The Real Secrets Behind Executive Coaching with Santiago Jaramillo

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 Hunter CEO at powderkeg and I will be one of your hosts for today's conversation I am joined in Studio by co-host Christopher Toph day CEO of Adventures and to my I've got Nate spangle head of community at powder K 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 trust that's earned and so it's it's a thing 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 foreign O is a Serial entrepreneur turned executive coach he's a first generation immigrant from Colombia Inc magazine 30 under 30. three successful exits as a founder and CEO all scaled within the powder cake Community he's a best-selling author of agile engagement and has created more than 100 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 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 think 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 Colombia and growing up in South Florida at middle school high school my blood vessels are made for 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 back here two times so after leaves fall and spring blooms when Indiana is home you're doing it right man I missed it a lot though I miss the people and missed 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 of seven when I started the first one and all the little kids Lemonade Stand businesses and that's what it was it was avocados it was 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 them up I think they just bought it because they thought it 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 a exclusive distribution agreement with the Coca-Cola truck where only I could sell bottled water to our community and that was 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 in in high school and teaching kids music and then running music summer camps and then it was really exact target where I in as an intern in college where I started to get to know that there was 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 this is fun it was like my it was 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 X 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 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 you're not very successful they were like I think it was 16 or 17 which yeah in 2016 or 17 yeah yeah I got a little bit of it 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 bluebridge project because I had ran a tiny little custom website agency but then I saw mobile and I saw the stats that everybody had it this was 2007 iPhone launch 2008 or nine App Store launched 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 changed ever the move from print to computer changed everything the move from laptop desktop to phone is going to change everything and I saw that most of the time on the phones 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 want to 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 this was way too early is the right idea SMS like nobody was doing back then even in mobile apps 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 that is 2012 the Super Bowl was coming Kokomo wanted some sort of visitor resource because people I guess were staying as far as Kokomo for the Super Bowl that's wild isn't that crazy 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 because I didn't know how to scope and no one 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 or I wasn't good at it or both and so then I was like wait if visit Kokomo wants an app like there's got to be thousands of other tourism destinations that are gonna get an app they're right now they're spending months physical visitor bureaus to hand out print brochures surely it makes sense to spend 10 20 grand a year on like a on a Trip Advisor competitor that's native to them and so that was bluebridge before we dive deep into blue Bridge yeah I want to learn you grew up in Columbia yeah how did you land in the States oh sure airplane um yes parents are fully Colombian been there for generations and one particular Sunday pretty much everybody in Columbia's Catholic so we used to go to you know his mass in the country club avocados every Sunday and I was building a tree house with my dad had just seen Swiss Family Robinson or whatever and I was like live on the land like wild have a tree house so my dad building it we had got Palm fronds for the roof it's just a legit Treehouse right and they you got to get them on the roof while they're green or else they'll crack and stuff in the way that waterproofs it is they got to dry in place we got the palm fronds they were drying I was like hey Dad can we skip mass 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 tree house the church was right across the street like diagonally across the street from us we were building a treehouse we heard gunshots pretty close by my prep my dad's pretty concerned I don't know the difference between a gunshot and a camera 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 and camouflaged clothing look 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 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 but ultimately what ended up happening is a gorilla group called The eln came into the church told everyone that they were the Army there was a bomb in the building that everyone needed to evacuate and kidnapped like over 120 people including children most of the children were let go that day they were 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 like most of them let go had friends from school and church family and stuff and most of the adults were gone for over a year just so much for ransom so people had to sell cars and houses and you can imagine as a kid not knowing if both of your parents are alive and 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 the Treehouse or not going to church or whatever saved from a lot more therapy later on it was not an easy situation but yeah I remember to breathe I like literally that's insane I don't 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 saw that having money as 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 so 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 uh 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 a relationship with money is probably one of them and then just a general like feeling not safe in the world like the world isn't you can have had to transcend this belief that like the world is chaotic and not evil but like dangerous and any safety is derived 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 going to take it away from you actively and that's a very different fundamental belief about the nature of the universe and the world than other World Views and there there comes that came with a gift of a ton of like self-reliance and resourcefulness and an 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 how were you when this happened and then when did you come to the states 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 Colombia All right so this is going to get way out there for a quick second but so I don't think I've like man so many emotions are going through me that's just one of the most amazing powerful things to even wrap my brain around that a friend went through that and 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 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 mean since I'm asking 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 sound it's all relative but exactly exactly but it's all relative I don't think a kid differentiates between a mass kidnapping in Colombia and getting bullied at school or whatever like it feels awful that it traumatizes that kind of a thing and all of us are like just doing our best walking around with like are beautiful parts of ourselves and also the parts our defense mechanisms and our childhood adaptive selves like were 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 in our growth and our potential and so 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 of empathy and of realizing that everybody has their story and we don't know what happened to somebody's earlier in the day so maybe treading kindly and carefully is a better path and I don't know bulldozing ahead that's what comes to mind but I don't have any of the 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 there's super power is coming from a place of some sort of initial trauma when I say superpower those things that you name resilience resourcefulness creativity and every Yin has its Yang which the dark side 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 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 and things that you learned along the way 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 because I remember when you came to the first powder cake event like you were still in college yeah oh yeah and you came it 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 hard thing that was likely to fail right how'd you hear about that first time I have no idea I have no clue sorry yeah great marketing great marketing from whoever was running it was just magic yeah exactly the way people found out about that in the early days is there was this new thing called Twitter and it was relatively early platform called YouTube and I was sitting in the corner of them flip cam yeah yeah taking a video of it I remember that Mark that you can find that 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 yeah I would put it on YouTube tweet out the link and people would be like where is and I remember are you saying that you drove an hour and a half down to be there this kid's gonna be okay yes yeah that's Hustle Man yeah it's yeah it's amazing to think back on that so 21 probably 21 years old he's a junior junior in college in the um Junior Summer I try to sell mobile apps for three months sold nothing I just yeah 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 going to be like an entrepreneur and but I just straight up failed and I didn't get a single customer the whole summer and I was like 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 good advice and well-meaning by dad for sure but we didn't end up doing that but yeah then early then November after I had to go 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 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 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 the congregation we did some for University Rec departments we did for Indy 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 got it to you know raise venture capital I learned how to be a CEO right to go from maker to manager to leader is a huge transition and what got you here won't get you there kind of realizations 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'd ended up with very at first we could do lowest common denominator functionality for all four and it worked and 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 road maps 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 was like too small just for mobile apps we'd have to go into CRM and other kind of verticalize so anyway ultimately decided that we were going to 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 because my board really wanted me to go up Market let's 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 and we couldn't really go up Market in tourism we had to visit South Africa and visit New Jersey we had states and countries as clients their tourism bureaus so if I was like if we're going to go up Market I we got to go corporate and we got to go for-profit versus these small non-profit clients and so we basically it was a bold move because we stopped selling those church and tourism and so our growth peaked and in six months our growth was going to start tanking because 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 looked like crap and we couldn't sell them and I had never sold the business before and I was also trying to get a third one off the new one off the ground um and so that was a really insane time where I just did not find balance it was very stress because of the weight of responsibility but I got the darn thing sold we got eight million bucks for the tourism and church units they each only have one million ish or so of AR and we sold no brand no employees just the customer contracts and a copy of the technology and so it was really great no Investment Banking help just did it myself those were two separate transactions very spread out from each other they were totally several transactions that closed within a day of each other with two different buyers 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 I don't want to hear about it just freaking go do your job and just get get out of my face and you have enough of those interactions and people start leaving and I feel like 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 I guess to what helps finally like things click yeah I think 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 visitor bureaus into churches because like I understood how our Lego functionality work and I was like this event calendar is the same for a sports team than it is for a church and 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 everybody it was just everyone's not a Founder in 90 hours a week yeah understanding the opportunity and how big the platform is in his 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 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 is seeing good ideas and we see them everywhere and we are very 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 a new idea but they know how to just like Peter teal just to monopolize the crap out of a specific segment and be the market leader in a saturated and dominated and then in a very careful programmatic testing way expand to adjacent market 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 in Risk you know what I'm talking about you just can't defend we all have that friends soldiers and you're defending eight countries what are you doing you're bleeding army man you're bleeding army men what are you doing yeah I think it's remembering that not projecting ourselves onto our teams and unto others and that people really Thrive with Focus can do incredible things with constraints number two to realize that what got us here is seeing opportunities isn't what gonna get us there that actually disciplined focused execution is what's going to 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 two percent you just have a leaky funnel or why would invest more into marketing 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 going to 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 in a Visionary in 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 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 if 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 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 bored 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 push back and can get that sort of supporting balance yeah oh that's such a that's such a narrow line that we walk between uh 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 300.

yeah exactly yeah and so that is just that's just hard I think just empathy wise is 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 the data and our team and psychological safety But to answer your specific question I think psychological safety is trust that's earned and so it's it's a thing 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 is 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 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 and 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 going to succeed but then it's also really not healthy when everyone's just disagreeing all the time 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 you know we had some co-op 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 comes back to communication yeah really I know that sounds absolutely a little bit easy and whatever but no no starting off with culture on day one and it seems like when inevitably somebody's going to come to you and say hey Santiam 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 but have you talked to them yet one-on-one and said hey I you said this is what I heard is that correct it seems that 90 of the time people are like oh that's not what I said yeah they might have said that but in their brains they didn't think they said that yeah great for your Intimate Relationships at home as well 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 right yeah that nothing what does that have to do with a mobile app platform for tourism and church viewers but every the horizontal thread of leadership and management is that we're all in the people business ultimately regardless of what our product is regardless of what our industry is we all whatever whoever I guess there's some Industries where chat GPT 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 is the thing that's very good research man quick break from our normal programming I have Erica schweire CEO from Elevate Ventures here in the studio today Erica thanks for being here yeah thanks for having me and you're going to 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 going to feature six Innovation Studios so think hard tech software Sports Tech Ag and food Healthcare and Entrepreneurship is going to kind of be our catch-all 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 it's going to be a multi-day thing that's multi-day in downtown 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 rallyinnovation.

com and sign up for communications they can also get their tickets I love it you heard it here at rallyinnovation. com we'll see you there research 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 to different cultures within one company yeah 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 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 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 during the same time I think part of what we realized is that as we pivoted from bluebridge 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 reset 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 a 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 going to be concerned my investors are going to 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 longer than it needed to be so it yeah for a while 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 things shift things happen opportunities come up Etc passions sometimes shift us out 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 or call them up and talk to them 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.

5 after I was a CEO 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 what book did you read what was the magic answer yeah like School of Hard Knocks you're 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 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 or oh you just did a perform you just gave your team like proactive feedback every six months like maybe I like come up with the criteria for your job and then every once in a while I'll tell you how you're doing instead of well I just I think I just picked it up I also I had Bill Godfrey on my board um Scott Dorsey for a bit Don aquilano John true from cultivation Capital just Ryan Ziegler for medicine really great people that kind of knew some of them listen so between I think between voraciously reading and then I got a coach 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 like 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 like a perfect leader all the time how did you find your coach Employee Engagement best practices a friend Scott Whitlock recommended chip 90 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 them 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 Enneagram then but he described what an Enneagram eight was like and he was he self-identifies as any M8 and I was like oh why do you know me so well I mean it's not that he knew me that well he just knew about my Enneagram 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 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 kind of an investment and so how do you until 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 it was really great so you just talked about like the ROI on an executive coach 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 that's value in one session 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 because they raised like family and friends if 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 ask them one question of they told me about 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 private product pivot and then obviously a bunch of objections came to mind and fears of what what do I tell investors and so you can make a plan for all those things but it sounds like you have Clarity and he was like yeah I have Clarity and they invested in the founder and they invested in the founder exactly and made the 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 you know get a different perspective and all of a sudden they don't quit what's the ROI of eventually that startup sells successfully because they stuck through it my coach helped me with that 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 just be like I'm gonna take care of my mental health good luck everyone investors and shareholders and customers I'm going to 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 and then ultimately exactly and it led to a good outcome and what were some of the other 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 conf self-confusion because 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 the U value is not in place right now is that what I'm hearing and oh yeah it 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 got really like down 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 real quick I want to if anybody's listening to this and you're if you're a Founder co-founder whatever because people you don't understand what the experience is like unless you walked it right and so getting a coach or finding the groups there's entrepreneurs organization out there there's also other in that group aren't you yeah and there's also I still meet once a month with a group of CEOs today yeah and so do I and even for what I don't even know how long 20 plus years probably and what's the benefit of having a peer group like that therapy yeah you're not alone you're not alone and so it's easy for us to think 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 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 in in the medium holy cow it provides so much more headspace for some kind of balance yeah it's just I think it's a prerequisite it's almost like investors shouldn't invest in companies at the CEO or the co-founders don't have some Outlet once a month I think mirroring back is one thing I think another question questions that expand the sense of possibility that they have to 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 I mean I'm raising venture capital for the first time and they go on and they're searching like how to read insult 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 whatever or the Holloway guide to fundraising so it's several things in once but it becomes this in it 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 of some of the way can be really easy and in those conversations what I've observed is when people share experiences that's where the magic happens right instead of trying to give advice yeah you're what they call it Gestalt yeah it's like really which is hard to do right it's so hard coaching that's a skill set of coaching it's just yeah I'm gonna go a little bit out of left field here because 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've always admired about you Santi beyond your servant leadership open-hearted leadership and just willingness to be vulnerable in that situation of being an entrepreneur being a CEO is also sharing what you're learning along the journey and 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 he got the message of the mission that we were after out there and then he 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 out of cash it's get the right peeps surrounding you and so I think it helped tremendously to create a really great employer brand where people wanted to come work because they had trust in the message they understood that they wanted to be part of that mission and they had leadership that they felt some sort of connection it's sometimes you 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 um speaking engagement the book really unlocked speaking engagements and those were if your target market goes to events they can be a really great go to market armed 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 we got every time that I speak we got customers it was hard to scale that type of thought leadership because it was in digital thought leadership it was get on a plane and speak at a thing and so when you're trying to grow 2x you can't just do two times the amount of speaking engagements every single year and so actually that was one of the things that 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 revenue that we almost didn't it didn't allow our team to develop more scalable ways of generated generating demand gen because we it was just double the like when we had a 15 close rate on sale on leads that came in anywhere else and we had 30 percent close rate on folks that heard Adam and I speak and so just 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 inbound marketing right it's what's the value of gaining Goodwill with the people early that are going to eventually make a buying decision so you have good will 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 want to 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 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 because that was going to be way easier than me trying to become a great writer which is just not going to happen it's great advice yeah so 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 customers 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 oversherry 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 of what is like a genius thought and what is just like a rote thought I don't know the difference you have brilliant ideas you wake up the next morning like that was done what was that so you posted on LinkedIn you're like this is for sure going viral I'm like yeah 12 people like it and you're like all right a good editor 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 it really is table Stakes if you want to be a leader 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 may not be authentic to everybody and it may not be necessary there might be people maybe everyone I guess could be your employees are online so on for an employer brand it's going to 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 goes back to good marketing which is like knowing your audience and where are they at and and people right goes back to people wanted to work with you and Adam while you were on stage like oh wow yeah they're captivating I want to 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 Copp was talking about this it's not B2B it's not like B to C it's just like business to human like people want to buy from humans and that's why all these videos are like shaky and stuff because it's like authenticity is important more than it is about produce edits and stuff like people want the realness because we're surrounded by so much fakery if we just want the real we're hungry for the real 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 and what you're doing oh sure yes so I'm coaching CEOs and Founders and it's executive and Leadership coaching so I meet with my clients twice a month and I get really good at understanding their goals and who they are and do a lot of intake what are their childhood of mechanisms and where 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 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 um and then just really reacting 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've 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 or 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 CEO who should I hire a CEO 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're really great at that really gives them energy and how do they 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 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 that's what I really 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 in my ARR growing faster and sure it did that but also gaining more self-awareness becoming a better listener 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 because 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 um 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 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 okay ready yeah outside of the amazing entrepreneurial ecosystem what is Indiana known for what is Indiana known for hospitality and kindness book of true tourism executive yes yes okay ready what is one Hidden Gem in Indiana the White River I think I like kayaking nor more north than here but yeah 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 of the crossing and kayak and float down to my backyard which I really love doing or 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 both to dinner and yeah it's like just a I love there's something about water that's calming there's something about flowing water that's really calming and it feels like you're like in Brown County with like really tall trees and water and there's all sorts of the bird songs or incredible so many birds and wildlife so it's this really Hidden Gem of unspoiled nature almost and in the heart of Indianapolis that's right 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 100 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 like on a river in a state park yeah it's so cool for sure it's really cool to kayak by your house and be able to pull over and grab a beer on a Saturday afternoon oh yeah a little Cabrio trip gentlemen there we go yeah all right final question 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 go with like Chip 90.

he does great work around leadership stuff he's done really great work around the anagram I really think that the Enneagram 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 your type and you know 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 I love that Santi thanks so much for coming here and sharing some of your journey super excited about this chapter for you working with 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 to keg to to elevate we received funding from Elevate at amplify and through some sort of vehicle um and so just thank you very much your work makes it easier for everyone else throwing 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 stories this has been get in a powder kick production in partnership with Elevate Ventures and we want to hear from you if you have suggestions for a guest or a 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 at powderkeg.

com newsletter and to apply for membership to the powder cake executive Community Check out powderkick. com premium we'll catch you next time and next week as we continue to help the world get in since you just listened to this podcast you might be thinking about starting one for your company lucky for you our partners over at casted have you covered cassid is the first and only podcast in video marketing platform made specifically for B2B Brands I love this about them the platform makes it possible to publish Syndicate amplify and measure the value of your podcast and video content in fact we use it for our podcast here at Powder Keg and if you're a startup you should listen up because cassid for startups is definitely for you they are offering exclusive deep discounts of up to 82 percent off retail price for qualifying startups connect with casted at casted. us slash powderkeg