This Week in Startups — FLASHBACK: The Future of Remote Work, Juggling APIs, and Dream Integrations with Wade Foster of Zapier | E2221

Podcast Host: Jason Calacanis
Episode Highlights: Future of work, automation, API strategies, remote work culture, and Zapier’s enduring influence
Key Guests: Wade Foster (Zapier), Lon Harris, Alex Wilhelm, Tomas Puig, Amulya Parmar
Date: January 1, 1970 (Flashbacks to 2016)

Episode Overview

This special episode of This Week in Startups is a look back at key startup and tech conversations, with a heavy emphasis on automation, the evolving nature of white-collar work, and the challenges and opportunities of building modern software platforms. The flashback centerpiece is Jason’s 2016 interview with Wade Foster, co-founder and CEO of Zapier, one of the pillars of workflow automation and remote-first work in SaaS.

The episode is bookended by contemporary discussions with founders like Amulya Parmar (Tour) and Tomas Puig (Alembic), further tracing the arc of automation, AI, and remote work from the early days of Zapier to today’s generative AI-powered startups.

Main Themes & Key Insights

1. The Automation of White-Collar Work

• Quasi-Coding & Democratized Scripting:
  Jason and Wade discuss how tools like Zapier are changing the complexion of clerical and white-collar work, empowering non-technical users to automate increasingly complex workflows (see key quotes below).

• The Future of Clerical Roles:
  Wade predicts a future where “quasi-coding”—basic scripting, macros, and automation setup—will become a baseline skill for the modern knowledge worker.

• Key Quote:

  “Now a savvy person could probably hire themselves out and pretend that they’re writing code, but it’s actually Zapier behind the scenes if they wanted to.”
  — Wade Foster [51:49]

2. API Realities: Platform Risk and Integrations

• API Volatility:
  The conversation explores the risks of building businesses atop constantly shifting third-party APIs, highlighting hard lessons from Twitter, Facebook, and LinkedIn.

• SaaS vs. Consumer Platforms:
  B2B APIs (like Salesforce) tend to be more stable and user-empowering than consumer platforms, which are beholden to ad buyers and frequently change access rules.

  • “If you rely heavily on one or two other companies’ API to build your company, and it’s sort of an unstable foundation, they can yank that API away at any time.”
    — Lon Harris [55:00]

• The Holy Grail of Integrations:
  Wade’s dream was Zapier’s full integration with Microsoft Office 365—a goal since realized in the present day.

  • “The world still runs on email and spreadsheets... just getting access to the world’s most popular email and spreadsheet tool is pretty exciting.”
    — Wade Foster [73:46]

3. Remote Work Culture: Ahead of the Curve

• Zapier as a Remote Pioneer:
  Zapier operated as a fully distributed team well before the COVID-19 pandemic normalized remote work. Their approach relied on digital trails, transparency, and asynchronous communication (via internal blogs and weekly “Friday updates”).

  • “People leave a digital trail right when they work these days... There is a digital trail of did you do this thing or not.”
    — Wade Foster [63:34]

• Internal Transparency:
  The practice of publishing internal weekly roundups democratized team awareness and enabled leaders to track output over presence.

• Remote Management Takeaway:
  “It’s not as rigidly like hour based as I think a lot of employers are... You can tell they got these five big tasks done today. And if you’re not looking at work that way, well, maybe you should be.”
  — Lon Harris [67:18]

4. Invisible Software: The Challenge and Power of Workflow Tools

• ‘Set It and Forget It’ Software:
  Zapier’s value is profound, but its invisible nature means that users often forget they’re leveraging it, prompting a need for client training and proactive onboarding (“concierge” services).

  • “I forget that I have it... it's an invisible tool. I don't have to log in to actually experience it. It’s just occurring in the background.”
    — Jason Calacanis [69:44]

• Education & Adoption:
  Zapier developed programs to help teams discover untapped automation opportunities—mirroring today’s AI onboarding and change management efforts.

5. Then vs. Now: Echoes Across a Decade

• Ten-Year Tech Echoes:
  The hosts repeatedly note how so many product challenges and philosophical debates from 2016 (automation, workflow friction, API instability, invisible tools) remain front-and-center today, though with a new AI twist.

  • “This sounds exactly like the conversation we're having today about automating white collar work using AI agents... I feel like we're having the same chat still.”
    — Alex Wilhelm [53:14]

Notable Quotes & Timestamps

| Timestamp | Speaker | Quote & Context | |-----------|----------------|-----------------------------------------------------------------------------------------------| | 51:49 | Wade Foster | “Now a savvy person could... pretend they’re writing code, but it’s actually Zapier behind the scenes.” — on democratizing automation | | 52:27 | Wade Foster | “I hesitate to say it’s coding, but it’s like quasi-coding... It’s basic scripting, macros...” | | 53:27 | Lon Harris | “The promise of a computer is going to get smarter to the point that it’s going to know... I should just do it for you.” | | 55:00 | Lon Harris | “If you rely heavily on one or two other companies’ API to build your company... they can yank that API away...” | | 63:34 | Wade Foster | “People leave a digital trail right when they work these days... There is a digital trail of did you do this thing or not.” — on remote accountability | | 69:44 | Jason Calacanis | “One of the things about Zapier I find is I forget that I have it... it’s an invisible tool.” | | 73:46 | Wade Foster | “The world still runs on email and spreadsheets... getting access to the world’s most popular email and spreadsheet tool is pretty exciting.” | | 67:18 | Lon Harris | “If you really think about it, you can tell who’s being productive, because everybody leaves a digital trail...” |

Important Segments & Timestamps

• Future of Work & Automation: [50:41] – [53:27]
  Deep exploration of how automation will transform knowledge work and what skills will rise in value.

• Platform/API Risks: [56:41] – [62:31]
  Candid discussion of why APIs from consumer platforms can’t be fully trusted and the business implications for SaaS.

• Remote Work Culture at Zapier: [63:19] – [68:29]
  Insights on distributed work, digital accountability, and remote management strategies years before they became the norm.

• Invisible Automation and Onboarding: [69:44] – [71:14]
  Discussion of how invisible automation tools require deliberate training and support to drive full adoption.

• Dream Integrations & Manifesting Growth: [73:27] – [75:45]
  Wade’s aspirations for Zapier’s integrations (notably Microsoft Office) and the narrative of “manifesting” SaaS success.

Memorable Moments

• Zapier’s Impact and Endurance:
  “It seems unthinkable that we would run our entire system without Zapier. It’s a fundamental building block of everything that Launch does.”
  — Lon Harris [76:14]

• On Remote Work Before It Was Cool:
  Zapier’s all-remote model, transparent communication, and asynchronous reporting were years ahead of the tech industry’s mainstream acceptance.

• Manifesting Microsoft:
  In 2016, Zapier’s ultimate wish was to integrate with Microsoft Office 365—a feat achieved well before many competitors could match.

Episode Takeaways

• Automation is Now Table Stakes:
  The journey from scripting and “quasi-coding” to today’s proliferation of AI agents reflects a decade-long drive toward frictionless digital workflows.

• Platform Dependency Remains a Core Risk:
  Building atop third-party APIs always comes with existential risks—a lesson continually learned as platforms rise, restructure, or close access.

• Remote Work is the New Normal:
  Zapier’s early distributed culture proved that output trumps physical presence, provided teams have transparency, digital accountability, and a culture of self-reporting.

• Education & Onboarding Outlast Product Launch:
  For invisible, horizontal tools, proactive customer education and services (concierge, onboarding) are essential to realize full value—a lesson today’s AI startups are relearning.

• Old Problems, New Wrappers:
  Many of today’s hot tech trends (AI, no-code, remote work) echo perennial issues—automating busywork, bridging platforms, and scaling distributed teams—now supercharged by new tools.

This episode is both a historical time capsule and a mirror reflecting today’s most pressing challenges in startup tech, automation, and remote work. As new platforms arise, some battles never change — except when they do, quietly, thanks to pioneers like Zapier.