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

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 [https://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 [https://linkedin.com/in/michael-koenig514] Greg on LinkedIn: https://www.linkedin.com/in/gregorykeller/ [https://www.linkedin.com/in/gregorykeller/] JumpCloud: https://jumpcloud.com/ [https://jumpcloud.com/] Between Two COO’s: https://betweentwocoos.com [https://betweentwocoos.com] Episode Link: https://betweentwocoos.com/ai-agents-identity-access-greg-keller [https://betweentwocoos.com/ai-agents-identity-access-greg-keller]

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 [https://fellow.ai/coo] Guest: Seth Levine [http://sethlevine.com/] Book: Capital Evolution [https://www.amazon.com/Capital-Evolution-New-American-Economy/dp/1637747780] Podcast: Between Two COOs [https://betweentwocoos.com] Host: Michael Koenig [https://linkedin.com/in/michael-koenig514] 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 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 EPISODE CHAPTERS / TIMESTAMPS 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

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

Get Brad's new book, Give First [https://www.amazon.com/Give-First-Mentorship-Brad-Feld/dp/1646871324]. 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

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 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

The Power of Calm: GuideCX COO Harris Clarke on Building Trust and Systems That Hold

Get 90 Days of Fellow's AI Meeting Assistant FREE at fellow.ai/coo [https://fellow.ai/coo]   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 [https://www.linkedin.com/in/harris-clarke-26605946/] GuideCX [http://guidecx.com/] Michael Koenig on LinkedIn [https://linkedin.com/in/michael-koenig514 ] Between Two COO's Website [https://betweentwocoos.com ] Episode Website [https://betweentwocoos.com/harris-clarke-guidecx ]