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Adam Besnivick: How to Invest in Pre-Seed & Seed Stage Companies; Looking Glass Capital | E1020

Adam Besvinick is the Founder of Looking Glass Capital, a pre-seed-focused firm started in 2020. Before starting Looking Glass, Adam spent about 5 years at Deep Fork Capital and Anchorage Capital Group investing in pre-seed through Series C. Adam’s portfolio across funds includes the likes of BigID, Transfix, NomNom, and Hone Health, to name a few. ------------------------------------------------------ Timestamps: 0:00 How Adam Besvinick founded Looking Glass Capital 6:29 Fund Construction at Looking Glass 13:10 Document Preparation for Fundraising 20:40 How to Find Your LPs 29:05 Lessons Learned from First Fund 40:20 How to Think about Loss Ratio 42:35 Benefits of Thematic Investments 45:38 Biggest Mistakes Founders Make 54:40 Quick-Fire Round 59:41 What Has Changed in Venture Capital? ------------------------------------------------------ In Today’s Episode with Adam Besvinick We Discuss: 1. How Twitter Led to Founding a Venture Firm: How did Adam make his way into the world of venture through Twitter? What are 1-2 of his biggest lessons from working with the legend, Chris Sacca? What does Adam know now that he wishes he had known at the beginning of his time in VC? What do most young VCs misunderstand when it comes to reputation? 2. Raising Fund I: The Process: How many LP meetings did Adam have to close Fund I? What docs and materials did he have for the fundraise? How does he advise other managers on doing docs for fundraises? How do different LP profiles want different things in the managers they work with? How did Adam approach first vs final close? How does he advise others managers on closing? How did Adam instil a sense of urgency in LPs to move and commit to the fund? What are 1-2 of Adam’s biggest pieces of advice to managers raising a first-time fund? 3. Looking Glass: The Very Disciplined Pre-Seed Strategy: How did Adam decide on the fund size? Why is it the optimal fund size? What is the desired ownership for Adam? What level of dilution does he expect across the lifecycle of the company? What is the average check size? What is the average entry price? How does Adam approach reserves and follow-on checks? How does Adam reflect on his own relationship to price? Why does Adam not like the majority of pre-seed micro-fund strategies? 4. The Market: Multi-Stage Firms Destroying Seed Does Adam agree that “multi-stage firms have destroyed seed rounds”? How does Adam advise founders when they have multi-stage offers and seed firm offers? Who will be the winners and losers in the next 10 years of venture? Why is it harder than ever to advise founders on fundraising rounds today? ------------------------------------------------------ Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Adam Besvinick on Twitter: https://twitter.com/besnivick Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ------------------------------------------------------ #AdamBesnivick #LookingGlassCapital #HarryStebbings

Adam BesvinickguestHarry Stebbingshost
May 28, 20231h 7mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Pre-seed discipline, reputation, and thematic focus in modern venture

  1. Adam Besvinick, founder of Looking Glass Capital, explains his highly disciplined, institutional-style approach to pre-seed and seed investing from a relatively small solo GP fund. He emphasizes reputation with founders as an investor’s primary controllable currency and argues for concentrated portfolios with meaningful ownership rather than spray-and-pray strategies. The conversation dives into fund construction, LP fundraising dynamics, thematic focus (healthcare, climate, education, SMB SaaS), and how to lead and structure early rounds without massive checks. They also explore the post-2021 venture reset, multi-stage funds’ impact on seed, and how founders should think about runway, investor selection, and round composition.

IDEAS WORTH REMEMBERING

5 ideas

Reputation with founders is the investor’s most important controllable asset.

Track record is partially out of a VC’s control, but how you behave with entrepreneurs compounds over time into better referrals, deal flow, and outcomes.

Small funds can work with concentrated portfolios if ownership is meaningful.

With sub-$50M funds, Adam argues every investment should be capable of returning the fund, which requires targeting ~4–5% entry ownership and disciplined check sizing rather than dozens of tiny bets.

First-money-in and ‘first yes’ can substitute for huge checks if you add real value.

By setting terms, committing early, and then effectively acting as a placement agent to build the syndicate, a smaller fund can still ‘lead’ rounds and influence cap table construction.

Thematic focus is a sourcing and credibility engine for a solo GP.

Concentrating on sectors like healthcare, climate, education, and SMB tools helps Adam stay top-of-mind with other investors, attract relevant cold inbound, and immediately build trust with founders through portfolio adjacency.

LP fundraising requires clarity on your ideal LP ‘phenotype’ and minimum viable fund size.

First-time managers should understand which LPs will truly grasp their strategy, do an early first close once they’ve hit ~50% of a minimum viable fund size, and then invest as if they’ll never exceed that number.

WORDS WORTH SAVING

5 quotes

Reputation is the number one currency as an investor that you have control over.

— Adam Besvinick

If you’re investing out of a $50 million fund or smaller, a billion-dollar outcome has to return the fund, or this job becomes even harder than it already is.

— Adam Besvinick

To me, the definition of a lead is the one that helps catalyze a raise, sets the terms, and is the first call when things are going terribly or when things are going really well.

— Adam Besvinick

Raise capital from reputable, reliable sources that align with your ethical standards and that are providing clean terms. Beyond that, it almost doesn’t matter who you raise from.

— Adam Besvinick

This is not a home run game, it’s a grand slam game.

— Adam Besvinick

Adam’s path into venture and lessons from Chris SaccaReputation as core investor currency with founders and peersLooking Glass Capital’s fund structure, ownership strategy, and check sizesFundraising from LPs: docs, LP types, first close strategy, and urgencyThematic pre-seed investing vs. generalist approachesRound construction, leading without the biggest check, and signaling riskMarket reset post-2021: deployment pace, seed vs. A/B/C dynamics, and founder advice

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