Backstage w/ Matt Stone

Matt Stone Enterprises
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A backstage pass to The Bigger Stage, where host Matt Stone covers the behind-the-scenes lowdown on his journey to build The Bigger Stage brand, business, and show, and the business and life lessons he's learning along the way. mattstone.substack.com

  1. 2h ago

    Trophies and the Troll

    A new Boston Consulting Group study, reported by Fortune, found that only 40% of former CEOs of billion-dollar companies felt satisfied with their transition out of the role in the first year — and the biggest struggle wasn’t money or boredom. It was identity and relevance. Who am I when the title’s gone? Matt’s quick to say no one’s shedding tears for retiring CEOs, but he’s talking about it because he keeps meeting a version of this person who isn’t a retiree at all: the accomplished, seasoned corporate professional — sometimes former C-suite — who’s gone out on their own as a consultant and hit the same wall. They were great inside a company, where the work came to them, the title conferred standing, and the feedback loop told them they mattered. Out in the wild, those signals vanish, and rebuilding a sense of self without them is, in Matt’s long experience doing exactly this, no joke and no overnight fix. Then he offers the image that gives the episode its teeth. We all carry a troll — some core insecurity — and when you’re winning, you can line up trophies in front of it (the title, the pay, the status) and keep it quiet. Go out on your own, and suddenly the trophies are gone and the troll is getting fed, eating protein, building muscle, feasting while you stand there unsure how to project yourself. Matt’s message to anyone in that place: you’re not alone, it’s completely normal, and the way through is a self-awareness journey paired with a healthy dose of self-acceptance — because you may discover your old identity was quietly propping up an insecurity you never had to face. It’s work you generally can’t do alone, since you can’t see yourself. He gets a little raw at the end, invoking the moment in Lawrence of Arabia where you scream “I’m not an animal” — because sometimes you have to strip away the whole facade to reach the marrow of who you actually are, and from there you can finally grow. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com

    Trophies and the Troll

  2. 1d ago

    The Clear Ask

    Matt found a story in the AP that ties together nearly everything this show has been circling. Marisa Mender-Franklin was a teacher during the pandemic who dreamed of growing her own wedding flowers but owned no land. So she posted a single, specific ask to her local Facebook Buy Nothing group: she wanted a place to grow flowers. Her phone started pinging within minutes, and within a week she had roughly 40 offers of free space. Members began dropping cardboard and vases on her porch and volunteering to weed and plant. Today she runs Midtown Bramble & Bloom, oversees nine farm plots, employs ten people, and last year did 57 workshops and 44 weddings — built on the generosity of neighbors who wanted in on the dream. The line from her that stopped Matt: people like to help make dreams come true, and being part of an equal community means you also have to be willing to ask for help. That reciprocity is the part most of us miss. Matt pairs it with an anecdote a past podcast guest once shared — she’d worked for Amazon in France, assumed they’d have to pay small shop owners to host package pickups, and was told to flip it: the pickups would drive foot traffic, so the shops might gladly do it for free, even pay for it. Sometimes, asking for help is itself the gift. So Matt lands on two lessons. Make your asks genuinely specific — the sharper the ask, the more likely someone steps up. And stay open to the possibility that your request is a gift to the person granting it, because there’s real value you may be leaving on the table by only thinking about what you need instead of what they might need too. His prompt: what clear, win-win ask could you make in a community you belong to this week? Make it, and report back. Article link: https://apnews.com/article/flower-farms-sharing-gardens-buy-nothing-bartering-bc4c729304b053b21cf9b429045ddb12 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com

    The Clear Ask

  3. 2d ago

    Become the Center of Gravity

    Fresh from a doctor’s appointment and back on the mic, Matt reinforces the throughline he keeps landing on: building a business in 2026 is about community and events. His evidence is a Verge interview with Ben Smith, editor-in-chief of the news outlet Semafor, which has turned profitable in just a few years by doing what Smith calls an “anti-scale” business. Instead of the old maximum-traffic playbook, Semafor makes roughly half its revenue from convening — real-life events — and deliberately targets a specific, valuable audience of decision-makers rather than the largest possible crowd. The thesis Matt takes from it: it’s not about a million followers, it’s about a thousand people who matter to your business, understand why you matter, and are genuinely dedicated to you. From there Matt makes it personal and practical, drawing on more than thirty years in business development across everything from cold-calling to closing multi-million-dollar deals. Unless you’re selling a low-dollar commodity where price wins, you’re better off building a smaller, concentrated community and giving them things to do, places to go, people to meet. The goal is to become the center of gravity — the nucleus everyone interested in your topic orbits, the person they go to for information or an introduction, the one who’s there through thick and thin and refers people without being asked. That’s why “personal brand” feels too shallow to Matt; it’s not a brand you’re building, it’s a gravitational pull. And here’s the reframe that reorders everything: the content itself isn’t the pull. The environment is. The same post you’d have made six months ago performs better once there’s a gravitational field of real people around you talking about your work and sharing it. His prompt for the week: what’s the number one kind of value you can bring to your people with no sales motive, just service — because in that seed is a whole garden. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com

    Become the Center of Gravity

  4. 3d ago

    The Joy Compass

    Matt kicks off the week with joy on his mind — no articles, no data, just one tool worth stealing. He’s three weeks into a book club run by his friend and colleague Shannon Hernandez around her workbook Practical Joy: Simple Tools to Cultivate More Joy Every Day, and last week’s exercise stuck with him. It starts from a feeling most builders know: waking up and wondering how you ended up doing so much you don’t enjoy, your schedule packed with meetings at the wrong times, pedaling hard and quietly asking whether it’s worth it. Even a little off-track, Matt notes, carries a high cost — and there’s no perfect fix, but there is a way to see the drift clearly. That’s the joy compass. Put a value that brings you real joy in the center — for Matt, it’s deep human connection — then draw the four directions. North is time: how does this value shape how you spend your hours? East is work: how do you want it to shape what you create, offer, sell, and how you operate? South is relationships: how does it shape the way you connect, collaborate, and ask for support? West is body and energy: how does it shape the way you care for your nervous system, your rest, your movement? Filling it out, Matt found himself reconsidering which meetings he takes and whether they should be in person, caught a blind spot (an auto-joining meeting recorder that quietly worked against connection with someone who wasn’t expecting it), and got the nudge to restart the Central Park walks that let him move and connect at once. Some of it revealed gaps; some of it simply validated what he already does for joy and reminded him to schedule the next one. His invitation: draw your own compass, find where you feel integrated with your value and where there’s a gap — because closing that gap is where a little more joy is hiding. More about Shannon here: https://joyfulbusinessrevolution.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com

    The Joy Compass

  5. 5d ago

    The Cake Is Already Baked

    A Fortune piece stopped Matt this week: only 12% of family businesses stay in the family by the third generation. The Goldman Sachs chairman quoted in it argues the culprit usually isn’t a missing legal document — it’s optimism, founders who keep deferring the hard conversations about who leads, what control actually means, and what the next generation truly wants, until entitlement and assumption harden into a problem no contract can fix. Matt knows this one from the inside. In his past life helping teams navigate difficult conversations, he was once a finalist to come into a Midwest family manufacturer wrestling with a bitter succession handoff between two branches of the family. He could see it at the bidding stage: they were far too late. The cake was already baked. So he pushes the lesson way upstream, to founders in growth mode who can’t yet imagine an exit. Plan for succession from day one — and he means it broadly: selling, handing off, or something else entirely. The tool that makes it possible is the thing he’s been circling all along: your story and your meaning, developed early and harvested fully. Why did you start this? What’s the meaning underneath the business? The products and services will change; the underlying why, if you hold to it, won’t. That meaning becomes the foundation of your brand, reputation, and culture — it raises up the people who vibe with it and naturally repels those who don’t, which is exactly what you need aligned over the years and especially at the moment you hand it off. His question for the weekend: have you fully uncovered and written down the meaning behind your business — your North Star, your compass — clearly enough that if you passed it to someone tomorrow, you’d know whether they were in alignment with it? (He also teases what’s ahead: a new offering, fall and December events, a possible live podcast, and a roundtable episode with PR and marketing partners — insiders first.) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com

    The Cake Is Already Baked

  6. Aug 13

    What's Your Repeatable Format?

    Alex Cooper’s media company Unwell just took its first outside investment at a $500 million valuation, on its way, Matt suspects, to making her a billionaire. It started as one person (with a co-host) talking candidly into a mic and grew into a podcast network, live events, streaming projects, consumer products, and a creative agency. Matt’s quick to say this isn’t the path most of us are on, and he sets the controversy aside to get at the business lesson — because there’s one underneath the empire that’s genuinely transferable, no matter your scale. The lesson: find your repeatable format and commit to it. Cooper found a medium that let her show up over and over, hone her craft, and build an audience until she knew exactly who she served — and then she drilled in. That’s the move. What’s the format that lets a bit of your personality out, tells people where to find you in a chaotic feed, and lets you keep practicing? A newsletter isn’t one thing; it’s a blank palette for your unique expression. Same for a podcast, video, or audio-only. The magic isn’t the medium, it’s the repetition — Call Her Daddy has run many hundreds of episodes, and that consistency is what compounds. Matt reframes the goal, too: you don’t need Cooper’s millions, you need your first couple hundred true fans. Do it right and your audience becomes a market that becomes a community, and the overlap of those two is where the signal gets strong enough to tell you what to build next. It scales however you want — a media empire, or a two-person consultancy doing $3 million a year. The question is the same either way: what’s the repeatable format you’ll keep coming back to, fall on your face on, and show up for until the inflection point arrives? (Matt’s own answer is this show — still hovering around 50 Substack subscribers, and honest that losing even one stings, but growing across every platform, and he’s grateful you’re part of it.) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com

    What's Your Repeatable Format?

  7. Aug 12

    A Stage With No Rules

    Matt traces his relationship with media back to its root. As a kid he turned everything into a microphone, pretending to be a talk show host; in junior high he and his friend David recorded fake radio shows on a brick of a tape recorder, complete with invented commercial breaks. That thread runs straight through to his first podcast, Connections That Matter, where every guest told him some version of “I learned so much about myself through this,” and onward to the solo-mic format he’s speaking into now. The point isn’t nostalgia. It’s that there are countless kinds of stages, and he’s spent his life getting to know the medium well enough to know that. Which sets up the reframe: growth for growth’s sake isn’t the point. A hundred people who are genuinely all in on you beats ten thousand who clicked subscribe and forgot — the TikTok sugar high gives broad, fleeting exposure without the long-term satiation, like a bad diet. So Matt has changed how he works: the first three months with a client now go to three questions — what are your real objectives, what’s your core story (backstory, origin, the story now), and what do the stages that actually make you happy look like? Because a stage doesn’t have to be a Tony-Robbins stadium with twenty thousand people walking on fire. It can be twelve people in a circle, an improv session that spills into Central Park, an outdoor adventure, a curated room in your own town, or a special online space you build from scratch. If the one you want doesn’t exist where you are, that’s not a dead end — it’s your opening to build it. He extends the same invitation to founders and CEOs: in a low-trust world, people crave real engagement and access, so what stage could you create where your clients, employees, and stakeholders actually feel seen? The closing prompt: if you had no rules, what would your stage look like? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com

    A Stage With No Rules

  8. Aug 11

    Which Lane Are You In?

    Matt spots a tell in a Digiday headline: Zoom is leaning on creators to boost its AI search results. Zoom is Kleenex for video meetings, but it wants to be seen as a full end-to-end AI platform — and paid ads alone won’t rewrite that reputation. So it partnered with journalist-podcaster Nayeema Raza (30,000+ followers, a sponsored six-part series, a fall keynote at its conference) as a bet on authority and credibility, the very things AI chatbots weigh when deciding what to surface. In plain terms: it’s the new SEO. You used to pay Google to show up for keywords. Now the more third parties talk about you, the more likely a ChatGPT or Claude answer includes you. Zoom itself frames the strategy as earning a place inside conversations it doesn’t own. Here’s why it matters for anyone building a stage. When you post, you think you’re talking to your future client — but you’re actually feeding multiple constituencies at once, and one of them is now the AI systems assembling answers about your field. That’s the source of a tension Matt names precisely: if putting out content feels like mental jujitsu, it’s often because you’re instinctively trying to play several games at once, which is very hard to do well. His resolution is to choose your lane. Are you the creator building an audience you’ll monetize in multiple ways — consulting, services, collaborations, the real money that sits well beyond ad revenue? Or are you the company that needs to find and hire those trusted voices so you show up in more conversations? He points to the broader shift as proof: even in the speaking world, the data shows companies increasingly want a consultant who speaks — someone with follow-on services — over a speaker who just leaves behind a book, and a motorsport platform called Driven building community and personalities instead of leaning on algorithmic distribution. Everyone’s chasing the same thing in the attention economy: a real relationship with their people. Know which side you’re on, then build accordingly. Articles cited: https://digiday.com/marketing/zoom-relies-on-creators-to-boost-ai-search-results/ https://www.sbnation.com/formula-one/1124318/driven-jenson-button-ben-collins-f1 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit mattstone.substack.com

    Which Lane Are You In?
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About

A backstage pass to The Bigger Stage, where host Matt Stone covers the behind-the-scenes lowdown on his journey to build The Bigger Stage brand, business, and show, and the business and life lessons he's learning along the way. mattstone.substack.com

Information

  • Creator
    Matt Stone Enterprises
  • Years Active
    2020 - 2026
  • Episodes
    295
  • Rating
    Explicit
  • Copyright
    © Matt Stone Enterprises, LLC
  • Show Website
    Backstage w/ Matt Stone