From selling candy on the playground to building and selling multiple seven-figure companies episode artwork

EPISODE · Dec 26, 2025 · 43 MIN

From selling candy on the playground to building and selling multiple seven-figure companies

from Do Small Business Like a Big Boss Podcast · host Aisha Massengill

Episode Title:From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure CompaniesPodcast:Do Small Business Like a Big Boss🎧 Episode DescriptionIn this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Cheryl Perez, a seasoned entrepreneur and business coach, to talk about what it truly takes to scale a business from scratch.Cheryl shares her journey from corporate employee to building and selling multiple seven-figure companies, breaking down the mindset shifts, systems, and resilience required to grow sustainably. This conversation covers the real-life lessons behind building a business from the ground up—what worked, what didn’t, and what every aspiring entrepreneur needs to hear.🎧 What You’ll Learn in This Episode:The difference between working IN your business versus ON your business—and why both are required to scaleHow to know when it’s time to hire your first team member (even when the numbers feel scary)Why lead generation systems are the most overlooked investment for new entrepreneursHow Cheryl uses a six-step meditation practice to make million-dollar decisions without burnout⏱️ Episode Timestamps:Guest introduction: Cheryl Perez06:35 – Knowing when you’re truly “done” with playing small27:59 – Why capacity limits revenue38:57 – Stepping into Big Boss energy👤 About the Guest:Cheryl Perez is a seasoned entrepreneur and business coach who has built and sold multiple seven-figure companies. Through her coaching and educational services, she helps entrepreneurs transition from corporate careers, build scalable systems, and create freedom-driven businesses rooted in clarity, preparation, and resilience.🚀 Ready to Make Your Business Official?Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.👉 Register here: https://www.igotnext.co/training👉 Grab your FREE Legal Guide at:https://www.topemployermistakes.com🔗 Stay Connected with Sedgwick AndrewsFollow us across all platforms for legal tips, business strategy, and boss-level motivation:👉 https://linktr.ee/Sedgwick_Andrews_LC🎙️ Podcast MantraBuild the dream messy, build it scared, just don’t build it small.If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

Episode Title:From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure CompaniesPodcast:Do Small Business Like a Big Boss🎧 Episode DescriptionIn this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Cheryl Perez, a seasoned entrepreneur and business coach, to talk about what it truly takes to scale a business from scratch.Cheryl shares her journey from corporate employee to building and selling multiple seven-figure companies, breaking down the mindset shifts, systems, and resilience required to grow sustainably. This conversation covers the real-life lessons behind building a business from the ground up—what worked, what didn’t, and what every aspiring entrepreneur needs to hear.🎧 What You’ll Learn in This Episode:The difference between working IN your business versus ON your business—and why both are required to scaleHow to know when it’s time to hire your first team member (even when the numbers feel scary)Why lead generation systems are the most overlooked investment for new entrepreneursHow Cheryl uses a six-step meditation practice to make million-dollar decisions without burnout⏱️ Episode Timestamps:Guest introduction: Cheryl Perez06:35 – Knowing when you’re truly “done” with playing small27:59 – Why capacity limits revenue38:57 – Stepping into Big Boss energy👤 About the Guest:Cheryl Perez is a seasoned entrepreneur and business coach who has built and sold multiple seven-figure companies. Through her coaching and educational services, she helps entrepreneurs transition from corporate careers, build scalable systems, and create freedom-driven businesses rooted in clarity, preparation, and resilience.🚀 Ready to Make Your Business Official?Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.👉 Register here: https://www.igotnext.co/training👉 Grab your FREE Legal Guide at:https://www.topemployermistakes.com🔗 Stay Connected with Sedgwick AndrewsFollow us across all platforms for legal tips, business strategy, and boss-level motivation:👉 https://linktr.ee/Sedgwick_Andrews_LC🎙️ Podcast MantraBuild the dream messy, build it scared, just don’t build it small.If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

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From selling candy on the playground to building and selling multiple seven-figure companies

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This episode was published on December 26, 2025.

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Episode Title:From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure CompaniesPodcast:Do Small Business Like a Big Boss🎧 Episode DescriptionIn this episode of Do Small Business Like a Big Boss, host Aisha Jorge...

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