Episode 1: How to Reinvent Your Business

Featured Guest: Ray Wayman, Founder & Owner - JR Boutique

In order to survive, every small business has to be nimble. Successful entrepreneurs understand change and reinvention are a natural part of running a business. John Henry speaks with two seasoned entrepreneurs to find out the lessons learned when faced with external pressures which forced them to pivot and rethink their business strategies.

I feel like this competitor keeps forcing me to kick myself in the butt. And I don’t like it. But it’s made me a better entrepreneur.                   - Betsy Helmuth

Successful entrepreneurs understand the need to evolve in order to stay relevant. Theoretically, that concept is easy to accept, but in practice, it’s much harder to follow. While reinvention can happen organically, more often than not it’s sprung on businesses by outside forces they can’t control. For Debbie Harrison’s family, it was the changing seasons. For Betsy Helmuth, it was a flashy new competitor and for Ray Wayman, it was an unforeseen roadblock.

In the first episode of season two of Open for Business, host John Henry tries to get to the root of what lies behind successful reinvention. John speaks with Betsy Helmuth, founder of Affordable Interior Design, who evolved her business after a new competitor forced her to double down and embark on a critical journey of self-discovery. He also connects with Ray Wayman, owner of JR Boutique, who figured out how to keep his doors open after a conflict of interest left him unable to sell any of his inventory.

Follow along as John uses these stories of real-life entrepreneurs to share five key takeaways that will help any business through successful reinvention.

Previous Next Betsy Helmuths Affordable Interior Design Headshot Updated Affordable Interior Design Office Home 18 crop Updated Affordable Interior Design Office Home 2 DSC 0123 DSC 0125 DSC 131 DSC 0131 DSC 136 Debbie Marriott Harrison crop First Hot Shoppe 1927

Your Guest

Ray Wayman

Founder & Owner - JR Boutique

According to Ray Wayman, his business started with “…300 bucks, a stolen idea and a dream!”  A longtime member of the law enforcement community, Ray was one day showing off a newly purchased retractable ID holder to his colleagues.  Several colleagues admired his purchase and asked how they could get their hands on one.

That’s when the light bulb came on.

Ray worked with the original seller to purchase several more to sell them for a profit. Then, using a $300 tax return as seed money, Ray launched JR Boutique.  JR Boutique offers various products marketed to the law enforcement, military, firefighter, and Emergency Medical Services communities. Since selling that first retractable ID holder in 2004 Ray has expanded, offering nearly 600 products, some of which he has designed and produced himself.  Though JR Boutique is still Ray’s side business, he’s currently running an experiment to see if he’s able to save a year’s salary and pursue JR Boutique full-time.

Visit the JR Boutique Store

Episode Transcript

JOHN HENRY: Hey! I’m John Henry and this is Open for Business, a branded podcast from eBay and Gimlet Creative about building a business from the ground up.

JOHN HENRY: Hey! I’m John Henry and this is Open for Business, a branded podcast from eBay and Gimlet Creative about building a business from the ground up.

Welcome to the very first episode of Season 2! We’re super excited to be back and we have a great season planned for you guys.

This season, we’re going to feature stories and lessons about how to finance your business, how to kill it at customer service, how to fail at business and live to tell the story. That’s all coming up on season two of OFB. But today, we’re going to kick off this episode at a root beer stand.

DEBBIE MARRIOTT HARRISON: It was sort of a hole in the wall building, I think?

JOHN HENRY: This is Debbie Harrison. And that hole in the wall building belonged to her grandparents. In the summer of 1927, they got married and moved to Washington DC with a dream to start a business. When they got there, it was a typical hot, humid DC summer and so they decided they’d start out by selling cold, frosty mugs of root beer. That’s what they did in that hole in the wall spot.

DEBBIE MARRIOTT HARRISON: All they sold was a mug of root beer for a nickle a mug. There was just barely enough room behind the counter for a server to be there. I don’t think there was even enough room in that, inside the root beer stand to have extra tables it was so tiny.

JOHN HENRY: It sat nine people total! And that summer, those stools were almost always full. Business was going great! But as summer came to a close, Debbie’s grandparents knew they’d have to change things up. No one would want to buy an ice cold mug of root beer on a freezing winter day. Their root beer stand happened to be close to the Mexican Embassy at the time, and so one day Debbie’s grandma enlisted their neighbor’s help in expanding their menu.

DEBBIE MARRIOTT HARRISON: My grandmother who’d majored in Spanish in college and spoke fluent Spanish, went to the Mexican Embassy and knocked on the door and she charmed the chef, and he invited her in and he taught her how to make tamales and chile. And there was no kitchen in the first root beer stand so she would make the food in her apartment and walk it over every day.

JOHN HENRY: So, with help from that friendly neighbor, by the winter of 1927, the nine-stool root beer stand was transformed into a tamale and chile restaurant. Just briefly, here’s what happened next: After the tamales, Debbie’s grandparents added hamburgers and hot dogs to the menu. They named their restaurant a Hot Shoppe. They opened one Hot Shoppe after another. A few years in, they offered curb service. In 1937, they took advantage of the dawn of air travel and expanded into in-flight catering They kept growing and evolving the business for three decades, until 1957.

After 30 successful years in the restaurant business, an executive at the company had an idea, which he floated to Debbie’s grandpa one day. Instead of opening another restaurant, let’s try something totally new.

DEBBIE MARRIOTT HARRISON: Eisenhower has just built all of these freeways and everybody’s out exploring the country and people can’t wait to get in their cars with their families and go on vacations. Why don’t we take this land and build a motor hotel on this land instead and let’s try it.

JOHN HENRY: Debbie’s grandparents built their first motel in DC, right near the Pentagon. And that decision reinvented their entire business. And here’s where I tell you that Debbie Harrison has a maiden name. It’s Marriott.

DEBBIE MARRIOTT HARRISON: The nine stool rootbeer stand that my grandparents started in 1927 in Washington, DC has evolved to be the largest hotel company in the world as Marriott International.

JOHN HENRY: Today, Marriott International has about 675,000 employees and is currently valued at about $34 billion. Debbie’s grandparents, J. Willard and Alice Marriott, founded a root beer stand but they continuously evolved over the years and 30 years in, they reinvented the company completely.

JOHN HENRY: Do you ever think about the fact that someone had to actually make that decision and say we’re going to steer this whole company in another direction?

DEBBIE MARRIOTT HARRISON: : Oh, oh sure we think about that a lot. Where would we have been if we’d stayed just in the restaurant business? And um, we probably actually would be out of business. You know, you have to keep reinventing yourself or you fail.

JOHN HENRY: On today’s show: How to reinvent your business.

So, here are some other companies you may have heard of, that started out as something else completely:

American Express began as a mailing and shipping company. Shell Oil Company started out selling actual shells- like, decorative seashells. Flickr was a multiplayer gaming company when they first began. Abercrombie and Fitch sold sporting goods. Taco Bell’s first product: hamburgers! And longtime podcast listeners may know that Twitter started out as a podcasting company.

Evolution, reinvention-- whatever you want to call it-- sooner or later every successful business faces the need to change and sometimes that change has to be dramatic. As a business owner, you don’t usually get to choose when to reinvent your business and when the time comes, it can be scary and confusing. And what we know is that no matter the size of your business, Debbie Marriott Harrison is right: You have to keep reinventing yourself or you fail.

Coming up, we have stories and lessons from two very different business owners who faced this exact dilemma: reinvention or failure.


BETSY HELMUTH: Hi, how are you? Welcome.

JOHN HENRY: Thank you. I’m John.

BETSY HELMUTH: Thanks for stopping in. I’m Betsy. Good to meet you again.

JOHN HENRY: This is Betsy Helmuth, founder of Affordable Interior Design. We’re meeting her at her storefront in Dobbs Ferry New York. On the outside, her store has a bright turquoise-blue awning. It’s a pop of color on a small town main street. Inside, Betsy’s store doubles as a gallery, featuring inexpensive furniture and accessories that look modern and stylish. But before she started this business, Betsy was interning with a fancy Manhattan interior designer. She knew from the outset that-that wasn’t her thing.

BETSY HELMUTH: Spending $30,000 on a couch, waiting six years to get it, it just didn't jibe with who I am. I grew up poor. I was like, couldn't we just get that at Target? Couldn't I find something similar at Crate and Barrel?

JOHN HENRY: So, she decided to start a business. This was 12 years ago, back in 2005. And when it came time to name her business, she turned to a longtime trusted advisor...

BETSY: So, I watched a lot of CNBC and I watched Donny Deutsch- “The Big Idea with Donny Deutsch.”

“THE BIG IDEA WITH DONNY DEUTSCH”: Welcome back to “The Big Idea!” Tonight! We’ve got ideas so simple you want to slap yourself!

BETSY HELMUTH: He said something during one episode that changed my entire life. He said if your business name doesn't say exactly what you do change it tonight and um, I changed my business name that very night.

JOHN HENRY: Betsy grew Affordable Interior Design methodically. She financed it without loans or outside money and she built her client base one-by-one. She was heads down, growing her business, year after year, until:

BETSY HELMUTH: I think it was maybe about five years into my business when I saw a competitor and they seemed kind of interesting.

JOHN HENRY: This was around 2010 and the competition took Betsy off guard. Naturally, Betsy wanted to check them out. This new upstart company was having a party in Manhattan to recruit designers and Betsy decided to attend.

BETSY HELMUTH: And I was like, I need to know everything. I need to know how they're working, I need to know what their model is.

JOHN HENRY: As soon as she walked into the party, it was clear to Betsy that not only was this new company going after her exact client base, they were going after it in a big way, with a vision and a strategy and a Brian.

BETSY HELMUTH: They had a guy at a desk, I remember. I remember his name too. His name was Brian. And they were like, this guy is here. He practically sleeps in the back and all he's doing is business strategy, I was like oh shoot! We didn't have Brian like sleeping in my basement doing social media! Like they had a whole big dry erase board with their strategy. And so I was like taking notes fast and furiously like while they were presenting about paint or something. I’m like, oh my god! A hundred designers and 2,000 clients- oh my gosh! They were going after that budget client, that client who wants a really nice space but rents, or who is moving in a year. It was my exact same client which of course confirmed my worst fears. So I remember feeling like, how can I keep up? It's just me! Like, how can I compete?

JOHN HENRY: Betsy left that party pretty freaked out. But, by the time she got home, she’d made a decision. Betsy decided, that night, back in 2010, to ignore the competition. She was going to keep her eyes on her own paper, do the best possible job she could for her clients and trust that her business would keep growing. And that plan worked for a surprisingly long time. Her business grew year after year… until last year. In March of 2016, Betsy decided to take on the first major expansion in her then 11-year-old business. She hired three designers. And the very same week she brought them into the store for training, Betsy noticed that something felt different.

BETSY HELMUTH: I noticed that the phone was not ringing. And I noticed that the assistant’s just watching me watch the training and I'm like is the ringer on? And so...

PRODUCER:­ And did you actually ask her?

BETSY HELMUTH: Definitely! I literally said is the ringer on. And she said, Oh yeah it's been on all day. So I'm like, oh great! OK, let's keep going. And, on the inside I'm freaking out! Because the phones aren't ringing, and it's day after day. We had gone from being very busy and all of sudden it’s like wait! Nobody is calling me, and it was like the lights got turned off.

JOHN HENRY: The worst part was that Betsy had no idea why the phone had stopped ringing. For the first time in 11 years, Betsy had more time on her hands than she knew what to do with. So, she got in touch with an old friend and suggested they have lunch.

BETSY HELMUTH: And we were at lunch and she was like, what's going on in your business? And I said well you know I've just hired these designers and the phone is not ringing and I don't know what's going on. And she’s in the startup world, so she’s constantly thinking about that world. And she said, you know why, right? And I said, no I have no idea why. And she said well your biggest competitor got a $20 million cash investment. And I was like, what did you say? I remember exactly where I was. We were at a Korean restaurant. It was super loud. It was really tiny. It was in Midtown and I was like oh oh oh what what what? What did you say?

My stomach literally dropped. I’m sure I went white as a ghost. I wasn’t even sure I’d heard her correctly and I wasn’t sure she even knew who my biggest competition was. It’s not like we talked about it a lot. So I said, who are you talking about? And she said, well, Homepolish.

JOHN HENRY: Homepolish. These were the same folks who threw that party in Manhattan back in 2010, with the white board and the strategy and the Brian. And Betsy had the same impulse she’d had the first time when she heard about them. She wanted to keep ignoring the competition. Until that friend-- her name is Donna-- set Betsy straight, right there and then.

BETSY HELMUTH: Do you know what I brought up to her? This was so depressing! I said well Donna it’s ok because my clients are very happy. I’ve got this model down to a science. And she said, Betsy nobody cares. It, it was terrifying!

JOHN HENRY: Terrifying because this time, Betsy couldn’t keep doing what she’d been doing up until that point. She had to reinvent her business or she’d fail.

What she did next, right after the break.


JOHN HENRY: When we left Betsy Helmuth, she was sitting in a busy Korean restaurant in midtown Manhattan, shellshocked after having learned that her closest competitor had raised $20 million. And she’d already felt the effects! For the first time in her 11 years running her company, business was dead. Before she left that restaurant, her friend Donna, the one who broke the news, told Betsy that she was willing to help. Donna wasn’t just in the startup world, she happened to be a business strategist. So, they set up a meeting at Donna’s apartment. And when the day came, the first order of business was to break out the dry erase markers and get to mapping.

BETSY HELMUTH: She said, let's make a map of all your competitors, of anybody in the interior your design space. Because of course in those six years while I've had my head down, there have been tons of small companies that have come up. It's not just me and one competitor now. It's me and 12 competitors. And, she actually mapped them all out in a really big list and there were people I didn't even know about. And she was like, no. Now you are a ninja! And you must know all your competitors and you must know what they're good at and what they're bad at. And you must know them in and out. She's like no more looking at your own paper. It's time to look up.

JOHN HENRY: This is lesson number one when you’re reinventing your business: adjust for what’s called the “hidden competition curve.” It’s common for the competitive landscape around your business to shift completely while you’re busy building your business. And you need to know that competitive landscape in and out before you can reinvent your business to fit in it.

BETSY HELMUTH: I am mid-range now. Now when people hear affordable interior design they have expectations that it's going to be, like, 50 bucks. Like, I used to be low and low: low tech low price. You couldn't get better than me. And now I'm like, I'm no longer Affordable Interior Design. What does that freakin’ mean?

JOHN HENRY: Lesson number two: When you reinvent, you must also redefine your business. Be honest with yourself about your place in that new, competitive landscape.

BETSY HELMUTH: Creating a picture of the entire landscape gave me a clear vision that there's room for me. I saw this big hole in the middle, and I was like oh yeah that's where I fit and, and my competitor isn't there.

JOHN HENRY: This brings us to lesson number three: When reinventing your business, you also have to find and reach new customers. For Betsy, this meant going after a new clientele. She’d always had the young, transient city dwellers who just wanted a nice place to have a cocktail party. Now, she’d also have to get the homeowners who want a beautiful home to raise a family in.

BETSY HELMUTH: I need somebody who wants the perfect thing. Who is that person? That's a mom who has kids, and who has clutter, and who can't see straight. People with problems want to pay for the right solution. They don't want to hire four cheap people. They want to hire one right person, even if that means paying a little bit more.

JOHN HENRY: So, Betsy surveyed the competition and went after a new client base but she also looked internally at what set her apart as a business owner. That’s lesson number four.

What’s your USP, or “unique selling proposition”? Basically, all that means is: What do you have that other people don’t? Betsy is a pro at building her brand beyond just her paying customers...

BETSY: What have I got that $20 million can’t buy? Oh god! And the answer is not much! But one thing is I do a ton of content. I already have a weekly podcast that I was just doing for fun. But, how can I turn content into cash? How can I turn content into visibility? Like I'm holding a master class. So, how can I turn content into clients?

JOHN HENRY: The main thing Betsy’s doing differently now is that she’s working on the business, not in it. The competition forced her to reinvent her business but it also helped her discover who she is now as an entrepreneur.

BETSY HELMUTH: I no longer feel misplaced in the landscape of interior design. I know where I am. I know who I am.

I don't want to say this out loud, but I'm really glad that I got a competitor. Eck! God! I just said that out loud. Because it upleveled me. You know, before I was just working for myself. I saw they wanted 100 more designers, I'm like I need some more designers. I need to be able to take time and focus on the larger picture. I feel like this competitor keeps forcing me to like kick myself in the butt. And I don't like it. But, it's made me a better entrepreneur.

JOHN HENRY: Sometimes you have to reinvent your business because you get a competitor. Sometimes you have to reinvent your business because armed federal agents tell you to. That’s what happened to .

RAY WAYMAN: I’m Ray Wayman, owner of JR Boutique.

JOHN: Ray lives in Rouses Point, New York-- just on the U.S. side of the American-Canadian border. He’s been selling on eBay since 2004 and he’s also had a day job that whole time, with an American law enforcement agency. He doesn’t want us to say which one. Working at that agency is how Ray got the idea to sell one very specific product: retractable ID holders branded with the logo of the agency where he works.

RAY WAYMAN: Law enforcement officers, most of them have a lot pride in their uniform. Many of them come from the military and they like to look sharp. It’s a matter of respect.

JOHN HENRY: If you’ve ever had a badge you have to swipe or tap to get into work, you’ve seen these things. They clip onto your belt, and allow you to zip out your badge really quickly. Ray’s specialty is that little plastic guy that your badge pulls out from, the ID holder. And he started selling them because he wanted a better looking one. One that had the logo of his agency on it. And so, he found one on eBay and when he wore it to work, all his co-workers and the law enforcement officers, they wanted one, too. He realized that his colleagues were a market, a market of law enforcement employees who wanted their retractable ID holders to look cooler. And so, just like that, Ray started selling tons of these things at work. His unnamed law enforcement agency is gigantic and so he sold thousands of them. And, he not only sold them, he designed them, matching the logo perfectly to his badge, playing with the metallic colors, making them sturdier. He loved the work. It was a creative outlet for him.

Soon, he opened his eBay store. And between 2004 and 2010, selling ID holders to his colleagues at his day job became Ray’s side business. And that business was booming! Until one day, in July of 2010, when Ray checked his email.

RAY WAYMAN: I got this email at work at my work email address and it said please call me at your earliest convenience and it gave a signature of agent so and so. I’m like, hmm, I wonder why they want to talk to me. So, I called them and he said we want to come talk to you at your address about an issue.

Could you tell me what the issue is?

No, you’ll find out when we get there.

I said, well, do I need any sort of legal representation to be with me?

Well, you’re welcome to have it if you think you need it but-- I says, well, I don’t really know if I need it or not because I don’t know what the subject of the conversation is going to be.

They came and we met in a conference room. Two armed agents in suits, just like you see on TV. They had a suit and tie on with their firearm on their side. And then they immediately handed me this letter. And we want to know who your suppliers are. We want to know everything about your business.

JOHN HENRY: Remember, Ray is selling retractable ID holders. The stuff he was selling was all over the internet. Why would they care who his suppliers are?

RAY WAYMAN: And then that’s when it came up that you know, well, you’re supposed to be an authorized vendor and we can’t enter into a contract with you because you work for us.

JOHN HENRY: Ray’s business posed a conflict of interest. He couldn’t work at the federal law enforcement agency and sell to its employees at the same time. But, Ray couldn’t afford to quit that day job. So after talking with lawyers, he realized he’d have to quit his side job.

RAY WAYMAN: I felt like a small child that had just done something wrong and I was chastised by his parents. I’ve worked so hard to be here and now you’re taking it away from me.

JOHN HENRY: That very same day, in July of 2010, when the agents told him he had to shut down his business, Ray received a $5,000 shipment of ID holders. All in, he had $20,000 dollars of inventory sitting in his basement. A ton of money for Ray! He wouldn’t be able to sell any of it.

RAY WAYMAN: Half my business-- that was half, maybe even more than half my business-- and I was just devastated. I didn’t know what I was going to do next.

JOHN HENRY: One by one, Ray took down his listings from is eBay store and his own site, and then he got really depressed.

RAY WAYMAN: And I just went through this period of kind of like mourning, not really having a desire to expand or do anything new at all. It was a terrible feeling.

JOHN HENRY: That depression lasted almost two years. Ray would occasionally go down to the basement and visit that $20,000 of unsellable inventory, just sitting down there. And it wasn’t just the money. He loved designing the products and growing the business. All of that was gone in one day. So Ray spent those years going to work each day feeling lost and unsure of what to do next. But he couldn’t help himself from researching the market. He’d look at other people’s eBay stores. He’d read about similar products that were coming out. And one day, after that two year rut, Ray had an epiphany!

He doesn’t remember exactly how it happened, but suddenly a simple thought popped into his head: If he couldn’t sell to his law enforcement agency, maybe he could sell to all the other ones. He realized there’s an entire market out there! Thousands of law enforcement officials and employees at other agencies across the country who might buy his stuff. Ray realized he’d defined his products too narrowly. If he expanded what he offered, and to who, maybe he could sell again?

This is lesson number 5: When reinventing your business, you have to be open to expanding what you offer, whether you’re selling a product or a service. For Ray, that meant getting into selling new products that he’d never considered.

RAY WAYMAN: I was so focused on this narrow field that I ran out of creative ideas.

JOHN HENRY: Now, Ray sells retractable ID holders to people working at law enforcement agencies all over the country. He also sells tons of other stuff: lapel pins, key chains, wallets. Over the past five years, his business has grown beyond his wildest expectations.

RAY WAYMAN: Just last year I hit officially $1 million in eBay sales. Just eBay sales.


RAY WAYMAN: Since 2004. Who’d have ever thunk I’d sell $1 million worth of items!

JOHN HENRY: His goal for 2017 is $500,000 in revenue. He thinks he can do it and if he does...

RAY WAYMAN: I’m attempting to save my entire salary from my day job this year and if I can

save my entire salary I’m putting in my notice and I’m going to work full time from home.

JOHN: Sayonara!

RAY: I never dreamed it would be possible, but I can taste it now. It can happen.

JOHN: Ray tell me something: when you, when you finally put in that notice are you turning around to those co-workers and going to sell them those retractable badge holders?

RAY WAYMAN: You’re absolutely correct. As soon as I quit, guess what I’m selling?

JOHN HENRY: Ray lost everything. He could have just retreated back to his day job, but he didn’t. He expanded his field of vision and took advantage of product opportunities that he hadn't even considered before. Now, Ray’s on a path to half a million dollars in revenue this year.

JOHN HENRY: So, to recap our lessons:

This is lesson number one: Adjust for what’s called the “hidden competition curve.” It’s common for the competitive landscape around your business to shift completely while you’re busy building your business.

Lesson number two: When you reinvent, you must also redefine your business. This may mean completely switching your company’s identity.

Lesson number three: Rethink your target customer. Whether that’s shifting from one type of customer to another, like Betsy, or broadening your customer base, like Ray.

Lesson number four: Lean in to what sets you apart as a business owner. Ask yourself, what do you have that other people don’t? You’re going to need it when you’re reinventing.

And finally, lesson number five: When you’re reinventing your business, be open to expanding the products or services you’re offering.


Thanks for listening!

To learn more, check out ebay-dot-com-slash-open-for-business.

Open for Business is a co-production of eBay and Gimlet Creative. We were produced this week by Frances Harlow, RMW, Nicole Wong, Katelyn Bogucki, Abbie Ruzicka and Grant Irving, with creative direction from Nazanin Rafsanjani. And thanks so much to Christine Driscoll. Zac Schmidt is our engineer.

Our theme song is by Vulfpeck.

And a very special thanks to the people who took time to talk with us for this episode: designer Paulina Grzechnik; Kim Shanahan, CEO of Book Bouquet; and Noa Santos, CEO of Homepolish. Noa was super gracious with his time. He wished Betsy all the best with her business.

Next week on Open for Business: How to kill it at customer service when you’re selling online. We’ll hear stories from entrepreneurs who screwed up.

KARIDA COLLINS: I just had to pick myself up and begin the process of apologizing. Apologizing to customers for things that I did do, apologizing for things that I didn't do.

JOHN HENRY: How to fix it when you have a customer service disaster. That’s coming up next week on Open for Business!

If you like Open for Business, please subscribe to us on iTunes or wherever you get your podcasts and please leave us a review to tell us why! It really helps people find our show.

I’m John Henry. Thanks so much for listening!

Read Entire Transcript