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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