Executive debt is the hidden cost of short-term leadership decisions, and it shows up as strategy whiplash, broken workflows, and burned-out teams. In this episode of Servant Leader’s Library, Nicholas Paulukow sits down with Monty Fowler to unpack how it builds, how it spreads, and how leaders can fix it. If you’re scaling and things feel harder than they should, this conversation will help you spot what’s really going on.
Nicholas Paulukow
Welcome back to Servant Leader’s Library—the podcast where leadership isn’t just about the title on your business card; it’s about the impact you leave behind. I’m your host, Nicholas Paulukow, CEO of ONE 2 ONE Incorporated. Today we’re cracking open a chapter every founder, CRO, and revenue leader needs to read—whether they realize it or not.
My guest is Monty Fowler. If you think “executive debt” is just another buzzword, buckle up.
Monty doesn’t just talk about it—he makes it visible, measurable, and most importantly, solvable. With more than 33 years in technology sales, strategy, and revenue leadership across SaaS, enterprise software, FinTech, telecom, IoT, and more, Monty has seen what truly works—and what quietly breaks organizations from the inside out.
Today we’re diving into executive debt, revenue strategy, leadership accountability, and what it takes to scale without losing your soul.
So grab your notebook. Monty, welcome to the podcast.
We help leadership teams build more resilient IT foundations. Curious what that looks like?
From the Trenches to the Table: Monty’s Leadership Journey
Monty Fowler
Nick, I don’t know how I can follow that. Thanks for having me—I love your podcast.
I love the topic of servant leadership. It’s been central to my growth as a leader over the years.
I’m a managing partner at Aspire6. We started the company in 2024, and we’ve got about 20 people on staff. We consider ourselves an operator-friendly consultancy—meaning none of us are career consultants. We’re operators. We’ve been in the trenches doing the work for years.
I started my career in the early ’90s after active duty in the Army.
Nicholas Paulukow
Thank you for your service.
Monty Fowler
It was an absolute privilege.
After that, I got into network engineering. I didn’t know much at first. I learned on the job, got certifications, and spent my first five years as a Director of IT in architecture and engineering firms. Then I moved to the vendor side as a solution engineer—back when we called them system engineers.
And that’s where a pivotal moment happened.
The Car Ride That Changed Everything
Monty Fowler
We were driving from Chicago to Bloomington, Illinois, to see State Farm. We were about to close what would’ve been the largest deal in our company’s history.
I’d been the solution engineer, driving back and forth three or four days a week—four-and-a-half hours round trip—just to get it done.
This was back when you showed up, signed contracts in person, took pictures, shook hands—the whole thing.
I’m sitting in the back seat listening to two reps talk about how they’re going to spend their massive six-figure commission checks.
Nicholas Paulukow
Uh-oh.
Monty Fowler
They were spending it before the deal even closed. One was going to Europe, the other was remodeling the house.
Meanwhile, I knew I was going to get a $10,000 bonus. I was promised President’s Club as an SE—Maui—if we closed it.
I stayed quiet. My VP of Sales, a Texas guy named Steve Connor, turns around and says, “Monty, you’re kind of quiet today.”
I said, “I’m sick of hearing these guys talk about spending all their money.”
He paused and said, “Well hey buddy, if you don’t like the way you’re getting paid, why don’t you take your skirt off and go into sales?”
That was the kind of comment you could say back then without HR calling you five minutes later.
It shut me down. We closed the deal. A couple weeks later I called him and said, “That thing you said in the car… were you serious?”
He said, “I can’t believe it took you two weeks to call me.”
That’s how I went into sales.
Truth With Love: The Mentorship That Refined a Leader
Monty Fowler
Steve took me under his wing. Great servant leader. Great mentor.
One day he sat me down and said, “You’re the smartest guy I’ve ever met. Any room we walk into, you’re the smartest guy in the room. The problem is… you feel the need to let everybody know you’re the smartest guy in the room. That one thing will keep you sidelined for decades.”
That was brutal truth—truth with love.
I remember thinking: when Steve walks into a room, everybody wants to know what he’s about to say, what the plan is, and they get on board instantly.
I wanted to be that.
The Humility of Needing Guidance
Nicholas Paulukow
I learned that the hard way. I thought I could do everything on my own. Then I got hit hard with the realization: have a mentor. They’ve been there, done that. It’s humbling.
Monty Fowler
Steve taught me the value of mentorship and paying it forward.
Now I’m on the back nine of my career, and I try to spend as much time as I can coaching and mentoring—free or paid. If someone needs help, I want to be available.
Startups, Synergy, and the “Idea Guy vs. Implementer” Dynamic
Nicholas Paulukow
You’ve done eight startups. Have you and Steve followed that journey together?
Monty Fowler
We did six of them together. Sometimes he brought me in, sometimes I brought him in. Later in your career the dynamic shifts—sometimes the student becomes the master in some areas.
Nicholas Paulukow
What early lessons shaped you?
Monty Fowler
We had an interesting dynamic: the idea guy and the doer.
Nicholas Paulukow
The implementer.
Monty Fowler
Exactly. Steve is the big idea guy. I’m the one that turns it into reality.
I don’t need to be the guy on stage. I’m happiest making sure the trains run on time—building, figuring out what’s next. That’s why strategy became the centerpiece of my career over the last seven years.
When Growth Forces a New Leadership Gear
Nicholas Paulukow
You can get so far as an individual, but when you hit a certain dollar amount, you need that role to successfully navigate it.
Do you see that frequently? Where do people realize they have revenue and sales problems? Is it a stage? A revenue number?
Monty Fowler
It’s every stage. Let’s keep it confined to tech—especially VC-funded tech.
When you look at the lifecycle of a VC-funded company, there are unique challenges that can kill a company at every stage.
Pre-seed—you might find what you’re trying to build isn’t possible, or the market doesn’t want it. Seed—you get real customers and realize the product isn’t good enough yet. Series A—the game is real. You’re on a shot clock.
Unless you’ve been down the trail before, you don’t know what’s around the bend.
As I’ve gotten older, I walk into startups where teams are younger, and I can pattern-match quickly. I can sit in one meeting and tell you who has toxic mindsets, who’s driving decisions, and who the real decider is—regardless of title.
The business health check is easy now. The dashboards are easy. But the interpersonal relationships and cultural dynamics are what make companies fail or succeed.
Culture is the one thing your competitors can’t steal or replicate.
The “Founding AE” Unicorn Problem
Monty Fowler
I see a lot of seed-stage and Series A companies hiring a “founding account executive.”
You know what that means: you’re going to do the work of a VP of Sales—build the whole go-to-market program—and carry a quota.
Nicholas Paulukow
And you better hit your number because the whole company is selling.
Monty Fowler
Exactly. Sometimes it works—I’ve been that person. But it’s risky. Unless you’ve been down the trail before, everything you hit is the first time you’re seeing it.
We have better tools today—ChatGPT, Claude—that help us “fake it till we make it.” But it’s not just knowing what to do. It’s doing it consistently, with rigor and intentionality.
VC vs. Private Equity: A Quick Primer
Nicholas Paulukow
For our audience—when you say VC, explain that versus privately held or bootstrapped.
Monty Fowler
You’ve got three ways to fund a company:
Self-funded—bootstrapped. Other people’s money—from friends and family to Kickstarter to venture capital. And private equity.
Venture capital is institutional money. A group pools funds into a firm, and that firm invests in companies for equity—often a big chunk. Funding comes in rounds: Series A, B, C. Every round adds expectations. Miss them, and bad things happen—funding dries up, executives get fired.
Private equity is different. They usually invest in stable companies that are profitable and growing. VC is more like roulette—making bets and hoping the winners cover the losers. PE is more like banking—they buy stable companies and roll up competitors.
The Four Tiers of Performance (And the Mistake Leaders Keep Making)
Monty Fowler
When you look at your people, you’ve got tiers.
First, you’ve got your doers—the reliable people. You give them a task and it gets done, high quality, without chasing.
Then you’ve got the worker bees. And I mean that lovingly—I love honey. Worker bees show up and do the job expected, but they shut it off after work. They turn it back on the next morning.
Then you have what I call the developers—people worth investing in. There’s something holding them back that you can identify. They need coaching, mentoring, opportunities.
Not everyone wants to grow, and that’s fine. I have a son who loves his stable hands-on job. His aspirations aren’t tied to paychecks—he cares about life outside work.
Then you’ve got the bottom tier—people who can’t perform in the role you hired them to do.
And here’s where we get it wrong: we burn most of our calories on the underperformers. We don’t spend enough time feeding the middle band.
There are people in that middle band who could become top performers—they just haven’t had motivation, coaching, a mentor, or a path.
I ask companies all the time, “What’s your career progression path?” And they look at me like, “What?”
They’ll say, “When we see someone who’s good, we promote them.”
That’s not a path.
Running a business is hard. Entrepreneurs are a unique personality type. But what we should be doing is intentionally developing future leaders—A players—player-coaches.
Instead, we’re always running around with a fire extinguisher.
Nicholas Paulukow
And we lose those people—not intentionally, but because they’re ignored.
The Personality Mix Every Leadership Team Needs
Monty Fowler
In a Series A company, you might have five to seven senior leaders. You need the right personalities at the table.
You need a visionary—often the founder—who sets the mission and communicates it clearly.
Nicholas Paulukow
And the time to do it.
Monty Fowler
Exactly. But visionaries get pulled into doing the “do,” and that’s not their gift. They’re thinkers, not doers.
You also need the naysayer—the “what if” person. HR systems often bias against them, but they’re essential. They’re the person who thinks through what could go wrong before you commit.
I am that person. Big Italian family—it’s in my DNA. It drives my wife crazy, but vacations run like clockwork because I have contingency plans.
You also need the peacemaker—the person who can diffuse tension. I’ve been in startup meetings where people scream, slam tables, even throw things. It comes from wanting to get it right, but you need someone who can slow it down, capture ideas, and find common ground.
Nicholas Paulukow
Would you consider them the cheerleader?
Monty Fowler
Not really. The visionary tends to be the cheerleader, or HR.
Nicholas Paulukow
I know a business leader who told me the biggest role in the company is the cheerleader—the one who keeps selling the message internally after the rally cry.
Defining Executive Debt: The Superset of What Breaks Companies
Nicholas Paulukow
Let’s dive into executive debt. What is it?
Monty Fowler
Executive debt is the long-term cost of short-term decisions.
If you work in tech, you already understand technical debt. Technical debt is the price you pay for early shortcuts—workarounds, compromises, things you’ll regret later when you need to scale.
Executive debt is the same thing—only bigger. Technical debt is just one feature of executive debt.
Executive debt comes from leaders who have great ideas and great strategic plans but can’t communicate that strategy to the people who have to execute it.
Another driver is leadership short-term memory. Q1 strategy. Q2 new strategy. Q4 new strategy. You whiplash the team.
Leaders forget that the “cool stuff” on the whiteboard has to be operationalized into workflows, processes, teams, systems, tools, and data flows.
If you don’t align people to goals, they interpret it differently. Misalignment becomes failure.
The book talks about four types of executive debt:
Strategic debt—big one-way door decisions that undermine the long-term plan.
Operational debt—workflows and systems that calcify and keep running long after they should.
Culture debt—people stop understanding why they’re doing what they’re doing; the script keeps changing; morale erodes.
Talent debt—A players disengage and leave, and even before they leave, they stop mentoring, stop coaching, and start preparing for the next job.
Stack those together and you’re in a bad place.
How Private Equity “Closes the Checkbook” on Toxic Leadership
Nicholas Paulukow
In private equity, they want returns quickly. How often do you see leaders cycle out because they can’t grow to the next level?
Monty Fowler
Yes, it happens. One thing private equity does better than VC is they pay close attention to who should be on the bus when ownership changes.
They interview leadership and frontline teams to identify toxic leaders—and they’ll clean house before or right after the investment.
Here’s an example.
I audited a manufacturing company in Lenexa, Kansas for a private equity firm. The company was stable and competitive. But every single interview started with the same message: “You have to get rid of the plant manager.”
What I heard was severe—harassment, berating employees, horrible language, especially toward women.
I sat with the PE partners and started with, “Close your checkbook.”
They were shocked. I explained: “Don’t invest another dollar until he’s gone.”
That afternoon, he was fired.
People called me afterward—some weeping—because they knew it, and they’d been trapped under it.
The Three Traits of a Great Leader
Nicholas Paulukow
What are the top three things that make a great leader?
Monty Fowler
Easy.
First, know your why. If you’re leading for ego or a paycheck, you’re in the wrong DNA. Your why needs to be bigger than you—maybe it’s taking care of your family, but it’s purpose beyond self.
Second, emotional intelligence. You can’t be a jerk in business today. Two generations will not tolerate bad behavior. They’ll leave, and they’ll tell everyone why they left.
Third, integrity—being the same person everywhere. Same at work, at home, at church, with friends, and alone. Authentic. Honest. Reliable. And when you fail, big enough to own it and make it right.
Those leaders are rare. When you find them, you hold onto them.
And over time, you build a circle of trust—people who take your call, open doors, and create opportunities together. That’s why I preach servant leadership. It’s an inverted pyramid: serve everyone.
Stuck as a Founder? You Don’t Need a New Tactic—You Need New Eyes
Nicholas Paulukow
Founders feel stuck. What advice do you have?
Monty Fowler
You need a different perspective—another set of eyes and a brain to examine what you’re doing, the results you’re getting, and your plan forward.
Ideally it’s someone who knows your industry and market—and can analyze how you’re thinking.
Because many times founders can’t even remember why they chose their strategy.
And here’s the bigger issue: 80% to 90% of strategic decisions are already made before the meeting. The CEO walks in with a fully baked plan, and the team only discusses how to execute it—not whether it’s the right plan, what data informed it, or how previous decisions like it performed.
Companies repeat strategic planning every year, but most don’t go back and analyze:
What inputs did we use last time? What outcomes did we get? Why? What changed? What should we carry forward?
Frameworks like EOS can help—if you actually do them with rigor and accountability.
If you don’t, meetings become a weekly reminder of what isn’t getting solved.
The IKEA Test: Frameworks Only Work If You Follow the Instructions
Nicholas Paulukow
Follow the instructions.
Monty Fowler
Exactly. You have to follow the instructions. If you skip a step, you don’t end up with a bed frame. You end up with an art project.
The Book and the Course: From Awareness to a 90-Day Fix Plan
Nicholas Paulukow
Tell us more about your course. Where can people get the book and course?
Monty Fowler
The book has been out a little over a year. People tell me, “You nailed it. I’ve got examples of everything you wrote.”
The book helps you identify executive debt and quantify it. But it doesn’t go deep on how to fix it.
That’s what the course does.
When you complete the course, you end up with a 90-day executive debt mitigation plan to execute with your team for one area of executive debt.
You learn how to: detect it, quantify the cost, prioritize it, and build a fix plan. Then you move to the next item on the list.
The course is self-guided, hosted on Teachable. You can access it through executivedebt.com or aspire6.com.
The real work is in the workbook—about 60 pages—where you do the same analysis we’d do if we came into your organization. By the end you’ve built a rhythm for asking:
Is this executive debt? What category? What’s it costing us? Who’s involved in fixing it? How do we communicate the fix?
Once awareness rises, behavior changes. People feel that “Oh—this explains why we’re stuck.”
Lead Better, Not Harder
Nicholas Paulukow
Well, there you have it—Executive Debt Exposed.
Monty, thank you for reminding us that real revenue growth isn’t about squeezing harder. It’s about leading better—healthy teams, clear strategy, and integrity that still wins even when the numbers are watching.
And to listeners: if this made you uncomfortable, good. Growth usually starts there.
Take what you heard today. Look honestly at your leadership team and ask:
What debt am I carrying that the team is quietly paying for?
Monty, as a servant leader, revenue architect, and the guy brave enough to call executive debt what it is—thank you for being part of Servant Leader’s Library.
As always: lead well, serve first, and we’ll see you in the next chapter.
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