Entrepreneurship Podcast post

Getting Unstuck with Jonathan Beskin

George Grombacher September 28, 2023

share close

Getting Unstuck with Jonathan Beskin

LifeBlood: We talked about getting unstuck, overcoming traumatic experience and mental health struggles, the good and bad of having a chip on your shoulder, and succeeding in business against all odds, with Jonathan Beskin, serial entrepreneur, Inc 5000 honoree, digital ad expert, and author.       

Listen to learn how you can redirect negative thinking and feeling!

You can learn more about Jonathan at JonathanBeskin.com, Facebook, TikTok, Instagram, and LinkedIn.

Get your copy of The Least Likely Millionaire HERE

Thanks, as always for listening! If you got some value and enjoyed the show, please leave us a review here:


You can learn more about us at LifeBlood.Live, Twitter, LinkedIn, Instagram, YouTube and Facebook or you’d like to be a guest on the show, contact us at contact@LifeBlood.Live. 

Stay up to date by getting our monthly updates.

Want to say “Thanks!” You can buy us a cup of coffee.


Invest in yourself. Bring it All Together.

Work with a coach to unlock personal and professional potential.

Our Guests

George Grombacher

Jonathan Beskin

Episode Transcript

Jonathan Beskin 0:30
Sure, well, I live in Boca Raton, Florida. I am a single dad to a 14 year old songs.

george grombacher 0:02
Jonathan Baskin is a serial entrepreneur and digital ad expert has been honored by the Inc 5000 List numerous times he is the author of the least likely millionaire how to succeed when everyone expects you to fail. Welcome, Jonathan.

Jonathan Beskin 0:20
Thank you. Happy to be here.

george grombacher 0:22
Yeah, excited to have you on. Tell us a little about your personal lives more about your work and why you do what you do.

Jonathan Beskin 0:37
And I think what’s most notable is that about seven years ago, I started my first company called single swag. So this is the first and kind of largest now Subscription Box Company marketed towards single women. That company is a top 200 Inc 5000. Company. We were on the list of fastest growing companies in America twice, top 10 and growth in Florida. And what really drove that revenue growth was digital advertising, particularly on Facebook and Instagram. And I really started the business when I had no money when I had no expertise or resources and scaled that on my own pretty much to over 60 million in revenue in under five years. And I did a lot of that actually, while I had a full time job in financial services, I kind of had a 10 year professional corporate career prior to starting this business. I have an MBA from FAU, here in South Florida. And I look forward to answer more questions about all that.

george grombacher 1:46
Yeah, I appreciate that very much. So how to succeed when no one expects you to win everyone except expects you to fail? Everyone?

Jonathan Beskin 1:57
Yeah, well, I think for me, it really felt like everyone at different points in my life. And you know, it’s kind of a blessing and a curse, because I think I’m very motivated by proving people wrong. And I think people it’s kind of proverbial, just people in quotes. There are some specific events throughout my life, which I talked about in the book, the least like a millionaire. And the subtitle is how to succeed when everyone expects you to fail. You know, there were pivotable, not only in my childhood, in my upbringing, I also was hospitalized for mental illness as an adolescent and twice as an adult, and faced a lot of adversity. And even when I was starting my company, there were a lot of individuals who had had some professional success that were entrepreneurs, that told me all the reasons why this idea would never work, then I’m a straight single guy, what do I know about single women? What do I know about a subscription box and ecommerce business, I needed to raise money, which I never did to kind of scale a business. So really, I was told all the reasons why I would never succeed why this specific business would never get off the ground. And in a lot of ways, it was emotionally draining a lot of the kind of toxic energy around that made me want to quit. And there were times while I was scaling the business that I was very close to quitting. And that I, you know, was sad, and I thought my wife was never going to change. But fortunately, I stuck with it. I kind of trusted my gut and my intuition. And it’s really been a life changing business and kind of for myself and my family.

george grombacher 3:50
I am somebody who I have a deep appreciation for having a chip on one shoulder as I always have had one. Also. I have identified limiting beliefs that I’ve had in the past, do I’ve never, I don’t think I’ve ever struggled necessarily with mental health. Although I think we all probably do a little bit how close did you come to actually quitting?

Jonathan Beskin 4:25
Very close. So, you know, I remember one conversation in particular that there was an individual and I do talk about this and kind of detail in the book that had a similar business, so they have a subscription box company. This was around the time I was starting mine. I have like maybe five to 700 subscribers in my business at the time, so I still wouldn’t say it was a super serious business like it eventually became just to put in perspective. At the peak of the business. We were shipping out over 50,000 boxes a month and we shipped over 2 million boxes to Earth. 300,000 customers this point, but at that time, that individual had a giant company to me, in my kind of limited knowledge, limited experience. And they basically laughed at my idea, told me it wasn’t going to work. And that was probably the point where, and told me the specific reasons why was that I couldn’t do without raising money, so that I should be focused on raising money and bringing in the type of smart money that would help me scale the business that would bring in the professional expertise and the sophistication, and also potentially bringing a woman because as a guy, I wouldn’t be able to scale a business focus on single women. And when I had the idea for this business, I was single at the time, I was kind of thinking about these recurring revenue model companies, because that was part of the curriculum I studied in business school. And I had the idea for both men and women, when I did some research, the consumers for this type of product at the time, were primarily women. So that’s why I kind of made the decision to focus on women. And, yeah, I came very close, I wanted to give up and I really thought that my life was gonna change. But, you know, something, kept me going. And I’m not sure that I can articulate exactly what that was, other than this kind of burning desire to change my life. And that’s what I was really destined to do. I’m convinced that, you know, millions of individuals could have had the same idea, and not been able to scale. You know, the attractive thing about the business I started, is that there’s really very low barriers to entry. So anyone can start this type of company. So as an E commerce business, there’s really not a lot of overhead, I started with under $2,000, and grew to 60 million and under five years. And I think a lot of other people could do that. I think, really, the challenge is scale. So there’s hundreds of 1000 businesses out there that become hobby businesses, or things that people do out of their home, or their garage, that don’t really become a serious situation. And fortunately, mine did. And a lot of that was based on a lot of hard work and sacrifice that I made personally.

george grombacher 7:22
You said that your son is 14, you started your business seven years ago? Do you think that you would have stuck it out if he hadn’t been in the picture?

Jonathan Beskin 7:36
Yeah, that’s a good question. I haven’t been asked that before. So I, I think, you know, having a kid is definitely a motivator. And, you know, really, you’re not just doing it for yourself. I think in some ways, I may have, you know, scaled in a different way or done, you know, kind of bound my life differently. It’s hard to like, say, if he was in the picture, how my life would have played out what, what different events, part of it was that I had the idea because I was sitting at home alone one night, and other people, and because I had my son at home, and I couldn’t go out, and he’s like, at a really young age at the time, and other people were posting on social media, and I was kind of a little bit sad and lonely at the time. So I think, from that perspective, it probably wouldn’t have ever happened, or this particular maybe it would have been another business. But who knows, I think it’s really hard to have repeat success, I think, you know, to create a brand from nothing and turn it into a brand that people right. Recognize with millions of followers on social media, and some inc 5000, you know, recognition or type growth. It’s hard to repeat that. I mean, people who do that multiple times, like true serial entrepreneurs are pretty amazing. From my perspective. So I yeah, I mean, I feel fortunate, and I think, really general, everything in my life that has happened, I mean, gay marriage and divorce, having a kid facing the adversity I face as a kid having some father who did some really nasty things to me and my mom when I was growing up. It you know, if I didn’t experience all of that, I wouldn’t have done what I did. Like it all kind of led to that kind of culmination in my mind. So I think that, you know, I wouldn’t say it’s positive because a lot of this stuff is very negative, that I wouldn’t want my son to go through some of the same things I went through. But it kind of built the person that I eventually became.

george grombacher 9:53
Yeah, it’s an interesting thing, right? Certainly, some of those experiences you just listed out you wouldn’t wish upon that. Anyone, yet? It’s certainly played an important role, you wouldn’t have arrived here any other way. So it’s an interesting thing. So here you are now, you’ve, you’ve now written a book, you’ve started these different businesses, you’ve had all this success. Do you still have this chip on your shoulder? Is it bigger? Is it smaller?

Jonathan Beskin 10:29
Yeah, I definitely still do. And I wouldn’t really say it’s necessarily bigger, I would say it’s, it’s some more or less so there. And I think the challenge is, I mean, how do you, you know, it’s not like I could flip a switch and turn that off. And I think that in an ideal situation, I wouldn’t be able to move on from a lot of these, you know, being this kind of insecure kid who was made fun out when I was younger, and who grew up in rich area that people kind of thought might have lived in a trailer park or something like that. So I, you know, it’s not easy to kind of shake that. And I wish it was because the challenge is, then it’s like, even though you prove yourself to people, there’s a constant need to continue to do that. And that’s also challenging. So I mean, it’s hard to kind of keep that up and have put pressure, you know, I already feel like I have enough pressure on myself to keep the business going, you know, with my son with anything else. So I put this extra pressure on myself about, you know, prove continuing to prove people wrong, that, ultimately are pretty insignificant in my life at this point, and definitely are familiar with some of the things I’ve achieved and that type of thing. So it’s still there. In a lot of ways. I wish it wasn’t. But I think it’s just part of my being. I think that one thing that I also talked about in the book is a whole concept of using some of these things like debilitating anxiety, and depression, and racing thoughts, catastrophe zation. And thinking a certain way, and channeling that thought process into something positive. So taking all the energy with anxiety, into thinking about your business, from every angle, pre empting, what your competitors are doing, just using those types of things that are perceived as negative in a way that could benefit you and benefit your life. And kind of not looking at as toxic because I think for the most part, when people have these things, like anxiety, even if you, you know, unless you’re like fully medicated, like completely completely out of time. I mean, it’s hard to control them. I mean, it’s not something that goes away. It’s kind of like a disease. I mean, it’s not something that that like easily is is solvable. So you’re gonna have it and you know, it’s not going away, why not try to use it to your advantage?

george grombacher 13:06
Yeah, I certainly appreciate that. And you feel that that’s a skill, like any other meaning that you need to learn it, and then you can get way better at it?

Jonathan Beskin 13:21
Yeah, I think that, yeah, I think you need to, in a way, it’s like retraining your brain to, you know, of how to process things. And not you know, a lot of people I think, or at least me, and I think I’ve spoken to a lot of people that feel this way, I mean, get mad at themselves for thinking this way, or kind of get overwhelmed or different thing. But if you can really, you know, kind of teach yourself or constantly remind yourself and that, you know, you can really use this to your advantage that you can, you know, take these racing thoughts and think about things that that, you know, benefit you so you’re not going down those really toxic rabbit holes, that don’t lead to anything positive. And you make a lot of assumptions. I mean, I could do like, you know, just give like a kind of simple example, I just thought of like if you you know, if my son is very big athlete, like has an injury to his finger, or something like that, and he has to be out for a few weeks, well, then you’re already assuming he’s never going to play college sports, he’s going to be done he then kids get injured all the time. So it’s like, you know, not not everything when when you have an intense amount of anxiety, it’s very easy to just quickly go down these rabbit holes and quickly catastrophize everything. And I think there are ways to retrain your brain to not allow that to happen, and to focus those thoughts on something more positive like a business, like achieving goals like weight loss Last are eating healthier, you know, things of that nature. Before I had this business, I was a serious marathon runner. And I applied a lot of the same principles involving discipline and sacrifice. And you know, the thought process into that at that time.

george grombacher 15:19
I appreciate that very much. So, what are you hoping that people are going to get when they get out of when they read the least likely millionaire?

Jonathan Beskin 15:30
Oh, well, I hope that they get some inspiration. And I hope that it motivates them. I think that a lot of people feel stuck in their current work environment, in their current familial environment. And that, you know, they kind of hear from my story that, you know, that, first of all, that’s very common to feel that way. And that there are things you can do to get out of that and get out of that kind of funk. And the book includes it, you know, it, a lot of it is my story, and how I kind of grew up some specific thing that happened. But there’s a lot of key takeaways. And there’s definitely quite a few actionable steps that people can take to really change their life in meaningful ways. And some of them are what I was talking about around healthy obsessions, which is kind of what I call, you know, read retraining your brain to obsess, if you’re gonna obsess in general, why not obsess on something positive, that’s healthy, that’s going to benefit you in some way. So there’s also a lot of tips and resources on how to get something off the ground. And, yeah, there’s really not a lot of negative consequences to trying something and kind of learning from it and starting off as a side hustle. So I’m excited about the book. I’ve gotten a lot of good feedback and some really high quality, unbiased reviews. And I’m excited to get in people’s hands very soon.

george grombacher 17:09
Yeah, excellent. Talking about different things that we struggle with mistakes that we’ve made is not an easy thing. Is it now easy for you? And when did you start talking and telling people the things you’ve struggled with?

Jonathan Beskin 17:31
Well, it’s definitely not easy. And writing this book was definitely very emotional and brought a lot back. And I think I, you know, particularly as a relates to some of the mental illness, things that I talked about in the book, which also includes when one of those times I was hospitalized and don’t having electro convulsive therapy for severe depression. I think that a lot of people who know me personally would be very surprised to hear that I think I’ve been good for a lot of my life about putting up a front or a mask and feeling horrible on the inside, and really struggling on the inside. So I think it’s very vulnerable kind of situation. And I’m very transparent about a lot of things. But I think the more people I’ve spoken to about this, and as I’ve been talking about a more, you know, conjunction with releasing the book, I mean, a lot of people relate to that particular as it relates to mental illness and anxiety and depression, whether, you know, they’ve had something as serious as being hospitalized, or more likely, they just struggle with this on a daily basis, and kind of with the normal stress that’s associated with, like everyday life. So I’m really hoping that aspect can help people too, and being willing to share something like that, that I just think a lot of people aren’t willing to talk about.

george grombacher 19:02
Well, I commend you for it. And I am grateful that you did it, and that you had the courage to do it, and that you continue to have the courage to talk about it, because there are so many people that are struggling with it, and to see somebody who has experienced the kind of unique success that you have, and the experiences that you’ve had. And it’s, that’s really oftentimes what we need as human beings is to be able to look and see oh, look at Jonathan. He’s just a regular guy who’s done extraordinary things. And he struggled with a lot of the things that I have. So perhaps I can do that. Also. I think that that’s a really, really cool thing. So thank you for doing it.

Jonathan Beskin 19:44
Yeah, well, thank you and I hope more people will have the opportunity to kind of hear the story. And yeah, I’m excited to do more things like this and get it out there as well. Much as I can.

george grombacher 20:01
I love it. Well, Jonathan, thank you so much for coming on. Where can people learn more about you? How can they engage? And where can they get their copy of the least likely millionaire how to succeed when everyone expects you to fail?

Jonathan Beskin 20:14
Yeah, so there’s a few ways to connect with me. I have their website, it’s Jonathan best skin.com. That’s J O N A tha N. B like boy Esk. I n.com. I also, you know, have an Instagram account at J Bescot. My last name Baskin. And this is very embarrassing for my 14 year old son, but kind of a tick tock account that’s gotten somewhat viral. So I have about 45,000 followers on there. I’m somewhat regularly putting out content and about entrepreneurial topics, my story, things that could potentially help. So at tick tock at Jonathan Baskin, so yeah,

george grombacher 21:03
excellent. Well, I certainly can’t wait to embarrass the heck out of my boys are six and three. So I’ve got a couple of years before they start feeling that way, but I look forward to it. If you enjoyed this as much as I did, so Jonathan, your appreciation and share today’s show with a friend who also appreciates good ideas, go to Jonathan baskin.com jon@hanbskin.com. Find them on Instagram at Jay Baskin and Tiktok at Jonathan Baskin, and then pick up your copy of the least likely millionaire wherever you buy your books, and I’ll link all of those in the notes of the show. Thanks. Good, Jonathan. Thank you. Till next time, remember, do your part by doing your best

Thanks, as always for listening! If you got some value and enjoyed the show, please leave us a review wherever you listen and we’d be grateful if you’d subscribe as well.

You can learn more about us at LifeBlood.Live, Twitter, LinkedIn, Instagram, Pinterest, YouTube and Facebook.

Our Manifesto

We’re here to help others get better so they can live freely without regret
Believing we’ve each got one life, it’s better to live it well and the time to start is now If you’re someone who believes change begins with you, you’re one of us We’re working to inspire action, enable completion, knowing that, as Thoreau so perfectly put it “There are a thousand hacking at the branches of evil to one who is striking at the root.” Let us help you invest in yourself and bring it all together.

Feed your life-long learner by enrolling in one of our courses.

Invest in yourself and bring it all together by working with one of our coaches.

If you’d like to be a guest on the show, or you’d like to become a Certified LifeBlood Coach or Course provider, contact us at Contact@LifeBlood.Live.

Please note- The Money Savage podcast is now the LifeBlood Podcast. Curious why? Check out this episode and read this blog post!

We have numerous formats to welcome a diverse range of potential guests!

  • Be Well- for guests focused on overall wellness
  • Book Club-for authors
  • Brand-for guests focused on marketing
  • Complete-for guests focused on spirituality
  • Compete-for competitors, sports, gaming, betting, fantasy football
  • Create-for entrepreneurs
  • DeFi-for guests focused on crypto, blockchain and other emerging technologies
  • Engage-for guests focused on personal development/success and leadership
  • Express-for journalists/writers/bloggers
  • General-for guests focused on finance/money topics
  • Lifestyle-for guests focused on improving lifestyle
  • Maximize-for guests focused on the workplace
  • Numbers-for accounting and tax professionals
  • Nurture-for guests focused on parenting
  • REI-for guests focused on real estate

Feed your Life-Long Learner

Get what you need to get where you want to go

Rate it
Previous post