentiate myself a little bit maybe because of that structure.

You’ve said that your advice to other entrepreneurs is to not isolate yourself. What inspired that comment?

When I worked in the corporate world, you could talk to someone over the cube. You’re chatting about this idea you had, or you don’t agree with your boss or something. Whatever it is, you can talk to somebody about it. But now, I’m by myself, and I’m working 15 million hours a day. I realized that I felt alone in a way. So, what do I need to do? I joined the chamber and the WBENC. I started to go take some classes. I was feeling like I was on an island, but it was my own island. Now I really feel better. I want to be around other entrepreneurs to share ideas, and I want to be around other women supporting women. Really, I wanted to grow as an entrepreneur, because you’re not gonna learn everything by yourself. That’s why it was important to me.

You’ve ironed out a lot of the kinks with your business over the years. What challenges are you still working on?

I have a lot of growth opportunities that are out there, and that’s actually a challenge because I don’t know what I’m dealing with yet. I don’t know if I’m going to need 20 machines or 100 machines. It’s going to be challenging to get that other employee scheduled in while also trying to be efficient and not have to buy an additional vehicle.

And this is silly, but if you’d asked me what I dislike about what I do, I would have to say the nature of the business. Every so often, I’ll get a call at 7 o’clock at night from somebody whose dollar is stuck in the machine because it’s jammed or pennies were put in the machine. It’s not like back in the day where we can just be like, ‘Write to us, and we’ll send the money!’ I’m there in, like, two minutes.

It’s so funny that after all these years and with high-tech machines the dollars still get stuck!

Oh, absolutely! The more high-tech something is, the more sensitive it is. One thing is off just a little bit, and everything will shut down. But that’s just the nature of the business, and every business has its thing.

Anything else you’d like to share about your business journey?

I’m glad I did it, and it challenges me every day. Like, I’m doing pitch competitions, and I become a nervous wreck before I do one. But every time I do it, it challenges me to be better and more confident. The business has definitely helped me in a lot of ways that staying with my corporate job would never have.

Also, I’m 60, and I can still see 10 years to my horizon with the company. I’m not sure if I want to sell it to family or one of my employees, or maybe just kind of step back into a higher role. My daughter’s looking to have her first child, so that will come into play as well. I’m mostly trying to balance time. Somebody saw me working so much and gave me some advice: ‘Stop being a crappy boss to yourself.’ That was a lesson that stuck with me. I’m not going to be a crappy boss to myself!

Do you have your own questions for Tina? Click the “Introduce Me!” button on her Hello Alice profile to connect directly today.