๐ŸŽ™ The Freedom Lifestyle Podcast ๐ŸŽ™

Episode 137: Freedom business reality: from agency life to freedom freelancing with Jake Madoff

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What you’ll learn from Jake:

โžก๏ธ How to find true work freedom

โžก๏ธ How to develop as a freelancer

โžก๏ธ How to accelerate personal growth in entrepreneurship

โžก๏ธ How to multiply your income

Learn everything about creating more freedom and live your dream life

Start a side hustle or build a freedom business โ€“ creating multiple revenue streams is the way to your freedom life. We show you how others do it successful too.

Get freedom business growth tips in your inbox ๐Ÿ’Œ
Join 4000+ digital nomads and freedom seekers!

Meet freedom business owner Jake

Jake Madoff is a full stack growth marketer specializing in paid media, SEO, and funnel optimization. What began as self-teaching web design for his own e-commerce business in 2014 evolved through co-founding a trade and barter app startup, to spending five years scaling a company’s ad spend from $300K to $2 million monthly.

During COVID, Jake transitioned to full-time freelancing, where he now helps businesses across diverse industriesโ€”from e-commerce to legal to B2B SaaSโ€”grow through strategic digital marketing.

Based in Manhattan, he represents a new generation of marketing professionals who’ve learned their craft not through traditional education but through hands-on experimentation, adaptation, and saying “yes” to new opportunities before they felt fully ready.

Featured image Digital Nomads Daily Podcast Episode 78 Is Remote Work Facing its Most Fruitful or Scariest Year With Liam.jpg

“Some people just aren’t really wired to be managed. I find myself so much more productive if I am telling myself what to do versus other people telling me what to do.”

Key takeaways from our freedom chat with Jake:

โžก๏ธย The psychological freedom effect: Even though entrepreneurs often work more hours than employees, having control over when and how you work creates a profound psychological freedom that transforms your relationship with work.

โžก๏ธ Say Yes, then learn to say No: Early in your entrepreneurial journey, saying yes to opportunitiesโ€”even ones you’re not fully prepared forโ€”forces rapid growth and skill development. As you mature, learning when to say no becomes equally critical.

โžก๏ธ The hidden economics of freelancing: Agency marketers managing six clients while making $60-80K could potentially earn $15K monthly by taking those same clients freelanceโ€”a dramatic shift in income potential that’s rarely discussed in traditional career paths.

โžก๏ธ Sustainable vs. unsustainable business models: Some business models (like dropshipping) have shorter shelf lives due to easy replication, while others (like growth marketing) offer medium-term sustainability before potential AI disruptionโ€”choose wisely based on your timeline.

โžก๏ธ The self-development accelerator: Entrepreneurship functions as “a self-fulfilling journey on steroids,” forcing rapid personal growth in areas like boundary-setting, communication, and self-discipline that transform far more than just your income.

Review the podcast to get instant access to our FREEDOM BOOSTER Framework Training

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Digital Nomads Daily Podcast Guest Hannah Dixon

Connect with Jake

Visit on LinkedIn @Jake Madoff

Website: www.jakemadoff.io

Learn everything about creating more freedom and live your dream life

Start a side hustle or build a freedom business โ€“ creating multiple revenue streams is the way to your freedom life. We show you how others do it successful too.

Get freedom business growth tips in your inbox ๐Ÿ’Œ
Join 4000+ digital nomads and freedom seekers!

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