In Episode 27, we explored the decision to start your own business. Now in Episode 28, we go deeper with someone who actually did it.

Todd Anthony spent 35 years in the marketing industry, working inside agencies and in-house at major companies before founding Pinwheel Content, a marketing agency based in San Francisco. In this conversation, Todd shares the real, unvarnished truth about what it takes to build a business from the ground up, especially when you have decades of experience and a lot of reasons to want more control over your professional life.

We cover the pivotal moments and practical decisions every aspiring entrepreneur needs to think about:

The Decision to Start: Todd explains how multiple layoffs became a catalyst, pushing him toward entrepreneurship as a way to reclaim stability and autonomy. After 30 years of being told what to do, he wanted to do things his own way. He also walks through how he structured his agency from day one to weather market volatility, keeping hard costs low and building a durable business model.

Financial Runway and Accounting: We dig into the hardest part of starting a business, which is giving up a predictable salary for uncertain revenue. Todd is candid about the need for savings, the reality of healthcare costs, and why the very first hire he made was a bookkeeper. His advice: if you lack a skill set, do not struggle through it. Hire it out. It is an investment that pays off.

Hiring Senior Talent: Todd reveals the dirty secret of the agency world, where senior people are paraded in pitches but junior staff do the actual work. His agency flips that model. He consciously hires experienced professionals, many of whom have been pushed out of corporate roles due to age. The result? Projects move like a dance. Clients are happier. The work is better and faster. And yes, it is ultimately more cost-effective. This is a powerful counter-narrative to the ageism that pushes talented people out of the workforce.

Tips for Aspiring Entrepreneurs: Todd offers grounded, hard-won advice for anyone sitting on the fence. Take the leap, but plan carefully. Get a business coach early. Do not be too proud to ask for help. And as Todd puts it, the universe favors the bold. Once you catch the entrepreneurial bug, it is addictive.

Whether you are reconsidering your career after 50, navigating a layoff, or simply ready to build something of your own, this episode is packed with practical wisdom from someone who has lived it.

Youth runs fast, but age knows the terrain.

Connect with Todd Anthony:

Todd Anthony on LinkedIn: https://www.linkedin.com/in/toddanthony/

Pinwheel Content homepage: https://www.pinwheelagency.com/

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