Between Two COO's with Michael Koenig

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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 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

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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