1348: HAPPY 2026! Kicking off the new year + your PASSION is your next PIVOT w/ special guest Ian Westermann

2026-01-01

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To kick off 2026, Brian is joined by his good friend and fellow entrepreneur, Ian Westermann of Essential Tennis, for a raw, unfiltered conversation about the real journey of a long-term creator. They pull back the curtain on the emotional highs and lows of building a content-driven business, from the thrill of growth and scaling a team to the painful reality of market saturation and the need to pivot. This episode is a must-listen for any entrepreneur feeling the grind of organic content. You'll get a rare, honest look...

💡 What You'll Take Away For YOUR Business

Why the "organic content grind" that worked in the 2010s is a death spiral now, and how to start pivoting your strategy for 2026.
How to combat the loneliness of entrepreneurship by shifting from a one-way content model to building a genuine two-way community.
The emotional journey of scaling a business up and then back down, and how to find gratitude and excitement in being a solopreneur again.
How to leverage your entire library of past content as an unbelievable training asset for AI, sparking fresh ideas you've never thought of.
The critical importance of "play" – how geeking out on unrelated hobbies can unlock unexpected skills and lay the groundwork for your next business venture.
A powerful mindset shift: viewing your business's growth not just for yourself, but as a vehicle to provide opportunities and support for your team.

📝 About Ian Westermann

Ian Westermann is the founder of Essential Tennis, the world's #1 online tennis instruction resource. Since 2008, he has built a content empire, publishing over 4,000 videos and helping millions of players improve their game. Ian is not just a world-class coach; he's a seasoned entrepreneur who has navigated the incredible evolution of digital media for over 16 years. His unique perspective comes from experiencing the full cycle of the content creator economy, from being a trailblazing pioneer to competing in a now-saturated market, offering invaluable, hard-won lessons for any business owner today.

🎯 Ian’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"If you're not excited about the thing you're working on, you will never, ever, ever put in the hours or ever, ever follow through enough times to ever have a chance of being good enough at that thing to be able to charge any money for that product or service."

📢 Memorable Quotes

“Humans are just not wired to just yell into the void and feel whole. I don't think it's okay to want that two-way street.” – Ian Westermann
“I’m just coming back around again to being excited about being a solo creator again… learning to be grateful just for that again, which I know there's people listening that are like giving me the middle finger right now if you don't already have your own business.” – Ian Westermann
“Just being able to get outside your own head… especially when you don't have a team… It's unbelievably powerful.” – Ian Westermann on using AI as a strategic partner.

🔗 Links & Resources