Shipping Excellence

By Andrew Duncan

Welcome to Shipping Excellence, where action meets expertise. Hosted by Andrew Duncan, this podcast is all about building exceptional software products that don’t just exist—they deliver impact. Wi

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· Technology

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FAQs about Shipping Excellence:

How many episodes does Shipping Excellence have?

The podcast currently has 9 episodes available.

Shipping Excellence episodes:

August 26, 2025Is GenAI Digital Cocaine? Lessons from a CTO with Sergio Visinoni
In this episode of Shipping Excellence, Andrew Duncan sits down with Sergio Visinoni — a seasoned technology leader turned solopreneur, advisor, and fractional CTO. Sergio shares insights from his provocative article “Is GenAI Digital Cocaine?” and explores the parallels between generative AI, social media, and productivity hacks that may carry hidden costs.
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.
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30min
August 15, 2025From Startup Chaos to $50M: How Wonder Cave Built a World-Class Tech Team
What does it take to turn a struggling product launch into a $50M success? In this episode, Wonder Cave President Webb Bostick reveals the leadership moves, technical pivots, and team-building strategies that made it happen.
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.
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46min
January 31, 2025How AI Agents Will Reshape Business & Software Development w/ Drew Burdick
In this episode of Shipping Excellence, host Andrew Duncan sits down with Drew Burdick, Managing Partner of StealthX, and co-author of the AI North Star Playbook. They dive into how businesses should think about AI adoption, the rise of AI agents, and how solopreneurs and enterprises alike can leverage AI to drive efficiency and growth. The discussion covers everything from practical AI implementations, agentic workflows, the evolution of work, and the massive opportunities AI presents for early adopters.
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
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48min
January 06, 2025From CFO to CTO: Building High-Impact Teams with John Main
In this episode of the Shipping Excellence Podcast, Duncan speaks with John Main, founder of Farsight, about his journey from finance to technology leadership. John shares insights on building effective teams, navigating the challenges of product management, and the importance of aligning finance with development. He discusses his experiences at Modernizing Medicine and Strax, emphasizing the need for clear communication, prioritization of features, and maintaining team morale in high-stress environments. The conversation highlights the critical balance between innovation and resource management in tech startups.
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
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37min
December 29, 2024AI Hype vs. Reality: Lessons from 2024 and Predictions for 2025
In this episode, Andrew Duncan discusses the emerging trends in AI and software development as we approach 2025. He highlights the shift towards in-house AI solutions, the importance of ecosystems in maximizing AI's impact, and the evolving nature of training architectures. The conversation emphasizes the need for interconnected frameworks that foster collaboration and innovation in the tech ecosystem.
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.
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6min
December 27, 2024Building AI-Friendly Cultures w/ Malvika Jethmalani
In this episode of the Shipping Excellence Podcast, Andrew Duncan speaks with Malvika Jethmalani about the importance of building AI-friendly cultures within organizations. They discuss the critical role of trust in AI transformations, tactical approaches to fostering trust, and the impact of AI on employee experience. The conversation also covers how organizations can navigate AI transformations successfully, the significance of power skills in the age of AI, and the future of human connection in a technology-driven world.
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
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37min
December 20, 2024Transforming Real Estate sales w/ Jason Macht
Jason Macht discusses the transformative role of AI in the real estate sector. He shares real-world examples of how technology and data are being leveraged to optimize marketing, sales, and operational efficiency. From enhancing lead scoring to improving call monitoring, Jason emphasizes the importance of AI in driving business growth and efficiency. The conversation also touches on the future of AI in customer interactions and the ongoing evolution of technology in the business landscape.
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
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38min
December 13, 2024The Art of Validation in Software Development
In this episode of the Shipping Excellence Podcast, Chris Jaynes, a former VP of product and fractional CTO, shares his journey and insights into product management, the importance of validation in software development, and the role of AI in modern business. He discusses the challenges of navigating legacy systems, the significance of customer feedback, and the iterative process of building scalable software. Chris emphasizes the need for curiosity and customization in leveraging technology to solve real-world problems, while also reflecting on the personal challenges of being a fractional CTO.
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
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33min
December 06, 2024Harnessing AI for Business Success
In this conversation, Assaf Weinberg discusses the practical applications of AI in building technology and software products. He emphasizes the importance of understanding AI's capabilities and limitations, the role of proprietary data in business, and how AI can enhance operational efficiency and content generation. The discussion also highlights the need for businesses to identify their unique processes and data to leverage AI effectively.
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.
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21min

FAQs about Shipping Excellence:

How many episodes does Shipping Excellence have?

The podcast currently has 9 episodes available.