Between Two COO's with Michael Koenig

Michael Koenig
  • 5.0 (11)
  • Management
  • Updated Biweekly

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. Sep 30

    Tom Masterson, Deep Genomics COO on AI Drug Discovery That Learned the Rules

    Tom Masterson, COO of Deep Genomics, on AI drug discovery where precision beats creativity. He explains how the company's siRNA model picked an approved cholesterol drug out of 3,500 candidates for a target it had never seen, why it designs toxic molecules on purpose, and how a COO runs a company where the lab and the software move on different clocks. In this episode, Tom and Michael discuss: The difference between life sciences and healthcare, and where a tech bio company fitsBrendan Frey, Geoffrey Hinton's lab, and a thesis that was right but earlyRetiring 40 task-specific models when a foundation model beat themLab in the loop, and why the best training data includes molecules designed to be toxicThe siRNA result: a target the model had never seen, and nine picks out of 3,500Why drug developers think in 10 years and machine learning teams think in an afternoonFrom chief of staff to COO, and getting scientists to adopt processRunning waterfall and agile side by side, on a quarterly board and advisor rhythmThe N-of-one problem: a hero to the world, or a hero to your shareholdersAbout Tom:Tom Masterson is chief operating officer of Deep Genomics, the Toronto company building biological foundation models for RNA drug discovery. He joined in business development and strategy, then served as chief of staff to founder Brendan Frey and to CEO Brian O'Callaghan before becoming COO. He partners with the CEO on board and investor relations, owns the company's project management and executive functions, and is the person who turns Deep Genomics' science into its business story. Before Deep Genomics he was the first employee at Microbiome Insights in Vancouver, worked in contract research and healthcare design strategy, and founded Caregiver Support, a startup that helped family caregivers through medical crises. He started his career selling dental lasers at a medical device company. He holds a BSc in cell biology and genetics from the University of British Columbia and an MBA from Harvard Business School. Resources mentioned: Deep Genomics: https://www.deepgenomics.comGenomeKit (open source): https://github.com/deepgenomics/GenomeKitAlnylam Pharmaceuticals: https://www.alnylam.comModerna: https://www.modernatx.comMerck: https://www.merck.comBroad Institute: https://www.broadinstitute.orgConnect with Tom: LinkedIn: https://www.linkedin.com/in/mastersonthomas/Connect with Michael: LinkedIn: https://www.linkedin.com/in/michael-koenig514Building Helm: https://helmapp.aiSubscribe to Between Two COOs: Apple Podcasts: https://podcasts.apple.com/us/podcast/between-two-coos-with-michael-koenig/id1596195041Spotify: https://open.spotify.com/show/4OQY2oizo3rWUlwhmtdpSiNewsletter: https://betweentwocoos.com

    Tom Masterson, Deep Genomics COO on AI Drug Discovery That Learned the Rules

  2. Sep 22

    The AI Bubble Has a Due Date. It's 2029 | Paul Kedrosky, SK Ventures

    Paul Kedrosky of SK Ventures says AI capex is driving up to 70 percent of US GDP growth, and most of it is now borrowed. He walks through the money map, the 2029 maturity wall, why AI tokens are a deflationary commodity, and three ways the AI bubble reaches companies that never touch a data center. In this episode, Paul and Michael discuss: Why AI capex now accounts for 30 to 70 percent of US GDP growth, and the historical moments that looked the sameThe money map: how the buildout moved from hyperscaler cash flow to more than 60 percent external financingThe 2029 maturity wall, and why it rhymes with the mortgage resets of the financial crisisTokens as the first hyper-deflationary industrial commodity, and the growth math that followsWhy developers are a misleading signal for how the rest of the economy will use AICircular financing: when one company is customer, supplier, investor, and lender at onceWhether anyone is safe building on top of the frontier models, and what quant funds do insteadThree things operators should do now: guard your signal, vet your vendors, and stop extrapolating from codersAbout Paul:Paul Kedrosky is co-founder and managing partner of SK Ventures and a fellow at MIT’s Initiative on the Digital Economy, where his research focuses on AI and the future of work. A former Wall Street technology equity analyst, he consults with major asset managers, is a regular contributor at CNBC and Bloomberg, and co-hosts a weekly show with former Twitter CEO Dick Costolo. Resources mentioned: Paul Kedrosky: https://paulkedrosky.comMIT Initiative on the Digital Economy: https://ide.mit.eduNational Bureau of Economic Research: https://www.nber.orgCoreWeave: https://www.coreweave.comHudson River Trading: https://www.hudsonrivertrading.comJane Street: https://www.janestreet.comStratechery by Ben Thompson: https://stratechery.comConnect with Paul: LinkedIn: https://www.linkedin.com/in/paul-kedrosky/Newsletter: https://paulkedrosky.comConnect with Michael: LinkedIn: https://www.linkedin.com/in/michael-koenig514Building Helm: https://helmapp.aiSubscribe to Between Two COOs: Apple Podcasts: https://podcasts.apple.com/us/podcast/between-two-coos-with-michael-koenig/id1596195041Spotify: https://open.spotify.com/show/4OQY2oizo3rWUlwhmtdpSiNewsletter: https://betweentwocoos.com

    The AI Bubble Has a Due Date. It's 2029 | Paul Kedrosky, SK Ventures

  3. Sep 16

    Lior Eldan, Moburst COO on Reinventing the Marketing Agency Before AI Eats It

    Lior Eldan, co-founder and COO of Moburst, has reinvented what his agency sells three times, from app store optimization to AI products. He explains why replacing people with AI is backwards, why managers have to do the work, and why automating a broken process just gets the AI blamed. In this episode, Lior and Michael discuss: Why Moburst has moved off its winning product three times since 2013, and what each move brokeBuild vs. buy for services: why an acquisition brings a founder, and what the day after actually looks likeManagers do the work: the rule that keeps middle management from becoming a layer of measurersWhy replacing people with AI is backwards, and what Moburst now requires of every junior hireForward-deployed: what an embedded team found inside a mortgage company's operationsAnswer engine optimization and why an LLM reads your whole digital footprint, not your websiteFix the process before you automate it, and the cadence underneath a company that keeps reinventing itselfAbout Lior:Lior Eldan is co-founder and COO of Moburst, the digital marketing agency he started in 2013 with Gilad Bechar after the two met as HR officers in the Israeli army. Moburst began in app store optimization, grew through acquisitions including Uproar and Kitcaster, and now sells AI products alongside its services. Adweek has named it one of the fastest-growing agencies in the world. Resources mentioned: Moburst: https://www.moburst.comKitcaster: https://kitcaster.comHubSpot: https://www.hubspot.comSupercell: https://supercell.comClaude Code: https://claude.com/product/claude-codeTucows: https://tucows.comConnect with Lior: LinkedIn: https://www.linkedin.com/in/lioreldan/Connect with Michael: LinkedIn: https://www.linkedin.com/in/michael-koenig514Building Helm: https://helmapp.aiSubscribe to Between Two COOs: Apple Podcasts: https://podcasts.apple.com/us/podcast/between-two-coos-with-michael-koenig/id1596195041Spotify: https://open.spotify.com/show/4OQY2oizo3rWUlwhmtdpSiNewsletter: https://betweentwocoos.com

    Lior Eldan, Moburst COO on Reinventing the Marketing Agency Before AI Eats It

  4. Aug 18

    Joe Yaffe, COO at Cowboy Space, on Whether Data Centers in Space Are Cheaper

    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 right to raise the billions this needs beyond the first $365 million Why the perfect rocket engine is designed to sit on the balance point of failure How being your own only customer changes what a failed launch costs you Six-year chip life, and why you stop caring that you can't reach them The seven-year wait for a data center in Northern Virginia Which agencies regulate an orbital data center, including the FDA Why hiring, not physics, sits at the top of his list The December 2028 launch date the whole company runs against About Joe: Joe Yaffe is COO and chief legal officer at Cowboy Space, which is building data centers that run in orbit. He spent 31 years practicing law in Silicon Valley, fifteen of them at Latham & Watkins and the rest at Skadden, where he was managing partner of the Palo Alto office. He studied ancient Greek in college. Connect with Joe: LinkedIn: https://www.linkedin.com/in/josephyaffe/ 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-with-michael-koenig/id1596195041 Spotify: https://open.spotify.com/show/4OQY2oizo3rWUlwhmtdpSi Newsletter: https://betweentwocoos.com

    Joe Yaffe, COO at Cowboy Space, on Whether Data Centers in Space Are Cheaper

  5. Aug 11

    Joe Yaffe (Cowboy Space): From Big Law to Orbit, Part 1 of 2

    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 lasers. In this episode, Joe and Michael discuss: Why switching law firms counted as a midlife crisis, and what that says about risk The three traits Joe saw in every successful founder across 31 years of client work The easy button for a lawyer, and why he calls it second grade lawyering One way doors and two way doors, with a real one from Cowboy Space Getting to an undergraduate understanding of rocket science in about a year How data centers in space actually work, explained without an engineering degree Why the second stage of the rocket becomes both the data center and the radiator Why none of it breaks the laws of physics About Joe: Joe Yaffe is COO and chief legal officer at Cowboy Space, which is building data centers that run in orbit. He spent 31 years practising law in Silicon Valley, fifteen of them at Latham & Watkins and the rest at Skadden, where he was managing partner of the Palo Alto office. He studied ancient Greek in college. Chapters 00:00 Cold open 01:11 Introduction 02:27 Thirty-one years, and a very small midlife crisis 04:03 Meeting Baiju Bhatt 05:13 "I thought I would die at my desk" 05:31 Space lasers 06:34 "If you do it, I'll come join you" 07:32 What twenty years beside founders teaches you 09:13 The eight billion people rule 11:46 Second grade lawyering 13:26 Tapping the brakes and hitting the accelerator 14:33 One way doors and two way doors 17:14 "Be careful with the rations" 18:13 Zero to rocket science in a year 19:45 "I'm the liberal arts guy in the room" 22:03 Acronyms, and blowing a fastball by you 23:27 Advice for anyone standing at the fork 26:37 The best advice he got before he jumped 29:29 How Cowboy Space works, explained for the rest of us 31:05 Asimov wrote about this in the 1940s 35:27 Turning the second stage into the data center 36:30 The radiator epiphany 37:50 Cheaper than Earth, or it's a science project 39:29 Why they're building their own rocket 43:54 Chips, cooling, and NVIDIA 45:54 "We're not breaking any laws of physics" 47:50 Four companies at once 50:37 Nuclear reactors on the moon Resources mentioned: Cowboy Space: https://cowboyspace.com I, Robot by Isaac Asimov, which collects "Reason", the 1941 short story on beaming power from orbit: https://www.amazon.com/dp/055338256X Connect with Joe: LinkedIn: https://www.linkedin.com/in/josephyaffe/ 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-with-michael-koenig/id1596195041 Spotify: https://open.spotify.com/show/4OQY2oizo3rWUlwhmtdpSi Newsletter: https://betweentwocoos.com

    Joe Yaffe (Cowboy Space): From Big Law to Orbit, Part 1 of 2

  6. Jul 29

    Riikka Söderlund, Katana COO, on Why AI Won't Know Your Product Exists

    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 of quarters, why Katana opened its API while SAP closed theirs, and the brand that discovered it had been selling at a loss. Why marketing is an underrated path to the COO seat, and what narrative building does for an operator that sales training does not The six-week sprint, why four weeks is too short and eight is too long, and how she bridges the gap between a key result and an actual plan of execution Product metadata as the new SEO, and why an out-of-stock product does not get surfaced by AI search at all The Shopify earnings-call number: AI referral traffic to Shopify stores grew 13-fold quarter over quarter Why Katana opened its API to any AI the customer chooses while SAP closed theirs, and why she frames that as a values choice about who owns inventory data The brand that did not know its cost of goods sold was negative, and the one that found $40,000 of inventory it had misplaced Riikka Söderlund is the chief operating officer at Katana Cloud Inventory, where she runs the commercial side of the business. She spent two decades in marketing, starting in Helsinki ad agencies, then a decade in consumer marketing, before joining Katana as VP of marketing and later CMO. She studied communications, and she credits narrative building as the skill that carried across from marketing into operations. Katana serves merchants in over 70 countries, with more than $3 billion in gross merchandise value flowing through the platform. Chapters 0:00 Cold open 1:04 Introducing Riikka Söderlund and Katana 2:12 From Helsinki PR to Vogue and Oprah 3:55 Why old-era marketing skills became rare 6:05 What COOs should learn from marketers 7:24 Storytelling, listening, and internal communication 10:37 Founder gravitas versus learned operator skill 11:53 Training to be a COO before the title 14:15 Running Katana day to day 15:22 Goal setting and the six-week sprint 19:16 Physical goods, SAP, and the market gap 25:01 The golden era of creativity and branding 30:35 Product metadata is the new SEO 33:44 AI search and the internet economy 36:33 Opening the API while SAP closed theirs 38:06 Training for product management 42:02 The brand that didn't know it was losing money 43:43 Harry Potter and the invisible inventory Mentioned in this episode Katana Cloud Inventory: https://katanamrp.com Shopify: https://www.shopify.com SAP: https://www.sap.com Salesforce: https://www.salesforce.com Gong: https://www.gong.io Lovable: https://lovable.dev Claude Code: https://claude.com/product/claude-code Cannes Lions: https://www.canneslions.com Connect with Riikka LinkedIn: https://www.linkedin.com/in/riikkasoderlund/ Katana Cloud Inventory: https://katanamrp.com 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-with-michael-koenig/id1596195041 Spotify: https://open.spotify.com/show/4OQY2oizo3rWUlwhmtdpSi Newsletter: https://betweentwocoos.com

    Riikka Söderlund, Katana COO, on Why AI Won't Know Your Product Exists

  7. Jul 21

    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

  8. Jul 15

    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
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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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