094: From Hot Dog Cart to Multi-Industry Mogul: Kevin Dooley’s Systems Every Startup Needs

What does selling hot dogs in college have to do with becoming a successful multi-industry entrepreneur? In this episode, Kevin Dooley shares the raw, real, and refreshing story of how listening to his customers, building simple systems, and aligning his inner mindset with business strategy helped him go from a scrappy side hustle to coaching founders and building multiple thriving companies.

Whether you’re in the early days of your business or ready to scale with soul, Kevin’s journey will inspire you to rethink how you work, create, and lead.

You’ll Learn:🛠️ Kevin’s Top Takeaways:

• How Kevin’s first entrepreneurial venture started with a hot dog cart on a college campus 🍴

• The mindset shift that the pandemic triggered—and how it changed his entire business philosophy

• Why understanding your customer deeply can make or break your startup

• The difference between “rise and grind” vs. “rise and create” and how it shapes sustainable success

• How to align your personal desires with your business goals (and why that matters more than ever)

• The 9 key systems Kevin teaches to simplify, scale, and sustain your business

• How to make feedback your most valuable business tool

• Why joy and satisfaction are legitimate business metrics

1. Start simple, but start—your first idea is your best teacher

2. Systems > hustle: repeatable processes create freedom

3. Customer feedback is your growth engine—don’t ignore it

Sustainable success begins when your mindset and skillset work together; Alignment isn’t a luxury—it’s a strategy

🔗 Links & Resources:

💡 Work with Kevin To Grab Kevin’s Free Startup Systems Knowledge → Kevin on Instagram, Kevin on LinkedIn

💌 Join the Flying Upstream masterclass → Here

Leave a ★★★★★ review on Apple Podcasts or Spotify! It helps us reach more soul-led entrepreneurs ready to build with purpose, not pressure.