Founder Mode

Kevin Henrikson and Jason Shafton

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Founder Mode is a podcast for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

-6 ДН.

AI as a Financial Co-Pilot with Shain Noor

EPISODE 53 In this episode, Kevin and Jason sit down with Shain Noor, co-founder of Silvia, an AI-powered personal CFO built to help people reason through financial decisions, not just track them. Shain explains why the entire history of personal finance apps has focused on clicking and aggregating data rather than helping users actually decide what to do, and how Silvia uses Anthropic-powered agents with a verification layer to deliver trustworthy, personalized financial guidance. The conversation covers the co-pilot vs. autopilot distinction, the surprising discovery that users ask Silvia things they'd never tell their human financial advisor, how proactive alerts like the daily summary email drove retention, and why building the reasoning layer first, before adding any execution or action capabilities, is the right foundation for trust. CHAPTERS 00:00 - The judgment-free financial advisor 02:38 - Introducing Shain Noor and Silvia 03:51 - Why finance apps have always missed the reasoning layer 05:51 - Co-pilot vs. autopilot: trust, transparency, and guardrails 08:29 - What surprised Shain: users sharing what they hide from their advisors 12:42 - Measuring retention and the proactive alerts breakthrough 17:02 - Team size, the ProCap merger, and competing with legacy finance 19:41 - The future: everyone becomes a manager of AI agents LINKS Connect with Shain Noor Silvia • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

23 мин.
16 АПР.

Grab A Shovel

EPISODE 52 Jason Shafton and Kevin Henrikson unpack where AI is genuinely useful and where it starts to create more noise than leverage, using examples from AI email triage, long chat memory drift, and agentic workflows. Kevin explains how memory can become polluted when models start treating their own prior inferences as fact, including a prompt he used to compare what an AI thought was “ground truth” against what he had actually told it. From there, the conversation shifts into a practical framework for building AI systems and human teams the same way: define the job, provide the right tools and access, layer in review and guardrails, and judge success by whether time spent together compounds into more output. They close by connecting startup hiring, high-agency operators, and founder-led culture back to the same core test they use for AI: does this person or tool create leverage, or does it create drag? CHAPTERS 00:00 – AI memory drift and false “ground truth” 01:24 – Testing AI email triage and the risks of over-filtering 03:13 – Good AI versus bad AI in real workflows 05:31 – Why controlled memory leads to more consistent AI outputs 08:29 – How to apply AI to workflows that currently rely on humans 11:12 – Building multi-agent content systems with clear roles and QA 13:40 – Hiring high-agency people for early-stage teams 16:01 – The “pick up the shovel” standard for startup operators 22:36 – The real test for both employees and AI: leverage or drag 26:16 – Founder Mode Top 5 Takeaways LINKS Connect with Kevin Henrikson LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

27 мин.
9 АПР.

Turning Audiences Into Businesses with Courtney Spritzer

EPISODE 51 Courtney Spritzer breaks down how she built, scaled, and monetized a community-first business by starting with conversations instead of a business model, and why most founders confuse audiences with real communities. Drawing on her journey from launching a social media agency to co-founding Entreprenista, she explains how trust and engagement—not follower count—determine whether a community actually works, and how to measure that through real outcomes like connections, clients, and visibility. The conversation covers practical approaches to monetization through membership tiers, founder-led power groups, and events, as well as why IRL experiences are a powerful growth engine. Courtney also shares how she evaluates opportunities as an investor, how she maintains authenticity while scaling, and why founders should build around their strengths rather than chase trends like AI. CHAPTERS 00:00 – Following vs. community: the core distinction 04:49 – From agency to Entreprenista: turning audience into business 08:23 – How to measure if a community is actually working 10:56 – Monetization: tiers, power groups, and testing models 13:15 – Transitioning post-exit and doubling down on community 14:22 – IRL events as a growth and engagement engine 17:50 – Investing and evaluating founder-led opportunities 20:25 – Building in the AI era vs. staying human-first LINKS Connect with Courtney Spritzer Entreprenista • Entreprenista LinkedIn • X/Twitter • LinkedIn • Instagram Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

26 мин.
2 АПР.

When AI Agents Go Rogue

EPISODE 50 Kevin Henrikson and Jason Shafton unpack the reality of working with AI agents, why they feel more “broken” than chatbots when they fail, and what it actually takes to make them useful in real workflows. They explore the shift from prompt-based interactions to autonomous systems with memory, triggers, and recurring tasks, and why expectations are often misaligned with how these systems behave. The conversation dives into the importance of guardrails, human-in-the-loop review, and treating AI like a junior employee rather than a perfect operator. They also cover the emerging dopamine loop of working with AI, how it’s changing the way people think and work, and why communication—not technical skill—is becoming the key differentiator in an AI-driven world. CHAPTERS 00:00 – Why AI agents feel more broken than chatbots 02:38 – Harness engineering, workflows, and expectations 05:50 – AI agents as employees and human-in-the-loop systems 07:25 – The dopamine loop and changing how we work 13:54 – The future of work and communication as the edge LINKS Connect with Kevin Henrikson Website • LinkedIn • X/Twitter Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

19 мин.
26 МАР.

The Future of AI-Built Software with Nima Keivan

EPISODE 49 Nima Keivan joins Kevin Henrikson and Jason Shafton to break down what it takes to move AI-built software from demos into production. Drawing on his background in robotics and autonomy, Nima explains why the real challenge is not generating code but closing the “autonomy gap” between what a system can do reliably and the messy corner cases humans still have to carry. He unpacks why durable software starts with requirements, how his team approaches PRD-driven development and scenario testing, why just-in-time mocking matters when automations touch live enterprise systems, and where natural-language software building is already working versus where full end-to-end autonomy is still not ready. CHAPTERS 00:00 – The autonomy gap between demos and production 03:15 – What robotics teaches AI builders about reliability 07:32 – Why code generation is not the real bottleneck 13:18 – How Durable turns operator workflows into production software 26:32 – When natural language can actually replace writing code LINKS Connect with Nima Keivan Durable • LinkedIn • X/Twitter Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

32 мин.
19 МАР.

The End of Prompt Engineering with Dennis Pilarinos

EPISODE 48 Dennis Pilarinos joins Kevin Henrikson and Jason Shafton to unpack what AI in software development actually looks like beyond the demos, arguing that the real bottleneck is not code generation but context. Drawing on his experience building Buddybuild, working inside Apple, Amazon, and Microsoft, and now leading Unblocked, Dennis explains why source code alone is not enough for either engineers or AI agents to succeed, how historical decisions buried in Slack, Jira, and docs shape production-safe software, where AI-generated code breaks down in legacy systems, what traits matter most when hiring in an AI-native era, and why the workflows teams rely on today, including pull requests, may look very different in the near future. CHAPTERS 00:00 – Why AI coding tools fail without context 04:03 – Building Unblocked to solve the missing layer in engineering 12:11 – Where AI-generated code breaks in real production environments 20:33 – Hiring for curiosity, ownership, and success in an AI-native world 27:18 – Founder lessons from aviation, uncertainty, and staying grounded LINKS Connect with Dennis Pilarinos Unblocked • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

33 мин.
12 МАР.

AI Agents Are the New Employees

EPISODE 47 In Episode 47 of Founder Mode, Kevin Henrikson and Jason Shafton unpack why AI agents should no longer be thought of as simple tools, but as a new kind of workforce that founders can hire, coach, evaluate, and orchestrate. They explore how the founder role is shifting from building and doing toward designing systems, managing agent workflows, and making the judgment calls that still require human trust, taste, and strategic thinking. Along the way, they discuss AI-first operating habits, what this means for hiring and team design, why small teams may become dramatically more powerful, where human oversight still matters most, and why the real moat in an AI-native world is not the agents themselves but distribution, proprietary workflows, and unique data. CHAPTERS 00:00 – The founder’s job has changed 00:32 – AI agents as a new staffing model 06:29 – What AI-first workflows look like in practice 16:48 – Hiring and scaling in the age of agents 24:06 – The new moat: data, workflows, and distribution LINKS Connect with Founder Mode Founder Mode Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

27 мин.
5 МАР.

Bring Back BlackBerry with Kevin Michaluk

EPISODE 46 CrackBerry Kevin, founder of Clicks, explains why building hardware in a software-obsessed world is suddenly the opportunity again and how “intentional tech” is creating room for focused devices that complement, not replace, your iPhone. He shares the arc from launching CrackBerry.com and Mobile Nations to turning years of product coverage into an unfair advantage for building, then breaks down Clicks’ strategy: validate demand with accessories first, frame Communicator as a purpose-built “people phone” category instead of a smartphone competitor, and use CES storytelling to create momentum months before launch. The conversation also digs into how Clicks approached fundraising without relying on traditional VC, leveraged community as both customers and megaphone, and avoided the classic Kickstarter trap by sequencing products, aligning supply-chain incentives, and refusing to overpromise on timelines. CHAPTERS 00:00 – The “people phone” idea: why Communicator won’t compete with iPhone 04:14 – From CrackBerry to builder: compounding reps and community advantage 06:56 – Naming a category: Communicator as a purpose-built device, not a smartphone 18:58 – CES momentum: how storytelling and launch mechanics are engineered early 21:43 – Bootstrapping, community funding, and avoiding the Kickstarter failure loop LINKS Connect with CrackBerry Kevin Clicks • LinkedIn • X/Twitter Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

36 мин.

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Оценок: 3

Founder Mode is a podcast for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

Автор

Kevin Henrikson and Jason Shafton
Годы выхода

2025 - 2026
Выпуски

53
Ограничения

Без ненормативной лексики
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© Kevin Henrikson and Jason Shafton
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Founder Mode