How Do I Stop Doing Everything in...

How Do I Stop Doing Everything in My Business? | Guest: Jake Thompson

UNDERESTIMATED: The Small Business Advantage Podcast by Shawna Suckow

S1 · E35

Oct 11, 2026

25:32

Episode notes

You started a business for more freedom. Somehow, you became the person who answers every email, fixes every problem, and can’t take a vacation without checking in. Congratulations on your promotion to Chief Everything Officer.

My guest Jake Thompson, founder of Compete Every Day, knows that trap. We talk about why being busy can feel like progress when it’s actually keeping you stuck, how doing everything yourself limits your business, and what it takes to hand off work without grabbing it right back. Jake shares a simple way to start documenting tasks before you hire help, plus the expensive lesson he learned trying to make his small business look bigger.

Jake built his 7-figure business, Compete Every Day, by selling T-shirts from the trunk of his car. Along the way, comparing his business with better-funded brands led him into debt, and doing too much himself kept him focused on work that someone else could handle. His lessons are useful for any small business owner who has a packed calendar but keeps wondering why the important stuff never gets done.

We get into the five types of drift Jake sees in leaders, especially “busy drift,” that sneaky feeling that answering emails all morning counts as moving your business forward. We also talk about why take-home matters more than impressive revenue numbers, how to move from doing everything to coaching the people who help you, and why a task done differently isn’t automatically a task done wrong.

One of my favorite suggestions is wonderfully manageable: the next time you do something you’d like to hand off, record yourself doing it. You’ve just started building instructions instead of waiting until you’re overwhelmed to explain everything from scratch. We also compare notes on the tasks we still struggle to let go of, including my graphic design and Jake’s travel booking.

Episode page with resources & transcript: https://www.thebuyerinsider.com/podcast/episode-35

CONNECT WITH JAKE

Compete Every Day: https://www.competeeveryday.com/

LinkedIn: https://www.linkedin.com/in/jakethompsonspeaks/

CONNECT WITH SHAWNA

Website: https://www.thebuyerinsider.com

Non-Snoozeletter: https://www.thebuyerinsider.com/newsletter

Free Small Business Marketing Resources: https://www.thebuyerinsider.com/vault

Subscribe: https://www.youtube.com/@ShawnaSuckow

TIMESTAMPS

00:00 Always Busy but Missing Your Priorities

01:50 Building Compete Every Day from a Car Trunk