Podcast Summary: The Investor With Joel Palathinkal

Episode: John Lunn: Ex Paypal Ventures

Release Date: October 2, 2025
Host: Dr. Joel Palathinkal
Guest: John Lunn, ex-PayPal Ventures, serial entrepreneur

Episode Overview

In this episode, Dr. Joel Palathinkal sits down with John Lunn—veteran technologist, founding member of PayPal Europe, serial entrepreneur, and ex-head of PayPal Ventures. The conversation journeys through John’s unconventional entry into fintech, his career building and investing in payments and security companies, his lessons transitioning from building to investing, his philosophy on VC/founder relationships, and finally details of his new startup, Gravy, which is poised to disrupt payment orchestration for modern businesses.

Key Discussion Points & Insights

1. John’s Unorthodox Path Into Tech and Payments

• Early Background

  • John started as a marine biologist but found the job market bleak (02:19).
  • Pivoted to software, self-taught from books, and joined CyberSource, one of the first Internet payment companies (02:19–03:44).
  • “Like most things, it’s 90% luck, 10% being in the right place at the right time.” – John Lunn [02:19]
  • Early coding experiences included loading software from cassette tapes in Switzerland with his schoolteacher/jazz guitarist father (03:52).

• Career Highlights

  • Several startups: CyberSource (sold to Visa), Passmark Security (sold to RSA).
  • Joined PayPal Europe at its inception, became the tech lead, and helped scale its presence and influence (04:49–09:12).
  • “I spent 13 years at PayPal…went from the techie to running the lab, then being the ‘pretty face’ of PayPal in the media…” [07:53–09:12]

2. PayPal, Innovation, and the Move to Corporate VC

• Scaling at PayPal

  • Worked through eBay ownership, PayPal’s independence, and built products like mobile card readers and holographic window displays.
  • Led developer relations, growing PayPal’s DevRel community to 1.4 million developers (09:12–09:57).
  • Ran global hackathons and startup incubators.

• Building PayPal Ventures

  • Asked to start PayPal's venture arm: “I thought [my boss] was insane because I was a techie.” [09:57]
  • $350M AUM, early investor in fintechs like Plaid, Toss, Acorns.
  • “It’s easier to teach a techie to be a banker than a banker to be a techie.” – John Lunn [11:08 (paraphrased)]

• Why He Left VC

  • Loved supporting portfolio companies, less excited by the investing process.
  • “Deep down I knew I wanted to build myself again.” [11:33]
  • Immigration issues and desire to create led him to leave and form Gravy.

3. Insights on Transitioning from Builder to Investor

• Learning Curve for Techies in VC

  • “The biggest learning for me was there’s an awful lot of three-letter algorithms and descriptions…learning lingo, learning the words.” [12:07]
  • Leaned on his finance teammates and online resources rather than textbooks (19:27–20:55).
  • Emphasized the importance of good lawyers and finance personnel for due diligence (21:29–23:27).

• Reflections on Deal Flow and Founder Relations

  • Advised respect and humility: “If someone’s not got a good idea now, they might have a good idea tomorrow...Being a kind and respectful person, even with a dumb idea, is the right thing to do.” [15:03]

• Quote:

  • “There is this myth of the superstar VC...Most of how I’ve gotten where I’ve got has been luck. Be humble about it.” [18:05]

4. Human Side of Founders, Leadership, and Company Building

• Traits of Great Founders

  • Trust in their people, ability to bring teams along—not just being a stubborn visionary (25:40–27:02).
  • Avoid giving out inflated titles too early; maintain flexibility for scaling (27:02–28:47).
  • “Don’t give everyone a C-level job title…It actually hurts them because you can’t promote someone who’s a VP.” [27:14]

• Corporate Life vs. Entrepreneurship

  • Reflected on “the rut” of large companies: misallocation of time, the danger of comfort and titles, the value of time with family over career ladder climbing (31:20–36:46).
  • “If you’re not enjoying yourself at work, what the hell are you doing with your life?” [33:24]

5. Life and Tech in Vancouver & Canada

• Vancouver’s Tech Scene

  • Outsourcing hub, gaming-focused, less risk-taking than Toronto (39:10–41:26).
  • Toronto is the VC capital of Canada, with more deal flow and funding.
  • Insights on valuations: “There’s so much VC money in Canada, people are getting pretty large valuations…” [42:14]

• Inspirational note: Shopify’s Canadian roots encourage local entrepreneurship. Covid may trigger a new wave of ventures as people rethink career fulfillment (42:36–43:29).

6. Deep Dive: Gravy and the Future of Payments Orchestration (43:29–57:14)

• What is Payments Orchestration?

  • Analogy: Like the shift from manual cars to ultra-simplified modern cars, payments have gotten increasingly complex under the hood.
  • Merchants need to serve many payment types (cards, wallets, alternative payments)—especially globally.
  • “Why are people still building all this themselves? Why is there not a software that allows a merchant to control where its payments go?” [46:39–48:00]

• How Gravy Works

  • Universal API for payments, plus a no-code workflow platform to easily add and manage payment methods without developer bottlenecks.
  • Enables merchants to avoid “technological hostage” situations—can route traffic across payment processors for cost, redundancy, or access (48:00–52:00).
  • “Payments are a massive tax on your business…it’s amazing how saving half a percent can be huge.” [48:00]

• Technical Approach

  • Built on Kubernetes; scalable from startups to enterprise.
  • Focused on mid-sized merchants for initial go-to-market.
  • “We’re pricing ourselves like a cloud company, not like a payments company.” [55:51]

7. Audience Q&A and Final Closing Themes (57:14–61:30)

• Dealing with Bootstrapping Pressure

  • “Set yourself a timeline. Say, ‘If it’s not happened by this time, I’ll get a real job.’” [57:34–58:46]

• Super Apps and Payments Convergence

  • “Super apps will exist in their ecosystems but…they’re not going to converge. Our belief: you need glue in the middle so that it can be navigable—that’s what we’re building.” [59:52–60:34]

Notable Quotes & Memorable Moments

• “It’s easier to teach a techie to be a banker than a banker to be a techie.” – John Lunn [Paraphrased, 11:08 & referenced throughout]
• “Be honest and kind…Even if you’re not going to invest, try to help as much as you can.” – John Lunn [16:50]
• “No one ever said on their deathbed, ‘I should have worked more.’” – John Lunn [34:31]
• “Why are people still building all this [payments tech] themselves? Why is there not software to control payments?” – John Lunn [46:39]
• “Payments are a massive tax on your business…Saving half a percent is huge.” – John Lunn [48:00]
• “We're pricing ourselves like a cloud company, not like a payments company.” – John Lunn [55:51]

Timestamps for Important Segments

• John’s career origin story & transition to tech: 02:19–03:44
• Joining CyberSource & early Internet payments: 02:19–04:49
• Founding PayPal Europe & innovations: 07:53–09:12
• Leading PayPal Ventures: 09:57–11:33
• Frameworks for learning VC as a techie: 12:07–15:03
• Traits of great founders: 25:40–28:47
• Reflections on titles, corporate rut, and family: 31:20–36:46
• Vancouver & Canadian tech scene: 39:10–43:29
• Payments orchestration & Gravy deep dive: 46:39–57:14
• Advice on bootstrapping & mental health: 57:34–58:46
• Super apps & global payments ecosystem: 59:52–60:34

Conclusion

This episode offers a rich, wide-ranging perspective on the evolution of tech careers, building versus investing, and the future of payments. John Lunn’s advice is candid and humble, emphasizing kindness in venture, the critical importance of building the right teams, and the seismic impact that new payment infrastructure—like Gravy—could have on global commerce. The episode will prove valuable for technologists eyeing investor roles, current and aspiring founders, and anyone exploring the shifting landscape of fintech innovation.