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 now that AI lets anyone stand up a company in a weekend.

Rick Marini has founded and operated consumer technology companies for 26 years. He co-founded Tickle in 1999, founded and led BranchOut to 800 million profiles and $49 million raised, and served as COO of Grindr from its 2020 acquisition through its $2 billion NYSE debut. He has been an angel investor in 60 companies, 15 of them unicorns, started Protocol Ventures, the first crypto fund of funds, and is now co-founder of Rails, a crypto perpetuals exchange.

Read more and explore related coverage at betweentwocoos.com/rick-marini-good-ceo-vs-great-coo. (update if slug changes)

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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 organizational and people problem rather than a technology problem. The conversation covers Zapier's “code red” response to GPT-4, the pricing decision that traded short-term revenue for long-term customer trust, and what changed in Wade's own leadership style over 14 years in the same seat.

Wade Foster co-founded Zapier and serves as its CEO. Zapier is a workflow automation platform that connects thousands of software tools and now powers billions of automated actions each month. Under Wade's leadership, Zapier grew to roughly 850 employees and a multi-billion dollar valuation while raising only a small seed round after Y Combinator.

Read the full episode page at Between Two COOs: Wade Foster on why AI adoption is a people problem.

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 behind it

- Being directive without micromanaging

- The $200 billion commercial buildings spend on energy, and how much is wasted

- How Noda connects to legacy buildings and cleans messy data

- Automated demand management, and the knob that quietly saves energy

- Why AI makes this a golden age for operators

- Where the human still has to stay in the loop

Chapters

00:00  Cold open: the energy waste problem

01:05  Meet Zulema and Noda

01:45  From Juilliard ballet to COO

03:30  Holding focus and flexibility

06:01  Why OKRs fail, and the 70% rule

08:41  Top-down meets bottom-up OKRs

13:09  Making OKRs the operating system

15:55  Inside Noda: climate tech for buildings

19:19  Turning messy building data usable

20:39  The modular path to automation

22:50  AI cuts onboarding from weeks to hours

24:50  The Buildings IoT acquisition

25:46  AI, the COO role, and human judgment

32:09  The five-year view for buildings

34:42  A warehouse full of sensors

About Zulema:

Zulema Quintans is the chief operating officer of Noda, an energy and building intelligence platform for commercial real estate, where she leads product, operations, and customer success. Before Noda she held leadership roles at Arcadia, American Express, and Bain & Company. She began her career as a professional ballet dancer trained at Juilliard.

Resources mentioned:

- Roger Federer, 2024 Dartmouth commencement address: https://www.youtube.com/watch?v=pqWUuYTcG-o

Connect with Zulema:

- LinkedIn: https://www.linkedin.com/in/zulema-quintans-36152223/

- Noda: https://noda.ai

Connect with Michael:

- LinkedIn: https://www.linkedin.com/in/michael-koenig514

- Building Helm: https://helmapp.ai

Subscribe to Between Two COOs:

- Apple Podcasts: https://podcasts.apple.com/us/podcast/between-two-coos/id1635533318

- Spotify: https://open.spotify.com/show/2NjVgGm6mqLPEbJUvHnHEH

- Newsletter: https://betweentwocoos.com   

Watch on YouTube.

In this episode, Peter and Michael discuss:

About Peter: Peter Rojas co-founded Gizmodo and Engadget, two publications that changed how people understand technology. He has been an operator and investor across AOL, Meta, and BetaWorks, where he was a founder and VC. Today he leads new product development at Mozilla and runs Mozilla Pioneers.

00:00 Cold open

01:46 The email that started the show

03:33 Startup vs building inside a company

06:57 The corporate product numbers game

11:03 Vibe coding and Mozilla Pioneers

15:13 When a trusted brand is the advantage

18:04 Why incumbents lose the next wave

21:58 Meta's metaverse bet vs AI

25:44 If I were running Meta

29:02 Was the VR bet a failure

30:27 Why coordination breaks at scale

35:07 Fear, focus, and the CEO filter

38:56 How Mozilla runs on KPIs

40:30 The founder who hid his idea

46:33 Where to find Peter

Resources mentioned:

Connect with Peter:

Connect with Michael:

Subscribe to Between Two COOs:

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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.

What a CTO actually does

Greg explains the different types of CTO roles and how technology leaders help companies anticipate where the market is headed.

Identity Access Management explained simply

IAM answers three core questions inside every company:

Who are you?

What can you access?

How is that access managed?

Why the old IT model broke

Traditional identity systems were built for on-premise offices and Microsoft infrastructure. Modern companies now operate across:

SaaS applications

cloud infrastructure

remote work environments

multiple operating systems

How JumpCloud approaches identity

JumpCloud was built to manage identity across devices, applications, and infrastructure regardless of platform.

Where Okta fits in the ecosystem

Okta helped modernize browser-based authentication through Single Sign-On, while JumpCloud focuses on broader identity infrastructure.

Why COOs should push AI adoption

Greg argues AI adoption is no longer optional. Companies must encourage teams to improve productivity and efficiency using AI.

The rise of synthetic identities

AI agents, bots, APIs, and service accounts are becoming new actors inside companies that require identity governance.

Bots may soon outnumber employees

Organizations will soon manage more machine identities than human ones.

AI as a potential insider threat

AI systems can become security risks if they are granted excessive permissions or misinterpret policies.

The API key governance problem

Many AI integrations rely on API keys, which are often poorly managed and can create hidden security risks.

As companies adopt AI, identity access management becomes the control layer that determines what both humans and machines are allowed to do inside the organization.

Links:

Michael on LinkedIn: https://linkedin.com/in/michael-koenig514

Greg on LinkedIn: https://www.linkedin.com/in/gregorykeller/

JumpCloud: https://jumpcloud.com/

Between Two COO’s: https://betweentwocoos.com

Episode Link: https://betweentwocoos.com/ai-agents-identity-access-greg-keller

Get 90 Days of Fellow's incredible AI notetaker for free at fellow.ai/coo

Guest: Seth Levine

Book: Capital Evolution

Podcast: Between Two COOs

Host: Michael Koenig

• 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 into this broader realignment
• Early signals that companies are adapting well to AI
• What strong executive teams do differently during uncertainty
• Common leadership traps when change happens too fast
• A real crisis from a portfolio company and what the executive team did well
• The new leadership muscle operators need for the next decade

00:00 – Introduction

01:40 – Seth’s 30-second pitch for Capital Evolution

04:05 – Why this shift is structural, not cyclical

07:20 – What’s broken in the current economic model

11:00 – The power shift from government to business

15:10 – What leaders are quietly losing

18:45 – Where AI fits into this realignment

23:30 – What boards see when AI adoption works

28:05 – How strong executive teams handle uncertainty

33:40 – Leadership traps during rapid change

38:10 – A crisis inside a portfolio company

44:00 – The new muscle operators must build

48:50 – A moment Seth never thought he’d see

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 long games

13:00 — Does giving create outcomes, or just energy?

16:00 — Why Brad writes books: longform thinking as meaning-making

20:00 — Searching for meaning through mentorship and reflection

23:00 — “I hate the phrase pattern recognition” — mentorship done right

28:00 — The power dynamic between founders and mentors

32:00 — Management through commitment, not control

35:00 — Agile as an operating system for accountability

38:00 — Emotional intelligence and the role of executive coaches

41:00 — Mentor vs. coach vs. therapist vs. advisor

45:00 — Trust as the foundation of all high-leverage relationships

47:30 — Wild story: when the second floor of Sphero’s building collapsed

52:00 — “They can’t kill you and they can’t eat you” – Len Fassler’s advice

55:00 — Closing thoughts on being the Bill Murray of venture capital

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 focus and role separation, and how to keep silos aligned around one customer story.

Peter also explains the shift from “payments orchestration” to “open payments” and how Spreedly’s position as the original player in the space gives them unique leverage. We walk through the future of agentic commerce, Google’s new agent-to-agent payments protocol, and what it means when agents can transact faster than any human could ever shop.

We close out with the Dodgeball acquisition, a primer on fraud orchestration, and a wild story about working an entire night shift at a nightclub during a meltdown launch.

Topics Covered:

• How Peter defines the journey to presidency
• The “right person, right problem” framework
• One-way vs two-way doors for staffing big problems
• How to scale a GTM org from $20M to $100M
• Why open payments replaces orchestration
• Spreedly’s unique market position and 15-year head start
• Agent to agent commerce and Google’s new payments protocol
• How AI changes the velocity of money movement
• Fraud orchestration and Spreedly’s acquisition of Dodgeball
• Balancing profitable growth vs growth at all costs
• Perception vs reality in leadership
• Peter’s wildest “I never thought I’d see that” story

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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 those lessons translate to running a modern SaaS organization and why purpose, process, and payoff are the anchors of any good meeting.

They dig into:

• How government discipline shaped Harris’s operating style
• The “three P’s” framework for productive meetings
• Why decision speed is overrated — and what Harris means by “Did anyone die or go to jail?”
• What he learned from executive coaching and board feedback
• How GuideCX built a new product category around customer onboarding
• How AI is quietly reshaping how he manages teams and prepares communications
• Why calm is a competitive advantage during crisis moments like SVB

Michael also gives context at the top: this episode was recorded across two sessions, after a recording issue mid-interview (and yes, he’s now officially a Riverside convert).

It’s a conversation about building trust, running tight systems, and keeping your head when everything around you is changing.

Harris Clarke on LinkedIn
GuideCX

Michael Koenig on LinkedIn

Between Two COO's Website

Episode Website

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 muscle of strategy execution.

She explains how to create an “operating rhythm” that keeps teams aligned across time zones, the tension between governance and red tape, and how Cascade helps leaders link vision to measurable execution.

The conversation dives deep into AI’s role in operations, the future of hybrid work, and what it takes to move from chaos to clarity in a global startup.

Anna’s storytelling — especially her account of leading through Superstorm Sandy — highlights what real-time operational leadership looks like when everything goes sideways.

Timestamps

00:00 – Intro & sponsor

01:00 – The chaos of Superstorm Sandy

02:00 – Anna’s journey: from theater to tech

06:00 – The making of a generalist

10:00 – Joining Cascade and fixing retention

11:00 – Creating a “working rhythm”

14:00 – Governance vs. red tape

17:00 – The 5 pillars of strategic maturity

19:00 – Turning strategy into execution

24:00 – How Cascade uses AI internally

28:00 – OKRs, KPIs, and strategy frameworks

33:00 – Who owns strategy?

36:00 – Rebuilding a business overnight

43:00 – Closing thoughts

Between Two COO's - https://betweentwocoos.com 

Episode Website - https://betweentwocoos.com/anna-elwood-coo-cascade

Anna Elwood on LinkedIn - https://www.linkedin.com/in/annaelwood

Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514