Should angel investors write uniform check sizes or vary them by conviction?

Jude Gomila · Feb 11, 2020

Angels should keep check sizes consistent rather than varying them by perceived risk

There is pressure from below because of the opportunity cost of your time creating a minimum viable check, and pressure from above because much larger checks come with a different responsibility bracket you may not want; also your riskiest bets can be your best bets, so under-sizing them is a mistake

Scope: he originally varied sizes like a poker game; concluded from his own experience of under-sizing risky bets

30:33 20VC: Lessons from 150 Angel Investments into the likes of Carta, Gusto, Airtable and Superhuman, Creating Algorithms and Models For Investing At Seed & Why Younger Investors Have An Advantage When It Comes To Finding Deals Early with Jude Gomila, Angel I

Harry Stebbings · Jul 18, 2022

New angels should pick one check size and stick to it rather than varying it, because varying implies you know more about one company than another

You do not actually know more about one company than another, so sizing differently is false confidence

Scope: advice aimed at new angel investors

44:30 20VC: Why Being First Does Not Matter, Why Defensibility on Day 1 Does Not Exist, Three Core Elements To Move into Enterprise Effectively and What Makes Truly Great Product Marketing Today with Des Traynor, Co-Founder @ Intercom

David Lieb · Sep 21, 2022

Angels should keep check size static rather than sizing by perceived probability of success or market size, because doing so would systematically invert the correct allocation

It's very hard to know upfront which companies succeed and your gut often tells you the opposite of what happens — the stupidest-seeming companies backed on founder conviction turn out to be the big wins

49:29 20 Product: The No 1 Metric You Need To Look at When Building Product | Why the Best in Product Have No Domain Experience | Why You Should Not Hire From Incumbents & The Difference Between Good vs Great PMs with David Lieb, Visiting Group Partner @ Y Comb

Harry Stebbings · Jul 26, 2023

Operator angels should write the same check size for every investment; varying check sizes reveals a false belief that you have conviction at the early stage

You don't actually have conviction at the early stage, so sizing differently is self-deception

Scope: size itself doesn't matter — 10k, 25k or 50k

49:53 20Growth: Biggest Growth Lessons from Instacart and Opendoor, Why 70% of Growth Experiments Should Fail and How to Fail Fast, How to Hire a Growth Team; Secrets and Tips & Why Operator Investors WIll be the Best Investors in 10 Years with Sri Batchu @ Ram

Jeff Seibert · Nov 22, 2023

Angels should stay disciplined and write the same check size every time across a broad portfolio rather than sizing up on high-conviction deals

His two biggest failures were the ones he was most convinced by and over-invested in; there are too many variables in the startup journey and angels don't do enough diligence to know everything

42:35 20VC: Why OpenAI Will Become an Infrastructure Play, Why Apple Will Win in an AI World, Why Google is the Most Vulnerable Incumbent, Will LLMs Be Commoditised, Which Startups Are Thin vs Thick Wrappers on Top of LLMs with Jeff Seibert, Founder @ Digits

Harry Stebbings · May 8, 2024

The biggest mistake angels make is varying check size with their conviction level; a constant check size is better

Scope: Harry writes $25k every time

25:50 20VC: GV's Tom Hulme on Why Investing in Foundation Models is like Investing in "Power Stations", The Conventional Wisdom in VC that is BS & Lessons from a 24x Angel Track Record, 255x on Robinhood and Making Billions on Uber

Harry Stebbings · Jul 22, 2024

Angel investors should write the same size check in every deal rather than sizing by conviction

You are not smart enough at pre-seed to differentiate conviction levels reliably

Scope: applies at pre-seed stage

56:13 20VC: How I Lost Airbnb at Seed Because of an Exploding Term Sheet | Investing Lessons from Roelof Botha & Peter Thiel | Why VC is Less Collaborative Than Ever and Great Companies Are Being Destroyed by Too Much Cash with Kevin Hartz @ A*

Harry Stebbings · Apr 11, 2026

Angels should write the same size check every time rather than varying check size by conviction

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