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The Dreamfuel Show is a research expedition to uncover and unpack the mindsets of impactful tech founders and executives. On this show, we’re going to get real and talk about what was actually going on in their hearts and minds during the harrowing journeys that forged them and their companies! We’ll also speak with performance experts who will share the latest tips, tools, and tricks that can help us realize our own dreams, too.
As we like to say at Dreamfuel, every quarter is a hero’s journey. So be sure to hit follow to join us along the way.
Adam Weber [00:00:00]:
Success often feels like failure. Most of the time, it did for me. Even when you say, like, oh, they sold for 50 million, I still have a thing that happens inside of me that's like, it could have been more.
Kevin Bailey [00:00:14]:
I'm Kevin Bailey, CEO of Dreamfuel, and this show honors founders who are stepping through fire on their quests to realize their dreams. We dive into their failures and successes and the mental performance skills they're using to achieve their goals in less time and with less frustration. Enjoy the Dreamfuel show show. Welcome to the Dream Fuel show, everyone.
Kevin Bailey [00:00:35]:
I am here with two of my good friends and people who I've worked with along their journey, Santiago and Adam. And they have been truly through remarkable heroes journeys as founders, entrepreneurs, and friends. They have three exits under their belt together as co founders and a remarkable story. They are the co founders of Emplify. Emplify Meteoric rise in our hometown of Indianapolis. Ended up having an exit to 15Five, which is another great company for $50 million. Kind of the crowning achievement of these two. And they are both executive and leadership coaches now, helping people like you find their joy and find their presence and find, as they're doing their own founder and executive runs.
Kevin Bailey [00:01:23]:
We actually just did some pretty deep, somatic breath to really get in the moment here. And I asked them, I said, you got 100 founders listening to this who were in your shoes when you started Emplify, and what stories do they need to hear to really help them with their mental performance and their mindset? So that's kind of the tee up on this. As you know, we're all about heroes journeys. We're all about founders telling the stories of what was going on in their minds and their hearts as they did these heroic journeys that have a very low probability of success. These are two who reach success, and I'm sure they have some great stories to tell. In fact, I know because I worked with their sales back in the day as they were working on some sales targets, doing some mental performance coaching, and I've had some great conversations with both Santiago and Adam. So let's jump in, guys. Welcome to the show.
Adam Weber [00:02:08]:
Good to be here.
Santiago Jaramillo [00:02:09]:
Same.
Kevin Bailey [00:02:10]:
Very impressive what you guys have done together. I know personally, you guys have had some real heroes journeys on this. Let's jump to one of your favorite stories to tell about some of the hardships you guys went through as you guys did this miraculous. What kind of the first thing that comes to mind that founders and leaders would really benefit from hearing?
Santiago Jaramillo [00:02:28]:
I think, for me, the thing that came up during the breath work, there seemed to be something kind of full of synchronicity, kind of a thing, like meant to be ness about how Adam and I met. And as much of the entrepreneurship journey is full of agency and autonomy and make it happen yourself. Good things happen because you go out there and expend effort and make it happen. There's also some really beautiful, unexpected things that the universe brings without you necessarily doing a whole lot. And I think how we just met won't go into the story, but this gentleman named Will Davis, who we both were big fans of, just had this kind of coincidence. That's too much of a coincidence for it to be a coincidence, kind of a thing of how it happened. You know, it's almost like the universe brings you the right people and the right experience at the right time to help you through. And before that, it really felt like I was alone really doing it.
Santiago Jaramillo [00:03:31]:
I mean, I was working with other people. But then when I met Adam and we started to work together, I think from our very first coffee, I just kind of looked at each other's eyes, and we're just, oh, like, there's something here in terms of, I think we're meant to do something more than this coffee and kind of go on a journey together, and it didn't make any sense. Adam was a successful sales executive at a local firm, making great money working with his friends. And I was a 22 year old college with two children in health insurance with his job. And I was a 22 year old with a big dream and a lot of ambition and drive, and it just. I can't imagine that made sense on paper for Adam to join this crazy kid who might be the world's greatest charlatan or he's super legit, and it's like, one of the two, you know? And then, you know, how are we gonna pay for health insurance for the kids? And that was an important discussion, of course. And so when I look back on it, our paths just, you know, we're individual people, and they just came together for 2013 through 2023, about ten years, basically, and then diverge. And I, we're still friends and collaborators, but in a very different way than being co founders.
Kevin Bailey [00:04:47]:
So you kind of knew in the moment when you met Adam, this is an important meet. Like, this is gonna be something big. Like, you could feel it sort of in your being in that moment.
Adam Weber [00:04:57]:
You know, what's wild is, like, I left that very first coffee. Like, he just sent me a cold DM on Twitter that was like, can I grab coffee with you? I left that coffee. I was a song, like, wrote a lot of songs at the time. And I actually remember I went home and wrote a song that said, the first line of it is, today could be the day that everything changed. And it didn't feel as strange as I thought, because we just sort of. There was a look in the eye of, like, somehow we've never known each other, but we, like, knew each other. Yeah. And, I mean, I wasn't that successful, to be clear, before this.
Adam Weber [00:05:25]:
Like, I was actually. It was like, there was some part of it that the timing was perfect because Santi had a level of, like, belief in himself that I still didn't have in myself quite at that time. And he knew that he could do this thing, and I had just gained enough skills to be like, I'm ready. The health insurance part's funny, because my boys were three and four years old. I'm married. I'm ten years older than Santi, and he's over at my house with a spreadsheet up, pitching to my wife. He's got two customers. I mean, it's the first time in my whole career, that year, I'd ever made six figures.
Adam Weber [00:05:57]:
Was that years? Rest of the time, I was in nonprofits. Nonprofit work. Before that, I'd finally had one good year of my whole career. And he's sitting here, like, going, you should start over. And he's sweating. I'm nervous, trying to figure out how my wife's gonna feel, and, like, he walks out the door. And my wife also was like, if you don't do this, you're gonna regret it for the rest of your life. She could just tell.
Adam Weber [00:06:20]:
It was, like, something we were meant to do together.
Kevin Bailey [00:06:22]:
Incredible.
Kevin Bailey [00:06:23]:
Yeah. I mean, obviously, you hear stories, like, you know, love at first sight with my wife and stuff, but, like, founders at first sight, like, you guys. You guys knew it. That is so cool. I've had similar experiences with, like, my co founders from Slingshot. Something in, you know, is like, this is. I can remember the night, like, when we all hung out, and it was just like, we started brainstorming and ideas started flowing. It was like, almost like the universe was just flooding us with knowledge and flooding us with inspiration, ideas.
Kevin Bailey [00:06:50]:
And life changed from that moment on for us. For me, too, so that's amazing. All right, story one. Beautiful. What's another story that 100 founders who were in your shoes at the beginning of Emplify need to hear.
Adam Weber [00:07:02]:
One of the things that came up for me in the breath work that wasn't something we talked about in advance. But this prevailing thought that success often feels like failure most of the time, or it did for us. It did for me. Even in your intro, when you say, oh, they sold for 50 million, I still have a thing that happens inside of me that's, like, it could have been more. And I think the reason that I feel that way, too, is, like, I know deep down what we're capable of and, like, the operational, like, excellence that we held ourselves to, and I've seen a lot of other businesses, and, like, I know that we had. I genuinely believe we had something far greater than that. I mean, one thing, honestly, is that you can't fake product that the market doesn't want or at the scale. Right.
Adam Weber [00:07:46]:
If you really want to build a company of great scale, it has to be in alignment with what people want to. You know, for the listener who's a founder, who's early stage to just take peace, and, like, along the way, we're getting. We also got tons of public accolades. I mean, partially. Cause Santi's, like, very charismatic person, and he was really young and doing all these incredible things. And so on the outside the whole time, we're getting lots of affirmation. And on the inside, even to this day, when you're doing the intro, I still feel this, like, hit of, like, oh, man, we could have been so much more than that.
Kevin Bailey [00:08:17]:
That's so crazy to think about. It's like $50 million. That's dream money for anyone. When your company built that kind of value, and still our egos and stuff push us to the point where we can look back at that and feel that in our gut. Like, I had more. It could have been more. That's a great reveal right there. And for anybody, I don't care if you're who you are.
Kevin Bailey [00:08:39]:
It's so much that you guys build, so much value, and I feel like you guys should be so proud of your accomplishment. I'm sure you are. But you revealed. Yeah, during the breath work, you felt that in your gut. Santiago, do you have anything to add to that?
Santiago Jaramillo [00:08:50]:
Yeah, I was super clear. The goal was always $100 million outcome, and we built the team and refund raise, and we built the cap. You know, everything was sort of engineered for that outcome, and we got halfway there, and there's definitely. There's more integration now after a few years, but there's a part of me that looks back on a ten year old colombian immigrant. That's when I came to the states that had to, like, navigate this country and the culture and the language, kind of by myself, and just incredibly proud that I even just built a company that had payroll, that had real adults working for it, and that raised money and that sold. And then there's a part of me that's just like, yeah, like, you set a goal for 100 million, and you failed. You did not get to your goal, and you promised your co founder and people and investors a certain outcome, and you did something really 95th percentile in terms of world class ness, but you promised them 99%, then you let them down, you know, and so there's another part that's that, like, there's an incredible pride and gratitude for it, and then there's. There's also grief that comes along with it as well.
Santiago Jaramillo [00:09:57]:
When you put ten years of blood, sweat, tears, nights, you know, your physical.
Kevin Bailey [00:10:02]:
Health, your mental health, your family's kids.
Santiago Jaramillo [00:10:06]:
Gave it truly everything with that. I don't. I don't have regrets on that part. Cause I just could not have tried harder.
Adam Weber [00:10:13]:
Right.
Santiago Jaramillo [00:10:13]:
You know, same. Maybe trying 20% less might have been healthier and a better outcome.
Adam Weber [00:10:21]:
Well, you even said something the other day that I actually just brought up with someone I'm coaching where you were, like, right now, because I don't have that same level of, like, I'm every ounce of every bit I have. You're like, in some ways, I'm actually better. Like, I'm better because I'm more objective, I'm more measured. And I think about how often we both. I mean, one of the things we both cared, we both were working, I think, deeply from a place of. I don't know if it was fear or just desire. Like, we were both very hungry, and we really, really wanted this thing to work. And I think we both cared a lot.
Adam Weber [00:10:55]:
You know, like, we gave every ounce that we had. And so I definitely leave, too, with. And, you know, it's kind of fun doing this. Three years later. It's been or four years. It's been four years since we did it, and it still feels fresh, but it's like, it took me, honestly, three years to even heal from trying that hard for so long. Like, it took some time.
Kevin Bailey [00:11:12]:
Yeah, it's like, there's no off season for founders. You know, it's like your off season is after you sell, and normally that off season is multiple years just to recover from it. That prompts me to the boat that we went on Santiago, where we were talking a little bit about you got you contemplating exit and stuff like that. And I could back in the day when I was really just starting dream fuel, I mean, we were working with Emplify, and now we do work with 15Five. But, you know, I was more just talking to you as your friend, but also kind of giving you a little bit of coaching. And I could just see in your eyes, like, you were just getting to the point where you felt almost spent. I could see you were just flirting with burnout. And I'd love you to talk a little bit about that time and the decision that you did make that, hey, I'm ready to move forward with probably an acquisition or something like that.
Kevin Bailey [00:11:56]:
Yeah.
Santiago Jaramillo [00:11:56]:
I think the journey that kind of led to there was, I think, from a somatic and neuroscience kind of physical perspective, I think what I've become to realize is that it's an intense journey. And when you care really deeply, even the little things can, like, trigger the nervous system into an activated state. And then over the years, I just kept spending more and more time in activated nervous system state.
Kevin Bailey [00:12:20]:
Right.
Santiago Jaramillo [00:12:21]:
This is the nervous system state that we evolved to. When we're, like, running away from, like, a predator, like, we're supposed to have these little bursts infrequent of adrenaline. They're supposed to keep us safe and alive, right? And our whole body is, like, just about survival, and we're just not supposed to live in that world. It's incredibly taxing physically to be that. And I think I just started to realize smaller things are activating me into being triggered or into this, like, threat, risk aware kind of state, and it's harder to get out of it, and I'm spending more and more time in it, and I was just starting to, like, sense my body being like, we can't be in this state. Something's got to change. And when you're just, like, in that river for so long, I mean, this was like year eight or nine or something like that, right? Out of the ten sort of eleven year journey, you build these deep grooves in your mind, right? The more that we repeat these patterns of external stimuli, triggering me, the deeper these grooves get and the harder it is to get out of it and change without fully getting out of it, if that makes sense. And so I started to feel like, boy, I'm a little stuck here.
Santiago Jaramillo [00:13:27]:
And when you're in that triggered state, you're not your best, most resourced, trusting, loving, joyful self. There's more fear than love from a motivational perspective. And so I think I was just recognizing, like, oof. At what point is the level of heat in this crucible when does it have diminishing returns on what's good for me? Because I think some heat, and a good amount of heat is good because it purifies the impurities and makes me look in the mirror at the childhood trauma and the defense mechanisms and the automatic ways that I respond to things. But then there's just, like, a certain amount of difficulty level that just becomes overwhelming and almost, like, beyond. And so I started to ask the question, which I had never allowed myself even to ask of, like, is this, do I need to get off the ship just for my own mental health? But I just. I felt the weight of the promises that I made to Adam and the sacrifices he made and everyone else, and I just felt like a captain in a bad storm, just being like, I'm going to take the dinghy and I'm gonna head to shore. I've gotta, like, take care of myself.
Santiago Jaramillo [00:14:34]:
You guys figure out how to land this plane, you know, or get the ship back in a safe harbor. And I could just. Even at the awareness of my own suffering, beyond healthy suffering, you know, I could just tell that I was just stuck in that moment in that boat ride of, oof. This is a bit too much, and it's been too much for a while, but I can't abandon the ship. You know, I've got to figure out how to steer the ship into the safest harbor possible. What's the nearest safe harbor? So that then I can go and get off the boat and go get help and make sure that everybody's okay.
Kevin Bailey [00:15:10]:
Hey, it's Kevin, and I hope you're enjoying the show. I know it's tough out there right now for tech leaders, and we appreciate you taking the time to focus on your mental performance and well being. Speaking of time, did you know that 76% of tech leaders lose 20% or more hours of productivity a week due to stress, fatigue, and feeling overwhelmed? To win these hours back, leaders need to learn the mental performance skills that keep you in the zone, where research shows that executives are five times more productive. And that's where we come in. Dreamfuel's octane cohort is our flagship mental performance program, built for tech leaders under pressure who want to achieve their most ambitious goals in less time and with less frustration. To learn more, go to dreamfuel.com octane, or just click the link in the description to see if you qualify.
Kevin Bailey [00:15:54]:
All right, back to the show. Wow. What a share, man. So in that moment, you realize that you just weren't your best self anymore. You were CEO of the company, and you had to find a safe harbor for the ship, but you weren't ready to abandon ship. Funny that we were on a raft basically talking about this, but you're like, I can't jump out of the ship, so you're not going to quit, but you had to find the best outcome for the company, which is what you did. Adam, what was going on for you around that time?
Adam Weber [00:16:22]:
I mean, first off, that was like, that feels fresh. Like, it feels fresh. I was very much with him in that, and I really remember a conversation we had, really, toward the end, where we kind of knew it was the end and it was time to transition, to find an acquisition. And I think that it was, you know, it was tied to that. It was kind of like, do we have the stamina to keep going? Do we have the stamina ourselves? We spent ten years doing this. We know what it takes. And do we have kind of more time to do that? And I think that that was part of, like, I mean, I think there were other factors, but I do think that that was one of the things that helped us both know, like, hey, we started this together. Let's end it together.
Adam Weber [00:17:04]:
Let's figure out a way to make this positive from here to the end.
Santiago Jaramillo [00:17:07]:
That's well said. It's obviously not the same, but it felt like you just finished a tour of duty in a war zone and you just got in it. We either need to de enlist or we need to sign up for another five to seven year tour of duty. And we just both looked at ourselves.
Adam Weber [00:17:23]:
And we're like, don't know if we have an unknown tour of duty. You're like, I don't know if it's going to get easier. I think it's actually about to get.
Santiago Jaramillo [00:17:30]:
Harder, and it, frankly, was about to get much harder. Like the interest rate sort of phenomenon thing and everything that it did to just startups in general, but specifically what it did to hr tech of companies like investing into culture, the waters got way choppier, and so it was just kind of like, this is going to be like five, seven, probably ten years before we, like, get to calmer seas. You want to, like, be thrown up over the side of the boat every night. Cause it's turbulent out there, and it's just like, oof, we've done that a lot. Maybe this is the time to spend some time on shore and deliver the ship to the harbor. Even if we didn't find El Dorado in the way that we hoped, I.
Adam Weber [00:18:09]:
Do think the reality of that time, too, was. It was hard on us. We have had a great relationship, and it really was really challenging on us. I'm proud. The thing I'm proud of when I look back on it is that we said what needed to be said to each other, and it still took time for us to heal ourselves and heal our relationship with one another, find our deep friendship with one another. But, like, it was hard, you know, we, like, went through a really hard thing together, and we had moments that. It was like, I can't believe we get to do this together in moments that were just, like, so painful and so hard between the two of us, too. And I was just telling him before, I was like, Santi knows a part of me that even my wife doesn't know.
Adam Weber [00:18:50]:
And I have a wonderful relationship with my wife, and she's the person I'm close with in the whole world. But he's seen aspects of myself that no one else has seen, I've revealed as parts of myself. It's a sacred relationship. But with that, it's. You go through moments like that, and it's like we've been through some shit together. I'll say, like, we went through a lot together to earn being able to sit here and talk. And I think the reason we're able to sit here and talk about it is because along the way, we did have really hard conversations with each other.
Kevin Bailey [00:19:16]:
I mean, I wasn't in war, and you made the war analogy. I did recently listen to a Navy SEAL who was talking about how he can just never make friendships like he had in the SEals because of what they went through. And he knows his brothers and the seals better than anyone else in the world and outside of his wife will just never have a relationship like that again. So I think it's cool that you guys share that special bond that happened in the trenches going through maybe what's not a physical war, but there's a lot of psychological warfare that happens as founders, for sure. The end of the show, we're going to talk about how this experience has changed you as people. But is there any last story you guys want to tell before we get into how you guys have changed from this hero's journey?
Adam Weber [00:19:56]:
My kind of, like, pivotal moment. I started leading sales for our first for Blue Bridge, and then the early part of Emplify. And then as the company scaled in my mind, I was in VP of sales mode, like, for the rest of my career. As the business scaled, we made a decision to transition me out of that role and find, like, a more like not a co founder led sales. And there was this moment where I was like, oh, like, this is the end for me. Because at that time, all I could see of who I was as a person in a career was, like, leading the sales function. So I was like, I guess this is the way the business is saying I'm at the end of my journey, which I was definitely not, but that's how it felt in the moment. And Santee was like, why don't you go to Montana? Go on this leadership retreat? And he went too.
Adam Weber [00:20:37]:
He went on this ten day retreat, and I had no job basically, inside the company other than the title of co founder, but with nothing, like, trying to figure out and reorient myself. And it was really through that week that I started to really ask myself, like, but why did I actually say yes to this journey? Like, why did I start this business for me? And it was really, like, through that when I started going, okay, I check my retirement account every day, and I keep asking myself, how long do I have to keep doing this? It's like, maybe I actually don't like sales as much as I thought I did. For me, I love leadership development. So it was just this really. I guess what was cool about it for me was that this outcome I didn't see coming was clarity on the rest of my career. I kind of had this moment in Montana, in the middle of these mountains, where I was, like, realized, like, what my why genuinely is. And it took me a while to get comfortable in that transition, but it also, like, I have so much gratitude that really, this thing that ultimately was honestly the hardest part of the whole journey for me was that transition and feeling kind of like a failure to being the very thing that, like, opened up and, like, unlocked me and allowed me to work more in a way that's connected to who I am.
Kevin Bailey [00:21:48]:
Got it. So kind of going back to the universe again, giving these opportunities to evolve and change as a person within this hero's journey. Great. Cher, I want to go ahead and wrap us up here. So I just want each of you, in, say, 60 seconds or less, explain how this journey, building these companies together and exiting from them has changed you as a person. We'll start with you, Santiago.
Santiago Jaramillo [00:22:12]:
I think I became significantly more aware of the compulsive reactions and ways of being that were, I think, I created to keep me safe in childhood that no longer made sense to hold onto as an adult. I think, overall, Jerry Colonna has a book called, Reboot: Leadership and the Art of Growing Up, and I feel like I grew up, you know, I think I was like a kid, very ambitious, driven, talented kid. But I think I sort of exited the crucible and the whole journey as a man. And also I think I learned this other way of being in the universe. One of them is the universe is chaotic and going toward entropy, and anything good in my life comes from my own control of my life and the variables and making good happen. And the universe is going to take that good away. And I must be hyper vigilant to protect it. Where I think it got balanced with this other kind of, like, good things just also happen.
Santiago Jaramillo [00:23:13]:
And I can trust and I can have faith and I can surrender to the river and not always paddle upstream, but sometimes just also really float with the current and having the discernment of when to do each. So I think that's what comes up for me.
Kevin Bailey [00:23:28]:
Love it. Santi.
Adam Weber [00:23:29]:
Adam, I mean, I feel like ten years of venture fast forward so much of your life and all these scenarios that you would face over the course of a whole life, you get to face in, like, rapid succession. And so I feel like I grew just so much as a person from a maturity perspective, from being exposed, like, finding all these shortfalls in myself. And then I think in the middle of that kind of recognizing, like, what I'm actually capable of, too, and not being embarrassed about that, being, like, comfortable to go acknowledge what things I'm actually good at. I don't think I knew I was as talented as I was, to be honest. That sounds so okay. That sounds so weird to say. But, like, I just didn't. I genuinely didn't really believe in myself, and it took me, I think, this journey to kind of start believing in myself.
Kevin Bailey [00:24:17]:
Amazing shares, guys. Just to wrap up real quick, Santiago, how can people get in touch with you as a leadership coach?
Santiago Jaramillo [00:24:23]:
Sure. I'm at withsanti.com and my email there is grow@withsanti.com awesome.
Kevin Bailey [00:24:34]:
Adam, how can people get in touch with you as a leadership coach?
Adam Weber [00:24:37]:
It's adamweber.co and I post all the time on LinkedIn and on the side. Right now, we're both having fun doing strategy together. We're doing little side projects together, helping companies build their strategies and execute their strategies. We're having a ton of fun doing that stuff together. Together.
Kevin Bailey [00:24:53]:
I might need to talk to you guys about dream fuel. Cool. Well, I want to give a quick shout out to Share Your Genius for doing all our podcast production. They've an amazing partner do amazing podcasts. Adam Santiago Holy Cow. That was an amazing podcast. Thank you so much for being honest and sharing your heroes journeys. This will impact and help the hundred founders who were in your shoes ten years ago who are listening to this.
Kevin Bailey [00:25:14]:
Thank you.
Kevin Bailey [00:25:16]:
Hey everyone, hope you enjoyed the dream fuel show. If you'd like to continue listening to more episodes episodes, subscribe to Apple, Spotify.
Kevin Bailey [00:25:23]:
YouTube or wherever you get your podcasts. We'll be here every other week.
Kevin Bailey [00:25:27]:
And if you want to learn more about Dreamfuel's octane program for tech leaders, go to dreamfuel.com octane or just click the link in the description.