Slackers

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 good

Worth 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." – Jonathan

Chapters

- 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 two

Mentioned 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 Studio

Follow 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 →

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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.

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:

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.

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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:

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:

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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.

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:

The core lesson is simple.

Customers compare you to the best experience they had today.

Not the company that looks most like you.

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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 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, to unpack the mechanics of stagnation and the discipline required to create real expansion.

Aric draws from 15 years inside Apple during the development era of products like AirPods and HomePod to explain what he calls the difference between motion and purposeful progress. Busy teams can still plateau. Shipping does not equal advancement. Revenue dips are often symptoms, not root causes.

The deeper issue is usually outdated assumptions, rigid thinking, or a failure to expand capabilities beyond the original use case.

Key themes include:

• Why scaling growth is different from expansion growth

Aric introduces the “Guest Star” model as a practical framework for breaking internal echo chambers. Rather than relying solely on internal debate, organizations should bring in fractional experts to challenge assumptions and pressure-test direction.

The conversation also explores:

• How to distinguish symptoms from systemic failure

This is not a motivational conversation about pushing harder. It is a strategic conversation about re-evaluating the architecture of your system.

Because getting unstuck is rarely about urgency.

Connect with Aric on LinkedIn.

Learn more about Aric and his team at ronin.ink

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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.

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 scarcity determines value.

This conversation builds on Part 1 of the brand series and reframes brand not as logos and aesthetics, but as a cognitive shortcut. A promise. A signal in an environment overloaded with information.

Key themes include:

• Why trust increases in value as AI content explodes

Jaime and Jonathan explore how AI compresses workflows while expanding optionality. Teams can now move from whiteboard to wireframe in minutes, reducing ambiguity and improving alignment. But the real differentiator is not speed. It is taste. It is empathy. It is consistency.

They also examine the emerging labor shift, where top-tier talent equipped with AI can help smaller organizations compete with legacy Goliaths. This is not about replacing humans. It is about amplifying human judgment.

In a world of infinite content, the brands that win are the ones that stand for something specific and keep their promises over time.

Brand is not dying. It is becoming more valuable.

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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 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 someone’s mind when they see your name.
The promise is whether you consistently meet that expectation over time.

Using examples like Nike versus Hyatt, they explore why some brands feel transferable across industries while others do not. The difference is not aesthetic. It is story, identity, and trust.

The conversation moves into deeper territory:

How brands function as identity signals and tribe markers

Why founders often confuse aspiration with ability

What happens when customers define your brand before you do

Why “design spikes” are often distractions from harder strategic work

How trust becomes exponentially more valuable in an AI-saturated world

They also explore the very real risks of brand identity crises. If you do not define your brand early, the market may define it for you. And reclaiming it later can cost you your tribe.

This is Part 1 of a deeper brand series. There is more beneath the surface.

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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.

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 hype and distraction.

Using examples like AI, NFTs, and past technology cycles, the hosts introduce simple human centered filters for deciding what deserves attention. Instead of reacting to headlines, they encourage leaders to observe behavior, adoption patterns, and whether real utility is emerging beneath the noise.

The discussion then turns to remote work and distributed teams. Jaime and Jonathan argue that remote leadership is not about recreating the office at home. It requires a shift from observation to outcomes, from surveillance to trust. They share practical ways to foster connection remotely, including investing in reliable infrastructure and creating informal digital spaces where people can bond naturally.

In the final segment, the hosts address the gap between strategy and execution. Strategy is framed not as a perfect roadmap, but as a compass. Progress happens when leaders impose constraints, decide what not to do, and introduce forcing functions like deadlines and milestones that turn ideas into action.

The episode closes with a return to the guiding principle of Slackers itself. Better work comes from intentionality. Asking who the work is for, what it is for, and choosing to show up on purpose, regardless of title or role.

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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.

In this episode of Slackers, Jaime and Jonathan open the mailbag and work through listener questions pulled directly from the community. Rather than abstract frameworks, the conversation focuses on the friction leaders and operators actually experience inside growing organizations.

The episode begins with a shift away from funnel thinking toward customer journeys. Funnels prioritize internal conversion math and acceptable loss. Journeys force teams to confront what customers are thinking and feeling at each step. A key insight is that customer support teams should have a seat at the strategy table because they hold the clearest view of where journeys break down.

From there, the conversation moves into leadership tension around urgency and patience. The hosts unpack why urgency without a plan creates chaos, how companies fall into active inertia, and why teams must be clear on the destination before being asked to move fast.

They then address rebuilding trust after it has been damaged. Over explaining does not rebuild trust. Predictability does. Leaders rebuild credibility by making fewer promises and keeping all of them. In some cases, restoring trust also requires removing toxic high performers to signal that culture matters.

The episode also explores psychological safety and mental health as performance enablers rather than soft concepts. Safety is not a poster on the wall. It is defined by how leaders respond when bad news or uncomfortable truths surface.

The conversation closes with a practical collaboration model for cross functional teams. Instead of throwing work over the fence, Jaime and Jonathan propose a “crossfade” approach where teams overlap, share context, and jointly own transitions.

This is Part 1 of a multi episode listener Q&A series focused on turning leadership ideas into usable moves for better work.

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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.

Resilience fatigue is different from burnout. Burnout often comes from monotony or overuse. Resilience fatigue comes from constant adaptation. In this episode, Jonathan and Jaime unpack what happens when high performers are expected to cope indefinitely with shifting goals, unclear finish lines, and permanent urgency.

The discussion starts with a simple but uncomfortable truth. Organizations often confuse capability with capacity. High performers can usually do the work, so leaders assume they should keep doing it. Over time, these people become the ones who absorb tension, smooth chaos, and take arrows for the team. They present as steady and professional on the outside while their nervous systems quietly disengage.

The hosts introduce the idea of the “moving finish line.” Burnout looks like pounding the same nail forever. Resilience fatigue looks like running a marathon where the route keeps changing. When leadership relies on grit instead of clarity, toughness replaces planning. Heroics become the operating model.

To address this, the episode introduces the L.C.R.M. framework. Load, Capacity, Recovery, and Meaning. The framework helps teams audit whether a plan is realistic or whether it secretly depends on everyone being heroic forever. Meaning matters, but it cannot be used as a permission slip for emotional overdraft.

The episode closes with practical leadership shifts. Stop asking general questions that invite polite lies. Start asking specific questions that surface tradeoffs. Celebrate documentation, handoffs, and de escalation, not just late night saves. When leaders design for recovery and clarity, resilience stops being an emergency response and becomes sustainable.

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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.