8. Nate Lenahan on Leadership Through Transparency and Buy-In

January 19, 2022

8. Nate Lenahan on Leadership Through Transparency and Buy-In
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In this episode, Tim and Brock talk with Nate Lenahan. 

Get a weekly episode breakdown, sneak peak of the next episode, and other resources in your inbox for free at https://scuttlebutt.substack.com/.

Nate spent six years in the Army followed by eight years in the Army National Guard where he worked in artillery. Nate promoted quickly and served two tours in Iraq from 2003 to 2004 and 2005 to 2006. After his active duty exit he got to teach sergeants Army leadership as well as be activated to assist with Hurricane Harvey.

Nate went on to work for Lockheed Martin and participate in many of their leadership development programs. Follow Lockheed, Nate got involved in the property management and real estate space and was a regional manager for WeWork. Since WeWork, Nate has dove into the SMB space, particularly buying and scaling home services businesses. 

You can follow Nate on Twitter @n8lenahan and on LinkedIn


Whether you’re in the service for four years or twenty, you have learned skills, led teams, and learned what it takes to execute under pressure. While those past successes are valuable, they don’t always translate to a life or career when you get your DD214.

Join Tim and Brock as they break down the skills and strategies current and former military members are using to build a successful careers on the outside the service.

Follow along with us.
• Tim: @Mccaurthor, https://www.youtube.com/channel/UCbJ5Ly07sxv2lrofAiN16aw
• Brock: @BrockHBriggs
• Instagram: Scuttlebutt_Podcast
• Send us an email: scuttlebuttpod1@gmail.com


Brock Briggs  0:18  

Hello and welcome to the Scuttlebutt podcast. Our guest today is Nathan Lenahan. Nathan spent six years active duty in the army followed by eight years in the Army Reserve, working with artillery, including a couple tours to Iraq. And now, over the last few years since getting out, has worked in real estate and property management, and has since bought and scaled multiple of his own companies. Nathan, welcome to the show!

Nate Lenahan  0:45  

Thanks so much, Brock! Appreciate you both having me here and excited to share a little more. Just to make a correction, it's the Army National Guard, not the Reserves. There's a big difference.

Brock Briggs  0:56  

Okay. Thanks for jumping in there. 

Tim McCarthy  0:58  

Yeah, I did not realize that there was a big difference. I thought the National Guard and the Reserves are the same thing.

Nate Lenahan  1:04  

So actually, Reserves is federal. So it's just like, that's the first force that would be an auxilary for like the US Army or US Navy or whatever it may be. And then National Guard's are basically state militias that can be federalized. But there's a big difference, because National Guard's are typically fighting forces or like combat arm, like artillery, infantry tanks, like that kind of stuff. And Reserves is typically more like administrative functions or service and support functions. So actually, there's a big difference, honestly.

Brock Briggs  1:34  

Well, that's how I know I'm gonna like you as jumping in here and correcting me, right? You're a guest on this podcast, okay? 

Tim McCarthy

No, no, you're good. 

Brock Briggs

That's perfect. Yeah, we appreciate you having taken some time to come on with us today. Do you want to give us the five minute quick and dirty of what led you to join the army? And then what leads you here today?

Nate Lenahan  2:01  

Yeah. I am one of the oldest of seven kids. I come from a military family. My dad's proudly served in the Navy for 35 years. And I think it was an incredible example, starting, enlisted and commissioned eventually, and just like, that guy knows how to work his ass off, and I love that. And then I have a twin brother. And so he joined the army right out of high school. And also I thought it was just a great example. 

But I can tell you the biggest catalyst was me getting in a little bit of trouble in my first semester of college, and 911 happening too. It just all came together in this glorious kind of push to join the army. And so I did and, like probably one of the best decisions I've ever made in my life. 

So after that, I got to do six years active duty, which was incredible. Served two years in Iraq, right when the war started, so 03-04 and then 05-06, got promoted quickly. I was in artillery. So got the blow big, you know, all kinds of crap up, which, you know, I absolutely loved. I loved being in combat arms. We were just like a little bit more gritty and a little, you know, very results oriented, very training oriented, and very leadership oriented. I saw some of the best leaders you could ever, ever see anywhere and some of the worst ones as well. And I think they both really developed me as a leader. 

Then I left active duty, went into the National Guard as I finished my bachelor's degree. I got to be an army leadership instructor for sergeants who are learning how to lead other soldiers. And I really just loved like the time there as well. Favorite highlight there was probably just getting activated for hurricane Harvey and serving down there in Houston and helping my fellow Texans, especially the crazy part on that was I just started a brand new job my first day. And then I got activated for it. And so I was like, “Hey, boss, I will still start today, but I just got a call. I gotta head to Houston, and pack my bags.” 

And I just remember him trying to figure out he's like, trying to control the situation, “How long is it going to be?” You know, like, “When are you gonna be back.?” Like, I just gotta go ahead and reset priorities for you, my friend. Like, here's how this goes. Like, here's my priorities, mission is number one and that'll be taking care of. Family’s number two, and then that's what's going to happen. And then you're number three at best. And he's like, “Oh, you know what, you're totally right. We'll worry about it when you get back.” And like it was so nice to see him kind of readjust. And so like Hurricane Harvey, and that experience was my highlight in the National Guard but absolutely loved my time serving and I can't wait to share more.

Brock Briggs  4:23  

Cool. Will incriminate you to tell us what kind of trouble you got in?

Nate Lenahan  4:31  

No, no, no. Like I'm an open book. And so at 18, my first semester in college, I had come from a pretty conservative family too. And I was actually at a pretty conservative school so it's easy to get in trouble and I liked the ladies, guys. And so I might have been on the way to what I called an “oops baby” between that, and then like not going to enough classes, and not getting good enough grades. It all was kind of coming to a culmination and so Army seemed like a great, great path after that to the pay and I was paying for everything too. 

And I couldn't quite figure out how to balance working 40 plus hours a week and paying for college and having fun and getting in trouble. So the Army seemed like a good thing to maybe give me a little discipline and help pay for college and get the leadership experience I was kind of hoping for as well.

Brock Briggs  5:23  


Tim McCarthy

That's cool. 

Brock Briggs

I think that that is the story of so many people where it's like, my life is just like, maybe not going to shit totally. But like, there's all these really, really bad things that are happening. And then in hindsight, kind of like looking back on because I have a very, very similar story. But like, looking back on that experience, and it's like, “ You know what, will really just make everything better is if I just completely leave and just throw my life basically up into somebody else's hands.” And like, “I just don't even have control of anything anymore. Like that will really, really, really help me.”

Tim McCarthy  5:57  

Set me straight.

Brock Briggs  6:01  

And it does, which is funny in a weird way. But like, I think coming to grips with that logic doesn't really, doesn't compute.

Nate Lenahan  6:10  

Yeah, it's funny because I resisted it pretty hard because I'd gotten a full ride for like Naval ROTC at Virginia Tech. And my family lived in Virginia and like the Norfolk area, that's where my dad was stationed. And just despite my parents, I was like, “I can't do it, guys. Sorry, I'm gonna go to this school in Utah. That's like nowhere close, you can't help me. I'm just doing my own thing.” And you know, that kind of blew up my face on a wonderful way but still blew up on my face.

Tim McCarthy  6:36  

I don't know how many people I've like in the military have that just like you're saying Brock, like that same exact thing. Like, oh, “Yeah, I tried school, like, was not for me. Or I got into trouble.” I remember my first day of college, right out of high school. I showed up to class and the teacher, the professor, whatever is like, “Okay, open your books, like page five.” And I'm sitting there and everybody's pulling this book out. And I'm like, to the person next to me, “Where did you get that book?” Like, oh, “It was like, emailed to us. Like, you have to go to the bookstore.” And I was like, “Oh, yeah. Okay.” I go to the other side. And I'm like, “How do you get into your email?”

Brock Briggs  7:15  

We’re not in Kansas anymore, toto.  

Tim McCarthy  7:20 

Yeah. Like, I was not prepared for college at all. It was like at that moment where I was kind of like, “Oh, I fucked up like I shouldn't be here.” 

Nate Lenahan

That's funny.

Brock Briggs  7:33  

You said that you served with like, some really incredible leaders while you were active and deployed. What stands out to you about those and like, I'm curious, that dynamic of maybe your life kind of not being in like a super great way you joining? And then are you still kind of like, are you still the troublemaker there? How do those leaders kind of play into that? And I guess what's the learning there?

Nate Lenahan  8:03  

I'm honestly, like, mostly a rule follower. Like I'm a pretty good kid. And when I get in trouble, it's I mean, it was like everything expected, you know, girls, mostly not doing what you're supposed to in class. But in the army, my mouth got me in trouble most of the time, because I'm a bit of a like, I have a bit of a little sarcasm. I'm a little lippy. 

And if I'm really honest, like I got in, and I kind of looked, you know, do bootcamp, looking to the left and right and like, “Is this my competition?” Because I didn't know what I was, like, very good at anything until I got here. And you're like, “Okay, like, I might be pretty good at this.” And so, but my favorite leader, the first experience I've ever had with him is he showed up. He joined our unit in Iraq, so I've never met him before. 

And my first experience is, here's this Puerto Rican guy, and he shows up and he drops his bags in my hands like I'm a freaking bellhop or something. And he goes, “Because where's my Puerto Ricans at, just leaves me there?” And I was like, “Oh, okay, well, that's I've never experienced this before. This is a little different.” And he was just like, I think he had this, there's this quote that says like, “Nobody cares how much you know, until they know how much you care.” 

And I think no matter how much he was, like, cussing me out, or like trying to make me better, I always wanted to be better and I always knew that he cared. And still he texts me every Christmas, every few holidays, say “Hey brother, how's it going? How are you doing? Thinking about you or whatever.” And he's also like just cussed me out to oblivion in a way that you know it's very hard to do outside the military. But no, I didn't cause too much trouble as a private. I was pretty lippy and that really caught me up. But as you get higher, then you can have that mouth a little bit more and be appreciated for it.

Tim McCarthy  9:41  

Oh, yeah, for sure. 

Brock Briggs  9:44  

Yeah. That early on, you're just like shooting up the flare is on like, “Hey, I obviously need more discipline here.”

Tim McCarthy  9:53  

Pay attention to me.

Nate Lenahan  9:56  

I really need bigger PECS to do them push ups. Yeah, I mean, there's just lots of groups, great groups in general like I mean, that's one of the things I love most about the Army is just like, it's so diverse. 

Tim McCarthy

Oh, yeah.

Nate Lenahan

He was never afraid to be like, “Where's my Puerto Ricans at? Not Hispanic, Puerto Ricans. That's what I want to know, my island.” And I always love that about him, a lot of pride.

Brock Briggs  10:16  

I think one of the things that stands out to me about the military and like talking to people after they've gotten out, as you pointed out, like, “Oh, this is my competition.” And, you know, I think that the rest of the country has this idea about the US military, like, you know, they're just like this elite fighting force, like everybody immediately is like, everybody has a Navy Seal. Like, there's this, like, everybody's Special Forces, like in totally good shape. 

And just like super overachievers, and like, that's not the case.

Nate Lenahan

I know. 

Brock Briggs

And like, it is not hard to stand out in like a positive way, in a negative way too. But in a positive way, if you just, you know, you got the right uniform on, you show up on time, like just doing the basic things, like you can really set yourself apart. And I think that the problem with that, that's good, but it leads the elite performers to get out. 

And a lot of the longevity of people's military careers, I think it's drastically lowering over time. And I think in the next 10 years will probably be significantly like, I don't know what the average tenure of people in is. But I'm guessing it's getting lower over time, because it's those people that are elite and do really well should just get out.

Nate Lenahan  11:40  

Yeah, it's really hard. Because everyone's afraid to say things like that. I think, where we love to think that our military is our best and brightest. And there is a portion of that. But on average, it is. Like I think the most common thread is like people do want to be here. They want an opportunity. And they're willing to give up something you know. So that's a little bit of freedom, or a little bit of choice or whatever, to get something out of it and hopefully serve the country. And I found that to be very true. But like the best and brightest, on every side of you is not the case. Which like, it sucks to say, but there's incredible people in every direction. It's just, it does not take a lot to stand out.

Brock Briggs  12:18  

Is that? Are we going to put you in that best and brightest category? Is that why you got out or what I guess what really led to you getting out?

Nate Lenahan  12:28  

Honestly, I love the military. And the biggest catalyst for it was I always wanted to be an officer. And so I came to be enlisted. I really, really, really wanted to be an officer. My father did it. It was a big goal of mine. And actually, when I went through the process and got the physical and all that stuff, all the things that were wrong with me from serving in Iraq and doing things, you know, kind of popped up. 

And life just got really difficult at that point where I was like, “Okay, it's not worth it anymore. I'm just gonna go out. And maybe I'll figure out a different way to do this, but I'm getting my degree one way or the other.” And so I would never tag myself the best and brightest, but like, I was pretty good at what I did. And I wasn't gonna let the Army or anything else get in the way of the goals I had. And so I did.

Brock Briggs  13:08

What were those goals other than just the degree or was it just that?

Nate Lenahan  13:13  

Yeah, I mean I had a couple of big ones. So, you know, I knew I wanted to get an MBA at one point. I just remember coming back from Iraq the first time like, 2004. You know, I'm a private first class or like a specialist like before. And I read about this thing called an MBA Masters in Business Administration. They make an average 120 grand, I'm like, “That's all I gotta do. I just got to do that. 

Tim McCarthy

Yeah, yeah.

Nate Lenahan

120 grand, I made, like, you know. To me, I'm making like 700 bucks a paycheck at that point with a family of three and I'm like, “Man, 120 grand, can't even fathom that money.” 

And so, I want an MBA. I was really, really into real estate. And so, you know, like the love letters I sent home to my wife just show how big a nerd I am. You know, because they'd be like, “Oh, babe, I love you so much. Send me this in a care package. Also, if we just bought the four plex that we live in right now and we rent it out the other three units, we can cashflow this much a month. And then if we cash that much a month, we just save it all and then we could buy another one. And like eight months, and then the second year if it bites you.” And so I'm like, “Man, I'm a major nerd.” 

And I actually came across like the love letters or whatever recently, like, “Oh, man, I'm not romantic enough for you. Thank you for keeping me around.” It was, it's pretty nice. So that's like just building a real estate portfolio, getting that MBA and I really wanted to do my own business one day. So those are things that I knew were going to be out there. And at one point, I was okay with doing the business after I retired from the Army. And the real estate I figured I just do along the way you know. I buy one or two each police station and just keep building on that etc etc. Ultimately, that didn't happen. I got out after six years and went straight to finish my degree. But I have hit every one of those goals along the way.

Tim McCarthy  14:53  

That's awesome. That sounds like Brock, like being a big nerd thing. First I heard Brock, was like first getting into Finance, we were on the ship together. And he's like, “Oh, I'm missing this quarterly call, so I can, you know, hear what kind of dividends are returned.” He's like using all these like Finance terms and I'm like, “Go off dude, like, do your thing.” That's so funny.

Nate Lenahan  15:16  

Well, I can tell you I just, I would consider myself a high performer when I was in the Army. And so I left as an E-6 after four years, or after six years. But I can tell you leaving the Army and in kind of like climbing that ladder quickly, having a lot of responsibility, the best job I could find out after was $11 an hour at Sprint and doing customer service. And I gotta tell you, like you want to endure something very sobering or get your ego in check. That's a great way to do it, especially when you have a family, at that point, I had three kids. And I just had my third. 

And so you know, very, very tough time for me. And I remember, you know, I had gone to like a VA or sometimes like thinking, I had these thoughts of like, “Hey, I was one of the lucky ones.” Like, I never got blown up. I have bad hearing loss. That's about it. Like I'll take that all day, every day. And I was really struggling in college. I really hated life. I was kind of like that, like, weird, disgruntled veteran in class, older than all the students and stuff, you know. And I just remember, like, starting to have bad thoughts. Like, I didn't have friends. I didn't have that college experience that people talk about. And I've gone to like a VA center and like, “Hey, I'm having bad. I'm not having good thoughts. Like, this is a bad path. And I want to talk to someone.” 

I just remember, they gave me a pamphlet and like, sent me on my way. And you wonder, like, why do bad things happen? And like, stuff like that is why bad things happen, right? But I can tell you, what I realized I was missing the most was the friends, it was the community. And so I can just tell you one day, I was like walking across campus. I'm having like this pity party for Nate. And I'm like, you know what, no one cares, man. Like, nobody cares. Nobody cares about your pity party here. There's only one person that's gonna change this and it's you. So you're going to change or not. And I literally stopped like mid step, turned my butt around and told myself I was going to change it. 

And what I did was I actually walked over to the football team and decided even though I've never played football in my life. I'm going to walk onto our division one top 25 football team and start playing. And so I've managed to talk my way through like three gatekeepers, got my way into one of the coach's office and basically realized, because I started college before 911. And it's a ticking clock. You have six years, so I had no eligibility. So that's the real reason I couldn't play division one football, just so you know, had nothing to do with talent or anything like that.

Brock Briggs  17:43  

But you did that one great.

Tim McCarthy


Nate Lenahan  17:46  

I mean, I could have been like, third walk on, on preferred for sure. But I just remember, like, “Hey, okay, I got it. I can't play. Is there anything, I just need to be a part of the team. I need to be part of something here. I need that community. Or like, it's probably not gonna go well, and I'm like a volunteer. I'll do anything.”

And so the coach actually walked me down to the director of equipment. And they have student managers who basically run all the practices. They run the sidelines. They run the locker room. They travel for every game. They are on full scholarship. And they get stipends. And I walked down there. And I interviewed on the spot with the director of equipment, whose son just happened to be a US Marine in Afghanistan at the time. And man, I'll tell you why, like, I got the job. I got the scholarship. I got the friends. I got everything I was looking for. 

And it all came down to just like, well, shit, like, did you try or did you not because no one else is gonna fix this for you. And I had the audacity to go find a job that I didn't even know exist. And I made it happen, which was pretty cool. And I think that act of doing was the biggest thing after the mindset.

Brock Briggs  18:54  

You know, it's really easy to get, like, poor me as a veteran, I think, which, that's so I don't like that part. But it's very, very easy to think about how bad you have it. And, you know, the lack of resources. And you know, it's I feel like I'm going back to my teenage years. Like, nobody understands me, you know. Like, I’ve done all these things. 

And now I'm like doing group work with these 18 year old kids that literally have done nothing. And that's a very, very difficult thing to overcome. And I will say it's probably not as simple as just like, that's a very inspiring way to just be like, “Oh, I just like decided to not be that way.” But I think more people need to think about that and realize that it isn't. It can be a pity party if you want it to be. But it doesn't have to, if you don't want it to. 

Nate Lenahan


Brock Briggs

So you were up..

Tim McCarthy

Go ahead, Brock.

Brock Briggs

No, you're fine. Go.

Tim McCarthy  19:58  

So you get the scholarship. You finish high school, I'm assuming. And then what was your first move right out of college?

Nate Lenahan  20:08  

Yeah, so I went to college in Utah. And I got into an operations Leadership Development Program with Lockheed Martin. So huge defense, largest defense contractor in the world, super sexy name. And I was just like, “Man, I made it. I'm like, I'm the shit, you know.” And it was, it's an incredible company. I went there, and I part of the rotation. It's two years. We do one, you do four rotations or six months, you know, different disciplines. 

So like supply chain, or quality or operations, and then whatever you do. I did a year in New Jersey, which I hated New Jersey, didn't want to stay there. And then I was just trying to get to Texas or Colorado. And so we ended up in Fort Worth, Texas, where they built the F-35 stealth fighter jet, which was super cool. And I got to be a part of that, you know, in the building. I was doing facility management for them there. 

So I got to run the building that it's like literally over a mile long, just as one building. And it's just like the main assembly line for the F-35. And so that was pretty inspiring. But what I learned very quickly is regardless of what the name on the building, you work for the US government. And I was not really interested in that anymore. Like I like to move too fast. I like to break things. I like to try things. I want to not be micromanaged. And so, I started five years with Lockheed. They paid for my MBA, putting me to that leadership program. Let me throw another leadership program and so incredibly grateful for the time there. 

But also, I learned what I didn't want very, very quickly, which was also like, just as incredible, right? So yes, I went there. And honestly, the last six months or so, I moved to a new job where I'm working midnight shift. Essentially, I worked from 4pm ‘til 3am. And this is going to be like me kind of knowing I'm good at stuff or decent at stuff. And I told the manager when they hired me, I'm like, “Here's gonna be the problem is all I want is night shift. Because I wanna work on my own business during the day.” And I'm gonna be, this is gonna sound cocky, and I really don't mean to be cocky like, “But you're gonna like me enough that you're gonna wanna bring me off night shift.” I'm like, “I'm telling you, that's probably what's going to happen. And I would bet I don't make six months.” 

And sure enough, like went over there just did not much more than the bare minimum. And literally, they tried to, they pulled me to the day and so like. As soon as they pulled me to the day, I made it maybe a month. And then I quit because I had been working my job from 7am ‘til 3:30pm. I'd be working on my property management company and doing flips. 

And so that's what I really wanted to do. And so ultimately, like they did bring me to the day shift. And I quit a month later and went full time in my first business. So like that was a pretty exciting thing. But I am incredibly grateful for Lockheed Martin. It's a great place for a lot of people and they love their veterans. But it was a really poor fit for me.

Tim McCarthy  22:53  

So you're sleeping like three hours at night. 

Nate Lenahan  22:57  

Oh, it’s terrible, man. Like I am very surprised I didn't die driving home. I just remember there's, I worked in Grand Prairie, so like, kind of like the Dallas side of the Dallas Fort Worth metroplex. So Dallas was on the East side, for us on the West side. So I drive about 35 miles home. And there's just one curve on I-20. That's just like a really, it's a very kind of hard curve. And I just remember multiple times falling asleep in that curve and like ending up two or three lanes over. And so I wouldn't suggest anyone doing that. 

But like it shows, it demonstrates like you have to sacrifice for the things you want. And I was willing to sacrifice. You can do anything for six months to a year. And I did it for about six months. And then I had it and so I got the job full time. 

Tim McCarthy


Brock Briggs  23:44  

I think you went over something that's extremely underrated. It’s looking at opportunities and experiences you have as a way to say, “I now know that that's not what I want to do.” My time in the Navy was exactly that. Like I spent four years figuring out that that's not what I want to do for the rest of my life. But that's and that sounds like cynical and whatever kind of sarcastic. But it is really true, too. 

And sometimes maybe, if you don't know what you want to be doing, eliminating the things that you like opportunities that you have now, kind of maybe get you closer to like in your case, like starting your own company or business. Was that something that you had considered or had been on your mind for some time? Or did that just kind of spring forward from nothing?

Nate Lenahan  24:35  

Yeah, it definitely had been on my mind. Again, like the entrepreneurial volley had kind of hit me. My MBA, I can tell you again, like I'm not that great a student. I love learning. I absolutely love learning. But I'm not a great student and in my MBA, so I went to University Texas MBA. I shouldn't have gotten in there either. Like my test scores aren't good enough for that. Like I'm a much better alum than I am an actual student. But like most of my motivation was making sure I didn't screw my group mates up because you do so much group work for your MBA. 

And you know, I never want them to get less than an A, or whatever they wanted. But I would read like, I read the case studies ahead of time. Like I read all like anything that was like real world knowledge. I always wanted to plan but most of my MBA, I spent at any class looking for businesses to buy, like reviewing the financials, that this would be a good buy. And, or starting my own business, you know, like just going back and forth between that. So very much had been part of it. 

And then the last catalyst was one of my best soldiers and very good friend, his wife is best friends with another guy's wife. And he was starting kind of like a little real estate, wanting to do a real estate venture or starting a new business. And so he introduced us. And we've been close friends ever since. Like, we built that business together. We went, worked at another company together. We bought the apartment complex together. We launched this business together. And we just bought another business together. 

So like, it's incredible when you find someone that can match your pace, and like passion and discipline, I guess, to actually do what you want to and go after goals. So yes, entrepreneurial very much though. So just figuring out how to do it was the hardest part, like how do you actually take those risks, especially we have four kids and turns out kids like eating every day, like a few times, ideally, a day. So..

Tim McCarthy  26:25  

I can vouch for that. That is very true. They do prefer to eat more than once a day. 

Nate Lenahan

Yeah, yeah.

Tim McCarthy

So obviously, you have this you are talking about your goals. And even in the Army, you had the goal of an MBA and you have an MBA on average. They make $120,000 a year. Was the money the main driving force for starting this business? Was it a status thing? Is it just you had a feeling you were gonna love it? I mean, what is it that like really motivated you to move on that?

Nate Lenahan  27:00  

Yeah, it's a great question. I think over time, what I've learned about myself at least is I have more of an errant internal scorecard. Like I don't really care as much about what other people are doing. There's literally one or two people maybe in my life that every other year’s, something I'm like, “I wonder how they're doing. Let me see. Let me compare myself to them.” And that's about it. You know, I certainly have my moments of ego and everything, just like everyone else. 

But mostly, it's just like, how do I have more freedom? So like, that's an internal, that's not compared to anybody else. How do I have more freedom? How do you get freedom? Well, freedom usually comes through money. So money is certainly an aspect that matters. And like, how do you make an impact? Like, I want to do something that I enjoy, that I'm passionate about, that I could share with others. 

And so I would tell you, for instance, you know, I mentor on this platform called Better Abby. And I'm about to hit my 100 call here soon, which means at least 100 hours, and like, 98% of calls are all about real estate. And so now I noticed something I've gotten something good enough about at something that I can help others do that. And I feel like enough people helped me along the way. I just won't be able to get back. 

So if I was still working at let's say, Lockheed Martin working on manufacturing of F-35, like, do I want to be mentoring on that? Like, is that how I want to get back? It's not, it's not at all. Like, I have no interest in that. And so I think there's like really clear purpose kind of motivation and direction of like, how I think do these things and how do I get back. I want to be giving back on things that I enjoy as well. And that I actually am very good at. And so that's how I kind of came to that and I did want to imprint something. I wanted my name on something and build my own brand and see if I could do it.

Brock Briggs  28:43  

You know, it is really easy to be just average in the military, like you will just coast for 20 years if you want to. But creating that scorecard and you can really excel, if you want to. Talk a little bit about Veterati. We've talked a little bit offline about it. And I've looked at it a little bit. Do you want to tell us about that and just kind of give them a little bit of a plug?

Nate Lenahan  29:09  

Yeah, Veterati is an incredible platform where you basically just hop on. It's Daniel Raul and Diana, I forget her last name. But aside Diana, they created it, with previous veterans as well. And basically you go on and you're just helping transition veterans. And so you put a camera profile of what you're willing to help with or talking about as a mentor. And then you just connect your calendar and say like, “I want to do four calls a month or whatever.” And it literally automates everything else. So text, you saying, “Hey, Brock is interested in talking to you, Friday at 5pm. Do you want to do this?” And you say yes, and then it sets it up for you and literally calls. My favorite part because it never waste your time, kind of like I wasted your time today. 

It always calls the mentee first. And if they don't pick up, they don't call you. So like it calls the mentee. And otherwise they'll tell you, “Hey, your mentee didn't pick up. Looks like we're gonna give them one more shot if they don't pick up next time.” You don't need to worry about this or be waiting around or wondering anything so like to give it a shot. So like, I think it's such a great platform respecting mentors’ time. 

And then they send like kind of a nasty email to the mentee saying, “Hey, you just wasted this person's time. Even though you committed to doing this.” Like what's up, give us a reason why, like, it kind of makes you feel guilty. So I love the platform. I think it's an incredible tool for people that are transitioning. And I think anyone that's, especially if you're a veteran, and you've been out in the civilian world at all, you have something to offer to transitioning veterans, you know. And so I think people get caught up like, “Oh, you know, I only got two years, do I? Am I ready to be a mentor?” It's like, are you willing to share your experience, so far? 

That's it. That's all it is like, and if you have any recommendations, give it to them. But there's like a guy, me and him talked recently, and he's at Zillow. Zillow is a cool company. It's a tech company. People want to know about that. And he's only got like, he's been in the National Guard for a few years. And that's it, you know. And so he's like the young guy, but he was surprised at how much value he's been able to offer.

Brock Briggs  31:17  

I think even just going through the process of exiting is more than the person who's in now their leadership has done. So just having gone through a flight, the process of getting your DD 214. Yes, I've like checked into the local VA and like enrolled in the health care here or like, whatever kind of benefits you've used. Just like in the military, you're an expert on it just by having done it once. Because there's the way that it says to do it on paper. And then there's the way to actually do it. And usually those are, there's a wide disparity in between the two. 

Nate Lenahan


Brock Briggs

Yeah, I've actually signed up to be a mentor on that platform as well. So I'm eager to see and trying to help out with that. So that's really cool.

Nate Lenahan

I love that.

Tim McCarthy  32:09

Yeah, I've never even heard of the platform. But that sounds, it sounds really cool to do. So I personally work in sales. I've been doing that for about three years now. And about a year and a half ago, they started doing this mentorship program where essentially you're training new guys. And they picked a handful of people to do it. 

And I was one of the salesmen that they picked to be a “mentor”. And since the start of that program, I've trained, I've mentored two people. And you're like their mentor for a year. And one thing I've told Brock on several occasions is that's kind of a, I've discovered that that's a passion that I have that I didn't even know was like taking somebody under your wing, showing them and teaching them how to become good at something. Or sharing your experiences and then seeing them become successful. 

And you know, whether it's making more money than they ever thought that they could or whatever, that's a very, very rewarding thing. So I'm definitely gonna have to check that platform out because like I said, that's a passion. I didn't know that I had, but over the past year and a half, I've loved that.

Nate Lenahan  33:24  

For sure. Sales is such a great skill set to share and help others learn. And so 

Tim McCarthy

Oh, yeah.

Nate Lenahan

That's cool, too. They like, if you help someone and they get to actually get the job or whatever, like you get like little badge showing you actually help people get jobs and people will put you on their advisory board. It's an awesome platform. I can't speak enough. And then Daniel Raul, especially, he is super open to talking to veterans and people that use the platform. He's the CEO. And so like, I've just been blown away like me and him met in real life just from that interaction and stuff. So I thought that was super cool as well.

Brock Briggs  33:58  

Maybe we'll need to see if we can get him on the pod. 

Tim McCarthy


Nate Lenahan  34:02  

You should. You should totally try. Yeah.

Brock Briggs


Brock Briggs  34:05  

So you get your MBA, you start doing some things you have mentioned before we started recording, that you actually worked at WeWork for a little while. I would love to hear about your experience working there. And any commentary on like the blow up that you might have.

Nate Lenahan  34:24  

Yeah, it's I mean, I was on the most unbelievable career experience I've ever had. And I mean that, in a completely positive way. It was, I joined not really knowing what it was. I don't think anyone really knew what it was, except for, you know, like a small core in the actual company at the time. But I joined as the head of operations for the Southern US. I probably never should have got that job based on what I knew. Like, I just remember one of my last interviews. I was very particular about trying to figure out, “Hey, what is the next interviewer looking for if this one goes well?”

And I just remember the last one I got. Everyone's always looking for culture to see if you're gonna be in addition to that piece. So I get that. But he was the global head of operations. And he was just like, always looking for his P&L Management. And I'm like, well, technically, I've never even managed a P&L. So like, I have my own business and like, maybe a little bit. And so I made my own P&L and brought it into the interview. Because I was like, this is what he's got to check off, I'm gonna check this bad boy off. I am getting this job. And so he had been a senior executive at Starwood Capital before that. And he's like, “Damn, man. I've been doing this for like, 25 years. I've never had anyone bring a P&L and to interview.” He's like, “I'm blown away. This is awesome. I love it.” 

And it was actually supposed to have one more interview with one of the C-suite. And he's like, “Yeah, I'm just gonna go ahead. And I'm gonna go ahead and cancel that. And I think we'll figure something out here.” And so I got the job. From the time I applied to the time I started with, like, seven days. And man, it was just like, everything you would think it is. You know, I got promoted probably every nine months or so from that point on. And I think that was really, really key. But we started with, shoot, my team had like three people when I started. 

And when I left, three years later, it was probably 350ish, 400. I like, and those numbers are a little skewed based on like, who directly reports in and then like, geographically, who I'm responsible for, even if it's indirect, and like dotted line versus, like, crap. But you know, I ended up being like the regional GM for all the Mountain West, so like Utah, Nevada, Arizona, Texas. And I launched I don't know, like 13,14 different cities and markets, you know, 5 million to about 220 million run rate and revenue over three years. 

So just it felt like I got to do a startup with a startup and the culture was incredible. The people were incredible. Did I ever spend time with Adam Newman? That's usually the question like, tell me about Adam. You know, what's your experience there? And like, I spent a few times with him. One on one? I don't think I've ever spent time with him one on one, honestly. He's always with like other GMs, like, or with my boss. And so. 

But my favorite Adam quote was, I live in the DFW area. And we worked, focus was always on the central business district. So they went into a city, very much like New York. And they're like, “Downtown, baby. I want to be downtown, like right in the mix of stuff.” And that's what they want. And so I was like, “Yeah, that doesn't work in Dallas, and seven and a half million people in Dallas. And just to give you an idea, 10,000 people of that seven and a half million live in downtown Dallas. So like, there's no density there.” 

Brock Briggs


Nate Lenahan

Nothing, right? And so I was pushing, like our GM at the time was, he was based out of New York. And he was incredible. But I was pushing to go to Plano, which is like, it's kind of North Dallas. It's the suburbs a bit for sure. But like, that's where all the professionals and all the entrepreneurs and a lot of them were based out of. And so he comes down and he's like, touring real estate with my GM and everything. And we're like “Plano, Plano, Plano.” He's like, “What? Where the F is Pluto? Like, what is this you're talking about?” And so that's like, my favorite Adam Newman quote is just being part of that. 

But I will tell you, here's my best experience, military related. I got activated for hurricane Harvey. The very first day I got promoted to GM of Texas. And so the day I supposed to take over, I just gotten a new boss. All these things I got activated for hurricane Harvey. And I told you about him trying to, like control the situation for a minute, like, “When are you gonna be back?” and all that stuff. And I gave him my priorities like, “Hey, priorities, mission first and family then work.”

And the best part of that was like, I've never been recognized or just kind of being me. And the best part of this was I went away for that came back. I think it was around like three weeks, something like that. So I came back, and like they were really excited about that experience. 

And so and then I took my, we created a little trip for WeWork employees. And we actually, I took like, 30 people down to Houston. And we actually gave back and like just community service, which was really, really cool. And so after that, they invited me and my whole family up to New York City to actually speak in front of a whole company on an all company meeting right between Adam Newman and Miguel like the two co-founders. And so that was the most like intimate experience like that, was I got to speak to the whole company, talk about hurricane Harvey, tell some fat jokes and you know, just share my experience there. And we just got recognized for being me. And it was the most incredible experience ever. 

Like we showed up at the hotel and there was gifts they found out the ages of my kids. They had left gifts, their handwritten notes you know. They like took us to Broadway plays like just like showed us New York City the best way. And I am always be grateful for that. So was there excess and craziness and all that stuff? Of course there was. There's all kinds of craziness. But the further away you are from New York, the less you kind of experienced it I think a little bit and felt it. 

And we were very very goal oriented on getting to cashflow positive, which was supposed to happen. Like even when I was there years ago, it was planned for 2021 for Texas, you know. And that was what we were planning on. So that's my quick and dirty on New York.

Tim McCarthy  40:12  

Good. So you were working on your own personal business and working for WeWork at the same time?

Nate Lenahan  40:20  

Kind of, we had already received multiple offers to buy our company. And so we had gone under contract, and I had two partners. And so they, I kind of got pulled in New York first. And they kind of closed out the business as it was sold, and wrapped that up. And then they actually both join me at WeWork, eventually.

Tim McCarthy  40:40  

Oh, cool. I got you. 

Nate Lenahan

Yeah. Yeah.

Brock Briggs  40:44  

As somebody that was in charged of that large of a section, what was your personal strategy in carrying out the company's mission? And maybe what were your big takeaways from, I guess implementing at that large of a scale?

Nate Lenahan  41:04  

Like a lot of us learned along the way. But you know, at the end of the day, like, connecting with your people, you know. So like giving them clarity is one of the most important things you can do. You can hear, like, you hear all the time, “Hey, you gotta communicate effectively.” Well, what does that even mean? What does that mean? Like, how do you know you're communicating effectively? 

And so here's a couple of ways that I tested that and try to assess whether we are being successful or not. So the last year I was there, I wanted one goal. I wanted one goal that everybody knew about, and they knew their contribution to it. And so someone had like, thrown out an idea of like, “Hey, do a hashtag, make it so simple. It can be a hashtag.” And we did, it was 86%, hashtag 86%. 

And all that meant was we want 86% physical occupancy, average, across all our buildings in Texas, well and Mountain West. So I had two different regions, Mountain West and Texas. But that was it. And I could tell you, you know, the feedback I got from both my team and others was, “Hey, that was the most consistent message we'd seen anywhere else, you know.” 

And so I remember this, there's this lady, she's a leader in Seattle. And she had reached out and she had actually checked in with different she's trying to figure out how to set up her own kind of strategy and communication for goals for her team. So she reached out to all these regions, trying to figure out who said the most consistent thing about their region. And mine, our you know, our Texas Mountain West region, by far was the most consistent. They knew what the goal was. And they knew how they contributed to it. 

And I think that's the most important thing is how do you give them enough information that they can run and make great decisions, even if we're not there? You know, and I think at the end of the day, you have that Northstar, so that was our Northstar 86%. And helping them and then like, of course, like, I was always visiting. I was always traveling. And then I was making sure that our leaders, anyone I was hiring, understood the culture in a way that they could hire more people that would embody it and add to it.

So at the end of the day, I think it's just really, really clear, consistent communication, and then a ton of transparency. So I did a town halls in every city, quarterly. And I am a no ego like no bullshit, like you ask the question, if I can legally answer it, I will. And I'm going to tell you the no bullshit answer, even if that means your job to be at risk. I'm just gonna like, that's how it's gonna be. And so like, that's the transparency I'm looking to build in my own companies. 

As a quick example, I'm literally writing a job description, like a job posting. And I'm sitting here wondering, like, “Why the hell don't job postings have what the interview process is gonna be salary ranges, you know? Like, what are the actual goals of the crap you're gonna do here?” Like, hey, “I need you to take us from one to $2 million dollars in revenue this next year. That's the goal.” Like they should know that in the job description. I think job posting, just like that's how transparent we're trying to get to. 

So that's it. I'm pretty simple, like very transparent. Answer any questions and then empower, empower, empower for people to make decisions and failures and mistakes along the way. As long as they learn from it and don't make the same mistake over and over and over again, man. I'm a happy guy.

Brock Briggs  44:18  

Why do you think that job postings and the hiring process right now is not that way?

Nate Lenahan  44:25  

People are afraid, man. Like they, employers have had the upper hand for so long. And right now it is an employee market. It is like, I saw this headline I thought was perfect. It said “the war for talent is over. The talent has won.” And I just loved that. But because like people haven't had to do it, why would they? You know, like, why would they? You know, in Colorado, for instance, you have to show salary ranges so people actually avoid posting jobs in Colorado companies, avoid posting jobs in Colorado. They'll say remote except for Colorado just so they don't have to post salary jobs. 

You know, so it's just crazy on people. But I can tell you, if you're willing to do it, man, you're gonna win. Like, again, it's kind of like, this is my competition. You know, you're doing it the same way you did 30 years ago, like, I don't even have to pay more. I'll just be transparent. I'll empower my people. And we also believe in this thing called a Tour of Duty, which, as a military, we know very well, right? There's this great book from Reid Hoffman from LinkedIn. It's called The Alliance, between employers and employees. And he talks about tours of duty. And it just spoke to me of like, “Hey, 18 to 24 months, this is what we're expecting you to do. Here's what you get out of it. Here's what we get out of it.” 

And so that's basically what we're doing because I want to take the job posting and basically say, when they start, you knew exactly what you're getting into day one, for 60 days. You're not getting anywhere. And you're not doing what you're supposed to like, it's an easy conversation for me to say, like, “Hey, this isn't working out.”

Brock Briggs  45:52  


Nate Lenahan  45:53  

Or if it is, it's going great.

Brock Briggs  45:56  

Well, and it's easy when that's all like laid out there. Like you said, you can you're directly measurable like to the higher ups like as from the employee perspective. But then you also know where you are, like, if you're making progress, like, “Hey, this was told to me on day one. My sole objective is to get to this. And if I'm, if we're going the other direction, you should know right away, like a really the feedback loop there is really, really short.” 

Not the exact same example. But I'm reminded of, I don't know if you've read the book Made in America by Sam Walton, where he talks about the, it's the story of how Walmart came to be. And he talks about, like, how he incentivized his employees. And it was, he gave them all like stock in the company. So he aligned the long term objectives of the company with like their individual mission, but then also made the sales goals transparent. It wasn't something like the executives are the only ones that see it. It's literally the stock boy in the back, that's making 25 cents an hour or whatever. Like he knows, we as a store need to meet this objective. And like my compensation is directly tied to that. So it's not the exact same thing. But I think that that's a really powerful thing of like aligned incentives. And getting everybody on one page, everybody from the top to the bottom knows what's happening.

Nate Lenahan  47:25  

Incentives are so hard. I will be honest with you. Like I thought, Man incentives are hard. All I know is I've rolled over 30 incentive plans. And it is really hard to get the behavior you're looking for from incentives, even though it seems straightforward. But to your point, aligned incentives are one of the most powerful things you can ever get right.

Tim McCarthy  47:43  

It almost reminds me of like, like a sleazy car dealership, when it comes to like job like trying to find a job, like when they don't tell you salary. And it reminds me of like, for the best price, click here. And then you have to put your information in and you got somebody calling you five times a day. And it's like, if you just like told me the price of this truck, like I would probably, like, come down and see it or like call you it. It sounds like you've seen a massive return and just being super transparent on your ads. Is that, would you say you agree?

Nate Lenahan  48:21  

I mean, this was gonna be the first one, I actually go this deep, like this. I mean, I just literally, I write, I try and journal every day and write something down. And this popped in my head Saturday or Friday night, I think. And we're writing this job posting. So this will be the first time we're actually post like, “Hey, here's the interview process.” I want anyone that actually interviews. If you actually, if you meet with anyone on Zoom, like anything face to face, and you don't get the job, you will get feedback. 

Even if it's one line, even if it’s one sentence like you know something, right? Like, I believe people deserve that. But salary will be posted. Your goals will be posted. What you get out of this will be posted. What we get out of this will be posted. And like the kind of timeframe we're thinking about this before we renegotiate the next like or like, set the next tour of duty because I've done lots of growth plans. Like I really, really care about my people. 

And I've done these personal growth plans. I've built my own template, like I build this whole process. And what I've always found is I'm really good at getting going. And really, really bad at following up. We're having a time bound, like it's any goal without a date is a dream, basically. Or any plan without a date is dream. And so it just became these dreams for all these people where weren't following up. And so that's why I like this idea of a tour of duty so much is because tour duties are known to be 18 to 24 months. Or whatever, you know, like you can say that. But if I'm saying that upfront, a tour of duty doesn't mean a title change. It doesn't mean you're getting promoted. Necessarily like 40% of time probably you'll have a promotion or title change, but I just love the time bound piece of that. 

And I just want to have that transparency from day one. So they can expect that from day one. Then that is the expectation hopefully that they're going to carry for their people. And how they drive the culture and the future through the whole organization. And I think that is just gonna be powerful.

Brock Briggs  50:09  

I couldn't agree more, like I've nothing else to say about that, because that literally just hits home. So, so strong. And I think that it's very easy as an employee, especially in a large organization to be disgruntled by a lot of things that very easily could be transparent. Why didn't I get that promotion? Why am I not being paid more? You know, those are probably the two big ones. But..

Tim McCarthy  50:37  

It's like you get lost in the shuffle. You know, especially in a big business. Yeah, like, just like you said, there's so many people that you're like, “Wait, why is this happening? Or, what is the overall goal?” You're just like, “What am I here for, to a certain degree?”

Nate Lenahan  50:56  

They get protected too, so like, if I was Zillow now and I'm posting, “Hey, VP of sales. I need you to get us from 25 million to 30 million.” Like that's, that might be numbers that they don't want to share now, like because of for whatever reason, which I can get that. But like, also, what the hell's that gonna change? I don't really, I just believe that there's far fewer things that actually matter as far as discretion than don't like

And if you're building that transparency and understanding along the way, then the people will. The people that are attracted to it are just going to be incredible and grateful. And they're gonna give you more than anybody else. And so, you know, we'll see how it goes. It's an experiment. Let's see if it blows up in my face. I bet we made some good changes here, though.

Brock Briggs  51:40  

I bet you that you do. And worst case scenario, it's a learning experience. Right?

Nate Lenahan  51:47  

Absolutely. Absolutely. 

Brock Briggs  51:51  

Invaluable. Cool. So we're up through WeWork and we've started talking a little bit about you looking to buy businesses, starting your own thing, kind of bring us up to speed with what your thought process about buying businesses. Kind of give us the rundown? Part of the reason I had reached out to you, you have like a really awesome Twitter thread on like losing a bunch of money. I don't know if that's part of that. But I think all of those things would be good to hear about.

Nate Lenahan  52:22  

Yeah, so at WeWork, actually bought a business. I bought it with my twin brother. And this is yeah, this is not one of the winners. This is one that blew up in our face pretty significantly. But you know, the whole premise was, from my MBA. I didn't realize you can just go out and buy like a small business, you know. And like, there's like brokerage websites out there. You're just, you get on and just like you'd buy real estate and find businesses that you're interested in. You ask for information or do financials, so you get to like biz, buy and sell, or you get to like quiet like brokerage or there's a ton of microacquire.com. 

And so there's all these great way to buy businesses now. And so I've just been fascinated with that and my brother came with a business that he just thought we could crush. Because his background is he was an Army mechanic in the Army, or obviously Army mechanic. But he was a heavy, heavy wheeled diesel mechanic with the Army. And so he's been in fleet maintenance. He's been running like big rigs and shops and maintenance for large construction companies or trucking companies. And he's very, very good at what he does. 

And so he came across this diesel repair shop and fleet maintenance company. And we just thought it’s gonna be great. You know, ultimately, we moved fast on it. We moved too fast to go do like SBA loan. He was pressuring me. And I was very supportive, because he's very good at what he does. So, you know, ultimately, we pushed through due diligence too fast. The seller was better at hiding things. And we're at finding things. 

And ultimately, we got in this business and it's pretty good. Like, we got it for a decent price had lots of revenue, and we were doing probably 100k a month. But we had not come in properly capitalized either, because I think we would have really weathered the storm better if we’d come in with the right capital. And then we load ourself up on like, retail debt. I'd say where, you know, 12 to 15% interest at the time we were gonna refinance. We had all these great intentions, but anyways, like we found out that this guy had been stealing from his customers. 

And so my brother, you know, we were just not gonna do it, like put up with that. So we went to the customer and we let them know. We managed to overcome that. And then he was trying to steal the employees and like non compete and both those things. So we kind of were dealing with those things. We built the loyalty. We treated our guys really well. So he kind of overcame those things. 

But then in the end, he had kind of falsified beliefs and in a way that could change dates and so we thought we had three years on this, the least, where we're at. You know, you figure diesel repair shop, you need a shop. You got to actually have a shop with bays. And, so we thought things are going really good. 

And then the owner of the building reached out and said, “Hey, you just get to know us.” And we were having a good conversation, great relationship. And ultimately, he was like, “Hey, my family's putting a lot of pressure on me. We think we want to sell. We're gonna sell to the main tenant of this place.” And we're like, “Oh, you need to give us time. Like all this stuff. Like we have at least three years.” He's like, “No, you have 30-day notice. That's it, you're on month to month.” And so we just basically crapped our pants on that was like, “Okay, why are the documents not lining up?” 

And so we went through the whole kind of review of documents and all that stuff. And yeah, they didn't match up. So ultimately, we were on a month to month. He gave us their 30 days notice. And as soon as we informed our largest customers, they basically bailed. They're like, “Hey, we're not gonna put up with this anymore. We're just gonna move to another week to a competitor.” 

And at that point, you know, my brother hadn't taken any money, or made any money for those several months. And you know, the pressure of his family, and you know, all those things, he decided to bail out. And I was still working full time and we work. So like, this is always a part time thing for me. I was always just like, I thought it was mostly just the money. 

And, let us, you know, not do things right. If I'm honest, it's like, it's completely on me. I'd love to just say it's all on this unscrupulous like seller, but it's on me. It's on my brother, like, we failed. We didn't do things we should have. And, we paid for it. So I think I lost over 150k on that one, you know, most of my cash life savings was gone. That one really, really, really hurt. 

And I took a huge I mean, this is the worst part, like I took a huge hit credibility wise. My wife and his wife, I mean, pretty much despise me at this point, like, will politely deal with me. And that's about it, you know. And so that is, that's the downside, you know, like, that's a crappy piece. That's why like, people tell you don't do business with family. But to tell you what, like, my brother is awesome. And I would invest in him again. 

In a second as an individual, like, maybe his whole family situation would not suggest me doing that. But like, he is very good at what he does. And so I do it again. It's like, I love that guy. We're still super close. It shouldn’t get in the way. So that's the crappy version. That's what happens when you get it wrong.

Tim McCarthy  57:27  

So you said something there that I think is super powerful. And it says a lot about you as a leader is, “It was my fault.” Like, despite this seller lying to you and falsifying paperwork and all this stuff, you're taking ownership of it, which I think is, that's massive for a leader just in life, right? It’s like, it's my fault, like I should have looked into it. So like I said, that says a lot about you as a leader. My question is, is that normal? Like when you're starting out and you’re buying businesses? Do you have to, like really dive in? Or is that like an everyday thing? 

Brock Briggs  58:11  

Like, literally everything went wrong.

Tim McCarthy


Nate Lenahan  58:17  

Yeah, I mean due diligence wise, I mean, and that's the hard part is, like, I know better on some of this stuff, you know. And we just moved so fast. You get so excited. You see the joy. And you're like your sibling who's one of your best friends, you know, and like, that caught up. And I didn't have enough time and energy to do it right. And that's on me. But like, for real estate, as an example, you'll get something, I believe it's called an estoppel. You go get that sign. And it's basically verifying the validity of the lease terms with the landlord to say like, “Hey, this business being sold. Ownership and responsibility for the lease terms are being passed to a new entity, which is essentially a sublease. Is this all good?” 

And shame on me, like shame on me. I have a real estate background. That one is absolutely on me, you know. And so but yes, due diligence is, it is an art. It is what it is. Because at the end of the day, like you can kill every deal you want to do due diligence, every one of them, you know. So you have to figure out what level of risk you want to assume. So like, for instance, we just bought, I bought another business recently with my two friends that I did the property management company with. 

And, you know, like, the guy's like a blue collar guy. He knows his business incredibly well. But he doesn't have all the reports and all the financials the way that may be a more sophisticated buyer. Or like a finance background person might want where it's like, “Oh, I need to see it. I need to see this view of it. And it needs to be this way. And I want these 15 different reports.” 

And this is gonna tell you, I gave you the fiber reports is all you're getting. If you want more, then I'm just gonna go to this other buyer. What do you want to do? You know, and like, so it really is an art of like, how much do you press and how much risk are you willing to take on. So I learned a lot on getting that wrong for, with my brother, and more so about making sure we had an acceptable level of risk for this new business that we bought.

Brock Briggs  1:00:12  

That's a very powerful lesson there, that's for sure. 

Nate Lenahan


Brock Briggs

I think that buying businesses like this in this format is something that's drastically under followed and not talked about enough. We have like really the glamorized, like entrepreneurship, like, oh, I'm going to, especially you work at WeWork, like anything in the tech industry is like, “Oh, I'm gonna do this startup. I'm gonna go raise all this money and like, do this fancy thing.” But like, there are so many, like small and medium sized businesses that are run by older people that are looking to retire, maybe. I don't know if that was the case with any of yours. 

But a lot of people that just, and especially that aren't running their businesses in the most efficient way possible. You know, they're still running stuff on fax, and it's not electronic. There's all these opportunities to kind of optimize businesses and whatnot. So I think that it's cool that you're doing that. And people should be aware that that's an option, career wise. 

And you mentioned a couple of the places that you look for businesses that are for sale. Well, could you talk a little bit about the money involved? You said that you move too quick for an SBA, a small business loan. I don't know what the exact, Small Business Administration, I think. 

Nate Lenahan

Yeah, exactly.

Brock Briggs

I don't know what the timeframe for those loans is. Could you talk a little bit about that? Talk about what you guys did. And maybe some differences, pros, cons of each. 

Nate Lenahan  1:01:48

Yeah, I think, okay, so I can give you my brother as an example and the new company. So my brother's example. I don't know if we could use SBA or not actually. I'm trying to remember some of the constraints on that. I've honestly kind of lucked out. A little bit of that I was texting my brother because I did share that. I shared like a Twitter thread about it. Because everything's glam on Twitter. And I was like, “Okay, this isn't real life.” And so I was like, texting my brother, like, remind me what, like, what was this or what happened here and on some of the things and so because he lit like, he truly lit it. And I was, I felt like I was more than the audience in a lot of ways. 

Because I had, we work still full time, which is just like all consuming in itself. But I don't know if that business had been around long enough for us to use SBA. So for anyone that doesn't know SBA, Small Business Administration is a federal entity that helps provide underwriting criteria basically, to let people buy businesses. So you can buy businesses for less money down than you normally would expect. 

So for instance, like 10% is about is pretty normal through SBA versus if you just went through a bank. They're gonna expect 20 to 40% down. So that's the difference. SBA, and so they back you and they give, again, a government guarantee behind that loan. So if you default, the bank still gets its money. So that's the beauty of SBA. 

So we end up doing like, man, we did, like all the worst thing you could do. We got like personal unsecured loans, and like, 12%. We were just as creative as possible to get this thing done. Because we figured, “Hey, if we move fast enough on it, we'll get it done. And then we'll just refinance out, you know, 90 days in, 120 days in, get like much better financing.” Well, it turns out, like we made it about 120 days, and then we fire sell the company, basically. Because that's when I blew up. So that's that one, like didn't quite make it. 

So the new one we did buy, we bought it for 400k. We put $55,000 in all together. So 55k being for the loan itself. And then we also got 100k line of credit. So ended up being like a, you know, $355,000 loan, or no, she made $405,000 loan between the line of credit and the actual loan. And then we put our down payment. And so not bad for buying a business that has over a million in revenue. 

And we put in 55k, you know, so that's what we got. And to your point, he was retiring. The owner was retiring. This is an HVAC business in North Fort Worth. And to your point like over the next, I think 10 or 15 years, there's gonna be a $9 trillion transfer of wealth of baby boomer businesses either being sold or are given away or just dissolved because they don't want to do business anymore. So incredible opportunity over the next decade to kind of be an acquisition entrepreneur, if you will.

Brock Briggs  1:04:49  

Yeah, that's really incredible. And like I said, I think something that's drastically under talked about and maybe less glamorous. But when you think about the amount of risk that's involved, I mean, you highlighted some of the very large risks when it comes to due diligence. But when you're talking about a business that you can physically see, you walk into it, we see that they're already doing a million dollars in revenue. They 've already got traction. And it's up to you to kind of scale or maybe you just maintain it. You just take it over and whatever. Can you talk about why you think that maybe you're uniquely equipped, or why somebody would be uniquely equipped to buy rather than maybe start their own business?

Nate Lenahan  1:05:36  

Yeah, I mean, this is some soul searching. And it's, I think my ego pops up a little more often that like, and like my own self discovery in this journey. But because I want to say like, “Oh, I'm an entrepreneur. I'm a zero to one kind of guy. And I can do that.” But I'm not as good at that as I am at making something better. You know, and so like, I think that's a realization, like, I am much better coming in assessing something, and knowing exactly which levers to pull to make it better to double it, or triple it, or whatever. 

And really go, you know, where we need to go. And so, versus zero to one, like, you're starting from absolute scratch, you know. So from like, setting up email to building the website to, you know, answering every phone call, figuring out how you answer phone calls, like, that's just harder. It takes a lot of energy to get to that million dollars range first. So, you know, for some people, I think the right question is like, why? Why would I do that when I could go buy something that already has a million dollars in revenue? And just learn it from someone who's already done it, and then build on top of that, from what I know, you know. So like, I know, I have plenty to offer as far as leadership and operations. I'm an operator, that's who I am. 

And then like very, very customer oriented, you know. So between those two things, those three things, and then like technology, I love technology, I swear half the reason I want to buy companies is just go see all the cool tech and SAS products and stuff out there to make things more efficient. But that is, I think, a huge opportunity for people. So do you want to start from scratch and do every little thing until you can hire someone else and have revenue? Or would you rather buy a business that's large enough that you could have a general manager and you're really just guiding it, overall, as you learn the business and pay off the debt?

Tim McCarthy  1:07:19  

I feel like this is like got me super excited. And this is exactly why Brock and I wanted to do this podcast in. Part of it might just be because I'm an idiot. I didn't realize you could literally take out a loan to acquire a business like that. That's crazy to me. So if somebody gets out, and they're like, “No, I think buying a business is way more appealing. I think I have the skill for it.” Where do you start? And how much capital are we talking for an average business? I know you said 10% with an SBA loan. I mean, what's the first move? And on average, like how much coin are we talking?

Nate Lenahan  1:08:04  

Okay, so I mean, lots of lots of “it depends” answers there. But..

Tim McCarthy


Nate Lenahan

I can give you some rough guidance. Okay, so a couple, I'll give you a couple of quick shout outs too. So if you guys like veterans who are doing, like buying businesses or doing cool things like that, if you're not following, I believe it's @SamtLeslie. He's awesome. He's also bought a plumbing and HVAC company in Colorado. And then there's Rich, I believe it's Rich Jordan. He's also, so Sam was an Army officer. Rich was a Marine Corps officer. 

And they just, they're always dropping great knowledge. But they also have bought businesses. And they're buying even more right now. And it just goes to show military veterans are people that people want to invest in. Okay, and then there's a whole movement here called Search Funding. So you can go to searchfunder.com. These are literally people that there's two types of searches. There's a self funded search, and then there's a funded search. 

And mostly this came out of like, I think Stanford, where it's basically all these MBAs and trying to figure out other alternatives to investment baking, or consulting, or like, what's another career path outside of like a prestigious MBA. And so this idea of a search fund came out where there's investment companies out there that will invest in you, you know, Tim, per se, and give you $250,000, to search for two years for business. And then when you buy that business, they will invest in the business as well, to let you actually acquire and then you'll run it as CEO. 

And they'll take, you know, they'll take what percent, you know, some percentage of it. And then you'll have some percentage of it. And like, that's what search funding is, you know. So there's opportunities where you don't necessarily have to, they would refer you, put some of your own capital in. But, you know, sometimes that's just really like, “Hey, whatever your net worth is, I want to see at least 30% in this business.” 

So other people might be like, “Hey, if you're not putting 100 grand, and I'm not interested,” you know. So that's search funding. There's so many resources, that's a great place to start. You get to like Stanford's search fund website or whatever. Search that and they have just everything you want to know. They have details and stats and all that stuff. So that's search funding. And then there's self funded search, where you're, it's exactly as it sounds like you just keep looking on your own. 

Ideally, you've quit your job, and you're full time searching for a business to acquire. Now, most of the time, these people are wanting like a million dollars in EBITDA. And which, on average, will put you around five to, let's say, five to $7 million in revenue. The limitations of SBA if you're to go that route, is 5 million in revenue. So like they only do loans for small businesses. And that is the threshold that they've established is five millions for an individual. That's how much of a loan they'll give you, doesn't mean you can't get a loan for a bigger business. 

But that's all the SBA will back. So you could get, you buy a $7 million business, 5 millions backed by the SBA. And then the other 2 million you have a bigger down payment on because it's not backed by the SBA. So there's all kinds of opportunities out there if you want to do this. But once you get like in that million EBITDA range, like the multiples of EBITDA, that's how they value companies. So like a million dollar EBITDA, a company would probably go for like 5 to 7 million, honestly. Depending maybe, maybe a little bit less, could be more. 

But then you start getting like these big institutional funds start to get interested at like the 2 million EBITDA, 3 million EBITDA. So just depends on like, how are they valued. We're gonna get loans for, an artist suggests to a veteran coming out. I'd be looking for something a little bit smaller, like, go find something that you could buy for, you know, with a million revenue. I'd say a million revenue is a great threshold, as long as it has like a 20% margin. Then you should be buying that for between 400 and probably 900,000. So that means you're putting in 50 to 100k. 

And, then you probably want another 50 to 100k in working capital. So you might fail to get the loan, like the line of credit we got was part of working capital, that's the whole reason they give it to us. And then they also gave us a loan for 37,000. And just like straight up cash working demo. So I gave him 55k in cash, and then they gave me 37k in cash right back to say, “Oh, here's your working capital.” So it's really great. 

And you'd be surprised at how many people are willing to fund these kinds of things. Because, man, there's great businesses out there, great businesses. Literally the first, I think the first week I was on Twitter, someone reached out and was like, “Hey, you're the kind of person and business I would love to invest in.” And I'm like, “I haven't even met you.” My only thread is the one where I just screwed up with my brother and lost 150k. So people love looking for good people that they like working with and they will invest.

Brock Briggs  1:12:58  

Not to get to Finance here, I know that you're an MBA. I have a Finance background. Can you give us like basic breakdown of like, how multiples work in that small, medium sized business? What is you know, you talked about EBITDA multiple. What are like acceptable ranges? Because I know that there are a lot of these businesses are they maybe have high capital expenditure requirements or high working capital, their physical properties. We're not talking software as a service or anything here. What kind of multiples should we be looking at when it comes to these businesses? And like what's reasonable? 

Nate Lenahan  1:13:41  

Yeah, I would say okay, let's just we'll hone in on like the home service businesses that's like plumbing, HVAC, electrical painting, like roofing whatever you want on a home service business. Frankly, most businesses that are this size, like anything around a million dollars in revenue, or less. Or even a little bit bigger, like you can expect kind of like a three to 5x range. So multiple is just a fancy way of saying like, “Hey, how much profit did you get EBITDA, like Earnings Before Interest, Taxes, Depreciation Amortization, if you make 100,000 in EBITDA every year?

What's my business worth? Well, it's worth three to five times that, depending on a lot of things. So like, the things that will contribute to it being a five versus a three would be, “Hey, we just grew 100% last year and we still managed to have 20% margins.” Well, that's damn impressive. Okay, I might be getting something even more valuable here and I just need to keep the momentum going. 

So I'd be willing to pay for maybe a four or four and a half or 5x. So that's all multiples are just whatever EBITDA  is. The other term you might hear as a replacement for EBITDA is SDE, Sellers Discretionary Earnings, which just basically means whoever owns the business right now, how much money did they have discretion to use? Like are they charging their brand new boat to the business and their brand new Escalade? And like, what discretion do they have? And when they say discretion, that means when the business passes over to you, you'd have that same amount of money. 

So if seller's discretionary earnings was $200,000, when we buy the business, I would expect to have $200,000. And then your multiple will be based off of that. So three to 5x. So anywhere from 600k, I buy this business to a million dollars. I buy this business, you know, and so it just depends on what your criteria is. Because at the end of the day, you the things that you'll be paying for that they didn't have to potentially is an SBA loan now, you know. And so you want to make sure you actually have cash after an SBA loan, because EBITDA does not include your loan payments. That's why, for a lot of people, it's not a term that they care about that much. They just want to know how much cash do I have, after all my bills. But for valuing a business, it's really important because when you sell that business, it's gonna pay off all the debt anyways, so like the debt doesn't matter. 

So it's just all about how much cash you have before the debt. So that’s it. SDE or EBITDA is how most small businesses are valued. And the one other opportunity that you have is, you can put your own money in. You can use other people's money. You can obviously use a bank loan, and then the seller themselves can also be a loan. So they can give you what's called Seller Financing where maybe they let you purchase a business and just pay them back over five years, or 10 years or some portion of that, you know. For instance, our HVAC business, I believe the seller gave us 10% of the business was Seller Financing. So he gave us an extra loan for $40,000 that would pay back over five years.

Brock Briggs  1:16:47  

And I think that depending on how creative you want to get with your structure of like the purchase, you probably could maybe get, like you said partial Seller Financing. If you were coming into this and said, “Hey, I want to buy a business, but I have no money.” You probably could arrange it to where the seller would give you financing for the 10% that you need to put down for the SBA loan. Can you do that?

Nate Lenahan  1:17:15  

They become a lot more strict on that. So to fulfill the downpayment for SBA, probably not. They usually require, they want to see cash in hand. They just want to see like a real effort there. It can help. A seller financing can help where you can actually get down to 5% down payment, and that's the cash you actually have to provide. So it just depends. You have to ask, those are the questions you got to ask. And this is why you talk to multiple lenders as well, because SBA loans are not bound to one bank. So you could talk to three different banks. 

And they actually have different criteria or offerings, you know. Like just negotiating, hey, “I'm willing to give you that million dollar loan for 5% interest rate over 10 years. And you only have to put 5% down.” But these guys, you know, bank number two, once you put 10% down at a 6% rate, like it just depends. 

So talk to multiple banks, talk to lots of people. Ask lots of questions. Go on searchfunder.com. It's a great place to like learn a lot and hear other people who are buying businesses. Follow SMB attorney on Twitter. The guy is freaking a rockstar. And he'll tell you he's been sharing, like a masterclass for buying businesses. What a great LOI, like Letter of Intent looks like, how to contract. He just gives out incredible advice. And so all the resources out there for you to be successful, if you want to be successful and are willing to put into words.

Brock Briggs  1:18:38  

Very cool. The last question that I have about the SMB purchases and whatnot, is you talked earlier about the things that you bring to the table. You're an operator. You've got the leadership, the tech savvy, all of these things that you're bringing to the table. And maybe you can talk about this with your most recent purchase. 

But what are the first things that you're doing after you buy this business? They hand over the keys, what are the first couple things that you are doing? And because I'm guessing they're going to be like how do we get more efficient fast? Like you know, you've already got this base.

To me, that's my first thought is, “Okay, let's not maybe worry about growing super fast right now. Let's just try and optimize where we're at.” Do you take that same approach? And or what other things are you doing right when you walk in?

Nate Lenahan  1:19:33  

Okay, I'm very cautiously optimistic about efficiency and growth. But I can tell you the most important thing is that people. Just go, you need to build trust and retain the people more than anything. That is the most important thing. So like screw the efficiency, screw everything else. If you don't keep the people then you don't have the business anymore. So, you know, at the end of the day, I'd say that's where you spent all your time. So that means you're in attics and freakin’ the summer of Texas. 

With your technicians, because you got two technicians and they bring in all the revenue for the company. Then that's where you're going to be. That's where I'm going to be. That's where you need to be, you know. For a little bit like show them that they can trust you. Show them that you're willing to put in the work that you're willing to listen. Because they have great ideas. They know more, they know far more about the business than you ever will, in so many ways. And so just listen. Learn what you can from them, build trust. 

And I think that's the most important thing you can do, right off. And then you're juggling also, the tremendous amount of administrative transitionary tasks. So like, you only get 30 days, usually with an owner. That is part of the deal. So like when you pay the price, you get 30 days of kind of free consulting. 

And I gotta tell you, like some of that stuff is just mind numbingly painful. I think we spent 20, I say we, it's mostly Scott, who's my partner. But he probably spent like 26 hours, just transitioning one phone line, to just poring over a number, trying to get a hold of one freaking phone number business line to our you know, for us to own it, you know. And then you figure, “Hey, like HVAC, these guys have, you have the brand of air conditioning that you sell. So that's for us is Carrier. So that one's relatively easy. And that's one account. But like all the supply houses, so use like 20 different supply houses based on where we are in DFW. 

So building an account with every single one of those and making sure that they know you and actually getting credit. And then signing over like the rest of the free game, phone numbers and the cell phones. And like we're still trying to figure out we have multiple iPhones that we own now that are work phones that have old Apple ID accounts that we can't get into and figure out. And so like they can't download the freakin’ new apps that we need them to download, because we want to be so efficient. 

And we can't do it because, you know, shitty processes before that, like we're having to deal with now. So yes, we have lots of processes that we're putting in place. But I will tell you the appetite for change, man, you have to have your thumb on that constantly, because you want to change everything and they don't want you to change anything, for the most part. 

I will tell you, our team, and they have been incredible. We have changed some things like I changed a website right away because we needed to. And then we're changing like our CRM type, like dispatching software, all that stuff as well. But we did that talking with the guys trying to figure out, “Hey, like, are you guys okay with this? Have you used this before? What's your appetite building trust first?” And they I believe I built into, like, our vision of where we're going. And they have been a part of building that vision too. Like, “Hey, that doesn't make any sense. Don't do that.” Okay, well, I like to share more of me, so I understand. So I tell you people first, people always. Like start with the people every single day. And that will take you very far. And then the people will help you with the efficiency. It's no longer just Brock going after efficiency. It's the people saying like, “Hey, have you ever thought about doing this?” And like, “Yeah, I have thought about doing that.” And I'm like, “Why don't you just do it then?” 

And so like, we're empowering the people to start making their changes. If you see an opportunity to do better, and that you can make it better tomorrow. Do it. Just do it. Let's see what we learn from it. And let us know so we can document the process but, just go for it. Like I don't know if I know better than you. So that's my piece on like, change management's hard. And it takes far. It takes two to three times longer than you ever think it's gonna.

Brock Briggs  1:23:31  

And just, this is probably something that I should have asked like, way before. Did you know anything about HVAC before this?

Nate Lenahan  1:23:38  

Yeah, so I mean, my whole background is like facility management, property management. So I've led skilled trades, plumbers, electricians, HVAC guys for years. And so like I'm dangerous enough to you know, to fix like, I can swap out a fan motor or change a capacitor or like, figure out maybe the very, very simple things. 

I could certainly learn the rest. Do I have a huge interest in learning all the rest? No, I have a huge interest in the guys trusting me and knowing that I'll work hard. Yes, but that’s just my piece. Do you need to? You don't need to know anything about it. It helps. It certainly helps with credibility and how fast you learn but if you're just showing that you're a servant leader, and you're willing to do anything to help your guys and gals and make them successful, and you actually care about them, and you listen to them, then you'll be fine.

Brock Briggs  1:24:29  

That stretches far beyond just this case. But it sounds like that's your rapport and like getting that early buy in is probably your most fundamental thing right out of the gate.

Nate Lenahan  1:24:43  

After because yeah, people aren't going anywhere or if they do, then you're not going to have much value left. Yeah, they've created it.

Brock Briggs  1:24:51  

Yeah. what is the end game look like for you? So it sounds like you've made multiple acquisitions. Are they all separate? Are they all kind of in the same home services space? What is five years look like from now for you?

Nate Lenahan  1:25:08  

We have, we just have one acquisition right now. So it's just the HVAC company. The one I do with my brother I sold, or we sold. But we're actually, we're in the process of trying to buy another company, a plumbing company, ideally. So trying to add the skilled trades. So plumbing, electrical and HVAC, that's what I consider the most skilled trades. So we're trying to get all those. 

But ultimately, we're actually building a tech company on top of that, called Homework. And that is like the big you know, swing for the fences idea that we're going after. And, like a really quick premise of that is basically how do we do either of you own homes? 

Tim McCarthy

Yeah, we both do. 

Nate Lenahan

Okay, you both on home. So have you in that pursuit of owning a home, have you ever wondered like, what am I supposed to be doing? You know, how often should I be changing air filters? Or should I be getting a tune up on my HVAC? Like right now? Or do you have to do that every year? Or what's up with that? Dude, I always forget to freakin’ put down the weed killer every year. And I got freakin’ weeds for days and all my grass and just wondering when that is or wondering, “Hey, like, what the hell is that? What's that paint color in my freakin’ office? I have no idea what that is.” 

And so the idea here is Homework, which is our company could solve that for you. Homework is meant to be the operating system for your home. And the idea being, we gather data about your home. And by doing that, then we're able to make home management easier for you. So instead of always worrying about homework, you get to worry about home life. 

And so that might look like hey, sending Tim a text saying, “Hey, Tim, are you ready for that, like walk barefoot in the grass this year? Well, if you are, just sign up for a subscription for, you know, for annual fertilizer, and we'll send it to you exactly when you're supposed to put it down. Or just click here and have us come do it for you. We'll come take care of it for you. Which one would you like to do?” 

And then another example would be, hey, the last time our guys came out to fix your HVAC, they took down your serial number, model number, all that stuff. And the next time you have a problem with it, you can just FaceTime with us, and we'll troubleshoot it with you over FaceTime. So we don't even have to come out, and maybe we fix it. Or if there's something wrong, we already know what you have. So I can give you a quote instantly on the phone say, like, “Hey, it's gonna be $9,800 to replace your whole system, furnace and outside unit. Does that sound interesting? Do you want to do that? Like, let's talk through it.” 

And then if you say yes, then it's one visit. And I have to come out one time. We've already talked about it. We're super transparent pricing. And so we're going to get, so it'll kind of have a timeline for everything that's ever happened in your house if you wanted to. So like, you could just text a number with an invoice from your plumbing company, and they'll just throw it in the timeline for you. You can share renovation photos in there on the timeline. All our companies will send our invoice to that portal for you. 

So it's, that will be our other hook of, if our HVAC company did service for us, like, “Hey, if you want all your history for your home gym, we sent your invoice in there. All the information needs to be in there along with everything else.” And so the more info you put in there, the easier life is. So that is the really quick and dirty on Homework.

Brock Briggs  1:28:25  

What a cool idea.

Tim McCarthy  1:28:26  

Yeah, that's a really cool idea.

Brock Briggs  1:28:28  

I imagine it's Carfax for your home. Like in addition to like, not only are you becoming a better homeowner, and like taking care of the the things that like you own, which I really resonate with, because if for whatever reason the person that I bought the or me and my fiance bought this home from is listening, fuck you. That like, you know, just they aren't taking care of you. 

It sounds like lived in Norfolk, which is where I live. And this area's just, it's beat, you know. Nobody takes care of their thing. They're in for a few years and then out. And so one not only is that cool, where you can, like, take better care of the things you own. If you're going to spend $300,000 on a home, you should probably take care of it. 

And then also, it's a plug for the business. You know, it plugs you in with somebody that's knowledgeable and isn't going to rip you off. And then I would imagine that would be so valuable on the backside to when you go to sell your home like, “Look, I have literally records and the company that did this work and like here's who we're responsible for it and like, that's so cool.”

Nate Lenahan  1:29:40  

I love that you love it. So we're working on the tech side of that right now and hope to shoot out our beta users like MVP in March, by early March. Hopefully late February but trying to get the first testers of it and see how it goes. We've tested a lot of different pieces of it kind of through the HVAC company but really excited for that. Let's see how it goes. 

Brock Briggs

Pretty cool

Tim McCarthy  1:30:05  

Yeah, I really liked that. If I could just like get a text message like, “Hey, Tim, you need to change your filter. Or, you know, it's April you need to fertilize your lawn.” I'm like a big, I like just, I feel like I'm so busy all the time that like I have a company that comes in like error rates my lawn and like puts fertilizer down and it just be so that's so convenient to just be like, “Oh yeah, that's like just book that. Perfect.” And then move on about my day. I really liked that.

Nate Lenahan  1:30:36  

That's the premise man. One of our other hooks on that is we are going to invite. I don't know how many people can do it because it's a little expensive. But I know the first 100 users, we're gonna give you a free 3D model of your own. 

Tim McCarthy


Nate Lenahan

So like, it'll literally like you just go out and take a picture of your home. And our partner will put together a full 3D model where you can change the roofing and the siding and the brick and like all that stuff. So that's what you get. What I get as the company is I get all the measurements. I get everything. So I could tell you if you wanted like some of those sexy, have you ever seen like the sexy new kind of like black outline windows? Black framed windows these days are, they're great looking new homes. 

And if wanted some of those like I could quote you right there in the portal to say, “Hey, it's gonna cost you like 18 grand to replace those, you know. Is that something you're interested in? Would you like financing when you want to do it? Let's go.” You know and you never even had to come like leave your house or get us hard sales pitch because all windows sales is gonna be a hard sales bridge pretty much. Like as soon as you let them pass that front door, you know, you're gonna get the hard pitch. And so I don't know, that's, we're fascinated with how do we make this easier for people really empower you to be better homeowners and like living better lives through homeownership.

Tim McCarthy  1:31:53  

Once this company blows up, I may need to keep my wife off of that, because I could just see every month like, “Babe, look what our house would look like with a black roof.”

Brock Briggs  1:32:07  

That’s your target market.

Tim McCarthy  1:32:09  

Yes, absolutely.

Nate Lenahan  1:32:11  

Engagement, man! Got to have something that keeps them engaged. But imagine to your point, Brock, being able to have kind of like a buyer's portal where you can look at a house and like figuring out, “Hey, how much would it cost me to replace this roof and change out the H back and fix this because I walked through and that like that whole foundation, or the pier and beam in that room is shit. So I need to fix that and have like, at least ballparks of what it would cost for a house.” So..

Brock Briggs  1:32:41  

Just to kind of like start to close out here. What are some big learnings and maybe some big struggles that you've had, maybe before or still as a veteran and just kind of the professional space? What are your big takeaways since your exit that other people would learn from and then maybe what's something that you're still struggling with?

Nate Lenahan  1:33:07  

Yeah, I think there's this interesting dynamic of I don't know the right word for it. I don't want to say entitlement, but it feels a little bit like entitlement. Like I'm a veteran, help me, you know. I deserve help, you know, give me that job. Give me that chance. And I think that service members really need to let go of that. I think that was one of my bigger learnings of like, people don't really care. They just don't. And I don't mean that in like a really bad way. I just mean that people have so much to worry about themselves, you know. And everyone's going through their life where they're the main character, not Brock, the veteran or Tim, the veteran or Nate, the veteran, right? 

You know, and if you think about that, if everyone's the lead character of their own life in their own story, then, you know, it's so like, it's so impressive when others are willing to give their time to help others, right? And I think you use the veteran piece as much as you can. And what I've learned is it will get you mostly people willing to have a conversation. That's about the only thing that I've found it to be super valuable on, of, “Hey, I'm a veteran.” Or “I noticed you’re a vet. I’m a vet too. Can I get a combo, kind of get like my foot in the door a little bit?” 

And so I think for anyone that thinks they're gonna get a job, because they were, you know, an E-7, E-8 or 0-4 and they were in the military, and they're just gonna get a great job. Like, I think that has been, I've learned over and over and over again, that is not true. That's not true. Like, they don't really care. They say they care, but they don't really care. And the best example I'll give you, luck loves their veterans. And I absolutely believe that. 

But I went up for promotion for a manager job one time. And they did not count any of my leadership experience from the military as leadership experience. And that just goes to show that like, I mean, what? I mean, I don't even know how to respond to that if I'm honest, like it was the most angry I ever was at that company. 

And so, you know, people don't care as much as you think they would on that. The other piece is like, there's so many great things you learn in the military that you don't realize. There's this concept that I love. I think Amazon kind of has pioneered it, but it's called Disagree, Commit. And think about all the orders you gotten in the Navy, or that you did not agree with, you know. Not ethically, like, ethically, that's a different thing, right? That's, you have the moral courage to stand up to that. 

But there's plenty of stuff I was told to do that was like, “This is bullshit. Like, I don't want to do this,” but I did it anyways, right? And I did it because I was supposed to. And then you go out in the real world, or in the civilian world, and you're just like, “Man, I got to actually, like, put my input in sometimes. And they still didn't agree with me, but I'm just glad someone listened to me in the first place,” you know, and so I love that. And I love sharing that with my team. Like, I always want to hear their ideas. The idea that I have all the answers, man, like, you're wrong. I'm wrong. I don't have all the answers. 

But I do make it very clear for people like who has the decision, who gets to make the decision, because I'll say, “Guys, it's my decision at the end. We may all disagree here, and I'm so grateful for that. But at the end of the day, I gotta make the call. Because this is my call. If it's your call, and we disagree, you get to make the call, great. I'm not getting mad about that. No, you go, like, let's get this done. Let's get better tomorrow.” And so I think that's another one. 

And then lastly, like, find your community. Find people that you can talk to. Find people that make you feel great about who you are. And there's just nothing better than that. And so if that's, you know, like, I feel like I've found a little bit of one in the SMB world with Twitter. I'm blown away. I've been on there for like 75 days, and I can't believe how many people I've met from it, and how much it's impacted my life, but personally, and physically or business wise already. I did in college, those two of the people that are partners with me at the company are now both came from the football team that I worked for, from making that decision, you know, and so lifelong friends, hell yeah. 

So find your community, make those friends, and then just do it. Like freakin’ take the risk. Do the thing, you'll regret far more not taking the opportunity than taking the opportunity of failing because failure, man is meant to be embraced. It's just another word for learning. If you have the right attitude, and you know, I've already bought another business, even though I failed miserably the first time and it will not be the last time. And I would do it again with my brother in a second. Like, so I just say like, don't worry about failing. People love it, share just as happy as your biggest moments. And you'd be surprised at the people that flocked to you.

Brock Briggs  1:37:38  

That's all really, really, really good and very powerful. And then I guess something that maybe you're still struggling with, if you are struggling with anything and just kind of curious from like, a military aspect or not. 

Nate Lenahan  1:37:53  

Yeah, I would say that I mean, there's still the stigma. There's stigma out there on mental health. You know, and I wrote a post about this a long time ago on LinkedIn. And I just remember, like, I wake up sometimes feeling like there's a weight on my chest. Like there's like a sense, like, just an unbelievable sense of impending doom. And, like, I don't know how to overcome that all the time. 

And so the reason I shared that then was because the CEO of I worked for at the time, you know, she I think had articulated it better than I'd heard most people and she just said, “Hey, like, you gotta understand.” She is a classic founder. She is “go, go go.” She's incredible, but she has what she calls her down like cycles. And she's got to step away. She doesn't want to care about the details. She just is struggling to be present, and all those things. And so I have those same things where it's just like, I have this weight on my chest. I feel like there's just doom. I don't want to get out of bed. And then I do. 

And so like, at the end of the day, I hope you know, everyone here has a chance to make that decision and get out of bed and or whatever their version of that is. And talk to someone because there's nothing wrong with telling people that you're struggling or that you failed at something. Or that you hate your current situation and you want to make it better. So I just want you to know that it's not unique. There's far more people going through it than you think. And there's lots of people here to help you.

Tim McCarthy  1:39:26  

Good stuff. Absolutely.

Brock Briggs  1:39:33  

Yeah, I couldn't have said it better there. We were talking about it in our last interview. But there's not a lot of people other than other veterans that are really looking out for you. It’s kind of the sad part of it. A lot of surface and kind of political stuff banter out there. But, you know, really finding your community like you mentioned and being able to lean on those people when you need help in whatever fashion, I think that that's valuable. Tim, do you got anything else?

Tim McCarthy  1:40:08  

No, no, this has been awesome, super informative. Definitely an eye opener for me on, you know, buying businesses and that kind of thing. That's a really cool idea. Definitely something that I'm gonna personally look into. But other than that, no. Nate, I appreciate you coming on. Dude, this was a lot of fun. So thank you for taking the time out of your day.

Nate Lenahan  1:40:31  

Yeah, it's a privilege. Thank you so much for letting me just share a little bit of my story. And you can, by all means, send me a text. I'll do a call with you, whatever you want for..

Tim McCarthy


Nate Lenahan

Helping you look at businesses or even where to start. And I mean, I'm sure Brock's pretty, pretty smart on the Finance side, so I'm sure he can tell you the numbers and stuff. But yeah, happy to help anyway, again.

Tim McCarthy  1:40:50  

No, that's awesome, man. I really appreciate that.

Brock Briggs  1:40:53  

We're in, just real quick if people are interested, if they want to follow along with you, contact info, Twitter, your company's website, whatever you want to throw out there, people.

Nate Lenahan  1:41:03  

Yeah. All right, cool. Well, the main two, like social medias that I do is Twitter. I'm @n8lenahan. And Nate is spelled in the number eight, I have just so much street credit. So that's why, that's n8.

Brock Briggs  1:41:17  

Doesn't get harder than that.

Nate Lenahan  1:41:21  

And then I'm very active on LinkedIn, as well. So just trying to share stories about leadership and business and just give people a peek into what it takes to build something that you're proud of. And that gives you purpose and like driving motivation and in the failures along the way. So I'm an open book. If you ever want to reach out, have questions, I'll do my best to answer. I try to answer everything. But I'm human, and I listen too.

Brock Briggs  1:41:46  

Well, this has been fantastic. Nate, thank you so much for your time. 

Nate Lenahan

All right. Thanks so much, guys.