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

Thanks for listening to the Learning from Smart People Podcast!

Subscribe, leave a comment and follow us on social media:

Twitter: http://twitter.com/LFSPPodcast
Instagram: http://instagram.com/LFSPPodcast
Facebook: http://facebook.com/LFSPPodcast
LinkedIn: https://www.linkedin.com/company/lfsppodcast/
LinkedIn: https://www.linkedin.com/in/imroboliver/
YouTube: https://www.youtube.com/channel/UCbWV_LuUad7ZWuE9j5D9v-w

You can also use the "Contact" page on the "Learning from Smart People" website:

https://www.learningfromsmartpeople.com/contact

Rich Ermlick: How to Build Scalable Business Systems

Rich Ermlick joins Rob Oliver on this episode of the Learning from Smart People Podcast to talk about how to build “boring excellence” (a.k.a. Scalable Business Systems.) As the founder of Boring Excellence, Rich helps leaders develop simple, stable, and scalable systems that reduce chaos and produce consistent, sustainable results—in business and in life.

Here are some of the main points as Rob Oliver and Rich Ermlick talk about how to build boring excellence:

• • Rich’s journey from factory work to corporate consulting through Lean Six Sigma
  • The principles of operational excellence can apply to your personal life, too
• • True improvement isn’t about fixing problems—it’s about building on stability
  • The difference between recovery and real innovation
  • Root cause thinking: how to dig past surface issues to find what’s really in the way
  • Why excellence is often invisible—and how that’s actually a good thing
  • “Make the process boring so you can live fabulously”
  • Every persistent business problem is a personal issue at scale
  • The three personality traps that keep leaders stuck
  • The six-phase improvement cycle Rich teaches: from clarity to reflection

  Rich is offering two free 30-minute “bullet sessions” to the first people who comment on this episode on LinkedIn. He’s also providing a downloadable one-page framework outlining his improvement process—see below for the link!

  You can learn more about Rich Ermlick and Boring Excellence by connecting through the website or accessing the download below.

  Download: https://drive.google.com/file/d/1szUCPVt9P6wzva5zCGlB7suRwzuzESVW
  Connect:http://BoringExcellence.com

  Thanks for listening to the Learning from Smart People Podcast!

  Subscribe, leave a comment and follow us on social media:

  Twitter: http://twitter.com/LFSPPodcast
  Instagram: http://instagram.com/LFSPPodcast
  Facebook: http://facebook.com/LFSPPodcast
  LinkedIn: https://www.linkedin.com/company/lfsppodcast/
  LinkedIn: https://www.linkedin.com/in/imroboliver/
  YouTube: https://www.youtube.com/channel/UCbWV_LuUad7ZWuE9j5D9v-w

  You can also use the "Contact" page on the Learning from Smart People website:
  https://www.learningfromsmartpeople.com/contact/

John Louizes talks about how to scale your business on this episode of the Learning from Smart People Podcast with Rob Oliver. John is the owner and proprietor of Zeno’s taffy and ice cream shop. It is the world’s most famous taffy. He has expanded from a single store with 3 employees to 9 stores with over 50 employees. A super interesting guy, you will enjoy this interview and learn from it.

Here are some of the main points as John Louizes and Rob Oliver talk about how to scale your business:

· Zeno’s is a family operated business that started in Daytona Beach in 1948
· Having a family run business creates interesting management power dynamics
· Fear is a powerful motivator
· Growth can be a powerful and enjoyable experience
· Lower profit margins from multiple locations can be more profitable than higher profit margins from a single location
· Different generations have different skill sets and visions
· Reactive decisions are generally not good for business
· Identify your constituency and serve them
· Put your website on everything!
· There is no saltwater in saltwater taffy
· Be as creative as possible within your marketplace

You can connect with John Louizes and Zeno’s Taffy through the links below. When you order from the website, be sure to use the code “smart20” to receive your 20% discount.

Website: https://worldsmostfamoustaffy.com/
Twitter: https://twitter.com/FamousTaffy
Facebook: https://www.facebook.com/famoustaffy/
Instagram: https://www.instagram.com/zenoscandy/
LinkedIn: https://www.linkedin.com/in/johnlouizes/

Thanks for listening to the Learning from Smart People Podcast!

Subscribe, leave a comment and follow us on social media:

Twitter: http://twitter.com/LFSPPodcast
Instagram: http://instagram.com/LFSPPodcast
Facebook: http://facebook.com/LFSPPodcast
LinkedIn: https://www.linkedin.com/company/lfsppodcast/
LinkedIn: https://www.linkedin.com/in/imroboliver/
YouTube: https://www.youtube.com/channel/UCbWV_LuUad7ZWuE9j5D9v-w

You can also use the "Contact" page on the "Learning from Smart People" website:

https://www.learningfromsmartpeople.com/contact/