Adam Besvinick of Looking Glass Capital: Why Raising Too Much, Too Early Is a Mistake

Adam Besvinick has backed companies like Transfix, BigID, One Concern, and Carrot. In this episode of Care Shift, he breaks down why raising too much, too early can kill a startup, and what a healthy pre-seed round actually looks like.

Adam is the founder and managing partner of Looking Glass Capital, a solo GP pre-seed fund built around one idea: be the first yes. Looking Glass invests across health, climate, and economic drivers. Before launching the firm in 2019, Adam invested from pre-seed through Series C at Deep Fork Capital and Anchorage Capital Group.

We get into: - Why founders with deep industry networks have one of the last real edges in the AI era - The risk of building a business around selling healthcare data to frontier labs - Whether Epic can replicate what healthcare startups are building - How Adam raised Fund I as a solo GP, right before COVID - How ChatGPT split his portfolio in two - Why a two-person company reaching ~$2.5M ARR is proof that constraints win - The most common fundraising mistake first-time founders make

Timestamps 00:00 Intro 00:58 Why be the first check 02:25 Building conviction when others pass 04:30 Picking winners in crowded markets 07:01 The moats that still matter in 2026 09:59 Selling healthcare data to AI labs 13:48 Can Epic replicate your startup? 17:37 Leaving Anchorage to start Looking Glass 21:28 Lessons from raising Fund I 24:08 Earning LP trust as a solo GP 30:12 Why health, climate, and economic drivers 33:56 What Adam looks for in healthcare founders 36:39 How ChatGPT changed his portfolio 41:01 Oversized rounds and bloated financial models 43:36 How multi-stage firms reshaped seed 46:22 The biggest fundraising mistake founders make 49:07 Rapid fire

Connect with Adam Looking Glass Capital: https://lookingglass.vc LinkedIn: https://www.linkedin.com/in/besvinick

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