Wilder Possibilities

Shelton Wilder || Hype Boss
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  • Entrepreneurship
  • Updated Biweekly

Welcome to the Wilder Possibilities Podcast! Join Shelton Wilder, a serial entrepreneur who received her "click" in 2016 when she dove into Real Estate quickly becoming one of LA's most beloved top agents. Shelton loves entrepreneurs, business owners and visionaries and wants to know their "click" – that moment of clarity when they knew they were onto something big. From sharing successes to unraveling the intricacies of building brands and businesses, this podcast celebrates the diverse journeys of creators and business owners.

  1. 2d ago

    It’s Never Too Late to Reinvent Yourself... A Lifetime of Lessons with Rob Wilder

    Hey! I'd love to hear your thoughts, send me a voice note! This may be Shelton’s most personal episode of Wilder Possibilities yet. A conversation with the man who watched her story unfold from the very beginning... her dad, Raboteau "Rob" Wilder. From wanting to completely “rebrand” himself as a young man to navigating the Vietnam draft lottery, Duke Law School, the Navy JAG Corps, federal prosecution, criminal defense, civil litigation, fatherhood, and five decades in the legal profession, Rob’s career was anything but a straight line. But this conversation is about much more than law. Shelton and Rob talk candidly about the decisions that change the direction of your life, knowing when it’s time to walk away from something that no longer feels right, taking risks without knowing exactly how they’ll turn out, supporting family through difficult seasons, and continuing to find purpose in your work at every stage of life. We dive into: The original personal rebrand of reinventing yourself (before it was a buzzword)How the Vietnam draft unexpectedly helped shape Rob’s path into lawKnowing when professional success isn't enoughFederal prosecutor to criminal defense, and the case that made him walk awayFatherhood, raising Shelton, and the teenage micro-eye-rollThe proposal Dad (almost) ruinedSometimes “the click” isn’t one dramatic moment. Sometimes it’s a lifetime of decisions, pivots, mistakes, risks, and the willingness to keep moving forward. Make sure you followWilder Possibilities for conversations about entrepreneurship, career reinvention, resilience, ambition, and the moments that change everything.

    It’s Never Too Late to Reinvent Yourself... A Lifetime of Lessons with Rob Wilder

  2. Sep 8

    Inman CEO Tom Bohn on the Future of Reinventing Real Estate With AI

    Hey! I'd love to hear your thoughts, send me a voice note! What does the future of real estate look like in the age of AI? In this conversation from Inman Connect San Diego 2026, Inman CEO Tom Bohn shares his journey into the residential real estate industry and his vision for transforming Inman for the next generation of agents and entrepreneurs. Tom and Shelton discuss Inman 2.0, new AI-powered tools designed to turn real estate news and data into hyper-local social media content, the importance of building an active year-round community, and Inman’s plan to bring 1,000 local storytellers and citizen journalists onto its platform. He also shares where he sees Inman heading over the next three years, including plans to grow the community, expand further into the real estate ecosystem, and strengthen the company’s team and partnerships.

  3. Aug 17

    How Jeremy Davis "The Door-Knocking King" Turned Rejection Into a Business

    Hey! I'd love to hear your thoughts, send me a voice note! Welcome back to Wilder Possibilities, hosted by Shelton Wilder — luxury LA Realtor, CEO, and female entrepreneur. This week: Jeremy Davis, the "door-knocking king," on trading a teaching career for door-to-door alarm sales in 115° heat, shadowing Utah's top producers to break into real estate, losing his father mid-career, and building a coaching brand by giving away free training instead of selling a course. We cover prospecting like a top producer, door-knocking safety for women agents, turning grief into purpose, and growing 65K+ followers by pushing through "the cringe." Follow Jeremy @DavisSalesTraining

  4. Aug 3

    Kristi Cook's Spill Sesh Journey | How an Anonymous "Tea" Channel Grew to a 700K+ Subscriber Media Career

    Hey! I'd love to hear your thoughts, send me a voice note! Welcome back to Wilder Possibilities, hosted by Shelton Wilder. Today's episode features Kristi Cook, creator of Spill Sesh, the pop culture and celebrity commentary channel with over 700,000 YouTube subscribers. For five years, millions of people watched her videos without ever seeing her face. Today, Kristi finally tells the whole story of Spill Sesh, starting with her origins in local broadcasting competitions led to building a 700K-subscriber pop culture channel. We dive into: Kristi's start in broadcast journalism as a teenager and her national student TV competitionsMoving to LA in 2016 and working her way up through TMZLaunching Spill Sesh anonymously in 2018 and the moment it went viralLeaving TMZ in 2022 to go all-in on content creationThe story behind her 2023 face reveal after five years anonymousWhat's next? Red carpets, her own podcast, and maybe even a documentary

    Kristi Cook's Spill Sesh Journey | How an Anonymous "Tea" Channel Grew to a 700K+ Subscriber Media Career

  5. Jul 20

    Transforming $1000 into a Thriving Business with 50 Stores Nationwide - Building Sugared + Bronzed with Courtney Claghorn

    Hey! I'd love to hear your thoughts, send me a voice note! Welcome back to Wilder Possibilities, hosted by Shelton Wilder — luxury Los Angeles Realtor, CEO, and female entrepreneur. Today's episode features Courtney Claghorn, Co-Founder & President of Sugared + Bronzed. In this conversation, Shelton and Courtney talk about how a $500 spray-tanning side hustle out of a Santa Monica apartment grew into a private-equity-backed beauty brand nearing 50 locations nationwide — and what it's really like scaling a business with your spouse. We dive into: Courtney's path from Chicago to Boulder, Colorado, where she met her husband and future business partner, SamThe "click" moment — how one frustrating summer of overpriced spray tans sparked the ideaBootstrapping from their living room to their first real storefront on Montana AveBuilding the Sugared + Bronzed brand and adding sugaring as the sugaring trend took off nationallyClosing their first (and only) private equity round with Main Post Partners — right before COVIDRunning a near-50-location business with your spouse, motherhood, and what's next for the brand Follow along on IG @sugaredandbronze / @courtneyclaghorn and book your appointment at sugaredandbronze.com Make sure to follow @wilderpossibilities on Instagram so you never miss an episode and share the love

    Transforming $1000 into a Thriving Business with 50 Stores Nationwide - Building Sugared + Bronzed with Courtney Claghorn

  6. Jul 6

    From Us Weekly to Building Her Own PR Empire with Emily Blair

    Hey! I'd love to hear your thoughts, send me a voice note! One tweet about spotting Cameron Diaz changed the whole direction of her career. Welcome back to Wilder Possibilities, hosted by Shelton Wilder — luxury LA Realtor, CEO, and entrepreneur. This episode: Emily Blair, founder of Emily Blair Media, on going from red carpet journalist to celebrity publicist. We dive into: Her click moment at 17Working the red carpet beat at Us WeeklyWhy "no ego" is the real key to success in this industryBuilding a 25-person PR agency from a pandemic side hustleThe truth about celebrity crisis management @emilyblairmarcus | Emily Blair Media | Substack: Off the Record

    From Us Weekly to Building Her Own PR Empire with Emily Blair

  7. Jun 22

    Building a National Insurance Empire | Alison Myers on Leadership & Healthcare Transparency

    Hey! I'd love to hear your thoughts, send me a voice note! Alison Myers, President of Corporate Benefits at Venbrook, joins Shelton to talk building a national insurance practice from scratch, leading a team through a pandemic and an acquisition, and why most people have no idea how much of their healthcare is already free. We dive into: Building a benefits practice solo, then scaling through COVID and an acquisitionHer "shepherd" approach to servant leadershipHealthcare price transparency in 2026, what's changing and why it mattersFree preventive care most people never useUsing AI to ask smarter health questions (without letting it replace your doctor)Navigating divorce and redefining "thriving" as an empty-nest mom🔗 Connect with Alison: https://www.linkedin.com/in/alimyers/ https://venbrook.com/advisors/alison-myers 🔗 More from Shelton: @sheltonwilderestates @wilderpossibilities

    Building a National Insurance Empire | Alison Myers on Leadership & Healthcare Transparency

  8. Jun 8

    James Harris on Real Estate, Reality TV & Building Breezy

    Hey! I'd love to hear your thoughts, send me a voice note! Welcome back to Wilder Possibilities, hosted by Shelton Wilder - luxury Los Angeles Realtor, CEO, and female entrepreneur. Today's episode features James Harris, founder of Harrison Partners and co-founder of Breezy. In this conversation, Shelton and James talk about what it really takes to build a career and a company from nothing but instinct and refusal to fit the mold. We dive into: Growing up in London as a rule-breaking only child with severe ADHD, a single mom, and a passion for selling out of car boots at age 10How James landed his first real estate job at 15½ by walking into a London brokerage with a photo instead of a résuméMoving to LA at 21 for a "gap year," falling in love with the city, and building a real estate business from the ground up with zero local contactsGetting cast on Million Dollar Listing Los Angeles after just one year in the business, filming ~100 episodes, and why he's equally proud to have moved onThe origin of Breezy, a full operating system for real estate agents featuring Underbuilt (instant build potential data), AI-powered comp reports, a real estate-specific note taker, and a complete deal pipelineA candid closing conversation about sobriety, ethics, keeping your side of the street clean, and channeling addictive energy into building something greatMake sure to check out James Harris on Instagram at @jamesbondst @breezy.ai @harrisandpartners to follow along for more exciting updates. WATCH MORE WILDER POSSIBILITIES Subscribe for inspiring conversations with entrepreneurs, creatives, industry leaders, and big thinkers shaping what’s possible.

    James Harris on Real Estate, Reality TV & Building Breezy
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About

Welcome to the Wilder Possibilities Podcast! Join Shelton Wilder, a serial entrepreneur who received her "click" in 2016 when she dove into Real Estate quickly becoming one of LA's most beloved top agents. Shelton loves entrepreneurs, business owners and visionaries and wants to know their "click" – that moment of clarity when they knew they were onto something big. From sharing successes to unraveling the intricacies of building brands and businesses, this podcast celebrates the diverse journeys of creators and business owners.

Information

  • Creator
    Shelton Wilder || Hype Boss
  • Years Active
    2025 - 2026
  • Episodes
    60
  • Rating
    Explicit
  • Copyright
    © 2025 Wilder Possibilities
  • Show Website
    Wilder Possibilities

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