From the Crossroads of America in the Hoosier State of Indiana. This is Get IN the podcast focused on the unfolding stories and extraordinary innovations happening right now in the Heartland. I’m Matt Hunckler, CEO at Powderkeg, and I’ll be one of your hosts for today’s conversation. I am joined in studio by co-host Christopher “Toph” Day, CEO of Elevate Ventures, and to my right I’ve got Nate Spangle, head of community at Powderkeg.

Let’s go. Today’s guest is Santiago Jaramillo, serial Tech founder and CEO, and is now an executive coach. Very excited to talk to him on the show today.

Psychological safety is his trust that’s earned and so it’s it’s a thing that, that we earn as leaders, and so it’s. How do we react when someone tells us news that we don’t want to hear?

Santiago is a serial entrepreneur turned executive coach. He’s a first generation immigrant from Columbia, Inc Magazine 30 under 30, 3 successful exits as a founder and CEO, all scaled within the Powderkeg community. He’s a best-selling author of Agile engagement and has created more than a hundred million dollars in total enterprise value, and he did that all by the age of 33.

He also happens to be a really good friend of mine, and I’m super excited to have him on the show today as Santi. Thanks for being here, man.

Thank you for having me. Excited to be here. Yeah. Welcome back to the great state of Indiana. I know you’ve, thank you’ve had a nice nice time. What, tell us a little bit about where you’ve been the last couple months.

Oh yeah. Being from Columbia and growing up in South Florida, middle school, high school my blood vessels are made for warm climbs. And yeah, the fam and I have been heading down to Florida for the season. So we are yeah, snowboarding it up. So we got heat back here two times.

So after leaves fall and spring blooms, that’s when Indiana is home, you’re doing it right, man. I missed it a lot though. I missed the people and missed so much of it. It’s good. So good to be back.

Where are you hanging out in Florida?

Fort Lauderdale, south Florida area.

How’d you pick that?

Yeah, parents lived down there and then I spent middle school, high school down there. So just enough connections and that kind of a thing. Yeah. Less, less party than Miami too. Speaking of your childhood, you have been an entrepreneur since the earliest ages. Can you tell us a little bit about.

Your earliest entrepreneurial ventures? I think it involves produce and some pretty innovative ways of making a dollar.

Yeah. Always been a really entrepreneur. I think it was seven when I started the first one and, all the little kid lemonade stand businesses and that’s what it was. It was a avocados. I was a, all the other kids at the country club with my parents were playing in the pool and doing normal children activities. And for some reason I was hustling avocados to my parents’ friends. And, these were like highly overpriced Whole Foods. Avocados too. I was marking ’em up. I think they just bought it cuz they. They thought I was cute at the time, but yeah, so got my first sales chops that way. And then delivered some water for my neighborhood as well. And so had a, technically I had an exclusive distribution agreement with the Coca-Cola truck. Where only I could sell bottled water to our community.

And that was really great. So I cut my teeth with produce as you call it, and that’s hilarious. I was basically the OG Colombian Kroger and yeah, and then, they evolved to cutting grass and making websites and in high school and teaching kids music and then running music, summer camps.

And then it was really exact target where I, as an intern in college where I started to get to know that there’s a tech world out there and could actually combine the idea of entrepreneurship, which for me was just seeing an opportunity in the world and I just compulsively needed to fill it. I was like, oh, there’s a problem.

There’s a need, there’s a better solution here. And and this is fun. It was like my, it was a, is part of my art, I think is seeing sort of opportunity and then coalescing some sort of solution that works better than the, original thing. Has that feeling of ex nihilo like something from nothing, like creation from nothing.

Which I really enjoy. You get that from something and then if nothing, and then you have this living, breathing thing called the company that has a personality and the culture and goes on after you have departed. And it’s a very kind of beautiful thing to birth something like that into the world in a way.

So yeah. Yeah. When were you making websites? What’s that? When did you start making websites? That was high school. Yeah. What were your age? They were not very successful. They were like, I think I was 16 or 17, which, yeah. Yeah, in 2016 or 17? Yeah. Yeah. I got a little bit of a, I went to a summer camp where they taught you how to build websites and then I started making some websites and then that ended up being part of the Blue Bridge project.

Cause I had ran a tiny little custom website agency, but then I saw mobile and I saw the stats that, yeah, everybody had a, this was 2007 iPhone launch, 2008 or nine App Store launched or something like that. I think those are the rough dates. And so by 2011 we were spending more time on our phones than the computer.

And I was like, this is crazy. Like the computer change, every, the move from print to computer change everything. The move from laptop, desktop to phone is gonna change everything. And I saw that most of the time on [00:05:00] the phone was being spent in native mobile apps, not the mobile web. And so it was like, there’s something in mobile apps, I don’t know what it is, but there’s just a.

A wave coming and I wanna ride that wave without knowing what it was. The first, business plan was QR codes, SMS marketing and mobile apps. And it was like way too soon for QR codes. Those just became cool. Like it was way too early of an idea. It was a right idea, sms, like nobody was doing back then either.

And mobile ops were the ones that I just got a few bites on in college, but nobody actually bought until the visit. Kokomo, the Kokomo visitor Bureau. It was 2012, the Subaru was coming. Kokomo wanted. Some sort of visitor resource cuz people, I guess were staying as far as Kokomo for the Super Bowl.

That’s wild. Isn’t that crazy? 2012, I remember that people were all over the state for the Super Bowl, so they wanted an iOS and Android app. And I did a custom development project, lost a ton of money cuz I didn’t know how to scope and, it went over budget and everything and I was like, custom development sucks.

No, it doesn’t suck, but it’s a hard business to be in and [00:06:00] and, or I wasn’t good at it or both. And so then I was like, wait, if Visit Koko wants an app, like there’s gotta be thousands of other tourism destinations that are gonna get an app. They’re, right now they’re spending money on Physical visitor bureaus to hand out print brochures.

Yeah. Like surely it makes sense to spend 10 20 grand a year on like a, on a TripAdvisor competitor that’s native to them. And so that was that was Blue Bridge. Before we dive deep into Blue Bridge Yeah. I wanna learn you grew up in Columbia. Yeah. Yeah. How did you land in the States?

Oh sure. Airplane there, it’s yeah parents are fully Colombian, been there for generations and once particular Sunday, pretty much everybody in Columbia’s Catholic. So we used to go to mass, it was a mass in the country club, avocados every Sunday. And I was building a treehouse with my dad had just seen Swiss family Robinson or whatever, and I was like, live on the land, like wild have a treehouse.

So my dad building it, we had got Palm Frans for the roof. It’s just legit treehouse, right? And they, you gotta get ’em on the roof while [00:07:00] they’re green. Or else they’ll crack and stuff. And the way that waterproofs it is, they got a dry in place. We got the Palm Frans, they were drying. I was like, Hey dad, can we skip mask today?

And he was like, go ask mom. And so I did. And mom is in a great mood, approves it. So we’re skipping mass building this Treehouse. The church was right across the street, like diagonally across the street from us. We were building a treehouse. We hear gunshots pretty close by. My, my dad’s pretty concerned.

I don’t know the difference between a gunshot and a cow bike firing. So I’m like, what’s going on? We look across the street, there’s two big military kind of camouflage trucks outside the church, and they’re hurting. There’s these sort of armed, camouflage clothing. Looked like the army hurting people from the church into these two trucks.

And then my dad saw one of them shoot. With their semi-automatic gun or whatever into the air to get people moving. And he was like, no, this is not the army, because they can’t be doing that. It’s not safe, so he called the anti, gorilla, can I anti-terrorist? Police. And they did not believe him.

[00:08:00] But ultimately what ended up happening is a gorilla group called the E l n came into the church, told everyone that there were the army, there was a bomb in the building that everyone needed to evacuate. And he, kidnapped like over 120 people including children. Most of the children were let go that day.

They were took, put into these two trucks trucked outside of the city and basically, start walking into the jungle basically. And yeah, the elderly and children were let most of them let go. I had friends from school and, church, family and stuff, and.

Most of the adults were gone for over a year just south for ransom. So people had to sell cars and houses, and you could imagine as a kid not knowing if both of your parents are alive and your, your uncles are taking care of you. So it was a really crazy time. Obviously we were very fortunate to not have, it’s one of those times where, you know, if I had turned left or if I had turned right or if I hadn’t met this person, my life would be different.

So it was one of those turning moments where that tree house or not going to church or whatever, saved, from a lot more therapy later on. It was not an easy situation, but I gotta remember to [00:09:00] breathe. I like literally That’s insane. Hard to imagine. Yeah, for sure.

How do you think that impacted you and your own leadership and career development? Yeah lots of ways. I think one of the things that it taught me, I think a lesson about money and the importance The importance or lack of importance in a lot of ways. But I, I saw that having money is a way to get your loved ones back if they’re kidnapped.

And so getting a bunch of money was helpful because I might need that in the future in whatever children logic this is, if that makes sense. And absolutely. I think part of the entrepreneurship was actually just being like, I never want to be in a place where if my family needs me to rescue them, that I can’t do it.

And accumulating resources to keep me and my loved ones safe is important. Probably to an, that probably got taught to a, to an unhealthy degree. And I think part of the last, part of growing up is, finding choice and healing and balance and these types of things.

So I think that a relationship with money is [00:10:00] probably one of them. And then just a general, like feeling not safe in the world. Like the world isn’t you can I have, I’ve had to transcend this belief that like the world is chaotic and not evil, but like dangerous. And any safety has arrived from controlling one’s environment.

And and that there isn’t like a goodness that’s out there. It’s mostly just entropy and you just gotta carve out a place of safety because and the universe is gonna take it away from you actively. And that’s a very different. Fundamental belief about the nature of the universe.

Yeah. Yeah. And the world than other worldviews. And there, there comes, that came with a gift of a ton of like self-reliance and resourcefulness and and ambition and hard work and deep responsibility and initiative and strength and doing hard things. And it also is that belief is also limiting in a way because I think there is good that comes to me that isn’t created by me.[00:11:00]

H how old were you when this happened? And then when did you come to the state after that? I was nine. This was 1999, May 31st. It was the largest mass kidnapping in Colombian history. And then we, it took us a year to get the various immigration papers to get a work visa for my dad to and mom to start a new location for their business or whatever.

So we had a temporary work visa when we came in the year 2000. So I’ve been here 23 years this summer and 10 in Columbia. All right. So this is gonna get way out there for a quick second. But so I don’t think I’ve, I like, man, I, so many emotions are going through me. That’s just one of the most amazing, powerful things to get even wrap my brain around, that a friend went through that and I, I didn’t even know that. It’s insane. How do you reconcile or think about present day societies and then you experienced that at nine years old. Are there any thoughts that go through your mind on how things that society could do to just love [00:12:00] one another?

Just be more understanding. Embrace one another more. Even when, people might have different opinions, thoughts about things like, what, how do you think you probably, does that make sense what I’m asking? Yeah. I think of a different vantage point than part of, it’s, part of what comes to mind is exactly what you mentioned, which is like realizing that all of us have stories like mine.

They might not be as like maybe dramatic or crazy sounding it’s all relative, but Exactly. Exactly. But it’s all relative. I don’t think a kid differentiates between a mass kidnapping in Columbia and getting bullied at school or whatever, right? Like it feels awful. And it traumatizes you, and that kind of a thing.

And all of us are like just doing our best, walking around with like our beautiful parts of ourselves and also the parts, our defense mechanisms and our childhood adaptive selves. Like we’re patterns that we developed to keep ourselves, loved and safe when we were kids and are now like, Compulsive and becoming like the ways that we’re limited, yeah. In our growth and our potential. And so [00:13:00] everybody has that stuff. And when we’re able to like tread carefully and softly with people because we know that everyone has had pain and suffering in their life and any parts of them that we’re experiencing that are not very pleasant are likely, it doesn’t excuse their behavior, but it’s coming probably from a place of unhealed, pain and hurt.

And yeah, that doesn’t excuse everything, but we start with at least like an opening of Yeah. Of of empathy and of realizing that everybody has their story and we don’t know what happened, somebody’s earlier in the day. So maybe treading kindly and carefully is a better, path than, yeah.

I don’t know. Bulldozing ahead, that’s what comes to mind. I don’t, but I don’t have any societal advice. I think your story is a great illustration because that so many of the great leaders in the business world, in government, in, arts and music, you name it. A lot of times their superpower is coming from a place of some [00:14:00] sort of initial trauma.

And when I say superpower those things that you name, resilience, resourcefulness, creativity. And every yin has its yang, which is the dark side of that. Which is feeling unsafe in the world, or, not necessarily feeling maybe feeling like you have to take care of everyone in your family.

Yeah. Even if that’s not actually the case. Yeah. Oh yeah. And I think so many leaders. Certainly I feel like there are more and more leaders today that are going on that journey of introspection and learning that, and getting to that next level of leadership. But one of the things I’m excited about what you’re doing right now is that exactly, working with other leaders who have had their own traumas both as children probably in their business too, if they’re growing, any kind of business that’s growing at all, there’s going to be traumas.

Yeah. And understanding how to navigate through that. So I’m excited to talk more about that and it’s just, it’s great to hear your own story and I’m sure throughout the rest of this conversation we’ll hear more of that same pattern. Yeah. And things that you’ve learned along the way.[00:15:00]

Absolutely. I would love to dive into blue Bridge and ultimately amplify a little bit more just because you built this initially this visitors bureau, app company. Yeah. Very young age. Talk to me about how old you were. I, cuz I remember when you came to the first powder cake event.

Like you were still in college. Yeah. Oh yeah. And you came in, came from Indiana Wesleyan. Yeah. It was hackers and founders. It was Binkley’s and Mark Hill was speaking and I drove an hour and a half down from Marion, Indiana to come do that. And I was like, I didn’t know there were other people, crazy people like me doing this.

And how’d you hear about it? Heart thing That was likely to fail, right? How’d you hear about that first one? I have no idea. I have no clue. Sorry. Yeah. Great marketing. Great marketing from whoever was running the, it was just Matt’s magic. Yeah, exactly. Magic, serendipity. There, the way people found out about that in the early days is there was this new thing called Twitter and it’s relatively early platform called YouTube.

And I was sitting in the corner with a heard of them flip cam. Yeah. Taking a video of it, mark. I remember that. Yeah. Mark that. You can find that [00:16:00] Mark Hill video on YouTube still today. Yeah. That’s awesome. And I was just sitting there, no tripod, just like elbow on my knee taking a video.

And that’s how people were finding out about it, is that I would put it on YouTube, tweet out the link, and people would be like where is this? How do I, yeah. This thing. And I remember you saying that you drove an hour and a half down to be there and this kid’s gonna be okay. It’s gonna, yep.

Yes. Yep. That’s hustle, man. Yeah. It’s yeah it’s amazing to think back on that. So 21, probably 21 years old. Yeah, 21 years old. Was a junior. Junior in college. And then junior summer, I tr try to sell mobile apps for three months. Sold nothing. I just, ugh the amount, when you think about spending 300 hours trying to, three months and you just sell nothing.

So I went back to school being like, oh, shoot, I thought I was gonna be like an entrepreneur and, but I just straight up failed, at this. I didn’t get a single customer the whole summer and I was like, oh, I think I just need to get a job and take my dad’s advice, which was like, get a job, learn on somebody else’s dime, and then get a network and then, go out and go do that, which is, [00:17:00] good advice and well-meaning by dad for sure.

But didn’t end up doing that. But yeah. Then early then November after I had, gone back to school the city of Kokomo calls me and, I stepped into my office, which was my college closet dorm closet and closed the deal. And it was a 13,500, $100, a one time for an iOS and Android app.

Again, lost money. But then I was like, okay, there’s a way to list build, the hundred of these in Indiana and, around the world. And then we got, as any. Early stage founder is privy to make this mistake is not being focused enough. And so I was like if we can do apps for visitor bureaus, we can do apps for other types of organizations too.

Let’s do a five-sided go-to-market strategy with five different markets. And so we try to almost become like the WordPress for apps for all sorts of different mobile applications. And so we got like a tour, a church. Arm as well. We became the second largest church app platform in the world. So we would do, mega churches want iOS and Android apps for their congregation.[00:18:00]

We did some for university rec departments. We did for Indie 11 app for a little bit for sports teams. But we were just all over the place. We had a marketing team of three, and I’m like, you have five ICPs, and so it ultimately, we, we got it to, in a raised venture capital, I learned how to be a ceo.

E to go from maker to manager to leader is a huge, transition and what got you here won’t get you there. Kind of realization. So I learned a lot, made a lot of mistakes, but ultimately just. Our hypothesis of we can have one platform that can create any kind of mobile app was not nearly focused enough.

And we had ended up with very, at first we could do lowest common denominator functionality for all four. And it worked. And then we ran out of lowest combination denominator functionality and churches needed payment technology to accept giving and tourism needed Bluetooth beacon functionality. Just totally different roadmaps.

And so we realized we’re really running three little businesses. None of them is, I didn’t want to be just a church app platform. Tourism [00:19:00] was like too small just for mobile apps. We’d have to go into CRM and other kind of verticalized. So anyway, ultimately decided that we were gonna sell off. The two business units, the church one and the tourism one.

And so that we could focus on employee engagement apps for employers. Cuz my board really wanted me to go up market is go up market. And I was like, there is no up market in churches. Like we’re already, we already have traders point or whatever, there’s no bigger than this.

Yeah. And we couldn’t really go up market in tourism. We had visit South Africa and visit New Jersey. We had states and countries as clients, they’re tourism bureaus. So I was like, if we’re gonna go up market, I we gotta go corporate and we gotta go for-profit versus these small non-profit clients.

And so we basically, it was a bold move cuz we stopped selling those church and tourism. And so our growth peaked and in six months our growth was gonna start tanking cuz you know, you’ve got attrition and you’re not building new ones. And so I had three months to sell these two businesses before they [00:20:00] looked like crap and we couldn’t sell them.

And I had never sold a business before and I was also trying to get a third one off, the new one off the ground. And so that was a really insane time where I just did not find balance and it was very stress because of the weight of responsibility. But I got the darn thing sold. We got 8 million bucks for the tourism and church units.

They each only have 1 million ish or so of a r and. We sold no brand, no employees, just the customer. Amazing contracts and a copy of the technology. Yeah. And so it was really great. No investment banking help, just did it myself. And those were two separate transactions very spread out from each other.

They were totally separate transactions that closed within a day of each other with two different buyers. Wow. So it was just really crazy. But I learned an incredible amount. But I also frankly, started failing as a CEO because I was just super focused on selling these things and I just had no patience for anyone.

I was like, I’m working 90 hours a week you’re not doing your job. I don’t wanna hear about it. Just freaking go do your job and just get outta my face. And,[00:21:00] you have enough of those. Interactions and people start leaving and I feel like lack, especially when you’re focusing to an employee engagement app.

Yeah. And I’m like, being a really cranky, stressed out, tired, impatient, leader and yeah, that was tough. Very human. Yeah. Very human. I was doing my best, but it was not what my team needed from an employee engagement CEO at the time. We all hear about lack of focus as one of these biggest detriments to entrepreneurial success leadership success, even success in your own career.

As you work with leaders today in your coaching practice and when you reflect on your own career what are some of the things that are helpful for learning how to focus? Are there certain techniques or tricks that have worked for you or any of your clients and what I guess too, what helps.

Finally like things click. Yeah, I think it’s two things come to mind. I think one, one is I had the assumption that yeah, we can find a sales rep that can just sell to [00:22:00] visitor bureaus and to churches. Cuz like I understood how our Lego functionality work. And I was like, this event calendar is the same for a sports team, that it is for a church than it is for a tourism bureau.

But I assume that everyone was like me. And I’m not saying that I’m better or smarter than every, but it was just, everyone’s not a founder. Everyone’s spending 90 hours a week understanding the opportunity and how big the platform is and as three years of experience with for the product capability and what it can do and, all these things that are just unreasonable expectation to, to expect of others.

And I, I knew the four different ICP markets, but it’s unreasonable to expect a three person marketing team to go after five different ICPs. I maybe I thought I could, but I, this is not a good. Strategy for a team. I think that’s one of them. The two things is, I think it’s also realizing that what got us here, meaning a place where we have a thing that we’re gonna now not focus and distract ourselves with is seeing opportunity.

Yeah. Is seeing good ideas. And we see them everywhere and we are very [00:23:00] gifted at it, and we’re usually right about them. What we, and so it’s a classic what got you here won’t get you there. And what great operators do isn’t just perpetually hunt for the next shiny object and new idea, but they know how to, just like Peter Teal, just monopolize the crap out of a specific segment and be the market leader and saturated and dominated.

And then in a very careful programmatic testing way, expand to adjacent markets and do that in a disciplined way. And to know what are the markers of success. How do we know if we have achieved sufficient market product, market fit with our core to extend ourselves from there and start to fight a two or three-pronged war?

It’s like conquering Asia too early at risk. You know what I’m talking about? You just can’t defend. We all have that friends, four different, we have initially start soldiers and you’re defending eight countries. What are you doing? You’re bleeding army men, you’re bleeding army men, what are you doing?

Yeah, I think it’s remembering that not projecting ourselves onto our teams and onto others and that people really thrive with focus, can [00:24:00] do incredible things with constraints. Number two, to realize that what got us here is seeing opportunities isn’t what gonna get us there. The actually disciplined focused execution is what’s gonna get us to success once we have some amount of product market fit.

In the idea. And then to have really clear success metrics of when will we be ready to expand? Is it a particular renewal rate? Is it a particular win rate? But, if it’s like, why would you hire more sales reps if your close rate is 2%? You just have a leaky funnel.

Or why would invest more into marketing when you can’t close the deals? Or if you have 50% renewals, why double the size of your sales team to just create more revenue that’s gonna go out into a leaky funnel? It’s just being really disciplined and that operational discipline is a skill that is learned as an operator and a visionary and an innovator is, has a very different mentality than a disciplined operator.

And so I think part of it requires self-awareness of can we grow those skills as visionaries and as entrepreneurs or do we need to hire for those skills and shed [00:25:00] operational responsibilities to somebody else. And I had co-founders that were more about. Focus and discipline and scarcity of resources that brought some of my optimistic mania down into more of we can’t actually achieve and succeed with these four things.

And it takes creating a culture of psychological safety where people are willing to just be like, Hey, I know that you want me to say, heck yeah, I’m gonna go conquer those four hills. But somebody that can actually just be like, I don’t think we can actually conquer those four hills, right? I think we can only do two.

And I’m sorry, that’s not what you want to hear. And I’m sorry that’s not what you told your board. And I’m sorry, that’s not what revenue projections are after, but this is what’s actually possible and the candor and the trusts and the psychological safety for, to get real feedback from people that is, you know what I’m saying?

Yeah. How can leaders cultivate psychological safety on their teams so that they can get that pushback and can get that sort of supporting balance? Yeah. Oh, that’s such a, that’s such a narrow [00:26:00] line that we walk between. Encouraging our team to do the impossible and actually have that succeed and have inspire our team to actually go and be Sparta or something and try to take on a an army of 10,000 with, with 300 or whatever. Tap into that deeper yeah, exactly. Yeah. And so that, that is just, that’s just hard. I think just empathy wise, just knowing like what is the edge of delusional and visionary, and knowing where that line is. And I think it’s tapping into our own gut intuition to data and our team and psychological safety.

But to answer your specific question, I think, tr psychological safety is trust that’s earned. And so it’s it’s a thing that, that we earn as leaders and so it’s how do we react when someone tells us news that we don’t want to hear, but is true and it’s a helpful data point. I think how we react to that either encourages someone to be like, oh, this is somebody who values truth and a data point, or this is somebody who [00:27:00] just, you know, just is only accepting of their view of the world and me sharing any limitation, with them is gonna not be received well.

I think also it’s, I think how we handle teammates disagreeing with us in our strategy. Do we just squash dissent? Or we, and Jeff Bezos has this phrase called disagree and commit. And I think it’s really helpful because a lot of people just commit without disagreeing and then we don’t get the data point, we don’t get the objection, we don’t get told that.

The three-pronged go-to-market plan with one marketing person is crazy and not gonna succeed. But then it’s also really not healthy when everyone’s just disagreeing all the time. Yeah. And then people don’t commit, and then you’re just rowing in three different places. And I, we got up to a place where we had some co-founder conflict and we had a disagreement, and instead of like really working it out, we just each led two different cultures and just let it happen.

And that doesn’t, it doesn’t work. So it’s, which comes back to communication. Yeah. [00:28:00] Really. I know that sounds absolutely a little bit cheesy and whatever, but Not at all when starting off with culture on day one. And it, it seems like when, inevitably somebody’s gonna come to you and say, Hey, Santi, I’m said this, or did this and that and the other, and I’m upset.

And then it’s really easy to be like either to not want to address it or to go talk to that other person yourself. But making it go back through that. No. Have you talked to them yet? Yeah. One-on-one. And said, Hey, I, you said this is what I heard. Is that correct? Because it seems 90% of the time people are like, oh no, that’s not what I said.

Yeah, they might have said that, but in their brains they didn’t think they said that. Yep. Great. For your intimate relationships at home as well, by the way. Yes. Yes. Who knew that this skill that we’re talking about that’s like key to interpersonal relationships and like the first skill they teach you in marriage counseling, right?

In therapy is like one of the most important things that we need to do as leaders. What I heard you say is this that had nothing. They did that right? Yeah. That had nothing. What does that have to do with. A mobile app platform for tourism and church bureaus, but [00:29:00] that’s every day, that’s the horizontal thread of leadership and management is that we’re all in the people business.

Yeah. Ultimately, regardless of what our product is, regardless of what our industry is, we all, whatever, whoever, I guess there’s some industries we’re chap, G P T or whatever is doing all the work, but so far it’s still mostly humans. And you said it in your book, you said, no matter what business you are in the talent business.

Yeah. That’s, Todd may have said that. I don’t recall who wrote what. But yes, that’s, that is the thing. That’s very good research, man. Quick break from our normal programming. I have Erica Schwer, COO from Elevate Ventures here in the studio today. Erica, thanks for being here. Yeah, thanks for having me.

And you’re gonna tell us a little bit about this Rally innovation conference that’s coming up? Yep. So it’s the largest cross-sector innovation conference in the world. We’re gonna feature six innovation studios, so think Hard Tech software, sports tech, ag, and food, healthcare, and Entrepreneurship’s gonna.

Kinda be our catchall. I love that. So tell me what is, who’s it for? Yeah, it’s for innovators, entrepreneurs, investors, honestly, anybody probably listening to this podcast. And it’s gonna be a multi-day thing that’s happening multi-day in downtown [00:30:00] Indianapolis. Yep. People coming in from all over the country and maybe even all over the world to be here.

That’s our hope. Yep. And the dates are actually August 29th to the 31st. Perfect. And if people want to find out more information about speakers, tickets, things like that, where can they go? Yeah. So they just go to rally innovation.com and sign up for communications and they can also get their tickets. I love it.

You heard it here. Rally innovation.com. We’ll see you there. Search man. I actually have another quote from your book, agile Engagement that I’d love to talk about. And you’ve already touched on it, of like how these two cultures emerged with you and your co-founder kind of leading two different cultures within one company.

Yep. And the quote is, maybe this one is from you. A culture is bound to emerge, so you might as well make sure It’s a great one. Yeah, absolutely. Being intentional Yeah. With it. Yeah. How did you learn from that at Amplify after going down the path of two paths? Yeah. Ultimately, what were some of the lessons that you learned in transitioning that culture and starting to hone it and be more intentional about it?

I [00:31:00] think I think at first, I have this kind of right-handed way of, very natural way of being that’s natural to me of driving and charging and saying, we’re going this way. And then I got some feedback that, that wasn’t working. So I almost got too passive. And so part of this was actually going toward that conflict more directly and calmly and not just letting the conflict continue to fester.

On and on. I think it was part of it. But I also totally lost the original question that you were asking. I think you’re answering it, which is how do you ultimately start to. As you realize that there were two cultures emerging. How did you start to be more intentional and how did you grow as a leader in creating a more intentional culture at Amplify?

Yeah. Okay. So at, during the same time, I think part of where we realized is that as we pivoted from Blue Bridge to to amplify, essentially it was like the same team and we needed a different culture, but we just, we had the same people, so it was just natural to perpetuate the existing momentum of the team.

And so for us it was really pausing a [00:32:00] reset and like redoing core values, but not just as an exercise on a piece of paper, but like building it into how we hire for those specific core values. Growth mindset, being one of those values, communication, some sort of interpersonal health and communication being part of those core values, which is what some of the differences and the culture that kind of weren’t working out.

And it wasn’t that I was like, Wasn’t that I was necessarily wrong or right, it was just that the team, it was unfair for mom and dad to be saying different things. We just needed to be on the same page. And him and I tried really hard to get on the same page and we just ultimately could not.

And so it was having the courage to actually see that conflict all the way through, even if it meant one person exiting. And I was just frankly, really afraid of that happening. For all the reasons it looks bad. My board’s gonna be concerned, my investors are gonna be concerned. I don’t know, he’s been there from the beginning and so who’s gonna, replace him?

All the scary stuff that happens with. Transitioning and I just, I knew that it needed to happen, but it was a really scary thing and it took a longer than it needed to be. So it fued for a while. [00:33:00] Can we just do a PSA right now that that when you see stuff on LinkedIn and you see somebody switching companies, it doesn’t mean that anything’s wrong or bad or whatever, right?

Yeah. Things shift, things happen, opportunities come up, et cetera. Passions sometimes shift, et cetera. I always get amused. I get all, what do you think happened to such and such? I’m like, why do you care? It’s all good. Don’t worry about it. Yeah. Or call ’em up and talk to don’t start asking the whisper campaign, yeah. Santi, how many jobs have you had at companies you didn’t found that you weren’t the founder of? Two. Two. Internet. Exact Target and 15 five after I was a C so you were an intern at Exact Target? Yep. And then you’re founding this high growth tech company. Yeah. Where did you learn about company culture?

Yeah. What book did you read? What was the magic answer? Yeah, like School of Hard Knocks, you just making a ton of Yeah. I didn’t, I had never really had a manager, before I became a manager. And so it was just like voracious reading. It [00:34:00] was hiring great executives and being like, oh, you just you brought like notes to your one-on-one.

Maybe I should do that now. Love it. Or oh, you just did a perform, you just gave your team like proactive feedback every six months. Like maybe I should come up with the criteria for your job and then every once in a while Tell you how you’re doing, instead of all, I just, I think I just picked it up.

I also, I had Bill Godfrey on my board. He’s amazing. Scott Dorsey for a bit Don Aquilano John Tru from Cultivation Capital, just Ryan Ziegler from Medicine. Really great people that also knew some of this. And so between, I think between graciously reading and then I got a coach, right?

I think I, I got a coach when I realized that like my growth by absorption and osmosis and reading wasn’t quite keeping up with how quickly I needed. It was really the shift to be an employee engagement company. It felt I was like, what I would imagine like a pastor at a church feels like everybody expects you to like be perfect, like living in a glass house.

And that was the same thing with like employee engagement. Like we were literally the company based on culture. And so I had to be [00:35:00] like a perfect leader all the time. How’d you find your coach? Employee engagement, best practices? A friend, Scott Whitlock recommended Chip Knight here locally with Kairos Consulting and.

We had a lunch and I had always valued self-awareness. Like I’d always taken different personality tests and all this kind of stuff, like all of ’em. But I, and he talked to me about the anagram and I was like, this sounds sketchy. Tell me more. And I learned about it. And, I wasn’t that interesting academically in the engram then, but he described what an Engram eight was like, and he was, he self identifies as an Engram eight.

And I was like, oh why do you know me so well? And it’s not that he knew me that well, he just knew about my Engram eight archetype and could very quickly. Understand me at a really deep level that I didn’t feel like a lot of people understood me in. And I also felt like he had, he’s, he was farther ahead in his Enneagram eight maturity journey that I was.

And so that, that kind of caught my eye. And and I frankly also had gotten to a point where I had enough budget to hire a good coach. They’re not super, [00:36:00] they’re not the most affordable. I mean they’re, reasonable and great roi, but from a just, it’s not a couple hundred bucks a month, a, kind of an investment.

Yeah. And so how do you, that’s how I found the first one. The second one I found through reboot.io I went on one of their events and Brad Feld and Jerry Colonna are involved with that organization and it was really great. So you just talked about like the ROI on an executive coach.

Yeah. How do you measure the effectiveness of those dollars? Yeah. Yeah. So the other day I coached like a co-founder conflict and helped them avoid like a protracted legal battle for the control of the startup. That’s value in one session. So it’s okay. Yeah. What’s the ROI of that?

Yeah. You know what I mean? Or about a million. Yeah. Or another client that knew that a product pivot was the right thing and was terrified of what his investors and board would think of it. Especially cuz they raised like family and friends. And they knew in their, heart of hearts of the product, but they just had all in it just for months.

They had just been struggling. Can’t sleep at night can’t make a decision. And then I asked them one question of they told me about [00:37:00] this other time when they hadn’t had friends and family and how easy it was to make choices. And I was like, put yourself back.

In that time, in that scenario where you didn’t have that pressure, what would the you back then have decided? And then that was like, oh, I would do the pro product pivot. And then obviously a bunch of objections came to mind and fears of but what do I tell investors? And it’s we can make a plan for all those things, but it sounds like you have clarity.

And he was like, Yeah, I have clarity. Yeah. And they invested in the founder, and they invested in the founder. Yeah, exactly. And made the product pivot new products more successful than ever. And how do you gauge the ROI of that? Or, somebody’s having a bad day and they want to quit, and and you help them get more grounded, and, get a different perspective and all of a sudden they don’t quit, what’s the ROI of eventually that startup sell successfully? Because they stuck through it, and my coach helped me with that. Yeah. Especially my second coach. There were some dark moments there where I just, wasn’t sure if this was the healthiest place mentally for me to stay, but I also didn’t want to leave the ship what I felt was sinking in the middle of the ocean and just be like, I’m gonna take [00:38:00] care of my mental health.

Good luck everyone. Investors and shareholders and customers. I’m gonna take care of me. And is that, that, I think there are times when people need to decide to make that choice. Yeah. And I almost did, but my coach was, able to patch me up enough to get back on the battlefield to fight another day.

Yeah. And then ultimately led to, there’s some duck tape on it, sticky back up there. Exactly. And it led to a good outcome. And what were some of the other immediate benefits that you saw of getting an executive coach early on? Yeah, I think part of it is we have all these voices in conversations that we have with ourselves.

And this provides a very safe place for a third party to hear that and just mirror back to us. And then it goes from, Feeling like this crazy swirl of ideas and confu self confusion. Cuz we’ve thought about every angle five different ways. And then we get stuck in a loop in our own heads to like, oh, what I’m hearing is that you value this and this and this value that you value is not in place right now.

Is that what I’m hearing? And it’s oh [00:39:00] yeah, that is what I’m saying. And now they go from confusion to, I just got back mirrored clarity and I didn’t say anything new. I just mirrored back in a very succinct, clear way what. They said that really mattered because I’m able to observe their face and their tone and their language.

And so I’m able to see oh, you really lit up when you said that? Or you you got really like down, like when you said that, like that doesn’t seem like it’s working, right? So that would be, I think one of the things when I also, again forgot the question that originally, cause I had anything real quick.

I, I want, if anybody’s listening to this and you’re, if you’re a founder co-founder, whatever cuz people, you don’t understand what the experience is like unless you walked it right. And so exec getting a coach Yeah. Or finding a group. There’s there’s entrepreneurs organization out there.

Yep. There’s also other, you were part of that group, weren’t you? Yeah. Yeah. And there’s also I still meet once a month with a group of CEOs today. Yeah. And so do I and been for what, I don’t even know how long. 20 plus years probably. And what’s the benefit of having a [00:40:00] peer group like that therapy.

Yeah. You’re not alone. You’re not alone. And so it’s easy for us to think, oh, I’m the only one that feels this way. I’m the only one this is happening to. I’m the only, I’m the only, I’m the I I. There’s no I in team. And and so when you surround yourself with people who are experiencing those same things the highs and the lows and the medium holy cow it provides so much more head space for some kind of balance.

Yep. And it’s just, I think it’s it’s a prerequisite. It’s almost like. Investors shouldn’t invest in companies that the CEO or the co-founders don’t have some outlet once a month. Yeah. I think mirroring back is one thing. I think another question questions that expand the sense of possibility that they have.

They give them other options that they are not currently aware of. I think another one is the feeling of not alone. The other one is like access to curated resources. Somebody’s I’m raising venture capital for the first time. And they go on and they’re searching like how to, and it’s okay, just read venture deals and read how to raise money by Paul Graham and then.

Read those two things and let’s come back and you’ll be like, prepared, to raise, or [00:41:00] whatever. Or the Holloway guide to fundraising. So it’s several things in once, but it becomes this. And then there’s, when you’re having co-founder conflict or conflict with your spouse about how much you’re working or whatever those things are these are conversations that you can’t really have anywhere else.

And you’re sure your therapist can, but then somebody who has both the combination of creating a safe space for listening and reflection, asking good questions, and also has business acumen and can empathize deeply and but also help point some of the way can be really useful.

And in those conversations what I’ve observed is when people share experiences that’s where the magic happens, right? Yeah. Instead of trying to give advice. Advice, yeah. You’re, what do they call it? Guest dot. Yep. It’s like really, which is hard to do, right? It’s so hards experiences, coaching, that’s a skillset of coaching.

It’s just, yeah. I’m gonna go a little bit outta left field here cuz I, I know we’re coming close to the end of our hour together. But there’s one thing I wanted to ask you about, because one of the things I always admire about you Santi, beyond your servant leadership, open-hearted leadership [00:42:00] and just willingness to be vulnerable in that situation of being an entrepreneur and being a ceo is also sharing what you’re learning along the journey.

And I, from an outside perspective, it seems like the thought leadership that you had, speaking on stages around the world, contributing to Forbes and Inc. Writing a published book, published by Wiley, seemed to make a really big impact on your career and the success of Amplify. How will you summarize the value of thought leadership as a CEO or even just as an executive or leader?

Yeah. It can be, I think one of the things that it did was. It got the message of the mission that we were after out there. And then p it really helped with recruiting because people were like, I want to be a part of that mission. I didn’t do it for the recruiting side, but I think ultimately recruiting is maybe the most important thing that we do as CEOs, maybe other than don’t run outta cash.

It’s get the right people surrounding you. And so I think it, it helped tremendously [00:43:00] to create a really great employer brand where people wanted to. C come work because they had trust in the message. They understood that they were wanting to be part of that mission and they had leadership that they felt some sort of connection.

It’s sometimes we feel connected to these people that we follow and we’ve never met them, but we just have heard of them enough where we, start to trust them. And that, that sort of thing. Speaking engagements the book really unlocked speaking engagements and tho those were if your target market goes to events, they can be a really great go-to-market arm for sure.

And for us at first it was CEOs and so there were Vistage communities and other CEO communities that I spoke at. And then we got, every time that I would speak, we got customers. It was hard to scale that type of thought leadership because it wasn’t digital thought leadership. It was, get on a plane and speak at a thing.

And so when you’re trying to. Grow two x, you can’t just do two times the amount of speaking engagements every single year. And so actually that was one of the things what got us here won’t get us there. And we were, Adam and I were so good at speaking engagements, not scalable speaking engagements.

And it brought in so much [00:44:00] revenue that we almost didn’t. It didn’t allow our team to develop more scalable ways of generated generating demand gen, because we were, it was just, double the clo. Like we had a 15% close rate on sale, on leads that came in anywhere else, and we had 30% close rate on folks that heard Adam and I speak.

Wow. And so it just provides the brand air cover for. I believe in this person. I trust them. I’m grateful because they’ve added value already, with content and it’s it’s inbound marketing, right? Yeah. It’s what’s the value of gaining goodwill with the people early that are gonna eventually make a buying decision.

It’s just you have goodwill and they will are more likely to buy from you. What would you say to the humble Midwestern founder that’s I don’t want to get on stage, I don’t wanna make this about me, it’s about our team. Yeah. Write about whatever is authentic and interesting and valuable.

If like getting on stage, isn’t it, then maybe writing on LinkedIn. It could be it. For me my wife Kate did a lot of my LinkedIn ghost writing. I’m like a talker and not a writer, and so I would just, I found [00:45:00] someone who could understand my voice and could help me, yeah. So speaking engagements I was fine, but for anything written I, I got really great writing help cuz that was gonna be way easier than me trying to become a great writer, which is just, Not gonna happen. That’s great advice. Yeah. So that’s really great advice. Just get the right partner to help you get your voice out there and that person will ask you even if you don’t think you have something unique to share, the amount of time that you think about your customer’s problem is way more than what other people are thinking about.

So you do have things to share and, but you need someone to help, what is an obvious dumb statement that shouldn’t be said and what is actually new and insightful and what is like too over sharing and kind of awkward and what’s too canned and not, and I feel like it’s really hard to have that sense of ourselves.

Yeah. Of, of what is like a genius thought and what is just like a rote thought. Really, I don’t know the difference. You have brilliant ideas. Do we give the next morning? You’re like, that was tough. What was that you posted on LinkedIn? You’re like, this is for sure going viral and like 12 people like it and you’re like, shees.

All right. A good editor [00:46:00] is more, objective. It can be like, that was really good. That was gold. And like I would cut that. And so I think having a team around you is helpful. What I’m hearing though is it really is table stakes if you want to be a leader or an executive.

To figure out some way to put your thoughts out there in a more scalable way than a one-on-one conversation. Yeah, for sure. Yeah, it’s, it may not be authentic to everybody and it may not be necessary. There might be peop maybe everyone, I guess could be your employees are online, so on an employer brand, it’s gonna work every time.

But yeah, on the go to market side, you may not have people that are on LinkedIn, so maybe it’s not useful to be there, so I think it’s, it goes back to good marketing, which is like knowing your audience and where are they at, and then be wherever they’re at, be there and people, right?

Goes back to people wanting to work with you and Adam while you were on stage. You’re, oh wow, they’re captivating. I wanna work with the, not this brand, it’s. Santi. It’s the people. Yeah, I think that’s, you’re touching on. Yeah, it’s, I think Tim Cop was talking about this. It’s it’s not b2b.

It’s not like b2c. It’s just like [00:47:00] business to human. Like people wanna buy from humans, bmp. And that’s why all these videos are like shaky and stuff. Cause it’s like authenticity is important more than it is about, produce edits and stuff. Like people want the realness. Cuz we’re surrounded by so much fakery.

We just want the real, we’re hungry for the real can. Tell us, can you tell us about what you’re doing today with real founders, real executives, real leaders around the world? And how people can engage with you in what you’re doing? Oh, sure. Yes. So I’m coaching CEOs and founders and it’s executive in leadership coaching.

So I meet with my clients twice a month and I, I get really good at understanding their goals and who they are and do a lot of intake about, what are their childhood adaptive mechanisms and where are they? Is it holding them back? And it’s equal parts business therapy.

And also, it’s helping them understanding how are you doing in your life, one to five, how are you doing in your work life, one to five, and what would make it a five? Getting really clear on what it is they want. Getting really clear on what their vision is, getting really clear on how that’s communicated to their team.

[00:48:00] Making sure, one of the biggest things I see is founders sacrificing their health for, and so it’s like the basics of are you sleeping, are you working out are you having one-on-ones, with your team? And then just really reacting to the main fire that they’re bringing. So that looks like, how do I fundraise or I have an underperforming employee what do I do where I’m having issues with my co-founder, or we have hit a new milestone and I need to reinvent my job and I need to go from manager to leader and I need to hire an executive team.

Like how do I not mess that up? So it’s all of these really deep questions are like, Hey I’ve lost my mojo, like I used to love this and I’m not feeling it anymore. What changes am I done? Should I hire a C O? Should I hire a c e O? Do I get out like these are questions that they’ve maybe never allowed themselves to ask and think about.

And, but most of the time it ends up being how can a founder be in their zone of genius, the zone of things that they are really great at, that really gives them energy. And how do they [00:49:00] put more attention and more priority at finding capital and humans to help offload the areas that they’re not zone of genius.

The amount of damage that we cause by holding on to areas of the business that we shouldn’t even, beyond not having resources to to have that is, is tremendous. And so that all begins with, some self-awareness, some situational awareness, and then some courageous decisions and some really tapping into.

The deepest parts of ourselves to know how to proceed in the face of these really big questions that they’re bringing. So for me, it’s an honor to both help them perform and slay bigger dragons at work and also become more resilient calm, grounded, peaceful, happier individuals. And that’s what I really love is I get to work on their business and making it better.

But ultimately I think the gift of great coaching that I got from it was not just becoming a better CEO and my ARR growing faster and sure it did that, but also gaining more self-awareness, becoming a better listener, [00:50:00] understanding how to navigate conflict better, how to give another human constructive feedback in a way that they receive.

Understanding how I’m showing up in a way that’s not working for other people. Like these are skills that my wife and my friends and my family like sees the evidence of. Cause I think, I really think that one of the biggest secrets out there is that the path to. Leadership excellence is the same path as human development and human maturity.

I don’t think that we can actually become better leaders unless we become more whole healed humans. And I think pursuing leadership and pursuing maturity as humans is actually the same path. And that’s a beautiful, that’s what I love is it has great roi but it but not just monetary. ROI has this kind of human meaning fulfillment side of it for me.

And that’s the duality of, that’s what I’m really enjoying. I’m excited. I’m excited for you, man. And it’s great to hear some of the stories you shared here on the show today. We’re down to our final two [00:51:00] minutes and this is Nate’s favorite part of the show. Yes, sir. This is the lightning round.

All right. All right. So rapid fire, first thing that comes to your mind. All right. You ready? Yeah. Outside of the amazing entrepreneurial ecosystem, what is Indiana known for? What is Indiana known for? Hospitality and kindness spoke with a true tourism executive. Yes. I love it. Yes. Okay. Ready? What is one hidden gem in Indiana?

The White River. I think I like kayaking, but nor more north than here, but yeah. Okay. Yeah. Can you tell us a little bit about your relationship with the White River real quick? Yeah. Yeah. I love the river. So I live on the White River up in like 75th and Keystone area. I put in a keystone at the crossing and kayak and float down to my backyard, which I really love doing.

Where you can boat or kayak from my house to Broad Ripple. There’s like a dock in a broad ripple and that’s pretty sweet to boat, to dinner. And yeah, it’s like just a, I love, I don’t, there’s something about water that’s calming. There’s something about flowing water that’s really calming and it [00:52:00] feels like.

You’re like in Brown County with like really tall trees and water and there’s all sorts of, the bird songs are, incredible cause there’s so many birds and wildlife. So it’s this really hidden gem of un unspoiled nature almost. And in the heart of Indianapolis Santi, we’re neighbors.

That’s right in my neck of the woods. Yeah. I’m on the little pergola that looks over the White River. So maybe I’ll see Yeah. Right there. Yep. As someone who’s been to a hundred plus cities around the world, it is very unique that we can like, be in the middle of our city and it feels like we’re on a state park.

Yeah. Like on a river, in a state park. Yeah. It’s so cool. For sure. And it’s really cool to kayak by your house and be able to pull over and Oh yeah. Grab a beer on a Saturday afternoon. Oh yeah. A little cab. Brew trip, gentlemen. Yeah. There we go. There we go. Yeah. All right. Final question. In the lightning round, who is someone that we need to keep on our radar?

Someone who is doing big things. No wrong answers. Yeah, I’ll go with I’ll go with like Chip nighty. He does great work around leadership stuff. He does really great work around the anagram. I really [00:53:00] think that the anagram is like a deeper self-awareness tool than most stuff out there. People, some people can be really annoying about it.

So if you can get past the people telling you’re type and, reducing you down to a number or whatever it’s a really powerful tool. And he’s doing really deep work around self-awareness with that in the workplace in a way that’s different. So I think locally in terms of leadership big fan.

Great answer. Love that. Santi, thanks so much for coming here and sharing some of your journey. Super excited about this chapter for you, working with thank you, with clients sharing your own experience and thanks for sharing that here today. Of course. Thank you all for what you do for the entrepreneurial ecosystem.

I have been a beneficiary of the infrastructure that you all have laid out from hackers and founders to Verge, to Bow, keg, to, to elevate. We received funding from Elevate at Amplify and through some sort of vehicle. And so just thank you very much. Your work makes it easier for everyone else rowing their boat.

You’re building the infrastructure that makes it easier for the, for those in the arena right now. So keep up the great work and thanks for highlighting great [00:54:00] stories. Thanks, man. It’s awesome. Thanks San. This has been get in a Powder cake production in partnership with Elevate Ventures, and we wanna hear from you.

If you have suggestions for our guest or segment, reach out to Matt or Nate on LinkedIn or on email to discover top tier tech companies outside of Silicon Valley in hubs like Indiana. Check out our newsletter@powderkeg.com slash newsletter and to apply for membership to the Powderkeg executive community, check out powder keg.com/premium.

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