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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WX Productions

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

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 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.
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!

Brought to you by Rippling and Perkins Coie.

WX Productions