In this bonus episode of The Room Podcast, we speak with Jai Das, President, Partner and Co-Founder of Sapphire Ventures, one of the world's leading enterprise venture capital firms backing category-defining B2B software and AI companies.

Sapphire Ventures has invested in companies including monday.com, Box, Square, MuleSoft, Fitbit, ExactTarget, and many others, while building one of the industry's most recognized enterprise-focused venture platforms. Before co-founding Sapphire Ventures, Jai's career spanned software engineering at Oracle, founding startups during the dot-com era, corporate venture investing, and leading the transformation of SAP Ventures into the independent firm it is today.

In this conversation, Jai reflects on the lessons learned across multiple technology cycles, from the early internet to today's AI revolution, sharing how his experiences as an engineer, founder, and investor shaped Sapphire's long-term strategy and investment philosophy.

Learn more about Jai on LinkedIn - https://www.linkedin.com/in/jaidas
Explore Sapphire Ventures on their website - https://sapphireventures.com/

(05:38) Jai's upbringing in India and journey to Silicon Valley
(08:20) Did Jai always think he would become a founder
(09:37) What was it like being an engineer at Oracle in the 1990s?
(11:51) Did Oracle miss its opportunity in cloud computing?
(13:10) Jai’s startup journey after Oracle and the path to SAP Ventures
(17:53) How did Jai’s first venture investing experience shape your career?
(18:50) What was early corporate venture capital like at Intel and SAP?
(20:57) How should founders think about taking money from corporate VCs?
(23:33) How did SAP Ventures become Sapphire Ventures?
(25:06) How did Sapphire differentiate itself in a crowded VC market?
(28:19) When did Sapphire experience its biggest growing pains?
(32:40) Who was Sapphire Ventures' first LP?
(34:18) Why did Sapphire build a fund-of-funds strategy?
(35:59) What was the first portfolio company that believed in Sapphire?
(37:37) Why has the developer become such an important buyer?
(39:58) How has AI changed who the modern "developer" really is?
(41:50) How does the rise of AI agents influence your investment thesis?
(44:42) How does venture capital stay relevant in the age of AI?
(48:11) What is Jai most excited about right now?
(49:37) Who is a woman that has had a profound impact on Jai’s life and career?

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In this bonus episode of The Room Podcast, we speak with Packy McCormick, founder of Not Boring and Not Boring Capital, an investment firm focused on backing ambitious technology companies tackling large, complex industries. Through his writing, investing, and storytelling, Packy has built one of the most influential platforms in venture capital, helping founders explain difficult technical businesses to customers, talent, and investors.

Not Boring began as a newsletter during the early months of the pandemic and has since grown into a media platform reaching hundreds of thousands of readers, alongside an early-stage venture fund investing in companies across energy, aerospace, infrastructure, AI, and enterprise software. Rather than chasing trends, Packy focuses on founders building category-defining businesses that require deep conviction and long-term thinking.

In this conversation, Packy shares how storytelling became his competitive edge as an investor, why the best founders think several moves ahead of everyone else, and how developing a unique perspective can create opportunities that traditional venture firms often overlook.

Learn more about Packy on LinkedIn: https://www.linkedin.com/in/packymccormick/
Explore Not Boring at https://www.notboring.co/

(04:11) Packy's upbringing and entrepreneurial family
(05:01) Did Packy always think he would become a founder?
(05:50) Early career in finance and startups
(09:16) Starting Not Boring during the pandemic
(12:48) The first article that proved Not Boring was working
(14:04) Growing the newsletter and launching Not Boring Capital
(15:57) The thesis behind Not Boring Capital
(17:23) The first investor to back Not Boring Capital
(17:48) What Packy looks for in exceptional founders
(21:57) Building a venture firm around a personal platform
(23:56) The future of venture capital
(26:36) How storytelling creates an investing advantage
(28:45) Investing in complex businesses
(31:08) An investment that didn't go as planned
(33:19) How AI is changing writing and investing
(35:23) Advice for building an audience today
(37:05) What's next for Not Boring
(38:20) A woman who had a profound impact on Packy's life and career

For The Room Podcast in your inbox every week, subscribe to our newsletter.
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Check out our guide to podcasting here!
Don't forget to subscribe to our channel on YouTube, Spotify, and Apple Music!

WX Productions

In this episode of The Room Podcast, we speak with Sunil Dhaliwal, founder and managing partner of Amplify Partners, an early-stage venture capital firm focused on backing technical founders building infrastructure software, developer tools, cybersecurity, AI, and other foundational technologies. Before founding Amplify, Sunil spent 14 years at Battery Ventures, where he invested through both the dot-com boom and bust before launching Amplify in 2012, which today manages more than $2.7 billion in assets.

In this conversation, Sunil reflects on the entrepreneurial influence of his parents, lessons learned investing through multiple technology cycles, and the conviction that led him to build Amplify around technical founders long before the rest of the venture industry caught on. We also discuss why venture firms need a clear reason to exist, how long-term relationships become your greatest fundraising advantage, what separates durable investors from emerging managers, why founder "fit" matters more than pattern matching, how technological shifts create entirely new categories of entrepreneurs, and the importance of staying early to transformational markets even when the timing isn't immediately obvious.

Learn more about Sunil on LinkedIn: https://www.linkedin.com/in/sunilnagaraj/
Explore Amplify Partners at https://www.amplifypartners.com/.

(05:52) Sunil's childhood and growing up in Rochester, New York
(08:09) Did Sunil always think he would become a founder?
(09:22) Transferring from Rochester to Georgetown
(11:39) The story behind Sunil's transfer from Rochester to Georgetown
(11:55) Discovering venture capital after college
(15:10) Lessons from investing through the dot-com boom and bust
(16:58) The insight behind founding Amplify Partners
(20:27) The first investor who backed Amplify
(23:13) Starting a venture fund then versus today
(27:09) Bringing Mike Dauber on as a partner
(29:43) How Amplify evaluates technical founders
(32:47) The characteristics of exceptional founders
(36:00) Why founder-market fit matters more than pattern matching
(38:46) A portfolio company that changed Sunil's perspective
(41:25) Why infrastructure investing requires patience
(44:38) How AI is changing venture investing
(48:58) Areas of AI Sunil is most excited about
(52:17) Advice for aspiring venture capitalists
(55:04) Advice for founders raising their first round
(57:56) A moment when Sunil's conviction was tested
(01:00:47) What keeps Sunil motivated after nearly three decades in venture
(01:03:07) Someone who had a profound impact on Sunil's life and career

For The Room Podcast in your inbox every week, subscribe to our newsletter.
Follow us on Instagram
Follow us on TikTok
Check out our guide to podcasting here!
Don't forget to subscribe to our channel on YouTube, Spotify, and Apple Music!

WX Productions