Between Two COO's with Michael Koenig

Michael Koenig
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Between Two COOs is hosted by veteran COO Michael Koenig and brings together Chief Operating Officers, executives, and business leaders to share real insights on operations, leadership, scaling, AI, and execution. Featuring COOs from companies like LVMH, Vodafone, Automattic, Lime, JumpCloud, Grafana Labs, and Cotopaxi, plus top VCs like Brad Feld and Seth Levine. Whether you're a COO, VP of Ops, founder, or aspiring operator — this is the podcast for people who actually run companies. New episodes weekly. betweentwocoos.com | b2coos.com

  1. 7月21日

    Rick Marini on the Day-One Speech That Turned Grindr Around

    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. Why he says he is a good CEO but a great COO, and the honest question behind it: where do you add the most value? The vision gap: great CEOs see ten years out, he sees two, and the COO executes Buying Grindr for roughly $600 million after CFIUS forced the Chinese owner to sell The day-one speech: equity for everyone, transparency, and earning a burned-out team's trust Fight or flight at Tickle: the PhD-validated IQ test that turned three months of cash into the fastest-growing site on the internet Moats in the AI era: network effects plus a product people will pull out a credit card for 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) Chapters 00:00 Good CEO, great COO 00:31 Introducing Rick Marini 02:00 Where do I add the most value? 03:59 The realization and what got better 08:11 The $600 million Grindr acquisition 11:00 Day one: earning a broken team's trust 12:49 The $2 billion IPO callback 15:17 CFIUS, TikTok, and forced sales 17:37 Tickle and three months of cash 21:31 Fight or flight: the IQ test 24:23 What repeats: team, TAM, differentiation 26:51 Moats in the AI era 29:47 Grizzled vets vs rookie founders 31:49 Crypto, Rails, and perps 34:29 Waymos, AI, and what's next Mentioned in this episode Grindr Rails (confirm link before publish; press coverage cites Rails.xyz but the landing page is sparse) Protocol Ventures Waymo Connect Rick Marini on LinkedIn: https://www.linkedin.com/in/rickmarini (confirm before publish) Rick Marini on X: https://x.com/rmarini Michael Koenig on 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-with-michael-koenig/id1596195041 Spotify: https://open.spotify.com/show/4OQY2oizo3rWUlwhmtdpSi

    Rick Marini on the Day-One Speech That Turned Grindr Around

  2. 7月15日

    Zapier CEO Wade Foster on Why AI Is a People Problem, Not a Tech Problem

    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. Why Zapier has never had a COO and why Wade calls external executive hiring a coin flip Why AI sits inside the chief people officer's role at Zapier instead of a dedicated AI leader The 2023 “code red” triggered by the jump from GPT-3.5 to GPT-4 How Zapier decides when a workflow needs deterministic software versus AI judgment Why Zapier delayed its mid-market and enterprise push, and what that delay cost Advice for non-tech companies on building an AI adoption mindset without a hackathon culture 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. Mentioned in this episode Zapier — https://zapier.com Acquired podcast — https://www.acquired.fm Y Combinator — https://www.ycombinator.com Claude Code — https://claude.com/product/claude-code Zapier MCP — https://zapier.com/mcp EVE Online — https://www.eveonline.com The Hard Thing About Hard Things — https://a16z.com/books/the-hard-thing-about-hard-things/ The High Growth Handbook — https://press.stripe.com/high-growth-handbook

    Zapier CEO Wade Foster on Why AI Is a People Problem, Not a Tech Problem

  3. 7月2日

    Zulema Quintans, COO of Noda, on Why Your OKRs Don't Get Done

    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    - Episode Website: https://betweentwocoos.com/zulema-quintans-noda-ai-okrs-energy

    Zulema Quintans, COO of Noda, on Why Your OKRs Don't Get Done

  4. 6月16日

    Peter Rojas, New Products at Mozilla, on Why Ideas Don't Decide Success

    Watch on YouTube. 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 the Mozilla Pioneers program for widening the top of the funnel Why incumbents keep losing the next technology wave Why coordination breaks down at scale, and the clarity that fixes it 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: Mozilla Pioneers: https://newproducts.mozilla.org/mozilla-pioneers/ WordPress: https://wordpress.org Lovable: https://lovable.dev Replit: https://replit.com Claude Code: https://www.anthropic.com/claude-code Rec Room: https://recroom.com Connect with Peter: LinkedIn: https://www.linkedin.com/in/peterrojas/ 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.

    Peter Rojas, New Products at Mozilla, on Why Ideas Don't Decide Success

  5. 3月5日

    AI Agents Need Logins Too: Identity, Security, and the Future of AI | Greg Keller, CTO, JumpCloud

    Get 90 days of Fellow free at Fellow.ai/coo 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 SaaS, cloud infrastructure, and remote work. The discussion then turns to the next big shift: the rise of AI agents and synthetic identities inside organizations. As companies deploy more AI tools, the number of machine identities may soon outnumber human employees. Managing what those systems can access will become a critical security and operational challenge.   Topics Covered 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.   AI, Security, and Synthetic Identities 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.   Key Takeaway 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. The companies that manage identity well will move faster and operate more securely.   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

    AI Agents Need Logins Too: Identity, Security, and the Future of AI | Greg Keller, CTO, JumpCloud

  6. 1月28日

    Seth Levine of Foundry Group on Capital Evolution, AI, and the Future of Company Leadership

    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 What we coverWhy Seth wrote Capital Evolution and why nowWhy today’s economic shift is structural, not cyclicalHow power has moved from public institutions to businessesWhat companies are being asked to carry that they weren’t built forHow AI fits into this broader realignmentEarly signals that companies are adapting well to AIWhat strong executive teams do differently during uncertaintyCommon leadership traps when change happens too fastA real crisis from a portfolio company and what the executive team did wellThe new leadership muscle operators need for the next decadeEpisode Chapters / Timestamps00:00 – 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

    Seth Levine of Foundry Group on Capital Evolution, AI, and the Future of Company Leadership

  7. 1月20日

    Brad Feld On The Emotional Operating System of Great Leaders and Giving First

    Get Brad's new book, Give First. 00:00 — Cold open: “Something new is f****d 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

    Brad Feld On The Emotional Operating System of Great Leaders and Giving First

  8. 10/12/2025

    AI, Fraud, and the Next Era of Commerce with Peter Dougherty, President of Spreedly

    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 presidencyThe “right person, right problem” frameworkOne-way vs two-way doors for staffing big problemsHow to scale a GTM org from $20M to $100MWhy open payments replaces orchestrationSpreedly’s unique market position and 15-year head startAgent to agent commerce and Google’s new payments protocolHow AI changes the velocity of money movementFraud orchestration and Spreedly’s acquisition of DodgeballBalancing profitable growth vs growth at all costsPerception vs reality in leadershipPeter’s wildest “I never thought I’d see that” story

    AI, Fraud, and the Next Era of Commerce with Peter Dougherty, President of Spreedly
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Between Two COOs is hosted by veteran COO Michael Koenig and brings together Chief Operating Officers, executives, and business leaders to share real insights on operations, leadership, scaling, AI, and execution. Featuring COOs from companies like LVMH, Vodafone, Automattic, Lime, JumpCloud, Grafana Labs, and Cotopaxi, plus top VCs like Brad Feld and Seth Levine. Whether you're a COO, VP of Ops, founder, or aspiring operator — this is the podcast for people who actually run companies. New episodes weekly. betweentwocoos.com | b2coos.com

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