NM Live: Leadership Lessons from the Navy and What We’ve Learned Along the Way

Drew Sanocki

Hey everybody. Welcome to the nerd marketing podcast. We recorded this one on Memorial day. So we talk about the top lessons I learned in the U S Navy that applied to my work today as an entrepreneur. And we talk about our life's regrets. you know, as a 53 year old entrepreneur married with kids, like, what am I regretting right now in my life? Mike talks about the same thing. It's a, get real on this one, you know, some tears, some tears are shed. So I hope you enjoy it. It's a good feel good podcast coming at you right now. 

Drew Sanocki

Happy Memorial Day.

Michael Epstein

Yeah, happy Memorial Day, Drew. Thank you for your service.

Drew Sanocki

I never know what to say when people say that. You're welcome.

Michael Epstein

Yeah. For those of you who didn't know this, Drew was a Navy intelligence officer, but you can tell your story.

Drew Sanocki

I was a Navy intelligence officer. That's the story. Yeah, I did ROTC at college. And the ROTC program, you apply for it, you apply for a college scholarship. If you get it, you take another class every semester at the college that accepts it. And then you go on active duty over the summer. And when you graduate, you get a commission in the armed forces and they pay typically it's like one for one so i owed them four years afterwards if you do certain warfare specialties you might have to serve longer like aviation's eight years submarines is like nine you know because the government needs to get an ROI on the training, they need to get their incremental ROAS.

Michael Epstein

Yeah. Exactly. Do they measure that with holdout tests?

Drew Sanocki

They do. They load up the PostPilot dashboard and you know, they can, they can measure their incrementality. So it's good.

Michael Epstein

Yeah, yeah, maybe some Geo lift.

Drew Sanocki

Yeah, there was solid incrementality on me. I think so.

Michael Epstein

Yeah, I bet there was, but you had, your experience was on an aircraft carrier, which I thought, I've always thought was, was really cool. And, and one of my favorite posts that you've ever done on social was some of the nicknames for some of the guys on the aircraft carrier with you.

Drew Sanocki

Yeah, I was an intelligence officer, aviation intelligence. So you get assigned to a squadron. Every squadron has one AI aviation intelligence officer. And then when the carrier gets underway, the air wing flies out and all the squadrons in the air wing, I don't know how many there are, 10 or so. And the aviation intelligence officers then like detach from the squadron and go and work in the carrier intelligence center with the other ones, with all the other intelligence operators on the ship. And so I was on an aircraft carrier, lived on the aircraft carrier for two years, went to the Persian Gulf and back. And then after that, I did some submarine stuff in the Navy. This was like after I lived on the carrier.

Michael Epstein

Yeah, it's awesome. it was, not everybody was like a maverick or an iceman.

Drew Sanocki

No, they rarely were. Sometimes in the, you know, the fighter squadrons, they had like the cool like Mav and, you know, Iceman. But more often than not, it was like you pinpointed some like something physical on someone that stood out. You wanted to make fun of, you know, we had Reek who had really bad BO. TicTac had bad breath. I could go on. Most of them are X rated. I'll just say like they're on. don't know. Maybe I'll retweet that thread that I had from a while ago. The Highlander like ejected three times. You know, just stuff like that. So long good.

Michael Epstein

Yeah, I know you've also brought and there were you've referenced a number of leadership lessons that you've learned that you learned during your time in the military and I you brought them to both a lot of the turnarounds we worked on and even to post pilot.

Drew Sanocki

Yeah, this is, you know, you said you wanted to talk about this on Memorial Day, and it was kind of like, all right. I I did a little thinking in research and there are a lot of you know, there are some posts out there about how like the military gets you ready to for business, know, for the corporate environment. think at our company, it's been a little bit different because you probably know the things as well as I do, there things we talk about all the time. Like the first thing that came to mind is we always talk about respecting the chain of command, you know, and we've got a really high sensitivity. Maybe it was because I was in the military, but, what does that mean is it's typically like everybody has one boss and only one boss, you know, and it's, and it's unified. Like you can trace your boss to his or her boss, to his or her boss all the way up to the CEO.

Michael Epstein

Yep.

Drew Sanocki

And everybody sort of knows where they reside in the chain of command. And it seems kind of obvious, but I think the problems manifest in a startup. Or if you're not like brought up with that sensitivity to a chain of command, you get a lot of like people jumping the chain of command, you know, as I'm you and I are the CEOs, but someone might come up to us, a very junior person at the company and ask for something and be like, well, you you should have checked with, did you check with your manager? And you do that out of respect for the manager because you've got to empower that manager to lead his or her team. So you can't disempower them by going direct to their direct reports. Right. And then it's also, it just, it makes a lot of sense for your employees, like not to have multiple bosses telling them often contradictory things. You know, they've got one boss, one person they report to. So I think we've always had a good sensitivity to that, whether it's been from the military or not. But I know we've talked about it at our turnarounds, getting really clear on the chain of command. And we talk about it a lot here.

Michael Epstein

Yeah, and I don't, it doesn't necessarily mean that we shut the door on people if they raise a concern and want to, think that they're not, it's not being addressed by their manager or it's urgent or they have feedback or something like that. So I think there's, there's a little bit of a balance between having efficiency and speed and communication and in some cases when somebody needs to escalate something, ensure it's getting escalated. But to your point, I think it's most prominent in ensuring that the team, you're not taking the authority away from the managers and supporting them and also not creating a situation where again, people are likely to feel like they're getting pulled in multiple directions by multiple bosses.

Drew Sanocki

Right. So another thing I came up with is decisive and confident decision-making. So I think this probably, it's relevant to the whole military, but in particular to my job as an intelligence officer is like, you never have complete information. We'd be in the ship and we try to develop a tactical picture of what was going on in Iran or in China. Like, where are the surface-to-air missiles? Where are the surface-to-surface missiles? What's going on with the nuclear power plants? Whatever it was, you try to develop a good picture, but it's never... You don't have 100 % of the information. There's always ambiguity. There's always contradictory information. And I kind of think it's very similar to running, in the old days, loading up Google Analytics. You're trying to figure out what's going on on your website, you know, or what your customers respond to. Like you're never going to, you're never going to be hit over the head with like the exact answer with complete data. And you still, and yet you still, can't let that paralyze you. You still have to make a decision ultimately and be comfortable with that ambiguity and be like, you know what? Either we have a disagreement here or there's some ambiguity. And yet we're going to decide and commit. And we use that a lot at PostPilot. talked about, we talk about decide and commit.

Michael Epstein

Pick a path. Yeah, I love that one. It reminds me also of the Amazon concept of the one way versus two way doors and the level of sort of precision and analysis you should do for certain decisions is much less than other decisions. One way door is something that you're pretty committed to if you make that decision. So you want to give it more rigor in terms of the decision making process and analysis to a door. go through it. You don't like it. You walk back the other way and you reverse it. So yeah, I love this. And again,

Drew Sanocki

Right. The key is just making a decision, moving forward.

Michael Epstein

Yep. And what's your third?

Drew Sanocki

Ownership. So ownership's a core value at post-pilot. but then I'm reminded of Jaco's book, you know, extreme ownership. just think in the military context, means there's such an emphasis on delegation and how to delegate and when to delegate and how you can delegate. Like the responsibility to do something to one of your subordinates, but you can't delegate the fact that you're accountable for it. Right. Like you are still responsible for getting XYZ done. You delegate it down to your team. But when you go, you know, when it's a do when the projects do, you don't go to your boss and say, like, well, I delegated it down and they didn't get it done. You know, it's still on you to get it done. So sort of that delegation, holding people accountable. And that's really the way to train people to lead, is you give them full responsibility to do a project. You give them the resources to do it. You discuss a deadline and then hold them accountable to perform. You know, operating in like the Persian Gulf is very different from operating in the South Pacific. And that's on a ship. I can only imagine what, you know, a SEAL team would experience in an urban environment versus a desert environment. You just got to be adaptable. You can't let it impact you. And I'm reminded of like one of our mentors, how he would in the private equity world would always tell us just to stay in the pocket. And that's what kind of comes to mind is like the threats change. They change week to week. Tariffs are on now. Tariffs are off. Now they're back on or whatever they are today. What do you do as a CEO and a leader? At the end of the day, like the more you just stay in the pocket, know what you can control, focus on what you can control, make the best decisions. Don't completely lose your shit. You're doing okay. know?

Michael Epstein

I love these. I've learned a lot from you and watching you practice these, these, these traits over the years. And I'm just reminded of the war room that we had years ago at one of the turnarounds when you were wearing the general's uniform with full cigar, eye black, everything. We'll have to post that with, with this podcast.

Drew Sanocki

Yeah, was certain. Those were fun. Those were fun days. But, you know, I think even at Postpilot, like it's very different company today than it was, you know, two, three years ago. We've always tried to delegate. We've always tried to have a clear org structure, well-defined roles. And that's been so probably more of it, more of a challenge at Postpilot than in the military, you know, in the military, you know exactly what you're going to do. That role's been there for years before you. It's going to be there for years after you. It's very well-defined. But for us, mean, being a CEO in the early days is very different from being a CEO now. So the roles are really changing. You could probably say that about everybody at the company and what they do.

Michael Epstein

Absolutely. And in the early days when it's small, lots of people are doing lots of different things. And then the other challenges growing at the rate that we have, you know, going from five to over 100 people in a very short amount of time, it's, it can, even more important to try and keep the org organized and keep that structure in place so that people know what they're doing and not everyone's just operating on their own or going off in different directions.

Drew Sanocki

Yeah. All right. I had another post that got some traction this week. This was my top regrets post. Incidentally, it's always the posts that I kind of just I just throw together that go the most viral or become the most popular. I wrote one about being old or like marketing to old people. And I was defining myself as old, you know, a year ago that got a ton of legs. I felt like it brought all these these angry seniors out of the woodwork on LinkedIn. And I did one not too long ago where I said, you know, cutting usually HR is bloated when you take over a turnover and you got to cut HR down and literally like everyone in HR on LinkedIn like was just shredding me in my comments from there. This one was about top regrets as a 53 year old. So I'm 53 Mike, what are you, early sixties or?

Michael Epstein

65, yeah, 46.

Drew Sanocki

46. I don't know what got me thinking about regrets, but it's like I was walking the dog in the morning and just kind of thinking like, hey, two or three regrets came to mind. And those would make an interesting post. And normally I don't operate from a place of regret. I don't. I'm very happy in my life. You know, I think I got to say all that stuff before getting into them. And I'm curious what yours might be. But I said the first one was not having kids younger. So I had kids when I was in my early 40s. I guess I got married in my late 30s. So yeah, maybe 40. had my son and my kids are just like the best thing in the world. And I love hanging out with them. And so in retrospect, you know, if the stars had aligned a different way, it would have been nice to have kids younger. Not just because I think it's like a young man's game, which it is, but because I could have had more of them, probably, and I would have had more. So that was one of my life regrets, not having more kids younger.

Michael Epstein

You know, I had kids when I was, early thirties and part of the reason that I did that, part of it was intentional in that, my parents had me when they were on the older side and they, my dad wasn't always in the best physical condition, to, you know, be as active, I think, as he wanted to be. Not that, you know, he had severe issues or anything like that, but I just know, shoulder surgery and the stuff that starts to break down as we get older a little bit made it made it harder for him so I I had that in mind when I had when we had kids a bit earlier, but at the same time I think my regret is and I know you talked about some of this in in the rest of your post to is Always feeling like it's gonna get easier next year from a work perspective and that I'll be able to carve out more time and focus more on that. Not that I'm an absentee father, I'm not. I feel the same way you do. My kids are just the light of my life and the greatest thing ever and spending time with them is the greatest thing ever. But feeling like it's gonna get easier and I'm gonna be able to have more time with them next month, next quarter, next year, never seems to happen. And I think it took me too long to recognize that that was just not gonna happen and make the adjustments that I should have made.

Drew Sanocki

Yeah. And maybe this part of the podcast is just for those who listeners who have not had kids yet. But I would say, you know, you go through this phase where it's physically just so hard to carve out any time to do anything other than to help with the kids. Right. And it's not the time to like go all in on starting a business, you know. And that was probably for us, I don't know, from age zero to six. And that's a good time to consult. It might be a good time to get a nine to five somewhere, to just be working somewhere else in someone else's company. And then there's that magical time. I think it was around five, six for us, where my wife and I kind of walked in on the kids and they were playing with each other like up until that day, like for years, they would not play with each other. They just want you. And then all of a sudden they're like content and you're like, my God, like I can I can now do something. I can take up a hobby or start post pilot. So there's that, you know, just budget that in when you have kids that there's going to be those five or six years that you're not going to be able to do something else, or I would say choose a partner who's on board with the program of like one of, you know, either the partner or you is like full-time caretaker for the kids. That's another option.

Michael Epstein

Yeah, fortunately, that's been my wife on our side. But again, just having that I've heard this mentioned a lot. I don't remember where, but I think a lot of people say it's just, it's a shame that it tends to be, you know, your peak income earning years tend to overlap with when your kids are still in the house and still actually interested in you and what you're doing and want to be with you and you know for me with my older daughter now in high school coming to the realization that how many years left? Like I'm on the clock right now. How many years left before she's out of the house? And then I came to the further realization that it's not even how long until she's done with high school. It's like next year she's going to have a driver's license and that's going to be a change in how much she's around, I'm sure. And, and how much she wants to hang out with me. And that's, that was a tough thing to come to terms with. And I still struggle with that a lot.

Drew Sanocki

Yeah, is she to the point where she's like, screw you?
Michael Epstein

Not yet, but you know, the eye rolls, the jokes aren't funny anymore. Yeah, so we're at that point. yeah, it's tough to come to terms with and going back to what you were saying originally, recognizing that early and sort of planning your life and your commitments around that is something that if you haven't gone through this already, hindsight, I might have done that differently.

Drew Sanocki

Yeah. And so that ties into the second regret, which is about taking risk at various points in your career. And I think in my life, in my 20s and 30s, when I was the time for me to take a lot of risk, risk in terms of like, start something, you know, swing for the fences, like go after it with that big startup, instead of playing it safe, climbing up the corporate ladder or, you know, just pissing them away like in the Navy, dating, whatever. Like, you know, I think there was that window probably late 20s, early 30s. I wish I had. I wish I had gone for it, you know, and I think for me, that was because I think I said in this post, you know, like going to Harvard and going to Stanford for business school is kind of like, it's kind of like these golden handcuffs are in a way where they, you come out of there and you don't want to fail. just, you're, and so you, you're much less likely to take a risky course of action to bet it all on a startup, you know, and no, you got to go to McKinsey and Goldman and just like kind of do a much more conventional thing. But I think the 20s, your 20s and your 30s when you're not married and you don't have kids is exactly the time to mess around and try to like build something big and take on a lot of risk because there's no downside if you fail.

Michael Epstein

I think Scott Galloway talks a lot about this, you know, what to do in your early in your career when you can swing big and you, know, if it fails, no big deal, you got time to start over. But I thought the most interesting part of your post was that aspect of the expectations put on you, whether self-imposed or real about, you know, having that pedigree and then coming out needing to do something incredible.

Drew Sanocki

It's like your roommates all do amazing things and amazing, but conventional, you know, and then business school. I bet if you interviewed everybody from my business school class, they'd say a lot of the same thing. You just kind of have this pressure to go do something. I don't want to say something amazing. It's something more conventionally successful. You know, I'm going to go get on this track to become a partner at a venture firm. And there are only a handful that said, no, I'm just going to work in, be profitable at a startup for a couple of years, my own startup. Because, man, you've spent so much money on your education at this point, you've got to get a return on it. You don't want to take that kind of risk. And now, I don't know how you feel, but now, our kids are about the same age, so I feel like you and I are the same life stage, even though I'm, you know, I'm what am I, nine, eight years older, something like that, seven years old. So it's like. Our career, our career lifespan is kind of like. Like how many more years do we have in us at 53, like everybody we bump into out there is younger than we are at every DTC conference at every software company. The one exception I thought, you know, public company CEOs are around our age. But other than that, like how many more at bats do we get? You know, and so I think that that causes us to run post pilot in a certain way where we're not going to, you know, we're obviously like growing it like crazy, but we're not going to do it in a way that if it doesn't work out, we've burned the thing to the ground. Does that make sense?

Michael Epstein

It does. Yeah, we run it in a responsible, high growth responsible way. But to your point, we were both we both said this from the beginning, like this is this is the big one. This is the opportunity. This is sort of the culmination of everything that we've done and every experience we've had throughout our careers. And it all sort of led to this and this, yeah, given our ages and where we are in life, we want to make this the home run.

Drew Sanocki

And you'll probably be able to tell what kind of exit we got off PostPilot, because afterwards, if we have some kind of insanely massive exit off PostPilot, like it's risk on again, no matter how old we are. Right. It's like throwing million dollar, you know, angel checks at AI businesses left and right.

Michael Epstein

Right. I thought you were just going to say we were going to put our big matches next door to each other. You'll know what kind of exit. Yeah.

Drew Sanocki

We'll do that too, or drive the cigarette, the two cigarette boats.

Michael Epstein

Exactly.

Drew Sanocki

So, yeah, don't optimize around the wrong metrics. You know, at various times, I was optimized around income, around wealth creation. When in retrospect, I find that my family and my family has given me much more of a return. So I just think it's a little bit of like, be careful what you optimize around.

Michael Epstein

Yeah, and they say once you're past a certain point, the incremental happiness you get off certain levels of incremental wealth goes down significantly. But again, coming to that realization is hard.

Drew Sanocki

It is. I think we're both kind of there. Like, I don't feel like I need to skimp on anything. You know, I just like my needs are being taken care of. You know, it's it's sort of. I'm certainly not optimized around the wealth metric anymore.

Michael Epstein

I think that we're, no, that's not where my happiness resides. I do have just a general sense of pride and drive to build, to sort of execute the vision that we have for the company. But wealth creation as a result of that is not the primary driver. I think it's more just the execution of the vision, going back to what we were talking before, knowing that this is the culmination of all of our decades of experience, making sure that this is, that this has the level of success that I think you and I imagine it should and can have. Because I want to show that all of that, that work and experience and, and everything that we've learned over the years.

Michael Epstein

Yeah.Produces like the outcome that we want and is a great outcome for our customers, our employees and ourselves.

Drew Sanocki

Any other regrets?

Michael Epstein

No, it caused me to think and I'm glad you wrote that. But I think the main one was around, well, all of them were really around family and how to think about priorities. And I was glad that it gave me an opportunity to do some of my own reflection.

Drew Sanocki

Well, a good thing for Memorial Day, you know? Youth is kind of wasted on the young, as they say, Stane. You We had to do it all over again to be a little bit different, but happy where we are and very grateful. Happy to be partnered with you. think we're doing a good job and excited for the next year. So that's all I got on regrets.

Michael Epstein

To your point, working with you has been one of the highlights of my life and career and the fact that we've gotten to work together for so long and done it in the way that we've done it has just, I think about it frequently and just have a lot of appreciation for that.

Drew Sanocki

I do, too. And I, you know, for those of you who don't know, Mike and I have been working together for 15 years, something like that. And a lot of on a lot of like failed ventures or not failed ventures, but. Turnarounds, yeah, but certainly like, you know, you moved out to San Diego to work on auto anything with me right into COVID. And so there was a little bit of like, we've in that one was like, OK, we made a couple of acquisitions. It's growing. This is great. You know, I'm not feeling guilty that Mike just moved his family out here because this is going to work. And then COVID happened. So it's nice to be finally, you know, we've got some validation that it's working with PostPilot now that it's working. So knock on wood.

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