It Pays to Write

Jack W.

Welcome to It Pays to Write. The show where we break down how simple writing skills, habits, and systems to help you create digital leverage in your career, business, and life. We'll cover all that and more on the show: → Simple writing habits and systems to build a brand and audience → How to create content that generates inbound opportunities, leads, and sales → AI skills and tools to 10-100x your out put and results → Chats with expert writers, marketers, founders, and creators to help you put ideas to action Let's dive into how writing can change your present and future.

Episodes

  1. 13/11/2025

    Can Email Writing Change Your Career?

    Lauren Gibson is a ghostwriter and email marketer helping agency owners and coaches grow their businesses through content. She’s the founder of the “Connections” newsletter and writes daily on LinkedIn about business, brand building, and the future of work.But she didn’t start in marketing. From navigating Egyptian taxis without GPS to landing meetings with Ethereum’s co-founder, Lauren’s path has been anything but linear. In this episode, she shares how writing in journals, essays, and LinkedIn posts helped her transition from Web3 startup chaos to a thriving solo business.Lauren opens up about losing her job, journaling through uncertainty, and the power of experimenting until something sticks. She breaks down how she used content to attract clients, build authority, and monetize her writing skills. If you’ve ever felt stuck in your career or unsure how to sell what you know, this one’s a must-listen.Key Takeaways Writing got Lauren into Georgetown and into businessShe used journaling to find clarity and directionLinkedIn content brought in warm leads and referralsStarting a newsletter helped her test her voice and nicheHer first three clients came from one LinkedIn postCommunity and connection were core to her growthAI is helpful, but human-first writing still mattersOwnership is more than Web3 — it’s choosing your workShe made past income back within two yearsYour story is your most valuable business assetThe Artist’s Way by Julia Cameron: https://juliacameronlive.com/the-arti...Connections Newsletter by Lauren Gibson: [VERIFY: insert correct link if known]Lauren on LinkedIn:   / linkwithlauren  Remarkable Tablet: https://remarkable.com/Shield Analytics: https://www.shieldapp.ai/AuthoredUp: https://authoredup.com/Claude by Anthropic: https://claude.ai/Timestamps00:00 Lauren’s wild path: from nomad life to email marketing02:53 How writing got her into Georgetown’s MBA06:14 From teaching English to Web3 and Joe Lubin09:03 The power of networking and warm intros12:02 Why Web3 ideals matter more than the tech14:51 Depression, reflection, and finding her voice18:01 The first step: writing daily and announcing a business20:55 Building a newsletter and community from scratch23:57 How The Artist’s Way helped her show up daily26:55 Leveraging LinkedIn to test and grow ideas29:54 Losing a job, moving home, and finding stability42:11 Writing opened up new roles, even big four intros44:25 Why Lauren avoids over-relying on AI46:24 From pro bono clients to a paid, growing business50:40 Who she works with now and what she offers53:26 Legal risks of AI-generated writing1:00:41 You own the IP — your story, your face, your wordsResourcesAdditional ResourcesStart writing online today with my Free AI Writing Roadmap course: https://aiwritingroadmap.com/ Connect with Jack on LinkedIn:   / jackwrites   Like and Subscribe to the It Pays to Write Podcast on your favorite platforms:Spotify: https://open.spotify.com/show/5tiiZAc... YouTube:    / @itpays2write   Substack: https://itpaystowrite.substack.com/s/... Apple: https://podcasts.apple.com/us/podcast...

    1h 12m
  2. 08/11/2025

    Youtube Lead Generation MasterClass: 0 to 14K subs with $0 ads

    Dylan Davis shares his incredible YouTube lead generation journey, growing to 14,000 subscribers in just seven months and getting 2 to 6 leads/wk sharing AI automation tips and processes. He provides valuable YouTube and AI use tips and tactics and discusses how to turn your YouTube channel into a lead generation machine. Learn how to boost YouTube video content creation to generate qualified leads for your business. Chapters 00:00 How Dylan books AI consulting work and who actually pays03:02 How to learn AI tools fast by building real things05:54 Who he serves and how he removes the biggest blockers08:47 How to copy proven automations for your team today11:50 The perfect AI tool stack: Playwright, Gemini, ChatGPT, and when to use each14:54 How to write faster with AI using prompts, structure, and the right model17:53 How Dylan coaches models to write crisp, on brand drafts21:01 How to spot AI writing and fix the tells before you publish23:47 Why your content changes next as models level up30:50 How to protect your role as busywork disappears36:27 Your 90 day plan to get ahead of AI disruption41:13 Why you still matter when machines handle the tasks44:53 How Dylan left a 20 person AI team to launch solo52:37 How to go from unknown to in demand with YouTube01:01:51 How to get your podcast found when most stay invisible01:03:02 How Dylan’s title first system ends the struggle bus phase01:04:39 Why he makes only long videos and why buyers love YouTube01:08:44 How Dylan built a repeatable plan that pulls 1 to 6 leads a week01:11:52 How to use a mid roll freebie, a simple landing page, and a VSL to convert01:19:55 The day one playbook Dylan wishes he had Like and Subscribe to the It Pays to Write Podcast YouTube▶ https://www.youtube.com/@itpays2write Spotify▶ https://open.spotify.com/show/5tiiZAcG630B8xAqd2wvgi?si=3d5137ef8ead4cdf Substack▶ https://itpaystowrite.substack.com/s/it-pays-to-write Apple▶ https://podcasts.apple.com/us/podcast/it-pays-to-write/id1823979904 Grab my free AI Writing Roadmap coursehttps://aiwritingroadmap.com/ Connect with Jack on LinkedInhttps://www.linkedin.com/in/jackwrites/

    1h 27m
  3. 13/09/2025

    How to Use ChatGPT: Guide for Beginners

    How to Use ChatGPT: Guide for BeginnersEpisode Summary Dan Sanchez, AI educator and host of AI-Driven Marketer* joins Jack to share a real-world beginner’s guide on how to use ChatGPT the right way.Forget fancy prompts and endless tool lists. Dan walks you through the actual skills that separate casual users from smart operators. You’ll learn how ChatGPT’s memory really works, why context matters more than prompts, and how to build systems that make ChatGPT 10x more useful. Dan also breaks down how to train custom GPTs, use ChatGPT agents, and coach the model for better writing, research, and marketing tasks. He shares beginner-friendly examples that any marketer, freelancer, or creator can apply immediately. Whether you're brand new to ChatGPT or trying to get more out of it, this episode gives you a clear path forward. If you're tired of surface-level tips and want practical, repeatable ways to use ChatGPT better, this one’s for you. Timestamps 00:00 Why AI Marketing Is Exploding Right Now 04:20 The Tools Aren’t the Answer — This Is 07:17 AI Memory Explained: Why Most People Miss This10:17 Context Engineering: The Skill That Separates Pros 13:25 AI in Action: Real Marketing Use Cases That Work16:15 Fail Fast: Why Marketers Should Experiment with AI 19:18 Can AI Kill Critical Thinking? Here’s the Truth 22:13 Why Failing with AI Is the Fastest Way to Learn 25:21 Coaching AI: How to Get Better Results Every Time 28:09 Testing Limits: Using AI for Big, Risky Tasks 36:44 Want Personalization? Start with Better Processes 38:05 Stop Guessing: Map Your Work to AI, Step-by-Step 39:23 What to Automate vs. What to Delegate with AI 42:10 Content Creation at Scale: What AI Can Actually Do 43:35 Messy Process? AI Won’t Help Until You Fix This46:21 SOPs and Custom GPTs: Build Once, Use Forever 52:24 Why Documenting Your Work is Now a Superpower 58:24 How Writing and Process Thinking Boost AI Use 01:01:27 The “Helpful Neighbor” Mindset for Smarter AI Use 01:03:29 Advanced Tactics: Coaching, Prompting, and Projects 01:07:33 Outro Resources Dan’s website: https://danchez.com/AI-Driven Marketer Podcast: https://danchez.com/podcastTim Ferriss on delegating to VAs: https://fourhourworkweek.com/Copywriting Secrets by Jim Edwards: https://www.copywritingsecrets.com/Claude by Anthropic: https://www.anthropic.com/index/claudeChatGPT Agents: https://openai.com/chatgptSocial Media Examiner: https://www.socialmediaexaminer.com/ Want to Start Writing online and using ChatGPT? Start with my Free AI Writing Roadmap course: https://aiwritingroadmap.com/ Connect with Jack on LinkedIn https://www.linkedin.com/in/writeschrute/

    1h 8m
  4. 13/08/2025

    23K Followers in 14 months: How to Grow Your Followers on LinkedIn | With Dustin Hauer

    How to Grow Your Followers on LinkedIn: 23K followers in 14 monthsDustin is VP of International Sales by day—and a fast-growing social media strategist by night. In just 14 months, he's built a LinkedIn audience of over 23,000 followers using a repeatable system that blends evergreen content, smart engagement tactics, and AI-powered comment strategies.In this episode, Dustin unpacks his entire content engine. From growing company pages to building a 180-post content bank, he shares exactly how he formats carousels, splits daily posts into two styles, and uses groups and newsletters for reach. He also explains how AI helps him engage with hundreds of comments while keeping his authentic voice. If you're trying to grow on LinkedIn or turn your audience into income, this episode shows you how to get seen, and what to post once you are.Key Takeaways-Dustin grew from 0 to 23.5K+ followers in 14 months-LinkedIn groups boost visibility and post reach (massively)-AI can help write comment replies that sound like you-Reposting high-performing content monthly is smart, not lazy-Carousels with numbered lists and simple CTAs drive massive impressions and engagement on LinkedIn-Company pages offer 250+ invites per month (*use them)-Newsletter growth leads to long-term audience control-He uses two posts daily to his profile: 1 helpful carousel, 1 short quote or truth-Authenticity still wins, even with AI-generated help-Time-saving tools make it easier to show up every dayTimestamps00:00 How Dustin grew 23K followers in just over a year06:39 Dustin’s LinkedIn-first strategy—and why X didn’t work13:42 Building a brand using carousels, checklists, and company pages23:18 Posting in groups: a secret weapon for massive visibility33:09 Which scheduling tools Dustin uses (and which to avoid)39:26 How Dustin trained AI to reply to 100+ comments a day50:54 Evergreen content, repeat posting, and CTA tricks that work01:01:48 How he built a 3-month post bank (and recycles it)01:07:50 Monetization plans, newsletter growth, and CRM tips01:14:05 Dustin’s advice for new writers starting on LinkedIn01:22:12 Balancing growth, audience, and authenticity with AIResourceshttps://buffer.com/ https://www.apollo.io/ https://gemini.google.com/   / donnellychris     / alicjasmin   https://www.pinterest.com/Just for viewers and listeners of the It Pays to Write PodcastStart writing online today with my Free AI Writing Roadmap course: https://aiwritingroadmap.com/Connect with Jack on LinkedIn: https://www.linkedin.com/in/writeschrute/Like and Subscribe to the It Pays to Write Podcast on your favorite platforms:YouTube:    / @itpays2write  Spotify: https://open.spotify.com/show/5tiiZAc...Substack: https://itpaystowrite.substack.com/s/...Apple: https://podcasts.apple.com/us/podcast...

    1h 32m
  5. 07/08/2025

    How to 2x Your LinkedIn Reach with 30-Day Writing Challenges | Vanessa Yepes

    Vanessa Yepes, a product operations lead at AppSumo with eight years of experience in customer and partner success, transformed her totally unused LinkedIn account into a powerhouse of engagement, authenticity, growth, and connection with other cool people. She doubled her audience in just 60 days of writing on LinkedIn, by doing back-to-back 30 day writing challenges. In this episode, Vanessa talks about how an internal 30-day writing challenge at her company got her bit by the writing and posting bug. And how she’s used multiple, back-to-back writing challenges to: Sharpen her social media writing skillsFigure out how to create community and build an audience on LinkedIn (super fast!)Ignite her passion for writingStart growing her personal brand online She shares the nuts and bolts of competing on metrics using Shield Analytics, the evolution of her “text-message-style” writing, and how she’s integrated AI—like voice notes, ChatGPT projects, and AI note-takers like Fathom—to streamline brainstorming, drafting, and meeting notes in her day job and her writing. Whether you’re a nine-to-fiver or a freelancer, this conversation is packed with writing skills, habits, tools, and software you can use to start writing online today (and make it a lot easier with AI). Timestamps 00:00:00 - How Vanessa went from support agent, to head of operations, to obsessed with writing on LinkedIn 02:45:00 - How she crushed her company 30-day LinkedIn writing competition 06:02:00 - How she’s finding and developing her signature style (and helping you find yours) 08:55:00 - How she uses AI to brainstorm so you never face a blank page 11:46:00 - Why authenticity wins for everyone 14:56:00 - How she’s building community through storytelling 17:57:00 - Her next big goals to inspire yours 37:31:00 - Organizing her thoughts into content gold 38:52:00 - The AI co-writer she trusts 40:54:00 - How to crush drafts with tight feedback loops 43:23:00 - How she uses writing for self-discovery 45:08:00 - He techniques for mining and creating endless posts 51:13:00 - Managing projects with AI efficiency 54:09:00 - How she puts meeting notes on autopilot with AI 56:06:00 - Recognizing real professional value 01:00:48 - How she taps into LinkedIn’s community power 01:10:09 - Her evolving engagement tactics and how they work 01:15:08 - How she’s embracing a true LinkedIn voice 01:17:16 - Why you need strength in support networks on social media 01:20:37 - Why starting small in comments builds confidence for posting 01:22:59 - How to cultivate LinkedIn post ideas with daily reps 01:24:48 - How you can turn everyday moments into stories 01:28:21 - The neuroscience behind compelling storytelling 01:32:18 - How to build friendships through writing challenges 01:38:29 - How experimentation can fuel growth 01:43:51 - How she sets intentional writing goals 01:46:20 - Her top advice for your writing journey Shield Analytics (LinkedIn metrics tracker): https://shieldapp.io/ChatGPT (AI writing assistant): https://chat.openai.com/Fathom (AI meeting transcription & summary): https://fathom.video/AppSumo (SaaS deals & Sumo Day): https://appsumo.com/Vanessa’s LinkedIn: https://www.linkedin.com/in/vanessayepes/Mason’s LinkedIn: https://www.linkedin.com/in/masonjohnston935/ Like and Subscribe to the It Pays to Write Podcast on your favorite platforms: Spotify https://open.spotify.com/show/5tiiZAcG630B8xAqd2wvgi?si=3d5137ef8ead4cdf YouTube https://www.youtube.com/@itpays2write Substack https://itpaystowrite.substack.com/s/it-pays-to-write Apple https://podcasts.apple.com/us/podcast/it-pays-to-write/id1823979904 Start writing online today with my Free AI Writing Roadmap course: https://aiwritingroadmap.com/** Connect with Jack on LinkedIn: https://www.linkedin.com/in/writeschrute/ ResourcesFollow and Subscribe to the It Pays to Write Podcast

    1h 51m
  6. 30/07/2025

    From 1K-7K Followers in 6 months: How to Grow on LinkedIn with Carousel Posts | With Simon Schmitz

    What does it really take to grow from 1K to 7K+ LinkedIn followers in six months, without turning into another “broetry” meme? Implementation-manager-by-day and content strategist-by-night Simon Schmitz breaks down the tactics behind his meteoric rise. Simon explains why carousels still beat every other format on reach, why text-only posts often out-perform image posts, and how LinkedIn’s shifting algorithm is rewarding niche expertise over generic marketing garbage posts. He shares a realistic workflow (two carousels + one text post per week), complete with tools like Canva, Whisper Flow voice dictation, and ChatGPT to draft hooks fast. Most importantly, he urges new writers to “embrace the suck,” post on a sustainable schedule, and inject real personality instead of AI-generated fluff. If you’ve been scared to show up and post on LinkedIn—or you’re stuck with low reach and engagement—Simon’s playbook and refreshingly direct take will get you publishing (and enjoying it). Why You’ll Love This Episode → How to set a three-day posting cadence you can actually stick with. → The “hook + re-hook” formula that keeps readers tapping Read More. → Voice-to-text workflow that turns a ramble into a polished post in 20 min. → When to use carousels vs. text vs. video (and why selfies still matter). → A starter list of 7 LinkedIn writers worth studying—plus the tools they use. → Real talk on AI: leverage without losing your own critical-thinking muscles. Simon’s Links → LinkedIn – https://www.linkedin.com/in/simon-schmitz-tx/ → Stan Store – https://stan.store/AperolSchmitz → Personal Branding Carousels (featured) – see his LinkedIn “Featured” tab → Email – DM via LinkedIn for branding inquiries Software & Tools Mentioned CanvaChatGPT / GPT-4oWhisperFlow (voice-to-text)TypeGrow formatter Follow Simon → LinkedIn – https://www.linkedin.com/in/simon-schmitz-tx/ → Stan Store – https://stan.store/AperolSchmitz → Personal Branding Carousels (featured) – see his LinkedIn “Featured” tab → Email – DM via LinkedIn for branding inquiries It Pays to Write → Grab your FREE 5-Day AI Writing Roadmap: https://aiwritingroadmap.com → Connect with Jack on LinkedIn: https://www.linkedin.com/in/your-profile

    1h 42m
  7. 18/07/2025

    From Layoff to 100K+ Followers | With Jennifer Chou

    Jennifer Chou went from blowing up her companies TikTok account, to → Growing her own audience to 80K+ people (now it’s well over 100K) → Getting laid off from that job → Replacing her $6k/month salary with a 24 hour sale of her first course Jennifer, better known online as Vegan Tech Nomad, turns unhinged data dashboards, her content marketing strategy, poop-tracking, marathon training, and more into viral content gold. In this candid chat she walks Jack through the exact steps that grew her Instagram to 80K+, replaced a month’s salary in a single launch day, and helped thousands of ADHD creators reclaim their time with life-tracking. If you want a repeatable framework to post consistently, ditch burnout, and monetize fast, start here. Why you'll love this episode: Learn the 4-week Life Tracking Framework that keeps ADHD brains on track.See how Jennifer tests hooks on TikTok before syndicating winning videos.Borrow her “vibes-based” creativity rule to kill perfectionism.Understand the psychology tweaks (progress bars, tiny wins) that boost course completion.How to overcome your fears, challenges, and mindset roadblocks to creating contentHear real student wins—from new clients to “first course ever finished.” Top Takeaways & Timestamps 00:49 – Origin Story: Why a breakup over her username sparked the Vegan Tech Nomad brand.02:26 – Poop-Tracking Pays: Viral video and first life-tracking course idea.04:26 – Five-a-Day Posting: Spam-posting TikToks for her employer and lessons learned.05:28 – $6 K in One Day: Course launch beats former monthly salary.07:28 – Celebrate Tiny Wins: How $300 felt bigger than $6 K—and why mindset matters.12:05 – 100 K Followers in a Year: Reps, hook testing, and volume over polish.17:06 – “Everything Is Vibes”: Fun first, analytics second—results follow.22:25 – Cross-Platform Surface Area: Use TikTok as R&D, Instagram/YouTube for scale.29:38 – New Mission: Pivoting life-tracking toward overwhelmed founders.35:25 – Product Ladder: Templates → Cohort → Course; pricing psychology that converts.37:57 – Cohort → Course Flip: Why she ditched daily Zoom calls and made her ADHD program evergreen.42:18 – Therapy Beats Tactics: Students raved about mindset modules over hook formulas—and what she learned.50:06 – UX That Sells: Progress bars, badges, and “cute sounds” that nudge learners to finish.55:53 – Life-Tracking Stack: Daily wins, weekly reflections, and a North-Star metric anyone can steal.1:02:59 – Coach B Energy: Building self-compassion to calm rejection-sensitive ADHD brains.1:09:55 – Post With Joy: The 7-second routine that turns content creation into pure play.1:15:40 – Community Boost: Discord + comment pods that wipe out imposter syndrome.1:22:31 – Permission to Pivot: Smashing limiting beliefs and making creativity fun again. Her Resources & Mentions Creator Templates – https://chaotic-creator.beehiiv.com/c/creator-templatesContent Business Tech Stack – https://www.notion.so/Content-business-tech-stack-7112518bd7d5403f8fc78a8af109f374?pvs=21Productivity Tools List – https://www.notion.so/Productivity-tools-I-use-005b5acdbba5418ab6b96675587e4465?pvs=21Jennifer’s Life-Tracking Course – https://vegantechnomad.lemonsqueezy.com/Her Income-Report Playlist – https://www.youtube.com/watch?v=ce929wXuXUI&list=PLVfia6kpvNgtIQv_MnDR1HJTj2zEPdLDbHer Testing Video Hooks Example – https://youtu.be/hTBwEkrvwaAHer story on “I Got LAID OFF, then SOLD a COURSE for $40,000 (step-by-step guide)”: https://youtu.be/sVgpnGvUtA8?si=sXvmRNWqYFlrmJobStan Store – https://stan.store/vegantechnomadWebsite: https://www.vegantechnomad.comYouTube: https://www.youtube.com/@vegantechnomadInstagram: https://instagram.com/vegantechnomadNewsletters: https://vegantechnomad.beehiiv.com, https://chaotic-creator.beehiiv.com Free 5-Day Course on How to Write with AI: https://aiwritingroadmap.com/ Follow Jack and It Pays to Write on LinkedIn: https://www.linkedin.com/in/writeschrute/

    1h 26m
  8. 01/07/2025

    How to Build Your Own AI Life Coach | With Matt Herman

    Our guest today is the brilliant Matt Herman. He’s a content-marketing pro at Aeroseal, an AI warlock, songwriter, and all-around creative. Matt and Jack dig into practical AI use cases in content marketing, smarter ChatGPT workflows, turning generative AI into a pocket life coach, and keeping the human spark alive in writing and other creative processes. Then they nerd out on AI: how to write with it (and how not to), how it can double as a pocket therapist, and how it’s reshaping the way we market, create, and solve problems. They swap real-world stories, share stress-tests, dabble in a bit of doom-and-gloom theory, and break down what separates great AI prompts and projects from mediocre ones. Free 5-Day AI Writing Email Course: https://aiwritingroadmap.carrd.co/ Matt on LinkedIn:  / mattwherman   Jack on LinkedIn:  / writeschrute   Key Takeaways & Topics AI tools can enhance creativity and writing efficiency.Context is critical when using AI for writing, marketing, and creative tasks.AI can support your therapy journey or act as a life coach.How to write with AI—the right way and the wrong way.Custom GPTs can be tailored to individual needs and preferences.AI technology is evolving at a crazy pace.The combination of human insight and AI drives personal growth.AI can help users navigate complex emotional situations.Art and creativity will always retain a human element.AI can provide immediate answers and solutions to problems.Why speaking to AI is better (and faster) than writing, and how to do it.The future of AI remains uncertain (does anyone actually know what the heck will happen)?

    59 min

About

Welcome to It Pays to Write. The show where we break down how simple writing skills, habits, and systems to help you create digital leverage in your career, business, and life. We'll cover all that and more on the show: → Simple writing habits and systems to build a brand and audience → How to create content that generates inbound opportunities, leads, and sales → AI skills and tools to 10-100x your out put and results → Chats with expert writers, marketers, founders, and creators to help you put ideas to action Let's dive into how writing can change your present and future.

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