Backstage w/ Matt Stone

Thirty-eight days until summer, and welcome to Backstage’s new Friday cadence. Matt’s breaking in a new format like new shoes, seeing what works best. This week started with a networking event with trades owners in southeastern Pennsylvania—flooring, painting, roofing companies. The vibe: more competition, people getting more bids and hanging on longer, not pulling the trigger as quickly. General unease about the economy. If you’re feeling like things aren’t moving, it’s likely not just you. Economic forces bigger than you individually are at play. When you’re hyper-focused on deals you’re getting or not getting, it can feel desperate. Just know there are forces out there impacting your business.

He met Paul, a former chef who switched to real estate decades ago. That chef identity is still inside him, yet he’s all in on real estate—finding ways to bring his culinary background into the work. Differentiation in places like Manhattan is critical, and Paul’s creative edge lets him use kitchen metaphors people relate to. Reminder: if you’ve made a big pivot, you don’t lose that career. It continues inside you. Matt thinks about his law background—he struggles deeply with having a law license and not practicing, even years later. There’s a little bit of regret. If you’re feeling like that, it’s normal. Paul showed him what it looks like to go all in on a new career without losing the old one entirely. It’s an identity issue, a matter of reframing and being in full acceptance that you’re already enough.

Yesterday: slew of meetings with unique, interesting people. Reminder—networking questions like “how long have you been doing that?” are fine, better than staring into oblivion. But when you ask “What are you excited about? What are you working on? What’s floating your boat right now?”—conversations get more interesting much more quickly. Our past is important, but it’s far more interesting if we bring it up selectively and intentionally. Same with the future—asking what someone’s excited about unlocks more than asking where they’ve been.

Now something deeply personal: his 95-year-old grandfather passed away early this week. Matt’s one of the luckiest grandsons on the planet—firstborn grandchild, had an active grandfather in his life for 51 years. Gramps supported him when he wanted to travel Vietnam for a month, gave him his first car (a Volkswagen Diesel Dasher Wagon), valued education so much he’d do almost anything to help with it. More than anything, Gramps loved people. After Matt’s grandmother died years ago, every year he’d go on and on about how much he missed her. There were never strangers, only people you had to get to know. Random people would roll into the family sphere. They did home exchanges in Europe, have French family not blood-related but closely tied because of them. What a gift. Gramps will forever live inside him, and Matt will never stop trying to impress him—that’s a good thing.

No matter what hardships you’re going through—business, life, economy—it’s always about the people. That’s how we get through this period. Three things for getting through difficult times and building something new: (1) Create healthy feedback loops, especially with great clients who give clear information back. (2) Have something you can control—gardening, baking, gym, parasailing, whatever. (3) Remember to stop, rest, celebrate. Last week he had his birthday party with a dozen people in a Manhattan lounge—one of the most joyful nights. It’s important to gather people and celebrate what you’ve done. There are so many difficult things—loss, market changes, loss of relevance from external factors. We don’t bounce back, we learn forward. The pain stays with you, but through it, if you connect and learn and grow, you become stronger.

Title: 51, Grateful, and Balancing Confidence with Humility

Subtitle: On birthday reflections, upcoming celebrity guests, structured interviews as the secret to books and courses, and showing up meaningfully

Description:

Forty-five days until summer, and Matt’s celebrating his birthday today—51 years old, grateful to be healthy with so many wonderful people in his life. He shares the same birth date (year and day) with Enrique Iglesias. After trivia about Harry Truman (1884), Don Rickles the roaster (1926), Melissa Gilbert (1964), and Coca-Cola going on sale (1886), he dives into what’s been a consequential week.

The Bigger Stage podcast has exciting guests coming: an executive at a music AI company (focusing on his journey through the industry, not the company itself), a founder from the Dominican Republic who built a global business helping small businesses with loans, and a Hollywood celebrity—former game show host and contestant (won over $100k many years ago), came through improv at Second City, had a show on Travel Channel, been in movies, TV, lots of voice acting. Won’t say the name yet. The conversation will be about reinvention, creativity, human psychology—staying curious, being a generalist, learning things you didn’t before. That’s how we adapt, apply creativity. Several episodes in the can waiting to be edited, sticking with every-other-Saturday cadence for now.

Working with clients, he’s seeing that everyone—regardless of pinnacle reached—faces some level of imposter syndrome, a view of themselves that’s not completely accurate. One of the great joys of this work is helping people reframe how they look at and talk about themselves, balancing humility with confidence. You can be highly confident and still humble. That combination of confidence, clarity, and humility is powerful. Right now there’s going to be increasing thirst for people who embody this—because we’re not seeing it from certain people with levers of power. Arrogance blinds you, makes you less self-aware, the bubble gets thicker, obscures reality, kills the feedback loop. Why do you want to be well-known? For fame or to make a difference?

In-person events are coming into picture—curating the right IRL experiences will be more important. That’s a priority for later this year. And here’s the confirmation of a founding assumption: busy business owners wanting to write books, handbooks, workbooks, courses struggle with blank pages. Structured interviews over time are a great place to start. The data you collect, the transcripts—with the right AI tools—give you an incredible way to start filling out outlines for books, courses, keynotes, articles. Doesn’t do the whole job, but makes it easier to move forward. A refuge where you can reflect verbally and be far ahead of the game. This is proving really effective.

On his birthday, the biggest feeling is gratitude—for his amazing wife, the clients, the partners. Moved to NYC over four years ago with wonderful friends around the world, and now has a New York metro group of creative, brilliant people he’s honored to call friends. Life keeps getting richer. His job is to give the world his very best and show up in the best way he can. The question: How do you want to show up this weekend and beyond? What would be most meaningful for you? Iconic Conversations in May—only 20 slots, email [email protected] to get on the list.

After six months of daily episodes, Matt is making a change. This pod is shifting to a weekly Friday cadence — a backstage-style check-in built for summarizing the week’s learnings, previewing what’s next, and pulling listeners deeper into the journey. The daily format helped build the stage. Now the stage is set, and it’s a different game.

In this midweek bonus, Matt also unveils Iconic Conversations — a new application-only series capped at 21 people, kicking off May 28th with messaging expert Shannon Hernandez. Plus a quick trip through May 6th history (the Chunnel, Babe Ruth’s first home run, and the patenting of the ice machine) and a question worth sitting with: where are you focusing your own clarity and power?

Fifty-four days until summer, and Matt’s got a feeling they’re going straight from late winter into the Hades era of heat. Welcome to Backstage—he likes the art, hopes you do too, sticking with it for a while. After sharing trivia about the yellow fever vaccine (1932—back when vaccines were seen as positive), Charles de Gaulle resigning (1969), and A Chorus Line closing after 6,137 performances (1990), he dives into the flight analogy that’s been on his mind.

Flying has always been exciting since he was a kid—first plane ride probably when his father was deployed to Europe, TWA, smoking on the plane where the only difference between smoking and non-smoking was the seat number. Flight is a great analogy for starting a new venture. The Bigger Stage is a few months old, still an infant. The plane has left the tarmac, back wheels are off the ground. Great. But here’s the thing: takeoff and landing are the most dangerous parts of a flight, when most crashes happen. Like car crashes in parking lots near your home, not on the freeway. It’s normal to feel very vulnerable after takeoff because you are vulnerable. It’s precarious—you’ve got to believe the parachute will deploy. Usually there’s a first round of excitement from people you know closest (like angel investors or family and friends), then you’ve got to raise money from people who don’t know you as well. That’s where they’re at with The Bigger Stage.

But here’s what’s exciting: the operator-to-icon shift is really resonating. People get it viscerally. The more he sees the world through this lens—what is iconic, how to become iconic in your lane, industry, community, company—it’s such a great frame. It’s where we’re at in the market. People want to know people they can trust even more than brands. They want to see your work, how you think. Sharing that can come in many expressions. There’s going to be more art than ever in the age of AI.

Headlines on what’s launching: (1) Iconic Introduction workshop with colleague Mike Verrett—eight-step process to develop your perfect pitch, then capture it on camera with clips you can use for your website, less than $1,000, super high value. (2) Iconic Interviews—small group (max 21 people), once a month with special guests, private workshop environment with breakout discussions around developing iconic energy, messaging, presence. (3) Exclusive invite-only dinners in Manhattan. The creative process of putting all this together brings great joy. First truly celebrity guest coming to The Bigger Stage—stand-up comedian from Second City. If you’re interested, email [email protected] and reference Backstage for preferential priority. Thinking one day a week (Friday morning) for this podcast, maybe two. Let him know what you think.

Fifty-eight days until summer, still chilly, and it feels like they’re going straight from late winter into summer with something brutal in between. Welcome to Backstage—the podcast is officially rebranded. Cadence still TBD, aspirationally five days a week but thinking three for consistency. Things are changing, lots more activity. Planning a very exclusive, very cool invite-only dinner concept, probably launching in June. After sharing trivia about the Library of Congress being established (1800) and the soda fountain patent (1833—almost 200 years of bubbles), he reflects on yesterday’s 21st anniversary of the first YouTube video. In the grand scheme, 200 years isn’t that long either.

Here’s what’s taking shape with The Bigger Stage: shows, the main podcast, networking and community events, plus he’s adding opportunities for people to record themselves talking about what’s important for their business—doing their pitch, having a conversation about it, getting artifacts to help integrate it into their psyche and go off-book faster. Yesterday he met with people from LinkedIn, talked about AI challenges and threats, but also how everyone’s using it. Nobody’s saying they’re not. So the question becomes: how can humans best collaborate to do what only humans can do? That’s what The Bigger Stage is all about.

Example: He doesn’t have time to manually write podcast descriptions every day, so AI takes his transcript and turns it into a description. He reads it, sometimes makes changes, but the ROI isn’t there to spend forever on it. He’s grateful for that. However, the only reason it works is because it’s taking a transcript of what he’s already said without AI. When AI takes things you’ve done that are original work, great. But if you surrender your thinking to AI, that’s not going to produce something he wants out in the world. Even when using it to help write, he writes pretty fulsome pieces, then treats AI as his editor, not his writer.

The Bigger Stage is creating stages for people to express themselves more effectively, entertainingly, engagingly—bringing out more humanity in messaging as we build businesses, movements, influence to make the world better. The question: What are you doing today to cultivate collaborative relationships? Partnership isn’t as easy as it sounds. It takes real intention and humility to pull off truly great collaboration—different incentives, even with good people. Things have to be very aligned, high trust. But we’re going to need more partnerships moving forward, not fewer. So we’ve got to get better at humaning.

Title: 21 Years Since the First YouTube Video

Subtitle: On burgeoning friendships, the ground shifting faster than ever, and bridging where technology meets human creativity

Description:

Fifty-nine days until summer, and Matt’s pondering frequency—maybe three days a week instead of five. Let him know what you think. Last night he had dinner with David Kalinowski (author of The Sacrifice Paradox), a podcast guest who’s become a burgeoning friend. One of the great joys of podcasting: meeting people who become part of your life. After sharing trivia about the Church of England annulling Henry VIII’s marriage (1533), Natalie Wood showing up to accept Harvard’s worst performer citation (1966—bold move), and the first YouTube video being uploaded 21 years ago today (2005), he dives into what’s on his mind.

Twenty-one years. He can remember pre-YouTube like it was yesterday, yet he can also go long periods thinking YouTube always existed. It’s become integral. Maybe it’s like when TV first came out—but TV projected entertainment into your home, a one-way street. YouTube is semi-open source. Anyone with a little equipment can play, whereas television wasn’t like that. Reality has changed. And here’s the thing: imagine 21 years from now—how much will be different then. There’s no resting on your laurels, no “I got this, I figured things out, I’ve learned all I can learn.” Not if you want to play in the world, grow, have opportunity.

The one thing he knows for sure: there’s a lot he doesn’t know. He continues to marvel at creative things people are doing—some he wants to learn from, some he doesn’t. But knowing what’s out there is powerful. Everyone is touched by changes in technology. With The Bigger Stage, he’s trying to bridge where technology meets the best of human creativity—where’s the stage the human belongs, and what technology supports getting there, spreading the word, being most creative and most human. Finding that at any given moment is critical, with the understanding it’ll keep changing.

So triple down on learning new things. Doesn’t mean spending thousands on courses—there’s free information everywhere. For him it starts with curiosity: asking people what they’re doing, what they’re seeing, what they’re paying attention to. Often they’re noticing things he’s not, sometimes things he didn’t know existed. Keep learning, stay curious, keep building. The ground is shifting always, faster now. You can’t control it, so get on with making relationships, learning, leaving a legacy of curiosity, service, connection, love. That’s what it’s all about. New podcast art—officially the Backstage podcast now, behind the scenes of The Bigger Stage. Shout out to his sister Katie who helped inspire the name.

Fifty degrees and chilly in NYC, and Matt went underdressed to last night’s fantastic networking event—froze afterward grabbing a slice with a friend, but good times. After sharing trivia about the first White House Easter egg roll (1878—still creepy with the bunny), Jacques Cousteau’s diving apparatus patent (1952), and the Blues Brothers’ first SNL appearance (1978), he dives into what’s shifting.

The networking event was run by Lisa, truly one of the best facilitators he’s ever seen. She even did a meditation at the end, which reminded him of facilitating a global distributor meeting in Rome years ago for a Japanese cosmetics company—he felt self-conscious doing a meditation then, worried people would think he was woo-woo, but maybe they liked it. Here’s the shift: this show, which started as a daily journal while building The Bigger Stage, has a different function now—refined, elevated. He’s rebranding the Substack channel to “Backstage”—the backstage of The Bigger Stage. The show will be the Backstage podcast, where he can publish written material and really build it out. Coming week he’ll finish the rebrand, get artwork made (maybe AI first, then have someone make it well).

Now here’s the big idea: he wants to curate a dinner in Manhattan every month—very curated, new fabulous or quirky location each time (undiscovered gems). He’s partnering with someone who specializes in finding these places and his friend Meredith from improv. The concept: interactive, fun, maybe not even in a restaurant per se—bring in food, people pre-order, but make it about content creation. Interview each other, make videos, but in a fun way that makes it easier. Because we’re more creative in league with other people. Everyone walks away with not just an unforgettable memory but artifacts they can use for marketing or business. They’ll cast for the dinners. If you’re in NYC and interested, email [email protected].

Right now his brand is like a house where the bathroom on the second floor works but not everything’s connected and unified. So much progress, but it’s never done. Frequency of the podcast is shifting too—maybe three times a week on committed days. Not going away, just elevating, maturing, moving to the next stage. The question: What’s your next stage, and what do you need to get there?

Down to a lovely 77 degrees after almost 90 yesterday (65 days until summer), and Matt’s happy about it. Last night’s nonprofit event was packed with sweating professionals in jackets—met two women from Colombia working for a nonprofit, a writer, all kinds of interesting people. Not a community he’s heavily involved in, but he felt part of it instantly. Good for the soul. After sharing trivia about pineapple-shaped cheese (1810—truly a gift to humanity), Geraldine Mock’s solo flight around the world (1964), Apollo 13 returning safely (1970), and a six-pound goldfish caught in California (1996—imagine that thing), he dives into what’s really on his mind.

He’s tired but working on next week’s presentation for a networking group. Yesterday the curtain started pulling back—the flow, a self-assessment, the stories and data he’ll bring in. Now he just needs to distill it down into something punchy and interactive. He’s 85% there. Put the call out and it comes. But here’s the thing: building any business is rocky and up-and-down in the beginning. You get a victory, wait for the next thing, keep plowing away. At some point you ask: how can I create a higher floor, a safety net, in the meantime?

He’s got this all-or-nothing narrative in his head—if you take contract work unrelated to the main thing just to stay stable, that’s somehow a failure. Where does that come from? Not very useful. Time to retire that one. So he’s looking at options to bring in a little guaranteed money each month without constant pitching, and let the foundation ferment and grow. They’re in a garden—seeds planted, tending them, there are seasons, and he can see signs of huge opportunity. But it’s not a straight upward trajectory. How do you handle it when the trend line dips before the market kicks back up? That’s the cycle. So he’s shoring up the foundation so arresting fear doesn’t hit every time there’s a lull between where he’s at and the next wave of clients. The question: What do you need to do to make sure the floor is solid and high enough that you’re not going to drown? It’s okay to do it.

Eighty-nine degrees in NYC today (66 days until summer but it already feels like it’s here), and Matt’s looking forward to almost 90-degree weather for now. After sharing trivia about Isaac Newton being knighted (1705), a magnitude 7.0 earthquake in Eureka (1899), and Annie Oakley hitting 100 clay targets in a row (1922), he dives into yesterday’s exhaustion—the kind he didn’t fully appreciate until he was mentally struggling through the day, running errands, driving, head to toe inside and out just spent from the day before.

Then a loyal listener and longtime friend called in the afternoon. She listens to the show most days. He answered the phone, started telling her what’s going on, and she said, “Yeah, yeah, I listened to your episode. I’m caught up.” He just laughed. But here’s the power: having people who really see you, appreciate what you’re going through, know the struggle, and can reflect back what they see. She watched a presentation he did last year that he can’t bring himself to watch—he was in such a bad state about his prior business, realizing he needed to launch The Bigger Stage but hadn’t yet. She said if someone didn’t know him, they’d think it was a great presentation. Knowing him and having seen him operate on different stages, she could tell it wasn’t his absolute knock-it-out-of-the-park performance from his point of view—but it was still great.

That reminder: we need people who can reflect back from a place of love and support. Not everyone stays in your life—sometimes it’s your choice, sometimes it’s not, and letting go is painful. But it culls down to an inner circle of people who really root for you, where there’s mutual support. That core group is absolutely critical. Caring and feeding those relationships, checking in, keeping them close—especially on days when you’re exhausted in every way and need to plug into a power source in somebody else. Isolation doesn’t work. The question: Who’s in your inner circle, and how are you caring for those relationships?

Happy tax day in America, 86 degrees in northern New Jersey, and Matt’s exhausted but inspired after standing up the new website for thebiggerstage.com yesterday. After sharing trivia about the American School for the Deaf (1817), the last day U.S. silver coins circulated in Canada (1870), and the Titanic actually sinking in the early morning hours of this day (1912), he dives into what happened in that marathon workday.

The difference between the first site and this one is significant—it has the benefit of input from a bunch of different people. Yesterday he worked with Mike Verret, who runs a program for developing your perfect pitch, and they got deep into the messaging, the words, the imagery, the story of The Bigger Stage. Here’s what hit him: the first thing you need to do is make people interested. If they’re not, they’ll never walk in the door. You need the hook, then the short story behind the hook that draws them into dialogue about who you’re working with, what problems you’re solving, why it’s relevant.

With The Bigger Stage, people can imagine a stage—a flat wooden structure, lights, curtains. Those are props in the story, literally and figuratively. The challenge is building that world without being too cute or mixing metaphors. Define your terms. Set the stage. Who’s on it? Who’s in the rafters working the lights? Who’s backstage? And here’s the magic: when he’d explain something with a metaphor, Mike would translate it back into stage talk—”yes, that’s exactly right.” Two people can build a world so much faster than one because of the feedback loop. In one hour yesterday morning, they stood up a world. The pieces were already there, but they rearranged them so it looks like a stage. You know where the microphone is. The question for future clients: Are you still backstage fiddling with the sound system, or is it time to step onto the stage and speak to the crowd?

Exhausted but inspired, the messaging foundation is down. Now it’s next level, next level, next level. The question for you: What world are you trying to create? How will you project it out? What’s the metaphor that works, and what can you create today that makes that world even more real when you meet people?