Craig Weiss | Leading a Billion-Dollar Unicorn, Starting a Business with Your Best Friend, and How to Raise Money in a Global Pandemic

Craig Weiss is the Co-founder and CEO of Retainer Club and Mouthguard Club. He is a serial entrepreneur who has founded or co-founded half a dozen companies. During his three and a half years as President and CEO of NJOY Inc., Craig generated over $150 million in revenue, raised $200 million in equity financing, and which he got from a $10 million pre-money valuation that reached over a billion dollar valuation in 2014. He recruited and scaled to 130 employees across half a dozen different countries, manufactured and distributed over 80 million units of the company’s products, and achieved distribution in over 130,000 locations worldwide including Walmart and Walgreens.

Before NJOY, Craig practiced law as a U.S. Registered Patent Attorney where he focused on the drafting and prosecution of patent applications for medical device, ecommerce, and business method inventions. Craig has eleven patents to his own name, including five for medical devices. He earned his law degree from Arizona State University and his bachelor’s degree from the University of Pennsylvania. He is a resident of Arizona and is married with two children.
In this episode of the Smart Business Revolution Podcast, John Corcoran sits down with Craig Weiss, Co-founder and CEO of Retainer Club and Mouthguard Club, to talk about how Craig and his business partner invented 3D-printed retainers and their business’ subscription model. Craig shares his strategies for successfully raising funds during the COVID-19 pandemic and the challenges that they faced in trying to bring orthodontists onboard their business.

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Here’s a Glimpse of What You’ll Hear:

  • Craig Weiss talks about his friendship with Dr. Blair Feldman and their decision to start a business together.
  • Why Craig and Dr. Feldman works well together at Retainer Club and Mouthguard Club.
  • How Craig was able to raise funds for the businesses during the COVID-19 pandemic.
  • How Craig articulated and presented his orthodontic product in the early days of the company.
  • The limitations found in other retainers and mouthguards in the market that their product addresses.
  • The challenges Craig faced when explaining the idea of the Retainer Club to orthodontists and how he found his breakthrough.

Resources Mentioned:

Sponsor: Rise25

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Episode Transcript

Intro  0:14  

Welcome to the revolution, the Smart Business Revolution Podcast, where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran  0:40  

All right. Hey, welcome everyone. John Corcoran here. I’m the host of this show. And you guys know my story. But I’m a recovering political hack, recovering lawyer spent many years working in politics, including as a speechwriter were stints in the Clinton White House for a California Governor. White House has kind of been in the news these days. I don’t know if you guys have tuned in at all.  I spent years practicing law in Silicon Valley. Much like my guest here I’m also a former attorney recovering attorney like myself. And 10 years ago, I discovered this medium podcasting, which we’re doing a live episode right now. And I’ve been doing it ever since one of the best tools ever for connecting with smart people. Again, we have great conversations with top CEOs, founders and entrepreneurs of all kinds of different companies. And today, I’m also the co-founder of Rise25, where we help b2b businesses with the strategy and the production they need to create a podcast that produces tremendous ROI and connects them with their ideal prospects and referral partners. 

And before I introduce today’s guest, I want to give a big shout out to Dr. Dustin Burleson. Go check out Burleson Seminars, they do some interesting stuff and also Will Ventures will a VC firm out of bosses that Boston that invests in sports related investments, which will come up in the course of this interview, because my guest today is Craig Weiss. He is the Co-founder and CEO of Retainer Club and Mouthguard Club. He is a serial entrepreneur who has founded or co-founded half a dozen companies. During his three and a half years as president and CEO of NJOY Inc., Craig generated over $150 million in revenue raised $200 million in equity financing, and actually got it from a $10 million pre money valuation reaching to over a billion dollar valuation in 2014 recruited and scaled to 130 employees across a half a dozen different countries manufactured and distributed over 80 million units of the company’s products, and achieved distribution in over 130,000 locations worldwide including Walmart and Walgreens. 

So he’s got an amazing story. And we’re gonna dive into it here. As you know, this episode is brought to you by Rise25 where we help b2b businesses to your clients referrals and strategic partnerships with done for you podcasts and content marketing. You can learn more at All right, Craig. So you’ve got this great background in entrepreneurship. And then you and your buddy Blair, you guys have been friends for a long time. And you have talked about different business ideas over the years, I love this story. And finally had a chance to do a business together from an idea that Blair had who had been a practicing orthodontist for many years. So tell us the story of how that came about.

Craig Weiss  3:10  

Yeah, I mean, you know, Blair, and I have been, you know, sort of best friends for almost 20 years. And he had a really a front row seat for my crazy, you know, enjoy story, which I had been a patent attorney for a decade, and then sort of much like that, that Kafka story metamorphosis, where the, the author wakes up one day and discovers that he’s a cockroach. I, I, I sort of, you know, woke up one day and realized that I was an entrepreneur. And so I left behind the practice of law. And I had this crazy wild run of sort of running this company up to this, you know, unicorn status. And, and Blair, I used to always joke was an entrepreneur trapped in the body of an orthodontist. You know, he just had a great kind of mind for business. And so about, gosh, five or so years ago, he said, Hey, listen, I got a, I want to run this idea by you. And, and I’m like, you know, hey, sure, shoot. And he said, Well, you know, when you when you, you know, he’s like, Look, I’m an orthodontist, when you finish getting your braces, you know, your Invisalign treatment, your teeth are perfectly straight. He said, you know, the standard of care is you’re supposed to wear a retainer, when you sleep at night, you know, for the rest of your life. And if you don’t, your teeth are going to move on. And it’s just going to undo all this expensive time consuming orthodontic treatment. And so he said, Well, look, as a practical matter, no one wears their retainer at night for the rest of their life. That thing gets old, they break it, they lose it, you know, the dog eats it. And he said, So look, My idea is like Dollar Shave Club for Retainer Club, brand new retainer shows up in the mail, you throw away the old one, you pop in the new one, like 99 bucks, you know, once a year, and I go, Wow, I think that’s a great idea. He’s a keen eye. There’s just no subscription model like in the whole field of orthodonture. And so we just started talking about it and I started asking a few questions and Okay, well, you know, how much does it cost? It’s like, Oh, well, we’ve got these new technologies and 3d printing and 3d scanning. And, and the more questions I asked, the more I realized, like, this is like $100 million business. And so I start, you know, making suggestions and asking questions. And he was like, Look, I’ve had this idea for two years, I haven’t done anything with it, like, what do you say we partner 5050. And I’m like, so let’s do it. So, you know, I think when you go into business with your best friend, it’s, it’s either gonna be kind of spectacular, or a catastrophe. I’m happy, I’m happy to report it’s been quite spectacular, probably even better than I had hoped it would be.

John Corcoran  5:40  

So let’s say you guys still continue to get along really? Well. I see you banter with one another? And did you hesitate at first, were you kind of like, you know, I don’t want to ruin a great relationship.

Craig Weiss  5:50  

You know, it’s funny, I really don’t remember being worried or nervous or scared or thinking like, ooh, I got some Heebie Jeebies about it. Like, I think part of it is we’ve just known each other for so long. And I think we, you know, knew each other so well. And also, we have a very similar kind of philosophy on life, we have a similar worldview, we have a similar way of, of, you know, we have a tremendous amount of mutual respect for each other. That obviously helps. And I think we also, I mean, the other kind of key is we really, I don’t want to say we stay in our lanes, because that makes it sound like, you know, like one of us says to the other Oh, hey, I’m the expert here. It’s not like that. It’s more that I, you know, he’s the subject matter expert, the guy’s a 20 year orthodontist. He’s, you know, was the team orthodontist for the Phoenix Suns in the Arizona Diamondbacks. For three years. He’s, you know, member of the acat, you know, Academy of sports dentistry. And, you know, he was for eight years, the, as an adjunct professor of, you know, orthodontics, you know, he really knows his stuff. And, and I love that, and I think that’s great. And I think he looks at me and says, Okay, here’s a guy who built a billion dollar consumer company and raised, you know, a couple 100 million dollars in private equity. You know, I don’t think he needs me to tell him, you know, how to raise money, you know, like, and so it’s been a really great partnership. In many ways, you, you are uniquely uniquely positioned to bring a lot of value to this business concept because of your background. And he is unique, given his background, to bring his expertise to this particular business idea. Totally know that the business wouldn’t exist without the two of us together. And so it’s been, it’s been great. And there’s just a tremendous, you know, I had I worked with my oldest brother to enjoy for I’d hired him as my general counsel. And, you know, there’s when you have that level of trust with somebody that I have with Blair that I had with my oldest brother, Jeff, you just, you can’t replace that. It’s just, you know, it’s Yeah, yeah, that part’s been fantastic.

John Corcoran  8:10  

Now, you wisely started it right before global pandemic, so, you know, well done on that. But what I want to ask also about raising money, because I know you raised money early, early on in this pandemic, so in April, you closed a round of funding, what was that, like a month into this global pandemic and raising money.

Craig Weiss  8:32  

So I’m still kind of shocked that we pulled it off. And, you know, it taught me a lot of valuable lessons. So one was, I still remember saying to Blair, they say we’re gonna close we’re closing on like, Monday. I’m like, I mean, I you know,

John Corcoran  8:52  

and he’s, you know, kind of he’s thinking Wait, you’re our money raising expert.

Craig Weiss  8:55  

Right? You know, I’m still kind of surprised by it. First of all, I give a tremendous amount of credit to Will Ventures, the VC themselves, they’re young and super smart for former D one athletes who all went to Harvard. The main founder, Isaiah is just a superstar. He and when I say superstar, I mean, I hate to, I hate to say things like that, but when I finish my short description of him, we’re all gonna feel a little worse about ourselves. But this is a guy who was pre med at Harvard, got his MBA at Harvard sandwiched between his eight years in the NFL, but he’s, you know, when I first described him to Blair, his immediate response was underachiever. And this is a guy who grew up in such abject poverty that he was the subject of an Oprah Winfrey, like Emmy nominee epic, Emmy nominated show about overcoming poverty. So yeah, no, just a spectacular guy. And so, so yes, I give them A lot of credit for not letting the pandemic change their level of confidence and enthusiasm and what Blair and I were doing. And, and so but also, it goes to, you know, something that, you know, my mentor, le wartman used to always say to me, which is, you know, investors invest in one thing, which is growth, and you’ve got to have a growth story, it doesn’t have to be a revenue growth story, or a profitability growth story. It could be a customer acquisition growth story, it could be, you know, a market penetration growth story, but you’ve got to have a growth story that can get people, you know, excited. And I think we had one, and that was sort of the key to that race.

John Corcoran  10:45  

And one of the interesting things about your business is it took me a little while to wrap my head around it, because on the one hand, it’s kind of a simple idea, right? It’s 3d printed retainers on a subscription model. Okay, that makes sense. But there’s a couple of benefits to it, and there, and it even took you guys a little while to kind of figure out those benefits and how to package it and sell it and who you should be selling it to, and the most high leverage way of selling it. So talk a little bit about that, and how you figured out a way to articulate and explain it, not just to investors investing in it, but also to the orthodontist that you partner with and the end consumer.

Craig Weiss  11:28  

So, you know, look, it’s I’m really glad you asked the question, because I found a couple of really interesting things about that. So first of all, we’re still, you know, five years in, we’re still learning about our own business. And, and I and I would say our business model continues to evolve, and it continues to change. And I often say to Blair, I learn more about our business every time I explain our business to someone else, because as I’m trying to articulate or frame some aspect of our value proposition, like the light bulb goes off. And also I think, so look, ultimately, we’re kind of a B to B to C company on the Retainer Club side of the business meaning, yeah, we can try to go direct to consumer and go out into the world and say, Hey, so we’re in your retainer, doggy retainer, do you ever have orthodontic treatment, you know, $99 retainers. But the reality is, there’s like 12,000 orthodontists in the United States, you know, the average orthodontist is, you know, completing about, you know, call it 300 cases a year. And, you know, it’d be a lot easier to partner with them. They’re the gatekeepers of our target customer. And so really, in many ways, orthodontists are our customer, because if we partner with them, then they they say to their patients, these you know, every single day, someone comes into their office to complete, you know, two years of orthodontic treatment, and they could say, congratulations, you completed treatment, your teeth look great. You know, we recommend nightly retainers where for life to, in order to, to make sure that you take the results of this incredible treatment and maintain them, you know, with straight teeth for life. That’s why we’ve partnered with Retainer Club and, you know, here’s this iPad, sign up for a Retainer Club today, it’s a free initial trial. So the first set, you know, free, and you know, but you’re going to want to continue the subscription going forward. So even aspects of what I just said, was not how we started in the beginning, we beta tested for a year with Blair’s own patients, and he would just sell a $99, you know, subscription at the end of treatment. And, and so then we said, okay, let’s maybe do a free trial and make it kind of a no brainer. And, and we’re still having discussions about other ways to do the business. Mm hmm. And, and that’s, that’s on the Retainer Club side, there’s still the Mouthguard Club side, which is really a totally different deal.

John Corcoran  13:59  

And that is it’s kind of similar product, right? Except that you can customize it and you can have team logos and things like that.

Craig Weiss  14:08  

It’s, in some ways, a very different business. You know, even though the tech, the underlying technology is very similar, which is, it’s basically the 3d scanning, which is, you know, when we were kids, the way that they they figured out how to measure your teeth was with that horrible glue, that you know, that should they

John Corcoran  14:27  

are using this mouth guard into boiling hot water. Yeah, take it off and then stick this boiling hot device into your mouth and clamp down on it.

Craig Weiss  14:37  

Yes, that’s funny. So both of those experiences, whether it’s the glue that you gag on, which is like the worst experience that anybody’s ever

John Corcoran  14:45  

had, and never and never did the glue and never

Craig Weiss  14:47  

do is horrible, but the boil and bite, as it’s called, is like the most ridiculous consumer fitting process ever. You know, you take this boiling hot piece of plastic and jam it into your And it doesn’t even work right, it doesn’t even fit well afterwards. So now we’ve got this like, you know, incredible $30,000 you know, basically non invasive scanner that scans your teeth. And then we have this incredible high resolution 3d image of your teeth. And based on that scan, we can 3d print a model of your teeth, and then make either retainers if you want to wear retainers or a mouth guard and on the mouth guard side, which look there’s 40 million mouth guard soldiers in the US every year anybody who plays context, sports should be wearing a mouth guard, but you’re required to wear it for football and for hockey and lacrosse. And, and you’re wrestling and a bunch of sports and so but what’s cool is on the mouthguard side, unlike maybe a clear, you know, retainer, you can trick them out. So you can do any color, any logo, any design, your jersey number, your name, whatever you want. It’s kind of like the sky’s the limit. And we spend a lot of time developing what we think is like a super awesome mouthguard designer, which we just actually just launched. Like yesterday on our website. I think it’s that mouthguard slash personalize. And, you know, and it’s just super cool. Like we think in particular kids but even grown ups will have a ton of fun kind of tricking out their mouth guard.

John Corcoran  16:18  

That’s pretty cool. And and so on the going back to the Retainer Club side, when you were first explaining the idea to orthodontists Did you find it was a challenge?

Craig Weiss  16:32  

Yeah, there was definitely a challenge, because so there’s a bunch of interesting challenges, you know, so first of all part of having Blair as my business partner. It’s so critical, because he is our target customer. He is an orthodontist. He did this for 20 years. He knows his people, and he knows their pain. And he can relate to them. And he understands them. And, you know, one of the things that he said to me, it’s how the business got started, is he said, Look, you know, there’s this interesting dynamic, which is that dentists get like a lifelong relationship with their patients. And he says, as an orthodontist, I only get a two year relationship with my patient. He said, Now, it’s actually a great two years. And if anything, it ends on a high note, like people come in their teeth are all crooked. And then two years later, they walk out the door with this incredible, beautiful smile, and they couldn’t be happier. And he said, 95% of the time, though, I never see them again. And he said, and in the 5% of the time that I do see them again, it’s not a wonderful relationship. their teeth have moved, they’re frustrated, they come back in How can my teeth move? And he goes, and then I go from basically being an orthodontist to like a private detective. Well, have you been wearing your retainer? Why didn’t you call us? How can we didn’t come in, you know, and he said, the relationship becomes really kind of adversarial. And he said, I just, I just hate that. And so Retainer Club was really born out of that frustration of how can we how can we sort of get out of that, that dynamic, but but there was another issue too, which we learned over time, which is, you know, one of the smart people that I got to work with when I was at enjoy is kind of a brilliant marketing guy. In fact, if anyone watched ‘Madman’ he liked was He’s like, right out of madman, he had his own creative marketing agency on Madison Avenue in New York. I mean, he really was like, bred out of Central Casting. And so we had this meeting with him in New York. And he took a look at our box that we ship our retainers in. And he said something that I just thought was so profound, you know, when you We live in a digital world, and we do all of this digital advertising, and we you know, you send emails, and you send texts, and we all know what, you know, the open rate of an email that, you know, advertisements, you know, whatever, 2% 3%, it’s a, it’s a low single digit number. And he starts looking at this box, and he goes, you know, you guys have a 100%, open rate. Like, everyone’s gonna open this thing. It’s got their custom fitting retainer in it, and you start to think, yeah, I mean, what’s the open rate on an Amazon package? Right, it’s probably pretty darn close to 100%. And so he started to realize like, okay, you know, there’s a great opportunity here for marketing. And so we started to promote to our partners the ability to market their services, like a refer friend program, or a teeth whitening program inside our package that has this 100% open rate. And, you know, we didn’t have that idea. When we started the business. It was something that got developed over time as we’ve iterated, and we’re pitching our orthodontists on, hey, we want to increase the lifetime value of your patients who currently only have two years and you never see them again. Now you can extend that out, you know, really forever,

John Corcoran  19:53  

Right. That’s brilliant. Yeah. Craig, this has been really interesting and insightful. Where can people go to learn more about you and learn More about Retainer Club and Mouthguard Club?

Craig Weiss  20:02  

Sure, so, And we’ve got partners now when Gosh, maybe a dozen or more states, maybe closing in on 15 states. So check us out and you can look at our little locator to see where you can go to get a scan that takes about three or four minutes and then you’re off to the races and then where like I said, we’ve got that kind of cool new designer, which you can play with and trick out your designs doesn’t cost anything and and then if you want to order one, it’s you know, we got your scan and you know, again, you can do mouth guards or retainers, so that’s probably the best place and on terms of contact information just you know, [email protected] or [email protected]. All right, Craig, thanks so much.

Craig Weiss  20:48  

My pleasure. Thank you, John. Really appreciate it.

Outro  20:50  

Thank you for listening to the Smart Business Revolution Podcast with John Corcoran. Find out more at And while you’re there, sign up for our email list and join the revolution. And be listening for the next episode of the Smart Business Revolution Podcast.