Between Two COO's with Michael Koenig

Part 2 of 2. Part 1 is here: https://betweentwocoos.com/65

In part 1, Joe Yaffe explained how an orbital data center works. This time, the question is
whether it works as a business.

In this episode, Joe and Michael discuss:

• Why Cowboy Space measures itself in cost per GPU hour, not cents per kilowatt hour
• Why a lot of new space companies are run by technologists who aren't asking if it's a business
• What has to go righ...

Part 1 of 2. Part 2 drops later this week.

Joe Yaffe had climbed as high as the ladder goes. Fifteen years at Latham & Watkins,
then Skadden, managing partner of the Palo Alto office, 31 years advising founders and
CEOs. By his own account, his idea of a midlife crisis was moving from one mega law firm
to another. Then Baiju Bhatt stepped away from Robinhood, Joe asked what was next, and
the answer was space...

Riikka Söderlund is the chief operating officer at Katana Cloud Inventory, a Finland-based platform that helps small product businesses run inventory, manufacturing, and multi-channel sales. She and host Michael Koenig discuss how AI search is affecting product discovery, why an out-of-stock product is invisible to an AI chat, and why she thinks marketing is an underused path to the COO seat. Along the way: six-week sprints instead...

Rick Marini, co-founder of Rails and former COO of Grindr, joins Between Two COOs to explain why he would rather be a great COO than a good CEO. He and host Michael Koenig cover the CFIUS-forced sale that put Grindr in play, the day-one culture reset that ended two and a half years later in a $2 billion New York Stock Exchange debut, the three-months-of-cash pivot that saved Tickle in the dot-com crash, and how he evaluates moats n...

Michael Koenig talks with Wade Foster, co-founder and CEO of Zapier, about running the company for 14 years without a CEO safety net and without ever naming a COO. Wade explains why he thinks hiring a chief operating officer from outside a company is a coin flip, why Zapier put AI transformation inside the chief people officer role instead of naming a dedicated AI executive, and why he believes AI adoption is fundamentally an organ...

Zulema Quintans runs operations at an energy company, and she has a clear theory about why goals fail. This is a conversation about making OKRs actually work, and how AI is changing the operator's job.

In this episode, Zulema and Michael discuss:

- Why most OKRs never get done, and the one link that fixes it

- Running OKRs as an operating system, not a quarterly ritual

- Aiming for 70 percent completion, and the Federer mindset beh...

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Peter Rojas has built new things at almost every scale there is, and he planted the seed for this show years ago in an email to Michael.

In this episode, Peter and Michael discuss:

• How building new products inside a big company differs from a startup, and why you have to invest ahead of traction
• Why corporate product development is a harder numbers game than a venture portfolio
• AI, vibe coding, and th...

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In this episode, Michael Koenig speaks with Greg Keller, co-founder and CTO of JumpCloud, about identity access management and why it’s becoming one of the most important operational systems in the age of AI.

Greg explains how traditional identity systems were designed for office-based companies running Microsoft infrastructure and why that model broke as companies moved to Sa...

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Guest: Seth Levine

Book: Capital Evolution

Podcast: Between Two COOs

Host: Michael Koenig

What we cover

• Why Seth wrote Capital Evolution and why now
• Why today’s economic shift is structural, not cyclical
• How power has moved from public institutions to businesses
• What companies are being asked to carry that they weren’t built for
• How AI fits int...

Get Brad's new book, Give First.

00:00 — Cold open: “Something new is fucked up in my world every day”

02:00 — The Yoda t-shirt story + the mythology of Brad Feld

04:00 — “Give First” vs. “Pay it Forward”: philosophy, not obligation

07:00 — Why giving isn’t altruism — and how it works in complex systems

10:00 — Positive-sum vs. zero-sum: tennis, trust, and lon...

This episode goes deep into the mechanics of scaling a company from steady growth to breakout velocity. Peter shares how Spreedly quadrupled ARR growth in his first year without increasing OPEX, why the “right people pointed at the right problems” is everything, and how to decide which problems are existential versus learn-as-you-go.

We dissect how go-to-market organizations evolve from $20M to $100M ARR, the power of fo...

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This week on Between Two COOs, Michael sits down with Harris Clarke, COO at GuideCX, to talk about what steady leadership actually looks like inside fast-changing companies.

Harris started his career in protocol and operations for the U.S. Department of State, where “process” wasn’t just a buzzword — it was survival. He shares how tho...

From Zocdoc to Cascade, COO Anna Elwood breaks down the systems, rhythms, and AI tools that turn chaos into execution.

In this episode of Between Two COOs, Michael sits down with Anna Elwood, COO of Cascade, the strategy-execution platform helping companies turn plans into results.

Anna shares how she evolved from Broadway actor to operator, scaling companies like Zocdoc, Knotel, and Teachable before joining Cascade to build the musc...

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Guest: Lance Willett, Chief Quality Officer at Automattic

Topics Covered:

• How Automattic’s open source culture evolved over 20 years
• What a Chief Quality Officer actually does—and why it matters
• Quality = Craft × Context, and how that feedback loop scales
• Automattic’s AI strategy: support bots, contextual UI, and site generation
• The importance of tools l...

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Why Linda still codes on weekends — and what it teaches her about the future of AI (6:00)

How AI is changing what Webflow builds — and how fast they build it (3:30–13:00)

What happens when websites are no longer built just for humans (14:00)

The rise of AEO (Answer Engine Optimization) and what it means for ops (17:00–21:00)

Favorite LLMs and workflow...

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In this episode, Doug and I cover:

• Why “AI agent” is more than just a buzzword
• The difference between deflection and resolution in AI-powered support
• How Kustomer structures RevOps, GTM, and forecasting
• What it means to operate with high-context vs. generic playbooks
• How Doug thinks about team structure, ownership, and cross-functional clarity
• Predictions for a...

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Key Takeaways:

RevOps aligns and optimizes sales, marketing, and customer success, ensuring efficient and sustainable growth.

Effective RevOps requires balancing strategic planning, data-driven analytics, and tactical execution.

Successful RevOps integration hinges on clear communication, cultural alignment, and strategic hiring decisions.

AI is poised to signi...

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Timestamps:

(02:00) Fellow’s shift from productivity tool to AI assistant.

(07:00) Implementing large-scale organizational change.

(13:00) Managing change and internal communications.

(20:00) Moving toward an agentic, automated workflow future.

(23:00) Unexpected real-world AI uses at Fellow.

(29:00) Privacy, security, and enterprise-grade compliance.

(33:00) Selecting a...

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AI and Privacy: Navigating the EU's New AI Act with Flick Fisher

In this episode of Between Two COOs, host Michael Koenig welcomes back Flick Fisher, an expert on EU privacy law. They dive deep into the newly enacted EU Artificial Intelligence Act and its implications for businesses globally. They discuss compliance challenges, prohibited AI practices, and the potential ...