Jan 2, 2019 · 32m · a16z
a16z Podcast | The Future of Software Development
Steven Sinofsky · 9m spoken Matthew McCullough · 5m spoken Roger Dickey · 5m spoken Joel Spolsky · 4m spoken Bill Macaitis · 3m spoken Michael Copeland · 57s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Hosted by Steven Sinofsky, this a16z podcast panel features industry executives from Slack, GitHub, Stack Overflow, and Gigster discussing the growing demand for custom software, evolving developer learning and hiring practices, open-source governance, and the changing role of enterprise IT.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
The host as informed peer 3.4 Guest teaching 3.9 Guest disagreement 1.9 The host pushing back 2.7
speaking balance: gold is the host, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 30:51 Rejecting Universal Coding Mantra
Roger Dickey explicitly challenges the popular press narrative that everyone should learn to code, clarifying that true software literacy is about process-driven thinking.
Hardest push from the host ▶ 4:31 Challenging CIO Procurement FramingSteven Sinofsky explicitly refuses Bill Macaitis's framing of the CIO as a pricing negotiator, pushing him to address where technical architecture and security fit into the role.
Biggest teaching moment ▶ 12:59 Page Faulting Knowledge ConceptJoel Spolsky educates the host on modern developer behavior, explaining that engineers no longer study documentation upfront but 'page fault' knowledge directly from search engines into code.
The host holds their own ▶ 7:57 Enterprise Open Source RealitySteven Sinofsky leverages his personal experience leading Windows development at Microsoft to confirm that even the largest proprietary software companies unknowingly rely heavily on open source.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The host as informed peer | Guest teaching | Guest disagreement | The host pushing back | Why |
|---|---|---|---|---|---|---|
| Evolution of SaaS Distribution and the CIO's Role | 4 | 2 | 1 | 4 | Sinofsky actively directs the discussion on SaaS distribution models and explicitly pushes Macaitis on the distinction between pricing negotiations and core technical architecture for CIOs. Macaitis constructively clarifies how procurement and IT security functions divide responsibilities. | |
| Scale, Security, and Governance of Open Source Software | 4 | 3 | 2 | 4 | Sinofsky interjects with executive insight from Microsoft regarding enterprise open source adoption, then presses McCullough on community friction and code review burden. McCullough explains how open source governance has shifted into emotional management of external collaborators. | |
| How Modern Developers Learn and Public Portfolios as Resumes | 3 | 5 | 1 | 2 | Spolsky educates the host on how modern developers learn by 'page faulting' knowledge through search engines rather than reading upfront manuals. McCullough adds how GitHub commit histories replace traditional resumes when evaluating talent. | |
| Addressing the Software Demand Gap with Gigster | 3 | 4 | 2 | 2 | Sinofsky sets up the enterprise supply-and-demand dilemma for software development, allowing Dickey to explain Gigster's model. Dickey contrasts developer psychology with traditional freelancing using an Uber-style isolation analogy. | |
| Developer Culture, Side Projects, and Community Motivations | 3 | 4 | 1 | 1 | The panel explores side-project culture in Silicon Valley, with Macaitis recounting Slack's origins from a gaming company. McCullough frames developer motivation via Maslow's hierarchy while Spolsky describes the psychological drive to help peers online. | |
| Managing Code Accountability, Security, and SaaS Integrations | 4 | 5 | 3 | 4 | Sinofsky presses the panel with a direct question regarding accountability when developers copy bug-ridden code from online sources. Spolsky reframes rigid top-down accountability into a biological, statistical view of enterprise code risk. | |
| Software Engineering as a Modern Form of Literacy | 3 | 4 | 3 | 2 | When Sinofsky asks if coding is the new universal literacy, Dickey pushes back against popular media narratives, arguing literacy means understanding logical process rather than writing syntax. Macaitis highlights how low-code integrations empower non-developers. |
Statements from this episode (16)
Macaitis: Slack's freemium tier supports 2,000 users without time limits
“We have a freemium model where it is not, the trial is not time-bound or user-bound, so you can have 2000 people on it can be free”
Macaitis: Bottom-up software adoption beats upfront seven-figure enterprise contracts
“And I think ultimately it's better for the customers and the companies because they're not signing these seven-figure deals and not even knowing if this stuff works or not. You know, you're doing test beds and small companies and teams validating that the valu…”
McCullough: GitHub hosts 35 million projects and 11 million users
“We're talking about thirty-five million projects right now, and eleven million users.”
Sinofsky: Even major proprietary software companies secretly use open source code
“That is actually true even in the world's most largest proprietary software company.”
McCullough: Prioritize speed to market over keeping source code secret
“I say that you're actually better to think about how quickly you can release product to market and less focus on trying to keep your code Close to the vest and inside.”
Spolsky: Modern developers learn by page faulting knowledge, not reading manuals
“We think is that people have given up from learning a priori how to use the programming environments that they're working in. They don't even read a book, let alone the documentation. I think they start by writing code or by cutting and pasting code. They don'…”
Spolsky: Hiring programmers requires evaluating public portfolios like GitHub and Stack Overflow
“It's really looking at a programmer's public work now that's relevant. And so just like you wouldn't hire a designer without looking at a portfolio that they brought, brought you when you're hiring a programmer today, you're likely to look at the, Open source …”
Dickey: Top developers only work for Google or start companies
“The best developers want to work for a visionary inspiring company like Google, or they want to go start their own company.”
Dickey: Clients start $40K projects within two hours on Gigster
“We've seen people start 40,000 dollar projects after being on the website for just two hours, and that's not exceptional.”
Dickey: Gigster has 200 active software projects running simultaneously
“Whenever we start a new project, we have 200 projects going on right now, we start a new private room in Slack so that the team can collaborate.”
Macaitis: Slack is the fastest-growing messaging app in history
“And here it is kind of being the fastest growing messaging app ever.”
Spolsky: Open-source software is driven by developers' motivation to help others
“If you can do three minutes of work to answer something that maybe 10 people in the world know the answer to, and you can save somebody hours and hours of discovery, there's almost no stronger force than the motivation to help that person. And it's especially …”
Spolsky: Enterprise code risk should be managed biologically and statistically
“At some point, you start to treat the units that you're dealing with as either atomic agents, which is, all right, fine. People are bringing in iPhones. I don't actually know what code is running on those iPhones. Up to almost biological, where you start to th…”
McCullough: Bad code has no provenance, good code has many authors
“Bad code has no provenance, and good code everyone wants to claim credit for.”
Spolsky: 40M people write software monthly, vs 9M professional developers
“When we started building Stack Overflow we did a lot of research on how many software developers there were in the world, and the conclusion seems to be nine million people that call themselves software developers in the world, and we had at the time six milli…”
Dickey: Process-driven engineering mindsets make engineers effective company founders
“One of the reasons that engineers tend to make good founders is because engineers think in a certain way. So, you know, I think, ah, understanding at least how engineers think and being able to think in that same kind of process-driven and logical way helps ev…”