What happens when you refuse to wait for the “perfect time” to chase your dream?
In this episode of Lead Like a Girl, host Jessica sits down with Caleb Cowden—the podcast’s very first male guest—to talk about the grit, strategy, and mindset it takes to grow a business while keeping a full-time corporate career. Caleb shares his own entrepreneurial journey, from launching ventures to advising business owners on how to prepare for their best possible exit.
The conversation dives into the power of intentionality, why risk is inevitable, and the unique challenges women face in entrepreneurship. You’ll hear practical tips on building a team you can trust, balancing your time between a side hustle and a day job, and tracking key metrics like EBITDA to ensure you’re steering your business toward success.
If you’ve ever wondered how to define success on your own terms—or how to turn preparedness into opportunity—this is your blueprint.
You’ll learn:
Why entrepreneurs can’t afford to wait for the “perfect” moment to start
How to balance corporate work with side hustle growth
The crucial role of building a strong, aligned team
Why women entrepreneurs face different challenges—and how to navigate them
The financial numbers every business owner should track
How risk and failure shape long-term success
Why your network defines your trajectory
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