09/12/25 - Wakie Wakie 4:44

Welcome to Your 444 Newsletter!

Where resilience, reality, and real solutions collide.

Today’s topic?

One of the scariest parts of being a business owner.

The chance of losing everything you worked for.

When your family depends on YOU, and the buck stops with you, there’s no hiding.
And when the pressure hits, it usually shows up in ways you never expected.

I’ve seen it crush people.
Smart people.
Talented people.
People who thought they had it all figured out.

But here’s the truth.
Entrepreneurship is not a game for the weak.
And it is not about how smart you are.
It is about who you have around you when things get hard.

Because nobody sees clearly when they are stressed, broke, and freaking out.

4 Thoughts to Reflect On

  1. Every business owner will face chaos.
    It is not a matter of if. It is a matter of when.

  2. Smart is not enough.
    Talent and education mean nothing if you have no one to lean on when things break.

  3. Pressure blinds you.
    In the middle of crisis, the solution is often invisible until someone else points it out.

  4. Access is survival.
    The right phone call, at the right time, can keep your business alive.

4 Lessons I’ve Learned

  1. I have lost money faster by being isolated than by making bad moves.
    The cost of going alone is always higher than asking for help.

  2. Your circle dictates your ceiling.
    If no one around you has solved the problem before, you are stuck guessing.

  3. Stress makes small problems look massive.
    But a solution is simple when you are surrounded by people who have already fixed it.

  4. Community is not optional.
    The bigger your business gets, the more you need direct access to people who can shorten your timeline to a fix.

4 Challenges for You This Week

  1. Audit your stress points.
    Circle the tasks that drain you and ask: could someone else do this better or faster?

  2. Call out your blind spots.
    Write down one area where you keep hitting the same wall. Naming it makes it easier to fix.

  3. Reach out for insight.
    Find one business owner who’s solved your problem before. Ask a direct question and listen.

  4. Get in a stronger room.
    If your current circle can’t help in a crisis, it’s time to upgrade who you spend time with.

"Surround yourself with only people who are going to lift you higher.”
— Oprah Winfrey

You do not win this game by going alone.

You win by being in the right room, with the right people, solving the right problems.