Transcript
[04:33] Welcome and host introduction
Andrew Murphy: Hello, everybody, and welcome to another Tech Leaders Launchpad livestream. If this is your first time—hi, I'm Andrew Murphy. I'm the founder of Tech Leaders Launchpad, and I've been in the tech industry since the early 2000s. I got into leadership way too early. Back then there weren’t many resources to help you understand what it means to be a tech leader. I was promoted before I was ready—a common story in our industry. Now I help people understand the role of technology leadership, and one of the ways I do that is through these livestreams. I share the people who are my mentors—the folks I learn from around the industry—with you to hopefully help you as well.
[05:28] Introducing today’s guest: Dave Kuhn
Andrew Murphy: With me today is one of those people—Dave Kuhn. Welcome to the livestream!
Dave Kuhn: Hi, Andrew. Thanks for having me.
Andrew Murphy: You’re more than welcome. I’ve been looking forward to this for a while. We try to do these monthly, but with welcoming our second baby in April, we couldn’t do April—so we’re here in May. I’m super looking forward to this.
Dave Kuhn: Congratulations! And I’m glad we were able to make this happen.
[06:08] Icebreaker: favorite tech gadget that isn’t a computer/phone/tablet
Andrew Murphy: I like to start with a quick icebreaker to get us—and the chat—talking. What’s your favorite tech gadget that isn’t your computer, smartphone, or tablet? Something techie, but not a computing device.
Dave Kuhn: This ties into what you said about welcoming a new family member. I used to play a lot of guitar before I had kids. Once you’ve got kids sleeping—especially if you’re into electric guitar—historically the only option was an amp that sounded terrible unless it was at 11. A USB audio interface is my favorite bit of tech. I can plug it into my computer, put on headphones at night, pick up my seven-string behind me, jam out, add effects, run it as loud as I want—and not wake anyone up. Total game-changer.
Andrew Murphy: That’s so cool. I love that—playing an instrument without making sound. It’s a great life improvement. A friend of mine used to rent houses with two rooms between him and the neighbors so he could play drums. Then electric drum kits came along—headphones on—and no one hears a thing. Massive change.
[08:25] Andrew’s pick: wearable display glasses for travel
Andrew Murphy: My favorite this week is these things. I just got them a couple of days ago—glasses with a screen built in and a USB-C interface. Any device that supports USB-C DisplayPort Alt Mode—smartphones, tablets, computers—you plug them in and see the screen in the glasses. I do a lot of international travel. Rather than craning my neck down at an iPad or the not-great seatback screen, I can put these on, relax, and see a 120-inch screen in front of me. Even on planes without built-in screens, you’re constantly asked to remove your device for meals or takeoff/landing. Last time, using an iPad for entertainment was awkward during meals—trying to perch it and hoping it doesn’t fall into your neighbor’s orange juice.
Andrew Murphy: I’m flying to Oslo on Friday to run a workshop. I’m hoping this will be a big game-changer. I’ll let you know, Dave—and report back on the next livestream if anyone’s interested.
[10:40] Audience shout-outs and gadget picks
Andrew Murphy: Bradley says, “Looking forward to Dave’s insights.” Thank you, Bradley! If you’ve got questions for Dave, please post them. Patrick says his favorite tech device is a watch—I'm guessing a smartwatch? Or a classic? And then you also said AirPods—very indecisive there! We’re only going to let you have one, Patrick—pick one!
[11:18] Setting the topic: scaling yourself as a CTO—why it matters
Andrew Murphy: I usually start with introductions plus a bit on today’s topic—scaling yourself as a CTO. Before these livestreams, my guest and I discuss a topic they care deeply about and have a unique perspective on. This is the one we picked, Dave. By way of introducing yourself, can you share why this topic matters to you?
[12:06] Dave’s background and why “scaling yourself” resonates
Dave Kuhn: I resonated with what you said earlier—promoted earlier than ready and not knowing what I needed to be effective. You can learn on the job, but it’s the harder way. I started as a software engineer, began a Master’s of business (kind of MBA with tech), but dropped out when my startup got funded. I was two years in with one to go and went to Silicon Valley. I’ve been doing startups since before I even knew they were “a thing”—e.g., a security hardware startup in 2003 doing Wi‑Fi/solar‑powered cameras for construction sites when Wi‑Fi was barely a thing.
Dave Kuhn: In 2011, my company was in the first Startmate batch. We went to the US and were accepted into 500 Startups, missed out on YC at the final stage but had lunch with Sam Altman. I founded Spaceship (a superannuation company) which was sold to eToro last year. Since then I’ve worked with 20+ startups/scaleups as a fractional CTO. I wasn’t sure what my next startup would be, so I applied my skills to help others—super passionate about the Aussie startup ecosystem. Australia’s a great place to do this. I want depth in the industry and startups not just surviving but thriving on a global stage—which implies scale.
Dave Kuhn: I’ve worked across fintech, medtech, energy, biotech, edtech, HR—with CSIRO, Zip, Future Super, Propeller, Aerologix (local drone company), and more. I love learning how businesses work, how tech applies, and how to ensure tech isn’t a bottleneck but the secret to success—the engine room. There’s a tendency—especially with non-technical founders—to see tech as a cost center to minimize instead of a value center to maximize. That mindset’s shifting, but it persists, especially from corporate transplants.
Andrew Murphy: We’ll touch on why that persists—and how to fix it. The CTO plays a massive part in preventing tech from being an anchor and making it a growth lever.
[17:38] What does “scaling yourself as a CTO” actually mean?
Dave Kuhn: Early on, your CTO is an individual contributor—you can get something to market alone or with a couple others to reach MVP. Then you build the team. Many CTOs have some leadership experience—mentoring or tech lead, small team management—but few have gone beyond that. Beyond ~7 people (the golden ratio for team size), it gets hard to give everyone the attention they need. You split teams. Fast-forward and you’re managing managers—like a Rube Goldberg machine where one action here causes outcomes there. As layers add up, complexity grows.
Dave Kuhn: It’s not just the tech ballooning—it's the exponential complexity of relationships and interactions among people you’re responsible for. Simultaneously, your executive peer group grows; you might add a board with its dynamics. That’s new territory for someone who was an IC or tech lead. Those are distinct skills. Transitions between stages are where CTOs are most at risk—either failing the mission or developing habits that cause future problems. Getting this right matters—it’s the value engine of a tech startup.
[21:27] Communication complexity: from people to teams-of-teams
Andrew Murphy: Here’s my favorite visualization: think of dots as people and lines as communication paths/decision interfaces. Three people have three lines. With four people, there are six; five people, ten; six, fifteen; seven, twenty-one. The ways you communicate and the processes that work for a small team just don’t scale. It’s fractal—when you become a leader of leaders, the dots become teams, with the same effect.
Dave Kuhn: It’s like looking at the night sky and realizing some “stars” are actually galaxies when viewed through a telescope. I love this visualization—you don’t realize how much complexity there is. Chaos theory is real: a single conversation ripples out to the team in unpredictable ways. You need skill—and it helps not to learn all of this purely through trial and error. When you’re an engineer, the computer doesn’t care if your unit test fails 100 times. As a leader, mistakes affect humans. People don’t quit the company—they quit their boss. Your actions really matter.
[24:51] The Rube Goldberg leadership analogy: shrinking feedback loops vs. ambiguity
Andrew Murphy: I like your Rube Goldberg analogy for leading at scale. As a junior engineer, you’re happy if your code compiles—the feedback loop is tight, ambiguity is low. As a senior, you care about scale; the feedback loop is longer, ambiguity higher. As you go into leadership, this continues. You can’t be there for every step of the machine—you must set it up for success and take a holistic view. Is a common mistake either being totally hands-off or constantly tweaking while it runs?
Dave Kuhn: I more often see the exhausted CTO trying to be everywhere at once—plugging holes. We’re used to deterministic systems—unit tests, diagnostics, monitors—but humans are non-deterministic (in a good way). I think of teams as a distributed system—each person an autonomous agent/microservice. The only way to manage complexity without control is to give people the framework to make their own decisions.
Dave Kuhn: Most engineers are smart and want to do good work. The problem is the workplace often doesn’t define the framework for success. An underdeveloped leader gets prescriptive—dictating every detail. But you’re paying for smart people—give them the context. That’s alignment: communicate strategy and translate it for your teams. Say: “It’s crucial we move from X to Y by this time. In your meetings and design sessions, ask: does this help us get there sooner? That’s the decision rule.” Now people aren’t guessing how to please you—they have success criteria and can use their initiative. If you see a leader with all fingers in the dike, ask: are we communicating the what (not the how) effectively?
[33:20] Breadth vs. depth—and what happens when you don’t provide purpose
Andrew Murphy: As you rise, your breadth increases and you sacrifice some depth. People with the depth (building and perfecting the product) lack some breadth—human brains and workweeks have limits. The leader’s job is to distill/contextualize breadth for those with depth.
Andrew Murphy: Nature abhors a vacuum—if you don’t provide that input, people invent their own rationale. I see frustrated CTOs/CEOs asking, “Why are they focused on microservicing everything, replatforming on Kubernetes?” Often, they’ve invented purpose because you didn’t give them one.
Dave Kuhn: Exactly.
[34:52] Red flags you’re not scaling yourself well (and what to do tomorrow)
Andrew Murphy: Let’s get actionable. What can a scaling CTO notice about themselves, their behavior, or their teams that indicates things aren’t on the right track—and it’s time to reassess and change behavior?
Dave Kuhn: If everything’s coming at you too fast—if you constantly feel behind the eight ball—you’re not on top of it. The common reaction is to work longer/harder to “get past the next couple of things.” That won’t fix it—if your startup is doing well, it will get worse. Step back. Gain distance. You likely haven’t done adequate planning. There’s probably work on your roadmap that doesn’t need doing or isn’t aligned—you could draw a line through it tomorrow. Sunk cost pain, yes—but you’ll free capacity immediately.
Dave Kuhn: Another signal: are you sidelined from conversations with co-founders/executive team/board? Sometimes tech leaders get shielded—“We don’t want to bother you, just focus on X.” That’s reasonable for a manager to do for their team—but not for an executive. At scale, you are an executive. Executives don’t get to hide. If you feel on the outer, you’re likely too focused on details and not investing in communicating your requirements up and across so your peers/board know what they must do to support your work.
Dave Kuhn: Don’t just put your head down and pump harder. The real growth is: get a plan, ensure you’re only doing aligned work, and build the muscle to communicate needs/trade-offs with peers, board, and investors.
[45:46] “Yes, and…”: turning ideas into visible trade-offs and shared decisions
Andrew Murphy: There’s a great improv guideline—“Yes, and…” Never respond with no. Say “Yes, we can—and here are the consequences.” The CEO looks broadly with less depth; the CTO brings depth about technology. Your job is to bridge that gap—bring awareness of consequences to someone with broad focus.
Dave Kuhn: If a CEO asks you to teach them tech so they can talk to you, that’s actually a failure by the CTO to keep the conversation at the right level. “Learning to talk business” isn’t mysterious—but you must lean into it. I keep my own spreadsheet of all tech expenses—SaaS, hosting, staff costs—and a budget/cash flow model. If I say we need another team, I can answer “How much will that cost?” instantly. That builds trust fast.
Dave Kuhn: Also know your capacity for real: how many teams/sprints, how many person-days—across the portfolio. When the CEO says, “We need to do X,” pull up the roadmap. I still like Gantt at the roadmap level. Show the next few sprints: who’s doing what and when. Then ask, “What do you want to move?” If nothing can move, the answer is “We add a team/contractors—here’s the cost and the earliest start.” Now they share the same dilemma. Too often CTOs just reflect problems back—vein pulsing—“Don’t you see how much we have on?” Instead, invite them into a shared mental model of trade-offs. You can’t do that without visibility into capacity and costs.
Andrew Murphy: Exactly—yes and consequences. Keep the conversation at the right altitude.
[50:59] AI in 2025: what leaders should adopt, avoid, and enable
Andrew Murphy: We can’t have a livestream in 2025 without AI. What are you doing now to help your job as a leader? What should people do or avoid? How can AI help or hinder technology leaders?
Dave Kuhn: It’s deservedly the year of AI questions. Adoption in software teams is high (state of AI reports show ~two-thirds), but deeper, agentic tools (Claude Code, Cursor, Windsurf, Lovable, etc.) face resistance. Heavy-handed mandates (“you will use this”) are a mistake—coercion fails long-term.
Dave Kuhn: I use tools like Claude Code personally and with teams—but we treat them like a very knowledgeable junior: great acceleration, but you still need code review. Code comprehension must improve across the team—there’s going to be more code produced. AI is great for manual transformations (data representations, scaffolding).
Dave Kuhn: Most startups are on Google Workspace; Gemini is now included. It’s beating ChatGPT on benchmarks and you have it already—so use it. Ask up front: could AI do this faster, or part of it better? But read the terms of service and don’t leak IP. Blanket rule: no free AI tools with company code/data. If it’s free, you’re the product—you have no protections.
[55:47] AI as a junior collaborator—and preserving your unique voice
Andrew Murphy: That rule applies generally—if it’s free, you’re the product. Treat AI like a junior collaborator. I use AI to draft text sometimes—but I don’t just copy/paste. It’s a starting point. The earlier you use AI in the creative process, the more your unique perspective gets diluted. AI takes the average of the internet—by definition, the average isn’t compelling. If there’s a word for default AI output, it’s “mid.”
Andrew Murphy: There’s a massive shift coming in tech. The best way to prepare is to learn the tools. The people who can use the tools effectively will lose their jobs last.
Dave Kuhn: Embrace it. My kids asked if coding will still be a job—“Will AI take it?” I used a loom analogy: once, every village had a few people making clothes; then factories changed that. People lost jobs, there was pain, but work evolved. It’s unlikely we’ve invented something that ends human work forever. We’ll work differently. Even if we can’t imagine the shape now, the pattern of history is clear.
Andrew Murphy: Society will be fine, but during this transition, individuals do best by learning the tools and using them effectively.
[59:45] Wrap-up, next livestream, workshops, and Dave’s CTO course
Andrew Murphy: We’ve reached the top of the hour—crazy how fast that went. Thank you, Dave—this was all over the place in the best possible way.
Dave Kuhn: Thank you—that was great.
Andrew Murphy: We’ll definitely have you back. Next livestream is with Shirley Hart in just over a month: how to get your boss to listen to your ideas—right in line with today’s theme of tech leaders communicating effectively to peers and bosses.
Andrew Murphy: Over the next few months, I’m running workshops around Australia and New Zealand—an introduction to technology leadership: making the transition from excellent technologist to leader of people. Auckland, Wellington, Brisbane, Melbourne, Sydney, across ANZ. If you want details, scan the first QR code; if you want to follow me/newsletter, the second QR code.
Andrew Murphy: Dave, anything to share?
Dave Kuhn: I’m developing a course for CTOs and would love your input on what you’d like to see. I shared the link with Andrew—he’s posted it. Your input will make it better by incorporating the real problems you have.
Andrew Murphy: Those are the best courses—the real problems people actually face. We are over time—thanks again, Dave. Thanks everyone for watching. See you next time on Tech Leaders Launchpad Livestreams.
