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

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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

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In this bonus episode of The Room Podcast, we speak with Ben Ling, Founder and General Partner of Bling Capital, an early-stage venture firm that has backed companies including Airtable, Lyft, Square, Palantir, and many others. Before becoming a full-time investor, Ben held leadership roles at Google, Facebook, and YouTube, where he helped build products at massive scale and gained a front-row seat to some of the most important technology platforms of the last two decades.

In this rendition of Founding the fund, Ben shares lessons from moving between operating and investing, what he learned working alongside leaders like Vinod Khosla and Marissa Mayer, and why distribution often matters more than product. We also discuss how Ben built Bling Capital around founder experience, why seed investing has structural advantages over multi-stage funds, how venture investors should think about trillion-dollar outcomes instead of billion-dollar outcomes, and the framework he uses to evaluate both founders and aspiring fund managers.

Learn more about Ben on LinkedIn - https://www.linkedin.com/in/benjaminling
And Bling Capital on their website - https://blingcap.com

(06:12) Ben Ling's upbringing between Taiwan and the United States
(07:03) Did Ben always know he wanted to become a founder?
(07:51) Lessons from Google, Facebook, and YouTube on scaling products
(10:45) Why Ben started angel investing
(12:30) What is the modern equivalent of being the "platform insider"?
(13:35) Why Ben joined Khosla Ventures
(16:24) Angel investing versus institutional venture capital
(18:25) Developing conviction as an investor writing larger checks
(22:42) Lessons learned from working with Vinod Khosla
(25:21) Why Ben started Bling Capital
(28:10) Building a founder-first venture firm
(30:51) The first founder and LP who backed Bling Capital
(33:24) Maintaining investment conviction through market cycles
(34:32) Building the team at Bling Capital
(36:00) What Ben looks for when hiring investors
(38:07) How Bling Capital has evolved over time
(40:25) What makes investor-founder relationships durable
(45:37) Advice for aspiring fund managers
(47:00) What Ben is excited about next
(47:24) A woman who had a profound impact on Ben's life and career

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In our season finale episode of The Room Podcast, we speak with Jamie Siminoff, inventor of Ring, the smart home security company best known for turning the front door into a connected safety platform. Ring builds video doorbells, cameras, alarms, and neighborhood safety tools that help people monitor and protect what matters most.

Before Ring became one of the most recognizable home security brands in the world, Jamie was an inventor building things in his basement, launching companies like PhoneTag and Unsubscribe.com, and learning firsthand that a great product does not always equal a great business. His career has spanned consumer hardware, software, home security, AI-enabled safety tools, and one of the most memorable startup journeys from Shark Tank rejection to Amazon acquisition.

In this conversation, Jamie shares the core insight behind Ring: the company was never really about doorbells; it was about making neighborhoods safer. What started as a personal frustration in his garage became a mission-driven company after his wife said the prototype made her feel safer at home.

We also discuss:
• Why timing matters when building hardware
• The brutal reality of venture dilution and capital-heavy businesses
• Going from $70 million in debt to a billion-dollar Amazon acquisition
• Why AI needs hardware “appendages” to impact the real world
• How Ring thinks about privacy, surveillance concerns, and community safety
• Why founders should look for the “infinite truth” behind what they are building

(05:30) Jamie’s childhood and early inventor mindset
(06:18) Whether Jamie always saw himself becoming a founder
(06:57) Building PhoneTag and learning from voicemail-to-text
(07:52) The idea behind Unsubscribe.com
(08:56) Realizing Ring was more than a personal annoyance
(11:30) The product unlock that made Ring innovative
(13:34) Surprising customer use cases that shaped Ring’s roadmap
(14:41) When Ring launched and how social video was emerging
(16:12) The first investor who believed in Ring
(17:19) Turning down Kevin O’Leary on Shark Tank
(18:35) Going from $70M in debt to the Amazon deal
(21:16) Advice for founders raising venture capital
(24:27) How AI is changing the future of hardware
(25:45) Expanding Ring beyond the original doorbell product
(28:56) Ring’s role in the broader neighborhood safety ecosystem
(31:28) Why Jamie decided to write Ding Dong
(33:26) Why Amazon was the right next chapter for Ring
(35:21) Leaving Amazon, building Door.com, and returning to Ring
(37:20) Balancing AI innovation with privacy concerns
(42:14) A woman who had a profound impact on Jamie’s life and career

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Brought to you by Rippling and Perkins Coie.

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In this episode of The Room Podcast, we speak with Scott Stevenson, CEO and Co-Founder of Spellbook. Spellbook is an AI-powered platform helping lawyers draft and review contracts faster using generative AI directly within their existing workflows.

Spellbook enables legal teams to accelerate contract creation and negotiation by embedding AI into workflow tools allowing for real-time drafting, editing, and comparison against market data. The company sits at the intersection of legal tech and AI infrastructure, transforming how contracts are created by shifting from slow, manual workflows to intelligent, data-driven systems. This conversation explores how startups are fundamentally a pursuit of truth, how AI is reshaping legal work, and why building enduring companies requires deep conviction in a problem over many years.

Scott shares the core insight behind Spellbook: lawyers don’t need entirely new tools. Rather, they need dramatically better versions of what they already use, seamlessly integrated into their workflow.

We also discuss:
• Growing up in Newfoundland and developing an outsider’s perspective on innovation
• The philosophical lens of “competitive truth-seeking” in startups and investing
• Why early product iterations failed despite traction and how the team stayed disciplined on product-market fit
• The generative AI breakthrough moment inspired by GitHub Copilot
• Why most vertical AI companies overcomplicate their tech stack and how leveraging foundation models creates leverage

Learn more about Scott on LinkedIn and explore Spellbook at https://www.spellbook.legal/

(03:13) Scott’s background growing up in Newfoundland
(05:13) Did Scott always see himself becoming a founder?
(05:58) Scott’s philosophy background and metaphysical idealism
(12:13) How music and creativity led to Scott’s first company
(14:33) Why Scott chose to build in legal tech
(16:13) How Scott navigated early product-market fit struggles
(18:23) The pivot moment into generative AI
(22:33) Who was Scott’s first investor?
(24:43) What drove the early growth and waitlist explosion
(27:43) How Spellbook thinks about its tech stack and AI strategy
(30:43) What’s next for Spellbook
(34:03) A woman who had a profound impact on Scott’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!

Brought to you by Rippling and Perkins Coie.

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In this episode of The Room Podcast, we speak with Ram Palaniappan, founder and CEO of Earnin, a fintech company reimagining how people get paid by giving employees access to their earnings in real time rather than waiting for traditional payroll cycles.

Earnin is building a new kind of payroll system—one that shifts power from employers to employees by enabling on-demand and continuous pay. Instead of the outdated two-week batch system, Earnin is pioneering a streaming model for income, where workers can access wages as they earn them, improving financial stability and reducing reliance on overdrafts and late fees.

Ram’s journey into founding Earnin didn’t begin with the intention to start a company—it began by manually helping employees avoid overdraft fees by advancing their earned wages. That scrappy, human-first solution evolved into a scaled fintech platform now used by millions, reshaping how payroll is experienced across the U.S.

In this conversation, Ram shares the core insight behind Earnin: payroll is fundamentally a broken digital product, and like all digital systems, it should evolve from batch processing to real-time streaming.

We also discuss:
• Why payroll has remained one of the last “batch-based” systems in a real-time world
• The infrastructure behind streaming wages second-by-second
• Lessons from navigating COVID when usage dropped 60% almost overnight
• How Earnin used capital to forgive millions in consumer debt
• Why giving employees control over pay improves income, attendance, and financial outcomes

Learn more about Ram on LinkedIn and explore Earnin at https://www.earnin.com/

(04:55) Ram’s childhood and early experiences growing up in India
(06:40) Whether Ram always saw himself becoming a founder
(08:12) The fintech landscape when Earnin was first being built
(09:58) Why payroll has remained a batch-based system
(11:12) The transition from RushCard to launching Earnin
(12:42) The infrastructure behind real-time and streaming payroll
(15:57) The first investor who backed Earnin
(16:43) A defining moment when things did not go as planned
(17:49) The decision to buy and forgive user debt
(19:04) How Earnin thinks about equity vs. debt financing
(20:01) How AI is changing how Earnin builds and ships products
(21:05) How consumer fintech is evolving alongside AI
(22:17) How Earnin helps employers better support employees
(24:19) How government and regulation are catching up to earned wage access
(25:51) A woman who had a profound impact on Ram’s 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!

Brought to you by Rippling and Perkins Coie.

WX Productions

In this episode of The Room Podcast, we sit down with Ben Witte, Founder and CEO of Recess, a consumer wellness brand pioneering a new category of functional beverages designed to help people relax, unwind, and feel better in an increasingly high-stress world. Recess blends ingredients like magnesium, adaptogens, and other functional compounds into beautifully branded drinks that position themselves as the “Red Bull for relaxation.”

Before launching Recess, Ben built his career in early-stage startups and hypergrowth companies like AdRoll, where he developed a deep understanding of digital marketing, brand building, and emerging consumer trends.

In this conversation, Ben shares the core insight behind Recess: that relaxation would define the next major consumer category, driven by rising anxiety, changing alcohol consumption habits, and a cultural shift toward mental wellness. We dive into lessons on identifying non-obvious trends early, building a lifestyle brand in a crowded CPG market, and navigating major challenges like regulatory uncertainty and COVID-driven disruption. Ben also unpacks his philosophy on category creation, why great brands market outcomes instead of ingredients, and how founders should think about fundraising, timing, and long-term vision when building enduring companies.

We also discuss:
• How Recess validated product-market fit through user behavior
• Building a brand-first flywheel using digital and DTC channels
• Navigating the CBD regulatory crisis and COVID simultaneously
• Fundraising strategy in capital-intensive categories like beverages
• The long-term evolution of alcohol moderation and non-alcoholic drinks

Learn more about Ben on LinkedIn and explore Recess at https://takearecess.com/

(04:59) Ben Witte’s childhood and early influences
(05:24) Whether Ben always saw himself becoming a founder
(06:15) Early career and entry into startups through AdRoll
(08:36) The aha moment behind starting Recess
(11:16) Choosing adaptogens and betting on the relaxation trend
(13:54) Early signs of product-market fit for Recess
(15:57) Building the initial marketing flywheel and go-to-market strategy
(18:04) The first investors who backed Recess
(18:43) Fundraising strategy in a modern CPG environment
(20:30) A major challenge and unexpected twist in building Recess
(23:59) Scaling operations and evolving the supply chain
(34:15) Ben’s favorite Recess products and flavors
(34:28) What’s next for Recess and Ben personally
(34:45) Perspective on alcohol moderation and consumer behavior trends
(35:51) A woman who had a profound impact on Ben’s life and career

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

Brought to you by Rippling and Perkins Coie.

WX Productions