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Welcome to our newsletter #39! Let’s talk about something a lot of entrepreneurs don’t like to admit: The messy middle.
Years and years ago, when I first hit that million-dollar milestone with Grizzly Junk Pros, I thought I had it all figured out. It felt like we were on a straight path to the top. But reality hit—hard. I was working more hours than ever and somehow making less money. It’s that strange phase of growth where scaling actually starts to hurt. The profits shrink, the workload doubles, and you can’t do it all yourself anymore. But hiring help feels like watching money fly out the door.
Sound familiar?
The messy middle is tough. Whether it’s investing in new trucks, hiring extra hands, or building better systems, the expenses pile up, and it’s easy to feel like you’re moving backward. But here’s what I’ve learned: the messy middle is temporary—it’s part of the journey, and it lays the groundwork for something bigger. If your growth feels like it’s slowing down, that’s not failure. In fact, you’re right where you need to be.
Here’s the big mistake most business owners make during this time: they pull back. Instead of leaning in, they stop investing in the very things that could push them to the next level.
Ask yourself:
How much revenue are you leaving on the table by trying to do everything yourself?
How many missed opportunities are piling up because you’re too focused on the day-to-day grind?
What kind of growth could you unlock if you leaned into building a team and letting go of tasks that don’t make you money?
Investing in your business isn’t just about spending money—it’s about opening up new possibilities.
Cash Flow Crunch: When scaling Grizzly Junk Pros, cash flow strain hit hard. Suddenly, I was paying for more trucks, a bigger crew, insurance, marketing, and better software. I’d watch the money go out faster than it came in, and it shook my confidence. But I knew this was part of the process. You’re building the infrastructure that will support real growth.
Operational Bottlenecks: In the beginning, I handled everything—customer calls, dispatch, even jumping on a truck when needed. But as we scaled, it became impossible to manage it all. This is where systems come in. Whether it’s upgrading your software, documenting your processes, or building a better dispatch system, investing in these things is essential for long-term success.
Team Management: Hiring the right people is key. And I learned the hard way—it’s not just about filling a position; it’s about finding people who fit your vision. If you don’t train and set clear expectations, you’ll face more headaches than relief. Finding the right team members who understand your goals will make your business run smoother.
Mindset Shift: One of the biggest challenges is changing your mindset from being hands-on with every job to becoming a leader who delegates and trusts the team. Letting go feels risky, but it’s the only way to grow.
The Emotional Rollercoaster: Scaling isn’t just tough physically—it’s mentally draining. One day you’re on top of the world; the next, a key employee quits (my general manager actually did this to me a week before my wife gave birth to our first child), or a truck breaks down, and it feels like everything is at risk. But it’s in these moments that growth happens. The messy middle is where you lay the foundation for a business that can run without you making every decision.
Leaning In Instead of Pulling Back: If you’re in this phase right now, don’t pull back. Yes, it’s tempting to handle everything yourself or wait until you’re making more money before investing in better tools or people, but that’s a trap. You have to lean into the uncomfortable investments—whether it’s in new equipment, better systems, or building your team.
Ask yourself:
Are you losing money by handling tasks that aren’t driving revenue?
How much more could you make if you had systems that allowed you to focus on growth, not operations?
What could your business look like in six months if you invested now?
The messy middle is temporary, but it’s a crucial part of your business’s evolution. It’s the bridge from being an owner-operator to becoming the CEO of a business that runs smoothly without you. And that’s where real growth happens.
My Final Thoughts: Don’t shy away from the discomfort of scaling. Lean in, make the right investments, and trust the process. You’ll look back and realize this challenging phase was the stepping stone to lasting success. ✌️
Justin Hubbard
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