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.

Episode List

074 - Stop Chasing Maybe Money with Billy Thorpe

Apr 3rd, 2026 4:00 AM

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

073 - Getting Good at Claude (For Photographers)

Mar 19th, 2026 8:00 PM

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

072 - WPPI 2026 Recap

Mar 9th, 2026 6:00 PM

Generator Live: WPPI 2026 Recap - The Good, The Bad, and The Dance CircleWhat happens when you find yourself in the middle of a dance circle surrounded by phones at a photography conference after party?This is a solo Generator Live episode recorded the day after I got home from WPPI 2026 in Las Vegas. I'm sitting here with whatever plague circulates through Vegas conferences, no voice, exhausted from traveling through the night, and needing to process everything that happened before I lose the context. This is completely free form, just me working through the highs and lows of the conference while my immune system waves a white flag.I spoke on stage at the Fujifilm Lounge and the podcast stage, recorded a live Generator episode with Josh Beaton in front of an audience, connected with photographers I've only known online, and ended the week in a spontaneous dance circle that felt equal parts terrifying and liberating. But I also dealt with hour-long check-in lines, cellular coverage that forced people to crouch by water coolers for signal, and the weird energy that comes with massive trade shows in 2026.What You'll LearnWhy the Rio's infrastructure problems affected the entire conference experience. I break down the cellular connectivity issues, climate control disasters, and check-in chaos that created friction from day one.How badge enforcement at trade shows can create an unwelcoming environment. I discuss the experience of being stopped repeatedly and what that does to the flow of a multi-day conference.What it feels like to speak on stage and record a live podcast episode for the first time. I share the nerves, the energy, and why doing Generator live with Josh Beaton felt like full circle from our conversation a year ago.Why connecting with online friends in person changes everything. I talk about finally meeting photographers I've only interacted with digitally and how those face-to-face moments build real community.How conference parties reveal who your people really are. I describe the moment I found myself in a dance circle surrounded by phones and realized I felt completely safe being ridiculous with this group.What happens when you need to separate from an event for 48 hours before processing it. I explain why I'm not touching photos or videos yet and why that space matters after intense conferences.Why supporting educators and artist friends at local events matters as much as attending major conferences. I emphasize showing up for talks, retreats, and smaller gatherings in your area.How the photography industry's larger challenges show up at trade shows. I clarify that my critiques aren't about production staff but about symptoms of where the industry sits right now.What it means to show up consistently even when you're sick and exhausted. I talk about pushing through to do this recap live instead of waiting, and why that consistency matters for building community.Why the experience was worth every dollar despite the problems. I get honest about what I spent and why I wouldn't ask for a dime back, even with the Rio's issues and the physical toll.Resources MentionedBook Pre-Order & WPPI Goodies: generatorpodcast.com/wppi Free downloads, merch codes, and Ecamm 15% off subscription code (exclusive deal)Apply to be on Generator: generatorpodcast.com/applyEcamm Live: Powers all Generator Live broadcastsListen & 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.com Instagram: @generatorpodcast TikTok: @generatorpodcast YouTube: @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.KeywordsWPPI 2026 recap, photography conference Las Vegas, WPPI Rio hotel, Generator Live stage, photography trade show, conference networking photographers, Fujifilm Lounge WPPI, photography community, conference dance party, photographer meetups, WPPI connectivity issues, photography industry 2026, conference recap, creative community building, photography conference tips

071 - Live at WPPI 2026 with Josh Beaton

Mar 9th, 2026 5:15 PM

Generator Live at WPPI 2026: Josh Beaton on Following Dreams, Self-Esteem, and Starting Over at 50What happens when you decide to chase the dream you always thought was unattainable, even if it means starting over at 50 years old?Josh Beaton is a Chicago-based portrait photographer and fine art artist who also runs Tween Esteem, a 501c3 nonprofit dedicated to building self-confidence in teenagers through portrait photography. A year ago, Josh won his category at WPPI and received the Jerry Ghionis scholarship at his first major conference. Now he's closing his Chicago studio, moving to New York, and pivoting from portrait work to commercial and editorial photography. The dream he's been following his entire adult life suddenly doesn't feel so unattainable anymore.This is the first Generator episode I recorded live on stage, and I brought Josh back exactly one year after our original conversation about the currency of kindness. We recorded this at WPPI 2026 in front of a live audience, and we talk about what it feels like to walk back into a conference without the same wins, how Jerry and Melissa Ghionis believing in him meant more than any prize, and why he's choosing to be weirder as he rebuilds everything from scratch.What You'll LearnWhy hearing that people believe in you matters more than any award or prize. Josh explains how Jerry and Melissa Guionis announcing the scholarship in front of hundreds of people gave him something no trophy could provide.How to know when it's time to stop doing what you like and start chasing what you actually dream about. He talks about following Annie Leibovitz's work for decades and finally deciding to take the leap toward editorial and commercial photography.What it means to fail at something you don't want to do anyway. Josh shares Jim Carrey's philosophy about why you might as well take risks on work you love, since failure is possible either way.Why telling strangers you love their work matters more than you think. He describes the feeling of having someone approach you at a conference just to say they appreciate what you do, and why introverted photographers need to hear it.How closing a successful Chicago studio to move to New York at 50 actually happened. Josh gets real about the decision-making process with his wife and why waiting five more years would just make him 55 years old with the same regrets.What happens when you rebuild your website and remove the thread that connects all portrait photographers. He talks about the terror and satisfaction of watching his site evolve into something that doesn't look like everyone else's anymore.Why you should check for 501c3 status before donating to any nonprofit. Josh breaks down the difference between buying a dot-org domain and actually filing government paperwork to become a legitimate charitable organization.How Tween Esteem uses portrait photography to build self-confidence in teenagers. He explains the program's mission and why this work has become central to his identity as a photographer.What it's like to return to WPPI without winning anything this year after sweeping categories last year. Josh gets honest about the different feeling of showing up without an entourage and how that challenges your sense of accomplishment.Why being weirder is the advice he'd give his younger self. He points to the print competition and recognizes that the photographers he admires most are the ones who were weird in high school and stayed that way.Guest ResourcesJosh Beaton Portrait and fine art photographer based in Chicago, transitioning to commercial and editorial work in New YorkWebsite: joshbeaton.com Nonprofit: tweenesteem.org (501c3) Instagram: @joshbeatonphotographyListen & 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.com Instagram: @generatorpodcast TikTok: @generatorpodcast YouTube: @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.KeywordsJosh Beaton photographer, WPPI 2026, career transition photography, Tween Esteem nonprofit, photographer self-esteem, Chicago portrait photographer, New York photography, Jerry Ghionis scholarship, editorial photography career, commercial photography transition, starting over at 50, photography conference, creative reinvention, teenage self-confidence, portrait photography nonprofit, Jim Carrey philosophy, following creative dreams

070 - Generator Live: Nino Batista on AI, Retouching, and What Makes Art Actually Matter

Feb 2nd, 2026 4:00 AM

Can AI replace the human element that makes photography and retouching valuable, or are we measuring the wrong thing entirely?Nino Batista is a photographer, retoucher, and educator whose work spans commercial photography and fine art. He's known for his technical expertise in retouching and his thoughtful approach to how technology shapes creative industries. After watching AI infiltrate photography and retouching over the past few years, Nino has developed a clear perspective on what actually matters when machines can generate images in minutes.This is a Generator Live episode recorded in real time. I brought Nino on to talk about the Evoto controversy, AI's impact on photography and retouching, and what happens when your entire career can be replaced by a prompt. We get into the uncomfortable truth about dismissible work, why workflow efficiency matters more than tools, and how the human story behind an image creates value that AI simply cannot replicate. The conversation moves through ethics, client relationships, and how Nino's own values have shifted over 17 years in the industry.What You'll LearnWhy art created by humans carries inherent meaning that AI-generated content cannot replicate. Nino explains how knowing a person created something adds layers of interest and value, even when the final product looks similar.What it means when your photography or retouching work can be replaced by AI overnight. He gets blunt about dismissible work and what that reveals about the industry's actual priorities.How the story behind an image matters as much as the final product. Nino breaks down why we subconsciously ask different questions about human-made work versus AI-generated content.Why retouchers need to prioritize workflow efficiency over expensive tools. He shares his approach to creating Photoshop actions that save hours while maintaining quality and teaching clients how everything works.What photographers miss by treating retouching as an afterthought instead of recognizing it as its own art form. We discuss how the retouching community contributes to photography but often gets overlooked.How to think about AI as a recalibration moment rather than an existential threat. Nino describes moving from terror to a more grounded understanding of what technology can and cannot do.Why speed and efficiency in content creation matter more than perfection. I share how switching to live recording eliminated editing time and let me focus on delivering value instead of post-production.What supply and demand reveal about the photography industry's actual needs. Nino explains why clients choosing faster AI solutions over slower human work tells us something important about what we were making.How hand-stitched leather and artisan craftsmanship parallel the value of human-made art. He uses this analogy to explain why provenance and process matter beyond just the end result.Why workflow optimization should come before tool acquisition. We both emphasize understanding your own process first, then finding tools that support it, rather than chasing every new technology.How Nino's values evolved over 17 years from focusing on end results to prioritizing authenticity and personal pride. He shares why drawing clear boundaries around your work matters more now than ever before.What happens when photographers treat clients as content instead of individuals. We discuss the tension between maintaining artistic vision and meeting client demands for perfect, AI-generated results.Why high-end retouchers might transition into AI workflow consultants. Nino explores how understanding both craft and technology positions photographers to help others navigate ethical implications of AI tools.How the tactile and emotional aspects of live performance and physical media cannot be replicated digitally. We talk about why attending live shows and holding album covers creates connections that streaming never will.What clients actually care about when it comes to your process. Nino explains why most clients view photography as magic and don't care about technical details, which changes how we should talk about our work.Guest ResourcesNino BatistaPhotographer, retoucher, and educator specializing in commercial and fine art photographyWebsite: ninobatista.comListen & 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. https://podcasts.apple.com/us/podcast/generator/id1668192673Connect 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.KeywordsAI in photography, photography retouching, Nino Batista photographer, AI-generated images, Evoto controversy, retouching workflow, human element in art, photography industry AI, commercial photography, fine art photography, Photoshop actions, creative workflow efficiency, AI replacement photography, retoucher perspective, meaningful photography, photography ethics, authenticity in art, AI workflow consulting, client relationships photography, artistic boundaries, human craftsmanship

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