Assaf Weinberg (Co-Founder & CEO, SetSale) joins Andrew Duncan to dismantle the LinkedIn narratives about software in the age of AI: "code is free," "SaaS is dead," and the founder myth that hiring a developer is the bottleneck.

Chapters

• 00:00 The biggest limit on AI is what you believe it can do
• 01:23 Building SetSale before AI tools existed
• 04:31 Supastarter and the portal boilerplate origin
• 06:47 Why the cost of software isn't zero
• 07:43 The "I just need a developer" myth
• 11:09 Every software company is a data transformation engine
• 13:58 Why SaaS isn't dead
• 17:08 Capture your data or AI can't help you
• 22:20 The Austin distributor story: four days to ship
• 27:34 Artists don't sketch in marble
• 33:30 A developer's job is specification, not code
• 44:13 The new bottleneck is customer adoption

Topics

• Why AI made code cheap but didn't make software cheap
• The "I just need a developer" myth and why it was always a crutch
• UI as commodity, data and process as the only durable moat
• Why every software company reduces to a data transformation engine
• The Austin distributor visit: notetaker, AI PM, Cursor, four days to ship
• Six-week bets as the new unit of org change
• What roles look like when designers don't make mockups and developers don't write code
• The new bottleneck: customer adoption now lags engineering velocity

Guest

Assaf Weinberg, Co-Founder & CEO, SetSale

https://www.setsale.ai/

https://www.linkedin.com/in/assafweinberg/

https://x.com/assafweinberg

Resources mentioned

Sense and Respond by Jeff Gothelf and Josh Seiden: https://www.amazon.com/Sense-Respond-Successful-Organizations-Continuously/dp/1633691888

Granola (AI notetaker): https://www.granola.ai/

Supastarter (Next.js SaaS boilerplate): https://supastarter.dev/

Cursor: https://www.cursor.com/

Connect

Andrew Duncan: https://www.linkedin.com/in/andrew-b-duncan/

Vertice Labs: https://www.verticelabs.io

Subscribe

Spotify: https://open.spotify.com/show/64yoHwDdhBd0vik2sev6xs

Apple Podcasts: https://podcasts.apple.com/gh/podcast/shipping-excellence/id1794200466

YouTube: https://www.youtube.com/@shippingexcellence

RSS: https://media.rss.com/shippingexcellence/feed.xml

Jason Macht (Whitespace Solutions) joins Andrew Duncan to break down what actually changes — and what doesn't — when you build with AI.

Chapters

00:00 Intro

00:40 Guest introduction

02:51 Vibe coding vs. engineering rigor

04:02 AI as amplifier — good and bad processes

04:39 Spec-driven development

06:57 The death of traditional agile

09:35 Agentic systems and guardrails

15:27 New business viability — the solopreneur opportunity

32:09 AI as thought partner and echo chamber risks

49:45 Closing

Topics

• Why AI amplifies good and bad engineering practices equally
• Spec-driven development: engineering at the speed of thought
• The difference between vibe coding and production-ready software
• How solopreneurs can now build niche software businesses without VC
• Agentic systems, guardrails, and what happens when AI has real-world access
• Using AI as a strategic thought partner — and avoiding echo chambers
• Why traditional agile is losing to fast betting cycles

Guest

Jason Macht — Founder, Whitespace Solutions

• https://www.whitespacesolutions.ai/
• https://jasonmacht.com/
• https://www.linkedin.com/in/jasonmacht/

Resources Mentioned

• Cursor: https://cursor.com/
• Replit: https://replit.com/
• Bolt: https://bolt.new/

Connect

Andrew Duncan: https://www.linkedin.com/in/andrew-b-duncan/

Vertice Labs: https://www.verticelabs.io

Subscribe

Spotify: https://open.spotify.com/show/64yoHwDdhBd0vik2sev6xs

Apple Podcasts: https://podcasts.apple.com/gh/podcast/shipping-excellence/id1794200466

RSS: https://media.rss.com/shippingexcellence/feed.xml

YouTube: https://www.youtube.com/@shippingexcellence

AI makes speed cheap, judgment priceless.

They start with the practical: how experienced builders are using AI day to day, why “skills” (constrained context + tools) are emerging as the next standard beyond agents, and what happens when heavy integrations like MCP feel slow or token expensive.

From there, the conversation shifts to the business implications. If AI compresses the time to ship, teams hit decision points faster, with less time to react. That makes judgment and ownership the highest leverage skills. They discuss why AI amplifies whatever process you already have, why “vibe coding” often hits a ceiling without scar tissue, and why the durable moat is still culture: integrity, follow through, and loving the customer by truly understanding them.

They close on the human side of technology: authenticity in a world where it’s harder to know what’s real online, the importance of “third places,” and why remote teams need intentional in person time to build trust and momentum.

Topics covered

• Why AI makes speed cheap, and why judgment becomes the premium skill
• Skills vs agents: constrained context, tool boundaries, and predictable workflows
• Parallel AI workflows: running multiple streams across code and content
• MCP vs lightweight tools: when a CLI beats a server integration
• Emergent behavior: when the model bypasses tools for simpler paths
• AGI and what “human” means beyond text: embodiment, emotion, and social bounds
• AI amplifies process: discipline compounds quality, chaos compounds failure
• Why ownership still matters: “AI isn’t responsible for outcomes, humans are”
• Vibe coding, security gaps, and what breaks at real customer scale
• The new moat: integrity, customer support, follow through, and reputation
• Authenticity vs perfection in an AI saturated internet
• Remote work done right: high bandwidth FaceTime, offsites, and trust currency
• Community and “third places” as technology reshapes connection

Key takeaways

• AI accelerates execution, but it does not remove the need for judgment and ownership.
• The faster you can ship, the faster weak assumptions and bad decisions compound.
• Strong engineering discipline gets supercharged with AI; weak discipline gets exposed.
• Technology is commoditizing, so culture and integrity become defensible advantage.

About the guest

Christopher Garvis is a veteran engineer and former AWS engineering leader who led the AWS CDK team. He focuses on practical AI workflows, tool constrained systems, and shipping with strong engineering fundamentals.

About Shipping Excellence

Shipping Excellence is a podcast about building exceptional software products: practical engineering, strong delivery, and the systems that help teams ship.

Links

• Vertice Labs: https://verticelabs.io
• Follow Andrew Duncan: https://www.linkedin.com/in/andrew-b-duncan/

#ShippingExcellence #AINative #SoftwareEngineering #ProductDevelopment #Leadership #RemoteWork #Agents #Skills #MCP #AWS #StartupExecution

Robert runs a professional language services firm with a remote team of interpreters. He needed a HIPAA-compliant messaging platform and an internal iOS app — and he needed them fast. The experience became a useful lens on what actually makes software partnerships work: not charisma, not promises, just execution, clarity, and trust.

Chapters

00:00 The first problem: getting an app in the App Store fast

02:50 Hesitations before starting — and why there weren't many

07:38 HIPAA-compliant interpreter messaging: the gap in the market

08:26 "You got us to market so fast I didn't have time to build a sales strategy"

10:01 What no-BS looks like in a pitch

12:20 $40K consulting with nothing to show for it

14:33 Executive Linguist: Vertice Labs' ideal client

17:29 How a Stripe security incident revealed the team's character

19:01 Speed and organization: the biggest differentiator

21:00 "You could have milked us — and you didn't"

24:20 Who should hire a software partner

31:15 What made this client relationship work

35:00 How watching the process improved their internal operations

Topics

• What makes a software partnership actually work

• Clear scope of work as a trust foundation

• Transparency, autonomy, and accountability on a dev team

• Speed without sacrificing quality

• What to look for in a software partner — and what disqualifies one

• Building HIPAA-compliant apps for specialized industries

Guest

Robert Randolph, CEO — Executive Linguist Agency

https://www.executivelinguist.com

https://www.linkedin.com/in/robert-randolph-a86ab4111

Resources mentioned

Linear — https://linear.app

Stripe — https://stripe.com

TestFlight — https://developer.apple.com/testflight/

Connect

Andrew Duncan — https://www.linkedin.com/in/andrew-b-duncan/

Vertice Labs — https://www.verticelabs.io

Subscribe

Spotify — https://open.spotify.com/show/64yoHwDdhBd0vik2sev6xs

Apple Podcasts — https://podcasts.apple.com/gh/podcast/shipping-excellence/id1794200466

YouTube — https://www.youtube.com/@shippingexcellence

RSS Feed — https://media.rss.com/shippingexcellence/feed.xml

Aram shares what it feels like to go from “grunt developer” to directing a team of AI agents, how tools like Cursor, Copilot, and Claude accelerate delivery, and why the real role of engineers today is shifting toward strategy, architecture, and orchestration.

We cover:

• How AI coding agents give engineers 10x productivity gains
• The difference between GPT-4.0 and GPT-5 in real development work
• Why AI is best thought of as a “junior developer” you can delegate to
• How MCP servers and Linear integrations automate project management
• Guardrails and feedback loops that keep AI-generated code reliable
• The mindset engineers need to thrive in an AI-native world

Whether you’re a technical leader, founder, or engineer in the trenches, this conversation shows what it really looks like to deliver production-ready software with AI agents as part of the team.

We dive into:

• Why Sergio believes over-reliance on GenAI could weaken cognitive skills
• The lessons he brings from 20+ years as a software engineer, VP of Engineering, and CTO
• His journey from corporate leadership to solopreneurship and advisory work
• How his newsletter Pseudo Make Me a CTO helps engineering leaders grow
• The balance between productivity gains and long-term impacts of new technologies

About Sergio Visinoni: Sergio is a solopreneur in the tech space with over two decades of experience. He advises companies as a fractional CTO, coaches engineering leaders, and writes the popular newsletter Pseudo Make Me a CTO.

Links & Resources:

• GenAI is Digital Cocaine Article: https://makemeacto.substack.com/p/is-genai-digital-cocaine
• Connect with Sergio on LinkedIn: https://www.linkedin.com/in/piffio/
• Read Pseudo Make Me a CTO: https://makemeacto.substack.com/
• Subscribe to Shipping Excellence for more conversations on building and shipping exceptional software products.

You’ll learn:

• How to embed technical leadership that drives focus and results
• The keys to building a lean, high-performing engineering culture
• Why “hire the right people” beats “hire more people” every time
• How Wonder Cave scaled to handle Fortune 50-level clients
• Real-world examples of moving fast without sacrificing quality

Whether you’re leading a startup, scaling a product team, or navigating complex builds, this conversation is packed with practical insights you can apply right now.

Key Topics Discussed

• AI North Star Playbook – Why most companies approach AI the wrong way and how the playbook helps leaders identify high-impact opportunities.

• Experimentation Over Hesitation – Why business leaders need to test and learn with AI tools rather than waiting on perfect clarity.
• AI Agents & Workflows – Understanding what makes an AI implementation an "agent" vs. just AI augmentation in workflows.
• Real-World AI Success Stories – From legal redlining automation to AI-powered RFP evaluation and outbound sales AI.
• The Future of Work & Solopreneurship – How AI will enable one-person unicorns and disrupt industries that rely on manual digital labor.
• Strategic Thinking for Builders – Why software engineers, product leaders, and businesses must rethink how they deliver value in an AI-powered world.
• AI’s Role in Product Development – How AI is reshaping design, engineering, and shipping software at an accelerated pace.

Chapters

00:00 Introduction to AI and the North Star Playbook

03:02 Current Trends in AI Adoption

05:53 AI in Business Processes

08:37 Success Stories in AI Implementation

10:59 The Future of AI in Customer Service

13:26 The Evolution of Business with AI

15:51 Mapping Value Streams with AI

18:40 The Role of Human Insight in AI Development

20:38 Embracing Change in the Age of AI

23:56 The Rise of Solopreneur Unicorns

26:18 AI in Education: A Real-World Success Story

28:40 Democratization of Business: The New Age of Entrepreneurship

30:37 Differentiation in a Noisy Market

32:34 Understanding Customer Needs for Product Success

33:29 Agentic Workflows: The Future of AI

39:06 The Evolution of AI Agents in Business

41:57 Building AI Workflows: From Simple to Complex

44:15 The Future of AI: Hands-Off Interfaces and AGI

Resources Mentioned

📖 AI North Star Playbook – Get the roadmap for building AI-powered solutions.

📚 Range by David Epstein – A must-read on why generalists thrive in specialized fields.

🔗 More resources & insights: verticelabs.io

Takeaways

• John transitioned from finance to product management, learning to communicate effectively with developers.
• Building a supportive team culture is essential for innovation and success.
• Understanding business value is crucial for delivering features that meet customer needs.
• Prioritizing work requires balancing immediate customer demands with long-term product vision.
• Leadership involves getting in the trenches with the team and understanding their individual goals.
• Effective communication between finance and development can drive better product outcomes.
• Investing in QA and automation is necessary for scaling development processes.
• Trust and transparency within the team foster a high-performance environment.
• Finding common ground between visionary ideas and practical execution is key to success.

Chapters

00:00 Building a Team at Modernizing Medicine

09:28 Transitioning from Finance to Product Management

17:02 Prioritizing Features and Managing Expectations

27:07 Finding Common Ground Between Development and Finance

Takeaways

• We're entering the year of agent experimentation.
• Companies are building in-house AI solutions at nearly double the rate.
• The hype around AI is similar to blockchain, but for a real reason.
• Ecosystems are more important than ever.
• It's about creating interconnected frameworks. Successful ecosystems allow for seamless collaboration.
• Training architectures are evolving to work with what's possible.
• We're seeing a slowing pace of new AI capabilities.
• Bespoke solutions tailored to their needs are essential.

Takeaways

• Culture is about how leaders manage the business.
• Trust is essential for successful transformations.
• Engagement is linked to trust and productivity.
• AI can enhance employee experience significantly.
• Organizations need to define the business problem before adopting AI.
• Power skills will be crucial in the future job market.
• Human connection is vital in a tech-driven world.
• AI can help HR focus on human aspects.
• Leaders must align their actions with their words.
• Building trust requires transparency and consistency.

Chapters 00:00 Building AI-Friendly Cultures 03:24 The Role of Trust in AI Transformations 06:18 Tactical Approaches to Building Trust 09:02 AI's Impact on Employee Experience 11:56 Real-World Applications of AI in HR 15:13 Navigating AI Adoption Challenges 18:00 Power Skills in the Age of AI 21:03 The Future of Work and AI 24:04 Human Connection in an AI World 36:20 New Chapter

Takeaways

• AI can significantly improve the efficiency of engineering teams.
• The future of customer interactions may increasingly involve AI agents.
• Driving for dollars is a traditional real estate practice that can be optimized with AI.
• Using AI for lead scoring can help prioritize sales efforts effectively.
• AI can transform unstructured data into actionable insights for businesses.
• Call monitoring with AI can enhance quality assurance in customer interactions.
• The integration of AI into existing workflows can lead to substantial productivity gains.

Chapters

00:00 Introduction to AI in Real Estate

03:17 Driving for Dollars: AI in Property Assessment

06:10 Optimizing Marketing Efforts with AI

08:59 Lead Scoring: Prioritizing Sales Efforts

12:03 Enhancing Sales Processes with AI

15:05 Operational Efficiency: Call Monitoring and QA

19:06 The Future of AI in Customer Interactions

24:56 Integrating AI into Business Workflows

29:46 Conclusion and Future Outlook

36:51 New Chapter

Takeaways

• AI has the potential to revolutionize business processes.
• Understanding AI's limitations is crucial for effective implementation.
• Proprietary data is a key differentiator in the age of AI.
• AI should complement human tasks, not replace traditional computing.
• Businesses must identify unique processes to leverage AI effectively.
• AI can automate content generation and marketing strategies.
• AI can help in mapping data fields and automating processes.
• The integration of AI in business requires a clear understanding of value add.
• AI can enhance operational efficiency in various industries.
• Collaboration between AI, humans, and traditional software is essential for success.

Takeaways

• Chris emphasizes the importance of exploring various experiences to foster innovation.

• Product management is fluid and adapts to the organization's needs.
• Validation is a critical phase that often gets overlooked in product development.
• AI can help bridge the gap in legacy systems by providing insights and solutions.
• Building scalable software requires a clear understanding of business goals and user needs.
• Feedback from users is essential for improving software and ensuring it meets their needs.
• Curiosity drives the exploration of new technologies and solutions.
• Customization of SaaS products is key to addressing specific business challenges.
• Constraints can foster creativity and innovation in problem-solving.
• The journey of being a fractional CTO involves balancing technical delivery with personal freedom.

Books

• Range: Why Generalists Triumph in a Specialized World
• Kill It with Fire: Manage Aging Computer Systems (and Future Proof Modern Ones)

AI North Star Playbook

Chapters

00:00 Introduction to Chris Jaynes and His Journey

04:58 The Product Management Philosophy

10:08 The Importance of Validation in Product Development

15:19 Leveraging AI in Legacy Systems

20:57 Navigating the AI Landscape for Businesses

26:39 Balancing Technical Delivery and Leadership

32:08 Conclusion and Future Aspirations