Moneyball and the Art of Team Building

In this episode, host Chris Collins dives into the art of team building with Dennis Siggins, founder of Cape Cod Gutter Monkeys. Discover how Dennis applies a Moneyball-style approach to hiring, training, and empowering employees to transform a small business into a multi-million-dollar powerhouse. Whether you’re a business owner, entrepreneur, or just love a good success story, this episode is packed with insights on finding hidden talent, building strong teams, and shaking up traditional industries. Tune in for inspiration and practical advice!

Chapters

• 0:00 Introduction to Team Building and Moneyball
• 5:36 The Moneyball Strategy in Business
• 10:27 Hiring for Personality Over Skill
• 15:59 Training and Developing Employees
• 22:07 Incentivizing and Retaining Talent
• 30:17 The Art of Delegation
• 37:31 Surrounding Yourself with Talent
• 43:18 Putting it all together - Story of Innovation

Transcript

Episode #1 Transcript

RUSTY DRIPEDGE
 Hello everyone and welcome to episode one, Moneyball and the Art of Team Building. Hello Dennis, how are you doing? 

BOBBY DOWNSPOUT

Doing good Chris. How are you doing? 

RUSTY DRIPEDGE

Good. It's been a while. We've been talking about building this set, doing a podcast, probably a couple of months now. Feels good to finally be here.

BOBBY DOWNSPOUT

 Yeah. Chris, behind every successful business owner is his team, vendors, customers, investors, whatever. But the most important team every new business owner will ever build is the team of people he works with every day, the employees. I've been self-employed more than 40 years and I've launched successful startups in several different industries and I've developed kind of a different strategic process of hiring. But before we dive into team building process, let's go back and take a little side trip down and visit Moneyball.

RUSTY DRIPEDGE

Interesting on how much importance you put on team building. Our very first podcast is about team building, 

BOBBY DOWNSPOUT

It is because that's what your company is built out of, the people who work together every day. And if you don't have a good team, you don't have a good company.

If you don't build a proper foundation, you don't have a good house. 

RUSTY DRIPEDGE

Yeah. I'm excited to talk about this because Moneyball is one of my favorite books. 

Great book, great movie. 

RUSTY DRIPEDGE

Great movie. Yeah, it's about baseball, which I love. Absolutely my favorite thing. And there's a Red Sox tie in, of course. 

BOBBY DOWNSPOUT

based on the story of the 2002 Oakland A's season, Moneyball focuses on team building with a lower overall payroll. Basically, Moneyball begins

In Oakland at the beginning of the 2002 season, when Oakland once again was just gutted, end of the season came the previous season, they lost Jason Giambi, they lost Johnny Damon, their two biggest stars to New York and Boston. And once again, the small market Oakland A's just did not have enough money to pay the salaries total of 21 million.

that Johnny Damon and Jason Giambi were getting at New York and Boston. And what Billy Bean and his team of statisticians were doing was developing a strategy to find undervalued players with undervalued talents.

They, before pitch count and OBP on base percentage were really considered part of the game. We all knew what they were, but they weren't heavily weighted when looking for star players. Billy Bean theorized that he could replace Johnny Damon and Jason Giambi with players who had similar on base percentages. He brought in

Scott Hattaberg, who was considered, 

RUSTY DRIPEDGE

yeah, he was a catcher for the Sox, 

BOBBY DOWNSPOUT

but his elbow was shot. He couldn't really throw the ball back to the pitcher, let alone gun guys out at second base, but he walked more than anybody in the league except Barry Bonds. And they also brought in Jason Giambi's little brother, Jeremy Giambi, who they picked up for the league minimum, $237,000.

and Davey Justice, who was an aging center fielder from the New York Yankees, and they replaced Johnny Damon with Davey Justice. And the combination of players that they brought in replaced the on-base percentage of Johnny Damon and Jason Giambi. And the story is they won more games than any other team except the Yankees.

They each tied with 103 wins. They lost to the Yankees in the ALDS, but the fact of the matter is they did it with about a quarter of the payroll. New York Yankees had a payroll somewhere up in the $130 million range.

Oakland had a payroll of about $38 million that year. The experiment worked. You see it all across the leagues these days. That's the name of the game. In fact, Billy Bean was offered a job at the end of that season by the Boston Red Sox. John Henry, Boston Red Sox owner, really wanted to bring in Billy Bean.

recommended his good friend and another believer in the Bill James statistician theory. they, the Red Sox basically took the baton. They brought in Theo Epstein, who was a great friend and coworker of Billy Bean. And they would end up putting together a championship season in 2004 to break the curse. And they did it with Moneyball Theory.

RUSTY DRIPEDGE

Yeah, youngest GM in history of baseball. Unbelievable. 

BOBBY DOWNSPOUT

He took it on the chin too in the Boston press. my God, He got his ass kicked so bad. 

RUSTY DRIPEDGE

And I was probably one of the people throwing tomatoes at the time as well probably. A little bit of that is on me I guess. 

BOBBY DOWNSPOUT

The lesson we learned from Moneyball is simple. Find the piece to the team building process, the undervalued assets that everybody else doesn't see.

Fortunately for me in my business and most of us in business, our competitors are not as astute as major league baseball teams. So when we in business develop a creative way of team building, we can keep it in our back pockets because nobody else sees it and we can use it over and over and over again and I can tell you, it works. It works.

Chris mentioned earlier, in the intro, one of my lifelong friends, Andy Brennan, he and I, we married our wives back in 1983. And 30 years later in 2013, we all vacationed together in Hawaii. And that's where my friend Andy and I started talking about starting a business together. I kind of threw the idea out that

that gutter cleaning on Cape Cod was an incredibly underserved market and somebody needed to fill that void and we did. 

RUSTY DRIPEDGE

Let me ask you a question. How did you identify gutters? There's so many things on Cape Cod. It's a service industry down here. How did you notice that it was gutters that was really the underserved thing that you wanted to attack?

BOBBY DOWNSPOUT

 I'm a lifelong builder, roofer, tradesman. I've also been self-employed either full-time or mostly full-time since I was 10. So I've always been cutting lawns, painting houses, roofing houses, eventually building houses. And when my wife and I sold our company back in 2010 and we moved to Cape Cod, I was too young to retire. So I just, I would do...odd jobs on the weekends. took Monday to Friday off and I worked Saturdays and Sundays and no one cleaned gutters. I started cleaning gutters and doing odd jobs for family, friends and neighbors just for fun money. was way too young to retire and that's what I was doing and it became very evident that gutter cleaning is not being served on Cape Cod at all. It was easy. It was easy.

And that's what Andy and I decided to, we chose to launch our company as the Cape Cod gutter monkeys. It's been very successful. I think we have five or six and we're about to open our seventh office. We recently began franchising and it's going well. But ultimately,

If you're to build a company, you've got to build a team of coworkers. that's where... 

RUSTY DRIPEDGE

Yeah, and I have to say firsthand, being here for the last year and a half, it's amazing group of people that you have here. Everybody here is just really, really interesting to work with. I'll give you one example yesterday. I don't know if you're aware of this. We were setting up the podcast booth here, and I didn't ask for it. I don't think anybody told anybody, but within...

Couple of minutes of the trucks coming back in, had two guys, I three guys, I three gutter monkeys in here helping me do things. They hung the panels on the walls, they helped me hook up the equipment, move the table around, assemble the table. One of your newest guys, Marcus, right? Yeah, yeah. Marcus came in, he put together the table for me. It was really amazing, and that's the kind of thing you see here. It's an unbelievable team. They didn't need to be asked, they didn't need to be told, they saw they needed something to be done, and they did it., which was real credit to you and Andy, know, a team. 

BOBBY DOWNSPOUT

Let mention Marcus right now. This is a young kid that used to work at the hardware store. no real skills in the trade. He's just a young, young guy, 19 years old. We know his mom and dad, because we installed the gutters on their home eight, seven, eight years ago. Marcus is our perfect guy. And we're going to talk about team building in a little while, but

Marcus is that guy that he just flies below everyone's radar. He's a young kid, doesn't seem to have extraordinary skills in the trades, and he's been wonderful. He's been with us for almost a year now, and he's just a great young guy. He shows up every day, and another year from now, he's gonna look around and realize he's got some skills.

because he just shows up every day and he works hard. 

RUSTY DRIPEDGE

Yeah, it's real testament to the way you guys bring people in here. So I guess maybe we should just dive into it then. Maybe we should dive into your approach you've got. You've got a five-step approach. start with hiring. 

BOBBY DOWNSPOUT

Well, again, looking at the moneyball approach, who do you hire? We only have so many positions in our company.

And most companies have a skill set that they're looking for. And so they search through many, many different ways from technology to advertising and traditional advertising, looking for a specific skill set. I don't do that. look, there's two things, skill set and personality.

Skill can be taught, skill can be learned, but personality can't be changed. If you're 25 years old or beyond, you have your personality. So I look more in hiring for the personality.

Our company has almost 30 people in the corporate office right now, and very, very few of us had any skills or training in the gutter industry. I think they're all upstairs right now moving equipment. Yeah, they are. think everyone's up there. The gutters are out. I'm going to tell you, chain restaurants produce good employees. If you're the manager of a Bertucci's restaurant,

And your last name isn't Bertucci. I know how you got there. You've washed dishes. You've been a line cook. You've been a crew chief. You you've been a department manager. You've been a shift supervisor. You've worked the register and dealt with a grumpy customer or two over the years. You've probably worked through a busy Christmas season at the mall. If you are the manager of a Bertucci's,

You're my kind of guy because you don't call in sick and you deal with adversity. You're dealing with customers all the time. I would say right now, at least three or four of my crew chiefs came directly from restaurants. I got one or two from Friendly's. I think we got one from IHOP, two out of Bertucci's. So yeah, mean, restaurant managers.

is a great source of coworkers. Here's something else. Restaurant managers don't get paid very well. So if I shop for my coworkers outside of my industry, I can take a guy like James or Adam, you know, they were managing restaurants, I bring them in, I can start them at the money that they were making.

which is well below what it would cost me to bring in a skilled carpenter who knows how to install gutters. So I'm bringing in a restaurant manager at his current salary, but within a month he gets his first raise. Within three months he gets his second raise. And I know he's a good coworker because he's a manager of a Friendly's or he's a manager of a Wendy's. And that's the personality I'm looking for.

I bring him in from another industry, he very quickly begins making more money than he did in the other industry, but he's still making less than what it would cost me to bring in a skilled carpenter. And I can tell you a lot of skilled carpenters come along with egos and a lot of other things that don't benefit me and they may not get along with people that well. So when I undertake the task of hiring,

I'm looking more for personality than I am skill set.

All of my coworkers, all of my employees get one sick day a month and two paid vacation weeks per year. That's part of their starting package.

I've got guys that have been with me for years that have never taken a sick day. They just bank that money. Every day, every month they get paid one day. It's either sick slash personal day. So they get that money in their paycheck. And over time they bank it. So three, four years in, I've got a coworker who hasn't had a sick day and I'm happy. And my coworker,

hasn't had a sick day and therefore he's been banking all that money, he's happy, it's a win-win. Also, process, finding these guys, it makes it kind of easier for you, a recession or during these other periods where it's tougher find people can actually add to your payroll, right? So it's easier to kind of, if you're not shopping for some particular guy, this pool of people that you have available to you is much larger.

than a skilled carpenter and trying to find a skilled carpenter in the good times. Maybe in a recession or something, it's easy to find that skilled carpenter. Definitely during the good times and it's harder to find somebody, this a lot bigger pool to sort of be fishing in. Correct. Correct. And in addition to that,

getting back to how you were bringing that up, most of my current coworkers came here because they knew someone who either worked here or knew someone who knew us. they bring in good people. Good people bring in Right. And I tell all my guys and my girls, if we're looking for somebody new, don't recommend any knuckleheads because you might end up having to work with one. Being stuck on a truck for eight hours cleaning gutters with a... Yeah.

No, so I mean, I don't think I've ever pulled in a quality coworker from Indeed or ZipRecruiter. Most of them came here because they knew somebody who worked here. Well, they knew a customer of ours or they just knew one of us. 

RUSTY DRIPEDGE

Yeah, so I'm from the high tech world, right? So I've been doing startups for the last 30 years. Each one than the other. And as you got smaller and smaller, that became such a really important part.

Almost all the people we bring into startups knew each other for exactly that reason. Because you can't take the risk on somebody that you don't know. Because in a small startup, they can blow you up very quickly. When you've got three or four guys working in that sort of environment, a bad hire can really blow you up, really hurt you. So that's the same sort of thing we used to do there. So that kind of resonates with some of my experiences that I've had in sort of the tech world.

BOBBY DOWNSPOUT

 So Chris, getting back to sort of my strategy on hiring, hire.

train, incentivize, delegate, hold accountable. So we just talked about hiring. We're going to talk about training.

Once a successful candidate is hired, and long before he becomes a coworker, he's in training. Now, if he has a high skill set,

He could be very difficult for me to train because the way we, our process is so different from everybody else. If I hire a high skillset, I got to unlearn all the stuff that he are bad habits. was talking to you about roofing earlier today, training. When I, when I was on the roof in business training skilled roofers to unlearn all the

bad process that they've learned and then retrain them is hard. It's difficult. And a high skilled guy, especially in the trades, almost always comes with some level of arrogance and a little bit of an attitude. Yeah, I think what you were saying about the way he does things is basically the way his father did it. And his father's doing it basically the way his grandfather did it and his grandfather's doing it basically the his great grandfather did it. So they all bring in that same skill forward with very little innovation, very little changes.

years ago, you know, I don't golf. I it's not in my blood. But years ago, a friend of mine, Steve, who was a local golf pro at up in Bethlehem, New Hampshire, he bought me a set of clubs. He and I flipped the house or two together. And as a thank you, he built me a custom set of clubs. I said, Steve, you don't know, don't I don't golf. He said, well, it's what I do, you know, and it's my gift to you. So over the course of a summer,

beginning probably in April, Steve and I went to the range for 45 minutes on Monday afternoons. And then on Wednesdays, we'd go play nine holes of golf.

And this went on. Now I didn't know anything about golf, so I didn't have any bad habits to break. We had a great time that whole summer. That was our MO. And one time I had a break in the action and I went out and I went out on a Friday or something and hooked up with three other local guys at the Bethlehem Country Club. And the following Monday, I said to Steve, we went out to the range for our Monday night practice session.

I said, Steve, I played golf on Friday with A, B, and C. And he said, yeah, yeah, I know those guys. I said, how do you think I did? How would I compare to them? He said, they're not even in your class. You're 15 strokes better. And I said, how did you know that? He goes, because I know those guys. They've been playing golf for 20 years. And they've been doing it wrong for 20 years. And he said,

They can't be taught. They have so many mental and emotional barriers to learning. He said, I could never teach them what I've taught you. like I was in that foursome with you. 

RUSTY DRIPEDGE

Was I in that foursome?

BOBBY DOWNSPOUT

 And I said to him, you're right. mean, we kept our own scorecards, but I said I was probably 10 to 15 strokes better. And I was shocked because they talk the talk. They know phrases and verbiage that I don't know.

They get Golf Digest in the mail, they subscribe to the golf channel and they got the shoes and the glove and I'm out there in my jeans and my t-shirt, but they weren't very good. And the lesson is these guys have poor form and bad swings.

RUSTY DRIPEDGE

Yeah, I kind of experienced that with my wife. My wife Sandy is playing. She grew up without any sort of hand-eye coordination sports, never played. Never played like a baseball, softball, anything like that. So during COVID, we started playing golf and she started going to take lessons North Conway. so first, it's Rocky taking her out and playing with her and then she's getting a little better and a little better. And all of sudden I notice.

She takes direction unbelievably well. If he tells her to do it one way, that's how she does it. Now I can't correct her because you don't want to get involved in that butt. But unbelievable. Sure enough, this year we've been playing a game against each other called bingo bangle bongo. I don't know if you ever played it. The closest, first one on the green, closest to the pin, first one in the cup. And she is kicking my butt. And it is about that. She takes direction incredibly well, but she doesn't have to unlearn the baseball swing. 

BOBBY DOWNSPOUT

There you go. The other things that I've kind of learned.

and it's very hard. It's probably too late for me to sort of, I have to kind of learn to live with those things now at this point is so ingrained. So I can kind of feel, I can kind of feel their pain actually because I'm kind of experiencing that with Sandy right now. Well, there's two components to the personality based hiring system that I subscribe to. First, I don't have to break my new hire of his bad habits in the field because he doesn't have any habits in the field. And second,

His personality is far more pleasant to be around. Within four months, my personality-based employee, like a learned golfer, will outperform the guy with 20 years of bad habits and big ego. And like Billy Bean, I will pay significantly less money to score a better coworker. And now we're ready to immerse my new employee into our system. It's that simple.

We hire, we train, and the next is we incentivize. Yeah, I found this one interesting. It's really interesting how you kind of work it with your guys. one reason that everyone goes to work and the main reason is money. There's a short list of secondary reasons like quality of the company, friendly environment.

But the bottom line is people go to work because they need to earn money.

And part of the personality based team building system is that number one, I hire all my employees for long-term success. I don't hire, ever hire anyone to get me through a busy season. So everything is long-term basis. And because I'm looking for the undervalued qualities, like friendliness, open-mindedness, grit, discipline, longevity, we're not necessarily looking to hire

within our industry. 

RUSTY DRIPEDGE

It's kind an interesting point, just interrupt you for a second. You talk about W-2 and 1099, because in the home service industry, there's a lot of 1099s, right? Yeah. People you bring on temporarily, you have a big job, you bring them in, you get them from wherever you can get them. It's very common in the home service industry. Really common. Across the board. Roofing, I'm sure. Yeah. Siding. Very common. But you don't do that. I don't do Which I think is a real...

You know, as we talk about innovation, that's what big innovation really is. Cause if your dedication to bringing in good people, keeping them and keeping them through the, through the difficult times. yeah.

BOBBY DOWNSPOUT

 Yeah. And each busy time, it's not a busy time to make money. It is secondarily, but primarily a busy, busy time is a time to grow your company. That's when you hire your two new or three new employees and you use that to broaden your platform so that.

so that when that busy time is over, you've grown your platform a little bit and you don't lay people off. But regarding the incentivized employees,

What we try to do is...

allow our best coworkers to rise to the top. Some of them rise quickly. Some of them don't rise so quickly. And let's face it, there are also employees that at some point in their life just are looking for a weekly paycheck. But there are always those bright stars that rise to the surface and those become our future leaders.

In my company, think we probably have seven or eight of our coworkers that are crew chiefs and mid-level managers that are, their pay is significantly based upon the productivity of their department or their crew. So they're incentivized to show up every day and to develop a good relationship.

with the people within their department so they can produce more because that will result in that monthly bonus being bigger at the end of the month. And as I said, I think we have six or eight anyway of our mid-level guys that are incentivized in that way. It's important to clearly define

how they're going to be incentivized. If your department does this, this and this, then you will receive a, your monthly bonus will be based on gross sales from your department. And that's one way that we do it. And at the end of the month, I do the crunch the numbers and these are the bonus amounts that I put through to payroll.

And it works. Now what happens is these guys start looking ahead on the schedule. They start looking at the guys we have in-house and they start game planning on their own. There's a lot of, you've seen the guys out in the shop. I don't direct anybody. They run that shop. 

RUSTY DRIPEDGE

Yeah, they come in the door at the end of the day and they just start moving stuff around. We got a load today, came in with a bunch of gutter extensions or whatever they were in the boxes there.

I soon as I started hearing the trucks come in, I started hearing that stuff getting loaded. And that's what we're kind of hearing upstairs a little bit. Right. They're loading all that gutters. Yeah. We got a good size delivery today. I should learn the terms for all these different things that you've got out in my garage. I call it gutter stuff. There's a bunch of gutter stuff in these boxes. Yeah. There's some downspouts and elbows. Downspouts and elbows. 10 footers out there. I know it was 10 footers, but yeah. Yeah. Major and crew. Major and crew. And the interesting thing too, to get this thought in.

I can't tell who your crew chiefs are. I've been here a year. I mean, I kind of know them now by name and stuff like that, but there's no sense of that here. It's really kind of amazing that these guys are just, you know, that kind of quality of stuff. You don't see people strutting around. It's amazing, really, the quality of these guys. 

BOBBY DOWNSPOUT

Yeah. Yeah. That's a really nice compliment. I appreciate that. Yeah. From our ...

We have a lot of rookies this year. We grew the company a lot this year. Bought several new trucks and I think we hired about eight guys in the field.

one estimator and two or three new girls in the office. It's been a good year. But of the guys that have been with me in the field for three, four years or more, yeah, it's hard to tell which of the crew chiefs and because they all know what they're doing. Yeah. Yeah. Pretty amazing. Yeah. Good group of guys. Yeah, it is. mean to knock you off your incentive. No, But I had to that in. Incentivized. That's what it's all about. Give that high level

ambitious co-worker, a little more reason to come to work every day, a little more reason to get involved in the day-to-day operations. 

RUSTY DRIPEDGE

One of the other interesting things you do is some of your guys own their trucks. That's a cool thing. That is fascinating. What a great idea. 

BOBBY DOWNSPOUT

Well, I think we own eight Tacomas and we own three box trucks, but we also have five other vehicles that we don't own.

We could lease them, but way back in the beginning, we had an employee that he wanted to use his truck for work purposes. So we worked out a situation where he would be paid a little bit of incentive because he's using his truck in a work environment. And then another one or two guys said, hey, can I get in on that? And we said, yeah.

And way back in the beginning when we were growing the company, this was great because we didn't have to buy all these new trucks. Our coworkers, our employees were buying them for us. And then they were getting incentivized. And I got to tell you.

when a person invests a truck in your company, you got a lifer. This guy's not going anywhere. And he feels like he's a part of the company because he is. He's earned profit sharing. So that's just an added sort of shot in the arm that we've kind of thrown out there. 

RUSTY DRIPEDGE

So because he owns the truck and he's putting his capital into the company, he's getting a share of the profits that that truck makes. Yeah.

BOBBY DOWNSPOUT

After incentivizing, then comes delegation.

Micromanagement is the opposite of delegation. Delegation is a learned skill.

especially for those of us in the trades, because usually tradesmen, like let's say when I was 22, 23, 24, I was a really good roofer. And I was just growing in that industry. I was learning the industry. I was getting better at it. I was learning new strategies and techniques and theories about how to run a job site.

But you can only grow so far if you're doing all of the work. You can surround yourself with a good team, but if you really want to grow, you got to delegate. And that means you got to train people, incentivize them, and then trust them that what you've taught them, that they will be able to take that out into the workplace under your banner, under your name, and do the same quality work that you would do.

Because many business owners are skilled at their trades, it may be hard for them to learn the art of delegation.

Micromanagement is the opposite of delegation and micromanagement is the enemy of growth in business. 

RUSTY DRIPEDGE

And it kills momentum.

BOBBY DOWNSPOUT

It's momentum killer. It is. it also, it's an insult to your coworkers. If you're hovering over them, correcting them and micromanaging them, it's an insult that they don't want to live and work in that environment. Delegation is a must if you want to grow your company. 

RUSTY DRIPEDGE

And it's interesting because...

All the other things are kind of setting up your ability to delegate, right? You can't just delegate in space. You can't hire a new guy and delegate. No, no, no, no, no. It's these other things. goes together. That are allowing you to get to this point where you can actually delegate. You got to hire, you got to train, you got to incentivize long before you delegate. so one without the other. It's almost for all these five items that we're talking about today. One without the other kind of just doesn't, they don't fly. They don't fly. They've got to be kind of done as a sort of a holistic mix, I guess.

BOBBY DOWNSPOUT

Think about this. And if you can wrap your mind, if you as a business owner or a CEO, if you can wrap your mind around the fact that there's nothing we do that is irreversible.

then delegation is a little bit easier. We've hung a gutter wrong before. We just take it down. I mean, maybe we have to scrap it and we lose the scrap value or we lose the value of the 22 pounds of aluminum that we just, but just take it down, scrap it and let's rebuild the gutter and put it back up properly. Happens all the time. We all make mistakes. Don't get upset. I've done it myself. I've measured a gutter slightly wrong. You hang it and you go, you know what?

I cut that gutter wrong. Let's just take it down, scrap it, and put a new gutter. And don't even give it a second thought. Nothing that we do is irreversible. 

RUSTY DRIPEDGE

That's a skill I need to learn as a DIYer at home. The final piece to the team building process is hold accountable.

BOBBY DOWNSPOUT

You know, hold yourself accountable, hold your mid-level managers accountable, and in fact, hold everybody accountable. If you've got a new employee that you just hired, he's got to be held accountable for showing up on time. And then a week or two or three in, making sure his tool bucket and his tool case are fully prepped, loaded, and ready to go.

And that accountability grows all the time. If you have a coworker that shows up late.

We can let that fly. We just mentioned to him, don't do that again. But if it happens twice.

This person must be taken aside and sat down and say, look, when you show up late, there's a lot of repercussion. Your crew has to wait for you. They can't go out. They're sitting around waiting for you. And the customer on the other end who's expecting you guys at eight o'clock sharp, now the crew shows up at 8.15. We look bad. They're disappointed. So accountability is essential.

everybody from the CEO, the owner to the newest employee has to be held accountable. And even our mid-level managers who are incentivized, they must be held accountable. If your department does something that has to be repaired or redone, you have to do it. Don't wait to be told. If it's the customer that noticed it,

It must be corrected.

And it has to be done by that mid-level manager, by that crew chief who made the mistake because it's within his department. So hold your people accountable and hold yourself accountable too, you know, to your people. And, you know, I make mistakes every day. We just correct them, you know, and holding accountable and all levels of accountability are essential, especially early on, you know, when, when my

when my guys come in every morning into the shop, know, got to have your tool bag, got to have your tool bucket, you got to have everything ready to go. Listen, once in a while we all forget something. That's going to happen, but keep accountability as a priority, especially for your mid-level managers as they grow, because then their departments will grow better. 

RUSTY DRIPEDGE

Do you have like a review period or review process or something like that? Or do you check in with them? Or how do you kind of do that?

BOBBY DOWNSPOUT

Well, we have regular meetings. probably have just simple, basic team meetings six times a year. We have safety meetings twice a year. We have small group meetings where I'll take my office staff once a week. I take the office staff probably once a week and we talk about what's going on, areas we can improve upon. One of the things I do is I have a setup in my office where I can

I can get a really good big overview of what's going on in the whole company from the guys in the field to what's going on in the office to a whole lot of other things. And I see things that other people don't see. And so, yeah, I'll pull all my crew chiefs in and just have a crew chief meeting just for 15 minutes. I would say we have at least one meeting a month and in my office probably once a week. So, yeah, I think it's

It's good communication. Yeah. As a small business owner.

I want you to recognize that you are the average of the five people closest to you. I love this. 

RUSTY DRIPEDGE

This is something I read through when we first were looking at this thing. This really struck me. It's a really great line. You got to repeat that again so people can hear. It's really a great line. 

BOBBY DOWNSPOUT

As a small business owner, I recognize in myself that I am only the average of the five people closest to me. And with that said, I want to surround myself with the best people.

I want to surround myself with the best talent available. Successful business owners know that sevens and eights hire nines and tens, and they know why. And the low level business operator.

He doesn't know that fives and fours hire twos and threes. And even if he did, he probably wouldn't know why. So just remember that as the owner, you want to be that little squirrel under the hood that nobody sees. You want to be the hub surrounded by the five or six or seven most talented people that you can surround yourself with. And to find those people, you don't.

you follow this process to hire the train, the incentivize, the delegate. I have a funny, sort of an interesting and recurring story in my life. I have a friend who is a very, very highly skilled carpenter from frame to finish. This young guy can do it all and he has a team of three really good skilled carpenters around him.

I've worked on job sites with these guys. I know this team pretty well. And I would say in the trades, my friend and his three coworkers, they're probably sevens and eights and nines. They're really skilled guys. And their pay bangs around $40 to $45 an hour, which puts them, you know, if you

push that through payroll. They're in the $50 to $55 an hour range when you add in FICA and payroll taxes and other things. Yeah, it's costing him $55 an hour to keep each of those guys on payroll.

And every once in a while, every two or three years, there'll be a little bump in the road and all the builders that he frames for and does trim work for and stuff, they'll sort of kick him to the curb because he's a 1099 company. And he and I were talking a couple of weeks ago and he was telling me that, you the builders are now only paying $65 an hour per man and it's costing him $55 an hour per man.

And there's not a whole lot of profit there. And when I tell you his guys are skilled, I mean it. These guys are very skilled, well-oiled machine. There are a couple of sevens and eights and nines and they do beautiful work. But on any given day at $65 an hour, that team is only generating $520 per man. That's basically a little over two grand for a four man team.

And they're only turning about $320 of profit back to the company because they're collecting $65 and it's costing them 55 to keep that guy on payroll. They're only kicking $300, $320 back to profit.

I have a group of really great guys at work for me and some of them don't have great skills in the trade. They only have great skill for our style of work, much like Scott Hattaberg and Davey Justice who played baseball for Billy Bean in the 2002 Oakland A. They were not wanted anywhere else in the league. They were cast aside. They were kicked out. Billy Bean picked them up and turned them into a winning program.

That's the kind of guys we have. know, if I look at one of my crew chiefs who used to run a restaurant and now he runs a gutter cleaning crew and he has an assistant who just came on two months ago, their skill set doesn't compare to sevens and eights and nines. And yet they go out and they can produce $2,400 per day per crew.

So a four-man crew can go out and produce almost $5,000 in revenue per day, and 70 % of that gets kicked back to the company in the form of profit. I mean, that's how we can incentivize our guys, because we've created a high-margin industry, as opposed to those highly skilled carpenters that are in a very low-margin industry.

The highly skilled carpenter doesn't produce nearly as much revenue as my team of Square Pegs and Misfits and JV players. We got a team, really, I love Square Pegs because I feel like I am one. We got a team of Square Pegs and JV players that kick the crap out of everybody else's varsity. 

RUSTY DRIPEDGE

Sort of like the 2004 Red Sox. Yeah. See my hat. Yeah. I brought my hat today. It's sort of like that team.

I mean, the show on Netflix now, The Comeback. Phenomenal. Phenomenal show. yeah. Love it. And the locker room scenes are what I just absolutely love. I mean, they come across as you can understand sort of the chemistry, like you talk about the square pegs, the misfits, and how they came together and won a world championship. It's a pretty amazing story, which is kind of what you're doing. I mean, in the terms of gutter world ...

I think you're winning the world championship pretty much year after year, certainly on the Cape. And now as you kind of spread out, American gutter monkey spreads out and starts putting franchises in other areas kind of the same, 

BOBBY DOWNSPOUT

on the island of the blind, the one-eyed man will be king, right? And 10 years ago, gutter cleaning on Cape Cod simply didn't exist. Gutter cleaning on Cape Cod was the island of the blind. I mean, we came in.

We didn't have a platform for it. There was no business model for it. And in fact, when you talk to people, I remember you were telling them stories about people and they were saying gutters, going to go, you'll never make any money doing gutters. You'll starve. Yeah. Well, of course I told this to Andy, to my partner Andy. He, he came out of the corporate world. He was VP of finance for a large company and he left to clean gutters and I was a retired builder.

with a pretty good skill set and we decided to clean gutters. And yes, here's what Andy's, a few family members kind of said, you're wasting your talent. What are you doing? This is never gonna work. You'll starve. One of my contractor friends said, there's not enough gutter cleaning on Cape Cod to keep two guys busy all year long. 

RUSTY DRIPEDGE

How many employees do you have now?

BOBBY DOWNSPOUT

I think I counted 29 the other day. I how many trucks and we have a lot of trucks. 

RUSTY DRIPEDGE

Got a brand new two brand new Tacoma sitting out in the parking lot. I just saw it was beautiful. 

BOBBY DOWNSPOUT

Yeah, actually this year we we grew a lot. We bought four new trucks this year. I think we have about 15 or 16 trucks. But the thing is 10 years ago. Gutter cleaning on Cape Cod was the island of the blind, and that's where great opportunities exist, where nobody has ever gone.

That's one of the reasons why I think we were so successful so quickly is because we saw an underserved market. And just to give you an idea, this is about 10 years, right? We just passed our 10-year anniversary. Yeah, 10 years. You and Andy to what the size of the company is now, 30 employees. Yeah, we started with two guys and we reached 55 at the time. 55-year-old guys, we were getting ready to retire. 

RUSTY DRIPEDGE

And half your business is

BOBBY DOWNSPOUT

It's We're about 50-50. Which is Right about 50-50, yeah. You'd think as big as you are it would be all installations, but it's not. 50 % of it's cleaning. It is. It is. And it's real, it's fun, it's cool, it's a little cyclical. Yeah, there's a lot of really, really good stuff. Yeah, recession proof. People need their gutters cleaned. We keep speculating that there's some level of recession proof built into gutter cleaning because it's maintenance. Yeah.

It's $240 once a year. There's your typical scenario. One final note on incentivizing and team building. Years ago, many, many years ago, my wife and I bought an inn. She was pregnant with our oldest son, who's now almost 40. 

RUSTY DRIPEDGE

Giving away your age here.

BOBBY DOWNSPOUT

I told you 10 years ago, was 55. 

RUSTY DRIPEDGE

yeah, you already did. You already blew our cover shit. I spent all this money on these fancy lights to make us look young and now you've gone. 

BOBBY DOWNSPOUT

One of the three day-to-day components of the in business, the kitchen, the dining room and housekeeping. I used to run the kitchen. My wife ran the dining room and Barbara also ran

housekeeping, but it's too much for one person or two people. So we had a difficult time hiring and keeping housekeeping people. We would hire people in the industry. They've got a great resume. They used to work at the Mount Washington. They worked at the Mountain View. They worked at the Spalding. And we would bring them in and they were slow. They were unmotivated. They couldn't complete.

the entire housekeeping tasks for the day in the eight hours that they had. invariably, Barbara and I would have to go up and put away what we're doing and go help them and try to bail them out. And it was interrupting the other processes that we had going on.

Really, a team of two girls just couldn't seem to find two ladies that could do eight hours of work in eight hours. We were paying them by the hour, the going rate, and they just couldn't seem to get the work done. And then we saw an ad in the newspaper, our friend Debbie, Little Debbie's house cleaning or something like that. We interviewed her and we hired her.

And she would come in with an assistant and they would do the eight hours of work that would take the other ladies 10 hours to do. And Debbie and her assistant would come in and they'd knock it out in two and a half hours because they weren't being paid by the hour. They were being paid by the job, by the room, by the task. was piecework. And they would complete an eight hour day in two and a half hours, three hours. And we never had an issue because they were.

streamlined, they were organized, they worked together. I mean, it was a thing of beauty. And Barbara and I never had to assist them. And we never had issues. The towels were done right. Everything was beautiful. And there were two reasons. Number one, we didn't go through the normal hiring process. We sort of colored outside of the lines a little bit. And the second thing is we didn't pay them in the traditional hourly rate.

We said, hey, here's the tasks for the day. Here is the pay scale. And they would knock that thing out in record time. And pretty soon we got used to it. And it freed up so much time for Barbara and I because we didn't have to pay attention to it. We didn't have to worry about it. it was kind of setting up that win-win thing again, right? You guys won because you got your jobs done, got them done on time, and they won because they could move.

at their speed. yeah. Get their jobs done and move on. And they had other clients. And move on. They had to get going. And what a great relationship we had. Debbie and her team, they worked for us right up until the time we sold the inn. That was back in 1995. And I'm sure they stayed on when we were done. But that was the first time, and I was a young guy back then. I was probably 28, 29 years old. That was the first time I really went outside of the normal

process when it came to hiring. But I learned a lot. I learned a lot. I went and I got back in the roofing trades a few years later. Right away, I kicked that into gear. And it's been working for me ever since. 

RUSTY DRIPEDGE

Yeah. That's interesting. All right. We've covered your five steps. We've covered Moneyball. Covered Moneyball. If you get a chance, go see that Netflix documentary. The Comeback. 

BOBBY DOWNSPOUT

The Comeback. Amazing. Really good.

RUSTY DRIPEDGE

Really good. Although I apologize to any of our listeners out there that might be Yankee fans. To the point where they might have just shut us off. 

BOBBY DOWNSPOUT

Nah, that's okay. That's okay. It's a great story. 

RUSTY DRIPEDGE

Yeah, it is a great story. Thanks everybody for listening. Yeah, it's been a great show. Thank you very much. That's our first episode. More to come. A lot of the subjects we kind of touched on will expand on our next couple interviews. We'll have some people in to talk to. We'll have a live stream at some point.

We'll have some links to the website where can see our episodes and email address where you can email us with any questions. It'd fun maybe to do an episode every once in a while with questions we get from the crowd. 

BOBBY DOWNSPOUT

No monkeys were harmed in the making of this podcast. 

RUSTY DRIPEDGE

That's right. All right. Talk to you later. Thank you. Bye.