Generator
Generator

Generator

Matt Stagliano

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Join host and Maine portrait photographer Matt Stagliano while he has long, casual conversations with his guests about creativity in photography, art, business, and relationships.

Recent Episodes

077 - Executive (Dis)Function with Sean McCormick
JUN 19, 2026
077 - Executive (Dis)Function with Sean McCormick
Most of us got into creative work wanting to do everything, then spent years drowning in all of it. Sean McCormick did the opposite on purpose.Sean spent years as a public school special education teacher before he walked away from the steady paycheck, with two young daughters at home, to bet on one narrow lane: executive function coaching. He built Executive Function Specialists, founded the Executive Function Coaching Academy to train other coaches, and co-founded a practice for adults. His newsletter reaches about 6,000 people who actually open it.This one runs deep. Matt and Sean trace the whole road: a summer meditating at a remote fishing lodge in the Misty Fjords of Alaska, a failed run as a rapper, a stretch ghostwriting papers he wasn't proud of, and the hard no from his school district that finally told him the system would never bend for the life he wanted.What we get into:- Finding the intersection of what you love, what you're good at, and what people will pay for- Why "think huge, act tiny" beats chasing the big swing- The real reason people never reach their vision, and how task switching drains your resolve- Protecting your floor and actually investing in yourself- Flow state, craft, and what AI can and cannot do for a creator- Getting small on purpose, and why Sean chases depth instead of reach- The status game vs the wealth game- Evicting the critical roommate in your head- Five years sober, service, and not being the center of the universe- His goal of training 10,000 coaches by 2032, and the educator poverty behind it- The two beliefs that changed everythingCHAPTERS00:00 Intro: the guy who got smaller on purpose04:04 Alaska, the lodge, and learning to seek07:40 The breaking point: a hard no in teaching12:04 The kitchen table and the rapper years16:02 Product-market fit and your "bang"21:06 Explore, then exploit: finding your one thing25:35 The exercise: what you love meets what pays29:37 Why people never reach their vision32:51 Protect your floor and invest in yourself36:35 Flow state, craft, and what AI can't do39:53 Getting small: depth over reach44:36 The status game vs the wealth game46:06 What he wants his daughters to absorb50:10 Removing what holds you back53:15 Evicting the roommate in your head55:46 Sobriety, service, and purpose01:00:55 10,000 coaches, ADHD, and educator poverty01:09:25 The two beliefs that changed everything01:16:13 Where to find SeanAbout Sean McCormickSean is a former special education teacher turned executive function coach and founder of the Executive Function Coaching Academy. He helps educators build small businesses that liberate them, and coaches creators and entrepreneurs on focus, self-direction, and purpose.Find SeanExecutive Function Coaching Academy: https://www.executivefunctioncoachingacademy.com/Sean's site: https://seanmccormick.meEmail Sean: [email protected]'s book is free on Audible and YouTube, recorded in his own voice.Generator Live is a show for working creatives who are building something and want to talk about what that actually looks like. No highlight reel. No tactics dressed up as wisdom. Just honest conversation about the doubt, the financial reality, the isolation, and the question every creative eventually asks themselves: is this worth it?Some weeks we talk about the business side of creative work. Some weeks I just think out loud about whatever is on my mind, and you get to be there for it.Come hang in the chat. This is a conversation, not a broadcast.Connect with GeneratorWebsite: https://generatorpodcast.comInstagram / YouTube / Podcast: @generatorpodcastSpeak Less, Get More — My book on interview skills for podcast hosts, built around the PODS Framework.Ebook: https://www.amazon.com/Speak-Less-Get-More-Conversations-ebook/dp/B0GX3CLQX5/Paperback: https://www.amazon.com/Speak-Less-Get-More-Conversations/dp/B0GY2P2GRT/Hardcover: https://www.amazon.com/Speak-Less-Get-More-Conversations/dp/B0GY2Z8GPL/Getting Good at Claude — My setup system that gets Claude working the way you work, so it sounds like you and saves you hours.Get it here: https://payhip.com/b/syOPkTools I Use and RecommendEcamm Live (live streaming and video, Mac only): https://www.ecamm.com/mac/ecammlive/?...Captivate.fm (podcast hosting and distribution): https://www.captivate.fm/signup?ref=y...17Hats (CRM for creative businesses, 50% off first year): https://referrals.17hats.com/card/sto...BorisFX CrumplePop (audio cleanup): https://borisfx.com/?a_aid=68bb347aa27d1WisprFlow (voice dictation): https://wisprflow.ai/r?MATT1716Pixieset (client photo galleries, $20 off): https://pixieset.com/ref/djDARTY4paCloudways (WordPress hosting): https://vrlps.co/f83e6os/cpFourthwall (branded merchandise): https://link.fourthwall.com/join/gene...Full studio and gear list on Amazon: https://www.amazon.com/shop/stonetree...Some links above are affiliate links that may pay me a commission at no cost to you. I only recommend things I actually use.
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81 MIN
076 - Starting Over at 62 with Jörg Kampers
JUN 2, 2026
076 - Starting Over at 62 with Jörg Kampers
"As soon as your age has a six in the front in Germany, it's very difficult to find another corporate job." That's where Jörg Kampers starts his story. He spent 35 years inside companies like Commodore, Dell, and CommScope, selling the Amiga 500 as a physics student in his university days and running PCs, networks, Wi-Fi, and 5G across the decades that followed. Last year the company got sold. At 62, with a pension that wasn't going to cover the way he actually lives, he did the ikigai work and pointed the camera at himself.This conversation stays with the man, the math, and the moves he's actually making. We talk about the 600,000 German Mittelstand companies searching for a successor and the third of them that have already decided to shut down rather than find one, the surprise finding that boomers and late Xers are the fastest-growing creator community on YouTube with Gen Z as their main audience, and what Jörg is building at silverstreamer.live, including the pre-programmed Gemini gems that interview people about their passion and the channel analyzer that gives any creator pro-level feedback. He also brought his wife into the conversation, which turned into the most honest stretch of the hour. She's the one teaching him what it actually takes to teach somebody else.WHAT YOU'LL TAKE AWAYBoomers and late Xers are YouTube's fastest-growing creator community, and Gen Z is the audience watching them, looking for authenticity, experience, and the wisdom of a generation that earned its stories the slow way.600,000 German Mittelstand companies are looking for a successor right now. Roughly a third have already given up and chosen to shut down.Starting over after 60 is a patience problem. The tools are learnable, and the discipline that matters is showing up over and over until it sinks in.AI is a real toolbox for creators. It can interview you about your passion or analyze your channel for pro-level feedback. As Jörg puts it, it still can't change a tire or fix a leaky faucet, which is roughly where the magic stops.The hardest place to teach is at home, and it's also where you learn whether you can actually teach at all.About Jörg Kampers A digital native in the body of a boomer. After 35 years inside companies like Commodore, Dell, and CommScope, he started over at 62 as the Silverstreamer, helping people over 50 step in front of the camera and turn decades of experience into something visible, and sometimes into a whole second career. The Silverstreamer Academy launches in about six months.Find Jörg:YouTube: https://www.youtube.com/@JoergKampersSubstack: https://silverstreamer.substack.comWeb: https://www.silverstreamer.liveFacebook: joergkampersBased in Bad Pyrmont, about an hour from Hannover, GermanyListen & SubscribeNever miss an episode. Subscribe to Generator on your favorite podcast app:Apple Podcasts | Spotify | YouTubeEnjoyed this episode? Leave a 5-star review on Apple Podcasts to help others discover these conversations.Connect with GeneratorWebsite: generatorpodcast.comInstagram: @generatorpodcastTikTok: @generatorpodcastYouTube: @generatorpodcastHost: Matt Stagliano - Stonetree Creative, MaineGenerator is a podcast about the creative process, personal growth, and what it means to build something meaningful. Hosted by portrait photographer Matt Stagliano.Leave a Review: Head over to https://podcasts.apple.com/us/podcast/generator/id1668192673 and leave us a 5 Star review if you liked the show! Help others discover this podcast.Here's what I use to make Generator a reality:SOFTWAREECamm - What I use to live stream, record my video, and conduct interviews (Only for Mac)https://www.ecamm.com/mac/ecammlive/?fp_ref=generatorCaptivate.fm - The software I use to publish every audio episode and distribute it everywherehttps://www.captivate.fm/signup?ref=yjuymdqo17Hats - Get 50% off your first year of the best CRM for entrepreneurshttps://referrals.17hats.com/card/stonetreeBorisFX Crumplepop- Clean up audio faster than ever beforehttps://borisfx.com/?a_aid=68bb347aa27d1Cloudways - Solid, affordable Hosting for my wordpress websiteshttps://vrlps.co/f83e6os/cpPixieset - Get $20 off my favorite way to show clients their gallerieshttps://pixieset.com/ref/djDARTY4paWisprFlow - My typing gets slow, so being able to dictate anything in any app makes Life a lot easier.https://wisprflow.ai/r?MATT1716Fourthwall - A great selection of drop-shipped branded productshttps://link.fourthwall.com/join/generatorHARDWAREMy Entire Studio Setup - This is an ongoing list of all the equipment I use in my home studiohttps://www.amazon.com/shop/stonetreecreative/list/UI27EORM80W1?ref_=cm_sw_r_cp_ud_aipsflist_91ERYXJ9ZAQ1E4C0Q1VTSmall print: Some of these are affiliate links. If you buy through them, I get a small commission at no cost to you. I only recommend stuff I actually use.
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78 MIN
075 - No Admin, Just Shoot with Ashley Siegert
APR 10, 2026
075 - No Admin, Just Shoot with Ashley Siegert
Most photographers will tell you the same thing if you ask them honestly. The shooting is the part they love. Everything else is overhead. Ashley Siegert heard that enough times that she built an entire company around it.Ashley is the founder of Vacanva, a platform that pairs photographers with nonprofits to run portrait-based fundraising campaigns. The model is built so that photographers show up, shoot, and get paid, while Vacanva handles everything else: client consultations, location scouting, permits, editing, gallery delivery, and mileage reimbursement. The nonprofits get an easy fundraising vehicle. The clients get portraits they actually wanted. And the photographers get paid work without the admin weight that burns most of them out.Ashley came up as a producer and stage manager for ESPN baseball, building a portrait business in parallel and running at a pace that would have broken most people. When COVID killed her original tourism concept days before launch in March 2020, she pivoted into nonprofit partnerships with the organizations already in her orbit. The first campaign sold 20 packages. The next sold 30. Vacanva now has 75 photographers and is in conversations with corporate partners that could accelerate the whole thing significantly.I met Ashley at WPPI a few weeks ago and walked away from that first conversation wondering how I had not heard about this sooner. This episode is the answer to that question.What You'll Learn:How a last-minute COVID pivot turned a silent auction donation into a repeatable nonprofit fundraising modelWhat photographers are actually paid and how session assignments workEverything Vacanva handles on the backend so photographers never have toWhat the staff portal provides before you walk into a sessionThe corporate partnership strategy Ashley is building toward and why it mattersWhat is coming this summer and why it is worth watchingResources Mentioned:Vacanva: https://vacanva.comConnect with Ashley Siegert: Vacanva: https://vacanva.comConnect with Matt: Website: https://generatorpodcast.comInstagram: @generatorpodcastWant to be a guest? https://generatorpodcast.com/apply/Here's what I use to make Generator a reality:SOFTWAREECamm - What I use to live stream, record my video, and conduct interviews (Only for Mac)https://www.ecamm.com/mac/ecammlive/?fp_ref=generatorCaptivate.fm - The software I use to publish every audio episode and distribute it everywherehttps://www.captivate.fm/signup?ref=yjuymdqo17Hats - Get 50% off your first year of the best CRM for entrepreneurshttps://referrals.17hats.com/card/stonetreeBorisFX Crumplepop- Clean up audio faster than ever beforehttps://borisfx.com/?a_aid=68bb347aa27d1Cloudways - Solid, affordable Hosting for my wordpress websiteshttps://vrlps.co/f83e6os/cpPixieset - Get $20 off my favorite way to show clients their gallerieshttps://pixieset.com/ref/djDARTY4paWisprFlow - My typing gets slow, so being able to dictate anything in any app makes Life a lot easier.https://wisprflow.ai/r?MATT1716Fourthwall - A great selection of drop-shipped branded productshttps://link.fourthwall.com/join/generatorHARDWAREMy Entire Studio Setup - This is an ongoing list of all the equipment I use in my home studiohttps://www.amazon.com/shop/stonetreecreative/list/UI27EORM80W1?ref_=cm_sw_r_cp_ud_aipsflist_91ERYXJ9ZAQ1E4C0Q1VTSmall print: Some of these are affiliate links. If you buy through them, I get a small commission at no cost to you. I only recommend stuff I actually use.
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80 MIN
074 - Stop Chasing Maybe Money with Billy Thorpe
APR 3, 2026
074 - Stop Chasing Maybe Money with Billy Thorpe
I met Billy Thorpe on a bus. We were heading to the venue for Ecamm Creator Camp last October, he sat down in front of me, we started talking, and somewhere in that conversation he casually mentioned that he makes product videos on Amazon and that brands pay him to do it. I pulled out my notepad and started taking notes before he finished the sentence.Billy is one of those people who has built something genuinely useful and refuses to make you pay to find out how he did it. He's been averaging over 100 videos a month for the better part of four years, has cultivated real brand partnerships with smaller businesses rather than chasing household names, and is about as honest about his failures as anyone I've had on this show. He dropped out of high school. He has ADHD. He ran an airsoft field, a screen printing business, and a fishing podcast before any of this. He will be the first one to tell you that his success came after a long string of things that didn't work.What we actually dig into here is the thinking behind the system, not just the mechanics. Billy talks about how he gave himself 90 days to figure out if the Amazon Influencer Program could become a real business, what live shopping looks like as a sustainable revenue model, and why he specifically targets smaller brands that don't have a content team. We also spend real time on community, because Billy has built one around all of this and has some clear opinions about what community is actually for.This is a good one for anyone who has been curious about the Amazon Influencer Program, anyone thinking about brand deals as a revenue stream, or anyone who just wants to hear from somebody who built something practical and is willing to talk about how it actually went.What You'll Learn:How Billy went from closing down a screen printing business during the pandemic to producing 4,500 Amazon videos in under four yearsWhy small brand deals are a more accessible and often more lucrative opportunity than most content creators realizeWhat live shopping looks like as a real revenue model and what it takes to get started on platforms like Amazon Live and WhatNotHow Billy structures his 90-day proof-of-concept approach when he's testing whether a new idea can become a businessWhy Billy made his main community free and what he does differently with a small, invite-only paid coaching groupWhat it looks like to build a content business when you have ADHD, no degree, and a long history of things not working outAbout Billy Thorpe:Billy Thorpe is a content creator, Amazon Influencer, and brand deal specialist based in Puerto Rico. He has produced over 4,500 product videos through the Amazon Influencer Program and works primarily with smaller brands that are looking for consistent, quality content without a massive budget. He also runs a community for creators learning the Amazon side of the business and a small, invite-only coaching group for people who want to go deeper. Find him by searching "Billy Thorpe Influencer" on YouTube.Connect with Generator:Website: https://generatorpodcast.comInstagram: @generatorpodcastBe a guest: generatorpodcast.comConnect with Stonetree Creative:Website: https://stonetreecreative.comInstagram: @stonetreecreativeResources Mentioned:Amazon Influencer Program: amazon.com/influencer-programWhatNot (live selling platform): whatnot.comEcamm Live: https://www.ecamm.com/mac/ecammlive/?fp_ref=generatorEcamm Creator Camp: ecamm.com
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96 MIN
073 - Getting Good at Claude (For Photographers)
MAR 19, 2026
073 - Getting Good at Claude (For Photographers)
Getting Good at Claude: Why Most Photographers Give Up Too Soon (And How to Fix It)Have you tried Claude once, gotten something too generic to be useful, and just moved on?This episode is the podcast version of my live webinar, Getting Good at Claude for Photographers. I'm breaking down why I switched from ChatGPT to Claude after two and a half years, what the cold start problem is, and why it's the reason most photographers abandon AI tools after a week. More importantly, I'm teaching you how to solve it by building five reference files that give Claude permanent context about who you are and what your business actually does.I need to be upfront about something before we get into it. I turned this entire process into a product that's available at generatorpodcast.com for $37. The product includes a full-length video walkthrough, a polished setup guide that takes you through everything step by step, and the five interview prompts I built specifically for photographers. One prompt per file, ready to paste, so you can open Claude right now and build your files today without figuring out what to ask.Those prompts are not in this episode. That's the one thing I'm holding back. You'll understand the concept completely by the time this is over, and you'll know exactly what the prompts need to accomplish. Whether you want to write them yourself or just use the version I already built for you is your decision.What You'll LearnWhy ChatGPT's constant apologizing and agreement isn't actually helpful. I explain sycophancy in AI tools and why a yes-man doesn't make you a better photographer or business owner.How Claude pushes back when your premise is wrong instead of just validating whatever you say. I share real examples of Claude challenging my thinking and why that friction produces better work.What the cold start problem is and why it kills most photographers' AI usage within a week. You'll understand why every conversation starting from zero context produces generic garbage that doesn't sound like you.How to build five reference files that solve the cold start problem permanently. I break down the purpose of each file and what information needs to go into them so Claude knows your business like a long-time employee would.Why the order matters when you build these files and which one to start with. I explain the logical sequence that makes each subsequent file easier to create.What happens when you load your files into every Claude conversation from day one. You'll see how context transforms outputs from competent but generic to sounding like you wrote it on a good day.How to use Claude for client email responses that maintain your voice and policies. I walk through the prompt structure for inquiry responses and difficult post-delivery situations.Why asking Claude for recommendations is the least useful thing you can do. I teach you how to frame prompts so Claude surfaces questions and problems instead of just telling you what it thinks you should do.How to make Claude your CRM expert by feeding it documentation from 17Hats, HoneyBook, or whatever you use. This workaround saves hours of clicking through help centers trying to figure out automation logic.What the five core use cases are that photographers actually need AI for. Email, marketing plans, campaign ideation, thinking partner for business decisions, and CRM workflows.Get the Full SystemEverything I taught in this episode is available as a complete product:Getting Good at Claude for Photographers - $37Buy now at generatorpodcast.comWhat's included:Full-length video walkthrough of the entire setup processWritten setup guide with step-by-step instructionsFive interview prompts (one per reference file) built specifically for photographersReady-to-paste prompts for all five core use casesEmail response prompts for inquiries and difficult client situationsMarketing plan prompt that constrains Claude to your actual available timeCampaign ideation prompt that surfaces problems instead of recommendationsThinking partner prompt for pricing decisions and business pivotsCRM workflow prompt structure for any platformThe link is in the show notes. You can write your own version of every prompt based on what I described in this episode, or you can use the ones I already built. Either way works.Listen & SubscribeNever miss an episode. Subscribe to Generator on your favorite podcast app:Apple Podcasts | Spotify | YouTubeEnjoyed this episode? Leave a 5-star review on Apple Podcasts to help others discover these conversations.Connect with GeneratorWebsite: generatorpodcast.comInstagram: @generatorpodcastTikTok: @generatorpodcastYouTube: @generatorpodcastHost: Matt Stagliano - Stonetree Creative, MaineGenerator is a podcast about the creative process, personal growth, and what it means to build something meaningful. Hosted by portrait photographer Matt Stagliano.KeywordsClaude for photographers, AI photography business, ChatGPT vs Claude, AI tools photographers, photography business automation, client email templates AI, photography marketing AI, CRM automation photographers, AI thinking partner, photographer workflow AI, cold start problem AI, context files Claude, photography business AI, AI prompt engineering photographers, Anthropic Claude
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46 MIN