Ep. 40- Jeremy Segal "Why Influence"

In this episode of the You Winning Life Podcast, host Jason Wasser, LMFT, interviews entrepreneur and podcaster Jeremy Siegel. Jeremy shares his journey from aspiring CFO to serial entrepreneur, highlighting how he repeatedly needed to give himself permission to pursue entrepreneurship and to share his voice publicly. He discusses overcoming introversion through Toastmasters and mastermind groups, building a personal brand that amassed over 200,000 organic followers, and launching the "Why Influence" podcast to help others share hidden knowledge. The conversation covers practical tactics for content creation (video vs. audio, re‑editing, challenges), handling criticism and trolls, and advice for introverts on taking the first steps. Jeremy also reflects on the dynamics of an entrepreneurial marriage, the value of strategic retreats, and the importance of discovering and evolving one’s “why.” The episode ends with actionable tips for building a YouTube channel, guest outreach, and a call to listeners to support both podcasts.
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This is the You Winning Life Podcast, your number one source for mastering a positive existence. Each episode, we'll be interviewing exceptional people, giving you empowering insights and guiding you to extraordinary outcomes. Learn from specialists in the worlds of integrative and natural wellness, spirituality, psychology, and entrepreneurship so you too can be winning life. Now here's your host, licensed marriage and family therapist, certified neuro-emotional technique practitioner, trainer and certified entrepreneur coach, Jason Wasser.
All right everybody, welcome back. Today I have an incredibly special guest. It's someone I met this past summer at Podcast Movement in Orlando. And one of the awesome things about the weekend was that this next guest actually spoke for one of his first times on a larger stage in front of, I would say there was probably about 200 people in the room at that time. And he's an entrepreneur, he is a podcast host, he is in this really awesome marriage with his wife Crystal, who I had the pleasure of meeting 2 weeks ago on my How I Show Up retreat with my buddy Pablo. And I want to welcome Jeremy Siegel to the podcast today.
Thanks, Jason, I appreciate you having me here. I'm excited.
Me too. So I know this is probably a long time coming, and since we're both on forced quarantine and We just came across, right, came off this 2-week ago, almost, well, week and a half ago, almost 2 weekends ago, retreat together. It's a lot of good stuff is buzzing around in both of our heads.
Yeah, for sure.
So before we go into some deeper dives on the things that I want to extract from your head, because I know you and I have had some really awesome conversations, just kind of give us a quick little background on where you've been and where you're hanging out right now so people out there can get to know you a little bit.
Sure. Well, my name's Jeremy and I always wanted to be an entrepreneur, so I always aspired for that. And to be an entrepreneur, I always thought the skillset of a CFO was the knowledge base that I wanted to have. So I had a clear vision of that's where I wanted to go. So in college, I did accounting finance, did information systems in grad school, Got a job at a Big Four accounting firm, saw that I wasn't really getting the skillset that I wanted, then went to implementing cloud accounting softwares for small companies. And then I got an opportunity to be a CFO of a company with 130 employees where I oversaw the accounting, finance, HR, marketing, and IT departments. So I was doing that by age 25. And so at that time, I had done a couple of ventures before. I always bought and sold stuff. I was always entrepreneurial mindset, but I never gave myself permission to be an entrepreneur. And so once I was CFO, gave Gave myself permission, started a business, built a business, sold it, started another business, currently have it. And I did all this without sharing. I didn't post online, I didn't share. My business would get featured on the news, grew over 200,000 social followers in my business. And anytime I was in a picture or video, I would edit myself out. So started going to Toastmasters, doing mastermind groups, started seeing value in my voice. And then It was the second time I gave myself permission for something big, which is to give myself permission to have a voice. And that's when I started my podcast called Why Influence, where I'm asking influencers about why they're sharing.
Awesome. So there's something that stood out to me from what you're saying, which is this constant theme that I see showing up in my therapy and coaching practice is us giving ourselves permission, or that we're waiting for other people to give us permission to do something that might be our purpose and potential. So With your permission, could we delve into that for a few minutes? Because I think this is a really amazing topic, right? Where I joke around, right? You know me in person, so you know I'm not the world's tallest human being. And I most recently been joking around with people that I'm no longer willing to play small, right? And all 5'2" of me, right, in human reality is, you know, is not the world's tallest guy. So, but the mindset of like me being in my therapy practice in my back office here in Hollywood, Fort Lauderdale area, people don't know me unless, like you said, like you build You build up a social following, you get out there, you speak. I know one thing that we both have in common is that we're both introverts, which we're going to get into later on a little bit more about overcoming the barriers of sharing our stories. But I want to first start off with this idea of giving yourself permission. What was that process like for you? What did that look like? What was the dialogue going on in your head?
Yeah, for the entrepreneurship, starting a business, giving your permission, it was like a mental block. I started the business after being a CFO. I had, back in elementary school, I was buying and selling things. In middle school, I would sell golf balls off the shelves at Walmart, and whenever they sold, I'd get my parents to drive me to Walmart to go ship them out or sell Pokémon cards. And then high school, buy and sell cars, or college, same thing. After college, when I was working at accounting firms, I did a charm website, which I did with a friend. We got up to about $3,500 a month in sales just with these little charms or paracord bracelets. I sold masks, like Halloween masks. I got them into Halloween stores, sold them at comic conventions. I started a paint pigment brand and I did all that just with this mental block, like I can't go big in it, I can't go all out because I'm waiting to get to the experience that I want. So I've just been aspiring to get to the CFO position. And the knowledge and skill sets to get there. So it acted like a mental block. And for the sharing part, I didn't even know it mattered that I wasn't sharing. To me, like, I was just quiet. Like, I didn't care to not share. I didn't see the value in it. I didn't really understand why other people cared that much to do it. So like, first I had to build awareness for it because I lacked that. And then once I started realizing that there was value there, then I saw that the mental block was there, and then I had to intentionally pursue ways to overcome that.
So not seeing value in yourself, right? And I wonder for people out there who are listening, where that shows up for them in their lives, where they have this like doubt or belief about themselves, right? Where they might see that they don't bring a particular skill set or a particular value, a particular emotional set of values to the table. So is there something that you remember, like in your mind, that like turned that light switch for you that allowed it to go from the self-doubt to being able to start putting yourself out there? Do you remember a memory? Do you remember a thought? Do you remember a feeling? Do you remember like, "Man, I'm done doing this"? Was there anything like that that went on for you?
I don't know if it was a moment as much as just the whole journey. I mean, so I met my wife, at the time girlfriend, about 8 years ago. And the first gift she gave me for my birthday was a check to join Toastmasters. So that just explains, I'm already not talking to a lot of people. I don't text with people, I don't call people. If I'm not interacting with you in person, you're not hearing my voice or interacting. And it took me 4 years to cash that check. So I didn't even see value in it. I didn't care, but I kept the check. I was like, I'll do it one day. And at the same month, I joined a Toastmasters group and a mastermind group. And in the Toastmasters one, it gives you opportunities to stand in front of a small group and speak. So overcoming those just barriers and speaking in front of groups. And then the mastermind is more intimate, but I found that I could help entrepreneurs get leaps in mindsets very quickly with short conversations and hold them accountable to the next steps that are necessary for them to take. So the combination of speaking more and then seeing the value in my voice, I think just that whole journey. And then on top of that, I've built and sold a business. And then when you sell a business, you start from scratch again. And then I built another business I've got over 200,000 social followers that I've built. And I just think when I sell that or liquidate it, uh, you know, I'm just starting from scratch again. And so like, I think that there's some value to have a personal brand that gets carried with you through the process.
Right. And, and, and for those out there, right, to build a 200,000 follower list is not an easy, easy job, right? If we're talking about like organic followers, we're talking about engagements, we're talking, you know, and I know a lot of people out there, especially if you're in the social media world that there's, there's ways of getting people to follow you. Um, but you're talking about like you had a dedicated community of people based on, on your interactions and your experiences from there, from, from any of the businesses that you've had.
Yeah. I mean, it doesn't have me in it. It's not my personality, but like I've managed it and I've taken the pictures. I've made the videos, uh, for the most part. And, uh, you know, it's just been organic over time. And, you know, as of more recently, I've done a couple It's a car brand, so I've done a couple of car test drive videos on YouTube. I did one clip on Instagram where I showed my face and in like 2 days it got like 8,000 views and I was like, "Wow, you know, like I've never shown my face here and it got that." And same with YouTube, like there's less of an audience there. I think we have about 15,000 subscribers on YouTube, so the video's got like a couple thousand views, but for, you know, it took me a lot to be willing to put myself out there on that.
And what's so interesting for, just to be really timely, yesterday I sent you a text message, right, into our group from the retreat, and I'm like, "Does anybody know the difference between this platform and that platform?" And you're like, "Hold on one second." And then like 15 minutes later I got this YouTube video, right? So, right, there's been so much stuff to hear this journey of like, I was afraid to put myself out there, to you now making demonstrative videos, doing comparison contrasting for all these different things, whether it's social media tech or your car. I want to really have people out there hear that if you practice something with momentum over and over again, just like Jeremy's doing, you will master this skill set even when you think it's something that you are petrified of or it's not something authentically yours, right? They weren't born with that gift, the gift of gab or the gift of, right? Not everybody's going to be Tony Robbins or an Ellen or an orator like Barack Obama or someone who's just a great public speaker, but this is a practice skill, and Toastmasters is one of the things that you really invested in.
Yeah. Speaking in front of a couple people up to maybe 5 or so, I could talk to anybody even if they're really intimidating, I had no problem. But when it got to a bigger group, even at an entrepreneur event where I've already started, sold the business and have another business, if there's a large group and they're asking a question, I just start sweating and get nervous. And when I spoke at the conference where I first met you, when I got off the stage, my hands were shaking. I texted my wife and You couldn't even read the text what I sent. It was just a bunch of random letters like smudged together. You know, I'm still like on that journey myself. And the video that you just saw was the first one that I did on my Y-Influence brand as a challenge. I just keep getting challenges from people. So someone's like, I challenge you to do this, or I challenge you to push yourself to this. And I just keep accepting those challenges. And so the video I just sent you was a recent challenge from a friend. He's— he asked me to make this video because he uses StreamYard a lot, which is a livestream software. And I was telling him things that he didn't know about that and the comparison of that to Zoom.
Yeah. And it's so cool, like how when you specifically have found a niche and how to help people within that niche, that you're going to get traction by that. And this is— last night I did a group call for a local organization here and it was how to manage stress during what's going on around us. And one of the things I kept reiterating was We're going to see new problems that are going to need to be solved after this pandemic. You might be uniquely positioned to solve that problem. Do you have the foresight to think ahead of what might come out of this in the next little bit and how can I, or is this an area that I've always been interested in, but there was no space for me to jump into for that? I think that whole theme of your podcast and your brand of the Why Influence, like what's the reason behind, what are you taking about your personal stuff and putting it into the world and how you want to connect with people? Is really, really cool. And I know one of the things I actually wasn't thinking about discussing with you, but maybe we can talk for a few minutes about starting this brand, right? If you build something where you have so many followers and you built a dedicated YouTube page, right, is there something, is there maybe 2 or 3 tips that you would recommend to people out there that if they're, let's say, just trying to get on YouTube, right, do they do it from their personal name or do they create a separate account that's just the business, you know, whatever it is, that brand, or, you know, or is it a channel under their own name? You know, how would you, how would you suggest that they set that up?
I mean, I think it depends on what the goals are and what their reasons are. Uh, so if they got a business and they're trying to build a business as a standalone entity, then it should be in the business. You know, if it's to build a personal brand and the business sort of tied to you personally, then I would, uh, I would consider either having it in the business name, but the business name being the same as you, or making it under you so you don't have two separate things because they're both basically the same thing. And I think that it's, you know, building a personal brand is pretty important. And that's part of the reason why I'm pushing myself to overcome a lot of these barriers is to, you know, be able to do that.
So any insights on those out there that would be self-described introverts? What would you say would be like the top 2, 3, 4, 5 things that work for you, right? It's not going to be a catch-all, but that worked for you, that helped you go, right? I know Toastmasters was a big thing. It also helps that your wife is a public speaker, right? So I'm sure there was some good influence on that part. But what were some of the other things that you would say like, "Guys, if you're listening to this and this resonates with you and you are an introvert, here's what you absolutely completely need to do." Yeah, I mean, I think that the first thing is just you need to get started and take action.
And you can record videos and just do the videos but never post them. You don't even have to watch them. You could literally just delete them after doing the video. You don't have to post it online. So there's no pressure when you're just creating a video like that. But if you're not comfortable being on camera, then you can do a podcast. I mean, for me, I started with podcasts because I didn't want to be on camera.. And that's my easiest way through. And my first 3 episodes, I gave myself permission to re-record myself in post-editing every time I spoke. So I literally would just ask a question, get an answer, ask a question, get an answer, and then post-editing, ask that question more confident and concisely, and then insert it in. It's a lot of work. I wouldn't suggest doing it long-term, but it's a good exercise to get me going. And in my episode 0 of the podcast, I suggested that people start the most recent episodes so they don't have the pressure of people always looking back at my early ones, I can feel like, okay, they're gonna jump to the more current stuff. So just like, I mean, there's endless things. I mean, I talk a lot about this on the podcast, so I don't mean to plug it, but like just checking out some of the episodes on my podcast. Like I ask everyone that I talk to about what kind of barriers they've overcome to share. And there's been, I've had people like Mark Metri who he would literally go on the street and just talk to, approach someone and ask them for what time it is. And he would do that to 10 people a day. And then the next day he would go to 10, or whenever he got comfortable with that, he'd go to 10 people and say, "What time is it?" And ask directions for somewhere nearby, even if he knew where it was. And so like this conditioning of getting out there and talking to people, there's lots of different methods you can do. But yeah, I guess that's my thing.
So you said like, "I don't really wanna do a shameless plug for your podcast, but I'm gonna do it right now." Guys, if you're listening and you're not driving, or you're at the next red light, as long as it's safe, and probably since no one's really driving anywhere right now anyway, if you're listening to this time when everybody's kind of on home quarantine, please download Y-Influence. It's on every platform, right? It's on YouTube. YouTube.com/c/, or /c/yinfluence, and subscribe. There's some really, really awesome episodes, some incredible conversations exactly like Jeremy just described. So I'm gonna take the opportunity to do a shameless plug for you while we're here. While we're amidst this conversation.
Well, another thing that comes up is like, just, you have to ignore the trolls or the people that are going to talk trash or talk negatively because putting yourself out there is being vulnerable. And the people that are trash talking you are doing it because they're not vulnerable themselves. And if you keep pushing through it, I've found that, you know, those people tend to grow out of that or go away. I had talked to David Patterson. He's got a YouTube channel called That Dude in Blue. He's got over a million YouTube subscribers. When he was first starting out, he created a car review video, posted it to his local car forum, and he got nothing but backlash from his entire community, all the people he respected and loved, and all these people trash talking him. Fortunately, he talked to his dad about it. His dad's like, "Are you going to let these people stop you from doing what you want to do?" and helped push him through it. So he pushed through it, and now he's got a YouTube channel with over a million YouTube subscribers. You don't know, you just have to keep going and push through. Right.
I think the best person who's really good at handling that is Gary Vee because he gets so many people who are haters like, "Oh, you just like whatever, blah, blah, blah, blah, blah." He just runs back at them with mad empathy and just like, "Sounds like you really need a hug," or, "What's going on in your world?" He literally just positions himself into a place of— One of the terms that we learned in my in my master's degree was that as a therapist, we should be one down. We should always one down ourselves to be asking the questions and not being the expert. And we, although we're experts in process, but we shouldn't be experts on a person's life. And that's why we should ask a lot of questions. But I think Gary Vee's amazing at that, of taking the one down position and being like, "Huh, so what's really going on for you?" Right, exactly like you're saying, like these haters out there, they don't have the balls to step up and put something out there themselves. What I'm realizing more and more is that whatever unowned personality trait of themselves that they have not yet worked on, that they see someone else doing really well, is what they're going to call crap out on because it's an unowned, unfinished part of themselves. It's really a mirror.
Right. Yeah. I mean, I couldn't agree more. I mean, just the other day I talked to a guy, James Horton. He's got about 130,000 YouTube subscribers. About 175,000 Facebook. He's got half a million on TikTok. He's been tackling that hard and he's got millions of downloads on his podcast. So this guy's been putting himself out there a lot. And he says, "If you're not getting hate, you're not going big enough." There's going to be people out there that hate on you no matter what you do. So if you're not getting that, then just go bigger because you're just trying to get to the point where you start getting that. Yeah.
There's a great Grant Cardone clip. He was speaking at Nova Southeastern University, I'm assuming in the business school. Nova happens to be the school that I graduated from, my master's from, and he was talking about a 4-step process. I'm assuming this is probably within a year or two after the 10X Rule came out because it looks a little bit dated. He was talking about the 4 steps of getting noticed. He talked about if you don't have haters, you're not doing a good enough job of putting yourself out there. The story that he specifically told is that he had a homeless guy come up to him and The guy's like, "Ah, you got a quarter, you got 50 cents?" And he's like, "No, I don't have a quarter. I don't carry that small." He wasn't being arrogant or cocky, despite knowing Grant's personality. He's like, "Dude, stop asking for a quarter and stop asking for 50 cents. Ask for 100." Don't shower, don't change your clothes. That's part of your brand. You're homeless. But you're more likely to get a $20 bill or a $10 bill or a $5 bill if you ask for $100 than if you ask for a quarter, because ain't nobody carrying change around anymore. So don't do anything different, just have a bigger ask.
Yeah, right.
And it was like the most brilliant thing in the world. And I really— I've been doing that a lot the last couple months. And whether it was sticking in my mind from when I first heard that speech, or all the other people that have been influenced on me, is like I share this with my clients all the time, especially when it comes to giving yourself permission, that whole theme. I always ask the question, and I'll ask it to you, and I believe I even asked it at the retreat. I said, "What's the worst that can happen when you put a big ask out there?" Right.
I'll answer that, but before we move on from the last one, I don't know why I didn't say it, but I think that the most important thing is to discover your why, because once you have a powerful enough why, then you're going to overcome all the barriers that come in your way for sharing. So if you like focus on, you know, finding your why, then I think that, you know, that helps a lot with, you know, getting started and pushing through when stuff's in your way.
Right, that's the essential motivation and focus, right, for everything, not just because you're following a trend. But yeah, but so, so going back to the question, right, do you, right, do you remember, I don't know if I, I think I'm pretty sure I said this, right, like what's the worst that can happen if you, if, if you ask it? What was the typical answer?
I mean, nothing. If you're not asking, you're going to get a no. It's a guaranteed no. Right.
But people think that's the worst that can happen is that they're going to get a no. But the actual worst that can happen by asking, a big ask?
Oh yeah. By asking, the worst that can happen is you get a no. The best is you get a yes. If you don't ask, the best is a no.
Right, exactly right. And I kind of say it like the worst that can happen is they actually say yes, because then you have to scale up your skill level or your energy or your effort to now match the request, which means you're now— you personally have to play at a different level.
Yeah, and that's actually helped me a lot on my podcast journey because I think my fourth guest on the podcast was a YouTuber with over a million subscribers. And this is before the podcast was live, before it was a thing. I was— I had to get a couple of cans and the in the pipeline. So I'm this introverted person who's nervous about talking, doing audio-only podcasts, 'cause I don't wanna put my face out there and talking to, not just like a public speaker or someone that's just doing small things, this guy's posting videos every day, he's a YouTuber. And so I'm just surrounding myself by those people, but also willing to ask to get them on as well.
Yeah, right. So you have to be a little bit ballsy, or as they say in Yiddish, chutzpadek. You have to have a little chutzpah to have the audacity to ask I remember doing that, I remember 3 or 4 months ago, I was going around, I'm like, someone said, "Go on Amazon and look up books to be released that haven't been released yet, and see what books stand out to you that would be right in," and I really wish I remember where I heard that idea from. So I did, and I stumbled upon a bunch of really cool books, and I'm like, "Wow, this will be really cool, and it's coming out in 3 months from now, 4 months from now," and I started going through them, and I started reaching out to the different authors, of those books and saying, hey, would you like to be on my podcast? I know your book hasn't been released yet, but I saw it on Amazon. And like, I started getting yes after yes after yes, because who doesn't want, you know, some good free publicity, right? And then all of a sudden, um, there was something on leadership, and then it led me to Howard Behar's book. And Howard Behar is the, um, former international president of Starbucks. And here, this book was already out, um, It's Not About the Coffee, which I highly recommend to everybody. It's an easy read. It's basically based on the, um, I think what they call it, their— not their apron, but their— I can't remember the exact title, but it was the principles they gave to each worker, but then he expanded on it. I found his website. I dropped him an email, and within 15 minutes, he got back to me, which was absurd. This is probably, of the people that I potentially could or have interviewed, probably the most successful person out there as far as when it comes to— not necessarily as far as his personal financials, but as far as brand reputation. And in 15 minutes, he got back with a yes. So, you know, again, that whole thing of like the worst that could happen is that they're going to say yes. And I'm like, holy crap, now I got to really be prepared. You know, I have to really read the book. I have to really watch this. And, and I got so much out of that process. I learned so much about servant leadership. And I know he's very connected with the whole John Mackey, um, and Rand Stigand, that whole thing of conscious capitalism, which Starbucks is connected to, which I'm a big fan of. In the first place. Having met Rand Stegen at my Business Finishing School conference, he's one of the guys who helped facilitate the merger between Whole Foods and Amazon. So really cool, really cool stuff. So let's get more, a little bit more into your podcast because, um, right, that we met at Podcast Movement, which was my first conference ever because I just started my podcast this past summer of 2019. I think I released episode 2 or 3 when you and I met. I had no clue what I was doing, even though I'm used to having conversations with people, but I felt like such a fake and a phony showing up there. I don't really have a podcast yet. I don't really have followers. Maybe they're like— I think I had like 40 or 50 or 60 people listening to my show at the time. How many of those were people that already knew me? They weren't like— which is cool that they would give me their time, and I'm really honored by that, but it wasn't like thousands and thousands and thousands like all these people up on the stages were talking about. What's the origin of why influence and why is that so important to you?
Uh, so for me, you know, I didn't even know it mattered to share and then I figured it out and then I had to take a long journey to start sharing. And basically, you know, it's based around the fact that I've got all this entrepreneur experience and I've been able to help so many people, especially one-on-one. I've been having these conversations So I saw I've got all this hidden wisdom and knowledge inside me that nobody else has access to unless they talk to me one-on-one. And the idea of the podcast is to help inspire other people to share their hidden knowledge and wisdom because I felt like if I was going to do something that could make a positive impact on the world, inspiring other people like me to start sharing their hidden knowledge is going to raise the collective consciousness level of the human race and essentially like help us evolve faster, essentially. So I can like help move the needle a little bit if I can inspire you to, you know, start sharing that hidden knowledge that you have that nobody else has.
So do you— did you always have that innate belief that everybody has something inside of them that if poked and prodded and pushed a little bit you will unpackage that? Was that always there for you or is that something that you kind of learned along your—
The whole unpackaging part, I didn't think about before, but I did always believe that anybody you meet is going to have something that they have that's over you and some kind of knowledge or wisdom aspect. And I've always respected people in that regard, but I never really considered or thought about helping people extract that or pour that out or say, okay, you should be sharing that. You need to be sending your message out there in a bigger way. I had an awesome guest, his name is Devon Brown and he is the world's best event MC. If you've been to any of Russell Brunson's events or— Yeah, he does Funnel Hacking Live, he's in all of them. He does Tony Robbins, Dean Graziosi events. He just recently did a a live event where he emceed with over 200,000 live people. And so no big deal, no big deal, no big deal, right? So he shared on my podcast, he was saying that if you find a message inside you that can touch people's lives and makes a difference, then you're doing the world a disservice by not sharing it. So stop ripping the world off and start sharing.
That's so interesting that you're saying that. So my coach Rick Sappio from Business Finishing School, um, on his TED Talk, um, that he gave in Italy. He grew up in New Jersey, and he lives in Dallas, but his background is Italian. He gave a TED Talk called Purpose 2.0, and he said the exact same thing, right? His big thing was about catalyzing statements, right? Like every brand has Domino's, 30 minutes or less, or Volvo, we build the world's safest cars. That's the rally cry that brings people to that brand or to that experience. He also is incredibly— his mission is to inspire entrepreneurship and entrepreneurship. Others. And as you know, we did some of the curriculum on our weekend together from Business Finishing School. And he says the exact same thing, like, "You are ripping off the world if you don't find your purpose." And what he really means by that and what he's shared in multiple places is that it's not going to come and smack you in the face. It's not going to all of a sudden come up as an epiphany for most people. It's not going to be something that you may pray on, right, it's going to come in a vision. He says you actually have to go out and you have to choose your purpose, right? So from all the princes in all the lands and all the princesses in all the lands, you got to choose one. So you get to decide what your purpose is, which again goes back to the why, right? What is your why? But on the deeper level, how do you, on a spiritual sense, in a psychological sense, how do you, what do you want your legacy to be in the world? How do you want to have that, right? That, that not influence on like being an influencer, right? How many numbers you're getting, but how do you want to touch people's lives?
Yeah. Yeah. I agree. Are you asking me that or?
Yeah. Right. No, but I'm just, as far as like that mindset, right? That's, that's probably what, that's what you're trying to extract from each of your, each of your guests.
Yeah. And that can evolve over time. I mean, when I ask my guests their why, uh, sometimes it stays the same because I'll ask why they start and really deep dive into like Why did you start sharing and what did that look like? And then move on to like, okay, well, why are you still doing it? And sometimes it stays the same and sometimes it changes. I've had an Instagrammer, she's got about 200,000 followers on Instagram. She's a fashion model and you would think, okay, fashion model, you don't know what's behind the scenes of that. But both her parents are diplomats. She's from another country and she wants to start a YouTube channel. And on a whole completely different aspect of things, just to make a world, a positive impact on the world. And she's a very smart person. So now she's got this Instagram audience for fashion and she wants to make this YouTube channel, migrate some of that audience, but it's very different. And that why is evolving. She's finding that she's less passionate about the fashion than she is about this new topic.
And that's a really good perspective for someone to have is when they're done and they fulfilled their mission in that vertical. I find that a lot of people struggle with that. A lot of my clients, they've been, let's say, in the education world, and they're making their $40,000, $50,000, maybe if they're lucky, they're making $60,000 a year in some positions, and they're just over it, and they're ready to do something new, but they're used to being an identity for so long. They know also that— with one of my clients, I'm like, "You know you can tutor." We did the numbers on if they charge what the going rate is, how many hours a week they would need to tutor over the course of a year in order to match their salary. The numbers were astonishing because they never put it into that context of, "Wait, so I only need to work an extra 15 hours a week to match my salary? And what happens if I just want to tutor and not and just do that. And this pivot of how to think more creatively, even if you love what you're doing, but you don't want to be in that same stuck place anymore. And now we're seeing this, especially with the pandemic, of like what people are doing at home. There's someone in, I'm in Jesse Itzler's Build Your Life Resume program, Pablo, right? And someone just said like, I'm out of a job, I don't know what to do. And I went on their Facebook page to see their background and see if like, sometimes they say like worked at here. And I saw that he had a dojo and I'm like, I'm like, "Dude, why aren't you just offering free, right now, free lessons? Do that for a month, and then 2 weeks into it, say, starting whatever, April 15th or May, I'm gonna start charging, but give a lot of value, and then go to online, you know, 'cause we're not going anywhere for 90 days at this point, at least, and build a reputation that way, or build YouTube videos and break it down and just become an expert on that." And he's like, "Yep, I'm already on it." Right? And so the pivot is so important for people in their, in their platforms.
That's really important.
Yeah. Yeah. So I want to kind of wrap up with this one last topic, which I think is super cool because I got to spend the whole weekend with you and your wife, Crystal, is that both of you are entrepreneurs. And I haven't really talked about this topic on my podcast yet where I've had, you know, people in relationships where either the husband or the wife are the entrepreneurs and the other person might be doing— they might be working for someone, but they don't necessarily consider themselves an entrepreneur. What has been your personal experience in the pros and cons of having an entrepreneurial marriage?
Well, one of the big cons that comes to mind is healthcare. You do not have very good healthcare options as an entrepreneur. And since you don't have a significant other giving you their plan, you just sort of got to deal with what you can get access to. But on the plus side, it's like, you know, we're both flexible lifestyles. We work from home most of the time. So that allows us to be able to travel more. Or, you know, Crystal does a lot of speaking. So sometimes I can go travel with her when she goes to speaking events, or if I'm traveling for business, she can travel with me, or we can take time off and disconnect. We can do things during the day when normally people are working. And then you have a flexible style so you can avoid busy times. Some of the downsides are it's hard to shut off sometimes. So as an entrepreneur, there's unlimited amount of work you can do. And just inherently, if you're an entrepreneur, you know that it's hard to shut off. It's not like a job where you can just turn your phone off at the end of the day and just call it. So when you have two people like that, sometimes it gets in the conversations a lot. And then I've up to this point been wary of getting the business together because I feel like if it's already hard to shut off as an entrepreneur, if you're both married and you're business partners and working together on things, it's like at the dinner table you're going to be like, "Oh, well this client had this issue today." And you're going to be constantly immersed in that world and it's not going to— I'm worried that it wouldn't stop. So I've been wary at like how I'm helping and she's the same. Like we help each other from like a strategy standpoint and we're very helpful with that. But as far as like execution-wise, we try to keep things separate at this point, at least.
Yeah.
I mean, overall I like it.
Yeah. What was really cool after the weekend that we were all together, you guys just like had your car ready and you guys ended up camping for a couple of days after that, right?
Yeah. So the mastermind that we did with you guys, like you were already in North Carolina. So why not go a little bit, hang out there for a little bit? So we brought our tent with us and even though they're weekdays, we both have flexible schedules, we can do whatever we want when we want. So we decided to go camping and it was perfect timing because the world was ending at the time or started to end and we're out there camping in tents in nature. It was pretty nice.
Yeah. So from the retreat, from the How I Show Up retreat, was there any takeaways or insights or experiences that you feel like just stands out to you that you would like to share?
I think it's definitely valuable to think about where you want to be. The idea here was where you're going to be in 10 years and then try to be that person. So you have to put a lot of thought ahead of time as far as, okay, well, this is where we are at now. Think big for 10 years. Okay, well, now think bigger than that because 'cause you wanna have something that's sort of like a stretch goal to aim for. So the preparation was useful and then going there and being surrounded by people that are all thinking strategically and trying to help each other overcome maybe like mental barriers. Like, well, there's multiple times during the weekend that people are like, "You're not thinking big enough. This is what you're thinking, but you can accomplish that in 2 or 3 years. You're not thinking 10 years out." And so I think that overall there's a lot of value to immerse yourself with a group of high caliber people that can think strategically strategically and help push you much further.
Yeah. What are you like— speaking of like high caliber, I mean, like everybody was there and like, this is mad shout out to like Pablo, right? Our good friend who curated this group of people for this weekend. And it was like just a great vibe of people who are really bringing a lot to the world. And what I loved even more is that we were not only able to just bring our business side to it, but we were able to bring our personal emotional side to it as well, which, right, we were talking about a little bit ago about vulnerability and being able to show up on a different level. And I think that's like the mission that Pablo and I really want to create, right? That if you can't get to that deeper level, on the psychological side for me, and from the business and marketing side for him, that you're not going to really ever, you know, grow and evolve both as a business and as a person. And I think that was so beautiful for me to see, one, like just the connection that everybody was able to get over the weekend. And we're still great. We have our WhatsApp group now. We're now creating our— Pablo and I are putting together the Facebook group, and we're going to have a mastermind through it and all these other cool things that are going to happen in future retreats once everything settles down. So, for people out there who definitely want more information about that, please hit me up on Instagram and send me a DM if you'd be interested in a future mastermind retreat up in the mountains of Asheville, North Carolina. But, for me, I think one of the most powerful, seeing you guys as a couple and seeing some layers coming off you guys over the course of the weekend while enjoying the I like the connection that you guys have because you're really cute, both of you. And it was really sweet to see an entrepreneurial couple together. So I really wanted to thank you for being part of that. And I was so excited when Pablo told me you guys were coming. So I was super excited about that. So yeah, so I just want to give like a final plug. So I know we mentioned— so they can follow you where? Like, what are all the different places they can track you down?
Everything's @yinfluence. So Instagram, Facebook, Twitter, everything's @yinfluence. Podcast is my main thing, but it's also on YouTube. I do livestream podcast interviews now, so they're video and livestreamed. So I'd say YouTube if you care to watch it or have it on video or the podcast if you want it on audio only, but it's just Y-Influence Podcast by Jeremy Siegel. And it's whyinfluence.com, whyinfluence@gmail.com if you want to email me. Everything at Why Influence. W-H-Y, I need to clarify that. W-H-Y Influence.
W-H-Y, right. Super, super, super simple, super streamlined. So guys, if you're listening to this and you got any value out of this episode, which I'm assuming you will, especially those introverts out there, right? You guys already heard my story. I'm sure you've heard me talk about how I My public speaking, I would rather get an F than stand in front of people back in the day, and doing this now at 41 is mind-blowing for me, reflecting back on where I was in elementary school and having to do a presentation in class and literally taking the F instead of getting up in front of 20, 30 people. But if there was any value out there, please leave us a 5-star written review on iTunes. That helps us get in front of other people. The more reviews we get, the more it will not only move us up in the rankings, but the charts, but it also starts showing up in other feeds for other— in front of other podcasts. But also, please do the same. Please go check out Jeremy's podcast, Why Influence, and do the same for him. There is so much incredible value there. It's not, you know, there's so many podcasts out there. I think there's 10,000 new podcasts coming out a month or something like that, I heard. But it's crazy, some crazy number. But guys, please, please, please do me a favor. Jeremy's a buddy of mine, so do me a favor and check out his stuff. And again, Jeremy, thank you so much for—
Thanks. Yeah, and I'm very reachable, so if you if you wanna just PM me, just feel free to reach out. If you're struggling to overcome a barrier, just PM me. I'd be happy to suggest an episode to listen to or anything like that, or just talk to you one-on-one if that's helpful. I'm very open, so feel free. And thanks, Jason, for having me here. This has been great.
My pleasure, and we'll see you soon. All right.
Thanks for listening to the You Winning Life podcast. If you are ready to minimize your personal risk personal and professional struggles and maximize your potential, we would love it if you subscribed so you don't miss an episode. You can follow us on Instagram and Facebook at Jason Wasser LMFT 🎗️.
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