Episode 307 | The Profit Answer Man I Featuring Kurt Wilkin
You built the company with someone… and then you outgrow them.
In this episode of The Profit Answer Man, I sit down with entrepreneur and author Kurt Wilkin to tackle one of the most common (and emotionally loaded) growth challenges in business
Kurt—whose most recent company was HireBetter, a recruiting firm that partnered heavily with EOS companies—shares the core idea behind his book “Who’s Your Mic?” (often discussed as “Who’s your Mike?” in the conversation): every growing entrepreneur will eventually face a key early team member who was perfect then, but is overwhelmed now.
The “Mike” Problem: Your Business Partnered With Loyalty… Then Hit a Wall
Kurt explains the archetype clearly:
“Mike” is the person who was there at the beginning—the do-it-all operator: accounting, ops, and often the “integrator” role in the EOS sense. But growth expands the job faster than the person can grow. Mike can go from bookkeeper → accountant → controller → CFO… until one day you’re negotiating lines of credit or M&A conversations and realize Mike is “swirling” and in over his head.
And that’s where the real tension kicks in: Mike is loyal, hardworking, and often emotionally “foundational” to the founder’s story—so the founder waits far too long to act.
Why Founders Delay the Hard Conversation
Rocky shares how often he sees this with clients: owners go right up to the edge, have emotional calls… and still don’t “rip the band-aid off.”
Kurt’s take: most entrepreneurs are people-oriented, not always strong managers, and they struggle with uncomfortable conversations—especially when the person has been around for years. Kurt compares it to firing your best friend from childhood. That’s how it feels.
Do You Have to Fire Mike? Not Always
One of the most important nuances Kurt shares: the answer isn’t always termination.
Sometimes Mike can move into an individual contributor role. Sometimes the right move is reassignment. It depends on their ego, demeanor, willingness to be part of the team without being “the” leader, and whether they actually know they’re drowning. Kurt notes that if someone is truly overwhelmed, they may be relieved when the truth is finally acknowledged.
But Kurt also points out a key downstream issue if Mike stays in leadership while underqualified: you can’t attract A-players to work under a C-player leader.
Hiring in a World of Polished Resumes (and “Pipeline Paul”)
The conversation shifts into recruiting realities—especially today when candidates can present themselves perfectly on paper.
Kurt emphasizes that you still need the “people” side of hiring: asking strong questions, getting real stories, and having candidates prove what they’ve done—rather than relying on shortcuts.
Then he introduces one of his most popular book characters: “Pipeline Paul”—the salesperson who sells the dream during the interview, promises everything, and then fails to produce. One red flag Kurt highlights: repeated 18-month stints on a resume.
And even with good processes, sales hiring stays hard—because if they’re a good salesperson, they can sell you… without necessarily being able to sell your offering. Kurt’s practical advice: look for someone who has sold something similar (industry, product type, or service type).
The Small Business Sales Trap: “The Owner Can Sell… So the New Hire Should Too”
Rocky describes a classic scenario: a business owner is exhausted from doing sales and hires a salesperson hoping it will solve everything—only to realize they never built a real sales system to hand off.
Kurt agrees and adds that founders sell well because they are the face and they know everything. A salesperson can’t replicate that without structure. Kurt shares that for smaller businesses, he has seen better success by promoting someone who already knows the customers and “joining at the hip” for a period to transition the sales role.
“Next Level Natalie” and the Integrator Question: How Do You Afford Them?
Rocky asks the question every owner asks: integrators (and true A-player operators) are expensive—so how do you afford them?
Kurt’s answer: how can you afford not to? He argues most entrepreneurs have wasted money hiding in plain sight (“money in the couch cushions”)—from unused software subscriptions to excess headcount and inefficiency—and a strong integrator can remove waste and pay for themselves.
Rocky adds a powerful pattern he’s seen: if everyone is “super busy,” often there’s an underlying dysfunction—sometimes even one person who’s effectively creating fires that the whole team stays busy putting out. Remove the firestarter, and the business can run with fewer people and less stress.
Kurt reinforces the idea with a quote he loves: “Instead of putting out fires, fire the arsonists.”
Community Matters: EOS, YPO, and Not Being a “Special Snowflake”
Kurt shares why EOS is helpful for entrepreneurs: it’s a system that creates structure (and most of us need structure).
He also explains what he values about YPO: beyond business growth, it includes a family element—supporting the idea that strong leadership requires a well-rounded life. Source
And one of the most grounding moments: Kurt calls out a mindset he hears all the time—“you don’t understand, I’m a special snowflake.” His perspective: 95% of business challenges are common, and owners find better answers when they admit what’s happening and learn from peers.
How has the changed?
Where can people find you? podcast – unlocking moves
Guest Bio
As an entrepreneur, Kurt has experience growing, scaling, and exiting high-growth companies and now devotes his time to helping business leaders unlock their own success. Through his roles as the Co-Founder at HireBetter and Managing Partner at Bee Cave Capital, he’s had the opportunity to work with hundreds of entrepreneurs and CEOs—challenging and inspiring them to take their companies to the proverbial “next-level.”
Prior to founding HireBetter, Kurt founded and led The Controller Group (TCG), a professional services firm focused on accounting, technology and recruiting, which was acquired by Tatum in 2006. Post-acquisition, Kurt led the doubling of the firm’s revenues over a three-year period.
Kurt began his career with Ernst & Young, where he worked with early stage and high-growth middle market clients, and later served as Controller and Vice President of Finance for eFANshop, a Dallas-based internet retailer.
Kurt is an alumnus of the University of Arkansas, a Certified Public Accountant and an active member and officer of Young Presidents’ Organization (YPO). Kurt is passionate about entrepreneurship, is an active angel investor and sits on the boards of several companies and nonprofits. He lives in Austin with his wife and three sons and can usually be found coaching youth sports around town.
Links
Instagram: @Kurt.Wilkin and @UnlockingMoves
Facebook: @KurtWilkin
Twitter: @KurtWilkin
LinkedIn: Kurt-Wilkin
Ready to spot (and solve) your “Mike” problem?
If you’re scaling and your org chart hasn’t evolved with your reality—this episode will hit home. Kurt’s message is simple: growth makes the “Mike” problem inevitable. The win is recognizing it early and making a smart move before it becomes a painful one.
Listen to the full episode
Ep 307 Outgrowing Your Team: The Loyal “Mike” Problem Every Business Owner Faces with Kurt Wilkin: https://profitcomesfirst.com/ep-307-outgrowing-your-team-the-loyal-mike-problem-every-business-owner-faces-with-kurt-wilkin/
Watch the full episode on YouTube: https://www.youtube.com/@profitanswerman
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Music provided by Junan from Junan Podcast
Any financial advice is for educational purposes only and you should consult with an expert for your specific needs.