The Secrets of SinglesSwag: Jonathan Beskin’s Story of Building a Unique Subscription Business

Episode Transcription

Glenn Harper [00:00:00]:

Welcome everybody to another edition of Empowering Entrepreneurs podcast. This is Glenn Harper.

Julie Smith [00:00:04]:

Julie Smith.

Glenn Harper [00:00:04]:

What’s going on, Julie?

Julie Smith [00:00:05]:

You know, we both have coffee, but I cannot wait for cool to start and get back into the routine.

Glenn Harper [00:00:11]:

Oh, this is, summertime is is tough with kids. You never know where they’re gonna be and what they’re gonna be doing.

Julie Smith [00:00:15]:

And by the time this airs, everybody will be back into that routine and back into the swing of things, but definitely looking forward to that.

Glenn Harper [00:00:21]:

Well, that’s what we can hope for. Well, I agree. We’ve got a special guest today. It’s Jonathan Beskin, is one of the special individual. He Jonathan has found out that he wasn’t mental. He just needed to believe in himself and stop listening to the naysayers around him. He is a serial entrepreneur who has decided to feed his OCD and have multiple companies doing many different things. His businesses include, but are not limited to, Paradise delivered Molly Jacob and SinglesSwag. He has cracked the code for a scalable business model on the internet. Of course, he to share his story and provide inspiration to others to get out of their own way and be the best that they can be. Thanks, Jonathan, for being on a show.

Jonathan Beskin [00:00:55]:

Thanks for having me. Excited to be here.

Glenn Harper [00:00:58]:

hope that was a good introduction. I I could. I always have to make up my own. I can’t read one off the stock because it doesn’t sound like me.

Jonathan Beskin [00:01:04]:

It was great. Yeah. I think you covered, you you covered pretty much everything.

Glenn Harper [00:01:09]:

Awesome. Awesome. Well — Yeah. — you know, we always like to try to figure out a little bit about our guests. because the people that are listening, again, it’s, you know, it’s not where you are today, but how did you get there? Where’d you come from? How’d you get here? And, you know, I can’t I did some searching for you on the internet and I, you know, I can’t find out where you’re from. I’m gonna guess El Paso, Texas. Is that is that true?

Jonathan Beskin [00:01:31]:

Close. no. Just get a poker town, Florida.

Glenn Harper [00:01:34]:

You’re from there, Richard. You never moved.

Jonathan Beskin [00:01:37]:

no. So I was born in Oklahoma City — Uh-huh. — Oklahoma. and, I moved to South Florida, when I was 2. So my family kind of, my dad was a a metallurgical engineer and kind of was working for a a government defense contractor in Oklahoma and then pretty quickly moved. But I’ve been in South Florida pretty much my whole life.

Glenn Harper [00:02:01]:

Gotcha. So you’re local to Florida. Alright. Well, you’re just checking because you just never know where people are coming from, so that’s good. I I feel like, you know, vocal tone, you probably could’ve chose a better climate and a better more tax favorable state. Is there a reason why you chose Florida? for the messing with you.

Jonathan Beskin [00:02:17]:

Yeah. Yeah. Yeah. No. I I completely agree. And, yeah. Yeah. I if I if I had had Joseph Florida, which I didn’t. My parents said I’d probably choose Florida now. So

Glenn Harper [00:02:26]:

— Isn’t that crazy how they’re just pro business and pro, you know, individual do your thing at it’s a it’s a great environment, I think.

Jonathan Beskin [00:02:34]:

Yeah. It was a great place to be, during the pandemic. And, it it it still is. And, yeah, I enjoyed the summers, aren’t, I would say ideal from, you know, particularly this summer has been incredibly warm. A lot of thunderstorms. I have a a dog who’s incredibly scared of thunder and lightning and every noon. there’s a lot of thunder and lightning this summer. So, yeah, but, overall, be in Florida is a great place to be.

Glenn Harper [00:03:06]:

It’s funny. We, everybody in Ohio bought RVs and went to Florida during the the pandemic. Mike. And I was wondering if the people in Florida, they got our views and got the hell out of there. I don’t know. Did you did you stuck around or you got out of there?

Jonathan Beskin [00:03:18]:

for the most part, I stuck around. I do actually it’s funny you mentioned that. I do know some families and even close, neighbors that that did, kinda follow that program, but really looking to, you know, as a way to to get out of this area and just take a vacation, they they they just weren’t able to fly or weren’t able to go, and they might have had bigger. So they did. I I do know some people that did follow that program in the left Florida, on an RV, but they they they eventually came back.

Glenn Harper [00:03:48]:

Yeah. That that can’t be good for, anybody’s, situation to spend all that quality time and that closed quarter is driving across the country with a bunch of idiots. That’d be horrible. So god love them. You know, I, you know, I always like to try to research a little bit on clients or, you know, people that are we have on the shore, I guess, and and and from a all the Google tracking that we found on you, it it seems like you spend most of your time be going between Costco and the Royal Palm Yacht Club. Is that is that true?

Jonathan Beskin [00:04:16]:

No. No. It’s true at all.

Glenn Harper [00:04:19]:

This information is everywhere.

Julie Smith [00:04:20]:

Glendon not get a degree in stalking, although he’ll claim 1. Yeah.

Jonathan Beskin [00:04:25]:

Well, I I would love to to spend more time at the Royal Palm, Yacht Club I do go to a club often called the Boca Raton. He used to be called the Boca Beach Club. and I haven’t been to a Costco or even a grocery store, to be honest, in, like, over 5 years.

Glenn Harper [00:04:41]:

Wow. Do you have a you don’t have to allocate your time appropriately?

Jonathan Beskin [00:04:47]:

Yeah. Well, I use a lot of apps, for shopping and, yeah, but I I pretty much just need to bring it bring it in from the front door.

Glenn Harper [00:04:56]:

So, ultimately, when you moved to Florida, obviously, you weren’t old enough to know anything. At what point in time did you, decide that you were just gonna be a little bit different that you might, want to think about being an entrepreneur, or did you have somebody that taught you about that, or you saw somebody, or you just were going through the the basics because ultimately you ended up at Florida State And Florida Atlantic. Not sure I didn’t go to University of Florida. but you came a banker of all things. I mean, how does one choose to be a banker? That that’s a tough tough space. I why would you wanna do that? Who would influence you to be that guy?

Jonathan Beskin [00:05:30]:

Yeah. a lot of questions there. Well, I guess I’ll take the banking 1 first. it’s it’s not something I ever wanted to do. And, think I built, kind of a a smaller, career with a with a career trajectory in banking. but I was never happy doing that. I I always thought that it was kind of a a kind of a a more of a tire, boring kind stuck up, kind of space, and I wanted to do something different. I always thought I was capable of doing something different, but I have a lot of neuroticism a lot of, you know, baseline level anxiety. And I think throughout my life that prevented me from really taking risks. even though I wanted to be an entrepreneur, I never really thought that I had the the skill set or capabilities. Now that I have. and the reason why I didn’t go to University of Florida is because at the time now, all these schools are incredibly challenging to get into. So you need a 4.0 plus, to get into University of Florida, Florida, State, UCF, any of these at the time, I I was a really poor, high school student, and I didn’t have the grades to, get into, you know, University of Florida, Florida State was a a little bit easier, academically. so, that that that’s kind of why I did that. But yeah, my entrepreneurial journey didn’t start until I was a a business school student at FAU, which is here in Boca. And, when I went into that program initially, I really was doing it to to kind of, advance my career and I was applying for different positions, whether it was in banking or outside of banking. And I was finding that people needed an advanced degree. and they were looking for that, and I wasn’t really getting the looks of the jobs I wanted. And I, thought that that could help. And I, enrolled in what they consider executive program, which was designed for working professionals. And a lot of the curriculum in that program was based around, real this case studies. And we started to study some recurring revenue model businesses like, Netflix and BirchBox and, you know, did a lot of class discussion. about halfway through that program, I decided that instead of focusing on further my career, I was gonna keep my current job and, focus on what I could do to start a business, particularly a recurring revenue model business, and that’s what I did.

Glenn Harper [00:08:01]:

Do you was the the entrepreneurial thing. You said that started when you were in college. Did it how did that all of a sudden just trigger it? That mean the thought of.

Jonathan Beskin [00:08:12]:

Yeah. So, yeah, I mean, I I always I always thought about it. I always wanted to. I mean, I I didn’t grow up, with a I grew up with a single mom. so so not a lot of money. I don’t have any siblings. I don’t have a big extended family of cousins. I really never had, of anyone who was a serious entrepreneur or even you know, that I love professional or corporate professional. So, I really didn’t have any role models or ment for. So I kind of, like, fell into banking. I studied finance of Florida State. I was hired at a recruiting event, at school. So I kind of just kinda fell it. I I never really thought of, ambition or particular ambition towards a particular profession. So, my I always thought about doing more. I always wanted to make a lot more money. I, you know, it’s definitely afraid to take risks that I think is this kind of ingrained neuroticism and anxiety and kind of fear and a lot of fear in particular about what other people thought of me and like that if I started a business and it failed, which is, you know, most likely if you start, you know, something just from an idea from scratch, that, you know, people were gonna judge me more, and I felt like I had been judged my whole life. So that that that’s essentially when it when something finally clicked for me and I took action was during that MBA program at FAU. before into that, I had thought about it, but that’s actually when I took the initial action is, and then that was, like, in

Glenn Harper [00:09:52]:

20 14, 2015. Yeah. because it’s it’s funny. The, you know, an entrepreneurial journey. A lot of times, it’s you know, they’ll either have a a parent, a friend, a somebody that is helmed their shingle and did did their thing, and as an on burn, they at least could see that happening and how that works. You really didn’t get to see that. So to to make that jump, again, if you said you have those, you know, those issues of you know, the confidence and just unsure of those things. That is a huge jump to go from real job to being an entrepreneur. That’s huge. So I’m just curious on what made you decide that that’s what you had to do or that you wanted to do because that’s that is not the easy choice.

Julie Smith [00:10:34]:

But I also wanna, you know, go back to your in being a banker, right, is your skin just crawling every time you have to go to the office? And every time you have to, you know, There had to be something inside of that job or career that just said this is not for me.

Jonathan Beskin [00:10:53]:

Definitely. Yeah. I I would say there was definitely days where my skin was crawling, and I always felt like I was capable of doing more. And I never got noticed. I mean, I worked for some pretty large companies with thousands of employees at different levels of middle management and nepotism and other, things of this nature. So I never really, yeah, totally. I felt comfortable. I kinda up in a few different jobs, but none of them, you know, my one of my first jobs in banking was as a branch manager, that actually got robbed at gunpoint, which I talk about in my book. fortunately, no one was hurt. and, was kind of a a brief, event, but it, you know, it’s traumatic to an extent. And, yeah, I I I really and when I first started, I kind of hedged myself a bit because for the first two and a half years when I had this business, I was able to keep a full time job in banking and financial services, while I had the business even at a point where after the 1st year, I was making more money from the business than I was from this corporate banking job, but I had a a kid. I was a single dad. I really, yeah, felt like I didn’t have the option, and I, never could have imagined that the company, would continue to grow as quickly as it did and that, you know, I would have the success with this particular business that I did, 1st entrepreneurial venture. fortunately, you know, a lot of things, worked out well. The timing was good. I worked credibly hard. I taught myself a lot of things that, you know, it yeah. I I made a lot of sacrifices But, yeah, I I feel very fortunate that that I continued on that path and didn’t give up because particularly in those early months and early years when things didn’t always go well, I wanted to give up. And I was pretty close to it a few times.

Glenn Harper [00:13:01]:

So if you’re, you know, double dipping, we like to call because that’s the fun part, right, as you’re doing one job and doing something on the side, and it’s becoming more and more profitable where what when you just said that you were thinking about giving up, why were you thinking about giving up when it was taking off and doing very well, or was this before that?

Jonathan Beskin [00:13:19]:

it, yeah, it it it was probably when when it it started to really scale fast and there there was there was more money, and I thought this be really serious. I probably wasn’t thinking about giving up them, but in the first, maybe, year roughly, there were a lot of people, you know, when I came up with this business idea. I’m really the first, business that I, that that that I had. Now a few other things, but with single swag. and this is the 1st and largest monthly subscription service designed for single women. And a lot of people, you know, in my network, out of my network, that I was connected to that I proactively wanted to be connected to that had had some success in the space. thought I was a joke. thought that I was a a single straight guy that knows nothing about single women. you know, what am I gonna do? I need to get someone else involved. you know, I’m not gonna be able to scale without raising money. you don’t have money. So how are you to, scale this business. a lot of people, you know, thinking it was a a a joke, this type of thing. So I think that took a a toll, definitely kind of people, you know, being overtly negative about the idea and about what I was doing. And I I I think, with any business in the early stages, I mean, you know, ran into some, challenges. So had some challenges. You know, we you know, sign up the business kind of commerce is all e commerce. So we, only operate in a website. We accept money on a website, but it involves some this product. so we had some issues shipping physical product. We had some issues receiving some of the physical product to put in the boxes. And initially, I was doing all on my own. So I was not only, you know, facilitating the website, acquiring the customer by learning different types of advertising, which eventually became the reason we scaled because that kind of became my area of expert tease of social media advertising, particularly on Facebook and Instagram, but, you know, there are some logistical challenges and, you know, started to just, re require a lot of time and kind of became overwhelming. And I think it was also overwhelming to have a full time job. Even though this is before COVID, I had a job that was kind of half remote, and I kind of worked my way into that. it was a lot to, to handle, everything. And I also had a a young son who at the time was around five years old and had a responsibilities around that. So, wasn’t sleeping that much and wasn’t eating right. And, you know, there there there were a number of reasons. you know, that that I wasn’t being, healthy. I was doing something very positive for my life in the long run, but in the short term wasn’t really living. healthy lifestyle.

Julie Smith [00:16:15]:

So with all that negative self talk that you had to work through at that point in time in your journey, had you found a mentor or someone who could be your cheerleader who could help get you over that mountain?

Jonathan Beskin [00:16:29]:

so, I I would say not someone that I would classify as like a mentor that I was meeting with on a regular basis that I had the ability to bounce ideas off that. Now I have that now. Fortunately, I’ve kind of established. I’ve joined, few organizations for business owners. I I I’ve cultivated a little bit more that I do have people that are way more successful than I am that I the bounce ideas off of, but, so I have a a a cousin who lives on the host that has had some pretty serious success in business that I, you know, wasn’t even necessarily aware of, but, had some conversations with and, became somewhat mentor, but it wasn’t someone that I connected with on a daily basis that when I felt like I was having an issue or to overcome. I did, but, I I I feel like, you know, it it’s kinda good and bad. It’s bad that I didn’t have that support. But even if I had that support, you know, what I found is that, what mentors or what may work in one business may not work in another business. So even if someone is super sophisticated, has had incredible success that built multiple companies, their advice and their, you know, kind of council or direction for your business may not apply. So I think, you know, in my view, needs to come from you and learning and figuring things out.

Glenn Harper [00:18:04]:

So, you know, I think what You said something about 5 minutes ago that sure all the listeners wanna know because somebody said that you didn’t know. What do you know about single women. So did you figure all that out?

Jonathan Beskin [00:18:17]:

well, I I definitely, wouldn’t say I figured, single women out, but, I I definitely learned a lot more and, you know, we have a team, who helps us put together our boxes. So we, for single swag, it’s a scriptured service. So people sign up for the service. Every month, we send them a box of full size women’s lifestyle products, like fashion accessories, jewelry, cosmetics, organic skincare products, snacks, books, all that. If everyone gets the same products. So people with different, ethnicities, people with different sizes and and and all all kinds. So we have to have items in the box that are gonna have broad appeal. And it’s very important to, to kind of be mindful of that and be thoughtful about goes in the boxes. So, I definitely learn about the products, that that resonate best with women. and, what’s what what of these items are gonna have the the broad appeal. And, yeah, I I mean, I’ve I’ve learned a lot about consumer behavior in general. I think a lot of it applies to women because that’s really who we’re marketing to, but that comes with, a lot of the digital advertising that that, I’ve been engaged in and, building audiences, which that market has really changed. So, when I started this business in 2016 through

Glenn Harper [00:19:45]:


Jonathan Beskin [00:19:46]:

where we did incredibly well, you know, the digital advertising and Facebook and Instagram did incredibly well. And the targeting worked very well, in early to mid 2021 with the roll out of the Apple, iOS privacy updates and, you know, a few other variables that performance has deteriorated and is, essentially you know, really been a a challenge to overcome for a lot of ecommerce businesses, particularly focused on, advertising social media, but kinda went off track there. But in in in general, I I understand single women as it relates to this business and what’s gonna make them happy. myself, as an individual, I definitely do not understand. sinking women.

Glenn Harper [00:20:35]:

That’s that’s why I think it’s so funny because here here you are, you’re gonna go be an entrepreneur. You know nothing about it. Nobody’s was supporting you. then you’re gonna like, what can I sell? Let’s pick the hardest demographic. I don’t even know what I want as a guy, and you’re gonna go sell stuff to chicks. I mean, you couldn’t have picked a harder thing. So hats off to you because that is a really unique niche to get into and to just be able to say, well, I’m gonna do it. and everybody’s telling you, no. Again, when you’re an entrepreneur, you gotta do the hard stuff. If you do the hard stuff, everything else is easy. Right? And what you said earlier too, I want to go back to is, you know, the mentoring might not be just in the industry for your entrepreneurs listening. It’s it’s not necessarily to help you in your industry. It’s just somebody that help you believe in yourself and and give you a positive feedback, honest, that says, hey. To be successful, this is what you wanna do. Whatever that idea is you you can do it. And you didn’t have any of that. Like, not only you didn’t have nothing in specific to your industry, but nobody was telling you positive things. So, again, it’s very rare that somebody goes and does this all on their own and is successful. Normally, there’s somebody that, you know, gives them a pat on the back, pulls them up you know, by giving them a hand and helps them up. So I I kudos to you for being able to do it on your own. That’s it’s hard out there by yourself.

Jonathan Beskin [00:21:57]:

Yeah. Well, thank you. And, fortunately, moving forward, I do have somewhat of a a network, but I agree with you, but I think there there definitely is value for me at least or potentially for others and, you know, doing it on your own and figuring things out and it forces you into just an uncomfortable space that you have to deal with to to kinda get there. And one thing I want to mention about, what said about the idea for for single women and focus on that. When I had the idea originally, I want to focus on men and women because I was really thinking about myself and my own, kind of thoughts on being single, and I had the idea when I was home, alone. I Friday night. And I saw all these people, and I had to be home with my son who was young at the time. all these people going out on Facebook and partying and posting and and living their best lives and and, you know, doing all this. And I thought that single people, you know, I hadn’t been in a relationship a while. I haven’t gotten gift in a while, and I have this recurring revenue on box business, top of my, so we’ve been studying it in my MBA program. And I had the idea for both men and women, and I did some market research, which I think is very important for aspiring entrepreneurs when they are starting a business to kinda figure out. And really the consumers for these boxes, were women, and the community that were being built, on the platform. And, really, at that time, Instagram was really the the platform that you needed to build a a foundation on and so that’s why I decided to focus just on women because after that research, I thought that was the place to start, then maybe event really get into men, never end up getting into, any male version of of these companies, but, that that that’s kind of how that played out.

Glenn Harper [00:23:49]:

Yeah. Men would be be the easiest. It’s just like a video game card, a pizza coupon, and a beer coupon, and and we’re good. there’s there’s not a lot a lot of sophistication there, which is crazy.

Julie Smith [00:24:00]:

Of course, Glenn and Glenn would say that. But I

Glenn Harper [00:24:02]:

don’t do the video gaming, but a lot of dudes do. I’m just saying that’s what, you know, people dig that.

Julie Smith [00:24:07]:

So I one of my questions was your inspiration behind, you know, finding this business. So thank you for answering that. But then to take it a step further, at what point did you just side, you needed a team. You know, you’re doing this. It’s grueling. You’re grinding it out. At what point did you have that moment of, like, it can’t just be me?

Jonathan Beskin [00:24:27]:

Yeah. so the the business, pretty quickly, within a year started to become more serious. We went spending, $20 a day on Facebook ads to, 50 to a

Glenn Harper [00:24:39]:


Jonathan Beskin [00:24:39]:

to 500 to 1000 a day on Facebook ads, and we were able to get a predictable results and, scale the business that way. So, I, at the time, I was really doing everything. So I was doing every thing from, sourcing the product, to sourcing the materials, to running the Facebook ads, running the Google ads, managing different aspects of the website, which initially I kinda build myself, then eventually we had a more slick website designer build better product there, customer service. So, you know, within a couple months, we’re shipping out 500 boxes we’re getting emails or direct message on social media. Where’s my box? You know, how do I cancel things of this nature? So I’m really doing everything. And I, really, you know, became, like, addicted to it in a way. I’ve I’ve came, like, obsessed with it, and it it was, in, you know, a little bit the best way to describe it. I don’t have a lot of experience with drugs, but but it it it like a drug in a sense where where just, you know, I I I never had this exciting thing happen, and and it was for exciting. And I didn’t mind staying up till all hours at the night kinda doing stuff because it’s just an exciting time. But eventually or pretty quickly, I realized that in order to get to the next level and focusing on more growth, I couldn’t be doing things like answering customer service, simple emails like, you know, when does my product ship or doing simple, kind of organic posts on social media. or sending out every email to every potential product vendor. but, you know, unfortunately, for me, and this still something I I have a kind of a weakness with is that I, because some things that happened to my childhood and my family, I inherently have major trust issues. And I, a lot of times, you know, even when I had some employees that someone didn’t do something right instead of, showing them how to do it instead of kind of stepping in and and being more a mentor, I would just do it myself. because I knew that I was capable of of doing the best. And, I think what I eventually realized, and and the first kind of people that I hired well, the first person I hired was my bubble. And, you know, who’s who’s even more neurotic than I am, and it wasn’t easy to kind of, you know, be in this, you know, kind of dynamic with my mother single day, but I knew I could trust her. And and that was kind of an emotional hurdle to get over. I knew that her best interests, were gonna be a lot you know, her choozah is gonna have my best interests of mine that that she was even if she didn’t have a skill set, she was an, elementary school teacher for 40 years and kinda tired early to come work with me and still works with me. And, really, you know, was excited about it too, but didn’t really have the right skill set that someone you know, who had worked in social media that had experienced with customer service, but, it it it was really a a a good way to to get, you know, something going initially and get some stuff off my plate. And, you know, she was able to learn and a very, you know, smart person. Something that I realized pretty quickly is that, you know, just using customer service as the example, and using this kind of, control free trust issues mentality that I have, some ways I still have, you know, I need I needed to realize that I couldn’t monitor every customer service message and that people that I hired to respond these messages, as long as they’re handling in a professional way, as long as they’re getting the job done, they’re not gonna answer these messages in the same way that I would. I would be much more thoughtful about answering every single message. I would do that, but it’s not realistic for me to dedicate my time, you know, at all to to to things like that and to really build out a team. And I think that that was an important a a lesson for me to get over is that I, you know, if you wanna get to scale in a business, you can’t, you know, be concerned with with every little detail. And I guess in a way I prioritize what I had to be concerned with. So I couldn’t be concerned with monitoring or responding to customer service message or posting every time on social media, but I it would be better for me to focus on, much more higher levels strategic thing. So how are we gonna acquire more customers, where are we gonna build the boxes from? how are we going to reduce our operating costs you know, from shipping and and and fulfillment and, securing products. And we eventually moved to a model where we worked with a lot of established brands who were shipping out over 50,000 bucks a month that our Pete were to establish brands, but we started to create a lot of our own product. and kind of had a suite of in house brands that we were manufacturing the products and and creating the brand assets, and that was saving a lot of money. making that if it as opposed to buying from established brands doing it ourselves. So I needed to free myself up to be able to make more decisions like that and and and that, you know, helped out a lot. And eventually, we got to you know, bigger team. we even tried to outsource, you know, some of the customer service aspects over sees, that worked out for some time, and then we kinda brought it back. But it’s been an evolution, and still something that is challenging for me, but I’m working to become, a better leader as opposed to just a very effective, operator and kind of doer.

Julie Smith [00:30:44]:

So for our listeners, I think you hit the nail on the head because I think a lot of entrepreneurs go through that same thought process in regards to having to give up that control. What was your moment where you just cited or what happened or transpired to make you kind of push you to that moment of saying, okay. I can’t do it all. Okay. I have to pry advertise, okay, I can’t do this. What what made you get to that point to get to where you are today?

Jonathan Beskin [00:31:12]:

Yeah. I I’m not sure I could pinpoint the exact moment, but I I I think I it it just really became overwhelming. so I, was at a point where I literally described and I talked about this in my book, like, I had 20 jobs at the same time plus a full time job outside of this business, plus a, you know, young, son that I had half the time. So, yeah, it it it really, just kind of the the business scales, very quickly and, you know, relative terms. And I, just just knew that that I needed help, to to get to the next level. I think the the most important thing, and I’ll kind of repeat it in a way just because I think it it was really about prioritizing and figuring out where that that that help us best. And I think every business, could be could be different, but, you know, what what is that particular area focus in the business that, you know, if you weren’t a daily basis and, you know, is that going to affect the growth of the business, the operational health of the business, the economic success of the business, by, you know, giving up that that that area And I really feel like I I’ve waited too long, and I was always even I’ve never really had, you know, a a serious executive team. They’re they’re my employee and the person that’s been with us the longest is someone I’ve went to that MBA program with. And, really, really wonderful person. Her name is Jen. And other than Jen, I I really haven’t, hired anyone. I’ve been approached by recruiting firms. I’ve talked to other people about some businesses that eventually become somewhat of mentors, and they told me to hire some more executive talent or bring in some more operators who’ve done this. And I was always, you know, and I’m afraid to do that, and I never really did. And now the business is not the same business as was in

Glenn Harper [00:33:28]:


Jonathan Beskin [00:33:29]:

And, you know, maybe just as a lesson for myself, if I would have been willing to bring in that that that talent. And if I would be willing to hire more and not do so much myself and not wanna spend the money to bring in these really talented, you know, people to get to the next level. The business is gonna be cheaper and more success. I could be even more successful at that point. so I think that’s that that’s an important lesson too. I mean, hindsight is 2020. I don’t know that the case, but, you know, I think it’s possible.

Julie Smith [00:34:02]:

And I think we call that getting out of your own way.

Glenn Harper [00:34:05]:

Julie’s reading all my thoughts today. That’s great. Well, we we done this a while. you know, it’s it’s, you know, when you’re an entrepreneur, the OCD is strong with us because We look at things with different lens. Right? Everything’s an opportunity versus an obstacle. Right? And, you know, if you have a real job probably gotta take medication to stay in your lane. But when you go as an entrepreneur, you get to be free and do whatever you want. Right? But that also is a cost because you think that you have to do everything because it’s really hard to give up control and trust like most people do. And at some point, no matter how good you are, you can’t do it all. And and and is anybody’s listening to this this show right now, the the concept is is that I think I don’t wouldn’t call it regret would just think that maybe it would be, you know, you’ll still be where you were, but it would change the trajectory of things if you were to recognize that earlier that you’ve gotta empower other people and just let them take that off your plate because your skill set is the vision the mission, are those all those things that help define the company that you’re leading versus doing the minutia task. Right? And and that’s probably what you would probably say is Your biggest regret, but not not it can’t say regret.

Julie Smith [00:35:19]:


Glenn Harper [00:35:19]:

Yeah. Just the biggest man. I wish I had done that. That’d probably been a a good choice. Right?

Jonathan Beskin [00:35:24]:

It’s definitely up there. And, I, yeah, I I I feel like in my next business, you know, what what having this success has really done me, which, feels good is that, you know, I no longer have, neuroticism about not being able do this. I feel confident that I can lose everything I have and do this again because I I I built a a skill set. I have the confidence now. I I I think I can do it. So, I I I that that’s how kind of going through whole process has changed me. And also, you know, to to your point, I would definitely do things differently. I would, you know, not do everything myself. I I I would be more proactive about, you know, bringing in qualified health, even for my own health and, you know, things like that because it’s really I I feel like if if I would have continued to operate as I was operating those 1st couple of years, I mean, that that that would take you know, years or decades off my life, getting, you know,

Glenn Harper [00:36:33]:


Jonathan Beskin [00:36:33]:

hours of sleep at night, not eating right. it’s very exciting time to growing business, but, you know, personally, I I was just being incredibly, unhealthy.

Glenn Harper [00:36:45]:

And that knowledge and experience is power. once you figure that out. And that’s the fun thing about we always talk about the entrepreneurial journey. It’s it’s not what it’s not the result of all that hard work. It’s who you become in the process. Right? It’s a it’s finding out, you know, your skill set, your strengths, build up the confidence, being the person that you’re probably destined to be. And the only way you do that is you gotta do hard things. You gotta get be told no all the time. You gotta be told you can’t do it. And you’re probably one of those guys that you develop your strength from everybody telling you couldn’t do it to prove somebody wrong versus somebody saying, hey. You can do it. which again, you still got there. You just got there in different way. But for all the listeners, again, there’s no right or wrong way. You just gotta kinda deal with the cards you’re dealt with and and again, recognizing those opportunities as they come aboard.

Jonathan Beskin [00:37:33]:

Yeah. I I I totally, agree with what you’re saying. And I and I think it’s kind of a blessing and a curse with kind of proving people wrong because I definitely, was motivated by that still motivated by that, and sometimes, too motivated by that. Sometimes I’m regardless of how much success I I I’ve had and how much money I have or anything like that. It’s never enough, and I’m so focused on still, you know, seeing if if these people that really are so insignificant at this point in my life are paying attention. And it’s just not a healthy way to to operate, and and it doesn’t allow you to times live in the moment and just be happy with what you’ve done because, you’re so focused on still proving people wrong that that really treated you, poorly or doubted you or anything like that. So that’s something that I’m working on personally. is how, you know, as I get older and and and kinda figure things out and not working as hard, how can I live my life without the kind of burden or weight of all these people that I think about so often or all these that are, like I said, essentially irrelevant, not impacting my life in a negative way.

Glenn Harper [00:38:49]:

I mean, you you I’ve just met you, of course, but you look pretty relaxed. You look like you don’t have a care in the world. So, Whatever you’re doing, I would probably say keep doing it.

Jonathan Beskin [00:38:58]:

Yeah. Well, I’m I’m definitely good. portraying that or conveying that. I would say right now, I really don’t have that much worry about my son is at a a sleepaway camp in in a rural Sylvania. I have times life. I fished a few times this week on a boat I have here in South Florida. So, yeah, I I I definitely, I’m not as hard as I was a few years ago, but, I I’m definitely I think, when you, you know, deal with anxiety and depression and things like that, which I have my whole life, it’s not something that really goes away. And, you know, what I talk about in the book and and and kind of what I’ve been able to do for myself is you know, knowing that that stuff is not gonna go away from me and knowing that it’s always gonna be there regardless of what I do or try to remedy it is how can I channel it in a way that’s gonna be positive for me? So how can I channel it in ways that are gonna lead to more success going to, help me out of my life. And, I’m not even always doing that. good days and bad days, but I I I feel like for myself and hopefully for others, I’ve been able to figure out a little bit of a formula, to, you know, just take that energy and put it into something positive.

Glenn Harper [00:40:25]:

Yeah. It’s funny. a lot times, people spend their entire life trying to swim upstream, fighting the waves. Sometimes just kinda ride it out and see what happens and enjoy the ride. and, don’t be so critical. And next thing you know, you’re having the time of your life. So I I think you’ve probably been able to to do that. Julie always has a a good question at this point, Tyler?

Julie Smith [00:40:46]:

I have a couple more questions. What is your superpower? And I think you’ve probably alluded to it. but could could you define that for us? What do you think your superpower is?

Jonathan Beskin [00:40:59]:

Yeah. Haven’t been asked that, uh-uh, at at all recently. I’m actually I I feel fortunate to be to be asked that. I I I don’t even know, consider myself to, have the superpower. what I would say is is what I feel is of my biggest strengths is that I’m incredibly disciplined. so, before I had this business, I was a pretty serious marathon runner. for about, you know, 4 to 5 years, and I was pretty obsessed with that. Now I’ve gotten older. My body definitely can’t handle that. I can barely run a a couple miles at this point. Unfortunately, because it is something that’s kind of therapeutic mentally for me, but yeah, I, you know, that involved a little discipline because I really need it to be on a very structured training regimen, and I need to be structured. But the way I ate, and I was doing yoga and I, you know, how to run a certain amount of miles, and I had to pay attention to my weight and, shoes I was wearing and and and stuff like that. for the business, I’m also very structured to and and discipline. I I feel like as I’m describing this is like the most boring, super power, of all time. but yeah. I I I because I couldn’t think of anything better. I I do feel like that’s, kind of the strength that I’m able to, kind of focus on something. And when when something, you know, when I have a goal to achieve, whether it’s the marathon running or or continuing the success. You know, I’m convinced that millions of people, and I think people did before I had this business could have had this idea It was really, you know, wasn’t locked. It was the way I executed the the way that I sacrificed, you know, not watching a lot of TV not going out with friends, you know, making these short term sacrifices by being disciplined that that kind of led to you know, really great long term success.

Julie Smith [00:42:59]:

And I would build on that, and I think it’s all about your energy. And I think you’ve figured out how to take, and I don’t wanna say negative energy, but energy that’s over, you know, on this side and really put it into something that’s very — obstructive, something that you wanna do, you can work towards instead of wallowing, you know, over here and saying, oh my gosh, I can’t go run thirteen miles. My body hurts. I need new shoes. Oh, I didn’t eat right today or whatever the case may be. You have figured out how to take that energy and say, I’m gonna run thirteen miles, and I don’t care what my shoes are, and I’m gonna it doesn’t matter that I eat McDonald’s for lunch. I’m still gonna do it. And so I think that energy goes with the discipline that you’re describing.

Jonathan Beskin [00:43:38]:

Yeah. I, totally agree with with what you said, and and I think that, yeah, I I always have this constant, I feel like higher baseline level of anxiety. So I just know when I wake up in the morning, that’s just part of what I need to kind of deal with. And I think immediately for, you know, anything that I’m doing in my life, it’s really about channeling that energy, you know, to something else. For me, when I was building my business, it was really about, you know, taking racing thoughts, taking, you know, even catastrophizing and putting all that into thinking about a business from every single angle thinking about what the competitors are doing, thinking about what I need to do next, thinking about what the competitors could be doing, thinking about what our custom might do next, what what what the industry, you know, what pro I mean, there’s, you know, so many different facets And, you know, when I’m thinking about, this stuff that for me is positive for me, making a positive change in my life. I’m not thinking about all the people that did me wrong. I’m not thinking about that I you know, didn’t grow up in a good situation that people treated me like crap. I’m not thinking about. There’s certain things about myself that I don’t like or, you know, I’m when I’m focused on these things that this kind of healthy obsession, I’m not thinking about all these negative things that are that are wrong with me, that if I didn’t have something to focus on, that’s all I’d be thinking about is all these negative things that are wrong

Glenn Harper [00:45:20]:

Well, I think that’s that’s the, you know, I’m gonna add a little so that you’re super proud. I think once you make the decision of what something you’re gonna go do, you go do it. And and a lot of people, it’s hard to find that thing that they wanna do or gonna do so they just don’t do anything. your probably superpower is probably I’m gonna go do this and then you’re manic by getting it done. And and that, my friend, is probably one of the keys to your success is that Once you’ve identified it, you isolate it, you just go get it. And and that’s an important superpower.

Julie Smith [00:45:52]:

And I guess I I visualize, and I’ve been told this, so it’s okay if comes across because I’ve been told this, but I visualize, like, 4 bulldozers in your backyard. And your your energy says I’m gonna go, I don’t know, I’m gonna go fishing, but there’s all these obstacles in the way where you just bulldoze right through them to go fishing. And once you’re there fishing, you’re just in your element and you’re doing what you do. And I I — Yeah.

Glenn Harper [00:46:14]:

Julie Smith [00:46:14]:

I commend that strength because I sometimes live it. But, so your energy and — what you’ve been able to do and overcome, I I think speak, you know, greatly to your success and and what you’re doing and how you’re handling yourself.

Glenn Harper [00:46:30]:

Well, I tell you that’s it’s been a pleasure having you Wait.

Julie Smith [00:46:33]:

I have one more. I have one more question. Oh. Sorry.

Glenn Harper [00:46:35]:

But wait. There’s more.

Julie Smith [00:46:36]:

You’re gonna have to think a little little bit more. What is your end game?

Jonathan Beskin [00:46:42]:

So, yeah, you you got good questions. so That that is something that I, think about quite a bit. And, you know, probably too much, actually. I I think that I it just it’s just one of those things I feel like that doesn’t allow me to to live in the moment when I’m too focused on the future and and what’s gonna be next. I I I definitely don’t think I’m done, working or being an entrepreneur at this point. I’m 42. I, feel like I have multiple businesses left in me. My business now that we’ve been talking about, my primary businesses, the description box, are not doing as well as they were in, you know, 2020. you know, we’re a top 200 and 85,000. So I’m focused on, you know, do do do more. I’m I wrote a book. I’m trying to cultivate a personal brand, do some speaking, really, use my story to help in in inspire others. But now I feel like I’m rambling that I I feel like eventually my endgame do, just be happy. and figure out a way to on a consistent basis, regardless of of money, success, or anything that’s going on to to just be more happy and and be more, carefree and not be you know, I I I think I I described as a blessing and a curse because in in a lot of ways that has cursed this whole thing that motivated me to get to next level and change. My wife was really proving people wrong even like my own father. Like like like, really deep seated stuff and and, you know, it still motivates me, but I I I wish it didn’t now in some ways now that I’ve had some success because it’s it it it just very toxic to have to, you know, deal with that on a on a system basis and have to, you know, be be so worried about, you know, being judged in in in so many different ways. So I think that’s really the end game. I think that I’ll I’ll know that that that that’s really a game changer for me is when I can just be more of a carefree person on a consistent basis. And, yeah. So

Glenn Harper [00:49:14]:

Julie Smith [00:49:14]:

Well, I mean, You’re laughing. Your answer is great because you just talked in circles. Right? But I don’t think there’s an end game for you. I don’t think that you can stop channeling and doing what you’re doing in order to create your carefree freedom. I think your carefree freedom comes from what you’re doing and how you’re doing it.

Glenn Harper [00:49:35]:

You you’re having too much fun. You and you’re enjoying yourself. You know too much now to just stop and be a fishing boat captain would be cool. But after about 2 weeks of that

Julie Smith [00:49:44]:

You’d own your own fishing boat pull fleet of boats or whatever they’re called.

Glenn Harper [00:49:48]:

You’d have a whole yeah. You’d have Sweet.

Julie Smith [00:49:49]:

That’s not Yeah.

Glenn Harper [00:49:50]:

It’d be a fleet of folks. Yeah. But, yeah, I I don’t think it’s ever gonna stop because you’ve tracked the code. You know how to do this. You’re good at it. You know how to leverage it. It’s it’s hard, but it’s not hard in a way where you’re doing everything. You just gotta think it through, but other people, you’ve leverage to do that. So you’re probably just gonna keep doing this forever

Julie Smith [00:50:09]:

because why don’t

Glenn Harper [00:50:10]:

you stop?

Julie Smith [00:50:10]:

And I think it’s what makes you feel good. Yeah. It gives you that that boat of confidence and that Hey. Look at me. In a positive, very positive manner.

Glenn Harper [00:50:20]:

And, again, I’m not a shrink. I know shrinks of imagination and don’t take this for gospel, but I think you’re over all those things in all honesty because you’re you’re doing these things because you enjoy it and you look at all the opportunity. you’re done proving it to anybody. You’re you’re just doing it because you like to do it. So just take that as a grain of salt. That’s my non expert opinion. I did take one side class, but

Julie Smith [00:50:41]:

And he failed it, but that’s fine.

Jonathan Beskin [00:50:42]:

And I

Glenn Harper [00:50:43]:

did retake it. but I

Julie Smith [00:50:44]:

was kidding. I didn’t even know.

Glenn Harper [00:50:47]:

Well Oh. It’s been a pleasure on, do you have any, plugs you wanna give for our listeners in case you wanna buy some cool stuff?

Jonathan Beskin [00:50:54]:

Yeah. But before I give a plug, I just have to say that that last question and and and really, I’ve I’ve done a lot of these interviews recently podcast, particularly around the the book I’ve written and and there haven’t been a lot of, situations or questions that really led me learn something or led me to Lorenton by myself and and genuinely, the the the last question that was asked. And you know, it is is an eye opener for me that they’re, you know, that that I’m kind of, living my to an extent that if I can, continue, you know, I’ve been on internal center fee that that that that really. It peaks. I I do kinda date dream about certain things, but but this is really where I’m happy. So I appreciate that. so anyone that that wants to connect with me, I’d be happy to connect. you can find me on Instagram at jbespin. I’m also on TikTok, which really embarrasses my fourteen year old son. every time I do a post on there, he’s like, you know, go jump off a bridge. I mean, so that’s at Jonathan Baskin. And, I also have a website, By the way, it’s j0nathan And, my book, which is gonna be out at the end of August, is the least likely millionaire. how to succeed when everyone expects you to fail. so I’m excited about that and to help people check that out as well.

Julie Smith [00:52:27]:

Well, you’ve been you’ve been a an amazing guest, and we’ve learned from you as much as as you’ve learned from us.

Glenn Harper [00:52:32]:

This is great stuff. And, you know, again, can’t wait to follow-up with you in a year, and see how you even more relaxed you. Like, you’d probably be all tatted up or something. I don’t know. We’ll see. Yeah.

Jonathan Beskin [00:52:42]:

Well, if you saw me without a shirt, it’s too. A lot more tattoos.

Glenn Harper [00:52:45]:

See, there you go. I knew it. I knew it. I’ll wait for the one on the face like the Tyson tattoo. No. I’m kidding. That it’s Again, it likes to it’s too much fun. There’s too much opportunity to sweat the small stuff, and I think you’ve making tremendous strides. And I think you’re on the you’re you’re on the downhills just enjoying life. So keep it going.

Jonathan Beskin [00:53:03]:

I appreciate it. Thank you for having me. It was great to meet you both.

Glenn Harper [00:53:06]:

Thanks, Jonathan. We’ll see you, man. Take care.

Episode Show Notes

Jonathan Beskin is the Founder and CEO of SinglesSwag, a subscription service designed to empower single women. In less than five years, Jonathan’s startup has accumulated $60 million in revenue. He has been featured twice in the Inc. 5000 list.

Jonathan Beskin began his career in banking, but quickly realized that it wasn’t his true passion. Despite always wanting to be an entrepreneur, Jonathan struggled with self-doubt and anxiety. His entrepreneurial journey started while he was a business school student at FAU, where he enrolled in an executive program designed for working professionals.

During this program, Jonathan studied real-life case studies of businesses with recurring revenue models, such as Netflix and Birchbox. Inspired by these discussions, he made the decision to focus on starting his own recurring revenue model business instead of solely advancing his career. Jonathan chose to keep his current job and devoted his efforts to building his own business in this field.

Jonathan shares his experiences, challenges, and successes as an entrepreneur, providing valuable insights for aspiring business leaders. Here are three key takeaways from this inspiring episode:

🔑 1. Embracing Anxiety as Fuel: Jonathan discusses how he channels his baseline level of anxiety into his business. By thinking about various aspects, such as competitors, customers, and industry trends, he stays ahead in the game and drives positive change.

🔑 2. The Power of Discipline: Jonathan’s marathon running background has taught him the importance of discipline, which he believes is crucial for entrepreneurial success. He shares how sacrifices and a strong work ethic have helped him maintain focus and build a thriving business.

🔑 3. Delegating and Prioritizing: As his business grew, Jonathan realized the need to delegate tasks and prioritize higher-level strategic decisions. He reflects on the challenges of letting go, trusting others, and becoming a better leader.

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