Hello there and welcome to Successfully Depressed, and I'm your host, Kerry Finsand. This show is all about helping solopreneurs navigate mental and physical health in life and business. Today's guest is Jason Komosa, who spent over 15 years helping brands like Vitamin Water and Groupon. With their sales go to market and growth strategies. But by age 30, he experienced severe burnout, which led him to seek a mental health coach.
This experienced deepen his knowledge on all things psychology, philosophy, and Neurology. Ultimately becoming a mental health coach himself. His mission is to help leaders in the start Venture Capital world diffuse the stress, tension, anxiety that plagues the body in mind to stop arguing with reality and to literally create a life of thriving and not just surviving. Welcome to the show, Jason Komosa.
All right. That was beautiful. Well done.
That's a mouthful there.
That was beautiful. Thank you for having me. I appreciate her.
Yeah. You know, I, you introduced me to, well, I guess a quick background thing here is we both worked at Groupon many years ago together, and I think we only met each other maybe once. Um, in person. Yeah, a couple times maybe. . Yeah, we had a lot of connections, um, like Dan Gruber and Matt Rule, Nick and other people, um, who have had Matt in a show before. Cool. Which is cool. Which is great.
but this last year for me, I just, cuz kind of looking more into increasing my own kind of neurology and psychology and all the different things you talked about. So you mentioned this heroic program that you did about, you know, three, I don't know, three, four years ago when you did. Yeah, more
like, yeah. How long ago was it? It was probably like, yeah, more like probably 3, 3, 4 years ago. Yeah. It's been . I'm just thinking about now it's time flies, but yeah, you're right about four years probably.
So you told me about this program and then I ended up, started doing it. Um, the program Heroic, uh, which is formally called Optimized, I believe. Correct. I started it in about August and I'm still doing it. I will say the, the last month, I haven't been, uh, as on top of it, but I, you know, I'm doing that at my own pace cut now. It's a very intensive program. It's, it's great. I highly recommend to anyone who just wants to, you don't have to even go through the coaching program.
There's apps and other things that you can learn so I just kind of wanna get there. We'll circle back to heroic later, but what I really want to get started with is this kind of your career and which led you to be this startup, stoic. Yeah.
Yeah. It's a awesome question, and thank you so much for, uh, setting it up. This is a, this is a lovely thing I, I like to talk about. Um, so let's dig in. So, you know, I was a 23 year old kid, fresh outta college. Um, you know, I didn't really know what I wanted to do with my life. And so I grew up, uh, with a single mother without much money, pretty poor.
And so the story I had told myself, Literally for decades is that, well, once I get enough financial stability to take care of myself and my, my mother and my younger brother, then everything will be happy. Everything will be great. All my problems will go away.
And uh, uh, I was in between trying to decide going to grad school or joining the small startup, and I ended up taking a huge leap of faith and, and dropping out of grad school and instead, uh, working at this tiny little startup that ended up becoming Groupon.
And so through this transition from, let's say age 24, when I started to age 30, I had, I had found myself in a situation where I was, uh, rapidly, uh, increasing, uh, my personal revenues, um, you know, moving up the ladder in the company. And I was fortunate enough to have some financial stability. And yet here I was unhappy. And I'm like, wait a minute. I thought if I had a hundred thousand dollars a year, I would be happy.
, I thought if I had 150, 200,000, whatever it is, and then I got it and it was like, okay, well I'm still really empty and what's going on here? Because for so long, again, the story that had I had told myself literally became my reality wasn't true. And that's kind of what really kickstarted me into this mental coaching, uh, psychology world. Um, hope that answers your question.
Yeah, no, I mean, definitely. I think the, the one thing I want to point out with that too is that I, this might be true to you, it's definitely true for me, is that one thing I noticed, um, in when I had my own startup company, um, called Taplister, I became like the identity of my company. And then when I sold the company I was like, what's my identity and who am I?
So I think that's one of the challenges we have and I think that's probably what you kind of experienced kind of with your role, um, you know, helping develop Groupon. , um, you know, into, into like a national sales role and helping help other people is that that's kind of like, oh, this is, this thing was a rocket ship that took off. And it was a great experience to be there. This is kind of like who I am, but like all I'm doing is working. I'm making good money, but like, am I really happy?
I feel like that's kinda
what happened. It's almost like the, the story that I told myself was, this is the path, this is the path of happiness and this is where I, this is what I want to take. And so you mentioned, you know, I, I was burnt out. I was, uh, ignoring like the, my, my needs. So not just, um, I'm talking like exercise, eating a healthier and relationships, like ignoring the things that really mattered. To kind of put that aside and say, well, I can do that later, that can wait.
I gotta go work on some deals, you know, to run next month. I want to close some more deals so I can make more money. So it became this kind of like cycle of. , it was almost like a drug, like it was addictive. Like, Hey, I, I gotta work more. I gotta close more deals. Um, and I found myself again. I was, I was, uh, um, I wasn't happy. I like genuinely was like, this is great. I'm grateful, but I'm not intrinsically happy.
And that's what really kind of led me down this path of working with, uh, Michael Bald, who was my first coach, and he's now the head coach and president of, uh, heroic.
Yeah. That, that's great. I know you met him in, in Chicago area, I believe, at a networking event. Um, yes. Tell me a little bit about that. How, how'd that kind of came to be. You kind of, you kind of knew that you needed to figure something out, so you said, okay, let's start networking. Let's see what's out there. It was
just, it was very organic. So like I was, um, in the mindset of like, I, first of all, I, I've seen a therapist and to me, and I don't know about others, the listeners, I don't know about you personally, but I felt like. Therapy was fine. Like it wasn't bad. It just wasn't impactful. I wasn't like, this isn't helping me change my life. And that's what I really wanted. I wanted to be transformed.
I wanted to rid myself of this, uh, of these stories that I was telling myself that really didn't serve my highest purpose. And I think all of us at, at some, you know, point in our lives or even right now where we tell ourselves stories and we tell ourselves the stories enough, they literally become our reality.
Yeah, that's, that's definitely true. And I've definitely been seeing a counselor for, you know, I don't know, 20 years, something like that. And, the coaching thing is something I've been considering the last couple years, and that's kind of one thing. I looked at this program where, you know, with the Heroic Train program, you are your first client is how, how Bingo. So that's, you know, if you can't do well in yourself, it's, you know, harder to truly help out people. I mean, we all.
we all are good at, probably a lot of us are good at helping other people out, but when it comes to us practicing things, it can be a lot more difficult. So if we can get that down, then it's easier to actually thrive with the people we're helping. Um, a hundred percent. A hundred percent. So with , the Heroic program, I think it, I don't know, I think it started like around 2014 or 17 or something. Was it,
so op the, the company Heroic, it actually was optimized. The, uh, optimized, uh, was acquired by Heroic, but the long story short is that this guy, Brian Johnson, um, he essentially as a self-taught philosopher, psychologist, and he's been building this action-based program. uh, for the past 20 years. And I think when you talk about like therapy versus what I'm doing with coaching and what Heroic does with coaching, it's action based.
So like you're, it's, you can do all the reading and studying and listening and podcasts and whatever else you want, but if you're not actually taking the wisdom that you're ingesting and putting it into action, it doesn't matter, right? What's the point? Why just hold in all this beautiful knowledge and not do anything with it.
Yeah, and I think interesting thing about the program, some things I like is kinda like the, the plus fun where you make these, these micro improvements over time. And, and I've read, you know, I love the broken comic habits and then there's Tiny Habits by PJ Fogg and they all kind of say the same thing to a certain extent, but just these little micro things. And one thing, I've actually personally started doing this this month. I know Brian.
He likes to break up his pushups throughout the day, or I guess his burpees, I guess is what he does. Burpees. Yeah. I'm kind of a messed up shoulder and I, and I like to do upper body stuff, but for me, doing a lot of pushups in row just isn't right. So I, I've been breaking it into, you know, doing a hundred pushups a day and, you know, five sets, seven sets depend on the day. And, and I, for me it's just nice cuz it's like, okay, this is, my body can handle it better, it gets me moving more.
I, I know they have the whole kind of a thousand second, uh, philosophy where he says every you, every thousand seconds get up and kind of move around cuz we're so lethargic. So I think there's just a lot of just basic stuff that we all kind of know what to do, but we need kind of a framework to put it into mind and like into our mind. And then what are these steps to actually, you know, take action versus, like you said, just
reading things. Yeah, it's, uh, I would, the analogy I like to use is it's like a personal trainer for your mind and your body and spirit. it's not personal training to go get fit and get a six pack. It's to make sure that your, your brain and your heart are in the right place. And it's, it's about upgrading that mental software. Right? A lot of us are running on AOL from 1995, and they're not a CD rom with Dialup. Right? It's like, Hey, you gotta, you gotta upgrade. And we haven't done that.
A lot of us are living, uh, you know, we're, we're still, uh, uh, these inner child, our inner child is still here even though we're 40, 50, whatever years old.
Yeah. , It's a challenge. And this how society has changed, especially let's just say in the last 10 years with technology and in our attention spans going down because, you know, now things like Instagram and YouTube, like shorts and TikTok, it's just like quick information, everything. Yep. Yeah. And there's, um, I want to say it's, I read this really interesting book, uh, I wanna say it was called IR Irresistible, maybe that was about, uh, technology.
and uh, just how it's all designed, like, you know, Facebook, all these different things are really designed, uh, to, to game, to game your mind, to, to have a sort of attention span and to game your Yeah. You know, scroll, death June, scrolling through things and stuff.
So it's kind of, it's kind of scary and, and so with, it's harder for nowadays I think for people in general with the society and probably especially in America, just to fast paced that we have and to actually kind of get in tune with ourselves. What are some things that with your clients that, uh, you work with to kind of help people get in
tune? Well, first thing I, what I love, and I know we talked about like what are some, take some tools or takeaways. One thing that I absolutely love is the idea of block scheduling. And for those of us who are listening who went to high school, which is probably most, if not all people, You'll know that when you go to high school, you have these different, you know, you have your different classes throughout the day.
00 AM and your chemistry class, you're in
00 AM right? And that's where you are. And you're not at in gym class and you're not taking a lunch or a break. Like that's where you are. And that's where you belong until chemistry is up and you go to the next class. And so we need to implement these types of tactics as adults. We have the power to control what are we doing with our time, especially in the mornings and the evenings. So why don't we set up our, our day up, our week up for success and use block scheduling?
And that way we're not using this beautiful, precious, finite energy to figure out, well, what am I gonna do now? It's 1245 on Friday. Like, what am I gonna do now? Like my schedule is lined up for me so I know it's autopilot. This is where I'm going, this is what I'm doing. I'm having a podcast with Kerry, and then after that, boom, here's the next thing, and then I go get my daughter from school.
And so it's, it's, uh, it's an autopilot schedule where I don't have to think very much like how Mark Zuckerberg right. Wears the same clothes every day. Same. He has 25 t-shirts. He doesn't have to think about it. It's one less decision to make. And that's the same exact application here in the real world. If you can set up your day on autopilot, you don't have to think about what you're doing because it's already done for you.
Yeah. You know, you only have so much decision making capability in a day and you're just kind of chipping away at it. If you're keeping thinking like, okay, what am I gonna do? What, what am I gonna do now? I definitely have that issue myself dealing with, with adhd and, and it's, it makes it a fun challenge. What works for you? Sometimes is the blocking thing for sure. Like, you know, hero, you got your am pm bookends, what you're talking about, like kind of. Design your day.
But there's a timer app that I use that actually just nice goes through and That's beautiful, man. Yeah. And it's like, I'm like, oh, okay. I need, am I focusing cool? I'm focusing this summer's time I have versus just like, oh, what's, uh, Hey, look at the time. Yeah. Here, or look at this rabbit
hole. Let me go check these. Yeah. Let me check these blogs, or let me check the sports scores. And then all of a sudden it's an hour later and you're like, oh man. Like, then you don't feel good. So it's, it's a lose lose situation.
So I guess another question I would have for you is, um, with when you're working with your clients are you following the, the coaching framework of heroic and then also kind of adding your own flavor into it? Or, or kind of what's your.
That I don't think there's one right way to coach. I think depending upon the person, the personality, and the other person as well, the client. So who am I coaching, right? If I'm coaching, um, a woman I, I helped, uh, an older woman, um, you know, that conversation may be tailored differently than someone who is, uh, a 25 year old fresh outta college guy, right?
So the style, the conversation, the communication that may change, but the core values, the core mission of what we're doing, uh, that doesn't change. And that, you know, at its core, it's about, again, literally building and creating a life that you want and not just like taking what
comes your way. Yeah. I mean, obviously it's gonna be different for every person, but there's still a framework that you're, you're following to kind of move along with the needle forward. What if I, let's say I was seeking out a coach. Yeah. , what would be steps for me to find a coach to help me with some, like a service like yours or something similar to it?
In my experience, there's only two problems in the world, like people in general have, there's only two problems. One problem is you don't know what you want. The second problem is you know what you want. You just don't know how to get it. In my experience, the only two problems, so if you're asking yourself these questions and you know, and again, you're looking for, for help, it starts with self, right? What do I want? What do I want out of this?
Like, start with the end in mind and then work backwards. Reverse engineer, how are we gonna get to where we want to go? That's kind of my, that would be the game plan. That's like my structure of figuring out, okay, this is our north star. This is where we want to go. Here's where we, here's where we are now, right? Here's where we want to go. How do we close that gap? How do we, what do we do to make sure that we're moving towards where we want to go?
Um, and where we want to go is, is subjective, independent upon each individual person, um, whether it's a client or a friend or anyone, right? Like it's conversationally. It's what, where do you wanna go? What do you wanna do in your life? Because when you're 95 and you look back and say, wow, I really, you know, did a lot of awesome things as opposed to, wow, I really regret ab not doing A, B, C, and D. You know, that's, that's kind of, again, starting with the end in mind.
Is your coaching, is this something that people work with you on for a year, for several months? Or I guess, how does it work? Because I mean, let, let's just kind of break it down, like coaching for dummies. Like, like what's the most, like, basic level of kind of what the, the nuts and bolts is? If someone was to, to do coaching with you or just in general? . Jason Komosa: Yeah. I mean, so, so a basic, um, you know, there, there's lots of different ways to be coached.
You can do one-on-one coaching, which is my, typically what I do. You can do small groups, which I've done before. You can do larger groups. Um, and then you can do kind of like the, IM personalized, just general, self-knowledge, uh, self-improvement, you know, books, podcasts, and so on that aren't tailored to really anyone, specifically just general information. Typically it's, it's about a min at minimum. It's a six month program to work with me.
And really, again, it's not about like, it's not about reading certain books like we're changing your life. And the reason that we are, um, the reason that I'm doing this, the reason that I enjoy doing what I'm doing is because of the significant and life-changing, um, attributes that I received from my coaching, right? So I'm giving back, I feel like, um, this is my calling. . Um, I studied psychology, uh, an undergrad I was gonna go get my doctorate in psychology at the University of Chicago.
So psychology's always been in my blood and I, and I'm mixing it with sales, right? When you're, when you're in the sales business world, if you don't understand psychology, you're not going to thrive. So again, kind of blending the two worlds of business and, and psychology, um, yeah, meshing them together and, and helping folks. I love it. Let's get a little bit into the, the psychology of sales.
And I know that's something that is kinda one of the things you kind of helped with people too, and you had success at Groupon and some other places . Yeah. I know you, you've also helped out some different startups. You were an investor and also helped out a company called Doorman for a while and, and Facilit. Yep. Um, yeah, so from all that experience that you have from that, what are. What are some great self-care tips for people that are in sales?
Because it is that roller coaster, highs and lows, and you're high, you're high. When you're low, you low. It's just, and you're only as good as your last sale. So what are some things that you did for yourself during those times when it was really difficult or like, oh, next sale. Next sale. And,
well, the, the very first rule of thumb that I would ask of all folks, especially sales, uh, is to have the two buckets. You have two buckets here in your hand. One of the buckets is things you can't control. The other bucket is things you cannot control. And so I'd ask you to take the bucket that you cannot control and put it out of your, your vision, because so many people, especially in the sales world, are focusing on lots of stuff they can't control, like signed contracts.
You cannot control how many contracts you get signed. That's just a fact. You can control the efforts, you can control the messaging, the strategy. The number of hours you work or the quality of work, the quality work that you put in, you cannot control how many contracts are signed. So the more that you kind of get to the root of, um, this idea of stoicism, right? Hey, I'm gonna focus on the things that I know I have a, a direct control over. That's what you wanna work with.
That's stay in your world, stay in your lane, and ignore the rest. Um, that's one of the things that really helped me. Uh, you know, in my sales career, I'm gonna focus on what I can control, and I'm, and if I'm above goal, I'm gonna work the same amount. And if I'm below goal, I'm still gonna work the same amount. And some managers might not like that, but too bad. It's like, this is how much I'm gonna work. I'm always gonna give it my best.
Some days I'm gonna be better than other days, but I'm gonna know that, look, there's another day ahead of me and I'm gonna just do my best.
Yeah. I know in my, my really early sales career, I used to work for a company called, uh, city Search, which was, uh, yeah, kind of Yelp before, uh, Yelp. Yeah, I remember the Citysearch. It was a, you know, cool place to work, you know, just, it was a online review website and we sold advertising. And that's kind of got my bug in the star world and selling online.
Uh, yeah, but I, I know one time sometimes that's that unrealistic goals and I, and I would hit them, but it was, I would just not be healthy. I just, I would, I was got, it got so bad. Anytime I was out with my wife, I would keep business cards in my wallet and then backup one first. I'm always, I'm always, always be closing. I was just like, oh, I gotta sell. I gotta sell. And then you're always on. You're always on.
Yeah. Yeah. And so yet to have that balance, and, and if you're always that way, then you kind of burn out. I know that I, I like won a award for, you know, kicking butt in the region and stuff, but then like, I was good for a while. Then I was like, a few months later I kind of felt kind of burned out and I was like, wow, I really overdid it and stuff. So it's like, that's that thing you have to learn, that consist consistency over time, like you said, and
Energy management. You have to manage your energy. And Kerry, think about this. LeBron James, arguably one of the best NBA basketball players of all time, right? What is he think about this. Like what would happen if LeBron James just played basketball all day, like he wouldn't be that good at basketball. Why? Because the things that he does off of the court, relax, sleep, meditate, yoga, eat healthy, have fun, hang out with his kids and wife.
Like all these things that he's doing off of the court contribute to his success while on the court. And I think especially in the business world, we sometimes just ignore that. Well, I, I can push aside my exercise or I can push aside my, uh, playtime, if you will, to do another hours worth of work. We just ignore these needs and wants that we have to continue to just plow through.
And really what we're doing is we're, we're shooting ourselves in the foot because the work that we're doing is not quality, right? It's not a quality, uh, uh, block of work. We're just working to work. Our brain is dead. We need to, we need to , get off the computer and go, uh, rejuvenate ourselves. Recharge.
Most of my career, I've worked from home. My early prior career we worked from home. You're like, how is this work and everything, and, but. Then you have to figure out the systems and, um, liking heroic. I know they, you know, they shut down complete when you're done with the day. Like, okay, you're done with work and then, you know, move on to, to more, you know, self care, what's next. Yeah, exactly. And, and my wife's always been great at that.
She, she's in finance and when she's done, she's done. And, and so when she works, she's just on point. But when she's done, she's like, and she leaves the worry at work, even though she works at home. So like, I really, yeah. Think it's amazing when people can really have that energy to do that consistently. Well, think
of, think about this, if, if I was a neurosurgeon that was saving people's lives, like, and I'm like, that's okay. You want to, you want to come call me at any hour? Like, that's understandable. Most people are not saving people's lives as a neurosurgeon.
00 PM. To try to close this. Like, it doesn't make sense to me. We're not, we don't need to be online all the time, and yet we are right Slack and email and text message. Like all of a sudden, o over the past 20 years, we've now opened up our entire lives to work, work can now intrude us whenever we want, whenever they want. Whereas in 1990, you didn't have this, you didn't have cell phones, you didn't have email.
People went to work, and then they came home and like, most likely you couldn't do your work at home because the work was at the office. So again, it's, it's this, this kind of, um, bizarre world we live in. Where we are, we allow ourselves to be open, especially with notifications on like you're asking for it, turn the fucking notifications off , Kerry Finsand: you know, we're That's the thing. It's like it's advanced so much in a, in a short period of time. We're not designed with it, but it
keeps moshing forward and, um, . So that's where like one of my favorite things to do is to go for walks. Yes. And just get out and just my neighborhood or nature. And, um, it just, and I, and I take that approach where it's like I say, I, I, I put a really low number in my head. Let's go for a 10 minute walk. And then it typically turns into half an hour or more.
Yeah. And, and so that's like really helpful too, cuz then you're like, you're exceeding your goal, you're outside, then you're starting to enjoying it. Maybe you're listening to a podcast, maybe you're just listening to the birds outside. Um, yeah. And here's,
here's the crazy and here's the crazy part about that is that for a lot of people in the world of 2023, that is the challenge. The challenge is to go out and walk or, or take a break. The challenge is not to do work because you're so focused and driven on this progress of work that you're, you're making it, it's actually harder for you to go take that break. Or to go exercise than it is for you to actually, you know, do the work you're supposed to
do. Yeah, definitely. I mean, yeah, you're getting kind of the, the, the zone or you have, you have meetings back to back to back. That's why it's like you need to have a little bit of time between meetings to kind of reset your mind and everything. Take a break. Yeah. It's kind of this go go go thing.
And that's where I think it's nice about a lot of companies nowadays are having more flexible schedules with work from home or hybrid or you know, you have a core hour of the day, it might be five hours. Everyone needs to be on this kind of overlapping time. Mm-hmm. . But we all, like you talked about energy earlier, we're all different with energy. Like for me, I have more energy definitely. I'm a more early riser.
So like in theory I want to work out in the morning and then like do my more intensive mind work in the morning. And then the afternoon I try to do more creative work or more ab stuff that takes less brain power. Um, so realizing that cuz not everyone's the same. And so like, if you're working somewhere and it's just constant, go, go, go, go. And then the afternoon you're like, your time when you're like, okay, I'm not, I'm kind of at my, my bandwidth limit.
Yeah. And then you're like, something really in, uh, intense comes in. It just like, it gets overwhelming. It's like, does not compute
basically, you know, for some, and I think we have to give, uh, a huge shout out to like engineers and folks in the tech world because at least in my impression, it seems like the tech world, uh, the, the engineers and so on, they kind of paved the way for other folks because the engineers in the tech world oftentimes will work like late at night, you know, or they'll work till two in the morning, but they don't start work till 11:00 AM the next day. And that's okay. Right.
Like, like you said, companies should be able to empower their employees to let them work when they want to work and when they do their best work. Now of course, are there caveats? Sure. You gotta be online. Everyone's gotta be online a couple hours a day. Yeah. But let the people do their best work when they work best.
00 AM so
be it. Yeah. That's why I, I'm like, if I had the developer mindset, it, I would, kind of can create your own, create your own, you know, job to a certain extent. Nowadays it's, it's great. But yeah, I have a friend that he works late at night or he will work for a couple hours, uh, during the daytime, then just late at night. And that's just one of his, it works for him. He has, you know, yeah. He has a kid and everything.
And so like, it's just like his time to kind of get in the zone, but hey, to each their own. I mean, for me, I'm like, you're doing, you're typing at like, you're coding at three in the morning. Uh, no, I, I can't do that now. I'll be getting up in like three hours. So, . Jason Komosa: Yeah. Or less. Yeah, exactly. Um, the, the next thing I kind of want to want to bring up is, um, I'm kind of curious about when you were working for Vitamin Water Action.
Because that's another like, company that just took off. I know 50 cent got a lot of money out of it. I don't know how well he's doing now based off of everything . He, he, he did more of an equity play, which worked out well for him initially. He did. Um, he did. Yeah. So what was your role in that company and, and kind of how was that growth trajectory?
Yeah, so this is a really good story. Um, let me just pack up a step and let, I'll share this story and I hope this empowers at least one person to go out there and do this because it works. I was a sophomore in college and I was looking for a part-time job to support myself, uh, through throughout school. And so all my, this was like, uh, in the springtime, and so a lot of my friends were looking at, uh, applying to Target and Whole Foods. Um, nothing wrong with these places, right?
They're reputable businesses. I shopped there. It's great. So they're all applying to these jobs to get summer jobs slash uh, jobs during the summer or school year, I should say. And I'm thinking to myself, okay, well I'm 19. Um, I kind of wanna like do something cool and fun, so I'm gonna make a list of 25 companies and I'm just gonna reach out to them and, and express my desire to help them grow. So, Carrie, this is 2004. So there was no LinkedIn, Facebook was only for college kids.
Um, and what I did was I set a 12 week timeframe. This is all like, I just thought, like, I literally just thought of it. I didn't like do research. I'm like, I'm gonna give myself 12 weeks. I'm gonna cold call cold email, and I'm actually gonna write letters and mail them into these companies, expressing to them my desire to help them grow. And the worst case scenario here, Carrie, 12 weeks go by, I get all nos or I get all silence. So no response at all.
And then I go get a job at Target or Whole Foods like everyone else is doing. That's the worst case scenario here. . And so sure enough, I just heard the phones, 800 numbers, talking to random people. Again, I'm expecting nothing to happen. I'm expecting this to be a spectacular failure and I'm gonna go work at Target and I'll be fine.
And so I think week six or seven is when I got a call from someone and, uh, it was an unknown number, so I didn't pick up, listen to the voicemail and it's this woman who says, Hey, I'm, you know, Mary or whatever from Vitamin Water Corporate, I got your information, but I need to verify, uh, that it's okay for me to share your information with the head in Chicago. So I called her back and said, yeah, let's do it. And so she called me and I was like, stunned. Of course, I'm a I'm a kid.
I'm like, what? This worked. So I get, you know, have an interview and um, I got the job and I was there for a year, part-time. It was incredible. And they're like, you should drop out and like work full-time with us. And I'm like, whoa, hold on a second. , you want me to drop out of college? No. Like, that wasn't like, that was the farthest thing in my mind from like, that wasn't even a possibility. I was in school, I had grants and loans and all the, like, I was just like, no way.
And so, sure enough, you know, years later, uh, vitamin Water was purchased, uh, Coca-Cola bought Vitamin Water for $4 billion. So had I have dropped out, it would've probably been a good move financially. But I don't regret it because again, the lessons were there and I did, I, I learned from that instance, I learned from the Vitamin Water situation and that's what drove my decision to drop out of grad school to join
Groupon. Okay. That, that's a great story cuz what I like about it too is that you took a, a risk while in college, but it was a calculated risk. You know, you're like, oh, I just want to see if I can work at these different companies. And it's, it shows like a. You know, you're a go-getter. It shows that you're like this kind of entrepreneurial spirit. With startups, you never know if someone's gonna take off. You know?
It's, it's like, and that's like with, with Group one, it was like an amazing one too. So it's like you were involved with two, which is really hard. I mean, I've been trying to find the next group line to work out for years myself, cuz it was so much fun and so many great people there. That's a great story just to kind of come full circle and, um,
yeah. Well, in, in my mind I was, again thinking so after, after the Vitamin Water thing, cause I saw all my bosses, right when they got, when Coke bought us, like they were out buying Assin Martins and like, clearly they had enough money to easily retire. And then I was, I, I got laid off because I, at the time, again, I wasn't, it just Coke ingested everything with vitamin water and I got laid off. So then I'm thinking, okay, I'll go back to school. I'll get my doctorate, da da da da.
And then when this, uh, I, I came across this small company in Chicago, which is Groupon. I was like, I have to work there. And I did the same thing, just cold call. I actually harassed Andrew Mason, uh, on the phone. I was like, I gotta just gimme an interview, man. Like, let's just talk. And so that's kind of how things ended up,
uh, at Groupon. Well, that's, that's awesome. So you, you had the gift of Gab and, uh, you know, selling yourself into, into these roles, at these positions at, uh, well,
and and and it was passion. It was passion based. Like the, the reality is, Carrie, the, the offer I got a group on was dog shit, right? Like, yeah, it was a, it was not a great job offer. It was a sale, a standard sales role. I think it was 35 or $40,000 base salary, and a little tiny equity. And I was like, I'm gonna, this is like something I'm gonna be a part of. And so again, I didn't join for the money I joined because I wanted to make a difference. And I love the, the mission. Um,
yeah. Was it, uh, was it always at the old Montgomery Awards building? Even in the beginning?
So it was there at the old Montgomery Awards building that's, uh, 600 West Chicago. And then we grew so fast that we actually had to temporarily move into the, the, um, 3 0 3 East Wacker, which is the KPM G building, I think. And so I think it's, it's, it's, it's accounting. I think it's some big accounting firm. And I remember the, like the first week we were there, there was like 25, 26, 27 year old kids. This was a summertime and like, it was just like taken over by these group on kids.
It was, oh man, what a
wild ride. When I, when I started working there, I was about, I think I was about 30. And so there's always like younger people and, and I've always been kind of a younger kid at heart myself and. And, uh, but I was like, wow, these, these guys are really young. I remember going through the training and the trainer was like, oh, you already know all these different sales tactics. I'm like, yeah, I've been, you know, doing sales for a while. I'm not just outta college.
But it's like, it was cool because they listened to whatever. They listened to you there. Cuz like I, I created a, a job there as a community manager. I pitched this idea that we had, importantly had some, some negative, uh, talk going on. Um, Portland's kind of, especially at the time, was kinda like the biggest, you know, small town, uh, mentality. Everyone kind of knows everyone.
Everyone's, you know, is more liberal and people had this, um, the lamb week, our, our weekly kinda like time out Chicago or something. It mm-hmm. It said on the cover Calvin Hobbs and it said poop on Groupon. And people were just upset. Cuz you know, the early days of Groupon, everyone's trying to figure things out and then people might sell maybe. Could be over sell, sells, people selling.
Oh, I, let's sell them a million coupons and it's like 20 table, 20 seat like restaurant where they can't handle the capacity. And then later on we had the, the calculators that figure out capacity and stuff. So we figured all that kind of stuff out. So I had the kind of a role where I, I pitched this thing, I wrote a business plan, pitched it to, um, to Darren and, and to my boss, John Waller. And then within like six months I had this job and it was a dream job. And it was amazing.
And the only reason I left Groupon is because at the same time I was working on, on a startup myself, and I, I got accepted to a tech tech incubator, raised some money. So I was like, wow, this is crazy. Like, I kind of have like this group on dream job, but then like there's like, I have to try this thing. Yeah. And um, so I think, I think what I'm trying to say here is, you know, it's, it's nice to take risks.
Not everyone wants to take risks, but I, I've taken a lot of risks and I, I think we've all had a lot of success and a lot of failures and, um, . But if you don't try, then as you get older in life, you're like, why didn't I, because a lot of people like, oh, I had that idea, or, oh, I wish I would've done this or that And I'm like, yeah. I mean, there's, there's different ways to do it. And, and it is a rollercoaster, you know, working for startups or, you know, or having your own.
So I think there's some great stories behind it.
Yeah. Everyone wants to hit a home run or a grand slam, but nobody wants to step inside the batter's box. Right. And so you have to be willing to strike out. Uh, and the only way to hit a, a double or a single or triple or a home run is to be willing to strike out. Um,
yeah, we gotta get some sports re references here. We gotta, you know, . Yeah, exactly. And. LeBron's amazing, but I'm, I'm team Jordan,
so, oh, of course. I mean, Jordan's not playing. I could, I could've used Jordan. I didn't. He's not playing, but you get the idea. Yeah. It's, uh, um, and speak really quick. Speaking of baseball, another quick stat, which I love to throw around. Okay. The average hall of famer has a 300 batting average, right? So what that means is you are in the Hall of Fame. If you lose seven out of 10 pitches, you hit three of 10, you are a hall of famer.
That means you lose seven out of 10 times and you're still in the hall of fame. So you're losing more than twice what you're winning, and yet you still make it.
That's, that's wild. I, that's a great stat because you don't really think about that baseball, you're just like, okay, you're buying 300, but you're like, oh, yeah, actually, if that was, like, if you're, if you're shooting foul shots, that'd be terrible. In basketball. So everything is kind of different. You have to now everything in life is apples to apples. So, um, on, on a side note, I saw the stat actually today, uh, from 98 to 2000, no, no, what was it?
88 to 2002. Tony Gwen, um, hit 300, um, with two strikes on, on in the pitch count. That's unbelievable. He's just like, he's just one of the best like hitters of all time. So that's a random
random sports back from the day. All right. I, I like
it. I like it. Um, well that's, yeah, that's, that's a good fact. I know you worked in consulting or you worked as, um, to helped out venture capitalists as an advisor, um Yeah. Different startup companies. So maybe speak to a little bit of your experience doing that. I'm just kind of interesting cuz you know, this show is about kind of business and kind of wellness, so
Yeah. So when it comes to some of the advisor roles I've had. Uh, typically it's through an introduction or referral. And my goal again is to provide value to an entrepreneur who is running a business and doesn't really know or does not have their expertise living in the sales world, sales is hard, right? It's not something where you could just pick up a book and read. You have to learn through execution, through doing, through action. And so my experience, right?
I've been doing sales since Vitamin Water, 19, 20, almost 20 years. It's, it, there's an art to it and I, I explain it like I'm not a, uh, in the sales world, I think there are like sales scientists, those are the sales enablement folks and the numbers folks, that's not me. Sales operations, I'm an artist. I like to help with the language, tonality, uh, the feeling. How are you educating the market on your pain killing product or service?
And so, um, more often than not, again, these folks who will want to, uh, bring me on board as an advisor need help in understanding how to make sure they're their, uh, sales, marketing or sales messaging and positioning is, uh, optimized for the highest chance of, uh, adoption.
Yeah. What would be example of a company that you worked with over the last, you know, 10 years and maybe something that, uh, you helped them achieve? And maybe it was a strategy, maybe it was coaching the sales staff.
So, my most recent, uh, one of my most recent, um, advisory engagements was with a company called Trash Warrior. They recently rebranded, I should look it up real quick because I forgot the name, the new name, and I should know this, right? I'm part of the company, but really, um, it's called Dimension Now. The company is called Dimension. It's a 500 startups backed, um, company.
And what they're doing is making, uh, waste disposal, uh, easier for the consumer or for the business owner, and then also more healthy for the earth. So that to me, like that's something that I can get behind, right? A, a meaningful mission to, um, you know, the world is swimming in plastic. Like what can we do to help solve this problem?
So with, uh, Lily, who's the founder and ceo, um, super smart woman, went to Princeton, I think a Harvard mba, like you're talking about the top tier of intelligence. And she did. Sales wasn't her specialty. And so when we kind of had conversations, it was about me, uh, helping her kind of just understand, well, we have to, we have to architect this business in a way that is, uh, easy to understand. Again, it's a painkiller, it's not a vitamin.
Um, and, and again, the psychological messaging and strategy behind all the outbound campaigns, emails, the cold call scripts. Um, anything, right? Anything that involves external sales, uh, uh, materials, um, I wanna help, I wanna help with that because one wording or one comma period, all of a sudden it changes the tonality, uh, of the message. So, and I like doing this right? I, it gets me excited, it gets me, uh, pumped up to be able to help people who need help.
Yeah, I've been kind of refreshing up on some sales books I read before I just reread a couple months ago. The Challenger Sales, you know, um, what is it? Uh, teach tailor, take Control. It's kind of the mythology and, um, what I find interesting is just how much sales has really changed because of the internet, you know, in the last, you know, 10 years or something where, uh, before the sales people were more of the gatekeeper of the information and the pricing and things like that.
But now with the internet, there's so much information. So that's where like inbound marketing's so important where you're creating great content, you're creating stuff like, My, my favorite example of inbound marketing is HubSpot. I absolutely love their blog. I do their courses. I'm a fan of them and I don't even use, I've used their, I guess their crm, but I don't pay for their product, but I'm a champion of them. And that's like the point of it.
Like, this is a great thing you're creating, but they're creating all this great content. So eventually if I come to, to a point where I need that, that system, I'll probably go with that system. Um, so it's just a lot different in how we kind of are, are selling to people. So, um, what are your kind of thoughts on kind of the, you know, the, the changes of sales in the last, you know, in your
experience? Yeah, I mean, so it's building trust, right? Like you just, I think you literally, just that example you gave, you trust HubSpot, right? There is a relationship there. Even though that they are not receiving 1 cent from you yet you are, you have a relationship with them, you're comfortable with them. Um, I also think this, this, the entire world of sales is slowly getting out of this. um, kind of like icky or gross, like sales, right? People think like a used car salesman.
. Yeah. Um, I think it's like, for me, sales is helping people, right? And sales is educating the market on a product for service they may or may not know exists. And then detaching yourself from the outcome, right? That's, I stole that from one of my, my sales mentors, Josh Braun. You detach yourself from the outcome. You don't care if they buy or not. Why? Because you're educating them. And some people are going to buy and some are not.
And if you know that as a salesperson, you're gonna make, you're gonna diffuse this self-generated stress that you have living in your body about quota and closing deals, all this stuff, because you have this awareness that like, you know what, I'm gonna do my best and that's that I'm gonna try my best. And only you know if you try your best or not, right? Like, I don't know if you tried your best. Your boss, he or she might not know, but really you in your core, you know, did I give it my all?
Did I give it my best or did I not?
Yeah, I think that's a good point. I, I, I know this is my own experience when I've been my best is when I've had a game plan, like a daily, you know, have, I would, you know, create a game plan on Sunday for the week, then Monday morning I review it, then the end of the day admin and review the next day. And I did that. I was successful. If I didn't do that, it was just scatter brain, you know? Yeah. So like, there's, there's a strategy in there.
It's also just kind of different, you know, there's different types. It it, the thing about reading all these different cell philosophies too is that it's interesting, but also it's like you have to deal with a grain of salt. Cuz there's like, there, like when I was selling like e r p software, there's like the ban philosophy. Yeah. , Jason Komosa: yeah. Budget. That's, yeah. Yeah. Um, and that came from like, was that budget, authority. Authority need, timeline, need and time.
Yeah. And that, that's from like the sixties, like ibm. So it's like, it is, it is. Things have changed a lot. And then those different things we sell, like when I, when I worked in, I worked in college and sales at Circuit City and I loved home theater systems and I was so passionate about selling stereos. And I just as a hobby, I would tinker with stereos and I would like read all the ads. Remember newspaper ads back in the day. Yes, yes, of course.
And I actually, I interviewed for them and you know, I'm 18 and it's not like it's really a hard job to get at the time. But, but I wrote a business plan and I present it to them , that's, they're just like, And that was probably my, my favorite job ever. I would, I would come in, I would only during the school year, besides Christmas, I'd only work on Sundays. And the store manager is like, Carrie, you're the man coming here and do this stuff. And it was just cuz I loved it.
Like you said, the passion. So I think passion, and I know that's like, if you don't have a lot of passion that you're selling, it makes it hard. Unless you're maybe like kind of a sleazy salesperson who's kind of makes stuff up, which at Circuit City, I had a guy who would make stuff up and it made me so mad. I'm like, he's talking to people. I'm like, that's not even true. Like, you're just . It's like the flux capacitor and like, you know, um, back to the future kind of thing.
So maybe that, yeah. Right. Maybe that exists. Who knows now.
Um, but what I was kind of, what I was kind of getting to, there's a lot of different like philosophies out there and there's, that was a future benefit type sell, you know, and you know, now it's, you know, there's solution selling and then, you know, it's a. All these different things, but when it comes down to it, like you mentioned earlier, it's a psychology, you know, of, of, of it and like helping people out and connecting them and really finding, teaching them what, not
pushing the pain buttons so much, but it's more about, you know, teaching them something they don't know. And that's what it's really become now. It's like teach them an industry problem that maybe they don't realize they have, but it's, and then like they walk away. Even if they don't work with you, they might come back to you.
Exactly. So here's a, here's a really quick story. Um, I love the idea. So it's illumination, right? You're illuminating something they may or may not know is happening. And one of the, um, one of the sales tactics that I use that help get me a meeting with, um, the executives@jet.com, which is a Walmart company, I would actually go on Twitter cause this is when I was at Doorman, which is a doorman was a e-commerce logistics company that got acquired, but.
Essentially, I would go into Twitter and I would search@upsatjet.com or at Walmart, and then I would take a screenshot of the tweet and I would copy the tweet and I would paste it in the body of the email. So don't attach to the email, actually copy the tweet, paste it in the email so that when they open it up, what do they see this tweet about How this customer hates jet.com because their perishable package was fucked up by ups. Now the customer is mad@jet.com.
jet.com has nothing to do with it. It's actually most likely UPS's fault, but it doesn't matter. The perception of the customer is their pissed@walmartorjet.com and how they're never gonna work with jet.com again. So I would copy these, uh, tweets and send 'em to all the executives at Walmart, and sure enough, oh, now all of a sudden they're interested in having a meeting with us because they see that this is a real thing happening. And if they want to choose to ignore it, cool.
Go ahead and keep, keep ignoring it. It's still gonna happen. Or let's have a conversation, talk about how we can solve this problem. And that's what led to the actual pilot of, we did all our, all of, uh, the jet.com deliveries in Manhattan. Uh, it was crazy, but yeah, that's what started it, is this illumination of, Hey, this is a problem that's happening. If you want to ignore it and pretend it's not there, go ahead. If not,
let's talk. That's a great idea. I'm putting that into the, uh, into the, the bank there. That's, yeah. Just the clever things like that. I mean, that's actually what's fun about sales too, is like, um, is the creativity. And that's why I think why I done sales. I did sales for a long time, then I switched to marketing and I'm looking to get it back into sales is because the creativity of things. I really like that, you know, like do something different. That's what, that's what you did there.
Um, , that's
it. Exactly. Differ, separate yourself from the pack. Right. The average business, uh, let's say VP level employee gets, what? 200 emails a day? How many handwritten letters or how many snail mail pieces of mail does he receive? He or she? None. So if you really wanna win an account, how about writing them a letter, like literally writing them a letter or mailing it in and all of a sudden you have one letter versus 400 unright emails. Like what are your odds there? I would go with the letter .
Kerry Finsand: Yeah. I, I, one time for a, a job interview, I got an interview cuz like I, my resume, I, it was for like this, you know, those like sprinter vans that people like live in and stuff, or, or camping. Yeah, of course, of course. Yeah. It was a company, it was a company in Oregon that, um, they sold, they rented their vans out or they sold systems at retro, retro of those kind of vans. Mm-hmm. and.
I came up with an idea of, of making a piece of paper that would fold into one of the vans and I, I looked online and I found like a template for one. And then my friend's designer had him put like the logo and stuff on there, uh, of the van. So when I sent to them, you, the back, if you turn over the resume and the backside it has, you would fold it into a little, it could turns into a little van. Oh, that's cool. Yeah. That is cool. So I was like, I I, I like that too.
I like to get really kind of outside creative. Cause I think like, even though I didn't get the job, I got the interview and that's like, for me, I wanna at least get that. That's the win. Yeah, that's the win. Exactly. And that's like when you like submit all these different resumes and stuff all the time, it, it, it gets, it gets frustrating cuz all you want is that ability to get in front of a person and do your best. And if it doesn't work out, it doesn't work out.
But at least you gotta try versus just being, you know, a number in this, like this, this system, like if you will. A hundred percent. So my last, uh, my last company Blackheart, um, we opened up the, uh, account executive positions. The first, uh, account executive, or, I'm sorry, business development position, the very first position that we had open for sales, uh, biz biz dev world. And we got, I don't know, uh, 200 maybe applicants. And the woman we end up hiring, uh, Palu.
She didn't apply, like there was no formal application. She emailed me. She emailed Donnie, who's my friend and the CEO of Black Cart, and she basically said, Hey, I saw this role open. Here's why I'm a good fit, and here's what I can do for you. Here's where I can provide the most value. Here's why. And that was it. It wasn't like this, this long, it was just a very short three, three paragraph email. But that's what le got, bumped her to the top of the list.
We interviewed and she was the best fit. So it's like, Um, yeah. If I, for those job seekers out there, or for those folks who are wanting to break into a company, um, that they really love, don't wait for an opening. Don't wait for like an applica. Like just go at, keep going. Keep emailing people, keep trying, keep trying. Why?
Because if I'm the CEO of, of Nike and someone wants to send me their resume in a Nike shoebox, that shows me that they really wanna work at Nike and not necessarily just any old shoe company.
Yeah, definitely. Uh, it's, and I, I always look at, and I look at job hunting, um, as basically a sales cycle, cuz it is, you're moving yourself through a pipeline. And I I, I even used for a while I was using HubSpot CRM as my track and cuz you can also send emails in there, you can see if people open up the emails and stuff like that. Cuz there's h emails. Yep. Yep. You can do, I can create templates in there.
So I, I totally like, I geeked out on that and like I could track things and like, , you know, it's just, um, but that, you know, it's, it is, that's what it is. It's a sales cycle. And so, um, you gotta get creative with that.
Yeah. Yeah. And, and, and, um, again, if, if, if I'm the boss or I'm the hiring manager, I'm gonna want someone to work for me just as much as they, like, I want to have it be a two-way street. Right. I don't want someone who just wants a job anywhere. I want someone who wants a job at my company.
Exactly. Um, I'm trying to think here, I think we covered the main kind of things I was interested chatting about. Is there anything that you're excited about coming up with, with your, uh, with your company? Um, or anything you're, yeah, just obviously you're excited cuz you have a, have a newborn kiddo. So your life is very busy right now, but what's something that you're excited about right now?
Yeah, I'm actually looking at some notes here that I took. Um, I wrote jotted down before the call here. Um, let's see here. Well, one of the new, you mentioned like a, a newborn, right? So I have a newborn son. Uh, he's about, I don't know, seven or eight weeks old. Seven, seven weeks old. And one thing that I'm continuing to really like, hone in on and and kind of craft my skill is the idea of parenting yourself, right?
This idea that if you have a, if you have , a child or a pet or a niece or a nephew, you have a younger one, you have someone something that, someone that you love that's younger than you. And let's say this, this niece, uh, comes home from school and she's upset because she got a bad grade on her test, right? Seven year old niece, she gets a bad grade on our test. How, what sort of, in what sort of fashion or how would you show up?
Well, you most likely would be loving and caring and understanding. Empathetic, encouraging, positive, right? You would be showering her with love and, Hey, you know what? It's okay. We can try better next time. And. You know, all these things about positive reinforcement and showing love and care, right? And so take that, uh, theory from the seven year old niece and then take that same exact application to the 45 year old version of yourself, right?
Because what happens when we're 45 and we don't get that job that we really wanted? I'm a fucking idiot. I don't deserve that job. Why would that company ever want to hire me? I'm worthless. All this rambling negativity. Why would we do that to ourselves? We would never do that to our seven year old niece or daughter. Why are we beating ourselves up? It makes no sense. And obviously it's, it's easier said than done, but it's like, take that application of, of parenting and parent yourself.
Show yourself some fucking love people. Adults don't do that. Adults just beat themselves up. . Kerry Finsand: That's me. . That that, that's interesting. Yeah. So you're kind of that as, you know, maybe something you want to kind of ex like write about or kind of like develop something. It's like, yeah. As, as a new parent, it's like you're, you, you have, um, your infant, your child. They need, they want and need and crave so much love and, and, um, forgiveness.
And like I said, this is like at some point in our lives we like flip a switch almost, where it's like, well, we're done showing ourselves like love, or I'm sorry, we're done showing like, you know, we're not applying what we need to apply for us. We're only doing it for others, not to ourselves. And that doesn't help.
Yeah. Uh, I'll, yeah, keep me updated. That, that'd be . Interesting. Yeah. Just some takeaways. Actually, that might be good. I know you do webinars sometimes. I did one on, uh, Yeah, on LinkedIn and stuff with you and, uh, yeah. So that could be a good one for that to kind of explore people. Um, well, I really appreciate your time today. What I would like to know is where can people find you online?
Yeah, sure. So if you wanna reach me, my website, it's jk coach.me, that's the letters j k and then coach.me m e or, or you just shoot me email jason dot coma gmail.com. Um, happy to chat and yeah, like I said, uh, one life man, we're, we're on this planet. We got another good, let's say 50, 60 years left. Let's fucking make it an awesome 50, 60 years.
Let's do it. Let's go. Uh, Jason, again, thank you for your time. I always like to end the show with, with, uh, a saying, remember, you're not alone in life or business.