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028 CEO or Bust: The Rough Road to Becoming Your Own Boss

with

Dawn Andrews

Show notes

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Show notes

Picture this: a bustling city, a woman in her prime, striving, hustling, like an ant carrying a load thrice its size. That was me. My world revolved around corporate towers, meetings, and unending to-do lists. It was as thrilling as it was exhausting.

But little did I know destiny had an unexpected twist for me that would change my path forever.

 If you’ve ever caught yourself daydreaming about starting your own business and calling the shots without a soul to answer to, except maybe your cat, then buckle up because we’re about to take a detour from Dreamville and land smack dab in the middle of reality city where you trade your business fantasies for a CEO nameplate. 

In this episode, I share:

  • The unvarnished truth about the roller coaster ride of entrepreneurship, coupled with practical strategies to overcome it.
  • The importance of mentors to steer your entrepreneurial ship in the right direction.
  • The art of business strategy and finance, and how it can catapult your business towards success.
  • The benefit/results of persistent learning to unlock your entrepreneurial capacity.
  • The significance of personal growth and adaptability and how these traits can forge a path to a thriving entrepreneurial life.

This episode at a glance:

[03:48]  I’ve always been a city girl. I love working in very urban environments with lots of, with a high population. But I was getting to a point where I just didn’t want to struggle like that anymore. I wanted the flexibility to be with my future kids.

[06:08]  I jumped into entrepreneurship like a cat on a hot tin roof. I was scrambling, struggling, and occasionally face-planting. Picture me like what claws out, like sliding down the roof, trying to hang on. 

[09:11]  Looking back, having a solid coach or mentor would have made all the difference. We may still have been in the same debt. It may still have taken the same time to pay it off. But where I put the money to grow and to support myself would have been better utilized. 

[14:31] We’ve all grown, learned, and risen together in our businesses. And it’s in these moments that you realize that you’re not just a chick with a dream. You are a Phoenix rising from the ashes of corporate life.

[15:27]  Not everyone is built to weather the storm of entrepreneurship. It is a rollercoaster ride where you are both the rider and the operator. But if you’ve got this gnawing feeling in your gut, that little voice whispering, you could do this. Then you’ve got to listen.

Resources and Links mentioned in this episode:

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More about the “She’s that founder” podcast

Welcome to She’s That Founder, the podcast for ambitious women who are ready to stop drowning in decisions and start running their businesses like the confident CEOs they were born to be with the help of AI magic.

I’m your host, Dawn Andrews—executive coach, business strategist, and founder of Free Range Thinking. I’m also a proud female leader, mom, and mentor who believes scaling a business shouldn’t come at the cost of your sanity.

Each week, we dig into the real tools and strategies you need to scale smarter, not harder: faster delegationsystems that won’t collapse if you take a nap, and AI tools that actually lighten your load instead of adding to it.

You’ll hear proven revenue strategies, executive leadership frameworks, and practical tools to build a business that grows without burning you out.

We keep it real here—expect candid conversations, quick hits, and the occasional founder rant. Listener discretion is advised (because we don’t always bleep the swear words).

If you like what you hear, make sure to follow along so you never miss an episode. And before you go, leave us a review—it means the world and helps more women founders step fully into their CEO power.

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