When I started Penebaker Enterprises in 2002 with $1.5M in revenue, I thought the hard part was getting the business off the ground. I was wrong. The hard part was every growth stage after that, because each one required me to become a different kind of leader.
I’ve gone from running a small roofing and sheet metal company to growing it to $15M, then scaling Roofed Right America to over $35M across four Upper Midwest markets with 180 employees, and now serving as Regional General Manager at Great Day Improvements. Each stage demanded a completely different mindset.
TL;DR: Only 30% of small businesses survive to year ten (Fundera, 2025), and the Project Management Institute found that companies using milestone-based planning achieve growth objectives 2.3 times more frequently. The mindset that gets you from zero to $1M won’t get you to $10M. Every growth stage demands that you let go of old skills and develop new ones. Here are six shifts that mattered most across my career.
When should you stop doing everything yourself?
Kabbage research shows that 92% of small business owners believe mentors have a direct effect on growth and survival (Kabbage, 2025). That stat tells you something: the people who scale aren’t lone wolves. At $1.5M, I was involved in everything. Estimating jobs. Managing crews. Handling customer complaints. Ordering materials. I wore every hat because that’s what startup founders do.
The first major mindset shift was accepting that I couldn’t do everything and shouldn’t try. Delegation isn’t about finding people to dump tasks on. It’s about building a team of people who can own outcomes, not just follow instructions.
When your name is on the building, every mistake feels personal. Letting someone else handle a customer relationship or manage a project felt like a risk. But the alternative was being the bottleneck in my own company. The cost of not delegating was higher than the cost of someone doing it differently than I would.
What’s the difference between revenue focus and systems focus?
According to Bluevine’s 2025 report, 58.4% of small businesses met or exceeded their revenue projections, but growth without systems is chaos (Bluevine, 2025). Early on, success meant closing deals and completing projects. Revenue was the scoreboard, and I watched it obsessively. But somewhere between $5M and $10M, I realized revenue without repeatable processes is just organized firefighting.
I had to shift from thinking about individual projects to thinking about systems. How do we estimate consistently? How do we onboard new hires so they’re productive in weeks instead of months? How do we track quality across multiple crews working simultaneously?
Systems thinking is what separates a $5M company from a $50M company. Revenue gets you started. Systems get you scaled. This was one of the biggest lessons I carried from Penebaker Enterprises into Roofed Right America and into my current role.
How do you lead when you can’t know everything?
Gallup’s 2025 data shows that managers account for 70% of the variance in team engagement, yet only 30% of managers are engaged themselves (Gallup, 2025). At a small company, the leader knows every detail. Every spec. Every customer name. Every truck’s status. That knowledge is power at small scale.
At $35M across four markets? Impossible. The mindset shift is accepting that you don’t need to know everything. You need to know everyone. Specifically, you need to know and trust the people who know everything in their respective areas.
I talked about this in my post on building high-performing teams across multiple markets. The leader’s job at scale is to build relationships, set direction, and remove obstacles. The details belong to the people closest to the work.
When does collaboration beat competition?
The National Federation of Independent Business reports that 47% of small business owners have difficulty filling positions with qualified applicants (NFIB, 2025). In that environment, competing for talent the old way doesn’t work. You need partnerships, industry relationships, and a reputation that attracts people.
As a startup founder, you compete with everyone. Other contractors. The market. Time. Capital. Competition sharpens you. But as you grow, collaboration becomes more useful. Vendor partnerships. Cross-functional teams. Even relationships with competitors can pay off when you’re operating at scale.
This shift also applies to how you lead internally. Small company leadership can be top-down and directive. Large company leadership has to be collaborative. You need buy-in, not just compliance. You need people who are invested in the outcome, not just afraid of the consequences.
How do you think long-term when short-term demands are constant?
Only 30% of small businesses survive to their tenth year, according to Fundera’s analysis of SBA data (Fundera, 2025). The ones that make it are the ones that can hold both short-term execution and long-term strategy in their heads simultaneously. When you’re running a $1.5M company, you think in weeks and months. Can we make payroll this Friday? Do we have enough jobs booked for next month?
That survival mindset is necessary at that stage. But it becomes a liability at scale. At $35M, I had to think in quarters and years. Where do we want to be in 18 months? Which markets should we enter next? What investments in technology and training will pay off three years from now?
Strategy without execution is daydreaming. Execution without strategy is just running on a treadmill. Nearly 30 years in this industry taught me that the leaders who struggle most are the ones who can’t hold both timeframes at once.
What happens when your identity has to change?
The Bank of America 2025 Business Owner Report found that 74% of small and mid-sized business owners expect revenue increases, and nearly 60% plan to expand (BofA, 2025). Growth is the goal. But nobody warns you about the identity crisis that comes with it. This was the hardest shift of all.
I came up in the trades. I could install a roof, fabricate sheet metal, and troubleshoot problems on a job site. That expertise was my identity for years. Becoming a leader meant letting go of that identity. My value was no longer in what I could do with my hands. It was in what I could build with my mind. Vision. Strategy. Culture. People development.
If you’re in the middle of this transition, the discomfort is normal. I wrote about the career pivots that happen within an industry and how each one requires letting go of something familiar.
The bottom line
Growth requires change. Not just in your business, but in yourself. The mindset that gets you from zero to $1M will not get you to $10M. The mindset that gets you to $10M will not get you to $50M. And the mindset that works as an entrepreneur doesn’t automatically work as a corporate executive.
Each stage demands that you get uncomfortable, learn new skills, and let go of old ones. That’s not a sign that something is wrong. It’s a sign that you’re growing.
If you’re navigating your own growth journey, I’d love to connect. Find me on LinkedIn or explore my Experience page for more of my story.
Frequently Asked Questions
What’s the hardest mindset shift when scaling a business?
Letting go of your identity as the expert. When you build a company on your technical skills, becoming a leader means your value shifts from what you can do yourself to what you can build through others. Kabbage research shows 92% of successful business owners credit mentors, which tells you growth is rarely a solo act.
When should a small business founder start building systems?
Between $5M and $10M, systems become non-negotiable. Before that point, you can muscle through with hustle and personal involvement. Past it, the lack of repeatable processes creates chaos that compounds with every new employee and project. Only 30% of businesses survive to year ten (Fundera), and the ones that make it almost always have strong operational systems.
Can an entrepreneur succeed inside a larger corporation?
Yes, but it requires a specific mindset adjustment. You go from complete autonomy to operating within a structure with stakeholders, corporate strategy, and processes you didn’t create. The combination of entrepreneurial thinking and organizational discipline is rare and worth developing. Think like an owner even when you’re an executive.
About Khary Penebaker
Khary Penebaker is a Regional General Manager at Great Day Improvements, overseeing operations across Chicago, Madison, Milwaukee, and Minneapolis. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership experience in construction, operations, and civic engagement.
Frequently Asked Questions
What leadership experience does Khary Penebaker bring to his keynotes?
Khary grew a construction company from $1.5M to $15M in revenue with 50 employees, then helped scale another company to $35M+ with 180 employees. His leadership lessons come from real operational experience.
What industries does Khary Penebaker speak to about leadership?
Khary speaks to audiences across industries including construction, manufacturing, corporate, nonprofit, and association events. His leadership principles apply universally.
How is Khary Penebaker's leadership keynote different from other speakers?
Khary combines hands-on business building experience with personal resilience. He does not teach theory. He shares what actually worked while scaling multimillion-dollar operations.
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Last updated: March 25, 2026