ABOUT THIS PODCAST 🔗

Update frequency:
every 17 days
Average audio length:
61 minutes
English
United States
25 episodes
since Oct. 27, 2025
episodic

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Dexter Caffey grew up in Youngstown, Ohio, studied business finance at Youngstown State, and spent more than two decades in Atlanta running his own futures and options firm, managing over $100 million and hedging for Dow-level clients. Then, sitting next to a stranger at a cybersecurity event in Is…

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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 …
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 Amer…
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: …
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 chang…
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 epis…
Most organizations are not stuck because they lack talent. They are stuck because the system that got them here no longer works for where they want to go. In this episode of Slackers, Jaime Solis and Jonathan Sasse are joined by Aric Marshall, former Apple product leader and founder of ronin.ink, …
AI has leveled the production playing field. Text, images, video, wireframes. Infinite. Instant. Cheap. So what actually matters now? In this episode of Slackers, Jaime and Jonathan unpack how AI is fundamentally reshaping branding. When production becomes abundant, trust becomes scarce. And sca…
Most teams think “brand” means design. Logos. Fonts. Color palettes. A rebrand presentation. But that is not what a brand is. In this episode, Jaime and Jonathan break brand down to its simplest and most useful definition: A brand is a shortcut and a promise. The shortcut is the feeling that fires …
In this second installment of the Slackers Listener Q&A, Jaime Solis and Jonathan Sasse respond to listener questions that sit at the intersection of strategy, culture, and day to day execution. The conversation begins with a challenge many leaders face right now: separating durable trends from…
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