Most organizations don't know their systems are failing until something very visible and very costly goes wrong.

In this episode of Extropy On AIr, Kevin Zirkle and Mike Jasper break down the five telltale signals of organizational entropy: exception dependency, shadow systems, decision escalation, metric conflict, and hero dependency.

The uncomfortable truth? These don't look like problems. They look like people doing their jobs. That's exactly what makes them so dangerous.

If you're a leader trying to get ahead of dysfunction before it becomes a crisis, this episode gives you a practical lens for seeing what's hiding in plain sight, and a simple place to start this week.

In this preview episode, Ravit Gutman and Mike Jasper introduce the Extropy Think Tank, a members-only community built for finance transformation practitioners who are tired of vendor pitches and ready for real conversation. No software providers. No marketing fluff. Just honest peer dialogue about what's actually working (and what isn't) as organizations navigate AI adoption, process automation, and the human side of change.

Topics are driven by the community, conversations stay in the room, and the goal is simple: connect the people who are living these challenges so they can learn from each other.

Stay tuned for more exciting news from Extropy!

Before the official launch, Ravit Gutman and Mike Jasper sit down to pull back the curtain on the Extropy Think Tank, what it is, why Extropy is the right place to host it, and what finance leaders can expect.

This isn't another product demo or vendor pitch. It's an honest, people-first space for finance transformation conversations that actually matter.

Subscribe so you don't miss what's coming!

Most enterprises believe digital transformation is a technology problem. They're wrong, and it's costing them millions.

In this episode of Extropy on AIr, Kevin Zirkle sits down with Mike Jasper, Vice President at Extropy Advisors, to dismantle one of the most expensive myths in business today: that buying better platforms leads to better outcomes.

They dig into why organizations invest heavily in automation, AI, and analytics — and still end up with teams working overtime, shadow processes, and dashboards full of green lights that mask real dysfunction. Sound familiar?

In this episode, you'll learn:

• Why technology is the amplifier, not the driver, and what happens when what you're amplifying lacks coherence
• The concept of "visible progress with invisible stagnation" and how executive reporting can reinforce the illusion
• The three most common failure patterns in digital transformation (including "fragmentation through success" — where every team wins but the company loses)
• Why the Structure → System → Technology sequence matters, and what goes wrong when organizations invert it
• Four concrete actions leaders can take right now if their transformation feels harder than it should

Building on earlier episodes, Kevin and Mike connect the dots between corporate entropy, the concept of extropy, and the deliberate design of organizational coherence — the real center of any lasting transformation.

Next episode: How entropy shows up inside finance operating models: AP, AR, procurement, and treasury. Where it hides, how it manifests, and how to start diagnosing it.

🔗 Learn more at getextropy.com

AI is everywhere right now.

But most organizations are still asking the same question:

Where do we even start?

In this episode of Extropy on Air, Mike Jasper sits down with Extropy's CEO, Ravit Gutman, to unpack what’s really happening in finance transformation after a week at the SSON conference.

Because while every solution is “AI-first,” the reality on the ground looks very different.

Leaders aren’t lacking tools. They’re lacking clarity.

We get into:

• Why so many companies feel stuck between where they are and where AI is taking them
• The gap between technology, people, and process
• What “Monday morning” actually looks like after a conference like SSON
• Key takeaways from International Women’s Day and evolving leadership expectations

And most importantly, we share a real example of what getting it right looks like.

Dexcom’s Finance Transformation Award win wasn’t about replacing people with AI, it was about using AI to support them.

Reducing overtime.
Creating space for higher-value work.
Scaling without burning out teams.

This is what happens when you focus on the human side of AI.

If you're navigating AI, finance transformation, or trying to figure out where to start, this episode brings clarity to the noise.

Most AI pilots never deliver real financial impact.

In fact, research from MIT suggests that 95% of AI pilots fail to accelerate revenue.

So what separates organizations experimenting with AI from the ones actually seeing measurable results?

In this episode of Extropy on Air, Kevin Zirkle sits down with Adam Lustig from Basware to explore what is really happening inside finance organizations as AI adoption accelerates.

The conversation highlights an important shift: moving from AI that simply generates insights to AI that actually executes work.

Together they discuss:

• Why many AI pilots stall before delivering value
• How agentic AI is transforming accounts payable operations
• Why AP is one of the most successful entry points for AI adoption
• The difference between AI that informs work and AI that performs work
• How governance enables organizations to scale AI responsibly
• The buy vs. build decision many finance leaders face when deploying AI

One theme came up again and again throughout the discussion:

Execution beats experimentation.

For finance leaders exploring AI, this episode offers a grounded look at what it actually takes to move from pilots to measurable operational impact.

As part of our International Women’s Month series, we’re bringing this powerful conversation back into the spotlight.

In this episode of Extropy on Air, Ravit Gutman sits down with Bo Senu Hodo for an honest and energizing discussion about women in finance, leadership, transformation, visibility, empathy, and what it truly takes to grow into your voice.

From navigating corporate spaces as a woman to mentoring the next generation to leading with both strength and humanity, Bo shares a perspective that is grounded, practical, and deeply empowering.

This conversation touches on:

• Women in finance and leadership
• Confidence, visibility, and finding your voice
• Mentorship, empathy, and modern leadership
• Finance transformation and process excellence
• Building strong teams and creating opportunity for others
• Why women need to stop shrinking and start being more

Bo’s message is clear: you do not have to wait to be chosen. You do not have to lead from limitation. You can be more.

If you missed this conversation the first time, we’re proud to share it again as part of our continued celebration of the remarkable women shaping our industry.

#InternationalWomensMonth #WomenInFinance #WomenInLeadership #FinanceTransformation #ExtropyOnAir

Most digital transformations do not fail because the technology is wrong. They fail because entropy wins.

In this episode of Extropy On Air, Kevin Zirkle and Mike Jasper explore the concept of entropy as the slow drift toward disorder inside growing organizations. They unpack why traditional transformation language, like automation, optimization, and modernization, often misses the deeper structural problem.

From system fragmentation and dashboard illusion to AI amplifying weak architecture, this conversation reframes transformation as intentional system design rather than tool deployment.

You will learn:

• What entropy really means in a business context
• Why scale often increases complexity faster than capability
• How AI magnifies existing structural weaknesses
• What “coherence velocity” means for leadership
• Practical steps CFOs and transformation leaders can take tomorrow

Transformation is not a project milestone. It is the continuous application of energy to maintain coherence.

If you lead finance, operations, or enterprise systems, this episode is for you.