July 2023
He is now Head of Legal at Galileo Financial Technologies and recently published The Path: A 30-Day Guide to Building a Meditation Habit That Will Change Your Life, a book on how he has become more present and peaceful in his daily life. Joel emphasizes the importance of mental fortitude for entrepreneurs and business owners. He discusses the need to have self-trust and confidence as you develop your career and pitch ideas to peers; it’s natural to feel afraid sometimes, but Joel encourages listeners to trust that they can ultimately persevere even if they don’t have all the answers right now.
Furthermore, Joel shares his experience with meditation and journaling. These practices helped him manage his anxiety during the pandemic, leading to an incredible transformation in his mental health and perspective. He also highlights the importance of having a solid support system and keeping people in your life who can provide valuable feedback and support (both professionally and personally).
Finally, Joel advises business owners to define their core values as these shape not only their company’s direction but who the company grows with. He also reminds owners to evaluate what their market wants; sometimes, even a great idea that is executed perfectly does not get picked up because the audience or market does not want it. Make sure you do a proper analysis of the products your audience wants and the problems they most desperately need solved.
Watch previous episodes of The Ripcord Moment:
Ep. 29 Finding My Identity After Selling My Business
Ep. 28 Going into Business with My Best Friend: Meli's Cookies
Welcome to The Ripcord Moment. I'm your host, Joe Seetoo. Today we're joined by Joel Sherwin. He is an experienced attorney. He's a fintech leader and now he's actually a published author as well. Joel, welcome to the podcast. Really looking forward to our conversation today.
One thing I want to mention about Joel is that he is really passionate about building financial products that really improve the lives of millions of people. You were the head general counsel at Dave, which is a fintech platform, and I think there's something over 11 million users since 2017, from what I understand. And now you're with a company called Float Me.
In addition to that, in between sort of your stints, you just recently published a book, 30 Day Guide to Building a Meditation Habit that Will Change Your Life. So talk a little bit about that. And welcome to the podcast.
I appreciate it. Yeah, a couple of quick notes. I was the general manager management before they got Dave and yeah, the book, the Path The 30 Day Guide to Building a Meditation Habit that Will Change Your Life.
So yeah, I'm excited to be here. It's great to see you.
So, you know, you, you are you've got a lot of different skill sets. But I know one of the things you're really passionate about is this idea of entrepreneurship, business owners and the things we've actually been talked about in the past is we see their successes, right?
We see the things that when we think of entrepreneurs and business owners, we have a level of success. We see sort of the finished result oftentimes. And so we kind of tend to look up to that. But you you've shared with me some of the struggles you know, you've had and what you've seen with other colleagues and what is it that we don't see from the outside looking in?
Well, there's a lot that we don't see. You know, I think you don't see the failures really. That's the thing that I think young entrepreneurs. But really any entrepreneur has has gone through is the trials, the tribulations, the things that don't work, the perseverance, the pivots. You think, you know, you're going to go in one direction and it doesn't work.
Or, you know, you I mean, you have to make some series of decisions that ultimately leads you to where you are. I mean, the famous example is, you know, Amazon started as a bookseller, right? Right now sells everything. And, you know, I know for me, you talk about trials, tribulations, challenges is, you know, I, I think I have to have the answer before I start.
You know, And the most crucial thing that I've seen successful people do is they just start they just get started. They just get started. And then they just, you know, their belief that no matter what obstacle stands in their way, they're going to find a way around or through. Yeah. So, you know, on this point of pivots, how do you you know, what do you think through and calibrate, you know, because you said that a second ago.
What I'm thinking through, like I got to imagine, is little more art than science. But how do you know when to stick with something and try one more time on it versus like, okay, we've got to scrap this idea. We have to pivot. And, you know, if there's an example you can maybe share around that.
You know, I think and even in the way you phrased it, you know, my like, what I'm thinking about right now is, is it all or none? Right. It's not a scrap or pivot. Right. Know, it's almost like, you know, what pieces of this is working is what and what of this does it you know, I mean, is it trying to tweak, change?
You know, and and, you know, I think oftentimes we think in black and white, you know, all are and on and at least in my experience, having worked with, you know, startups grow stage companies, entrepreneurs, business owners is that it's all these sort of shades of gray. Right. And and you know, they're taking what works of an idea because very rarely does nothing work?
Does no one buy your product? Right? No one sign up for your service. And so, you know, what about that works. What about your audience? Is it not resonating for and why? And then making those, like you said, tweaks and refining it. So it's absolutely it sounds like part of what you have to be really skilled at if you're going to be in this entrepreneurial path is as it reflecting back on and being able to critically evaluate, like you said, what's working and what's not working and then thinking through, okay, how can we add on to what's working and continuing to go go down that road?
I would imagine that that takes a lot of mental fortitude, a lot of being able to handle disappointment. And so what would you say is a mental formula for someone who wants to be an entrepreneur or a business owner?
I think mental fortitude, perseverance is absolutely key. And I think, you know, if I if I think back into my own experience, um, getting comfortable with the uncomfortable right, getting comfortable with this being part of the process, you know, I because you know, if it's part of the process, then these disappointments, these, you know, people from the outside may call them failures.
They're not they're just part of the prize. I saw it. And so just like when you hit a home run, running around the bases first, second, third, fourth is part of the process. Hitting a triple is not a failure. Right? Sure. It is part of the process. And so I think, you know, that's the way that I've seen it work.
That's the way that I've sort of started to train my you know, conditioned my mind to think about things that, you know, they may fall short of my, you know, expectations what I wrote down. But it's still massive progress. And it's it's you know, it's those sort of small wins that, you know, they add up to this, you know, great accomplishment at the Azure that you're looking back on that you all ultimately always wanted.
Well, what you just said that reminds me of a book I read not too long ago by Dan Sullivan The Gap. And again, I think even Rick Bregman you did recommended. I haven't read it. That's okay. You've been busy writing your own book. Yeah, but yeah, I mean, it's interesting how we write outlines some vision for what we want.
And the reality is sometimes we're not quite there. But if you don't take time to calibrate and look back at the the, you know, the gain that you made. Right, right, then naturally you'll feel like there's this, this almost failure. One of the things you've mentioned to me in the past that I think kind of ties in I'd love to get your you know, for you to unpack it a little bit more is about this idea of confidence meets determination.
What do you mean by that?
Well, I think confidence is something that, you know, historically you're told, you know, has to be earned through like your life experiences. And the the problem with that mentality is, you know what the way you feel is what the world sees. Right. And so if you're out there trying to gain confidence and I'm not saying this is the wrong way to do it, just saying if you're out there doing it and you're not getting that feedback in return, it can slow your progress.
Meanwhile, if you believe in your utmost capability to do something and that confidence grows sort of, you know, in in, in inside of you, that's what you reflect in the world. And the world starts reflecting that back. Sure. And so I think being determined, you know, everyone understands that to accomplish anything, you know, you have to have some, you know, determination, some very rarely does something fall into your lap.
Right. And certainly, I assume anyone listening to this is not that type of person to expect those things. You know, it's just magically falling from the sky. And so we already know we're going to to work hard for something. The confidence piece is that, you know, trust and confidence go hand in hand when you're trying to pitch a product, a service, design something, get people to work with you, with you.
They want to believe that you know what you're doing, even though you may be scared every day, every single entrepreneur, including myself, has been scared. No, Naturally, you know, the majority of the time. Right? Right. But it's that confidence that they have that like, I don't need to know the answers right now. I'm willing to to do what it takes to figure it out.
And at the end of the day, the only one who determines my success is me. Is me. Sure. Yeah. So let's take that or maybe a step deeper, because we're getting into a little bit about sort of your own personal journey and how you dealt with, you know, the pressure of, you know, business, a young family. You're very dedicated, you know, family man.
You also make a lot of time for yourself in terms of your own spirituality, your growth, and you're passionate about golf. This is a lot to juggle, right? Yeah. And so as a young entrepreneur, what has what are the tools that you have found that have been helpful to keep that balance in your life?
I mean, balance is tricky. It always is. It's something that every year on sort of my list of goals I put down as as a main focus because, you know, the way that I look at balance is not necessarily for a day because some days get crazy, but I sort of think like week to week, yeah, can I move the chains and the things that are important to me?
Right? And you know, so you, you definitely summed it up. I do a lot of things for my myself. I mean, you know, that I'm in recovery. I've been sober for 20 years. I, I have a certain routine that I have to do to maintain my, you know, my sobriety. I have meditation, I have journal, I have my family, two young kids and.
And then golf. Yeah. Golf is a whole other addiction, which, you know, I'm okay with made my peace with that. But it's certainly time consuming had you know I think for me I have a hard time if I try and do everything all at once. And so what I do is in my sort of daily journaling, we, you know, week to week, I think, what am I going to work on this week?
And I pick two or three things. And by the way, that's not for me. Ben Franklin talked about that in one of his books that he would have this list and and would pick a few things to work on. Yeah. So I feel like I can pick a few things store, like for example, right now I'm listening to a book about my marital relationship and I'm reading a book about my parental relationships.
So right now I'm sort of focused on relationships. I love, you know, it sounds like you've kind of gotten to a place where because I think nowadays with the amount of information that's thrown at us with just that, just the pressures of like trying to do it.
And now more and more it's shown that multi-tasking doesn't also... you know you're much more productive in sort of these you know short bursts of focus focused you know focus time and so that's that's what I'm trying to do is is to, you know, figure out and I actually talk about this in the book, you know, figure out what my most productive times are for the certain activity that I want to do.
And then I sort of double down in those times. And would you use that when you were working at like Dave or now for me, I'm assuming it's a formula use for for your business life and your personal life. When is your best creative time or when is your head in the best place to do that deep work and make sure that's when you're focused on getting those big high sort of those big rocks achieved?
Yeah, absolutely. I mean, you know, to me it's it's all about output, right? And so if you're spending, which I've done in the past and it didn't work, you know, 60, 70 hours a week working and you're just absolutely drained. I mean, not only does research show that that's counterproductive, but, you know, just the way that you feel, it's mentally and emotionally exhausting.
And so I'm really trying to, you know, schedule my time to where I can sort of maximize the output when it sounds like you're not going to be able to show up in your marriage or with your kids in those relationships you talked about earlier, you know, as your best self. I know I can do it if 100.
Yeah. Same here. So let's pivot and talk a little bit about the book and you know you've taken on a new or you did not too long ago took on a new role as a writer where I mean you were you're working, you were doing this crazy thing I think where you're getting it by like three in the morning and writing from like 3 to 5.
That's right. Okay. So what prompted this talk a little bit about the book and sort of what you learned through that process that maybe you can even apply to your your entrepreneurial life? Yeah, sure. No, and it actually it does correlate, which I'll I'll talk about. So a real quick synopsis of like the the or the my my motive for writing the book was, you know, sort of at the, you know, after year one of the pandemic, you know, I was I was really starting to feel a lot more anxious.
I wasn't sleeping well. Started to have, you know, a lot of fearful thoughts. And and, you know, this is with 18 years sober and having done a lot of things, you know, to sort of condition my mind and you know, feel centered and and with fearful thoughts. I mean, was this basically related mostly to work? Was it life in general?
Was I mean, every every you name it, you name it, I'd wake up in fear, worry and dread. Okay. You know, everything in life, everything in life. And, you know, and for anyone who's ever felt that it is, it's exhausting. You know, you wake up from sleep, exhausted. And so, you know, thankfully, I have enough experience sort of, you know, know where to seek answers and help.
And so, you know, it was like therapy. And I went back to sort of like the basics of you know, my sort of spiritual program. And, you know, I kind of found something that I had missed, which was, you know, consistency in a meditation practice. I had meditation throughout my time in recovery since I was 19.
But, you know, there's something that I had missed about, like consistency. And and it's that accumulation what I had found. And so I, I spent time starting to meditate and sort of figuring it out. And and what happened was, like this transformation, which I hadn't felt in like 15, 16 years, I mean, my whole sort of mental outlook and attitude changed as a result of it, like over how long of a period of time of meditation was this over like a month following about 90 days.
So 90 days consistently crack. It was like born. Something changed. Now, it took me about eight months to get consistent, right? But about 90 days of consistency. I had this experience where I stopped judging my practice, okay? And I stopped having expectations. And I would I would start like my mind would be quiet. You know, I also started to couple that with journaling, and journaling helped me to sort of empty out a lot of the sort of monkey mind, rapid fire thoughts that, you know, mostly are repetitive and sure enough, partially destructive.
Yeah, certainly counter productive. And and so anyway, I wrote about this experience in this book. And what happened was, is my wife and I, we we sort of, you know, sit on the couch and kind of watch TV, and then I would do my most destructive habit, which is snack. I'd literally just sit there and I just eat for like 2 hours before I go to bed.
It'll look like, well, I appreciate that. But it was like, Oh my God, I got to do something. And so I basically, you know, I had heard Mark Wahlberg had this crazy schedule mean, you know, shout out to Marky Mark, right? And that he would wake up early and do cardio. And so I just said, you know what?
I'm going to start going to bed earlier and I'm going to wake up early and I'm going to see what happened. It wasn't like I'm going to write a book, right? And what happened was that I would wake up, I'd I'd be inspired to write to write this sort of this story that I feel truthfully could help other people, you know, which is always been something, you know, whether we talk about building financial products or, you know, talking about meditation is something that, you know, as was near and dear to my heart.
It's part of my DNA. And and so I did and I had this experience as I was writing the book of sort of being, you know, going from this fearful time in the morning to this really sort of, you know, introspective, knowing miss. Yeah, you know, in the morning peace, you know, very peaceful, you know.
And I just I just loved it. And before I knew it, you know, I had had this story that I wanted to tell and and the way it's connected to entrepreneurship is, you know, the most important thing you can do is start the next most important thing you can do is keep, keep going. You know, and I've started a lot of things.
I've got, you know, and look, you know, probably the most expensive real estate is is the graveyard of ideas that have never been finished. Sure. You know, and I have that. And this there was something profound in actually getting this book published and putting it into the world. I mean, like a sense of accomplishment that you start, you know, A to Z got through something.
Yeah, yeah, yeah. Okay. And, you know, it hasn't been that long, right? We're sitting here, it's in February or end of January. And the book, you know, was published in December and so, you know, that experience is still working on Michener, naturally. But I'm really optimistic and hopeful that that this will be a sort of springboard in my own adolescence and my own entrepreneurial journey to take on the next challenge, I'm sure.
Well, let's let's review the conversation. You mentioned something in one of our conversations about this myth of being lazy and downtime. Oh, I kind of want to just spend just a minute or two kind of your thoughts on that.
Yeah, I mean, the hustle culture, right? Hustle porn, like the whole idea that you ever heard that one, you know, this whole idea?
Well, you know, that that that comes from like the Instagram where you see, you know, the guy like, you know, grinding all day and, you know, like the naval Ravikant talks about it. He he says that, you know, he does that what he loves, he does for 16 hours a day. And so if you're, quote, working, you're never going to be able to compete because he's literally just living, living and he's turned his, you know, his passions into his life.
And, I mean, look, I think that's great. I certainly we all pack a lot in, but like a perfect example is, you know, I woke up for eight months at 3 a.m. to write this book. And now that it's done, like this year, I've sort of been like, quote, sleep again until like, you know, my kids get up at 530 or six or whatever.
And it's really easy to to turn, you know, the attention on myself and get over the critical and say, you know, what am I doing and all this stuff when the reality is I just needed a break. I just needed a break, you know? And so I think this idea, it's really honoring yourself. It's really knowing yourself, knowing you know, what you need, honoring that.
And by the way, I have only figured out how to be kind and empathetic towards others when I am kind and empathetic towards myself, give myself grace, be forgiving of myself, and to be honest, like really understanding where I'm at, you know, one of the especially as a man, I don't know. It's hard sometimes to answer the question, how am I?
Yeah, right. How are you, Joe? You know, and so, like, you sort of pause. I and so but you're deeply honest when when it comes to that I've even those that are interactions I try tears no absolutely are where I think so many of us when we're when we're talking to people who are maybe not deep friends, but acquaintances, we naturally just say, I'm fine.
It's great. I was a week and I was great. Rail You kind of sort of gloss over those things. Let's take this maybe a step deeper, though, in terms of your support team, your wife. Jen's actually here in the studio with us listening to this. You talk a lot about I think it's something we all get the importance of surrounding yourself with the right support team.
I think it makes sense in business, but for you, it may be more targeted, but about personally, like what is what does that look like? I mean, you're you're on that team, too. Well, for sure. I mean, I'm you know, we've had lunches in the past where we, you know, bounced ideas off each other. And it's it's a two way street.
And I certainly, you know, value our I think, you know, that's really that's what support means. It's it's finding people who you can both give and receive. You know all my relationships I'm never looking at my relationships as what can this person, you know, give to me. I'm always looking at, you know, who is this person? You know, how how can I, you know, add value to their life?
Hopefully, you know, they add value to my life. But, yeah, I mean, you know, certainly asking for help is very difficult just in general writing from a lot of people. And I think, you know, cultivating relationships for people who have done what you want to do or who even you know, I have a friend who who started a massive clothing brand and sold it.
And, you know, I was kind of having some ideas about clothing over there, I guess, last summer. And, you know, just to be able to call him in and just sort of bouncing his brain. Yeah. Down some ideas off, Hey, does this make sense? Am I even, you know, in the right ballpark here? It's great. It's great.
So, yeah, I think for for folks that don't have that, I think, you know, start with like what can you give right. Who who can you identify in in sort of your immediate surroundings or people who know people and find out, you know, how it make those connections? Yeah. What adds value to their life? Sure. You know, is everybody that's the thing too, is we so undervalue our contribution, our abilities.
Right? We are unique. Early here, you know, for the ability to to solve problems that like we are, you know, we as individuals, you know, have a perspective on. Right. And so I think I know for me I've I massively undervalued at times hopefully not as much currently. You know what you know how I can how my unique perspective based on my experiences can help help somewhat.
So talking about unique perspective, what are the lessons you think you've learned at day that you carry with you to float me on a go forward, you know, to to lessons you that you know, I think number one is is people matter like the people around you, the team that you're building. It's so important to no matter how fast and in startup or growth you know stage business is maybe in any business sometimes things move so fast that it's almost like an afterthought to make sure that the people who are helping you move as fast as you need to are taken, taken care of or the right people.
Yeah. And so I think that's a big lesson for me, is that I am you're never going to get to where you want to go a lot. Sure. Right. So make sure you got the right people around you and you take care of those people sort of through the process. Second thing I probably learned that I'll take with me is I mean, I learned for me, you know, what my strong suits are.
And and and I think, you know, one of them is is investing in other people and having them ultimately, you know, kind of that's the definition of leadership in many ways. Right? I hope so. Yeah. You know, so envelop their own their, you know, new skills and take on new responsibilities and elevating them to a level that perhaps they would have gotten to on their own.
And you're helping to be that catalyst to support them. Yeah. Yeah. No, I think that's right. And that's certainly the way I think of leadership. And so I think becoming a I certainly learned a lot about myself as a leader and, you know, where I needed to spend more time on and, and I could tell you, I mean, for me, the thing that I learned is that, you know, I, I sometimes want to be, well, well-liked and and, and so the ability to develop, you know, the the the respect and also the the clarity, see people who have clarity.
Right. And and even if it's not the direction that they want or they disagree, it's clear and it's well explained and, you know, well intentioned. Yeah. You usually can can, you know, align hearts and minds in that direction. They're going to be receptive to the input. Yeah. Versus sort of like not really wanting to say because you know it's not the popular, Right.
Well Joel, we call this The Ripcord Moment because I believe when an owner entrepreneur thinks about some sort of succession event, right, they've got to have their parachute pack out of the right, people packing the parachute. I always ask our guest for two action items. It could be things that we even covered in this conversation for, you know, entrepreneurs maybe that are in growth mode, that are thinking about scaling and or at some point going to have some sort of succession event. And so sort of what are your two critical takeaways that our audience should think about as they're growing their businesses?
Well, I think the first one is define your core values. I think that shapes not just the company. You know what the company sells or what the company does, but I think it also shapes who the company does it with.
Right. Whether it's the target audience for the folks that are building it with you. And I think, you know, when you when I think of really strong brands or, you know, companies that have have lasted, you know, and met that the test of time and it's those that that have a clear vision and have sort of a clear core values that they live by that they hire, that's part of their sort of ethos, how they operate.
Yeah, it's got to be authentic. Oh, right. And usually starts, you know, at the top and but what's what's really cool and I mean Netflix for years was was touted as you know having a very strong culture and I've read their culture document and you know they talk about it's not for everyone and those that it's for tend to be, you know, passionate protectors.
So they buy into they buy interested. And if they see its not being upheld, they will they will address it themselves. Yes. And so it's very self-regulating. I like that. Yeah. And then the second one I would say is, you know, before you you know, before you build it, right, make sure what you're building is the right it that's not mine.
It's from a book called the Right It. And but I found it's so interesting because the book starts out with the premise that a great idea is not enough. And I'm and I'm sort of nodding along and I say, yeah, of course you've got to have right execution. But then he follows it up. It's a great idea. With the right execution is not enough.
And that's what really stopped me and then gives you examples of like Google has a whole graveyard of, of, of like broken Burroughs fail products. Pepsi had clear Pepsi which didn't work. Right. Right. And he said it's not because those folks didn't know technology or didn't know beverages. It's that their audience didn't want the market didn't want it.
The market didn't have. And so it's really gotten me to think and you don't want to think. It's not like you know, analysis paralysis for and. Yes, right. But, you know, it has gotten me to think a little bit about, you know, do I understand? Am I trying to solve a problem that exists? Do we understand the market?
Am I trying to solve the problem in a in a way that you know, that the market wants it solved? I mean, it's I love I love what Steve Jobs said so many years ago where he's like, you know, we're building things that people don't even know they want. Think that's amazing. But like for the majority, you can still have a great product and a great entrepreneurial story that's very successful with building things that people do know they want in a way that they've told you they want them kind of thing understate understood.
So, well, let's go and wrap it up. If the audience wants to get a hold of you reach, you find out more about your book. How could they go about doing that?
Joelsherwin.com. I'm on LinkedIn.
Joel, thanks for being with us and it was a great conversation.
