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Generator

Generator

Di: 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.Copyright 2026 Matt Stagliano Arte Economia Gestione e leadership Leadership Successo personale Sviluppo personale
  • 075 - No Admin, Just Shoot with Ashley Siegert
    Apr 10 2026
    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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    1 ora e 21 min
  • 074 - Stop Chasing Maybe Money with Billy Thorpe
    Apr 3 2026

    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 years
    • Why small brand deals are a more accessible and often more lucrative opportunity than most content creators realize
    • What live shopping looks like as a real revenue model and what it takes to get started on platforms like Amazon Live and WhatNot
    • How Billy structures his 90-day proof-of-concept approach when he's testing whether a new idea can become a business
    • Why Billy made his main community free and what he does differently with a small, invite-only paid coaching group
    • What it looks like to build a content business when you have ADHD, no degree, and a long history of things not working out

    About 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.com

    Instagram: @generatorpodcast

    Be a guest: generatorpodcast.com

    Connect with Stonetree Creative:

    Website: https://stonetreecreative.com

    Instagram: @stonetreecreative

    Resources Mentioned:

    • Amazon Influencer Program: amazon.com/influencer-program
    • WhatNot (live selling platform): whatnot.com
    • Ecamm Live: https://www.ecamm.com/mac/ecammlive/?fp_ref=generator
    • Ecamm Creator Camp: ecamm.com

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    1 ora e 36 min
  • 073 - Getting Good at Claude (For Photographers)
    Mar 19 2026
    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, ...
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    47 min
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