When you talk to coaching expert Cliff Ravenscraft about how to build an online business, you quickly realize you’re speaking to someone who has lived multiple professional lives, all in the pursuit of one question: What if you could get paid to do what you love most? On a recent episode of DissedMedia: A Startup Story, Ben sat down with Cliff, best known as “The Mindset Answer Man”, to unpack how he turned his passion of a hobby podcast into a thriving and profitable coaching business that’s helped thousands of creators, executives, and coaches think bigger about their own potential.
From Hobbyist to Industry Pioneer
Cliff began podcasting in 2005, long before “podcast” was a household term. What started as a passion project about the TV show Lost exploded overnight after Entertainment Weekly picked up one of his theories. Within months, his small blog and show had reached tens of thousands of listeners around the world.
But behind that early success was relentless work, hand-coding RSS feeds, editing audio by hand, and uploading files over dial-up speeds. “There were no tools, no podcast hosting companies. You had to love it to do it,” he told Ben.
The Leap and the Burnout
After 18 months of juggling a full-time insurance job and multiple shows, Cliff took a leap of faith: he left the family business, founded by his grandfather in 1937, to podcast full-time. The timing? January 2008. The middle of a global recession.
That first year nearly broke him. “I worked seven days a week, 12 to 14 hours a day without a single day off,” Cliff said. “I made only $11,000 that year, and I ended up in the hospital.” The turning point came when he realized passion alone wasn’t enough. “I didn’t have the mindset of a business owner. I had the mindset of an employee.”
Rebuilding with Purpose
Recovery led to reinvention. Cliff immersed himself in personal development, reading The 4-Hour Workweek and 48 Days to the Work You Love. He began designing a life-first business model, one that started not with the content, but with clarity.
His breakthrough came when he developed an 11-step formula for building a profitable online business. Step eight? Create content. “Most people start there,” Cliff said. “But if you skip the first seven steps, knowing what you want, defining your value, identifying your ideal customer, you’ll spend years struggling.”
From Podcast Coach to Mindset Mentor
Cliff eventually launched Podcasting A to Z, a four-week online program that taught creators to build and scale shows strategically. Over a decade, he trained more than 40,000 people, earning as much as $750,000 in a single year. But even that, he realized, was just the beginning.
Today, Cliff’s focus has evolved beyond podcasting. Through his Building an Online Business course and one-on-one coaching, he helps high performers and leaders master mindset and build businesses around the lives they truly want. “You have to put your own oxygen mask on first,” he says. “When you have margin, financially, mentally, spiritually, you can finally create from abundance.”
The Takeaway for Founders and Creators
Ben reflected on the parallels with DissedMedia’s own journey, creating content for love, not yet profit, and Cliff’s advice landed squarely: “Doing what you love will get you through the first year. But to sustain it, you need clarity, purpose, and a model that works.”
If you’re building something from scratch, Cliff’s wisdom applies:
Start with your life vision. Define your value. Know your audience’s pain. And don’t just chase content, build systems that give your work room to grow.
Learn more about Cliff Ravenscraft:
cliffravenscraft.com
For a limited time, listeners of DissedMedia can access Cliff’s Building an Online Business course for $499 (normally $2,000), plus a free 90-minute coaching session when completed within 90 days. Email cliff@cliffravenscraft.com and mention DissedMedia.
Watch his free mindset training at mindsetanswerman.com/free.
