Ep. 187 – Smart City Locating COO, Nathan Lenahan

Our guest today is the COO of Smart City Locating, Nathan Lenahan.

Nathan Lenahan joined Smart City in January 2020. In his role as COO, Nathan drives vision and strategy at Smart City, cross-functionally leading departments such as Sales, Marketing, and Strategic Partnerships for the company.

Nathan garnered success in previous roles where he managed revenue portfolios of more than $200M, built large teams, and optimized business operations to support rapid growth. Prior to joining Smart City, Nathan was a VP and General Manager over the

Texas and Mountain West territories for WeWork where he grew the region from two to more than 50 locations. Before this, he served as a senior leader in the Texas Army National Guard and also launched a property management company that he later sold in 2017.

Nathan holds a Bachelor’s in Facility & Property Management from Brigham Young University, and an MBA from The University of Texas at Austin.

Outside of Smart City, Nathan stays connected to his roots in the military as a Veteran Mentor for Veterati and Advisory Board Member for Skills After Service. He enjoys spending time with his family and recently launched a business with his kids called Duty Not Reward.


In This Conversation We Discuss:

  • Nathan’s experience with the military, his MBA and WeWork and how they layer in his current role as COO 
  • How Smart City Locating adapted during the 2020 pandemic 
  • How the current team reacted to Nathan when he joined an already established team 
  • How Nathan makes a personal connection with his team 
  • Nathan meeting the CEO the first time after being hired



Connect with Nathan Lenahan: LinkedIn 

Smart City Locating – https://smartcitylocating.com

The Misunderstood Roles of the COO – Click Here


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Our guest is the COO of Smart City Locating, Nathan Lenahan. Nathan joined Smart City in January 2020. In his role as COO, Nathan drives vision and strategy at Smart City’s cross-functionality, leading departments such as sales, marketing, and strategic partnerships for the company. Nathan garnered success in previous roles where he managed revenue portfolios of more than $200 million, built large teams, and optimized business operations to support rapid growth.

Prior to joining Smart City, Nathan was a VP and General Manager over at Texas and Mountain West territories for WeWork, where he grew the region from 2 to more than 50 locations. Before this, he served as a senior leader in the Texas Army National Guard and also launched a property management company that he later sold in 2017.

Nathan holds a Bachelor’s in Facility and Property Management from Brigham Young University and an MBA from the University of Texas at Austin. Outside of Smart City, Nathan stays connected to his roots in the military as a Veteran mentor for the Veterati and advisory board member for Skills After Service. He enjoys spending time with his family and launched a business with his kids called Duty Not Reward. Nathan, welcome to the show.

Thanks for having me. It feels embarrassing hearing your bio.

This is cool. I grabbed a couple of things off of there that I didn’t even read on the first pass-through that grabbed my attention. You are a bit of a hybrid between entrepreneur and COO.

I have been all over the place. I love the passion, startups, and growth. I’m trying to see if you have the medal for making it work yourself or easily shift and helping someone else bring their vision alive.

I’ve always had a passion for kids and entrepreneurship. I did a talk that’s on the main TED website about raising kids as entrepreneurs. Tell me about this business that you’ve started with your kids. What is it?

I’ve got four kiddos, 2 boys and 2 girls. We were in the middle of Christmas break. I was itching to do something different. I wanted to have some fun with them and try something. Somehow, I convinced all four of them to want to start a little company with me. We all came up with the roles of what we wanted to do. They needed a little bit of a nudge on the idea and somewhere to start. I was that glue that brought them together.

Duty Not Reward is the motto of the battalion I served with in the Army and deployed to Iraq for a few years. I love that sentiment. You are doing the things that you have to with no thought of what you get in return. We built a little online clothing store and did custom T-shirts. We had some old logos from companies we had done before that were in the same name. The whole thing was mostly a test because they wanted a timeline on this of, “How long do we have to do this with you, dad?” The goal was, “Could we build a business and make it profitable in 30 days or less.”

Duty, not reward. Just do the things that you have to with no thought of what you get in return.

We did $2,500 or so in revenue the first month. They all got a few hundred dollars out of that each and moved on. After a few months, this wasn’t what they were super interested in. We sunsetted that endeavor but it was one of the coolest things I’ve ever done as a father. My daughter, Kylie, was in charge of a lot of the social media. She was writing LinkedIn posts and sharing them with people. One of her posts got 20,000 views.

People were excited about that. I loved it. My oldest daughter ended up starting her own business. She started her own tutoring and babysitting business. She made a few thousand dollars doing that. Her brother made flyers for her and delivered all the flyers to mailboxes in the neighborhood. He gets a cut of every job that she gets. It’s great ripples from a great time together. There were some interesting learnings.

The most grief I got about anything wasn’t any of the hard work or anything like that but I made them write copy down, and then I tried to have them read it aloud to get critiqued in front of the rest of us for marketing and stuff. They would not do it. They are like, “No way. ” It’s too vulnerable. Writing comes from the heart. It’s super interesting. That was my biggest takeaway. They were deathly afraid of sharing their own writing.

It’s cool that you got them to do the experience. One big lesson that a lot of parents need to hear on this stuff when they are doing things with their kids is that businesses don’t have to be a ten-year business that turns into Facebook, for God’s sake. A 30-day business is perfect because they get a lot of lessons, learnings, and experiences that they will carry with them forever. That’s amazing.

I love the fact that you had a defined goal that was attached to it as well, the 30 days and profitability too. The skill of presenting to a group and peers is one that they are going to have to get good at with school, college, and work. It’s great that you are even getting them thinking about it and trying it now. Don’t give up on that one. That’s a good one to keep pushing. Tell us about Smart City. What’s Smart City? What’s the basis of it? I want to go into your timeline and your career with them because I’ve got a couple of interesting questions to start with.

Smart City is one of those things I didn’t know existed until I started getting recruited. If you think of any great real estate residential brokerage out there, Compass probably would be my favorite. It’s a tech-enabled brokerage and a newer model. They are out there to help you find a home. They are licensed real estate agents and experts in their neighborhoods and cities.

We do the exact same thing. We have licensed real estate agents that help people find apartments. You could think about how valuable that is, especially if you are a professional moving to Dallas. It’s 1 of our 20 markets, and you don’t know anything about it. You don’t know if that $1,500 one-bedroom apartment is a good deal, part of town or is it walkable. You can get as detailed as you want.

If you want a one-bedroom exposed brick, gas range, and on the ground floor so you can have your Goldendoodle or dog, we can find that too or tell you, “It doesn’t exist but here are the best other three options. We’ve got about 423 agents on our team across 10 different markets. We are growing about 100% year-over-year.

What was your reason for joining them? Were you still at WeWork when they were recruiting you?

You are going to see a trend here. I like goals and milestones in my career. I had specific thoughts about what I wanted to do after WeWork. I went into WeWork with very specific goals as well. I significantly exceeded those. WeWork is based out in New York, and I wanted to do something local. It was like, “How do I help someone in Texas grow or scale and use my experience of launching new markets and helping them where they might need it?”

Ideally, I wanted to do something in real estate. My sweet spot is the intersection of real estate, people, and technology. If it could be in that, that would be amazing. Lastly, being part of the bigger seat at the table of guiding the company towards growth. WeWork was unbelievable. I had a smaller region, and there were a lot of people there that you had to influence. Those are my criteria.

The pitch I got from the CEO when she came through. I was talking to other companies, and she said, “I have this cool company. It’s growing fast. There are all kinds of crap wrong with it. I need someone to help me make it better.” Imagine the humility of someone having significant success and coming with that lack of ego.

I love this Harvard Business Review article. It’s like the seven types of COO. I’m sure you’ve read it before. In this case, I got a chance to help bring a little more experience and consistency to this CEO, who has grown it from nothing. She’s obsessed with the customer experience and has seen a lot of things but she’s also made a lot of mistakes along the way that could have been prevented probably with a little more experience on her team.

Did you come in as The Change Agent, as they talked about in that article?

It ended up being more of one than I expected. I had some thoughts about where we were going. I thought I would continue to build on the culture. Ultimately that is what we did but there were some operational things that we got wrong as a company, both before I joined and when I got here as well. Some of that was changing compensation in a way that didn’t make sense. If you want to piss people off, just mess with their money. It’s a great way to get everyone mad.

That first 6 to 8 months were about listening, assessing, and getting small wins. We ended up having to change comp back to something more reasonable. People are excited about that. I’m The Change Agent and a little bit of that mentor for the CEO, helping create more consistency and guiding her. We then ended up with a CFO a couple of months after I joined. That is the perfect complement to the CEO and me. It’s a wonderful team. We’ve made lots of changes.

How many employees were at Smart City when you joined them?

I got to make distinctions here. Our agents are 1099 contractors, and then for employees, we had about 60 when I joined. We are at 103 or 104 now. We had 60 agents as well. Now, we have 423 agents. There’s significant growth in headcount overall.

From about 120 total to about 520 total. That’s pretty solid growth in several months. When did you join WeWork, and how many years were you there?

I was at WeWork for three years.

You were pretty early at WeWork as well.

Yes. Based on the region I was in too, I was early. There are few locations. I ultimately got to hire everybody in my region. It felt like a startup within a startup at WeWork multiple times for me. Every nine months, it felt like I was starting up a new business at WeWork with a new region.

A former client that I used to coach, Marcelo Claure, when he was the CEO of Sprint, and then also I coached his second in command, Jaime Jones, for several months. Marcelo came into WeWork at a pretty strange time. Did you have any insights into some of the changes he was making or trying to make? Were you exiting at that point?

I left shortly after the fail to attempt IPO, which is exactly when he came. The path forward was very evident. It’s not like this is rocket science in so many ways. It’s very simple but that doesn’t mean it’s easy. From my perspective, they did a lot of great things of being super transparent and understanding like, “We have to make cuts. We have to be incredibly efficient in different places. This will impact things that are negotiable versus things that aren’t. How do we preserve the client experience and the incredible feeling of community at WeWork? Also, your ratio of people to the building is now half of what it used to be.” That is meaningful.

They weren’t shy about saying, “We are a real estate company. We are not a tech company.” There are lots of opportunities to get better there, and they went after them versus some of us who had been there longer and felt like it was much more difficult to make that change locally and initiate change in a way that was needed.

When you were at WeWork, it was pretty hard to go through that growth. They were in a pretty exponential growth curve for a long time. You went from 2 locations to 50 locations that you were overseeing. What did you learn from that yourself? What kind of lessons did you pull that you still carry with you?

I learned a lot. I thought the biggest challenges of growth would be a little bit different than they were but if I were to take one statement that I learned about around is that there’s no greater risk to the business than outgrowing your culture. You can think about getting things wrong on timelines and opening dates and everything else but there’s no way for me as the leader of that region to be everywhere that I needed to be. Who’s the steward of the culture, then? Who is creating that? That’s created by every single person and everything that they do and the actions we take every day.

There’s no greater risk to the business than outgrowing your culture.

I got to see that through multiple markets wherever I went. There are always small tweaks in the culture and small differences but at the end of the day, people cared about each other. They believed in the mission of helping people make a life, not just living. We got to do so many things that we were passionate about. For instance, I’m a veteran, so I got to be part of an initiative with Veterans in Residence and Bunker Labs. We made a huge, very proud statement of, “We are going to hire 1,000 veterans in the next two years. We are going to help people start their own businesses who are veterans or military spouses.”

I got to go launch that from the first location in Denver to the second location in Austin. We put it in 25 different cities. I got to see veteran businesses all over the country and help push that and create one of the biggest alliances and accelerators in the country for veterans, which is amazing. That’s hard. The other piece is that it happens fast. Helping people understand what their world and its impact on it is.

You read books that say, “Worry about what we can control.” That’s somewhat helpful. What does that mean? There are different levels of control. I expanded on that. We used to do this exercise called you, me, we. It’s between you and your teammate or you and a cross-functional leader from a different department like, “What do you do, what do I do, and what do we have to do together.”

An example of that with my boss was like from manager, and below, I could hire no question as fast as I wanted to. Director, we had to talk about and work together. VP is up to him but if he wanted to call me in and ask for advice or thoughts, then he could bring me in. I love that construct but the other piece of the construct was, “What can I control in this role? What can I influence in this role? What should I just be informed in this role?”

People wanted to own everything. We hired employees, so it’s like, “It’s my building, my sale, and everything.” That’s not the case. We should be informed on sales and who’s going to occupy your building and should be influencing where we can on that because customer experience matters. The things you can control are who’s here, what their attitude looks like, how we empower them, and how we educate and inform. I like the idea of doing those exercises with your team of knowing, “What’s my role, your role, and our role.” Also, “What do I control in this situation? What do I influence, and what do I stand informed on?”

People want to own everything.

Do you think your experience with the military, your MBA, and WeWork layer onto each other or was one more valuable than the other?

They certainly layer like the nuances that you add. I feel like I got such a crash course in leadership with the military quickly. It makes so many things easy these days. What I mean by that is I don’t think people realize the level of leadership required in the military sometimes. When you lead a person, you are responsible for everything. The number of times I was up at 3:00 AM picking someone up from jail because they hit their spouse or dog and got arrested, that’s my fault.

I’m the one having to hold them accountable, pick them up from jail, and make sure that they get to be a hopefully better human being after that. I’m getting chewed out by some general, colonel or whoever because me and my team failed. If you go off to training for two weeks and they didn’t leave a debit card for their wife for food and groceries, that’s absolutely my fault. You come into the civilian world, and they are like, “You don’t have to worry about any of that stuff that’s not part of the job.” It gives you a lot of perspective on how easy it can be.

That’s a huge lesson. I’ve never even heard that before. I’ve talked to a lot of people with a military background. That’s an important lesson that you take huge ownership of your entire team and that everything that goes wrong is your responsibility. There’s a lot of humility that comes with that as well.

You want to go ahead and get some humble pie. That’s a great way to pull yourself out of bed at 3:00 AM for someone else, essentially, you feel like you failed.

Do you bring that culture into your role now as a COO? Do you try to carry that over as maybe a core value of the organization or is that the way that Nathan operates? Do people see that in you, and do they live up to that for you as well?

I take a lot of pride in one of my personal values, and it is to operate without ego. I take that everywhere I go because, at the end of the day, all I care about is getting better tomorrow. I don’t care where it comes from or how we do it as long as we do it ethically. That’s absolutely a piece. We did this great event. We did a GORUCK event for the twentieth anniversary of 9/11.

SIC 187 | Smart City

Smart City: At the end of the day,, all I care about is getting better tomorrow. I don’t care where it comes from or how we do it, as long as we do it ethically.


One of the other leaders in the company suggested it. I agreed without knowing what it was. I sent something out to the company saying, “We are going to do this event. We would love it if you would like to join us. If you can’t afford it, other people will sponsor. They’ve already volunteered.” It ended up with eleven people out there.

We are thinking we are going to do this twelve-hour rock march. Rock march is bringing a backpack heavily laden, at least 30 pounds because I’m a bigger guy, plus the gear you are supposed to have like, “Twelve hours, okay. Rocking is not a big deal. With 30 pounds, I will be fine.” The other piece of it is that you are supposed to have as a team an American flag and then a 25-pound weight. That’s a team weight that you pass around whenever. That’s what I’m thinking it is.

What it actually is, is much more than that. What they did is they smoked us with our 50-pound packs on for the first three hours, which means constant sit-ups, pushups, squats, bear crawls up upstairs, and crab walks down the stairs. I don’t know if I have been that miserable in a long time. Everyone is looking at me like, “What the hell did you sign us up for here?” I’m like, “I probably should have done a little more research on this. ”

Once we started walking and going through this, what an unbelievable experience to bring people together. There’s nothing that brings people together better than doing hard things together. Every one of our 11 people made it all 12 hours. I talked about that 25-pound team weight. We ended up with 50 of those freaking weights. They started off at about 30 pounds and went up to 120 pounds. Going in thinking I’m going to carry 50 pounds all night, I end up carrying, on average, between 100 and 110 because I have a 60-pound sandbag on my shoulders all night too.

I’ve never had so many muscles cramp at the same time in my life. We are evenly split. There are 6 guys and 5 gals, and everyone is finished. I couldn’t tell you if I have been more proud since I have been at this company. Sometimes I do worry about like, “I don’t want to be too domineering with culture and the things I want to bring to the company. I want to be an example so others can shine as bright regardless of your title.” I feel like I’m sensitive. I don’t care about titles and the impact on culture that way. That’s not how it works for me. I’m a little more reserved than I should be on bringing some of those values, especially in the military and that ego stuff but I try and show it every day.

SIC 187 | Smart City

Smart City: Shine just as bright regardless of your title.


You live them may be more than require others to live up to them, which is still pretty cool. How about from the MBA that you did? You did your MBA at the University of Texas. What did you pull from that into your role now as a COO?

When I did it, my employer was willing to pay for it. I was like, “It’s a safety net. I’m going to get an awesome network. Let me get to the best school I possibly could.” I got into UT. UT probably shouldn’t have admitted me. I did not have the scores to get in but thank you. I love learning and enjoyed it. I walked away thinking maybe I didn’t learn as much as I did.

When I got to WeWork, though, I walked into meetings and challenges feeling so informed in a way that I was surprised by being completely honest. I would absolutely attribute that to the MBA. Working through hard case studies, challenges with my peers, and our groups, and absorbing way more than I thought, I found it to be incredibly valuable, especially for WeWork.

During my first week at WeWork, I was Head of Operations. I was the number two person for the region. This is a COO-type role. They are like, “We gave a 30-day notice to all our cleaners saying we are firing them, and we are 21 days into that notice. We need you to have that across five different cities. We need you to negotiate a new contract and have it ready and in place in nine days.”

I’m like, “Do you know how much it costs now?” I asked simple questions and started to work through it, and nobody had any idea. I end up building the whole foundation of like, “Here’s the financial model of what we need to be at. Here’s where we are at. Here’s what it looks like. This is the ratio of cleaners per square foot. This is how many per hour,” all this stuff. We ended up using it as a model across many cities. There’s no way I could have done that without the MBA.

You brought in some real solid skill into that. Joining Smart City in January 2020, and then you are in your second month, and COVID hits. What’s going through your mind? Were you location-based? Were you guys all in the same office at that point?

We were across multiple cities still at that point.

Were you all going into an office?

Correct. We are going to an office every day. It’s funny because, in my first 30 days, I did 99 one-on-ones. I had 27 pages of notes from all the one-on-ones, listening and trying to figure out, “What are the pain points?” I’m going to the root of everything and trying to figure out small wins. One of those ones is, “We want more flexibility, transparency, communication, and benefits.” Those were like the heavy hitters.

We were excited about some of the plans we were putting together. One of those was work-from-home Fridays and a little more flexibility during the week with Flex PTO. We announced that work from home Friday the week before the pandemic hit. I was like, “Big win.” It then totally fell flat in our faces because we were home the next year. That one cracks me up. The little irony there.

The best part of it was watching our team adapt to a remote lifestyle was pretty cool because our agents tour most of their clients. They try and tour the apartments as much as possible. It’s much harder to close or help people find apartments when they don’t see it. You might as well go online and look all by yourself, and that’s pretty overwhelming too. The adjustments that they made like video tours or FaceTime tours there are very specific appointment slots.

I feel like we reacted faster to anybody. We had a couple of weeks where we struggled. We were worried. We went into a war room. As a leadership team, going in there, thinking, “We are probably going to have to make layoffs. This is not going to be good for us.” It was a pivotal time for me. Coming in, I hadn’t learned enough to be leading in the way I would like to or help with big decisions.

We are going in with a mentality, “We probably have to cut people or lay off. We got to make hard decisions fast.” I remember our CEO jumping up on the table, and she’s like, “I have a crazy idea.” It’s funny because I’m trying to come in prepared and got the agenda. “This is the stuff we are going to work through.”

A couple of minutes in, she’s blowing the whole thing up and says, “Instead of laying anyone off, we write our own story and expand to 3 new cities in the next 90 days. Basically, we are expanding our derisking and revenue sources and growing during a pandemic. Do we think we could do it? In this way, we don’t have to lay anybody off. We are investing in the future.” You would probably believe we all rallied around that. We made it happen. We launched San Antonio, Denver, and Fort Worth as our markets and then identified Nashville, Atlanta, and Orlando soon after to go. We ended up launching those not too far after that.

That was a pretty huge strategic move to choose to grow during a pandemic versus cutting back.

It was scary as hell but that’s the vibe of our company and who our CEO is. She’s not going down without a fight. When she’s down, you got to fight her some more because she’s still not done.

When you were starting and growing your first 90 days as the COO coming into the organization, what was it that got you to sit down and say, “I’m going to do 99 one-on-one meetings with people on the team? That’s highly unusual and awesome at the same time.

For me, I don’t want to ever come in and assume I know what’s going on. “How am I going to learn better than the people that have been doing it? What other impact am I going to make in the first 60 days or 30 days that is so monumental than building trust?” At the end of the day, that’s the best thing I could be doing. One of the best places to start building trust is listening. Shut up, listen, and ask good questions. Be authentic in that pursuit and then do something about it.

SIC 187 | Smart City

Smart City: One of the best places to start building trust is just listening. Shut up and listen. Ask good questions.


I have been to many places where they do employee surveys or come and listen, and then they don’t do crap after. Power is in the follow-through, and that’s where you earn trust. I was hell-bent on listening first, building the plan, and then giving good wins or small wins, at least to show, “Not only did I listen, but we are doing something about this.”

Was there any distrust of you coming in or any pushback from the current team? Were people like “Who’s this new guy coming in on top of us?”

First and foremost, I mentioned there was a compensation change before I joined. If you were to paint a picture of that, the way they put it to me was it felt like our CEO reached into their pockets to pay some big wig to come in and tell us to do our job, even though we already know how to do it. That’s the sentiment I joined with. That was a little surprising to me. I did know about the compensation change, and there were opportunities to do that better but there were opportunities to not do that in the first place. That was probably the biggest lesson. Cassie, our CEO, she’s like, “If I was the board, I would’ve fired me after that.” I agree with her. I would’ve fired her too.

How do we avoid mistakes like that in the future? Even with our senior ops person, it took a little bit of time for him to realize that, “I want the best for you. How do I help you get to whatever you want, whether it’s here or somewhere else?” That takes time. It took a lot of tough conversations with that person to figure out, “You are not in the right spot now. How do we find what you are good at?” The person is amazing when it comes to operations or starting things up. He’s a startup guy. If I will say, “Go do this. Here’s the idea,” I will give him enough resources to run with and that guy will run. He was doing everything.

He was the glue that kept finance, people team, HR, sales, customer experience, and everything. He was doing everything. It’s wonderful to see him blossom even further and make the impact that he wanted to along the way and for us to build that relationship because he’s like, “Go, go, go.” That’s one of my favorite things. I was trying to ask him how life was one time and he was like, “I don’t want to talk about that. I want to talk about work.” I’m like, “This is how it’s going to go. I get all of you and not just the work version.”

My favorite story of him was, we are talking through. I’m like, “Anywhere I go, I figure out what the norm is. If the norm is working 40 hours, 50 hours or whatever, my goal is always to make a bigger impact in that time or less time than anybody else.” Before I even finish that, he cut me off and he’s like, “No, I will work more hours.” I’m like, “That’s not what I’m looking for. I’m looking to make it more efficient and being impactful.”

Few people get that. It’s not about working harder. It’s not like the fly is going to keep banging its head on the window until it ends up dead on the window. It is about being more efficient. I love the, “I get all of you,” component to it as well. How do you make sure that you build that connection with your team on the personal side? What things do you do?

There are things I could do way better on this. There’s a study from Harvard or something reputable. It said something like, “The more inside jokes a team has, the higher level of trust there is.” I love that. That means that you are sharing more of yourself. It’s simple things. I’m always quick to crack a joke. Every all company meeting or major meeting, they make me kick it off with a dad joke. It’s something as simple as that.

In the military, especially, you learn to laugh even in the hardest of times. That’s the mechanism. I always start our one-on-ones off on personal notes like, “How’s it going?” One person has been training for a marathon. There are multiple new parents in our organization. It’s just sharing, genuinely curious, remembering spouses’ or kids’ names, and asking about those things. It’s all simple things.

The key is that you care. I remember I had a boss that I reported to back in the early ’90s. I went into our one-on-one session one day and he is like, “How’s your weekend?” I’m like, “You actually don’t care. Why don’t we jump to the numbers? Every time I start talking about what’s going on, your eyes glaze over waiting to talk about the metrics. Let’s talk about the metrics because you don’t really care.” He was like, “You are right.” That’s probably the key that you bring into the role. How did you get to know the CEO? You didn’t know her prior to joining the company, did you?

I didn’t know her. She had a headhunter or recruiter out searching for people. From her story, she talked to a whole lot of people. The story is a little funny. This is what she shared with me. I don’t know if it’s totally accurate or not. My head of operations when I was at WeWork came over and interviewed here for the same role. We are pretty open. I truly believe in building trust. I always want to be the first person to know like, “If it’s an opportunity for you to grow somewhere else, then let me help you. If I can keep you, then that’s great too.”

I had taken him out to breakfast and we were talking. I had shared, “I’m potentially looking as well,” after he had shared that he was. He talked about this company. I’m like, “That company sounds similar to a company that had reached out to me.” According to the story he interviewed, it went well, and he shared some stories about me. In turn, they reached out to me after he shared that. I ended up getting the role. Cassie still loves him. He’s an amazing leader, in general. He’s a great human. It shows. We were out to breakfast and had that personal connection, enough so that he was sharing opportunities that he was working through at the time.

How did you get to build the trust and the relationship with Cassie then? What did you think you two did in your first 90 days to get that into gear?

Cassie needs someone that’s a little bit of a firm hand. She’s your classic startup Founder or CEO. She wants to move fast. She goes off gut reaction. She wanted to try things yesterday. Everything is too slow. I love moving fast too. I love trying things and breaking stuff but I’ve also learned to be the chameleon. Regardless of what my natural voice is and a lot of these things, I easily fall into what’s needed versus who I need to be.

I was like, “Cassie, that’s a dumb idea. We should not do that. Here are the five reasons why.” You can’t beat around the bush with her. She’s like, “You are right. How else do we do it?” I’m like, “I sparked a great idea over here that we could talk to,” and then she will tell me that’s dumb and then we will move on. At the end of the day, we both took the time to know who we were as people first and built trust off of that. She had had her first kid when I joined and I have four kids. We bonded over that. I don’t know if we would’ve done so well a few years ago before she had kids. We would’ve clashed there because I’m big on work-life rhythm.

The biggest thing we negotiated was not compensation, vacation or anything. It’s like, “Cassie, I’m going to be clear with you. If you have something that is needed or urgent, you should never question whether I’m going to do that for you and when you can call me, I will take care of it. If it’s something you want or something that’s nice to have, I’m going to see you on Monday. I’m not doing it on the weekend. I’m setting the example not only for myself and my family but for every other employee that’s at this company. How do we get them all excited to do more in 40 hours, 45 hours or whatever the number is than anywhere else because we respect the time for them to recharge and go off and have lives outside of here?”

I told her that and that stuck with her. A few months after, I’d worked through the weekend and working through all kinds of tough stuff and she had no idea. She found out later and was like,” It’s great knowing that I don’t have to worry about that. It’s one thing to say but it’s so gratifying to see to reinforce that idea.” Those things and then having a small win. Winning that ops leader that wasn’t a big fan of me and building trust and seeing that person come around are things that mattered a lot to her because that’s her team. That team took her so far and built everything from scratch. It’s amazing what they did. Coming in doesn’t mean you are worth any less. We are just growing as a company.

You are right about the fact that when she had her first child, it all of a sudden gave her a glimpse into the window you already had. I remember when we were building 1-800-GOT-JUNK, I was the first executive to have a child on the leadership team. Over the next few years, all six members ended up having kids and it changed everything when they realized, “We can’t do 7:00 AM breakfast three days a week. We can’t go for beers three nights a week. We can’t go away on weekends and brainstorm together.”

It made us a stronger team as well because that work-like rhythm as you called it became real. That’s almost where our culture emerged. You also bring something special to the table where you have that entrepreneurial side to you which, at least lets you understand the entrepreneur because you partially are one wrapped in a COO body.

I enjoy it. She’s unpredictable, fun, and a pleasure to work with. She’s always willing to have her mind changed. That shows a lot about her character as a human.

When you are telling her, “No, that’s a stupid idea. Here are five reasons why,” will you ever do that in front of the rest of the leadership team or do you do that privately with her? Is it a bit of both depending on the situation?

It is a bit of both. Those were conversations that were happening between them and her before I was even here. It’s not like it would have been new. I’m probably a little more seasoned. She will take a little bit more of my comments at face value. The same thing with our CFO, whereas if our head of sales, head of people team, marketing or whatever, they might have a little more of a battle working through her, trying to say no and justifying why. She wants to be listened to.

The other thing is that I don’t know where this comes from but I know what to filter out. As far as our CFO, I’m like, “You said something extreme there. I’m going ahead and throwing that in the trash and ignoring it because I’m not doing anything with that.” You got to say it five times before I know you are serious about something that drastic and I might be like, “We are not going to do this bonus,” or something like that. “We are not going to do that anymore. This population isn’t going to get that.”

People internalize that very quickly. I will go back and coach her, and we will have conversations together on that. “Here’s why you don’t do that.” One of the big ones was that she used to say I in my way too much like, “My company or my money.” She’s the sole owner of this company, which is a wonderful story but people saw her as the company too. I was like, “We have to talk. This is our company. We are all contributing to this.”

People are paying everything on her versus like, “This is the challenge of being a business owner and a business leader,” and all those things. It has been wonderful seeing how willing she is to take feedback and open up. She’s willing to admit she’s wrong in front of anybody but if she’s right she going to tell you too.

I want to go back to Nathan Lenahan who’s graduating from BYU and getting ready to start off his career. What advice would you give yourself back then that you know to be true now, but you wish you’d known at a younger age?

I have a quick story that I feel like I learned right then and you can’t let life happen to you. You have to take control of it. I remember I got out of the Army and the way college career worked is 9/11 hit and that was my first semester of college. I took off for the Army and came back a couple of years later and I’m trying to finish. I’m like the gritty older little weird veteran in class.

I freaking hate life. I’m struggling to transition. The best job I could get is $11 an hour. I have a family of 5 at this time and I am having the biggest Nathan pity party you can have. I’m struggling with having no purpose, community or anything. I have no friends. I remember walking across campus and hating life. I was like, “Nobody cares about your freaking little pity here, except for you. You are the only one that can fix it. How do you fix it?” I’m like, “I’m going to go fix this.” I’m pretty sure I skipped class and I don’t recommend that necessarily.

I decided the way I was going to fix that was going to go walk onto BYU’s top 25 ranked football team and find a place to have friends and have a community, despite the fact that I’ve never played football anywhere besides flag football. I get over and talked my way in. I managed to get into Coach Ted Wells’ office, he was a recruiting coordinator at the time. He’s an incredible human being. We realized it was a running clock and I have no eligibility. That’s the real reason I couldn’t play Division 1 football. It had nothing to do with my lack of talent or anything like that.

All I remember is that it wasn’t the question. It was the follow-up questions that mattered. I was like, “I want to be part of something. I need this and I’m struggling. It feels like part of a team. I will volunteer and give my time. Let me be part of this.” He said, “I can’t do anything on the team but there are student manager jobs with the equipment team that you could do. They run the sidelines for games. They travel with the team. They set up the locker rooms and run all the practices.” I’m like, “Sign me up. Let’s go with that.”

He literally takes me down there and I interview on the spot with the director of equipment. His son happens to be in Afghanistan as a US Marine, and we hit it off. His only hesitation is that I’m a military guy and that I’m going to talk back to the coaches, players or anything like that. I’m like, “They are pretty rough on you in the military. I’m pretty sure I can hold my lips,” but I got the job. It was the best turning point of my life to take deliberate action and get results.

I got the job and friends that you always hear about from college. It turns out it was a full scholarship. I got a full ride to school with stipends. I still got swag in my closet from there. My buddy is the director of football operations up there now. When I was in Utah, I got to go see a practice. It was amazing. One decision of taking control instead of letting life happen to you. That transformed me. I have been trying to live ever since.

I love the story that backs up the thought behind it as well. Nathan Lenahan, the COO for Smart City, thank you so much for sharing with us on The Second in Command show.

It’s my pleasure.

I really appreciate the time.


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About Nathan Lenahan

SIC 187 | Smart CityI’ve journaled more than I ever have this year especially as we build our company homework to be the world’s most loved home service experience on earth. I think a lot about the kind of people we want to attract and how to create a feeling of belonging in our company. Here’s an entry from February: Let’s start with being proud of who we are and who we help.

I’m proud to be a veteran. A father. A husband. Someone that cares about others. Someone that loves this country despite its imperfection.


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