The CTO Playbook

• 68: Startups, AI, and the Funding Reset: What Investors Really Want in 2025

  Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.What if the future of startups isn’t decided by who builds the flashiest AI, but by who solves the right problems?In this episode, I’m joined again by my friend Thorgeir Einarsson, almost a year since we last spoke, to unpack how AI funding and investor expectations have shifted from hype cycles to hard realities. Thor runs PGO, a service that helps founders get truly investment-ready with real pre-diligence instead of lipstick on a pig.Pre-seed and seed are brutal right now, and traction beats vibes. Investors are placing smaller, option-like bets at the AI application layer while steering clear of generic models. Hardware is back where it matters, from defense tech to medical devices, when firmware and software meet close to the metal. We trace the PE-ification of VC: rolling up vertical SaaS, “AI-firing” them, and rebuilding moats from customer bases and domain data. Thor flags a blind spot worth building for: AI safety and guardrails for agentic workflows. Then we get practical: preparation beats performative decks, checklist-driven pre-diligence forces the hard questions, and the playbook is simple… know yourself, know your co-founders, keep investors updated, and track the numbers.You’ll Learn:The reason many VCs focus on the AI application layerWhat happens when nobody knows what a great AI company looks like yetThe link between defense and medical devices and hardware-plus-software productsThe damage of skipping investor updates and simple monthly KPIsWhat it feels like to raise when only one to three percent get a checkThe reason pre-diligence and checklists come before the pitchWhat happens when agentic workflows scale without safety guardrailsTimestamps:[00:00] Introduction[05:42] Why AI investment has shifted from hype to hard reality[12:18] The brutal truth about pre-seed and seed fundraising in 2025[18:33] Why investors are betting smaller at the AI application layer[25:47] How defense tech and medical devices are bringing hardware back[32:11] The rise of “AI-firing” old SaaS companies and the PE-ification of VC[40:26] The missed opportunity in AI safety and agentic workflow guardrails[48:59] How founders can prepare for due diligence the right way[56:22] Why investor updates and clear KPIs determine long-term trustConnect more with Thorgeir on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

  --------  

  1:06:57

  --------

  1:06:57
• 67: People, Process, Technology: The Leadership Formula Every CTO Needs

  Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.What if the real lever isn’t the tech at all?In this episode, I sit down with Matthew Carr, who does interim work and often comes in as the firefighter when a company has taken a wrong turn. He lays out why people come first, processes second, and technology follows.He started in classic ASP and built a loyalty program for the heating and engineering sector. Real-time results beat long compile cycles and changed how he delivered. A private-equity buyout couldn’t get the startup’s tech delivered, so he sat one-to-one with everyone to map the problems. Turns out, fixing broken delivery isn’t about new tools. It’s about people, trust, and having the guts to act fast.You’ll Learn:The reason putting people first makes process work and technology followWhat happens when you plan three sprints ahead and tie outcomes to business valueThe link between quick wins and winning trust in the first 30 daysThe damage of being six to twelve months off on deliverables after a PE acquisitionWhat it feels like to inherit a program that hasn’t shipped in 18 monthsThe link between weekly iterations, monthly demos, and a product becoming a bedrock of the businessThe reason trust, leadership, and alignment are the core enablers of the people pillarWhat happens when you play their game first by showing a six-week plan the board can approveThe reason “believe in yourself” is the sharpest one-line tip for new CTOsTimestamps:[00:00] Introduction[05:12] Why people come first before process and technology[10:46] Lessons from early development work in classic ASP and loyalty programs[15:58] How a private equity acquisition exposed major delivery delays[21:37] Running a massive retrospective and uncovering 110 problems[28:04] The importance of quick wins and building trust in the first 30 days[33:41] Planning three sprints ahead and reporting outcomes instead of outputs[38:22] Turning around a project that hadn’t shipped in 18 months[45:09] How weekly iterations and monthly demos rebuilt momentum[51:28] The one-line advice Matthew gives every new CTOLearn more from Matthew on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

  --------  

  53:48

  --------

  53:48
• 66: CTO Playbook: Leading Change Without Chaos — Giorgia Prestento

  Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.Logic alone won’t land; people react to change emotionally.In this episode, I sit down with Giorgia Prestento, a behavioral scientist and author of The Change Maze. She’s here to show why change so often derails and how CTOs can lead through it with clarity and confidence.We break down why rational explanations fall flat, the different speeds leaders and teams move at, and how losing control sparks uncertainty and anxiety. A call center story shows how rewarding quick answers without customer outcomes skews behavior. A Hong Kong example proves that “ask your line manager” messaging failed culturally, so we rewrote it to a nominated peer contact. A pre-mortem setup surfaces blind spots by declaring the project failed and collecting reasons before execution. We run through an eight-step playbook from purpose and alignment to blind spots, impacts, resistance, indicators, validation, and finally execution.You’ll Learn:The reason logic-only change pitches backfireWhat happens when leaders move faster than teamsThe link between the metric you reward and the behavior you getWhat it feels like to run layoffs twiceThe reason pre-mortems workWhat happens when you don’t set indicators earlyThe link between purpose, alignment, and smoother executionWhat happens when a key trainer is missingThe damage of losing clarity at the topTimestamps:[00:00] Introduction[05:18] Why logic fails when leading change[10:42] The emotional side of resistance and uncertainty[15:56] How leaders move faster than their teams[20:11] The blind spot that halted a global SAP rollout[26:27] Why bad metrics destroy good behavior[31:03] Cultural barriers that derail transformation[36:49] The pre-mortem method for spotting hidden risks[42:08] The eight-step change playbookResources Mentioned:Master the Change Maze by Giorgia Prestento | BookGiorgia offers a short assessment 'Leaders: Are You Change Ready?' You will gain valuable insights across the categories of Leadership Style, Change Expertise and the Readiness of your organisation. It takes less than 3 minutes. You get readiness scores in a personalised report. Plus a digital copy of her book, Master the Change Maze. Click here to get started.You can connect more with Giorgia on LinkedIn. Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

  --------  

  49:07

  --------

  49:07
• 65: Unrealistic Planning, Broken Collaboration — and How to Fix Both

  Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.Are you optimizing for starting work instead of finishing?In this episode, I’m joined by Joakim von Prónay, an engineer and psychologist by education and a coach by passion.We break down how fake roadmaps and a “Global Roadmap Owner” role turn planning into a Gantt chart exercise. We make planning useful with a simple rule: it’s better to be roughly right than precisely wrong. Predictability becomes the lever for real accountability, measured by “did we do the things we said we were gonna do.” Escalation culture gives way to real collaboration, not the default “ask the boss” reflex.You’ll Learn:The reason long-term planning works when it’s roughly right instead of precisely wrongWhat happens when teams are incentivized to start work instead of finish itThe link between delivery predictability and real prioritization and accountabilityThe damage of treating roadmaps like a Gantt chart exerciseWhat it feels like when every question defaults to “ask the boss” instead of talking directlyThe reason fragmented steering creates conflicting directionsThe link between a single “central rule” and measurable goalsTimestamps:[00:00] Introduction[06:14] Why high-performing teams are so rare[09:27] The danger of planning for perfection[15:46] Why teams start work instead of finishing it[19:32] The power of predictability and real accountability[25:40] When collaboration breaks down into escalation[31:58] What fragmented steering really looks like[38:45] The rule that defines true strategy[46:23] A Spotify story and the engineer’s warning[51:17] How alignment turns insight into actionConnect more with Joakim on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

  --------  

  54:36

  --------

  54:36
• 64: What Got You Here Won’t Get You There — CTO Leadership with Catherine Stagg-Macey

  Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!What if the playbook that built your career suddenly stopped working and nobody told you?In this episode, I sit down with Catherine Stagg-Macey, an executive coach who works with technical experts turned leaders. She knows firsthand what it’s like to move from coding and spreadsheets into managing people, and the struggle that comes with it.We get into what happens when being the smartest person in the room is no longer enough, the patterns that keep leaders trapped in the systems they built, and the hard pivot it takes to step into a new kind of leadership.You’ll Learn:The reason smart technical leaders hit a wall when old habits stop workingWhat happens when you try to manage people with the same mindset you used to write codeThe link between control, trust issues, and being stuck in endless meetingsThe damage of wearing the “superhero cape” and building a culture of firefightingWhy skepticism is common when leaders are first asked to work with a coachThe pivotal moment that led Catherine from consulting success to a coaching careerHow childhood patterns and early work experiences quietly shape leadership behaviorsThe role of feedback, or the lack of it, in pushing leaders toward breaking pointsWhy creating distance from your triggers opens space for better choicesTimestamps:[00:00] Introduction[06:15] Breaking patterns of overwork and constant meetings[08:55] The lure and cost of playing the workplace superhero[10:20] Catherine’s pivot from consulting success to coaching[16:05] When rock bottom moments force change[20:15] Early warning signs leaders ignore before burnout[26:45] Identity shifts required to let go of old leadership habits[30:10] Recognizing triggers and unconscious behavior patterns[41:20] How upbringing and culture shape leadership reactions[53:00] Building range as a leader in times of uncertaintyResources Mentioned:Conversations at the Edge | WebsiteYou Didn’t Chase Leadership. Leadership CHASED You. Join Catherine’s Inner Circle.Unlock your leadership superpower, discover what your leadership style is with Catherine’s Leadership Style Quiz.You can connect with Catherine on LinkedIn and listen to her podcast here. Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

  --------  

  59:12

  --------

  59:12

More Business podcasts

Trending Business podcasts

About The CTO Playbook