In this episode of the Learning from Smart People Podcast, Rob Oliver talks with Chris Castanes—an award-winning insurance agent, speaker, and author of You Are Going to Be Great at This. Chris brings decades of sales wisdom with a refreshing blend of humor and authenticity. Whether you're a reluctant entrepreneur or a seasoned salesperson, you'll appreciate Chris’s real-world insights on what it really takes to succeed in sales—without the sleaze.
Here are some of the key takeaways from Chris Castanes’ conversation with Rob Oliver:
Sales success starts with learning how to find people to talk to.
A full pipeline and consistent networking are essential to growth.
Rejection is part of the process—develop “Teflon coating” and keep moving.
Toastmasters and public speaking can help introverts build communication confidence.
Sales isn’t just about product—people buy from people they trust.
Building rapport and demonstrating integrity beat pushy tactics every time.
Relationship selling means showing up sincerely, not just closing a deal.
You're always selling yourself—in business and in life.
Humor and resilience can defuse rejection and create memorable moments.
“Selling on the approval of others” taps into a powerful psychological motivator.
Real-life examples (like Popeye and spinach!) make sales techniques relatable.
Listening is more powerful than talking—find the client’s real pain point.
Be genuinely curious about your client’s needs, not just your pitch.
Follow up consistently; a client’s circumstances can change unexpectedly.
Keep multiple solutions “in your quiver” to serve evolving needs.
Transitioning to virtual and social media-based sales requires creativity and adaptability.
The barrier to entry on social media is low—standing out requires strategy.
Your name is your brand—keep it consistent and focused.
Avoid diluting your identity with conflicting side hustles.
Chris’s humor-infused book was a passion project turned powerful teaching tool.
You can learn more about Chris Castanes and connect with him through the links below:
Website: www.chriscastanes.com
Twitter: @ccastanes
Instagram: @chriscastanes
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