Why Every Entrepreneur Needs to Embrace Failure | Brad Springer | S7 E5

Building a startup has never been easy—but today’s founders have one advantage previous generations didn’t: artificial intelligence.

In this episode of A Founder’s Life, Leo Gestetner sits down with Brad Springer, Co-Founder of Bob.pro, to discuss entrepreneurship, AI, startup growth, resilience, and how founders can leverage technology without losing the human side of business.

Brad shares his unconventional journey from working in hospitality and marketing at Chick-fil-A to teaching himself how to code by trading beer and dinner for programming lessons. That determination led him into the startup world, where he spent years building software companies before launching Bob.pro to help businesses thoughtfully adopt AI.

But this conversation goes far beyond technology.

Brad opens up about how adopting his son transformed his outlook on life, why every entrepreneur needs intentional family rhythms, and how learning to slow down has become one of his greatest leadership challenges.

Throughout the conversation, we explore entrepreneurship, business leadership, artificial intelligence, resilience, family, health, startup growth, and the mindset required to thrive through every season of business.

Whether you’re building your first startup or leading a growing company, Brad shares practical lessons every entrepreneur can apply.

In this episode you’ll learn:

• Why failing fast accelerates entrepreneurial success
• How AI helps businesses scale without replacing people
• Why intentional family rhythms matter during busy seasons
• The importance of slowing down to become a better leader
• How prayer, meditation, and reading create mental clarity
• Why quarterly fitness goals keep entrepreneurs motivated
• How vulnerability builds stronger teams
• Why commitment is essential when building a startup
• How every season of entrepreneurship requires different priorities

Brad also shares why adopting his son became the defining moment of his life, how teaching himself to code changed his career forever, and why his personal mantra “burn the ships” continues to guide every major decision he makes.

If you enjoy conversations about entrepreneurship, founder mindset, artificial intelligence, startup growth, business leadership, resilience, personal development, and building meaningful businesses, you’ll enjoy this episode.

This episode of A Founder’s Life is brought to you by Thankz, helping founders scale with reliable remote talent.

Email founders@thankz.com with the subject A Founder’s Life for preferred pricing.

Connect with Today’s Guest – Brad Springer
Website: https://bob.pro
LinkedIn: https://www.linkedin.com/in/bradspringer/

LinkedIn

linkedin.com/in/leogestetner

Website

leogestetner.com/leo

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Transcript

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I have trouble slowing down. and often the inability to slow down means sometimes you lose focus on the right things and In growing businesses, sometimes you have to face those things head on and everything is a season, you know, there's hard seasons, there's easy seasons. but sometimes it's like, hey, we're gonna be grinding out for the next few months and we have to go into it as a family and know that like, hey, we're you know, I might have to find work time when people are sleeping, and that's okay. but we have to call out what's important and then keep those things top of mind, whether that's a date night with my wife, whether that's making sure that I'm present with my son you know, when he's home from school or home from camp or whatever. just creating that space and allowing yourself the time to do that. giving yourself a little bit of grace, right? Welcome to a Founder's Life. I'm your host, Leo Gastetna. On this show, we dive into the real stories behind the highs and lows of entrepreneurship and how we pursue a more integrated and meaningful life along the way. This podcast is sponsored by Thanks, helping founders like us scale with reliable remote talent. Now I'm excited today to be joined by Brad Springer. Brad, thank you for joining us. Would you like to kick things off by introducing yourself? Yeah, absolutely. thanks for having me. my name's Brad Springer. I'm out of Raleigh, North Carolina. And you know, I have a a pretty interesting journey that started in hospitality and then found my way into software and never looked back and now currently working in AI implementation for small to medium sized businesses across North America. Well, talk to us little bit about the journey that brought you to where you are today, and then talk a little more about your business, what you're doing for your clients, what you're doing with AI, Yeah, so I I definitely didn't have a we'll say a normal journey to to sales and and software, to be honest. I started out of college, had no idea what I wanted to do. I actually worked in a lumber yard for a while, driving a forklift, just figuring it out. and spent some time in the hospitality industry, working for camping and then spent About four years working in marketing with Chick-fil-A. And throughout that time, one thing that I always loved was the experience of customers. how do we make just an incredible experience for someone who is walking into a restaurant or walking into a camp or you know, just having a lunch meeting So 2012, as I was kind of considering my next steps with Chick-fil-A, the market turned and things slowed down greatly. So I kinda had this moment where the world delivered me a choice of kind of like, hey, like what do you want to do next? Like where do you wanna go? And I wasn't sure. And I was really interested in technology. I have always been. And I had a friend who had talked about a startup he had been a part of and just kinda it resonated with me. The journey I always kind of call that if you have drive and if you have a desire and a passion, like there's nothing between you and making it happen. So I funny enough, this is you know, about 2012, probably October. I didn't know how to code to save my life. So I found a neighbor down the street who worked at IBM and I made a deal with him that every Wednesday for two hours I would bring him whether twelve pack of beer, bojangles, dinner, whatever, and we would spend time learning how to code. And I learned how to do basic coding. I learned you know, how to run cron jobs and just how to be enough to get my foot in the door somewhere. And after about three months of working with him to learn how to be useful in a startup environment, I got an interview and I kinda I always joke with my old boss, I kinda Kool Aid manned my way in and was just like, I'm not gonna take no for an answer. I remember looking at them and saying, Hey, I don't care if you pay me. I would like you to pay me, but like I want to be a part of this. And that's how I got into startups and that's how I got into software and the rest is you know, the rest is history. I got in, learned about all of it, and then just every day was something new. stayed with that company for six years, through a few acquisitions and still connected with those folks. It was a it was a wild ride. And talk to us little bit more about Bob. Yeah, so Bob Dot Pro is an AI services company. So our goal is to help small to medium-sized businesses transform with AI. so how do you actually implement AI in your business to help with operational drag, to help scale your company without hiring a bunch more people? and how do you do it thoughtfully? So we work with businesses from healthcare to industry or industrial, you know, just all kinds of different businesses. But we come in and look of what's going on, how do we help and assist you to use AI so we can remove workflows and things that people honestly don't really want to be doing to help kind of bring them what we say above the line to do the things that people are best at. making decisions, judgment, relationships. and it's been really awesome. I mean the customers we work with are customers who are looking to scale and looking to care for their people and do that with AI. So it's been really neat to be able to come alongside and create new types of experiences and customer care. while companies are being able to scale and grow more revenue without hiring more people. And then when that happens, you can take care of the people you have all the more. so it's been really fun to do that. Great. What kind of size are your customers for that Yeah, so we focus right now anywhere from, you know, ten employees up to two hundred employees is kind of our focus, specifically from employee range. And then we have some companies that are doing, a couple million dollars in revenue up to about a hundred and fifty to two hundred million in revenue. Perfect size for needing that 'cause they haven't got their own internal resource. this is an area of business that not a lot of people are focusing on. There's a lot of competition for the enterprise eyeballs, but this is an incredible market of businesses that are interested but aren't sure how to go about it. So finding a trusted partner to who's actually interested in your outcomes and ties their success to your outcomes it's been a really neat way to open up. conversations and doors to talk with people about it. quick request to the audience, if you're enjoying these conversations, please click subscribe. And Brad, talk to us a little bit about what family looks like for you. Yeah, so my family, so I have a wife, a son, and a black lab. So my wife and I have been married for about twenty years. we have twenty-one coming up this year. she is a very patient and and loyal person because she's put up with decades of me and in startups and you know, kind of this world of adventure when it comes to starting new businesses. and then I have a nine year old son who loves soccer, who is just all about it. He's wide open. and then he actually, which is part of my story later, but he he actually is adopted, which impacted my wife and me a ton. and impacted my work and everything when we went through that kind of journey together. and then we have a black lab named Molly who's four, who keeps us all on our toes. So the timing question based on when we're actually recording the podcast is who's your son supporting? goodness. You know, at nine often it's who's winning. but he is pulling for England right now pretty hard. so he's a big Premier League fan and he loves Liverpool. so he is pulling for the Lions pretty hard. Perfect, that's good to hear. We need all the support we can get, you know, in the semis, hopefully make it to the finals and and the winning. And what does the health look like for you? And and for health, you know, that can be sleep, nutrition, fitness, mental health, physical health, however you look at it. So one of the things I struggle with is slowing down. So I have always been kind of a go go go type person and probably over the last fifteen years, even more specifically probably the last decade, when I think about health, it's kind of creating space to slow down a little bit and allow yourself to breathe. whether that's physically, mentally spiritually, emotionally, what that looks like. I've had to kind of create space to do that and create space to exercise, space to read, journal. and I generally do that early in the morning or late at night. but what that looks like for me specifically is, you know, I'll throw this thing called Pies that kind of grounds me and it And it's something I go through most days. And it just stands for how are you doing physically, how are you doing intellectually, emotionally, and spiritually. And so it's just an easy way for me to kind of stay grounded throughout the day, throughout the week. because those are kind of four areas. If you if you're doing okay, or at least you're cognizant of those four areas, you're thinking right. or at least you're thinking about the right things. So I generally do that because it's a repeatable thing. That's easy to top of mind. you know, it doesn't take much time to just say, hey, how are you doing in those four ways? I spend a lot of time reading for pleasure, for business, but usually about 15 to 30 minutes a day, I'll read. and that's how I close out my day because that will just allow your mind to wander and just kind of take a break. and I start most days with prayer and meditation. Just to kind of be quiet and calm the mind before you jump into the day. And then physically, I kind of do two things. One, I try to exercise a few days a week. And whether that means just going on a walk, I had back surgery in March. So exercise for me right now looks a little different than it used to. but I'm working my way back in. But for now, it's just creating space to go on a walk. without technology and and just walk and look around and listen. but once I'm back at it, I generally do a challenge a quarter. So that might be a marathon, that might be a long bike ride. I like to ruck a lot. So walking with weighted backpack. but usually I'll do some sort of, hey, I want to go canoe this far, I want to run this far, and I'll set something a quarter. And then that dictates my exercise regime for that time. And I'm always looking towards like, all right, it's coming. Like I gotta ruck a marathon or I gotta do this race. and it keeps it kind of interesting and fresh to where it's not like, well, I just run all the time. It's like, no, I'm training for this thing, whether it's camping or a hike or whatever. It just kinda keeps it keeps me motivated. Like that. So that's a nice one, a quarterly goal. And what do you like to do for fun, apart from running and hiking with backpacks and things like that? Yeah, so I'm definitely a tinker. So I love to tinker in the garage. Like you know, years ago spending so much time in software and you know building things that are software you don't do a lot with your hands sometimes. So I decided one day, probably fifteen years ago, that I was gonna learn how to do leather work. So I like Decided to make a wallet and then make a bag. And then it turned into just kind of off and on tinkering of like it was fun to go out and make something or make a gift for someone. But you had to kind of slow down, pay attention to detail, you know, put some music on. But stuff like that, like I love just getting out there. but outside of stuff like that where it's just tinkering, you know, master of Jack of all trades, master of none when it comes to tinkering, that's me. but spend a lot of time outside hiking. I love to bike. you know, anything that kind of gets you just disconnected for a little bit. My family and I love to go fishing. we love spending time on the water when we can. And we play a lot of soccer, as I mentioned with my son. So there's a lot of fierce competition in the backyard with a nine year old who is now better than his mother and father. So just play, you know, like at the end of the day, we just play a lot. And I think that's important. you know, one of the co-founders I work with now always talks about how we're grown up kids sometimes, right? And you have to remember that like playing is still really important. It just looks a little different. So as a family we spend a lot of time just playing together and and that generally leads to A deeper connection just to go out and play and be present with each other. I I love that. I think that's a hundred percent right as a way to connect as a family. And how does a sort of integrated life look for you across those four different areas? Yeah. So I would say 'cause my wife, you know, she has a pretty demanding job as well. so we are definitely kind of moving and grooving at the same time together. And so what that looks like is we kinda have a I'll call it a family operating system. there's a reality there that when we're all running hard as a family, if we don't kinda have a true north to kind of come back to, things can get kind of messy real quick. So we kinda have a operating system as a family where we, you know, my wife and I, we have to keep a calendar, we have to little family rhythms in place to make sure that we're having our family dinners and our date night together But often outside of just pure communication and making sure we're talking to each other, it looks like understanding the priorities of family and the priorities of work and then putting them in the right spot. and I think sometimes, you know, I mentioned earlier I have trouble slowing down. and often the inability to slow down means sometimes you lose focus on the right things and In growing businesses, sometimes you have to face those things head on and everything is a season, you know, there's hard seasons, there's easy seasons. but sometimes it's like, hey, we're gonna be grinding out for the next few months and we have to go into it as a family and know that like, hey, we're you know, I might have to find work time when people are sleeping, and that's okay. but we have to call out what's important and then keep those things top of mind, whether that's a date night with my wife, whether that's making sure that I'm present with my son you know, when he's home from school or home from camp or whatever. just creating that space and allowing yourself the time to do that. giving yourself a little bit of grace, right? Like it's okay. Like we're we're all gonna we're gonna fail together, we're gonna win together.~ but just give yourself a little, a little bit of grace to to have time with your family. work will always be there. it will It will always be there waiting and asking for more. So if you don't call that truth out, you get in trouble often and I've learned that from plenty of experience.~ I think that's also true. And what has been a pivotal moment in your life? probably the adoption of my son is outside of, you know, getting married. you know, that that was pretty pivotal moment when we got married. But, you know, my wife and I, like and we're super open about this, but you know, we we were unable to have kids. and that's a pretty intense thing to go through when you you never think about that growing up or when you get married, it's just like, you do the thing. So, you know, we were in our 30s and we're like, hey, let's have a family. And that didn't happen, right? So we both were like, well, let's adopt. Like that'd be fantastic. but to get to that point, you know, when you go through something like that, I always tell people you kinda have two paths with your partners. Like you you can't do that, you're gonna drive away or together. Like that was my experience. I won't say there's only two paths, but my experience was like we were gonna come together in this and fight through it, or like it was going to drive us apart. And you know, we chose to kind of lean in together and lean into the journey and the pain. And and at the end we came away with our son. And it was incredible. And like I would go through it a thousand times because I know it's on the other side. but that That moment was super impactful for me because that's, you know, often when I think about work, if I believe in the mission or the product and I believe in the people and they believe in me and and we're doing these things together, like and you lean in together, like you can do a lot of really cool stuff. and my wife and I were able to get through this together and we came out closer than we've ever been. but I think that's very true in work as well. Like Startups are hard, right? Like, you know, like there's no magic button, right? Like it's a grind and it's hard. And it's, you know, you gotta do the things over and over and over. but if you're doing it with people that you trust and you're doing it with people who you want to be doing it with, you can accomplish some pretty cool stuff, but you have to make that decision. You have to say, I'm going to do this with you and I got your back and you got my back and Are gonna be mad at each other sometime? Sure. Or are we gonna celebrate together? Absolutely. but when you make that decision and kind of burn the ships, there's no going back. And I I just think that part of our life, like burn the ships is a major mantra in my life. It's just like if you're going after something, like don't don't leave yourself a way to get out. Like commit and go. so yeah, that was that was a that was a pivotal part of my life that impacted me personally and In business. yeah, and there's definitely nothing easy about being an entrepreneur, that that's for sure. And what's one piece of advice you'd give from a sparring entrepreneur? man. You know, I'm just gonna say the first thing that came to my mind is just fail fast. don't be afraid to like lean in and fail. and in the world we live in today and the technology that has become available to us, especially in the last like eight months, you can fail faster than you've ever been able to before in a good way. Right. Like the speed to failure is much faster. And that means the speed to information and the speed to knowledge is like it's faster than it's ever been. And the ability to do that means the ability to iterate and change quickly. And that is a gift that the current kind of technology stack has given us that, you know, 10 years ago, you know, failing's always painful, right? But the speed in which you can fail and the speed in which you can learn in a startup was already really fast. But now with the new technology that's available to us, especially in this kind of newest season with AI, like you can do it even faster and it's okay. And again, give yourself grace. Like it's okay to try something, be smart about it, act with data, take calculated risks, but like jump in. That's that's absolutely perfect advice. And ~ how can people find you? Yeah, so two ways. You can find me on LinkedIn ~ and you can find me at Bob dot pro. so we're, you know, on LinkedIn you can I'd love to connect with you there. And then Bob dot pro, you can go there and literally talk to one of our bobs and all about what AI transformation looks like I have one other piece of advice that just it it's worth noting because I tell myself every day. And I think this one's lost often, but it's okay to be vulnerable. you know, when you go into work with people, it's it's okay to be vulnerable with your other business partners and let them in on ways to win together. Because we often I think it's so common to go at it alone mentally. And I don't think that's where I don't think that's how we were made to be. And I find that when I am open and honest with the people I'm trying to build business with, and they're open and honest with me, our ability to love and care for each other and go win, compete and win together exponentially goes through the roof. but I don't think that's I think it's it's a learned behavior. I don't think it comes natural, unfortunately, for most people. It was a learned behavior for me. So, anyways, I want to mention that because I think it's important. Ocular Advice and thank you for joining us today. Absolutely, thank you. And thank you everyone for listening.