Beyond Curious ®

#250: The Steve Sims Trilogy: A Tribute to the Guest Who Deeply Impacted My Life — and Left a Legacy of Living Boldly, Passionately, and Without Limits


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Episode 250 of the Beyond Curious Podcast marks a huge milestone… and also carries a heavy heart.

This episode is dedicated to a podcast guest who profoundly impacted my life — and who left us far too soon.

His name was Steve Sims.

You may have heard me talk about Steve before. 

He’s the “Real Life Wizard of Oz” who helped his clients do things like:

  • Get married by the Pope
  • Take submarine trips to the Titanic
  • Have dinner in front of Michelangelo’s David while being serenaded by Andrea Bocelli
  • Meet celebrities like Elton John and Elon Musk

He even once took a group on a private tour of the Tesla gigafactory… followed by a visit to a legal, licensed brothel (yes, seriously).

But beyond the crazy experiences…

Steve Sims gave me a new blueprint for life.

In fact, a few years ago when journaling about the 3 people I most looked up to, Steve’s name was high on that list — right next to my wife and daughter.

Even though we only spent a few hours together across these interviews, Steve’s mindset has been running like a background program in my brain ever since I met him.

He embodied the values and passions that drive my life today:

  • Family & Heart: He loved his wife and kids deeply, and built his business alongside them
  • Doing the Impossible: His entire life was proof that “impossible” is just a starting point
  • Experiences: The most inspiring (and wildest) experience designer I’ve ever met
  • Fun & Play: He approached life like a big kid—joyful, absurd, and always ready to make you laugh
  • Being Unapologetically You: Steve knew who he was and never tried to be anything else
  • Pure Passion for Life: You could hear it in his voice—he lived with passion, every single day
  • Storytelling: Hands down my favorite storyteller of all time—he didn’t just live great stories, he delivered them in unforgettable ways

Steve passed away from cancer on July 7, just shy of his 59th birthday.

To honor his legacy, I’ve stitched together all 3 of our interviews in one place—for the first time ever.

So whether this is your first time hearing Steve or you’re revisiting his wisdom…

I hope this tribute inspires you to live with more passion, play, and purpose… and to imagine a life far beyond what you ever thought possible.


Show Notes Generated With The Help of AI!00:00 - Introduction to Beyond Curious and today’s guest, Steve Sims

Brandon Fong opens this emotional 250th episode with a tribute to Steve D. Sims, who passed away on July 7th. He introduces the episode’s purpose: to honor Steve’s impact through a compilation of their most meaningful past conversations. Brandon also shares seven personal reasons why Steve’s presence left a lasting imprint on his life and work.

05:14 - Discovering Steve: An Ice Bucket, a Stage, and Instant Connection

Brandon recounts seeing Steve for the first time online—dumping a bucket of ice over himself on stage—and being struck by his fearless authenticity. This moment set off a chain of events that led to their eventual connection and friendship.

08:23 - Steve’s Superpower: Creating the Seemingly Impossible

Brandon outlines the legendary experiences Steve was known for—like arranging a Vatican wedding officiated by the Pope and organizing a dinner at the base of Michelangelo’s David. He highlights that Steve’s gift wasn’t extravagance, but in designing moments with purpose and intention.

11:36 - The $1,700 Proposal Re-Creation That Rivaled Luxury

Steve shares the story of helping a client recreate his marriage proposal from 25 years earlier. The budget was modest, but the execution—complete with custom fencing, actors, dogs, and the exact location—demonstrated Steve’s belief that emotional resonance beats opulence.

19:14 - “That’s Not for People Like Us”: The Gucci Store Story

Steve recalls being a child and hearing his mother tell him that Gucci was “not for people like us.” That moment lit a lifelong fire of curiosity and rebellion, shaping his drive to push boundaries and create access where there was none.

26:04 - Velvet Rope Lessons from Bouncing in Hong Kong

Steve reflects on his time as a nightclub bouncer and how he curated guest lists using odd passwords like “peanut butter” to filter for fun, kind, and respectful people. This evolved into a life philosophy: control who gets access to you, your energy, and your time.

32:08 - “If There’s No Passion, There’s No Point”

Steve explains his life mantra. He shares how being “passionately ignorant,” a term his wife coined, helped him move forward without overthinking, trusting his drive to solve problems creatively and boldly.

36:01 - How Dinner with David Happened: Step-by-Step

Steve unpacks one of his most famous feats: hosting a private dinner at the foot of Michelangelo’s David. He explains the process from ideation to execution, emphasizing audacity, asking the right people the right questions, and solving problems others don’t even see.

42:13 - Turning a “No” into a “Yes” by Solving a Problem

Steve reveals how the secret to securing the David dinner wasn’t just in the ask—but in offering to raise funds for the museum’s roof restoration. He transformed his request into a solution, showcasing his win-win negotiation mindset.

45:45 - A Song for the Soul: The Andrea Bocelli Experience

Steve recounts organizing a performance by Andrea Bocelli for a client. When Bocelli sang the song that had personal meaning, the client was moved to tears. Steve reflects on how getting to the emotional core behind a request elevates an experience into something transcendent .

54:57 - Why “Why” Matters: Getting to the Root Desire

Steve dives deeper into the practice of asking “why” repeatedly with clients. He illustrates how this technique uncovers the emotional truth beneath a surface-level request—helping him design moments that leave a lasting legacy, not just a photo op.

01:03:58 - Transforming a Realtor’s Business by Going Deeper

In a story from his coaching, Steve shares how a real estate agent transformed her approach by asking clients why they were moving—not just what kind of house they wanted. The shift allowed her to create life-altering outcomes instead of basic transactions.

01:12:02 - Stop Asking “Can I?” and Start Asking “How Can I?”

Steve explains how reframing your internal dialogue from “Can I do this?” to “How can I make this happen?” is one of the simplest yet most powerful mindset shifts. It’s a practice that shaped his career and confidence.

01:18:43 - Death and Urgency: Building a Life That Matters Now

Steve reflects on the urgency that mortality brings. He argues that we often put off what matters most and encourages listeners to start building a meaningful life before time runs out.

01:24:56 - The Art of Going for Stupid

Steve breaks down the concept behind his book Go For Stupid. He explains how aiming for seemingly ridiculous goals strips away fear, judgment, and complacency—and ultimately leads to far more fulfilling outcomes than playing it safe.

01:30:27 - A Life by Design: Escaping Nothing

Steve and Brandon discuss what it means to build a life so aligned that you never feel the need to “escape.” Steve emphasizes conscious choices, meaningful work, and aligned relationships as pillars of a truly designed life.

01:42:01 - Being Authentically You (Even When It’s Uncomfortable)

Steve speaks about the power of showing up as your full, unfiltered self. He argues that authenticity acts as a sorting mechanism—it pushes the wrong people away and draws the right ones closer.

01:50:13 - What He’d Tell His 18-Year-Old Self

Asked what advice he’d give to his younger self, Steve answers without hesitation: start sooner, be bolder, ignore the doubters. He urges others not to wait for permission or ideal timing to chase audacious dreams.

02:01:04 - A Father’s Legacy in Action

Steve shares how he’s passed his values down to his son Henry—not through lectures, but by modeling them every day. His legacy, he says, is lived in real time, not defined by what he leaves behind.

02:14:46 - Brandon’s Final Tribute: Seven Ways Steve Changed His Life

Brandon concludes by sharing the seven deeply personal reasons Steve made such an impact on him. From helping him own his curiosity to challenging him to think bigger, Brandon reflects on the emotional depth and enduring lessons Steve left behind.


Links & Resources:

  • Steve D. Sims Official Website: Learn more about Steve’s work and legacy.
  • Henry Sims - Sims Media: Explore the ongoing legacy of Steve Sims through his son Henry’s media company.
  • Sims Distillery: A place for curated ideas, coaching, and inspiration from the Sims family.
  • Book: Bluefishing: The Art of Making Things Happen by Steve D. Sims
  • Book: Go for Stupid: The Art of Achieving Ridiculous Goals by Steve D. Sims

...more
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