A Founder's Life
Join me as I explore the powerful intersection of entrepreneurship, health & wellness, and parenthood. In each episode, I’ll be interviewing inspiring individuals who excel in one or more of these areas, sharing their stories, insights, and lessons. My goal is to provide valuable takeaways that can help you thrive both personally and professionally.
A Founder's Life
The Army Lesson That Built My Career - Darren Lauda - S6 - E3
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👤 Connect with Today’s Guest – Darren Lauda
LinkedIn: Darren Lauda
Email: daren@outsetops.com
Website: https://www.outsetops.com
In this episode, Darren Lauda shares his unconventional path from joining the U.S. Army after high school to building a successful career in enterprise software and launching his AI forecasting company, Outset.
Darren opens up about the early years of his career in software sales, working his way from receptionist to executive leadership at major technology companies. He also shares a deeply personal moment when a voicemail from his young son forced him to reevaluate his priorities and completely rethink how he approached work, health, and family.
We discuss entrepreneurship, leadership, fitness, discipline, and why founders must learn to fail fast and iterate quickly.
What you’ll learn:
• Why entrepreneurship always takes longer than expected
• The dangers of putting career ahead of family
• How Darren rebuilt his health and fitness after years of neglect
• Why forecasting is critical for scaling companies
• The mindset founders need to move quickly and learn from failure
⏱️ CHAPTERS
0:00 – From Army Service to Software Sales
1:05 – Building a Career in Enterprise Software
4:28 – The Voicemail That Changed His Priorities
8:05 – Health, Fitness & Personal Discipline
14:58 – Advice for Entrepreneurs: Fail Fast
Website
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Welcome to a founder's life. I'm your host, Leo Gastetner. On this show, we dive into the real stories behind the highs and lows of entrepreneurship and how we pursue a more balanced 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 Darren Lauda. Darren, thanks for joining. Would you like to kick things off by introducing yourself to the audience? Sure.
SPEAKER_01First of all, thanks for having me, Leo. Great to be here. Really enjoy the show. My name is Darren. I'm based in Southern California. I am a husband and a father, first and foremost, which is how I like to think about myself. Next, I'm the CEO of a company called Outset. We are an AI-based forecasting tool, a SaaS software platform that's used for people who want to build long-term predictable forecasts they can bet their business against.
SPEAKER_00Excellent. So what I'd like to talk about next is talk about a little bit about your journey. So what got you to where you are today? You actually gave a pretty good description of the current company, but talk a little bit more about that one as well. So it's really trying to understand your journey.
SPEAKER_01Sure, absolutely. I'll go way back in time and I promise not to belabor it. But when I was a young boy in the Midwest, my father bought me a computer. It was a TRS 80, and he put me into programming classes, which I thought was kind of crazy at the time, but I learned a lot about computing along the way. Also learned eventually that I did not want to be a programmer, but software was kind of core to who I was. My father was a university dean, so I did what a lot of teenagers do to rebel against a university dean, which was I didn't take grades nine through twelve very seriously. So when I graduated high school, I had a couple of choices go get a job hourly somewhere or join the military. So I joined the army, spent a couple years in what was West Germany at the time, upstate New York, down in Central America, really enjoyed my time there and grew. And when I got out of the army, I said I'm going back to software, but I had no degree. At that point in time, I said, Darren, you need to be a security guard. And I said, that can't be my path. So I found a local small software company and convinced them to let me be their receptionist. And that's how I got into my first software company and started working full-time during the day and going to school at night. I would eventually get my bachelor's degree and my master's degree. And very quickly, I taught myself this particular software product so well they said, hey, Darren, get out in the field and go sell it. And so that started my career in software sales. I grew through small companies and large. So I've been through companies that were sub-five million dollars in rubbing when I started. And I've been at very large entities like Salesforce.com and PTC. So I've seen how things work when there's not much resource and when there's tremendous resource. Along the way, I married the love of my life. We had our first aid about 30 years ago. We have two great kids. My son is a wild end firefighter in Phoenix, Arizona. My daughter is a senior at Clemson University, and I'm now leading the founder journey, which I'm really excited about. That's Outset. The idea behind Outset is I think people sometimes get their planning exercise wrong at the outset. And that's because they don't know their long-term booking forecast well. We wanted to bring those two things together and use AI to A, build a 12 plus month bookings forecast the business could believe in, and then B, allow the business to model potential sales and marketing spend to close future gaps. So if I'm sitting in January, I want to know that I have a gap to goal looming in July or August, and I want to try to fill that now with efficient marketing spend. Because if I try to solve the problem in May or June, it's going to cost a lot.
SPEAKER_00Well, you know, it's funny. We used to have a CFO who worked for us, and I'll never forget this, I don't know, 15, 20 years ago. But he always likes to say, you know, month ends and year ends that made up by account and think, oh, I've seen nothing to do with the business. So we always had sort of rolling forecasts, which always made sense, I thought. And and I don't know why that's not done more, but probably with tools like yours that's a lot easier.
SPEAKER_01Every month and close, that CFO and the FPA team are trying to bet what the next 12 months are going to look like. So they know how to allocate resource, right? That forecast is super important. It's usually outside the purview of the CRO or the chief sales leader, whoever that might be, but I think the two need to come together. I think that's the optimal way to run the business. Makes a lot of sense.
SPEAKER_00And you talked to us during your introduction quite a lot about family, but anything else you'd like to share on sort of how family looks for you, how it means?
SPEAKER_01Yeah, sure. Um, you know, I write about this sometimes on LinkedIn. Early in my career, I thought to be an executive and a professional, I had to put that first. So I missed ski trips. I missed entire vacations with my family. I missed my wife's presidents club so I could go on business trips and do career things. And I am incredibly lucky that they gave me grace and forgiveness for that. And it took a moment, my son was probably five years old or six years old. And I still believe my wife put him up to this, though she says she did not. I was in Melbourne, Australia, and I picked up a voicemail for my son who was crying. And it said, Dad, I had to look at your picture to remember what you look like. And I had this moment where I thought, I am destroying my family for all the wrong reasons. I have to make a change. I also looked in the mirror and I was about 305 pounds at that point. So I was traveling, I was eating, I was whining and dining, I was ignoring my family. Did my bank account look pretty good at the time? Sure. Everything else was a mess. So on that flight home, I made a very real decision to change. Family was going to be first. Health was important to family, I had to fix that as well. I called my boss and said it's time to make a change. I have to go off the road. At least I can't be on the road 85% anymore. I've got to be home. I've got to be present. It's the most important thing in my life. So true.
SPEAKER_00I think being a uh nothing like being a present father. Losing that weight. Losing that weight allows you to be a present father for that much longer as well. Absolutely. Well, moving on to that, I think uh talk a little bit about your health journey and how health looks these days, whether that be fitness, diet, nutrition, sleep.
SPEAKER_01My fitness journey had a lot of fits and starts along the way. Um I would look in the mirror, didn't like what I'd see. So I'd do something really drastic for three months. And I was famous for losing 30 pounds and then gaining back 40. So, you know, if you do that three or four times, you're plus 30 or 40 pounds overall. When I was 38, it was when I really dug in my first time and said I've got to make a life change. And so I announced to all my friends and family that I would fight a public kickboxing match um at age 40. And I hired a kickboxing coach and a trainer, and I trained like the Dickens. And basically what I learned is I could get very fit, and I was good at getting hit a lot. I was not the best kickboxer, but I was good at getting punched. And that helped really get me going in a positive direction. It went through it. The public fight got canceled at the last minute, um, so that never happened. But I had a few exhibitions that were really introductions to pain is the best way I can describe it. So, you know, when I rolled off the kickboxing, uh uh kickboxing, I went back to some bad habits, which is unfortunate. Finally, I came back around and I created a very simple formula that I could live with. And I said, I'm gonna eat uh clean 80% of the time. About 80% of my meals are prepped. They're very consistent, I know what I'm getting, they're a higher protein, that works for me. 20%, I do whatever I want. If I want to go out on a Friday night and have a giant charcuterie board and three glasses of wine and um a lasagna or whatever, I don't feel guilty about it because I've earned it with the work during the rest of the week. Number two, I reset my calendar for exercise. I block on my calendar Monday through Friday, 4 p.m. to 5 30 p.m. for exercise. Five days in a row. Now, on a day like today, I was on the phone at 6 30 a.m. local time with London. So by four, I'm ready to take a break anyway. It doesn't impact my schedule. And I know I'll probably lose one or two of those workouts Monday through Friday to something work-related. Travel, an important meeting, uh, maybe something that my wife needs, an event. So I can pick up the other two on Saturday and Sunday. So I'm almost always get five. Um, and I make that a priority. I do a mix of heavy weights. Uh for a very long time, I would not admit what my body was. I wanted to be a five foot ten, 185 pound, lean, low body fat, runner type, surfer type. I happen to be six foot three, barrel chested. And when I was in the army in Honduras for six months with no fast food, my lowest weight was 218 pounds. I'm just a big individual. Um, and so I had to learn how to embrace that. So I lift heavy weights. And for my cardio, I do what I call long cardio. And it could be on a treadmill with a 15 degree incline for 30 minutes wearing a 40 uh pound weighted vest. On a Saturday morning when I'm not lifting, I'll go into the canyon behind our house and I know how much you run, so you would not call it a run. I call it a run. I jog the flats, I speed walk the uphills, and I run the downs in the canyon behind our house. And that can give me a good hour to hour and 20 minutes of cardio. So by by by devoting the time, by um really getting systematic about my eating, that's been super helpful. And then, you know, candidly, I paid a lot more attention to uh blood work. I get my blood drawn every six months, deep panels, I'm looking at hormonal balance, I'm looking at all sorts of things, not just cholesterol, trying to figure out what the chemical composition of my body is, making sure I'm keeping that in a good shape.
SPEAKER_00Well, makes a lot of sense and remarkably similar to sort of all the way I look at things. So I think that's great. I think yeah, blood test the blood panels are really important. I think it's you know, I often say if it doesn't get scheduled, it doesn't get done. Yes. So I think if you don't block that time out, I might calendly will quite happily grab every moment I have free. So yes, for me I block out more time in the morning because um I I get up very early and I'm just tired in the afternoons and I don't perform as well, so I try to work out early. I used to do actually afternoons because I used to do uh when my son was still at home, he's at college now, 4 30 to 8 o'clock every day I was uh with him. At least six days a week. We would weightlift or box and then watch TV, have some dinner together. So yeah, I loved that. And I yeah, that was sacrilegious. Between the working out and it being with my son, that was not getting touched. But yeah, you know, it's it's important to find whatever works for us, whether that be, you know, half an hour walk a number of times a week, uh, you know, hour, 10-minute run, or a three-hour run. It's it's you know, and the weights uh again, there's been so so many studies showing how important that is as we get older. It really is.
SPEAKER_01And you know, I'm watching my father, I'm I'm blessed. My father is eighty-eight years old, he lives near me, um, and he was a marathon runner. That was what he loved to do. Not highly competitive, he was a university dean, but he runs several marathons a year. And in hindsight, you know, for him, he was always worried about getting fat, and that was what he would say. So breakfast might be an apple, lunch might be a granola bar, dinner would be pretty light and healthy too. And so what I learned over time, just watching him now is he had a fit heart, but didn't put a lot of muscle on his frame. And so as he aged, and I'm not saying you have to have a lot of muscle, but he didn't put enough muscle is a better way to say it. So as he's aged, when he tries to use as a walker, he hunches because his shoulders were never strong enough to hold him upright when he got to that point. When he fell and broke a hip, the rehab was much harder because he didn't have a lot of muscle around the hip. So when I say I lift a lot of weights now, it's less about trying to look like a bodybuilder and more about making sure that I have really strong muscle around my shoulders, my hips, my knees. So when something goes wrong, I can rehab and I can do better as I age. And it also gives you bone strength as well. Yes, absolutely. Absolutely. And I did at first do my workouts in the morning like you, but I learned in an odd kind of way, my brain works best between 6 a.m. and 4 p.m. for whatever reason. That's when I'm at my most aware and acute, and it probably starts to fall at about three. Don't know why that is. So I tell people schedule the important meetings early in the after uh earlier in the day, and that way at four I can go into our garage gym, which is on the other side of this wall, play loud music and lift weights, and I don't have to uh use my brain power as much. I can just focus on the lifting. Perfect. And apart from lifting weights, what do you like to do for fun? I love to do I love to travel, I love to spend time with friends and family. I love to cook, and that's something I really enjoy. Uh I love movies, I like to read. I don't know that it's the most exciting hobbies in the world. Um, one of the things I do enjoy doing is long-range shooting. I'm not a hunter, but if I can go to a long range and and see a steel target at a thousand yards and think about wind and elevation, humidity, and just hear the tink, if I'm able to, you know, make contact, I enjoy that as well. And my son enjoys that, so it's something we can do together. Lastly, I'd say my daughter goes to Clemson University. I become a huge Clemson athletic fan, athletics fans, and we go to several football games a year, American football, that is. Um and I've lucked out to be on the sidelines a few times. So go Tigers, big Clemson fan.
SPEAKER_00And you know, if you look at all of these things that you're doing, so you how does balance look? That sort of center balance across, you know, work and family and health and fun.
SPEAKER_01Yeah, boy, balance is something I chased for a long time. Actually, I didn't chase it now that I think about it. For a long time, I did too much work. But when I shifted, I kept trying to find it. For me, balance means um I've got to be really happy at work. Look, Monday through Friday, I'm gonna spend more waking hours with my employees and customers than I do my family. So I have to enjoy that. It has to be challenging and rewarding. I have to have fun and be able to laugh at work. I want to be able to come home and have dinner with my wife every night. My kids are out of the house. So if I'm not on the road, I want to come home and have a nice dinner with my wife and great conversation, and I want to laugh with her, and that's important to me. Making time for family and friends on the weekends is great. I used to work a lot on the weekends. Now I limit that. I will do two or three hours on Saturday or Sunday, not both, but that way I don't feel like I'm falling behind. I make time for my children. I go see my son in Arizona, I go see my daughter at Clemson. Um, that's part of finding balance. And making sure that I have, you know, time just for me periodically. It may sound silly, but it was sunny here uh over the past weekend. So I went and grabbed a fiction novel and sat in the backyard and just read my book in the sun for two hours and didn't think about work or anything else, that's part of finding balance. I don't know if that's a very specific formula, but it works for me. And I think I also had to resolve to um who I am. I talked about this with my size and my frame. When I think about my identity, it starts with husband and father, which I uh mentioned at the beginning of the call. The next part of my identity is big and strong. So kind of admitting what my body is, what my frame is. I'm I'm gonna be 225 or 230 pounds. I've got to be fit and low body fat and do it that way. Um professional comes after that. Husband, father, big, strong, then the work stuff. That's how I put the balance in my life. Nice.
SPEAKER_00I think I I I do it as father, athlete, entrepreneur on the old mode line, I think is uh what what what do I have very similar. Husband would have been up there after 28 years. I'm not uh I'm divorced. So that one's not up there anymore. I was there for 28 years. Yeah, I think I had a good run at it. All good.
SPEAKER_01There you go.
SPEAKER_00Uh what for you has been a pivotal moment in your life?
SPEAKER_01Wow. You know, it's funny that you ask that. I just had a flashback to it. It was when I was in the army, and it's funny because I just went and found the drill sergeant that gave me that moment, you know, 30 some odd years later, and reached out to him and we had a conversation. I was in the army, infantry, basic training, on my way to airborne school. Um, and I went to speak to the drill sergeant. And I, you know, in the if you've been in the military, they have office hours, 8 p.m. at night, and I knocked on the door and I entered. And long story short, I said, drill sergeant, do I have what it takes? And he looked me in the eye and said, apparently not, quit. Give up, throw in the towel. I'm not here to carry you. Nobody in this army is here to carry you. If you don't have what it takes, get out. And it was the first time an adult had ever spoken to me that absolutely plainly and directly. And I remember thinking, you're damn right I have what it takes. It was like a switch flipped. And I walked out of that room standing taller, wanted to fight harder, and I wanted to do more. So 30 some odd years later, I went back and found that drill sergeant. I thanked him for the inflection point he had in my life. I couldn't stop calling him drill sergeant, despite his repeated attempts to have me call him Bob now. But it was just such a formative moment. Um, it really stuck out. I've never forgotten it. Uh, what's one piece of advice you would give to an aspiring entrepreneur? Um, I don't know if it's advice. Number one, uh, it's gonna be harder than you think. Number two, if you think it's gonna take six months, plan for two years, right? It's gonna be harder than you think, it's going to take longer. If you're pleasantly surprised, fantastic. Number three, get out and get in front of potential buyers and spend all your time there. There can be an urge to perfect the product. There can be an urge to perfect the messaging. You can stay in your own room, in your own office, and try to perfect everything before you start. As soon as you're close enough, go. I heard a fascinating story about somebody who designed their user interface on their software product with a pencil, a notepad, and five potential prospects. He didn't have mocks, he didn't use Figma, he just went out and drew it. Would this work? No. Okay, how about this? No. How about this? We're getting close. Great. That was the starting point. Figure out how to move fast. You're your own worst enemy if you stay inside the four walls and don't get out talking to the people who might. Great advice.
SPEAKER_00I remember reading, it must have been 10 odd years ago, the book from uh Google CEO. And he's like, just launch quickly and iterate. Yes. This doesn't need to be perfect. And that's always stuck with me. And I used to have a business partner in a previous business where he wanted things to be perfect. And I was like, you know, you understand that the 90% is probably what any customer's expecting anyway. The extra 10% you want, no one but you is going to notice, and it's 50% of the work.
SPEAKER_01Yes, yes. And on that journey, when you're doing all this, I really um instilled into my brain uh to people I work with, celebrate the failure. It's a really hard notion to get behind. Every failure is a learning moment. And if you acknowledge it, you see it. Hey, we tried this and it didn't work. High five. Let's have a cocktail or an ice meal. What are we gonna do differently tomorrow? Right? It's when you let the failure continue and you don't adjust, you've got a problem. So when it doesn't work, fail fast, celebrate that failure, adjust and move on. So true. Tough thing to end on. And uh how can people find you? Pretty easy. I'm on LinkedIn, Darren D A R E N Lauda L A U D A. It's probably right there on the screen. You can get me at Darren at outsetops.com, outset like from the outset ops.com. Love to always talk about forecasting, life, health, whatever folks want to talk about, please reach out. Well, thank you for joining us today.
SPEAKER_00Thank you for having me. Really enjoyed it. And thank you for listening to today's episode. If you enjoyed the conversation, don't forget to subscribe to the channel, tell your friends, and please leave a review.