Slackers

Josh Saffran has spent his career in sales, first for Colgate-Palmolive and now connecting corporations with supply chain startups through Plug and Play, the Silicon Valley venture firm. He also co-owns The Gents Place in Bentonville, Arkansas, a barbershop built like a members club, complete with a concierge at the door and a speakeasy business lounge.That mix makes him the right person to ask what AI does to a business where the person-to-person relationship is everything. His answer is to move the ringing phone and the supply order away from the people doing the serving, so their full attention lands on the person in the chair. From there, the conversation moves through churn, curiosity, leadership, and what it takes to keep a promise to a customer over time.In this episode- Why Josh set out to build a business that was Walmart and Amazon proof, and where AI fits into it anyway- Inside The Gents Place, where a concierge greets you and the phone never rings in the shop- A doctor's appointment that shows what happens when professionals spend their time on keystrokes- Using AI to make a sales concierge better at the job instead of replacing one- What's your real job, and how much of your day goes to tasks that keep you from it- Why doing five things well beats doing fifteen things badly- What selling to Walmart and Target taught Josh about asking questions- Raising kids who can look someone in the eye, and the difference between AI writing your homework and AI editing it- Doug McMillon's list of retailers that disappeared, and spotting icebergs from two miles out- Why Josh runs his manager meetings as a democracy- Churn, member-for-a-day passes, and why happy members make the best brand ambassadors- What a marriage can teach a membership business about retention- Strategic empathy, emotional labor, and the choice between optimizing for more or for betterWorth repeating> "It's not here to take people's jobs. It's here to upskill and enhance." – Josh> "I hate yes men or women. Challenge me. Tell me why I'm wrong." – Josh> "Doing 15 things in an average or poor way is in no way better than doing 5 to 10 things awesome." – Jonathan> "I am not trying to maximize acquisition in my marriage. I am trying to maximize the retention of my marriage." – JaimeChapters- 00:00 Cold open and introducing Josh- 02:09 From Colgate to Plug and Play to a barbershop- 03:58 AI beyond the tech hubs- 06:09 Building a Walmart and Amazon proof business- 09:10 Inside The Gents Place experience- 13:24 The doctor who was 20 minutes late- 14:54 Upskill and enhance- 16:50 What creatives misunderstand about their value- 19:29 Don't use AI for the sake of using AI- 20:18 Bringing AI to a team that cuts hair- 22:29 What's your real job?- 26:07 Fifteen things on the list- 29:21 What selling toothpaste taught Josh about listening- 31:09 Raising kids in the age of AI- 33:39 Is AI bending us back toward service?- 37:08 Curiosity as the question of our time- 39:33 Your thoughts first, AI second- 42:11 Doug McMillon's list and the iceberg- 43:37 Stuck in strategy or stuck in execution- 46:10 Hire for your blind spots- 47:42 Leadership and paying it forward- 51:08 Pour into the team first- 52:37 Filling the pipeline, and why churn keeps Josh up at night- 56:02 The top-of-funnel hamster wheel- 58:02 In the business of relationships- 59:45 The speakeasy and Gents TV- 01:01:46 Reading the room- 01:07:47 Delivering on the promise- 01:09:51 Strategic empathy and emotional labor- 01:12:29 Embrace it or go drive the bus- 01:14:53 Jaime and Jonathan's debrief- 01:19:22 Activity, progress, and the assembly edit- 01:22:24 Optimizing for more or for betterConnect with Josh- The Gents Place- Plug and Play- Josh Saffran on LinkedInMentioned in this episode- Center for Creative LeadershipFollow Slackers wherever you listen so the rest of season two lands in your feed.Red Threads is an email with one idea a week that changes how you see your work, written by Jaime Solis as part of Tandem Studios. Straight to your inbox. Always free.Check it out. –––The Slackers Podcast is produced by Jaime Solis and Jonathan Sasse.Audio production by Stephen Kallao.Cover art by Jonathan Sasse Connect with Jonathan & Jaime 🎙️ Jonathan Sasse — Co-Founder Tandem Studio and executive advisor.🔗 LinkedIn · Forbes Communication Council 🎙️ Jaime Solis — Music executive, Content & Media advisor, founder Red Threads newsletter.🔗 LinkedIn · Threads · Instagram Thanks for listening!If you enjoyed this episode, please follow or subscribe on your favorite podcast app and leave a quick rating or review. It helps new listeners find the show.

Season two of Slackers opens with Jaime and Jonathan back in the chair together, catching up on what's changed since season one and laying out what's ahead: more conversations with builders and founders, including a run recorded live in Bentonville, Arkansas.A day at Crystal Bridges Museum of American Art sparked the conversation at the heart of this episode. Walking past paintings and sculpture, the two started riffing on a definition of art that sounds a lot like building a company: something that might not work, offered to other people anyway. From there they make the case that the future of meaningful work belongs to professionals who can blend the posture of an artist with the discipline of a trained operator.In this episode- Why Jonathan launched [Tandem Studio](https://tandemstudio.ai), and how Slackers and Red Threads are becoming part of its media arm- What makes Northwest Arkansas such an unusual place to build- The kindergarten test, and how adults train art out of themselves- Artist as a noun versus artist as a verb- How AI is putting longtime professionals back in the kindergartner's chair, and the real costs that come with it- Getting stuck, and why getting unstuck no longer means raising five million dollars- Why so many artists resist AI, plus a royalty-reconciliation use case for working musicians- Creative destruction, the direct-to-VHS shelf at Blockbuster, and what the roots of hip-hop teach about building with the tools at hand- Extraction versus durability as a business model- Sufficiency, and the line just above "not sweating it" where life starts to feel goodWorth repeating"Art is just something that might not work being put into the world." – Jaime"Nobody's problem is I need something that is capable of taking my money." – Jonathan"You get a billion dollars by stepping on a lot of throats, frankly." – JonathanChapters- 00:00 Cold open and welcome back to season two- 02:37 A year of acceleration, and why Tandem exists- 05:26 Building a media arm- 06:11 Why Northwest Arkansas- 07:44 Slackers on the road and a day at Crystal Bridges- 09:07 Art is something that might not work- 13:22 The kindergarten test- 14:54 Artist as a noun, artist as a verb- 16:27 AI and the return of the kindergartner- 20:34 Putting on the artist's mindset- 24:23 Getting stuck and getting unstuck- 30:47 Taste, judgment, and the town photographer- 32:38 Why artists push back on AI- 37:19 Creative destruction and a royalty use case- 39:55 What hip-hop teaches builders- 42:27 Put it out and see who reacts- 44:09 Extraction versus durability- 49:32 Sufficiency- 54:59 What's coming in season twoMentioned in this episode- Red Threads newsletter- Slackers bonus episode with Jared Eichelberger of Five Tool Baseball- Slackers season one episode on creative destruction- Crystal Bridges Museum of American Art- Tandem StudioFollow Slackers wherever you listen so season two lands in your feed.The artists at Crystal Bridges kept showing up to do the work long before anyone was watching. Red Threads is that practice for Jaime, every week since 2024.One idea a week that changes how you see your work.Straight to your inbox. Always free.Send me one → –––The Slackers Podcast is produced by Jaime Solis and Jonathan Sasse.Audio production by Stephen Kallao.Cover art by Jonathan Sasse Connect with Jonathan & Jaime 🎙️ Jonathan Sasse — Co-Founder Tandem Studio and executive advisor.🔗 LinkedIn · Forbes Communication Council 🎙️ Jaime Solis — Music executive, Content & Media advisor, founder Red Threads newsletter.🔗 LinkedIn · Threads · Instagram Thanks for listening!If you enjoyed this episode, please follow or subscribe on your favorite podcast app and leave a quick rating or review. It helps new listeners find the show.

We wrapped 20 episodes. And the feedback that kept coming back wasn’t “give us more frameworks.”It was: “What does this actually look like when I’m sitting at my desk, trying to figure out what to do next?”That question is what Season 2 is all about. Consider this bonus episode a preview: real founders, real operators, and the actual guts of what they’re building. In this episode of Slackers, Jaime Solis and Jonathan Sasse roll up their sleeves with Jared Eichelberger — former professional pitcher in the Mets and Mariners organizations, son of MLB pitcher Juan Eichelberger, and founder of 5ive Tool Baseball Academy, San Diego’s premier youth baseball training organization. Twenty years in, Jared runs a real operation: dozens of coaches, roughly 40 league partnerships, camps from San Diego to Scottsdale to Chicago to Austria, and a business at a genuine inflection point. Key themes include: “Carry your own bag” — why life skills taught in a hurry are the real product Uniformity as trust-building: how looking the part became a brand system Every yes is a no: the deliberate decision to serve rec leagues, not travel ball From 80 lessons a week to a team that runs without you — breaking the founder bottleneck The ownership flywheel: what happens when coaches feel empowered to improve the business Ears open for opportunity: how one parent conversation became the Scottsdale expansion Radical financial transparency — why Jared tells his team exactly what he pays himself Expensive hobby or business? Tracking every event against the P&L Management Mondays, top-three task lists, and auditing where your energy actually goes Why strategic empathy — knowing your customer’s schedule better than they do — is a business asset Jared’s story runs from a single pitching clinic at his high school alma mater to a half-million-dollar operation built almost entirely on organic reach, league relationships, and a 1.5-million-view video about how to size a bat. Along the way he unpacks the systems that made scale possible — from Google Voice and a wall calendar to 41 managed schedules — and the harder work of finding people who share the vision and giving them real ownership of it. Consider this a preview of many insights we unpack in Season 2: a founder who talks for nearly two hours and barely mentions the business — because the culture, the customers, and the craft are the business. The things Jared over-indexes on are the hardest things for any organization to build. He just built them first. Season 2 is coming: more builders, more operators, more behind-the-curtain conversations — in real time, with real stakes. This is what better work looks like up close. –––The Slackers Podcast is produced by Jaime Solis and Jonathan Sasse.Audio production by Stephen Kallao.Cover art by Jonathan Sasse Connect with Jonathan & Jaime 🎙️ Jonathan Sasse — Co-Founder Tandem Studio and executive advisor.🔗 LinkedIn · Forbes Communication Council 🎙️ Jaime Solis — Music executive, Content & Media advisor, founder Red Threads newsletter.🔗 LinkedIn · Threads · Instagram Thanks for listening!If you enjoyed this episode, please follow or subscribe on your favorite podcast app and leave a quick rating or review. It helps new listeners find the show.

Everyone has dabbled.  But what does it actually look like when someone who builds things for a living sits down with AI tools every day and puts them to real work? Not the worldview conversation. Not the hype. The actual workflow. The shortcuts. The moment you go, "Oh my god. That completely changed how I work." In this episode of Slackers, Jaime Solis and Jonathan Sasse bring in Keegen Knapp — senior strategist, product builder, and hands-on AI practitioner — for the show’s most tactical conversation to date. Keegen has been building AI products with AI, running multi-agent loops, and rethinking what a working knowledge base looks like at the project level. This one is for the builders. Key themes include: Why Cursor is more than a code editor — and how non-developers can use it for strategy work How to build a working knowledge base using local folders, Markdown files, and context control The competitive intelligence workflow: building an agent that scrapes, synthesizes, and stores daily Synthesized executive teams and product advisory councils as AI personas that actively shape your build The Ralph Loops framework: how to run autonomous refinement cycles with human checkpoints Why GitHub is becoming the new LinkedIn — and what that means for how we signal our value The difference between curiosity-driven use and shortcut-seeking — and why it matters What a personal AI operating system looks like and why it’s closer than most people think The “spoons” framework: how creation and discovery give energy rather than drain it   Keegen walks through a concrete example — a cycling apparel startup — to show exactly how a small team would set up a shared repository, build a competitive intelligence agent, and start generating research in the background without ongoing manual effort. The workflow is more accessible than it sounds. The real barrier, as the conversation keeps returning to, is not technical fluency. It’s the willingness to be curious and to actually start. Jonathan frames the transition clearly: most people have been using AI as a super-powered search engine. The leap — to project-based context management, to building agents, to assembling virtual teams of expertise you don’t personally have — is closer than it looks. And for creatives especially, these tools don’t threaten the work. They finally give ideas somewhere to go. You don’t learn to ride a bike by reading about it. Pick a pet project. Try it one way. Abandon it. Try it a different way. The output will be completely different — and so will you. More from Keegen online: GitHub LinkedIn Grindwell.ai (golf training w/AI project) Ralph Loops (learn about this new software engineer mindset) –––The Slackers Podcast is produced by Jaime Solis and Jonathan Sasse.Audio production by Stephen Kallao.Cover art by Jonathan Sasse Connect with Jonathan & Jaime 🎙️ Jonathan Sasse — Co-Founder Tandem Studio and executive advisor.🔗 LinkedIn · Forbes Communication Council 🎙️ Jaime Solis — Music executive, Content & Media advisor, founder Red Threads newsletter.🔗 LinkedIn · Threads · Instagram Thanks for listening!If you enjoyed this episode, please follow or subscribe on your favorite podcast app and leave a quick rating or review. It helps new listeners find the show.

Most companies define competition incorrectly. They build spreadsheets comparing themselves to the businesses in their category. Same product. Same industry. Same lane. But customers do not live inside your category. They compare every experience they have across their entire life. In this episode of Slackers, Jaime Solis and Jonathan Sasse explore the idea that modern competition is horizontal, not vertical. Your real competition is not the company that sells the same thing you do. It is the experience that trained your customer to expect something better. A pizza tracker from Domino’s can reshape expectations for furniture delivery. A seamless checkout flow from Amazon can change what customers expect from healthcare portals. A well-designed Little League app can influence how someone judges enterprise software. Once customers experience transparency, speed, or simplicity somewhere else, they begin expecting it everywhere. The conversation also explores why traditional competitive analysis often misses the point. Strategy should not be limited to spreadsheets and industry comparisons. It should function as a listening device for understanding what customers are learning from the broader world of commerce. Key themes in this episode include: Why industry-based competitive analysis can create blind spots How customer expectations move horizontally across industries The Domino’s Pizza Tracker example and its ripple effects on other businesses Why benchmarking against the “low floor” of your competitors creates vulnerability How the Kano model explains the drift from delight to table stakes Why customer support teams must be part of strategic decision making The core lesson is simple. Customers compare you to the best experience they had today. Not the company that looks most like you. –––The Slackers Podcast is produced by Jaime Solis and Jonathan Sasse.Audio production by Stephen Kallao.Cover art by Jonathan Sasse Connect with Jonathan & Jaime 🎙️ Jonathan Sasse — Co-Founder Tandem Studio and executive advisor.🔗 LinkedIn · Forbes Communication Council 🎙️ Jaime Solis — Music executive, Content & Media advisor, founder Red Threads newsletter.🔗 LinkedIn · Threads · Instagram Thanks for listening!If you enjoyed this episode, please follow or subscribe on your favorite podcast app and leave a quick rating or review. It helps new listeners find the show.