It’s episode 100 of Live in the Feast! For this special episode, Matt Medeiros interviews Jason about his journey to freelance success, navigating tough life and business decisions, what he’s learned about networking and adding value, and why shutting up served him in unexpected ways.
Today’s co-host is Matt Medeiros, host of the Matt Report podcast and the Director of Podcast Success at Castos. To mark episode 100 of Life in the Feast, Matt will be taking the reins and interviewing Jason about his 10-year “overnight” success story.
Back in 2012, Jason was forced to choose between paying rent and his cable bill. His bed or his business. And even deeper, his passion or his family. At that moment, Jason made the tough decision to end his freelancing career and return to a job for the sake of his then-fiancé. However, when he broached the subject with her, she reminded him that freelancing was his dream. She encouraged him to keep on trucking a little longer.
So that’s exactly what he did. Rather than throw in the towel, Jason re-examined his business, raised his prices, and doubled down on a new niche. He kept grinding and ended up on the other side.
Almost a decade later, Matt talks with Jason about his journey to freelance success, navigating tough life and business decisions, what he’s learned about networking and adding value, and why shutting up served him in unexpected ways.
“Everything that I try to do from the business perspective is to serve the customers, but also see where a trend is headed and try to cater to that in some sort of fashion.” ~ @rezzz
Main Takeaways
- Staying a generalist won’t lead you to success. While it’s tempting to say yes to everyone, especially as your business is still launching, focus on figuring out what your niche is and then double down on it.
- If you’re struggling to find your niche, go straight to your clients and see what they need help with. Look for trends and determine where your expertise aligns with a common need.
- Fill in the gaps of your knowledge and expertise by outsourcing and finding wise mentors whenever possible.
- The key to success with clients is learning to listen. Spend more time hearing what their needs are and observing things about their life and business. Listening always pays off.
- Start adding free value in the communities you live and influence in. The more people you can help, the easier networking and growing your business will become.
- Matt Report
- The We Are Here Podcast
- Castos
- Alex McClafferty
- Ruby On Rails
- WooCommerce
- WordPress
- Curtis McHale on Saying No
- The WP Elevation Podcast
- Drip
- ConvertKit
- NurtureKit
- Rezzz.com
- WP Mentor Site
Links and Important Mentions
Stay in Touch
Season 9: Building a Profitable Service
More episodes in this season:

S09 E01 - Prioritizing Process, Delegating Smart, and Doing What You Love with Austin Church

S09 E02 - Staying Curious, Capitalizing on Your Network, and Adding Value with Samar Owais

S09 E03 - Intentional Parenting, Handling Social Media, and Scheduling Me-Time with Rob Roseman

S09 E04 - Finding Your Niche, Building an Audience, and the Art of Podcasting with Joe Casabona

S09 E05 - Doing Your Research, Communicating ROI, and Innovating Outside Your Niche with Eman Zabi

S09 E06 - How To Pivot, The Secret to Great SEO, and Why Business Is More Important Than Craft with Tom Hirst

S09 E07 - Stacking Power-Ups, Maintaining Focus, and the Art of the Steal with Eric Siu

S09 E08 - Understanding Emotional Data and Listening to Your Audience with Adrienne Barnes

S09 E09 - Launching a Business, Finding Balance, and Staying Valuable

S09 E10 - How Specialties Lead to Priceless Referrable Moments with Chase Dimond

S09 E11 - Differentiation, Reputation, and Pivoting From the Top-Down with Peep Laja