In this episode of the Learning from Smart People Podcast, Rob Oliver talks with Jessica Eastman Stewart, founder of the Joyfully Managed Team. A former nonprofit executive turned systems strategist, Jessica shares how leaders can create joyful, productive teams and more ease in their own leadership. From implementing a “Polish Week” to embracing authentic appreciation practices, this conversation is packed with insightful, practical advice to help your work life run smoother and feel better.

Here are some of the key points Rob and Jessica discuss:

• Why joy might actually be the whole point of life—and leadership
• The importance of diversity in team-building and decision-making
• Why self-awareness matters when assembling or managing a team
• How executive coaching can reveal hidden leadership blind spots
• What a “Polish Week” is—and how it helps clean up cluttered systems
• Examples of tasks you can tackle during a Polish Week (like decluttering tabs!)
• How systems and structure can create space for more joy and ease
• The myth of constant productivity and why “cleanup time” is essential
• Strategies for managing tabs, bookmarks, inboxes, and brain clutter
• The power of declaring “inbox bankruptcy” to reset your workflow
• Why appreciation is one of the most effective joy-generators for teams
• Different languages of appreciation and how to tailor them to your people
• How leaders can use reminders and planning to make appreciation routine
• Why symbolic gestures can be just as meaningful as tangible rewards
• How Jessica uses email, Instagram, and freebies to spread joyful leadership tips

Jessica offers a free editable "Polish Week Checklist" to help you get started with tidying up your systems: https://bit.ly/Polish-Up-My-Systems

You can learn more about Jessica and connect with her through these links:

• Website: www.jessicaeastmanstewart.com
• Instagram: @joyfullymanagedteam
• Twitter: @jessicaestewart
• LinkedIn: Jessica Eastman Stewart

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In this episode of the Learning from Smart People Podcast, Rob Oliver talks with Nikki Bradley about how to build a powerful personal brand. Nikki is a brand strategist and authentic messaging expert who helps her clients show up as the boldest, truest versions of themselves. Drawing from both her corporate background and her own entrepreneurial journey, she shares practical insights and a powerful framework for creating a brand that resonates.

Here are some key takeaways from Rob Oliver and Nikki Bradley’s conversation:

• Your brand starts with your identity: you must see yourself clearly to be seen by others.

• Authenticity is magnetic—your audience connects when you show up as the real you.

• Saying “no” is a form of self-care and a boundary-setting skill worth mastering.

• Avoid the trap of imitating others online; your uniqueness is your superpower.

• Personal branding involves a balance of purpose, passion, blind spots, and your innate gifts.

• Feedback from close connections can reveal unseen strengths and clarify your personal brand.

• Branding is more than a logo or website—it’s about clarity on your values and messaging.

• Ideal clients share your values; think psychographics, not just demographics.

• Nikki’s “airplane test” helps identify clients you’d genuinely enjoy working with.

• Success is more likely when you stop trying to do it alone and seek the right support.

• Branding requires knowing the exact problem you solve and articulating it simply.

• Your name should be associated with a key problem your clients face.

• Tools for branding include social media, clarity on your “why,” and consistent visibility.

• Your operating system—how you run your business—can support or sabotage your branding.

• Building a business aligned with your purpose leads to more joy and less hustle.

• Faith, values, and personal alignment play a central role in Nikki’s brand philosophy.

You can connect with Nikki Bradley and access her free resources here:

• Website: nikkibradley.net

• Free Masterclass: $100K in 90 Days Masterclass

• Facebook: NikkiFBradley

• Instagram: @thenikkibradley

• LinkedIn: Nikki F. Bradley

Thanks for listening to the Learning from Smart People Podcast!

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

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• YouTube: https://www.youtube.com/channel/UCbWV_LuUad7ZWuE9j5D9v-w

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

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
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LinkedIn: https://www.linkedin.com/company/lfsppodcast/
LinkedIn: https://www.linkedin.com/in/imroboliver/
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You can also use the "Contact" page on the "Learning from Smart People" website:

https://www.learningfromsmartpeople.com/contact