Ben Gilbert

Co-Founder and Managing Director, PSL Ventures, PSL Ventures
Ben Gilbert, founder-turned-media entrepreneur and co-founder of a startup studio, runs the Acquired podcast and uses month-long deep dives as a community research engine for deal sourcing and pattern recognition.
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USA
Ben Gilbert
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AI
SaaS
Consumer
Fintech
Proptech
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About Ben Gilbert

Ben Gilbert is a technical founder turned media entrepreneur who co-founded Pioneer Square Labs, a startup studio that systematically generates and spins out companies, while also running the tech podcast Acquired full-time as his primary venture. He uses Acquired as an investing research engine, conducting month-long deep dives into companies that function as an ongoing strategy seminar, sharpening his pattern recognition while building a community-centric platform that creates deal flow and sourcing opportunities for his work at PSL Ventures.

Ben Gilbert's Interests

What they've been talking about across their social media accounts
  • Deep appreciation for high-quality production value and logistical excellence in entertainment and physical spaces. He closely analyzed a Bad Bunny concert performance to praise how the camera crew remained invisible despite complex choreography and lighting, and he similarly highlighted the acoustic design and architecture of SFO Terminal 1 as a standout experience.
  • Focuses heavily on the business mechanics and history of major technology companies, often dissecting their strategic pivots. He pointed out the evolution of Nvidia's gross margins to illustrate how they moved from a standard hardware business to one resembling a luxury brand driven by scarcity, and he frequently references Google's history, such as when they shipped Maps without Europe to prioritize speed over perfection.
  • Champions the conversational storytelling format in media and encourages creators to apply deep-dive research models to other verticals. He actively promotes the idea of cloning the Acquired podcast structure for topics like infrastructure or politics and compares different content models, such as analyzing the trade-offs between daily news shows and meticulously edited historical narratives.
  • Interest in hard tech infrastructure and the physical reality behind digital services. He shared insights on AI factories and data centers, including an investigation into a location in California's Central Valley where Google built fake roads and driveways to train Waymo autonomous vehicles.
  • Connects everyday observations to software engineering concepts and developer logic. He humorously noted that Duplo blocks use zero-indexing, making them terrible for teaching a toddler to count but excellent for explaining arrays to a programmer.

About their Fund

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AI, SaaS, Consumer, Fintech, Proptech
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PSL Ventures is an early-stage venture fund that focuses on technology-driven companies.

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