In this episode, Jeff Mains sits down with Alistair Gordon, founder of Expertunity and author of "Master Expert," to explore why technical excellence alone isn't enough to drive career momentum and organizational impact.

Alistair reveals how subject matter experts (SMEs) can unlock influence without abandoning their technical edge through what he calls "expert ship"—a set of enterprise skills that translate expertise into clear business value. The conversation challenges the assumption that management is the only path forward for technical professionals and offers practical frameworks for founders looking to retain and grow top technical talent.

[5:00] - The leadership development gap: Only 11% of first-time leaders receive training in their first year, leaving 89% to sink or swim

[7:50] - Why "knowledge leader" failed: Technical experts don't want to be leaders—they want to avoid "useless meetings where nothing gets done"

[12:00] - The invisibility problem: Much of experts' work (like keeping email systems running) is completely invisible until something breaks

[14:30] - Expert as coach: The most transformational skill is learning to ask better questions before providing technical advice

[19:30] - The coaching paradox: Half of stakeholders love the questioning approach; the other half just want immediate answers

[23:00] - The negativity trap: Experts often spend 22 minutes explaining why something is difficult before mentioning it's actually a good idea

[29:00] - The promotion trap: Three out of four times, forcing technical experts into management roles is "a train wreck"

[40:30] - The remuneration shift: In successful tech companies, technical experts often earn more than leaders because they add more value

💡 "The era of people leaders dominating organizations is over. It's technical experts who are keeping the lights on and inventing the future." - @AlistairGordon

💡 "You can't teach a technical subject matter expert anything. They have to learn it. They have to want to learn it themselves." - @AlistairGordon

💡 "Most experts think their value should be obvious. But if your work is invisible and you can't describe it clearly, it won't be noticed." - @AlistairGordon

💡 "Career progress doesn't equal promotion. Most technical experts want to invent stuff that's cool and makes a difference—not fill in appraisal forms." - @AlistairGordon

💡 "The transition from individual contributor to first-time leader is the hardest transition in leadership—and it's five times harder for introverted technical experts." - @AlistairGordon

💡 "Find something positive to say first. Don't let technical complexities dominate the conversation before understanding what they're trying to achieve." - @AlistairGordon

Most leaders assume everyone wants career progression through management. Technical experts often want to build cool things that make a difference, not manage people. Ask what drives them before creating development paths.

Don't force technical experts into management roles they don't want. Establish technical career tracks with comparable compensation and recognition. The best chip designer at Nvidia isn't being "weighed down with management responsibilities."

Technical experts need coaching, stakeholder engagement, business acumen, and communication skills to translate their work into business value. These "enterprise skills" (not "soft skills") are what unlock their full

Ryan Debenham, CEO of Grin, shares his unconventional journey from software engineer to leading a nearly billion-dollar creator management platform. In this candid conversation, Ryan reveals how he "accidentally" became a CEO by following challenges rather than titles, and why that mindset shift transformed how he builds products and companies.

He discusses the critical disconnect between engineering and go-to-market teams, the revolutionary potential of AI agents in influencer marketing, and why democratizing influence could unlock a massive untapped market. Ryan also shares insights from his time at Qualtrics (acquired by SAP for $8B) and Route, offering practical wisdom on connecting product teams to revenue outcomes and building AI that feels "alive."

[4:30] - The Accidental CEO Path: Ryan explains how becoming a CEO was never his plan—he loved building products but never built companies around them. His career evolved by chasing challenges rather than titles or money.

[10:30] - The Product-to-Company Graveyard: Ryan candidly shares how his early product ideas (including a ride-sharing concept 20 years ago and a photo categorization tool) died because he focused only on building, not on solving the hard business problems.

[12:15] - The Mindset Shift: The biggest change from engineering to CEO? When revenue numbers became Ryan's responsibility, he finally understood what customers truly needed—not just what they said they wanted.

[14:30] - Breaking Down Silos: Ryan discusses why the tension between product, engineering, marketing, and sales "will kill the business" and how he's connecting these departments at the hip.

[19:30] - The Qualtrics Lesson: A powerful story about spending six months building the wrong text analytics product at Qualtrics, despite sitting next to customers repeatedly. The lesson: understanding business needs requires deeper connection than just listening to feature requests.

[26:00] - AI as Electricity: Ryan's compelling analogy comparing LLMs to the development of electricity and CPUs—powerful building blocks that are worthless alone but transformational when paired with the right infrastructure.

[28:30] - Mandatory AI Adoption: Ryan required all engineers at Grin to use AI coding tools. One engineer quit over the pressure but came back, realizing it was a mistake. His prediction: in a few years, you won't get hired as an engineer if you don't know AI tools.

[32:00] - Building Software That's "Alive": Ryan describes Gia, Grin's AI agent that journals daily, runs standups with other agents, creates action items, and can discuss what she's learning and what features should be built next.

[35:00] - The Influencer Marketing Problem: Why Grin's growth stalled—aspirational customers bought the software but failed at influencer marketing because the operational complexity was too high, leading to churn.

[38:30] - The Two-Sided Platform Gap: Most influencer platforms built for merchants and forgot creators. Ryan explains why supporting creators is the most important part of the solution.

[44:30] - Democratizing Influence: Ryan's vision that "everybody is an influencer"—the real opportunity is capturing and rewarding the micro-influence that happens in everyday conversations between millions of people.

[49:00] - The Collision Course: Why affiliate marketing and influencer marketing are merging into something new—it's all about capturing word-of-mouth at different scales.

In this episode, Jeff Mains sits down with Radhika Dutt, author of Radical Product Thinking, to challenge the conventional wisdom around goal-setting, KPIs, and OKRs. Radhika reveals why chasing metrics can actually distort behavior and undermine long-term growth, introducing a powerful alternative: treating growth like a puzzle rather than a scorecard.

The conversation explores how well-intentioned targets create perverse incentives, why measures should be tools for insight rather than evaluation, and how a curiosity-driven approach—using the OHLA framework (Observe, Hypothesize, Learn, Adapt)—helps teams make smarter decisions in real-world conditions. Radhika shares compelling examples from OpenAI, maritime SaaS platforms, and robotics companies to illustrate how puzzle-solving beats goal-setting for sustainable growth.

Whether you're drowning in dashboards or hitting targets while feeling like something's off, this episode offers a refreshing lens on progress, leadership, and building momentum without the performance theater.

[0:00] - Episode introduction and overview of why goal-setting may be backfiring

[4:48] - The fundamental problem with KPIs and OKRs: Goodhart's Law and Campbell's Law explained

[6:28] - Dutt's Law: "A measure is only useful as a tool for insight, not a yardstick for evaluation"

[7:16] - Real-world example: How OpenAI's user engagement targets led to dangerous "sycophantic AI"

[10:37] - The hidden dangers of hitting targets while ignoring negative indicators

[11:44] - Introduction to puzzle-setting vs. goal-setting mindset

[12:09] - The OHLA framework explained: Observe, Hypothesize, Learn, Adapt

[17:51] - Case study: Why improving filters wouldn't have solved the real problem

[28:47] - The performance theater trap: Why jumping to solutions feels comfortable but fails

[30:28] - How to get customer meetings when people say "you should already know this"

[33:00] - Why in-person observation matters more when mental models differ

[36:27] - Growth comes from matching user mental models, not forcing adoption of yours

[37:47] - The Tesla UI example: When "cool" design ignores user mental models

[37:47] - Top-down vs. bottom-up: How to introduce puzzle-solving in organizations

[39:27] - Why leaders fear losing control and how to address it

[43:01] - Vision-driven vs. iteration-led: Crafting a detailed, actionable vision statement

[45:41] - Example vision statement that tells the whole story without mentioning the product

[48:03] - Why detailed visions create ownership better than memorable slogans

[50:01] - One mindset shift founders can make this week to reduce performance theater

1. "When a measure becomes a target, it ceases to be a good measure. We've known this since 1975, yet we keep setting goals for metrics."
2. "A measure is only useful as a tool for insight, not a yardstick for evaluation. That's the critical mindset shift."
3. "When you set targets, everyone's incentive is to show you they've hit that target. You don't look at the negative numbers to see what's actually happening."
4. "Puzzles trigger curiosity and questioning. If you already know the answers, there's no puzzle. That's the...