At sixteen, Jeff Barr was supposed to be opening boxes at a small computer store in Seattle. Instead, customers kept getting sent to “the long-haired kid in the corner,” because he was the only one who actually understood what the machines could do.

That instinct, deep curiosity paired with a need to explain things clearly, would quietly shape the future of cloud computing.

In this episode of the Ignite Podcast, we sit down with Jeff Barr, Chief Evangelist at AWS and one of the earliest voices behind cloud, long before “serverless” was a buzzword. Jeff walks through his improbable career path, from teenage computer shops and early web services, to the moment a tiny “Amazon now supports XML” message pulled him into what would become AWS.

We talk about how the cloud really started, why APIs mattered more than anyone realized at the time, and how AWS grew not just through technology, but through trust, clarity, and a global developer community that changed lives far beyond Silicon Valley.

The conversation also dives into the AI era, how developer skills are shifting, why reading code may matter more than writing it, and what happens when building software becomes cheap but understanding problems remains hard.

If you’re a founder, developer, or investor trying to make sense of where cloud and AI are actually headed, this episode is a grounded, human look at how big technology shifts really happen, slowly, accidentally, and driven by people who couldn’t stop being curious.

In Today's Episode We Discuss:

00:01 – Welcome to the Ignite Podcast

00:45 – A Teenager, a Computer Store, and the Birth of Curiosity

02:45 – Learning by Reading the Manuals (Literally)

04:10 – From Retro Computers to Real Engineering

05:45 – Startups, Microsoft, and the Pain of Big Companies

07:30 – Web Services Before They Were Cool

09:50 – The Accidental Discovery of Amazon APIs (2002)

11:30 – The First AWS Developer Conference (Before AWS Existed)

13:30 – “I Have to Be Part of This”

15:00 – Joining Amazon at Its Lowest Point

17:00 – Inside Early AWS: Less Structure, More Vision

19:15 – Becoming the First AWS Evangelist

21:00 – Launching AWS Through a Blog (A Radical Idea in 2004)

24:00 – Writing for Developers, Not “Enterprise Speak”

27:30 – 20 Years, 3,300 Posts, and 150+ Service Launches

30:00 – AI Coding Assistants Are Just Another Tool

33:00 – Reading Code Is the New Writing Code

35:45 – re:Invent Takeaways: Community Over Everything

38:30 – How Cloud Skills Change Lives Globally

41:15 – The “One-Person Unicorn” Thesis

43:45 – From Infrastructure to Agentic Applications

46:15 – Disposable Apps, Durable Data

49:00 – The Developer of the Next Decade

51:30 – Jeff Barr’s Legacy

53:15 – Closing Thoughts

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Dorothy Li is the co-founder and CEO of The Real Roots, a startup designing IRL, guided, matched experiences to help adult women build real friendships. With years in mission-driven startups—and a founder’s obsession with “what actually works in real life”—she’s tackling loneliness as a solvable systems problem, not a personal failing.

With a clear read on why loneliness got louder after the pandemic—and why it suddenly became socially “okay” to admit it—Dorothy offers insights into modern community-building, the science (and art) of compatibility, and how AI can scale nuance without turning humans into spreadsheets.

In this episode, she discusses why “friendship products” fail when they stop at matching, how Real Roots engineers the conditions for closeness (compatibility + repeated contact + facilitated depth), and what she learned by concierge-running the first groups herself—before tech (and later, voice AI) made the model scale.

In Today’s Episode We Discuss:

00:01 Why Adult Friendship Feels So Hard

01:42 Dorothy Li’s Path to Building The Real Roots

04:12 Loneliness Isn’t New—It’s Just Finally Admitted

06:38 Why Friendship Was Never Properly “Designed”

08:55 The Failure of Matching-Only Friendship Products

11:06 What Actually Creates Closeness Between Strangers

13:18 What You Can’t Self-Report (But Matters Most)

15:34 Early Proof: When Friendships Really Stick

18:06 Men vs Women: Different Paths to Bonding

20:11 Inside The Real Roots Experience

22:57 Why Facilitation Changes Everything

25:04 Designing for Repetition, Not One-Offs

27:09 Scaling IRL Without Killing the Magic

29:41 Building a City-by-City Marketplace

32:08 What Growth Actually Looks Like Early On

35:02 The Awkward Phase Everyone Wants to Skip

37:40 The Founder Trap: Waiting Until You’re ‘Ready’

41:12 How AI Finally Made This Scalable

44:10 The Metrics That Actually Matter

47:36 What’s Next for The Real Roots

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

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Udi Ledergor is the Chief Evangelist and former CMO at Gong, where he helped define an entirely new category in B2B SaaS and turn a call-recording idea into a global revenue platform. He started in Tel Aviv’s performing arts scene, moved through product management and multiple head-of-marketing roles, and has spent 20+ years turning complex tech into stories people actually care about.

With a background that blends stagecraft, magic, and enterprise GTM, he offers hard-won insights into category creation, demand gen vs product marketing, hiring for potential, and how to make even your privacy-policy email memorable. In this episode, he discusses the real story behind “revenue intelligence,” his framework for your first marketing hires, why courageous marketing requires psychological safety, and why email stubbornly remains the most underpriced B2B channel.

In Today’s Episode We Discuss:

00:01 Welcome & Introducing Udi Ledergor

00:42 Growing Up Performing in Tel Aviv

02:08 From Computer Science to Product and Marketing

03:56 Leadership, Trust & Creative Risk-Taking

06:15 Product vs GTM: Building a Winning Engine

07:12 Gong vs Competitors: Small Edges, Big Outcomes

11:48 The “Quarter From Hell” & Gong’s Origin Story

14:20 Why the Shift from Conversation Intelligence to Revenue Intelligence

18:45 Breaking Through with Courageous Marketing

21:58 Data, Storytelling & When to Reveal the AI

24:37 Early-Stage Marketing Mistakes Founders Make

26:32 Udi’s Framework for Hiring Your First Marketer

29:50 The Missing Role: Product Marketing & Enablement

31:58 Writing Courageous Marketing & Its Core Message

34:22 Creating a POV That Polarizes (In a Good Way)

36:40 Turning a Privacy Email into a Brand Moment

38:57 Mascots, Dogs & The Hidden Layers of Brand

41:25 Hiring for Potential, Not Pedigree

44:09 How Udi Advises Startups as an Angel

46:52 The Underrated Power of Email in B2B

49:28 Lessons from Writing a Nonfiction Book

52:10 What’s Next for Udi & The Future of Revenue AI

53:02 Closing Thoughts & Episode Wrap-Up

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/ignite-conversations-on-startups-venture-capital-tech/id1709248824

Follow Udi Ledergor on LinkedIn: https://www.linkedin.com/in/udiledergor/

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Visit Our Website: https://www.teamignite.ventures

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👂🎧 Watch, listen, and follow on your favorite platform: https://tr.ee/S2ayrbx_fL

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