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Subtitle: Matt resets Backstage around its real purpose — and shares the storytelling shift that made a bored panel remember him for the rest of the day
Description:
Backstage is changing, and Matt’s being upfront about why: he changed the name before he changed the show, and now it’s time for the style to catch up. Going forward this is a sharper daily dose for founders, entrepreneurs, and leaders who’ve realized their personal stories are a real business advantage — with a warm nod to the legacy audience of friends and family who’ve been here since it was a personal journal. Then he gets to the actual lesson: how to tell a short story that lands.
The proof is a panel he sat on years ago, bored stiff by a by-the-numbers format, who decided to answer his question with a story instead of a list — and watched the whole room wake up. People brought it up in follow-up meetings for the rest of the day; the story traveled beyond him. Matt’s point is that storytelling is a muscle, not a gift: it takes practice to keep stories accessible and to drop into that mode with energy, clarity, and presence. A practical, slightly reflective one on why “you know what that reminds me of…” beats “trend number one is…” every time — and a closing challenge to notice what makes you pay attention to someone else today.
The CN Tower turns 50 today — it opened to the public on June 26, 1976 — and Matt can’t stop thinking about what makes a tower iconic: the way one structure becomes shorthand for an entire city, from Toronto to Seattle’s Space Needle to the Eiffel Tower in Paris. It’s his new metaphor for the operator-to-icon journey. Becoming an icon means raising a tower rooted deep in your base — your brand, your story, your personality — that throws a beacon far past it. The catch is that towers take a long time to go up, and the base has to be ruthlessly focused before the signal can travel.
Which leads to a candid reflection: Matt’s own tower is still under construction. He’s wrestling with a real tension in who he serves — the established, hypergrowth founders he’s built around versus the people in transition whose stories tug at his heart — and why focus, not breadth, is what finally gets a structure off the ground. Along the way: a warm recap of his first “DiNNr” (six people, two and a half hours, the real stories behind the polished exteriors), a quick lap through this day in history, and a Substack milestone coming into view. A reflective Friday send-off to close: who will you connect with this weekend, and what will you do to take care of yourself?
In 1886, a teenage cellist touring Brazil was pushed onto a podium nobody else could hold: a hostile crowd, a walked-out conductor, and a full performance of Aida with no rehearsal. He led the whole thing from memory. His name was Arturo Toscanini, and that accidental night, which the history books place somewhere in late June, launched one of the longest, greatest conducting careers ever. Matt’s takeaway is the part worth sitting with: the conductor was already inside the cellist. The skill drew from the same source; it just hadn’t found its form yet.
It’s a story for anyone building something: the plumber, the programmer, the operator who became a founder and discovered the role asks for more than the craft that started it. But Matt’s real point is readiness. You can’t know which moment is yours, so you prepare, stay curious, and keep your heart open to good risk. Along the way: the deliberate next layer of his YouTube strategy taking shape this summer, a two-hour sales webinar that turned into a masterclass in how not to sell (shame and pressure guarantee the opposite of a sale), and a peek at tonight’s intimate storytelling dinner in SoHo. An energizing one — with a question to carry: what’s the moment you’re quietly getting ready for?
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A small note from the cutting room: Toscanini's accidental debut is pinned by historians to two competing dates — June 25 and June 30, 1886 — so the exact day is debated rather than settled. Either way, the story holds.
Matt’s long-form founder interviews have always been the aspirational top of the Bigger Stage — proof of what’s possible after years of building something real. Now he’s adding the layer he’d always planned to: a sharper, more useful YouTube track aimed upstream, helping experienced professionals launch themselves as their own company and sell their story, their why, to win clients on their own terms. Same channel, same mission, deeper reach. The refinement (insiders hear it first) extends the strategy rather than replacing it — meet people where they’re searching for answers, and the path to working with founder-CEOs opens up naturally downstream.
Underneath the platform tactics is the principle that’s been guiding the whole build: what you do is fungible, but why you do it isn’t. The meaning beneath the work is what survives layoffs, lost titles, and the day an “orange meteor” comes for your business — and it’s the thread that lets one channel serve very different audiences at once. There’s also a summer weather check, a very honest gripe about World Cup traffic through the Lincoln Tunnel, and a candid note on staying disciplined when results lag behind the effort. A focused one for anyone refining what they’re already building.
On June 23, 1868, the first typewriter patent was granted — but the machine that eventually put QWERTY in everyone’s hands almost didn’t get made at scale. The company that pulled it off wasn’t a printer or a publisher. It was a firearms manufacturer in trouble. Matt digs into how Remington, struggling after the Civil War dried up its business, reinvented itself around the typewriter, and why the least obvious partner turned out to be the perfect one.
That history opens up a sharper question for anyone building something: most of us go looking for partners who can send us business. Matt makes the case that this is exactly the trap. The better lens is asking who’s remaking themselves right now — and where their reinvention happens to overlap with what you do. (Case in point: the viral shoe brand that just rebranded itself into an AI company.) It’s a short, practical reframe on why the best partnerships start with intention rather than extraction.
It’s Monday, June 22nd — 92 days to fall, the World Cup is quietly turning NYC and Northern NJ into a parking lot, and Matt is back behind the mic with a confession: summer is a recession. Not the scary kind — the calendar kind. Fewer appointments, more out-of-offices, the slow exhale most businesses feel once the kids are out of school. And the smartest move in a recession, as a fellow named Franklin Delano Roosevelt understood when he signed the GI Bill in 1944, is to invest. Matt threads together that bill, a muttering Galileo, and the quiet art of planting now so you can harvest later.
From there it gets personal. Matt digs into why growth always starts with letting go — even when the thing you’re letting go of is your baby — why process beats results on the days you’ve completely lost the plot, and what he’s putting in the ground this season, from a health reset to a reading stack with some uncomfortable parallels to right now. Oh, and one more thing: the daily journal is officially back. So what are you going to take a shot at today?
On this June 12th edition of Backstage Friday, Matt checks in from a week of genuine momentum: the Untold Stories Tour is taking shape with a Denver venue locked in, a new Manhattan networking group that feels more like family than business cards, and a client breakthrough that reminded him just how much a great interview can unlock.
But the heart of this episode is a reading from David Kalinowski’s The Sacrifice Paradox — specifically Story 78, “The Entrepreneur’s Loss.” It’s a short, punchy parable about a founder who bet everything, lost it, and came out the other side with something more valuable than what he gave up. Matt closes with the question the chapter poses — and makes it personal. What would you truly risk to build something you believe in?
Matt bought bananas this morning, which got him thinking about 1876. But that’s just the warm-up. This week on Backstage Friday, Matt pulls back the curtain on one of the most consistent patterns he’s seeing with clients: the gap between AI-generated messaging and the real thing — and why the difference is less about the tool and more about what you feed it. Spoiler: deep broth beats instant every time.
Plus, The Bigger Stage is hitting the road. Denver may be the first stop in a new on-location series, and Matt’s scheming a New York City show with a former chef-turned-real-estate-broker who knows where all the colorful skeletons are buried. The theme tying it all together? Stop waiting for the giant leap. Just keep leaping.
Where in your life could slow, steady, relentless progress actually be the move?
Matt’s been sitting on something — and this episode is where it comes out. A new offer, a handful of cities, and a concept called Untold Stories: the next evolution of The Bigger Stage is starting to take shape, and listeners are getting the first look before anyone else. In this week’s Backstage, Matt also gets into why writing a single LinkedIn post by hand felt like going to the gym, what a Shannon interview on founder identity uncovered about AI and authentic voice, and what reconnecting with a law professor after 23 years reminded him about the staying power of real relationships.
Blue laws, rice cookers, and Rhode Island’s very late arrival to the Constitution also make an appearance. Because of course they do.
It’s been a week — the kind that’s equal parts exhausting and exhilarating — and Matt is back Backstage to fill you in. He digs into a paradigm shift around LinkedIn and social media (turns out treating the feed like a room full of people beats posting and running), teases a Hollywood project bridging entertainment, business, and leadership development, and reflects on why holding up a mirror to show people how great they already are sits at the heart of The Bigger Stage.
Then there’s the trivia that lands the plane: on this day in 1843, a wagon train of 100-plus left Missouri for Oregon. Most of the people made it. Their wagons mostly didn’t. Matt unpacks what that says about the vehicles we ride into our ambitions — franchises, old habits, comfortable assumptions — and why the thing that carries you part of the way isn’t always the thing that gets you home. What got you here, as the saying goes, won’t get you there.
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