Where do the best angel returns come from: the earliest unpolished pre-seed checks or later, more validated rounds?

Harry Stebbings · Jan 12, 2026

Series A is the worst place to be investing

Company progression from seed is minimal while price is four to five times the seed price, at 150–200x ARR with little sign of product-market fit

35:40 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital

Harry Stebbings · Jan 19, 2026

Series A is a bad place to be investing

That is the stage where you have to underwrite valuations you may have to grow into

12:19 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

Harry Stebbings · Feb 9, 2026

Series A is the hardest place to be investing right now because you pay 100-200x ARR on roughly $1M of revenue with very little real signal of product-market fit, in an intensely competitive market where price and progress are mismatched

At $1M revenue there is almost no evidence of product-market fit, yet entry prices are extreme and competition is fierce

Scope: framed as a provocation inviting rebuttal, but stated as his own tweeted view

48:46 20VC: Is SaaS Dead in a World of AI | Do Margins Matter Anymore | Is Triple, Triple, Double, Double Dead Today? | Who Wins the Dev Market: Cursor or Claude Code | Why We Are Not in an AI Bubble with Anish Acharya @ a16z

Harry Stebbings · May 18, 2026

Series A is the worst place to be in venture today

There is little product-market fit at $1-10M of revenue yet prices run 100-400x ARR

Scope: stated as his own view while leading Series A rounds

69:37 20VC: Turning Peter Thiel's $100K into $10M Angel Portfolio | The One Man Accelerator at The Four Seasons | Why VCs Can Be Sharks and What Founders Need to Know | Why Stocks and Cash are BS and You Should Invest in Land with Josh Browder

Harry Stebbings · Jul 27, 2026

Series A is the worst place to invest today, which is why capital is flocking to growth and pre-seed

Companies with $1-3M in revenue are pricing at 200x ARR ($200-400M) with little product-market fit

32:22 20VC: Leading Anthropic's First Ever Round | Will Open Source Threaten Anthropic's Business | Do Margins Matter in a World of AI | Why Triple, Triple, Double, Double is Not Good Enough Today | Why Series A is Hard Today with Matt Murphy @ Menlo

Harry Stebbings · Nov 10, 2025

Entering OpenAI at a $30B valuation is only a six-to-eight-x once real dilution is accounted for, which is weak relative to the best early-stage AI cash-on-cash outcomes

Blunt multiple is ~15x, ~12x with modeled dilution, but actual dilution brings it to six to eight x, versus companies like Mercor, LangChain and Sierra

Scope: still a fantastic outcome in absolute terms

36:05 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid

Gokul Rajaram · Mar 16, 2026

From Series B onward price starts destroying returns — you can pick a genuinely good company at that stage and still get crushed

By then there is real revenue and traction so the price reflects it; a friend invested in a security company at $4B with $100M revenue, and the company grew to $500M revenue but is still valued at $4B, so he won't return 1x his capital

Scope: B and later stages; $100M valuation as an approximate threshold

47:41 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram

Josh Browder · May 18, 2026

Day-one, sub-$5M-valuation investments in unpolished first-time founders are the best investments for him, and the adverse selection problem is solved by living with the founders

The best founders he invested in were ones he actually lived with at some point; unpolished founders can genuinely use his advice from reliving his own founder journey

Scope: specific to his own strategy; other investors play different games such as chasing hot companies at $100M valuations

12:07 20VC: Turning Peter Thiel's $100K into $10M Angel Portfolio | The One Man Accelerator at The Four Seasons | Why VCs Can Be Sharks and What Founders Need to Know | Why Stocks and Cash are BS and You Should Invest in Land with Josh Browder

Josh Browder · May 18, 2026

It pays to be early — the returns from investing at the earliest stage justified raising a fund to keep doing it

His earliest angel checks into Thiel Fellows and Stanford peers performed very well

35:31 20VC: Turning Peter Thiel's $100K into $10M Angel Portfolio | The One Man Accelerator at The Four Seasons | Why VCs Can Be Sharks and What Founders Need to Know | Why Stocks and Cash are BS and You Should Invest in Land with Josh Browder

David Tisch · Feb 5, 2024

Seed valuations that seemed egregious in past eras have become normalized, and rising entry prices only compress returns if exit values compress.

A $10–20M seed price was egregious in 2010–2015 and a $20–30M round was off-market in 2015–2020, yet both are acceptable today; if generational companies produce enormous outcomes over time, the entry price is justified.

Scope: exits need time; not judged by today's depressed public SaaS multiples

21:42 20VC: The Biggest Misconceptions & Hardest Truths About Seed Investing Today; Why The Best Founders Don't Need You, Why Uncapped SAFEs Are Good, Why Reserves Are Bad, Why Signalling is BS, Why Price Doesn't Matter with David Tisch & Terrence Rohan

Immad Akhund · May 12, 2025

At today's seed entry prices of $20-25M, unicorn outcomes no longer produce outsized returns — you need $10B+ companies to get a 10x fund.

After dilution, a seed-to-unicorn path can return as little as 8x, and he isn't interested in a two or three x fund.

Scope: notes seed-to-unicorn can also be 30-40x depending on entry

20:42 20VC Exclusive: Mercury Founder Launches First $26M Fund | Why Founders Should Take the Highest Price | Why Serial Entrepreneurs are Better | Why AI Is So Overhyped | The Future of Venture Capital with Immad Akhund

Harry Stebbings · May 19, 2025

A $3M round at a $15M valuation, which was Duolingo's Series A in 2011, would be a pleasant pre-seed or friends-and-family round today.

61:48 20VC: Duolingo Co-Founder on Why $3M is Harder than $100M to Raise | Why You Should Always Take Tier 1 VCs Even at Worse Terms | Why Europe Can't Win Unless the US Screws Up | How AI Impacts the Future of Work and Education with Severin Hacker

Harry Stebbings · Aug 24, 2026

A billion dollars is effectively the new Series A — investors now pay a billion-dollar entry price hoping for the same multiple they used to chase from a million-dollar post

The old model was a $1M post at Series A hoping for a billion-dollar outcome; the multiple structure is the same, just shifted up a scale

Scope: you have to be in the companies that matter

10:59 20VC: Inside Sequoia's Investment Committee: Lessons from Don Valentine, Doug Leone and Alfred Lin | How the SpaceX and Citadel Deals Went Down | What Sequoia Specifically Looks for in Founders with Julien Bek

Harry Stebbings · Mar 7, 2026

Picking winners at early stage isn't worth it compared to just doing an Anthropic SPV, which is much easier

33:26 20VC: Why the SaaS Apocalypse is BS | Why China Will Win the AI War | Why 50% of VCs Should Not Exist and are Tourists | Why Stock-Based Comp is the Hidden Sin of the Valley with Mitchell Green, Lead Edge Capital

Josh Browder · May 18, 2026 · hedged

Series A is the hardest place to invest, and investing later at multi-billion valuations can actually be the better risk-adjusted spot

There is an illusion that lower Series A valuations mean less risk, whereas at a billion-plus the business is de-risked and you can model the cash flows

Scope: 'I think so'; 'sometimes'

69:57 20VC: Turning Peter Thiel's $100K into $10M Angel Portfolio | The One Man Accelerator at The Four Seasons | Why VCs Can Be Sharks and What Founders Need to Know | Why Stocks and Cash are BS and You Should Invest in Land with Josh Browder

Harry Stebbings · Aug 24, 2026

A billion-dollar round in a company with real revenue and enterprise customers is a better risk-adjusted bet than a Series A priced at $300-500M on $3-4M of revenue

At that scale the company is significantly de-risked — there are enterprise customers and real data to underwrite

11:36 20VC: Inside Sequoia's Investment Committee: Lessons from Don Valentine, Doug Leone and Alfred Lin | How the SpaceX and Citadel Deals Went Down | What Sequoia Specifically Looks for in Founders with Julien Bek

Mitchell Green · Mar 7, 2026

Lead Edge was wrong to pass on the best software companies in 2016-2018 because Iconic was paying 10x revenue while they capped out at five to seven times

They knew at the time these were the best companies, but discipline on price meant they lost the deals

Scope: about the 2016-2018 software financing environment

55:54 20VC: Why the SaaS Apocalypse is BS | Why China Will Win the AI War | Why 50% of VCs Should Not Exist and are Tourists | Why Stock-Based Comp is the Hidden Sin of the Valley with Mitchell Green, Lead Edge Capital

Gokul Rajaram · Mar 16, 2026

Incubation bets on founders who are the best in the world at their specific domain offer far better risk/reward, even at a strong entry valuation

Someone who knows the inner workings of an industry better than anyone — like Jackie Reses, who had already built the bank at Square before building Lead Bank — de-risks the bet enough to justify the price

Scope: applies to inception/incubation rounds

51:09 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram

David Frankel · Aug 8, 2026

Investment frameworks have saved Founder Collective overall, but using valuation as shorthand to say no has caused terrible misses, so he has loosened his adherence to them

Klaviyo came to him first and he passed purely because the framework made it easy to say no; some founders are extraordinary enough to override the framework

Scope: still believes frameworks are net-positive; accepts they will keep missing deals

77:33 20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

Max Altman · Nov 21, 2025

He cannot win Series A leads at this point in his career and should stay in his lane as a seed investor, because Founders Fund, Sequoia, Index and Khosla have effectively locked up the Series A

Series A is a knife fight against firms whose pitch (Sequoia sits on the board of the six most valuable private tech companies) he cannot beat; and any Series A he does win is probably adversely selected

Scope: about his own position, not all seed funds; implies the answer is to get in before them or partner with them

25:56 20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster

Carles Reina · Apr 11, 2026

Angel/seed investors should stay within their lane rather than chase later-stage rounds in hot companies

Series A deals aren't his area of expertise and he gets more enjoyment and edge from scrappy, non-obvious, early companies no one else wants to back

Scope: framed as his personal preference as a pre-seed fund investor

70:48 20Sales: ElevenLabs: Why We Set a 20x Sales Quota | How to Structure Sales Compensation Plans | Customer Success: 'Total BS' or Growth Engine? | Building an AI Sales Machine: What Tools & Tactics Must CROs Adopt Today with Carles Reina

Nick Chirls · Sep 6, 2024

Momentum or consensus investing in a crowded category is better done at Series A or B than at early stage.

If you are trying to pick the winner in a very competitive category, you want data on how the teams and companies actually operate.

16:45 20VC: Why VC is a Ponzi Scheme Today | Why Most VCs are Bankers | Why Big VCs Ruin Startups | Why Incentives in VC are Broken | Why American Dynamism is a Tool for VCs to Raise Money with Nick Chirls, Asylum Ventures

Harry Stebbings · Sep 6, 2024 · hedged

Series B/C is the best place to do consensus momentum investing, not Series A, because at Series A the price inflection is very high while company progression is comparatively shallow.

At Series A you pay a 5x step-up for a company with only a million or two in revenue; the B-to-C crunch, before pre-IPO growth, is where the trade is better.

Scope: he revises from A to 'maybe B' to 'B-C'; 'I don't know if you find this'

17:07 20VC: Why VC is a Ponzi Scheme Today | Why Most VCs are Bankers | Why Big VCs Ruin Startups | Why Incentives in VC are Broken | Why American Dynamism is a Tool for VCs to Raise Money with Nick Chirls, Asylum Ventures

David Cahn · Aug 5, 2024

Given today's market landscape, the right venture strategy is a barbell approach — investing in very early companies and in late-stage mature companies simultaneously

The market is simply different today, so adaptive investors like Pat Grady pick spots at both ends — Harvey early and Grow Therapy late, a cash-generating mature company

Scope: describing today's market dynamics

56:00 20VC: Sequoia's David Cahn on AI's $600BN Question | Why the Data Centre is the Most Important Asset | Servers, Steel and Power: The Core Pillars Powering the Future of AI

Matt Murphy · Jul 27, 2026

The right response to today's market is a barbell: go much earlier at seed with fast decision-making, and concentrate later-stage capital on outliers above $10M ARR that have been anointed category winners

In the $1-3M range you may not even know who the competitors are yet, and you pay as if the company is already the winner

Scope: seed checks up to $8M decided on the spot by three partners; neolabs entered early for ownership rather than with $200M checks

32:51 20VC: Leading Anthropic's First Ever Round | Will Open Source Threaten Anthropic's Business | Do Margins Matter in a World of AI | Why Triple, Triple, Double, Double is Not Good Enough Today | Why Series A is Hard Today with Matt Murphy @ Menlo

Mike Mignano · Jul 6, 2026

Price elasticity should be stage-dependent: you can stretch on price later-stage when you truly believe you have a market winner, but at the earliest stages a small fund must keep a hard price ceiling

Otherwise the fund math doesn't work at the early stage; later stage the multiple can be high enough to justify the price

Scope: nuances Fred Wilson's blanket 'never pass on price' rule

46:41 20VC: Why Now is the Time for the Application Layer | Why OpenAI & Anthropic Won't Win the App Layer | Why Startups Should be TokenMaxxing | Why VCs Should Reduce Weighting on Price & Ownership in an Age of AI with Mike Mignano, USV

David Frankel · Aug 8, 2026

A valuation framework — a post-money ceiling above which a deal is simply not your opportunity — is necessary to act quickly in a fast preemptive market

A framework lets you act very quickly rather than agonize; you accept you'll miss some winners in the rearview mirror

Scope: the post-money ceiling itself has risen over time with the environment

30:25 20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

Anish Acharya · Feb 9, 2026

Competitive risk — whether you can win the deal against other VCs — is the right risk for an investor to take, and the Series A being hard is not a defect: winning hard processes is the core job

Deciding which risks to take is what investors are paid for, and winning deals through trust with founders, market knowledge and being first to conviction is the number one thing a firm does

49:20 Competitive deal risk is the right risk to take

Anish Acharya · Feb 9, 2026

Seed is the hardest stage at which to invest because there is no product and no go-to-market yet, so it's easy to make one great seed investment but hard to build a repeatable system for being right often

At true seed there is nothing there yet even when the people are amazing; post-product pre-traction is easier, and post-product post-traction is effectively a Series A

75:13 True seed is hardest because there is nothing yet to evaluate

Sahil Bloom · Feb 25, 2022

A small fund should stay stage-agnostic and take slam-dunk risk-adjusted Series B opportunities rather than restricting itself to pre-seed, accepting a larger check size for those

Passing up clearly attractive risk-adjusted opportunities purely on stage discipline isn't worth it in this environment

8:51 Opportunistic later stage checks when risk adjusted

Lucas Swisher · Feb 23, 2026

Missing an early round in a great company is not fatal — for the truly great companies there is always another round to get into.

It follows from their strategy of not needing to win the A.

57:30 No need to win the a great companies always offer another round

Alex Rampell · Jan 12, 2026

The stage genuinely worth avoiding is the classic 'Series B trap' — a round where the only change from the prior round is increased burn and internal scaffolding, so investors get half the ownership for no additional progress

At that stage the company has already shown customers and product-market fit signs; the new money funds HR, marketing and infrastructure that don't move the company's metrics

36:00 Series b trap round buys scaffolding not progress

Harry Stebbings · Sep 20, 2023

Series A is currently the most attractive stage to invest, because companies at 2-3M ARR carry meaningful derisking yet clear at 30-40M, whereas seed asks 20-30M for no derisking at all

The price inflection between seed and Series A has compressed, so you pay only a small bump for a lot of additional derisking

35:24 Series a is currently the best entry point given compressed seed to a pricing gap

David Frankel · Aug 8, 2026

Accepting an effective $100–300M price a year in advance via an uncapped note doesn't make sense from a venture returns perspective; access is being sold and endowments are buying it.

Paying tomorrow's price today removes the return math; institutions like Stanford, MIT and Harvard just want to be there

10:49 Paying a year forward price removes the return math

David Frankel · Aug 8, 2026 · hedged

The 'go go go overnight or you're bust' norm creates a large population of orphaned companies, and buying seed-extension rounds when bigger funds have abandoned a company is potentially the most opportune moment to invest.

When larger funds move on, capital dries up and pricing becomes favorable, which Bullpen built a business around.

17:34 Abandoned company seed extensions are the mispriced entry

Shardul Shah · Sep 16, 2024

Arguments about Series B as an asset class based on averages are irrelevant, because venture returns come from exceptions rather than mean reversion.

None of us are in the business of mean reversion; Series B investments like Elastic and Confluent produced terrific returns as exceptions.

23:03 Series b return arguments based on averages are irrelevant since venture lives on exceptions

Shardul Shah · Sep 16, 2024

Higher Series B entry prices plus public-market multiple compression do not make Series B a worse asset class, even for the best companies.

Entry and exit are different time horizons so multiples evolve; the best companies earn premium above-average multiples, and category-defining companies become far more significant, so you can afford to pay up.

23:33 Premium entry price and multiple compression dont hurt returns for category defining companies

Harry Stebbings · Jan 13, 2023

His sweet spot is post-product companies at roughly $20–40k in revenue with some customers and data, where the founder is still leading sales

At that point there's some data and a 'seedling of goodness' to judge

38:03 Post product 20 40k revenue founder led sales stage is the sweet spot for early conviction

Julien Bek · Aug 24, 2026

Some billion-dollar rounds are raised before there is any traction at all, so the de-risking argument doesn't always hold; access at those prices comes from being a trusted company-building partner

The market sets what you have to pay, and founders are choosing company-building partners, so trust with the founder is what earns the allocation

11:59 Pre traction mega rounds are not de risked access comes from founder trust

Julien Bek · Aug 24, 2026

There is no single hardest stage to invest in — the goalpost moves by sector, and in hardware and physical AI you must invest earlier and judge progress by time to a working prototype rather than time from zero to $1M ARR

Moving atoms rather than bits means validation takes longer, costs more capital, and requires backing companies through extended experimentation phases

13:14 Best entry stage depends on sector hardware demands earlier checks

Matt Murphy · Jul 27, 2026

There is never a perfect entry point into a market you've decided to build your firm around — you should get in rather than overthink the price

If you rule yourself out on price you simply sit on the sidelines of the market; once you're in a company that takes off there's plenty of opportunity to add capital later

8:04 No perfect entry point get into the core market