Gathering Feedback Like an LLM

How do you invest when it’s “too early for data”—but just right for conviction? In this episode, I speak with Vivek Ladsariya, Managing Director at Pioneer Square Labs (PSL), about what it really takes to back founders before traction, before funding rounds, and sometimes even before incorporation. Vivek shares how he partners with founders as a thought partner instead of a coach, why iteration trumps ideas, and how efficiency and automation have rewritten what it means to earn a Series A today. From early-stage pattern recognition to AI-driven productivity and new definitions of founder resilience, this conversation is a masterclass in what “being early” actually means in 2025

Highlights:

• How investing “too early” often creates the strongest long-term alpha
• Why the best investors act as thought partners, not back-seat CEOs
• How ego, relentlessness, and intellectual honesty predict outlier founders
• Why great ideas matter less than constant iteration and customer focus
• How Series A benchmarks have shifted to roughly $7 million ARR—and what it means for founders
• Why AI is the new leverage for coding, sales, and operations efficiency
• How language itself has become code, allowing anyone to automate with LLMs
• How PSL’s studio + fund model accelerates founders from zero to one
• Why small, elite teams outperform larger organizations in the AI era
• How becoming a parent sharpened Vivek’s priorities and patience as an investor

Guest Bio:

Vivek Ladsariya is a Managing Director at Pioneer Square Labs (PSL), where he leads pre-seed and seed investments out of PSL Ventures Fund II ($100 million), focusing on AI, cybersecurity, infrastructure, industrial tech, and DevOps. Before joining PSL, he was a General Partner at SineWave Ventures and an entrepreneur behind ventures such as GameGarage and Moyyer.

His investments include Databricks, Rescale, Osaro, and Evolv Technologies (NASDAQ: EVLV). Vivek holds an MBA from Yale University and a B.E. from the University of Mumbai.

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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Vivek Ladsariya: https://www.linkedin.com/in/vivek-ladsariya-8a828535/

Links Pioneer Square Labs: https://www.linkedin.com/company/pioneer-square-labs/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Preview (0:06) Evolution of programming languages and business automation (1:05) Welcome and guest introduction (1:16) Investing early in startups and the role of a VC (4:17) Creating value in startups and being an effective thought partner (7:11) Handling crises, feedback, and the role of ego in startups (11:27) Ray Dalio's concept of believability and startup ideas (18:22) Customer pain points and the idea maze (21:17) Predicting entrepreneurial perseverance and evaluating founders (24:44) Iterating startup ideas and future Series A expectations (35:16) The impact of AI on programming and business processes (42:56) Preparing skills for a post-AI world (46:14) Pioneer Square Labs and thoughts on seed strapping (50:52) Advice to a younger self and the impact of life changes on investing (57:07) Closing remarks