Every growth leader hits a pivot. Few call it out. In this episode of The Midgame Mindset, Bruce Leffler—sales veteran turned agency founder—takes Rich Bishop (and us) through two of his defining midgame moments: the risky choice to leave steady work and the leap from top seller to Founder of a niche agency. The result is a masterclass in conviction, hustle, and what it really means to lead people up—not just to hit numbers.
Why this conversation matters
If you sell, scale, or lead growth, Bruce’s story lands like practical wisdom. He moves from pounding the Yellow Pages territory in the mid-2000s to closing enterprise deals with IMG Academy and major sports clients, then to founding Best Roofer Marketing. Along the way he learned how to turn personal grit into repeatable systems—and how leadership is a different muscle from selling.
Snapshot of the journey
- Early hustle: Bruce learned sales the hard way—door-to-door mow jobs at eight, then phone-book sales at 25. The move to BellSouth/YellowPages wasn’t glamorous. It was strategic. He risked a lower base for a higher on-target earning and says bluntly, “I bet on myself.” Year one? $132,000.
- Digital pivot: As the market shifted in 2008, Bruce doubled down on digital marketing. He saw the decline of legacy channels and the rise of internet-first strategies—and moved faster than many of the “old dogs” in his office.
- Enterprise playbook: Landing large clients like IMG Academy taught him persistence and the importance of service. He walked through security gates, dropped collateral, and won meetings. The lesson: enterprise buyers expect professionalism, patience, and a longer sales cycle.
- Leadership transition: A top seller does not automatically become a top leader. Bruce describes being championed into leadership by a fearless regional manager and learning to trade short-term wins for long-term team development.
- Entrepreneurship: After years in corporate roles, Bruce bootstrapped Best Roofer Marketing with roughly $3,400 and a dirt-cheap website. He hustled, leaned on relationships, and built a white-glove agency that works with a limited number of roofing companies to deliver consistent results.
Key discussion points and takeaways
1) Bet on yourself—but calculate the runway. Bruce left a corporate career after building a modest nest egg and part-time clients. He gave himself a short, realistic runway and went all in.
2) Persistence beats permission. The IMG story is a concrete example: persistence, repeated outreach, and the confidence to show up in person won a tough meeting.
3) Enterprise sales are different: expect longer cycles, higher expectations, and the need to deliver exceptional service. A robust small-to-mid market pipeline is essential while you wait for bigger deals to close.
4) Leadership is a learned craft. Top sellers are often impatient and revenue-focused. Leaders must be patient, teachable, and willing to trade immediate personal wins for team wins.
5) Build a service-first company. Bruce intentionally limited the agency’s client roster to deliver white-glove service. That approach reduced churn and made the business sustainable without needing to scale by volume alone.
“I knew if I spoke to enough people, I was gonna find the opportunities.”
Bruce Leffler
Concrete advice for growth leaders
– If you’re moving upstream to enterprise, brace for a longer sales cycle. Keep a healthy mid-market pipeline to smooth revenue. Activity looks different at enterprise scale.
– If your organization is a “sales machine,” decide whether churn and volume are acceptable tradeoffs. A focused, high-touch model can sustain healthy margins with fewer clients.
– Don’t assume top sellers will naturally lead. Invest in mentorship, patience training, and deliberate transitions. Sometimes the best move is to hire a fresh leader who can build without past role baggage.
Why Bruce’s story is relevant to every entrepreneur
The particulars—YellowPages, IMG Academy, roofing—are Bruce’s texture. The core lessons are universal: conviction, iteration, and the willingness to test your assumptions. Bruce’s second midgame moment—quitting a safe corporate job to start a niche agency—shows that timing and preparation matter as much as courage. He didn’t borrow money. He built sales quickly enough to run month one. That’s repeatable discipline, not luck.
Watch the episode
This conversation blends hard-earned playbooks and candid storytelling. If you lead growth, recruit sellers, or are thinking about starting a niche agency, you’ll find actionable tactics and mindset shifts in this episode. Watch now:
YouTube: https://youtu.be/G5aPoq8TAZo
Spotify: https://open.spotify.com/episode/47iHssefy0cYwaSISAtcdB?si=A_gtwKN6QdiYW4R4E_oJsw
Apple Podcasts: https://podcasts.apple.com/us/podcast/the-midgame-mindset/id1818103399?i=1000743810228
More from Bruce Leffler:
– LinkedIn: https://www.linkedin.com/in/bruceleffler/
– Best Roofer Marketing: https://www.bestroofermarketing.com/
– Best Hustler Academy: https://www.besthustleracademy.com/
– The Truth About Sales and Marketing for Roofers Exposed: https://a.co/d/0BootMM
Host: Rich Bishop — The Midgame Mindset
Want more episodes that surface the choices behind growth? Subscribe to The Midgame Mindset and join us next time for the turning points that shape how leaders win.
Full Episode Transcript
Introduction to the Midgame Mindset
0:00I got to take $3,400 out of an old IRA. And I got my friend to build me a dirt cheap website. And I just I was inching
0:06along doing as much as I could for free. I had already tender my two weeks resignation, started on July 1st. I just
0:11got to go do my thing. I just got to go do what’s worked for the last 15 years and put some things together. And that’s
0:17kind of like how we got started. Welcome to the Midgame Mindset. Join us as we dive into the pivotal moments that shape
0:23today’s top sales and marketing leaders, RevOps innovators, and entrepreneurs. This is where grit meets growth and the
0:30game changes for good. If you find value in this conversation, be sure to share it with another growth leader who would
0:37enjoy it. And now, let’s get to the show. Welcome to the Midgame Mindset. I’m your host, Rich Bishop, and today’s
0:44guest is Bruce Leler. Bruce is a sales executive who’s been in the digital
0:49advertising space for 20 years now. And he’s worked with big clients like the PGA Tour, IMG Academy, Tampa Bay
0:57Buccaneers, the Jacksonville Jaguars, major PE firms, just to name a few. He’s
1:03taken that experience and started Best Roofer Marketing, which is the number one growth agency in the roofing
1:10industry. And you may say, Rich, that’s really niche. Um, how is that relevant
1:16to me? Well, Bruce’s journey here is one that I think any
1:22entrepreneur or anybody that wants to be an entrepreneur needs to hear. There are some really good insights and I can’t
1:28wait to dive in here. Bruce, thank you so much for joining. Hey, good morning, Rich. Thanks for having me, man. I appreciate the intro.
1:34Excellent. Yeah. Now, I hit on just a couple of the highlights. I’d love for you to take us through maybe a little bit more about who you are and what
1:40you’re about. Yeah, I mean, absolutely. I think first and foremost, um, I’m a husband and
1:45father of four, right? So, I’ve got kids spanning ages 9 to 25 currently. Two of
1:51them are young adults down in Florida near you, actually. And, uh, wife that works in healthcare and professionally,
1:58um, as you’ve stated, I’m a I’m a veteran to the digital marketing space, the sales arena. I’ve been doing this
2:04for a very long time. I often describe that’s why I’m only, uh, 44 currently with a face full of white hair. I think
2:10that’s I think that’s what marketing will do to you. I I trust me I I get it. Yeah.
2:17Um for sure. So, one of the one of the areas that we like to start uh is what
2:22we call the midgame moment. And we found that growth leaders have multiple
Bruce Leffler’s Journey in Sales and Marketing
2:28midgame moments throughout their career where they’re faced with a challenge or a decision that they need to make that
2:33they draw upon either experiences from mentors, from books that they’ve read,
2:39from their personal lives and apply it to what they’re doing in on the professional front and end up hitting
2:45new heights. Yeah. So, as I describe that, is there something that comes to mind for you? Yeah, I mean, you know, there’s a
2:51couple, Rich. Um, is it okay to expound upon two? I Yeah, go for it, man. Absolutely.
2:58I think that there’s one early in my um I don’t want to say childhood, but my
3:03young adult life that I was faced with a moment. So, I’ll kind of tell you the story about how I got into marketing
3:09because I think that that’s relevant to um a big Midgame moment. At around the
3:14age of 25, I was living with a friend and his wife. Um, I was working in sales at the
3:21University of Phoenix and I think I was making somewhere in the tune of like $45,000 a year and I was on a break with
3:29this young lady and you know she was uh telling me about her mom’s awesome BMW
3:34and that she lived in West Palm, this amazing house and it started to spark interest and so being a um a kid who
3:41grew up without money I was highly motivated um to achieve that for
3:46whatever reason that was my natural um my natural desire at that time. So I
3:52have this conversation with this young lady and she says, “Oh, you know, you’d actually be great at this. It’s the
3:57phone book. It’s Bell Yellow Pages and yellow pages.com.” And this is back in
4:042005. And uh she made the introduction to her mom. Fast forward um I go in, I get the
4:12interview in a new expansion market, Tampa, Florida. And uh the uh I’ll never forget the the general manager, he he
4:20tells me in the interview, he says he says, “Your ontarget earning is like 85,000.” And I remember I was I was
4:27young, but I was so confident in myself. And I leaned in I leaned in to the guy, right? And I was like, “I’m your guy.”
4:34And I had been told if you get the office tour after the interview, that’s a good sign that happened to me. So the
4:39the midgame moment is um I had I had had a discussion with my
4:44parents and my parents were hardworking individuals but never really achieved
4:50financial success and uh for that reason this opportunity with the 85,000 OTT
4:57it had a lower base salary um than I was currently making at you know at University of Phoenix and 45,000. So my
5:04mother um who was a confidant, she couldn’t wrap her head around
5:11that opportunity. No way is my son with his high school diploma, as smart as he
5:18is and as much as I love him, you given our upbringing, our financial status,
Overcoming Doubts and Taking Risks
5:23going to go make $85,000. And so she was against it. She was telling me I was actually foolish to
5:30take a significant pay cut from like 45 to 28,000. base salary, but I believed
5:35in myself um wholeheartedly and I jumped in and then, you know, year
5:40one had no clue what I was doing and still made $132,000. So, exceeded expectations, made
5:46president’s club, the whole thing. And I kind of felt like I was home. I felt like I had found what I was called to do
5:53um and going against the odds, going against the grains, uh was able to find success. I love it. That’s a great one to to dive
5:59into. I’d love to find out. I know you said that that there are others and I’m sure that we’ll we’ll get into those, but let’s let’s pause on that one for a
6:06second now. Obviously, kind of blue collar upbringing, right? What what do
6:12you attribute that, you know, forget what the rest of you say, I’m going to go ahead and do this because I feel this
6:18is right for me. Like what kind of drove that decision for you? And then once you’ve made that decision, what do you
6:24think it was that really made you successful in that role? Absolutely. Yeah. So, I have always had
6:30a lot of self-conviction and I’m highly competitive. Um, I was a competitive athlete growing up. I, you know, I I’m
6:38the guy that says second place is first loser, right? And I tell my kids that, um, in a joking manner, but but spirited
6:44um, and rooted in truth. And what I knew was as much as my parents loved me and
6:50as much as, you know, I wasn’t poor, like we weren’t eating out of, you know, cans of uh potted meat, but it it wasn’t
6:58the best upbringing for sure. I knew that that’s not the life I wanted at a very young age. And I had always had an
7:04entrepreneurial spirit. I was 8 years old. My best friend was 15 or 13 at the time, 5 years older than me. And we
7:09would walk around and mow lawns. And there’s people that would do that, but at that age, there’s not people that
7:15would do it at $8 to $10 a lawn and make a couple hundred dollars a weekend. So, like I’ve just I’ve always had that
7:21desire to hustle and grow more. And you know, I was I was kind of going through
7:27the job hopping phase, right? Early 20s, a lot of people are figuring themselves out and what they want to be. I was job
7:34hopping to the next level. Every opportunity was title, slight salary change. I was just never complacent. And
7:41what I felt was this is going to put the world as my oyster opportunity in front
7:47of me. Now I have to go capitalize. So I bet on myself and I think that um it was
7:53clearly the right decision. But it was, you know, it was risky. I just I had that self-conviction that I was going to
7:59be successful. I could do this. I could figure it out if just given the chance. And by the grace of God, I was given the
8:05chance and and it worked out. Yeah, for sure. And you ended up rolling that and and taking that confidence and
Transitioning from Local to Enterprise Sales
8:11some of that competitiveness and rolling that into a really good digital advertising career from there after
8:18selling the you know the the actual yellow pages and and the phone books which I still think is hilarious. U I
8:24think it’s a a great way to get started, right? Like if you’re going to cut your teeth, cut your teeth and and learn the hard way,
8:30right? Yeah. No, absolutely. And you know, it’s funny. I I ended I entered that world, Rich, at a pivotal time.
8:37There was 2005, 2006. I’m getting through training. I’m getting out there. Well, 2008 happens and the market
8:44crashes, right? The market crashes on residential housing, especially in commercial housing, and the internet
8:50bmed all at once. And what I was in is a room full, you know, we had 75, 80
8:56employees down at AT&T in one market, 60 in another, and I was bouncing back and forth helping both. So, we had a lot of
9:02old dogs that had made 200,000 back when 200,000 was a lot of money for 20 years,
9:09right? The yellow pages threw money at you. And so, I was faced with a uh kind of a
9:15turning point that, okay, I’m young. Marketing is not going anywhere. The internet’s far more complex than saying,
9:21″Hey, buy this piece of paper for $8,000 a month.” Right? There’s a lot more to it. But I said, “If I want to succeed,
9:28these guys are retiring off. they’ve made their money, they’re going to go retire, they’re not going to learn this
9:33stuff. I’ve got to get into the digital aspect and that digital component. Um, and so that happened two years in, but I
9:40wasn’t going to let that be my uh the holy grail that kills my opportunity,
9:45right? It was like, hey, no, let’s just keep going. Let’s figure it out. And so that’s where I dove deep into the world
9:50of internet marketing. I love it. and you know the the yellow pages you had a um you you had a
9:58specific territory that you were working. Tell us a little bit about your journey because you’ve worked with some
10:04large enterprise businesses in your career. How did you make that transition from local market to enterprise and what
10:12were some of the key learnings that you had along that journey? Yeah, absolutely. I think um a couple a
10:18couple of key learnings but one of the big things was again you know finding these larger enterprise opportunity came
10:25from years of trial error development and really understanding what’s working
Key Learnings from Working with Enterprise Clients
10:31not but also the lack of complacency. So, you know, I just I wanted to be the
10:37best and the best was going to have the opportunity to sell the largest customers, to sell the biggest
10:42commissions, to kind of win the president’s club, be first in market and these type of sales competitions. So, I
10:48knew I had to go after them. And I think where a lot of people get stuck not only
10:53in this industry but in the world of sales as a whole is
10:59that conviction or that belief in themselves is met more with reluctancy
11:04and fear of well what if it doesn’t work? So I had no fear maybe from starting at
11:108 years old knocking on people’s doors randomly asking them if I could mow their yard for eight bucks. I had no
11:16fear of the word no. I moved on. I didn’t take it personal. It was just me. I was just figuring out, but I knew if
11:21if I spoke to enough people, I was going to find the opportunities. And so, I’ll
11:27tell you about the IMG Academy because that was one of the first larger clients I was able to land. Um, we were
11:34territories like you’d said, right? So, I was bouncing between PKL, P, excuse me, I was bouncing between PK County, a
11:41more rural area of Florida, and then Sarasota Manatee County. And I would
11:47live 7 months in Sarasota Manatee, 5 months in Pulk. And we were building these phone books, right? And then these
11:52digital. So I I saw this IMG Academy, beautiful sports complex for anybody that doesn’t know, in Braon, Florida.
11:58People pay hundreds of thousands of dollars to send their kids here to be able to play sports. So I said, “Boy,
12:03wouldn’t that be a fun client?” And I just started hammering them. I had no clue what I was doing. Um, but they have
12:10a security gate campus, right? I was emailing, I was calling. Eventually, one
12:16day I actually showed up at the security gate and just kind of convinced them I had a meeting and got myself in to drop
12:22off some collateral. They took the meeting and then they were highly impressed. But it was the persistency of
12:28um getting through those barriers and getting them to pay attention to me. It it took a lot of leg work, but from
12:34there I’ve kind of, you know, polished up my approach a little bit. But yeah, it took it took a lot of grit, man. A
12:40lot of a lot of cojones to to just walk right in. What was what was that like? What were you thinking when they
12:46actually let you in that time? You had been trying to get in for so long, when they actually opened up the gate, what
12:51what was the thought? Oh, God. Like, what am I going to do now? Right.
12:58And uh you know, it’s kind of I think I’m not the gift of gab, but I can sell
13:04myself out of a paper bag and a lot of people can. So, I I showed up. I had some things to drop off. I don’t
13:09remember the details of what they were. um I’d offer to take them to lunch or whatever it was going to take just to get them to hear me. And they said,
13:15″Look, you know, we’re very busy right now, but here’s what I’ll do because of your persistency. We have seen, you know, your persistence. We have seen
13:21your emails. Um we’ll set a meeting with you.” And then I walked in young solo
13:26and they had like five people in the room. And they were taking the meeting very seriously and I had to put on my dog and pony show um and leaned into
13:35uh really just telling the truth with conviction and confidence. Um, and that worked and that spiral into a really
13:41great project. It was pretty exciting. That’s fantastic. Such a great way to All right. Now you’re in the enterprise
13:47space, right? You’ve got this this massive client. You then have gone on to uh work with a number of other larger
13:54clients, a lot in sports, but also also other industries as well. How did
14:00working with those enterprise clients after IMG um start to change your
14:05mindset if at all around how you approach a sale? Yeah, I mean I think you know there’s a lot of discernments
14:12or differentiators but you have to understand the difference between the expectations right in a small business
Navigating the Differences in Sales Expectations
14:18expectation is buy your product and or service make a material ROI or a rorowaz on their ad spend or whatever enterprise
14:27the expectation can be completely different. Yes. Um they’re expecting a return on their money. That’s kind of
14:33table stakes, but they’re expecting a high quality of service and professionalism and responsiveness and
14:39you know, you have to bring your customer service game and your ready response and and all of those sort of
14:44things that you may not have to deal with as a small business customer. But
14:50enterprise is, you know, a higher risk, higher reward to get the opportunity, but then the real work begins once
14:55you’ve landed them that you have to lean into the deliverables. Uh, but I would say that, you know, the small businesses
15:01may have a little bit more of an emotional attachment to the money, right? It could be like, hey, I give you this two grand or I I put this two grand
15:07in my paycheck. Um, at the enterprise level, what I found is that they’re not financially tied, you know, they’re not
15:14emotionally tied to the financials. It’s a business decision. And because of that, you know, your job is to make
15:20their lives easier, give them all the credit, that sort of thing, right? And so as I started to figure that out and
15:26unpack that with IMG and some larger, you know, multi-reional accounts, I was able to really connect the dots and put
15:33the pieces together. So that way, not that I was really leaning into just one angle or another, but that it opened up
15:40more opportunities for me as a whole. So if I felt like I wanted to sell something, I knew how to take the right
15:47approach to deliver the right message to the right person at the right time. That’s great. There are a lot of companies and and I’ve worked with a
15:53number of startups as well that are kind of going through that transition, right? Where it’s when you start off with a
15:59product, especially in the tech space, right? You’ve got um maybe smaller customers that you’re working with and
16:05then you want to work upstream and what it takes to work upstream in that enterprise space as a different type of
16:11sale, a different type of conversation and a different level of service. I think you you hit the nail on the head
16:16there. um I as you know people are making that transition, are there any
16:23other kind of key um uh bits of advice that you would give from your experience
16:29in making that transition to to other things that people should be thinking about? I would say that, you know, if
16:35you’re trying to make the transition from small to mid-market up to the enterprise level, one of the things you
16:41need to do is have a full and robust pipeline of small to mid-market because the enterprise level moves at a totally
16:47different pace, which is significantly slower. Whereas a small business owner, you know, you can meet with them today
16:53instead of follow-up meeting for tomorrow and they can give you a disposition, right? You’re talking about smaller ticketed stuff. that followup
16:59with an enterprise account might be two to three weeks out just to get a very small meeting on the calendar to
17:06continue to move the progress forward. So, the length of the sales cycle expands drastically as you go upstream.
17:13And if you’re used to going out and the thrill of the kill and the constant chase and being able to close business
17:18on a weekly basis, you’re going to want to satisfy that itch not only from your financial needs, but really from just
17:23the activity level that you’re accustomed to because it can be hard and a little bit worrisome, right? To say,
17:29″Hey, I’m I’m leaning in on this account. It might take four months.” And then, oh, what if it doesn’t come through? Yeah. You don’t want to be stuck. That
17:34can be a roller coaster of of emotional ups and downs as well as financial ups and downs, right?
17:41Absolutely. Yeah. So, you were working the the yellow
17:46pages, you then worked at um a few other agencies in the in the digital marketing
17:52space. Um as the technology changed, Google
17:57obviously really took over. Google is a big part of what’s going on in the in the digital marketing space. um how did
18:05you then make the transition or or what happened that led you to then creating best roof for marketing?
18:11Yeah, that’s a great question. Well, and you mentioned Google as an aside before I go further, you know, 20 some odd
18:17years ago, right? I was early 20s. Um and I was just getting started, so I
18:22really didn’t have any financial assets to speak of. But then a lot of these old dogs, I know a lot of multi-millionaires
18:28now that invested in Google stock 20 years ago, um that you know, I think
18:35that’s going to be like AI stock for us, right, when Open AI goes public or something like that as well. How did you make that transition from uh
18:43being in that digital marketing space kind of as a as an employee? Maybe we go to um how you then became a leader and
18:52what it was like to be a leader. Let’s let’s go there. Let’s talk about your your transition to being an from an
Leadership Journey and Mentorship
18:58individual contributor to being a leader of teams and what were some of the key learnings there?
19:03Yeah. Yeah, it’s a great question, Rich. So, when you think about my leadership journey, it it may be like many others,
19:10right? I I had the privilege to again with that um itch to always get more and move up and do better and and higher
19:16earning potential work at some of the largest agencies in the world. So, I’ve worked at AT&T Bell South. I worked at
19:22Reach Local, who’s now really Scorpion 2.0. 0 uh worked at AOL and then worked
19:27at web.com and along that journey I was blessed with some really really really good mentors and some really bad ones
19:35and I would say both are a blessing right because it allowed me to figure out who I wanted to be and who I didn’t
19:42want to be which I believe is equally as important does that make sense sure does I read a lot of books um I have a enough
19:50to publish a library at home heavily in the sales and leadership ship space and
19:55I read so many that you know you read 300 pages to take out one small nugget that starts to get tiresome and what I
20:02found is that there’s a lot of similarities on a lot of the paperbacks that are out there’s a lot so
20:08I started to create my own process I started to create my own methodologies and then what really triggered my
20:15transition to leadership was a desire to implement
20:20I had gotten to the point where I really say even kill. I wasn’t emotional about money. I didn’t care because I was
20:26making money. I didn’t care um if I lost a deal. I didn’t care if somebody signed. It was just kind of foot on the
20:32gas all the way to the floorboard 100% of the time. And if you have enough activity, they’re going to drop. But
20:38what I found is that I could really, really, really sell digital marketing. And then I started leaning into, you
20:45know, getting tapped on where there was no title change, no compensation change,
20:50but these, you know, my sales leaders, hey, would you go ride with so and so or
20:55would you go take out so and so or will you go help so and so with this bigger opportunity? And I started closing for
21:00other people, which I had no problem helping them out. But at some point, I started to put the
21:05pieces together that, hey, um, I’m teaching them on the side. I’m being asked to teach them. I’m demonstrating
21:13for them. I’m conducting, you know, solidified MR for them, right? Real revenue that’s
21:19on a recurring basis. Not only I’m not getting compensated for, but I’m not really getting credit for what’s working
21:27that I’ve created, right? And so I think um I wanted to get into the leadership
21:33so badly and at a couple of organizations and I now I don’t want to get too specific or call them out by
21:38name because I’m still friends with some senior leadership but they were kind of holding me back. I
21:45was stonewalled right for years. Your time’s coming. Your time’s coming. What they were really doing though is saying
21:50hey this guy sells so much. I don’t want him to stop being in responsibility of sales.
21:55And that was a hard pill to swallow. And so eventually I was given my
22:01opportunity. I was given my shot to lead a team of people um at web.com
22:06and we just kind of crushed. It took off. Um and it was a lot of fun. And you
22:14know again when you’re starting to make money it really doesn’t come about the money. It’s how do you spend your time? Are you you know getting that
22:19intellectual curiosity satisfied? Are you um excelling and helping other people in the impact? And so when I
22:27started to impact other people’s lives and their finances that I knew went to their family, I was kind of like, okay,
22:32this is my next call, right? I really want to lead. Um, it’s not that the sales wasn’t good or lucrative. It’s
22:39just when you do the same thing so long, it’s not really fun. And again, it was a
The Transition from Individual Contributor to Leader
22:44opportunity to test myself and see if okay, I can sell, but I know that not
22:50every seller, great seller is a great leader. So, can I get other people to follow me and can we have success on a
22:57larger scale? Um, and it wasn’t easy, right? It it wasn’t easy. There was a lot to learn, but again, I tried to
23:03spend a lot of time reflecting on uh both things that I liked and loved from some of the best and things that I
23:10despised from others and made sure I built my own way about doing things. Are your go-to market teams built for
23:16scale or are they stuck in chaos? At Midgame Consulting, we turn high growth
23:21challenges into operational wins. From sales strategy to CRM to process
23:27optimization, we help you get it right so that your organization can grow as your topline grows. Let’s transform
23:34today’s change into tomorrow’s success. Visit midgame consulting.com. That’s
23:39midgame consulting.com. Yeah, you’re you’re hitting on something that has come up now a handful of times
23:47in some of the some of the episodes that we’ve done with with other sales leaders is that um the there is a major
23:54difference between being a top individual contributor and a top rep and
24:00making that transition to being a leader. And one of the common mistakes that is often made by organizations is
Transitioning from Sales Rep to Leader
24:07that they see a top rep and they go, “Oh, well, he must be a leader, so let’s put them in a leadership position.” Uh,
24:14and that ends up falling apart because they don’t have what it takes to be a leader. So if if we were to distill it
24:21down into maybe a a couple of points, what would you say makes the biggest difference between that a a good rep or
24:28even a top performing rep that can make that transition to being a good leader versus somebody that really should just
24:35stay an individual an individual contributor because that’s where their strength is. Yeah. I I think one of the biggest
24:42things that jump out at me is that if you want to go from being an individual contributor to an individual leader, you
24:50really have to have a good mentorship in place. You have to have encouragement from the top of people that want you to
24:55succeed and want to propel your career and not hold you back because good leaders in often cases are fearless,
25:02right? And so when I was going up in my organization, my regional manager, he knew that it was
25:09going to be a pay cut for him just based on the millions of dollars in top line that I was selling a year. He still
25:14catapulted me. He was my biggest champion. Um he encouraged me. He told me I was going to be successful. and he
25:20was fearless because he knew that he could hold me back politically,
25:25keep me suppressed to sell for him and kind of run me ragged or he could really
25:31prop me up. So, I I would say that’s one thing and we see this a lot in the roofing space, right? As you know, best
25:38roof for marketing and the coach there. Um, we joke as a coach in the industry that the roofing training is, hey, go
25:44get in the truck with Tommy for two days, follow him around, he’s our top guy, and then go figure it out. And that’s probably the worst thing you can
25:49do because I’ve also found along the way most top sellers are not top leaders,
25:56right? It takes a different side of the brain to be able to slow down, train,
26:01articulate. Um, most top sellers are impatient. I’m very impatient, but to be
26:07a good leader, you need to be extremely patient, right? And so, a lot of these characteristics, you almost have to
26:12teach yourself. It’s like, you know, people say they wear different hats and you can wear different hats throughout the day, but I think you have to
26:19purposefully know which hat you’re wearing and why in order to be effective because you, you know, you can be very
26:26successful being impatient in sales as a hard charging um nononsense kind of guy
26:31that’s just running after talking to a lot of people and finding success. But you can’t lead like that,
26:37right? And you have to meet people where they are. You have to be able to find their gaps. you have to be able to um not only deploy that patience, but
26:43really the continual training and learning to teach them um how to lead.
26:48And you’re going to have to have the charisma to have people to follow you. And I think that, you know, if you don’t
26:55have a good what I would call clean bill of health as you’re coming up as a seller, um it may be hard to take a
27:03promotion within the organization. it it may be best to start that leadership journey somewhere fresh uh where less
27:10people know you because a couple of things are going to you know happen. One, they’re always going to view you as the sales guy whether you treated them
27:16well or poorly. You were just a top salesperson and you know maybe they already resent you a little bit and
27:22maybe they feel like you’re not the best leader. Um that you were just a really good sales guy but you don’t belong in
27:28that role. So that resentment turns to disrespect, um, disobedience, insubordination,
27:34whatever, right? They’re not wanting to follow you. So, you know, sometimes it’s okay to get
27:40to your pinnacle and then, you know, make a clean jump somewhere else. Yeah, that makes a lot of sense. And you
27:45hear about that in other industries and in other places, too. Even, you know,
27:51sports and music, right? The people that grew up with that mega artist is like, “Oh, that’s just Bobby.” like he he it’s
27:58still weird that he’s up on stage, but everybody else is just in awe of of what they’re doing. I think I think you’re
28:04you’re saying something similar there that once somebody kind of pins you as the sales guy, for you to then be a
28:10leader, it it breaks the mold that they kind of have in their own mind for you and and what that looks like. And it’s
28:17it’s hard to break out of that in that environment sometimes. Yeah. I mean and it could be that you are the best leader option and that you
28:24are doing everything right but you could still carry a stigma from the past relationships of you being in a previous
28:30position. You know one of the other things that comes up as you or that comes to mind as you’re saying this is um nobody in an
28:39organization is more competitive on the whole than salespeople. Right? salespeople just by nature are going to
The Competitive Nature of Sales and Leadership
28:46be competitive whether they were athletes whatever it happens to be and it it is a different switch to flip when
28:54I’m competitive because I want to win and the viewpoint and the mindset of I’m
28:59competitive and I want the team to win that’s a very different thing and I think that’s what you’re describing here
29:05when you talk about that transition to being a leader it’s not necessarily that I want to win for me because you have to
29:12sacrifice yourself if you’re going to be that leader to have the team win. Right. Right. Yeah. I think that, you know, so
29:19many sales people chase the money. And I think the the people that can cut through the noise and are going to be
29:25the most effective leaders chase the opportunity to do the right thing knowing that if they do everything right
29:31for all of those around them and build them up, the money is going to chase them down, which is actually a lot better way to go about doing things. Um,
29:39it’s just a hard pill to swallow because we’re self- serving by nature, right? I mean just in general psychologically we
29:45are all self-s serving people and we want to look out for ourselves first whether we’re going to admit it or not
29:51that’s the way we were wired right survival of the fittest and so forth. So I would say that you know when you can
29:56really whether it’s through you know whatever um prayer or coaching or start
30:04to reposition how you think about hey if I can impact these XYZ individuals lives
The Importance of Selflessness in Leadership
30:12I’m going to be in such a better place and that’s going to accomplish so much but that’s a hard thing to go from hey
30:19it’s all about me me I want to be first I want to be the best I want to have the highest sales I I want to have the highest commissions. I want to make the
30:25most money. Whatever to I want all of my people around me to be better than me.
30:32And you have to almost start thinking like you would for your kids. Now, I think a lot of people think about that for their kids. I have the privilege to
30:38know you on a personal front as well. And I know that as successful as you are, you would want your daughters to be
30:4510 times 100 times more successful than you could ever have dreamed about being. And that’s the same kind of mentality I
30:51think we have to take as a leader, right? We have to look at our people a little bit differently. Kind of treat them like a family in some cases. At
30:57least in my world. It may not apply to everybody, but look out for their best interest. Just knowing that if you stay
31:03the course, you’re consistent, you trust the process, it’s going to pay dividends to your advantage.
31:08You hit on something that is is really critical. And I think especially now we
31:14talk about generational differences and and how people act and we like to put, you know, Gen Z in a bucket or
31:20millennials in a bucket, right? Setting that aside for a second, I think there is an important mindset um that you’re
31:28talking about here that is important and that the principle of do the work well
31:34and the money will follow and trusting that that will happen as opposed to the
31:39opposite way that you you can hear about it from time to time, especially with younger people who haven’t been in this
31:45situation before, is they want the money upfront and then they want to do the work. give me the money and then I’ll do
31:51the work. The real world doesn’t work that way. You got to put in the work and and deliver the value and then the money
31:58will follow after that happens. Especially with consistency and trust over time.
32:04100% man. And I mean that goes back to you know me saying that hey I learned who I wanted to be and didn’t want to
32:10be. That’s not only as an individual, that’s as an organization, right? And I think that our organization, Best Proof
32:16of Marketing, is completely unique because I worked for the largest agencies in the world. And if you
32:22understand how they operate, they’re really just glorified sales machines, right? Hundreds of sellers, you know,
32:28dozens and dozens of states and markets that they’re out there tackling new customers. And if their customer falls a
32:36ride, they’re discouraged and they say, “Hey, um, I’m going to cancel or I I’m not happy with how things are going.”
32:42That sales machine, that organization goes in their CRM, flags them, hey,
32:47unlikely to renew. We got to make up their churn. We got to make up their lost revenue this particular month to
32:53stay ahead so we can continue to go to our, you know, shareholders. As a small business, I knew I didn’t
32:59want to be that. So we’re unique that we’re only working with a hundred roofing companies nationwide on their
33:05traditional growth platform at a time because that’s completely different. That’s a high service white glove level
33:13of customer service, high resultsoriented business that we don’t
33:19lose a lot of customers because of that approach. So therefore, we don’t have to be the next web.com, right? I don’t have
33:25to have thousands and thousands of customers to be successful. We can have our 100 customers knowing that 98.99 are
33:32always going to be happy. It’s a couple of small fires to put out a month and you’re winning on relationships and
33:38business and that’s how they stay with you. So, I think you could skin the cat a couple of different ways, but I think that some of these behaviors not only,
33:44you know, apply to me personally as the individual, but they also apply to how organizations are run, right? Are you a
33:50sales first machine or are you a service and resultsoriented machine? And those two do not directly
33:56align. Oh, that’s a really good point. and and you’re starting to tease a little bit of of where you are. There’s a big
34:03transition here from being at Web.com and some of these other larger agencies
34:08that you talked about and being a strong leader there. There are a lot of sales
34:14leaders that are considering starting their own thing, whatever that looks like, consulting, an agency, whatever.
34:21Uh there are a lot of people that think it that want to do it that that you know that constant when I grow up this is
34:27what I want to do type of mentality but you actually did it and you made some bold freaking moves in order to do it.
34:35I’d love to hear a little bit more about how you decided to go ahead and make that leap and then what were some of the
34:40decisions that you had to make in order to to put that in place? Yeah, that’s that’s great. And that’s you know I I had teased early on that
34:46there was two Midgame moments and this is the second big one, right? So um I was about 14 15 years in my corporate
Taking the Leap: Starting a Business
34:54career with the last two years or so finding the most success in sales and
34:59compensation but also the most dissatisfaction. I just wasn’t enjoying what I was doing for a number of
35:05reasons. One, I was burned out. Um I was being held at a certain level and I
35:11still wanted to go higher. And so I had kind of realized a couple of things to be true in my life. um I only had a high
35:17school diploma and to go any higher in the corporate career um regardless of my
35:23accolades was going to be supremely difficult not within my current employer but also outside you know where these
35:29se-level jobs are requiring a bachelor’s degree a master’s degree in many cases and so I was feeling it really really
35:36really called to do a couple of things um ironically I had just built my wife her dream home in Apollo Beach Florida
35:43um we built it from the ground up we enjoyed the process and going through through that. I had the title as the NSD
35:48at Web.com. Um had a quart million dollar salary and I was life on paper
35:55from again the kid from the mobile home park. Should have been pretty good. He should have been happy, right? Beautiful
36:00wife, lovely kids, brand new house, good income. And I wasn’t happy.
36:07And I knew that I could do more. I knew that there was more left in me, but it was going to come with extreme risk,
36:14right? extreme risk, big rewards kind of thing. And so through prayer and discernment um and approaching my wife,
36:21I decided a couple of things were going to change. We were going to move to Atlanta and I was going to put a path in motion
36:29to start my own business. And uh you know, it’s funny, my wife is
36:36Spanish, she’ll tell you how it is. And I approached her and she still tells the story today. She’s like, “Look, if Bruce had come to me and said he wanted to
36:42open up a, you know, coffee shop or a men’s clothing boutique or anything else other than a digital marketing agency,
36:50it would not have just been a no. It would have been a convicted hell no.” Like, no, no way, right? But it was an
36:58easy yes for her because she had the privilege to watch me for, you know, 15
37:03years go on this journey. And what she said really stuck up the most for her to make the decision easily was not that I
37:08was just good at sales, but we started to forge relationships with a lot of our clients and um personal relationships.
37:14We would go to church with some, we would see them in the community and they all loved us and they loved me and they
37:20knew that I was genuine. And so she said, “Not only do I think you can sell this at a high level, I think your
37:25customers are going to stick with your with your processes.” So she was on board. Fast forward, we transfer up here
37:32with Web.com. Um, but I was free to live anywhere I wanted in the country. Decided I was going to leave and then I
37:38got smacked with the well, you know, you really can’t open due to the NDA where
37:44they were still enforcable or the non-competes. You can’t really do your own thing for a year anywhere in the
37:49country. So, I had to take a job making a comparable salary at um, Century Link,
37:56which was in the IT space, director of sales job. Was miserable for a couple of reasons. It was a great company, great
38:02great benefits, great salary. Um, I had been doing marketing for so long. This
38:07was really trying to teach an old dog new tricks in his, you know, mid to late 30s. And it like marketing is a very
38:13complex space. So, I go in, we have some success. It’s about month 15. Um, and
38:19I’m just still not satisfied. And I had slowly been doing the night, evening,
38:24lunchtime, weekend hustle to build a small client base. And I built a nest
38:31egg. I think I’m safe to say this, right? We’re outside of all of those um you know those years of non-competes. I
38:38built a small nest egg saying, “Okay, I’m used to making this much, but this is how much it actually takes my operation to run at home. Mortgage, car
38:47payments, kids activities, wife’s way of living or whatever.” And there was a minimum number. And so I had, you know,
38:54started to sell on the side discreetly um some marketing services to past clients, new clients, referrals, work in
39:00the Facebook groups. And I didn’t spend a dime. And then I got to where I could
39:06afford to run my operation for five months. And I said, “Okay, I’ve built up a nest
39:11egg where I can comfortably leave and I’m going to make this bet on myself knowing that I have a short runway to be
39:17successful.” So effective effect effectively, I take $3,400 out of an old IRA. That’s what
39:24our company was bootstrapped of. And I got my friend to build me a dirt cheap website. And I just I was inching along
39:30doing as much as I could for free. Um and I said, “That’s it.” And so July 1st, the very half point, middle of the
39:38year, I had started my new business. I had already tender my two weeks resignation, started on July 1st. And
39:45I’m very proud to say that we’ve never borrowed money from anybody. I’ve never
39:52had to use any of that initial five-month nest egg savings. I sold through what I needed to run my
39:57operation the very first month with that full-time effort. And I don’t think it was luck. And I
40:03really don’t think it was skill. I think it was that I had so much pent up energy
40:09from being suppressed in corporate America for so long that I just kind of busted out of a can, right? You know
40:16those cans of confetti you pop at at birthday parties for kids? That’s what I felt like. I was like wasting no time. I
40:23was hustling. I was talking to everybody. I was hitting up friends and family. I was facing tons of not only
40:31rejection but where people want to support you but from afar as a small business owner like I got your back. I’m
40:37gonna cheer you on but I’m not going to give you a dime. I don’t need your services. And so I had a lot of that um from afar
40:44love. But then I kind of just settled in probably the second week and I was like I just got to go do my thing. I just got
40:51to go do what’s worked for the last 15 years um and put some things together. And that’s kind of like how we got started.
40:58That’s such a good story. And again, you bet on yourself big when other people would have thought you were crazy. At
The Journey of Entrepreneurship
41:03first, it was was your mom and taking that sales job. And and now it’s it’s other people around you. Luckily, you
41:09have the support at home, which is obviously the most important in making that transition. And and to be to be
41:15fair, um we have been friends for a while. When you told me you were doing this, I thought you were crazy. I had
41:21faith that you would be successful, but I’m like, dude, really? I I can’t believe you’re doing this. Um, but so
41:27freaking proud of you for what you’ve been able to to build and and do with this. And you’re right, you you were
41:34made for this, right? And so it was putting you in that position to really be successful. And now you’re going
41:40through some of those small business transitions again, but as an owner of an agency. Yeah. Yeah. Absolutely. I mean, it’s
41:47been so rewarding, Rich, for the last, you know, almost six years that we’ve been
41:53in business. Now, January would be six years. So, we made that five five year small business hurdle that most, you
41:58know, whatever the statistic is, most businesses don’t make it that long. We made it through that. Um, every year we’ve grown materially, right? The
42:04percentage of growth goes down as the revenue goes up, but every year we’ve grown materially. Uh, we run a very healthy company. And I think that
42:14what has kept me going and what I I believe will always keep me going is the
42:20ability to trial and error my own ideas. And that’s what I couldn’t do in the
42:26corporate world. So if I, you know, I’m a creative guy and if I think something might work that’s different from anybody else, I
42:34can at least deploy it without any red tape. And because of that, you know, it’s easy
42:40to say, hey, well, if I knew it was going to be this good, I should have did it years years before. But I I never say
42:46that because I don’t think I was ready. You know, I’m a man of faith and the man upstairs gave me the right opportunity
42:51at the right time. And it was July 1st, 2020 or whatever. That’s when I January
42:571st, kind of when we started, you know, jumping in. That’s when the time was right for me. And so I would encourage
43:04people that are looking to do this um definitely get your ducks in a row and
43:09uh you know, give yourself a hard deadline and just go through with it, right? It’s the same kind of thing with our coaching academy through the um
43:16through the roofing agency and my partner Deshawn and that. We decided, hey, we’ve been doing this for a few years. we want to do our live event and
43:23we’ve never done a live event and he’s always had fear will anybody come will anybody pay us for the you know
43:29opportunity to come see us and and he had that self-doubt even as a successful sales coach um and I didn’t know right I
43:35did some music management back in the day I’ve put on some church concerts but I’ve never done like big ticket sale
43:41events for myself and so we just committed we said hey you know what
43:46we’re going to put it on Facebook we’re going to make it official we’re going to pick the dates and we’re is going to
43:51figure it out along the way. And that was in February of this year, um the events in November. And we figured out a
43:57lot on that journey, but I think it came from the conviction behind the commitment, right? We were just like, “Hey, we’re doing it.” And once it’s out
44:03there, we’d look really silly to walk that back. So, we got to figure it out. Um and that’s cool. And we’ve sold 120
44:11uh 120 tickets, and we have a full room, and we have great speakers coming on top
44:16of our, you know, in-house team. And and it’s going to be a blessing. And I think again that was just another small
44:22midgame moment along the way. But when you’re thinking about how do I find
44:27success as an entrepreneur, the first thing is that you just have to believe in yourself. You have to be willing to
44:32hear no. You have to be willing to power through that. Um and it it can be a game
44:38changer. It’s not for everybody. It’s not for the faint of heart. But man, if uh if you jump in and the getting’s
44:44good, it’s real good. Bruce, that’s a really good place, I think, for us to uh to leave the journey conversation. As we
44:51look to to wrap up, I would love to find out from you. Obviously, you’ve got you’ve got amazing kids that are
44:57growing, getting older, hitting their middle school and high school years coming up. Um through your journey,
45:03you’ve learned a lot. Um, are there is there one like major principle that
45:09you’ve learned along the way that you hope to instill in in the kids as they get older and get ready to jump out on their own?
45:14Yeah, I I think for me it would be every opportunity, no matter what situation you’re in, is a learning opportunity.
45:20Um, you know, it’s not just about learning at school or learning in sports, but you got to take the silver
Life Lessons for the Next Generation
45:26linings out of a lot of crappy situations along the way. Um, and you know, look, we’re building a successful
45:33business that could be um, very lucrative for our kids right out of high school.
45:39That said, I think I kind of want them to go out in the workforce a little bit on their own and learn from some other
45:45people and not just learn from dad, right? Go get their teeth kicked in. Don’t have that immediate success of
45:51walking to a, you know, a six-f figureure job at 18 or 19 years old just because, you know, you have the ability
45:57to do that. But go struggle a little bit, right? Go drive a mediocre car and
46:05go make mistakes and go get in trouble by somebody else. These are all life
46:10lessons that I had to endure that made me the not only sales pro but leader that I am today. So without that
46:17experience, um I don’t know that I’d be doing them a service. So, I would just say that no matter your situation,
46:24whether it be good or bad, no matter if you’re working for yourself or you’re working for somebody else, corporate America, small business, try to learn
46:31from every day, every opportunity that you’re in, whether it’s good or bad, right? And make something positive out
46:38of it because those lessons may it may be hard to see the forest through the trees, but they’re all going to come to
46:44fruition and pay dividends one day for sure. That’s great, Bruce. Thank you so much for joining. If people want to follow
46:49you or find out more, how do they do that? Uh yeah, man. I mean, I’m on LinkedIn, all the socials. Uh best roof for
46:55marketing. You can check us out. Um we’d love the opportunity to talk to anybody about sales or marketing. I mean, I just
47:01it’s my passion, as you know. And uh yeah, just go follow us online. All right, good stuff. And we’ll have
47:07links to um those places and a few others in the show notes as well. So, Bruce, thank you again for joining. I
47:13had a great time. Thanks for joining us on the Midgame Mindset. If today’s episode sparked a new idea or helped shift your
47:19perspective, share it with someone who’s ready to grow. Subscribe, leave a review, and keep playing the game. With
47:25the right mindset, the best moves are still ahead. Until next time, keep changing the game.
