Backstage w/ Matt Stone

Matt Stone Enterprises
  • 5.0 (7)
  • Entrepreneurship
  • Updated Daily

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. 3d ago

    Don’t Sleep on the Boomers

    Matt closes the week on a Business Insider piece with a counterintuitive lesson. Research from Morning Consult (run for Business Insider) and Edelman shows a big generational split on influencers: only about 31% of boomers trust influencer recommendations, versus roughly 62% of Gen Z and 64% of millennials, and only about a quarter of boomers follow content creators at all, compared to the vast majority of younger people. Boomers are also more likely to say they trust influencers less than they used to, have never bought anything on a recommendation, and find the content annoying. Matt, a self-described forgotten Gen Xer, can relate, though the lawyer in him wants to pin down what we even mean by “influencer.” He means the professional kind, the person whose whole business is taking pictures of themselves and building a following to tell you what to buy (think the LinkedIn influencer whose entire business is teaching you how to make money on LinkedIn, a bit of a closed loop). Here’s why the “problem” is actually an opportunity. Boomers account for about 42% of spending among affluent US households (Visa), yet marketers pour tens of billions into creator partnerships aimed at much younger audiences. Some agencies even report stronger conversion from older, more experienced creators, while brands stay reluctant to use them. So two takeaways. First, don’t sleep on the boomers, depending on your business, there’s a whole market of healthy, financially capable people, often on their second or third career and moving to the next thing, that service businesses ignore at their own expense. Second, invest in real relationships. Matt’s clients range from Gen Z to boomers, and his advice is the same to all of them: don’t judge yourself against social media influencers. Your opportunity is to build trust the slower way, show up in person and online, do the one-on-ones, sow into the soil and fertilize it for real, and build a loyal community. With so much nonsense flooding social media, the differentiator is simple: don’t be nonsense. His questions for the weekend: who do you actually follow, does the word “influencer” even matter to you, and what’s your honest relationship with all 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

    Don’t Sleep on the Boomers

  2. 4d ago

    Into the Ditch

    No articles today. Matt’s still turning over the Your New Opening Line pilot in Denver, a small but mighty room of people each refining the opening to a talk, and he pulls out three lessons (plus a bonus). First, going blank. When you’re performing to a camera or working a talk, the harder you push, the more you get in your head, and it feels like driving straight into a ditch over and over. Get back in the car, start the engine, aim down the road, and it’s in the ditch again. Grinding the same way never works. You have to break the pattern: throwaway rounds, a joke from the person behind the camera, walking away, goofing around, anything that takes the pressure of performance off. One participant came out of the gate strong, then got in her head, and what finally worked wasn’t pushing through it directly, it was disengaging and re-entering later. Instead of driving, fly. Instead of driving, skip rope. Second, you can’t see your own diamond. It’s easy to spot the story that shines in someone else, the one that explains everything about them, and almost impossible to see it in yourself. The things most central to our own story are the ones we take for granted or never bring up, especially when telling them feels promotional or like cheapening them. It takes other people in the room saying no, no, tell that story again, that thing about your father is the gold, not what you were focusing on. That happened over and over in the session. Third, how you think beats what you think. The way you came to an idea, what informed it, is more useful to other people than the conclusion itself. Matt’s version: how you came to know and believe something is more interesting than what you know and believe. It’s why “most people think X, but here’s the truth” posts fall flat, and why human narrative is so powerful, because even if someone disagrees with your conclusion, they can have mad respect for how you got there. The bonus thought: this format would be a phenomenal, indirect team-building experience for leadership teams, because engaging with each other’s stories builds trust and familiarity fast. His questions: what’s a throwaway fact in your story that others found fascinating, and what are you working on that would benefit from a group for a while? Nobody sees their own blind spots alone. 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

    Into the Ditch

  3. 5d ago

    From Discovery to Retention

    Matt opens with a reflection from the Denver pilot of Your New Opening Line: the blank. When you’re working on a talk, you hit a point a few rounds in where it stops feeling fun and you start fighting it, right before it becomes fully integrated inside you. One participant lived it in real time. The fix isn’t to grind harder, it’s to break it up, let go, tell your mind you’re done with it for a moment. Same trick works on camera, “this isn’t the real take, I’m just going to riff,” and then you nail it. Totally normal, part of the process, and you keep going until you get free and easy with it. Then the signal, and it rhymes. A Digiday piece reports that The Verge has rebuilt its audience team for “Google Zero,” the post-search era where Google referral traffic dries up. For years publishers chased search optimization, social distribution, and raw traffic. Now The Verge organizes around three audience groups, anonymous visitors, registered users, and paying subscribers, and specialists in newsletters, community, and analytics, with each person carrying a growth target instead of a page-view number. The whole aim shifts from discovery to retention: turning occasional visitors into people who intentionally return. Tellingly, more than half of their subscriber sign-ups now come from readers going directly to the subscription page, a deliberate decision to buy, not an incidental one while reading an article. That’s the difference from the old model, Matt notes, where you put bait on the hook (a blog, a PDF) to capture an email. This is building a relationship first, so that when someone’s ready, they come find the sign-up page themselves. He maps it straight onto building a business with media: yes, you want attention and short-form discovery, but never at the expense of giving people reasons to come back, things to do, multi-phase offerings, exclusivity. He points to his own show’s regulars, the ones who comment and quote it back to him, as the equivalent of paying subscribers, client or not. His question: what’s the one thing you could offer on an ongoing basis, exclusive to people who join at a deeper level, that pulls them into your fold? 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

    From Discovery to Retention

  4. 6d ago

    Not a Content Studio

    Fresh off a trip to Denver, Matt opens on a Guardian story: a growing list of hotels, restaurants, and beauty spots are restricting photography and filming, not just because creators are there, but because content production wrecks the experience for everyone else. The Hôtel du Cap-Eden-Roc now requires permission for photo shoots after guests booked meals mainly to stage elaborate multi-outfit sessions. A Cheshire farm shop, The Hollies, banned filming during its busiest hours after going viral. As Beaumier’s marketing chief puts it, hospitality exists to provide memorable experiences, not to serve as content-production locations. Matt knows the feeling, he treats his gym as a refuge, and a space that feels like a production studio is genuinely irritating. Businesses are caught between a rock and a hard place: social media is great publicity, but you can’t let it ruin the room. Then the report back, and the real point. At the Denver pilot of Your New Opening Line with Mark DeCarlo, they recorded each participant’s three rounds primarily for the participants, as a feedback loop to see their progress, and had someone capturing selective footage for future promotion. But Matt was deliberate about not letting the filming interfere with the intention of the experience. His stance, against the marketing chorus of “always be creating content,” is that he just doesn’t agree. The mindset you’re in when you’re creating content destroys the integrity of your intention, because you can’t be truly present with someone while thinking about how it’ll look on TikTok. He points at the Kardashians as the tell: those shows have filming schedules and designed controversies, a facsimile of reality, and being on camera all the time (especially for kids on reality shows) isn’t healthy. So in Denver, he and Mark stayed 100% zeroed in on serving the participants, asked the videographer to grab just a taste rather than everything, and the only thing Matt tracked about the camera was getting out of its way. Yes, we need good content, he’s making it right now, but it has to be thoughtful and well-placed, not grist for the mill. Creating experiences is a different form of creation than creating content, and filming everything is not how you get the best result. His takeaway for anyone anxious about always posting: spend the majority of your time truly present, then figure out how to make content that matters. 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

    Not a Content Studio

  5. Oct 13

    The Third Audience

    [Note: This is the last Backstage episode this week. Back at it Monday, October 19th.] Matt opens on a fresh Axios piece from co-founder Jim VandeHei that names a real shift: business communication now has a third audience. For years executives communicated to two, the internal team and the external world of customers, investors, and the public. Now AI is a distinct third audience, because people increasingly discover companies, products, and experts through AI-generated answers rather than search, and agents are starting to research and decide on people’s behalf. VandeHei’s fix starts with clarity: consistent language on what matters, why it matters, and what evidence backs it up (Axios does it with its Smart Brevity structure). Matt’s addition is the tension underneath. Humans respond to personality, story, and emotional resonance. AI systems want accessible, structured, consistent information. There’s overlap, but they’re not the same, and he’s honest that an obviously AI-written one-to-one email is a turnoff, because it leaves you less connected to the person who sent it. That leads to the heart of it, a defense of human messiness. We play in the mud. We stumble, repeat ourselves, search for the word, and that imperfection is itself a signal that we’re working things out in real time, so natural that listeners fill in the word right alongside us. The danger isn’t using AI, Matt uses it like everyone, it’s letting the structured, machine-readable version drown out the searching, stumbling, unfiltered human process. His bet is that demand for unassisted human communication only goes up as AI does more of the analysis, because living in a bot-driven comms world simply isn’t satisfying. Sitting at a cafe with a friend, communication unaided by anything but a cappuccino, now feels like a beautiful indulgence, and he thinks that feeling has merit and whole businesses will be built around it. His own answer to doing both at once is the interview: being interviewed by a high-EQ person who senses where you are emotionally and pulls the thread instead of marching down a question list. It captures compelling human narrative and documents your professional identity in a form AI will recognize, and it’s why long form still resonates even in the short-attention era. His question: what’s the most meaningful thing you do that’s completely offline? 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 Third Audience

  6. Oct 12

    Tend Your Wisdom Garden

    Matt opens with apple picking in biblical New York rain (proof you can have a blast even when it’s pouring) and two Business Insider stories that pull in the same direction. First, the power of story. Denise Woodard founded Partake Foods after her daughter’s severe food allergies, selling allergy-friendly cookies out of her car. Her entire early marketing strategy was simple: tell the story of why she started the company, then let people taste the product. That story is what attracted customers and investors, including Jay-Z’s Marcy Venture Partners, which Woodard says was sold not by a plan but by why she was doing it. (She did scale too fast, 300 stores to 5,000 in a year, 10x revenue with infrastructure that couldn’t keep up, which nearly killed the business, but Matt’s point is she never gets near that problem without the story that got her off the ground.) The lesson he keeps hammering: when you’re small, a powerful story lets you punch way above your weight, because people invest in you, not the plan. The plan will change. They’re betting on whether you can grow, learn, and adapt. The second story is Bird CEO Robert Vis, who cut his workforce from over 1,000 to 120 and says AI is making high-agency generalists more valuable, people who grasp the larger objective, exercise judgment, and own the result rather than just executing tasks. Matt agrees generalists are valuable (as a Gen X generalist with a law degree, sales, and even trades skills behind him, he counts himself one). His worry is upstream: judgment and generalist wisdom require real experience and a feedback loop, time in the trenches, learning by doing. Between social media and AI doing the work for people, he’s not sure we’ll grow enough people with enough genuine experience to become those generalists. So he turns fear into opportunity. The move is to deliberately keep yourself in a garden where ideas get exchanged and pressure-tested, book clubs, philosophy clubs, hands-dirty work, places with deep thought and a real feedback loop. He’s got a specific plan to reinvest in that for himself, because it’s easy to lose touch with it on these platforms. His question: how are you tending your wisdom 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

    Tend Your Wisdom Garden

  7. Oct 8

    The Booster Rocket

    Matt opens on a joyful note about his own year with The Bigger Stage, and a useful lesson hiding in it: you can design a narrow ideal client profile, but the reality is usually more diverse, held together by a common thread. For him that thread is helping people understand who they are and express part of it outwardly to differentiate, humanize, and move the hearts and minds that matter to their success, not just clients, but future employees and collaborators too. Then to the signal: a Wired story that the Center for Humane Technology, the online-safety nonprofit co-founded by Tristan Harris of The Social Dilemma, is laying off about half its non-founder staff and ending its policy research and litigation work to go founder-led, leaning on public education, briefings, and Harris’s own public profile. The board says a founder-centered approach is the most effective way to advance the mission. Some former employees worry it’s trading institutional capability for one person’s visibility. Matt’s read, offered as interpretation rather than fact: this looks like an organization recognizing it got ahead of its own economics, that its founder is still its best asset, and that it needs more booster rocket before it can run on built-out infrastructure. That’s the analogy that anchors the episode. A founder is a booster rocket. To get the shuttle into space, you need that heat and fuel burning hot. Flame out too early and you never reach orbit. But keep it up long enough, in the right direction with the right strategy, and eventually the boosters fall away and the thing floats on its own. Every founder-led organization faces the same conundrum: if you walked away for six months, would it keep going? And it’s okay if the answer is no, that’s just a stage. The danger is not knowing which stage you’re in. The work is to use the founder phase to speak the vision into reality, then patiently build the revenue lines, the IP, and the team that don’t depend on you. Matt’s thinking about it for The Bigger Stage himself. His question: are you still in the booster-rocket phase, or have the boosters fallen away? 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 Booster Rocket

  8. Oct 7

    A Relationship Group, Not a Networking Group

    Matt had networking on his mind after another great night with his own group, and a Business Insider story landed right on it. Alena Beliauskaya started inviting startup founders hiking because she loved the outdoors. That turned into 12 Scrappy Founders, a Bay Area community now 600-plus strong, mostly AI founders, generating around $10,000 a month, and she keeps it as a side hustle alongside a full-time job. What’s more interesting than the revenue is the design: no mixers. They hike, camp, dirt bike, play poker, do things together. You get to know someone over eight hours on a trail in a way a name-tag event never delivers. Matt connects it to a Denver group called Accelerent, whose leader gently corrected him when he said “networking group.” No, we’re a relationship group. They do everything a networking group does, just built entirely on intentional, high-end relationship building. His read: a lot of people are done with traditional networking, and there’s real opportunity in giving them a way to come together that’s non-salesy and built around something they actually enjoy. The on-ramp is smaller than people think. Get three people in a room. If each brings three, you’re at twelve, and then it compounds. He runs the economics (a hobby quietly throwing off a few thousand a month, with room to become a full business if she ever wanted it) and frames it the way he frames YouTube: the activity itself can be the product, or it can be how you monetize everything around it. Underneath it is the metaphor he keeps returning to, his Japanese father-in-law’s garden, known across the neighborhood, built from a few plants years ago and fed patiently ever since. That’s how you build community in 2026. The screen is a great bulletin board for staying top of mind, but people want to meet somewhere real. His advice: start in your own local community and dive in. His questions: what’s the best event you’ve been to lately, or the one you wish someone would host? 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 Relationship Group, Not a Networking Group
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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
    330
  • Rating
    Explicit
  • Copyright
    © Matt Stone Enterprises, LLC
  • Show Website
    Backstage w/ Matt Stone