In the early days, I tried to do everything myself. I built the products, sold them, delivered them, answered every email, and fixed every problem. My business could only grow as far as my hours could stretch, and my hours ran out fast.
That's the trap of the talented founder. You're good at the work, so you keep doing all of it. But a business that depends entirely on you isn't a business. It's a job you created for yourself.
You can't scale what you won't hand off.
How I made the leap
I had a front-row seat to someone who did it well. Every day I watched my mentor Eddie run his real estate business, his brokerage, and his moving company, and I saw him delegate constantly. He didn't do everything. He built people who could.
In 2018, before most people were doing it, I hired a team in the Philippines to help fulfill web projects and marketing work for my clients in the U.S. I didn't wait until I had it all figured out. I gave myself the approval to become a boss before I felt like one. For the first time, my business could grow beyond my own hours.
Signs you need help
- You're making money but drowning — That's a management problem, not a sales problem.
- You're the bottleneck — Work waits on you to move forward.
- Your needle-movers keep getting pushed — Busywork is eating the time for sales and strategy.
- You can't step away for a day — Without everything stalling.
What to hand off first
Look at your week and sort every task into two buckets: needle-movers that only you can do, and everything else. Start by handing off work that is repeatable, time-consuming, and easy to explain. Keep the work that requires your relationships, judgment, or vision for now.
Delegate the way my father led
My father led crews on tough job sites for decades, and people wanted to be on his team. His principles are still the best management guide I know:
- Lead by example — Your team watches what you do far more than what you say.
- Never ask others to do what you wouldn't do yourself — When you've done the work, people trust your direction.
- Give clear, direct instructions — Most delegation fails because the instructions were vague.
- Give them every tool and piece of information — You can't hold people accountable if they didn't have what they needed.
- Look out for your people — Ask, “Are you OK today?” and mean it.
- Show appreciation with small rewards — A box of doughnuts or breakfast burritos goes a long way.
Own the outcome
When someone on my team misses the mark, the first question I ask isn't “What's wrong with them?” It's “What did I miss?” Were my instructions clear? Did they have what they needed? Did I explain why it mattered? A leader owns everything in their world.
Write it down before you hand it off
- Write the outcome — What does done look like?
- Write the steps — How you do it today, in plain language. A screen recording helps.
- List the tools and access needed — Logins, templates, examples.
- Set a check-in — Review the first few together, then step back.
- Keep it simple — If they can't repeat the plan back to you, it's too complicated.
Start with one task
You don't need a big team to start managing. You need one task you're willing to hand off, and the discipline to hand it off well. Pick it this week, write clear instructions, and give someone everything they need to succeed.
Want help applying this to your business?
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