The First Step Most Business Owners Skip (And Pay For Later)

May 20, 2025

Kay here. This week I'm covering:

  1. My journey taking over a 35-year-old business and…a reality check

  2. The critical first step every owner needs before systems or growth

  3. Three quick reality checks that will transform your daily experience

  4. And more...

Best Links

Top revenue resource: How to 10x your B2B sales using the Mutual Intro Playbook by Jesse Pujji and team

Cost optimization insight: Jeff Sands on how to turnaround a company

Industry trend spotlight: Join me and other experts in NYC on June 4th for a full day of insightful deal team conversation. For anyone looking to level up their small business acquisition game.

The Old Way Wasn’t An Option

When I stepped into a 35-year-old business, I quickly realized I was in trouble. The previous owners had set up a lifestyle operation that worked for them but wasn't built to grow.

I found myself taking on far more than the previous owners because I wanted something different. I didn't want stagnation.

I wanted systems and scale.

Frankly, even maintaining the status quo seemed terrifying with the shifting real estate market and increasing competition. Standing still wasn't an option.

I was working harder than ever, but the business wasn't transforming at the pace I needed. Something had to change, and that something was me.

That's when I discovered the first crucial phase that most business owners skip: stabilizing. Before you can build systems or grow, you need to create a solid foundation.

The Owner Reality Check: Start Here

Most business owners skip the critical first step: stabilizing themselves and their business. They try to grow or build systems on a shaky foundation.

The foundation of business stability isn't your revenue or your tea…it's YOU. Your business mirrors your habits and blind spots.

Where are you the bottleneck? It's easier to blame market conditions or employees than to look in the mirror.

Three Quick Reality Checks to Transform Your Business

Reality Check #1: The Resentment Inventory

List everything you resent about your current role. These tasks should be delegated, eliminated, or transformed.

Reality Check #2: The Energy Audit

Track your energy levels hourly for three days. Match your most important work to your natural energy peaks.

Reality Check #3: The Bottleneck Assessment

Ask your team: "What decisions are waiting on me right now?" Create guidelines to help them move forward without you.

Don't skip this foundation.

How I Can Help

  1. Chief Rebel Peer Groups - Join a carefully curated group of non-competing business owners building together. Join the waitlist

  2. Exit Advisory - One-on-one guidance to maximize your business value, whether you plan to sell in 1 year or 10. Schedule a consultation

Until next week,

kay

Chief Rebel

P.S. Forward this to a business owner friend or client who might find it useful.

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