How should investors get reliable signal on a founder at the earliest stages?

Tracy Lawrence · Jul 27, 2020

VCs can make fundraising less damaging to founders' mental health by being vulnerable first and checking in on the human behind the pitch

When Foundry opened by talking as friends and humans before turning the spotlight on her, she was able to be real in the pitch; taking five to ten minutes to ask how a founder is actually doing means everything

Scope: based on her own pitch experience with Foundry

43:13 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Harry Stebbings · May 24, 2021

Getting founders to open up requires creating an environment of safety and giving something of yourself first

18:28 20VC: Why Bundling Does Not Work, How The Best Founders Analyse Unit Economics, Why The Way We Approach Mental Health in Venture and Startups is Wrong with Nigel Morris, Co-Founder & Managing Partner @ QED Investors

Julien Bek · Aug 24, 2026

An investor must be vulnerable and share their own personal story first, otherwise founders won't open up and you get no real signal

Founders arrive expecting to pitch their company, but you need the story of the individual; opening up first unlocks that, and otherwise the job is purely transactional

31:09 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

Gili Raanan · Mar 18, 2024

You truly get to know someone not through the inventory of their accomplishments but by understanding why they chose to do what they did.

Motivation reveals far more about a person than achievements do; this is what Moritz probed in his interview.

7:26 20VC: 19 Company Portfolio: 1 Decacorn, 7 Unicorns, 4 Acquisitions; One of the Best Seed Investors of All Time on How to Pick Generational Defining Founders, Why Nothing but the Founder Matters & Why the Best Investors are Never Happy w/ Gili Raanan

Eiso Kant · Oct 7, 2024

A founder's 'why' is the most important question to ask and is rarely asked; people focus on the business, outcomes and the future instead

In any race or ambitious endeavor it's the people who make it happen, not the dollars in the account — capital is just an input — and the why reveals the most about a person

65:45 20VC: Raising $500M To Compete in the Race for AGI | Will Scaling Laws Continue: Is Access to Compute Everything | Will Nvidia Continue To Dominate | The Biggest Bottlenecks in the Race for AGI with Eiso Kant, CTO @ Poolside

Daniel Khachab · Oct 28, 2024

The question investors should ask founders but don't is 'why you, personally' — and whether they'd commit fifteen to twenty years

Investors ask what, how and why the market is great, but the founder's personal motivation and willingness to commit is what actually matters

64:09 20VC: Why SaaS is Dead | Why AI First Companies Will Win | We are in the Middle of a Cold War for AI Talent | Why Europe is F******* and We Need to Stop Whining with Daniel Khachab, Co-Founder @ Choco

George Zachary · Oct 12, 2020

Coherency between a founder's own background and motivation and what the company does is a core investment signal

TJ Parker's pharmacology background and human-centric motivation matched PillPack exactly — his heart was there and he understood the human problem, unlike someone just wanting to sell drugs cheaply from a catalog

21:05 20VC: CRV's George Zachary on His Relationship To Money and How it has Changed Over Time, Why The Best Founders Have Often Experienced Parental or Home Instability and The Stories Behind Investing in Unicorns; PillPack, Yammer and Udacity

Nico Wittenborn · May 22, 2023 · hedged

What matters in a founder is the fit between that person and the specific company or topic, plus how ambitious and driven they are to push it to the limit.

37:45 20VC: Why Your Fund Model Should Not Rely on $10BN+ Outcomes, Why the Large Funds Got Too Large, The Rise of Solo GP's; The Pros and Cons & Is Consumer Subscription Even a Good Sector to Invest in with Nico Wittenborn @ Adjacent

Pat Grady · Jul 8, 2024

The two things that matter most when assessing founders are founder-market fit and the vector that describes the founder

Scope: his personal assessment framework

0:00 20VC: The Sequoia Investment Process | Investing Lessons from Doug Leone, Roelof Botha & Alfred Lin | Sequoia's Framework for Analysing Founders | The True Benefit of Having Sequoia on a Cap Table & Sequoia's Biggest Threat with Pat Grady

Harry Stebbings · Jan 22, 2024

The best pre-seed or seed investment is backing a founder you know so well over years that their idea or sector doesn't matter

Having seen them execute across different situations and environments gives enough conviction to write a 'blank check'

Scope: pre-seed and seed stage

9:19 20VC: Why Small Markets are Better Than Big Markets, The Biggest Delusion of Early Stage VC, Why AI Investing is like a Horserace and Why The Most Ambitious Companies Growing the Fastest are not the Best Investments with Adam Fisher, Partner @ Bessemer

Harry Stebbings · Oct 17, 2025

Passing on Granola was a mistake that stemmed from not having a prior relationship with the founder

Had he known Chris for a while it would have been the easiest check to write; meeting him cold with a vague 'notes plus AI' pitch made it look like just another note-taking company

62:19 20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp

Max Altman · Nov 21, 2025

The core lesson of early-stage investing is to give money to the best people you already know in your network

Rippling was the best deal of the fund and came from exactly that approach

16:51 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

Shreyas Doshi · Aug 3, 2022

The right litmus test for investing or advising is whether the founder is among the most capable people you have ever encountered and whether they can create and hire a top-notch team

It is a simple test, though it requires conversation and asking good questions

Scope: also used as his bar for advising, to keep the number of companies manageable

35:32 20 Product: Shreyas Doshi on The Three Different Types of Product Leaders and How To Hire Them, The 6 Different Product Metrics You Need To Know and What Good is For Each of Them & Table Stakes Features vs Wow Features; What To Prioritise

Joelle Pineau · Nov 3, 2025

When investing very early with little tangible information, a founder's track record matters for two distinct reasons — what they learned about the core technical recipe, and their demonstrated ability to assemble world-class model-building teams

Team assembly at that level has a lot of subtlety to it and is an achievement in its own right, separate from technical know-how

48:11 20VC: Cohere's Chief AI Officer on Why Scaling Laws Will Continue | Whether You Can Buy Success in AI with Talent Acquisitions | The Future of Synthetic Data & What It Means for Models | Why AI Coding is Akin to Image Generation in 2015 with Joelle Pineau

Harry Stebbings · Jan 19, 2026

When a founder continuously hits plan, you should give them more money, because people who do what they said they would do generally keep doing it

Track record of hitting plan is predictive of future execution

15:31 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

When a founder continuously hits target, you should bet on them continuing to hit target

Hitting target is hard, so a track record of doing it is itself the signal — no need to overthink it

40:05 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

Jack Zhang · May 27, 2025

Founders won't volunteer their personal backstory unless an investor asks for it

34:57 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Harry Stebbings · May 27, 2025

The onus is entirely on the question asker — there is no such thing as a bad interviewee, only a bad interviewer, and the same is true for VCs meeting founders

Nobody ever gives him a bad interview; when it goes badly it's because he failed to ask the right questions

35:01 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Terrence Rohan · Feb 5, 2024 · hedged

The one thing an investor can actually sort for is picking genuinely special people, rather than predicting what they'll build

Whether they build something amazing is unknowable, but specialness of the person is at least assessable

Scope: 'at least in myself'; acknowledges it's a belief about the person

61:22 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

Jack Zhang · May 27, 2025

Pre-product-market-fit investing is essentially a judgement on personality and personal history, which is not something he can assess — hence he is not a great early-stage investor

Before PMF there is no data to base a decision on; he couldn't even build confidence to invest in himself

Scope: about his own capability

81:09 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Eric Vishria · Sep 25, 2024

When evaluating a founder on distribution, what matters is depth of thinking and continuous updating of mental models, not having the right answer

conditions change and new information arrives, so a fixed 'this is how it will work' plan can itself be a bad sign

7:16 20VC: Benchmark's Eric Vishria on Where is the Value in AI: Chips, Models or Apps | Why Nvidia Will Not Be The Only Game in Town | The Commoditisation of Foundation Models | Which AI Apps Have Sustaining Value vs Hype and Short Term Revenue

Mamoon Hamid · Oct 21, 2024

Aaron Levie was an instant-invest founder because in 2007 he had thought harder about the cloud storage problem than anyone else, despite being visibly nervous and unpolished

Depth of thinking about the problem, at a time when cloud storage was not yet a thing, signalled founder quality

52:20 20VC: Kleiner Perkins' Mamoon Hamid on Investing Lessons from Leading Rounds in Figma, Slack and Rippling | Lessons Building a Generational Defining Firm with Kleiner Perkins | AI: Where Value Accrues, Startups vs Incumbents & Scaling Laws

Cem Sertoglu · Nov 20, 2024

A founder who does not fit the polished enterprise-software mold can still be the right go-to-market leader; earnestness, technical depth and iteration focus matter more than fluent storytelling

Daniel's English wasn't fluent and he was no narrative storyteller, but watching how he engaged senior potential co-founders convinced them he could handle all leadership responsibilities

Scope: based on 6–9 months of observation before investing

35:54 20VC: Turning $16.5M into $2.1BN; Lessons from the Greatest Venture Investment in European History: UiPath | Why VC is Not Being Commoditised | Why Price Does Not Matter | Lessons on Loss Ratio, Selling and Signalling with Cem Sertoglu

Harry Stebbings · Jan 6, 2025

Very few founders can articulate their insight well, so an insight-based screen risks missing founders who actually have one

He asks every founder about their insight development, but inability to articulate it doesn't mean the insight is absent

37:34 20VC: How To Do a 10x Seed Fund in 2025 | Three Frameworks to Evaluate Startups an Founders | Lessons from Losing Billions Missing Airbnb and Pinterest & Investing Lessons from Charlie Munger with Mike Maples @ Floodgate

Jason Lemkin · Jan 13, 2023

Investors must talk to enough people beyond the founder to screen out bullshit artists, who thrived under the reduced scrutiny of the boom

He once nearly did a deal on a charismatic founder and only discovered on site that the VP Sales was quitting and the head of marketing was the former office manager

Scope: doesn't require meeting the whole management team

29:18 20VC: WTF is Going On in VC? Are VCs Still Investing? How Has What VCs Want in Investments Changed? Are LPs Investing in New Funds? Why VCs That Invest in Public Markets Are Losers? Dec 2023; Will It Be Better Or Worse with Jason Lemkin

Sri Batchu · Jul 26, 2023

Some founders are too slick by half, so personal backchannel diligence is needed to test how real they are

Sales polish can mask substance, and personal diligence is how you find out

48:54 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

Pat Grady · Jul 8, 2024

The second thing to assess is the vector describing the founder — magnitude (exceptional ability on some dimension that matters, which need not be a single identifiable spike; a consistent track record can count) and direction (motivation for doing it).

Building a startup and being a CEO are brutally hard, so without serious motivation a founder won't stick with it long enough to build something that matters.

20:26 20VC: The Sequoia Investment Process | Investing Lessons from Doug Leone, Roelof Botha & Alfred Lin | Sequoia's Framework for Analysing Founders | The True Benefit of Having Sequoia on a Cap Table & Sequoia's Biggest Threat with Pat Grady

Julien Bek · Aug 24, 2026

People can be assessed as vectors — direction (why they're doing this, where they're going) times magnitude (ambition and willingness to endure pain)

Understanding direction and magnitude helps predict where a founder goes next on their trajectory

43:39 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

Pat Grady · Jul 8, 2024

Passing on Segment and Revolut were terrible decisions, and the lesson is that sometimes it really is that simple — the very best founders can articulate everything completely and compellingly in five or ten minutes, and an investor shouldn't let that simplicity undercut conviction.

Both founders answered every question he would have asked within ten minutes, leaving him nothing to probe; because it felt too simple he lacked conviction and passed.

22:54 20VC: The Sequoia Investment Process | Investing Lessons from Doug Leone, Roelof Botha & Alfred Lin | Sequoia's Framework for Analysing Founders | The True Benefit of Having Sequoia on a Cap Table & Sequoia's Biggest Threat with Pat Grady

Julien Bek · Aug 24, 2026

In founder assessment you should look for clarity rather than perfection

Founders who are direct about their worst references give you a lot of texture

41:21 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

Reid Hoffman · Dec 7, 2020

Hoffman initially passed on Airbnb because it was mis-pitched to him as couch surfing, a bad business with tiny average selling price and all the risks of room rental; he now refuses to let an untrusted third party be the voice of an entrepreneur's vision

What makes travel magical for a large swath of people is connecting with local culture and experiences, not just seeing landmarks — which is why hotels have concierge desks — and Airbnb could deliver that natively

Scope: conditional on navigating early safety incidents, property damage, political and hotel-industry opposition, and consumer discomfort with staying in strangers' homes

21:20 20VC: Reid Hoffman on Investing in Airbnb and Passing on Stripe, The Different Styles of Truly Great Leaders, How To Think Through Ownership and Price in Venture & How To Ensure Venture Partnerships Always Have Trust and a Learning Mindset

Emil Michael · Oct 24, 2022

The best investing rule is that connection with the founder comes first — never write a check without meeting the founder and looking them in the eye

He needs to see whether the founder has 'that thing', which requires direct contact even if only twenty minutes on Zoom

54:33 20VC: Uber's Journey to Becoming the Most Valuable Private Tech Company in History, Raising $3BN From Saudi in Just 60 Days, Uber's $30BN Mistake in Food Delivery, Why Recent Uber M&A Will be the Worst in Tech & Mastering Negotiations and Deal-Making with

Tom Blomfield · May 13, 2024

The signal that makes him fund a team in an interview is that they teach him something new about their industry — obsessive domain expertise he didn't have

Founders who are so expert and obsessive that they can show him something new in ten minutes have thought really hard about the problem

21:37 20VC: Behind the Scenes at Y Combinator: The Interview Process | What the Best & Worst Do in the Program | Do the Best All Raise Pre-Demo Day & YC's Fundraising Advice to Startups | Why the Value is in Application Layer AI with Tom Blomfield

Harry Stebbings · Mar 10, 2025

Asking founders 'what do you believe that the world around you doesn't agree with' is an effective way to surface whether they have a unique insight

It gets at the same thing as Maples' unique-insight framework

43:52 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital

Harry Stebbings · May 9, 2026

Investors can't reliably distinguish a 7/10 founder from a 10/10, so anyone who clears a 7/10 bar should get a check

Ten years of investing shows he can tell 1 from 7 but not 7 from 10; if he'd invested in every founder he met he'd be 17x more successful, and he passed on seed rounds in Flexport and Vanta despite seeing the product working

44:05 20VC: What I Learned from 100 of the Best CEOs in the World | What I Learned from Staying with Mr Beast for 3 Weeks | How We Will Spend More on Tokens than Salaries with Cliff Weitzman, Speechify

Ryan Petersen · Jun 20, 2026

Within a YC batch it is not obvious which founders will be great, but it is obvious which are terrible — and just eliminating the bottom half produces good returns

As a peer rather than an investor he could talk to founders and get the real story about who was not a good person or operator

Scope: based on angel investing inside his own YC batch

48:28 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

Harry Stebbings · Jan 26, 2026

Venture investing is an easier job than investors get credit for, because truly obsessed founders are obvious when you meet them

When you sit down with founders who are unhinged and psychopathically obsessed — like Alan Chang refusing to angel invest because it would mean selling Revolut or Fuse shares — it is immediately clear

57:44 20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora

Julien Bek · Aug 24, 2026

Nikolai of Revolut was the most obvious founder call of his career, purely on how visibly intense he was

It was immediately obvious in the pitch how intense he was

70:08 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

David Tisch · Feb 5, 2024

A deck or product is valuable because it forces the founder to articulate the idea in their head and reveals their thinking

It takes the idea and puts a picture around it, letting the investor understand how the founder thinks

82:10 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

Tom Hulme · May 8, 2024

The point of grilling founders on their product is not the product itself but to reveal how they think, and skipping that time — usually because the deal is hot — is a costly mistake

Empirically the product often changes a lot, so what matters is how they measure success and whether they've researched the market; the product is just a lens onto their thinking

Scope: about angel-stage decision making

20:13 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

Tom Hulme · May 8, 2024

At seed, founders should be able to articulate their unfair advantage, a credible 'why now', and what keeps them up at night — and a striking number have no paranoia at all, which is a warning sign

Only the paranoid survive; recency bias means something may have failed before, so the founder needs a real point of view on why this difficult thing can happen now

Scope: specifically seed-stage assessment

21:19 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 · May 8, 2024

The best founders can immediately list ten things that terrify them, and asking for help on them is a brilliant signal

Scope: described as a pattern he sees

22:09 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

Adam Fisher · Jan 22, 2024 · hedged

When things go wrong it is usually the doubt he already had about the entrepreneur that materialises, and those are the most difficult losses because you kind of saw it coming

Early signals like lack of transparency or poor communication that he couldn't tell apart from a bad first impression often presaged what happened over the following years

Scope: he says it's a tough question and he's not always 100% sure about the entrepreneur

29:05 20VC: Why Small Markets are Better Than Big Markets, The Biggest Delusion of Early Stage VC, Why AI Investing is like a Horserace and Why The Most Ambitious Companies Growing the Fastest are not the Best Investments with Adam Fisher, Partner @ Bessemer

Harry Stebbings · Jan 22, 2024

He never writes a check when a founder makes him feel uncomfortable or 'icky'

That nagging off feeling at the point of investing is the concern that later materialises

29:52 20VC: Why Small Markets are Better Than Big Markets, The Biggest Delusion of Early Stage VC, Why AI Investing is like a Horserace and Why The Most Ambitious Companies Growing the Fastest are not the Best Investments with Adam Fisher, Partner @ Bessemer

Katherine Boyle · Oct 1, 2020

'How' questions are more revelatory of a founder's depth than the standard problem/solution/metrics pitch questions, and a genuinely compelling founder thesis usually contradicts the dominant narrative while being backed by unusually rich data

Founders with a contrarian thesis have had to defend it repeatedly, so they accumulate data and examples; and pressing on how they will execute exposes how deep they have gone into their own thesis

16:05 How questions and contrarian data rich theses reveal founder narrative fit better than standard pitch questions

Gili Raanan · Mar 28, 2026

Investors should back the founders they personally have the most chemistry with, rather than trying to match founders to a single archetype

Founders come in all shapes and forms, so there is no one template of a great founder; chemistry is the more reliable filter

45:25 Personal chemistry over any founder archetype

Jason Lemkin · May 27, 2024

Customer references should only be requested once you're ~90% sure you want to invest, and only to confirm what you already believe — never to turn a marginal deal into a yes

As a founder he felt uncomfortable burning customer goodwill for investors who then don't invest, so he treats the calls as a real favor; and if a company is at $1M growing 10% a month with low churn, you can already assume customers are mostly happy

35:34 Customer references are for confirmation not persuasion so request them late

Ophelia Brown · Mar 17, 2023

An investor can reach a go / no-go decision on a founder within the first meeting, provided they actively test themselves against being seduced by a good salesperson

She constantly interrogates her own early enthusiasm during the meeting - asking whether the love is real or she is just caught up in the pitch

6:05 Self testing against salesperson seduction enables fast first meeting conviction

Gili Raanan · Mar 18, 2024

When founders claim every customer they spoke to loves the product, they have misunderstood or failed to listen to the customer.

Universal customer enthusiasm is simply impossible, so the claim reflects a listening failure.

52:27 Founders claiming universal customer love signal poor listening

Phin Barnes · Oct 2, 2023

Asking a founder 'what's the best thing that happened at your company this week?' is highly diagnostic, because the answer reveals what excites them, how they approach problems, and whether they take or give credit and frame events as victimhood or as a puzzle

The framing of the answer exposes priorities, motivations and operating style, which predict how they'll lead

9:57 Asking best thing that happened this week reveals founder priorities and framing

Stephane Kurgan · Jul 28, 2023

The key things to assess in early-stage founders are appetite to listen, what drives them, self-awareness and vulnerability — qualities that don't require age or experience

Great leadership is fundamentally self-awareness and vulnerability, and those are innate rather than acquired with age

12:42 Appetite to listen drivers self awareness and vulnerability are the key early stage founder signals independent of age

Wesley Chan · Aug 22, 2022

You should never ask founders directly about their product planning or roadmap; instead ask the same question ten different ways and test whether the answers stay consistent

Direct questions are gameable — founders tell you what you want to hear and a friend at Google can help produce a legitimate-looking roadmap that says nothing about their ability to see what the company must become

34:34 Ask the same question many different ways to test consistency of answers

Harry Stebbings · Jul 8, 2024

The best founders should make you feel a little uncomfortable rather than at ease.

23:57 Great founders make investors uncomfortable not at ease

Steve Jurvetson · Aug 3, 2020

Asking a founder 'what does the company look like in twenty years?' at the end of a first pitch meeting reliably separates true company builders from arbitrage-seeking opportunists

Opportunists laugh at or have no answer to the question because they'll have flipped the company and moved to their third startup; real founders give an answer richer than anything in their pitch, as if relieved to finally discuss what matters

11:03 Twenty year vision question separates builders from arbitrage seeking opportunists

Nikhil Basu Trivedi · Sep 6, 2023

Asking a founder to role-play the first board meeting and name the top discussion topic is a strong diagnostic of whether they are clear-eyed and transparent about their business

You learn whether the founder's stated priority matches what you think matters most, and whether they can be transparent and vulnerable about it

24:55 Role playing the first board meeting reveals founder transparency

Harry Stebbings · Sep 6, 2023

The best founders readily enumerate their many challenges, whereas weaker founders shield themselves from the question

He observes this pattern consistently across founder meetings

25:33 Willingness to enumerate challenges signals founder quality

Nikhil Basu Trivedi · Sep 6, 2023

Being confident about what is working while remaining clear-eyed and self-aware about what isn't yet working is a characteristic of many great founders

25:50 Confidence about strengths paired with clarity about weaknesses signals great founders

Nikhil Basu Trivedi · Sep 6, 2023 · hedged

Your own behavior in the hours after a first meeting is the reliable signal: if you're still thinking about it, researching and calling people that evening, pay attention; if you've done nothing two days later, it's probably not a fit

He went back and studied his own cases and rarely found a company he ignored for days that turned out to be massive

27:20 Your own post meeting engagement and research reveals genuine founder conviction

Avichal Garg · Apr 11, 2022

An exceptional founding team is identifiable within ten to fifteen minutes by intellectual throughput — they burn through an hour of normal questions with deeply insightful answers

in the Magic Eden meeting the team exhausted his usual hour of questions in ten minutes with insightful answers, and he was convinced to invest before the meeting was a quarter over

53:24 Intellectual throughput burning through an hour of questions in minutes signals an exceptional team

Ilir Sela · Aug 4, 2023

The most revealing question to ask a founder is 'if you wanted to compete with your own company, where would you start' — and almost nobody asks it

It surfaces the company's true weakness and blind spot

33:32 Asking founders how theyd compete with themselves surfaces the true weakness

Nigel Morris · May 24, 2021

In early-stage pitch conversations, investors should avoid unanswerable quantitative questions (e.g., projected revenue in six years) and instead ask qualitative questions — about motivation, what has gone well or badly, and who on the team the founder trusts — in a supportive, non-adversarial way

Most venture investments fail and most founders you meet won't succeed; many have had charmed lives and never faced failure, so whether they dust themselves off or fold is what you must discern

16:03 Avoid unanswerable quantitative questions ask qualitative ones about motivation and resilience

Dan Siroker · May 15, 2024

'What will get you excited to be in this business in five years?' is a uniquely predictive question to ask a founder

Fenton asked him in 2013 and exactly five years later he felt trapped, resentful and disengaged; had he really engaged with the question he could have done a better job staying in love with the business

56:34 Asking what will keep you excited in five years predicts founder longevity and fit

Jason Lemkin · Nov 30, 2022

How a founder answers competition questions is a strong predictor of outcome — the investments that failed all had mediocre competitive answers, while the best founders know and respect their competition cold

He can vividly recall that every one of his handful of failed investments answered competitive questions mediocrely

20:33 A founders competitive answer quality predicts investment outcome

Cem Sertoglu · Nov 20, 2024

Reading true founder signal now requires local immersion, because the startup playbook has spread globally and founders everywhere can tell a compelling story regardless of whether anything is behind it

Only immersion lets you reference founders, understand where they came from, which schools and companies shaped them, and judge whether that environment produces great founders

7:06 Local immersion is required to see through a globalized founder playbook

Oren Zeev · Feb 2, 2026

Meeting a founder at an earlier, less confident stage lets you tell real confidence from performed confidence later

Having seen her before she was confident, he knew the confidence was real and not bullshit

57:36 Track the founder from before they were confident

Cyan Banister · Oct 19, 2020

Asking a founder for their personal story rather than the business is the fastest way to judge them; she often makes up her mind about the person in the first ten minutes, before hearing about the product

Everyone chooses how to spend their time, so why this person picked this problem reveals who they are; the stories they tell are usually stories of resilience, and the struggle often points directly at the problem they are solving

11:52 Founders personal story of resilience reveals character faster than business pitch

David Schneider · Sep 11, 2024 · hedged

Sales-trained discovery skills make for better diligence and referencing, because the truth usually only surfaces on the second or third question rather than the first answer

A natural line of questioning lets each answer open the next probe; not being satisfied with the first answer gets you closer to the truth

26:09 Sales trained discovery skill improves diligence and referencing via follow up questions

Jean-Denis Greze · Jul 21, 2023

It is very hard to predict at angel stage who will succeed, because people's capacity to grow into great founders is not predictable

He has repeatedly seen founders he doubted transform into exceptional operators

44:23 Founders capacity to grow into greatness is unpredictable at angel stage

Terrence Rohan · Feb 5, 2024

He bets on the person and the general space rather than the deck, but founders must convey an authentic, original vision

82:25 Bet on the person and space not the deck though vision must be authentic

Doug Leone · Sep 14, 2021

Asking a candidate to describe a close-in-age sibling in three adjectives is a strong test of self-awareness, because they will usually describe themselves as the opposite of the sibling

By the law of diversity, two siblings are less likely to be alike than two strangers, so the description reveals how the candidate positions themselves by comparison

5:33 Sibling adjective comparison question reveals self awareness by contrast

Gokul Rajaram · Mar 16, 2026

Meeting three or four companies in the same space quickly reveals which founder has materially deeper market understanding, so investors should scan the full landscape before committing

People who met Tony at DoorDash alongside other founders fundraising at the same time consistently felt he understood the market more deeply; he missed Vanta because he had already committed elsewhere without scanning the landscape

59:34 Compare several founders in the same space before committing

Harry Stebbings · Mar 16, 2026

When a source has a consistent track record of sending great deals, you should just invest rather than second-guess them

Every time Eli sends something and says it's amazing, it is; other friends' recommendations are consistently bad

61:43 Referrer track record is sufficient signal

Harry Stebbings · Aug 24, 2026

At pre-seed, references should be weighted more heavily than almost any other signal

He passed on Granola's Chris because he wasn't articulate, wasn't a great salesperson and the idea was loose — despite the strongest references he'd ever heard

35:55 Weight references above in meeting impressions

Julien Bek · Aug 24, 2026

You must come into a founder meeting with a plan and be intentional about asking the questions that surface what's special, or you will underestimate the person

He had a casual, unplanned lunch with Anton from Lovable and simply didn't see it

36:26 Come with an intentional question plan

Julien Bek · Aug 24, 2026

Asking a founder who their worst reference would be and why is revealing, because the counter-question after the easy best-reference question changes their demeanor

Founders happily volunteer flattering references; the counter question exposes how they handle it

40:52 Worst reference counter question exposes the person

Julien Bek · Aug 24, 2026

Only exceptional people can reliably identify other exceptional people, so references must be taken from exceptional people, not merely good-enough ones

By the chess ELO analogy: a 2,400-rated player can spot another outlier in ten moves, while a 2,000-rated player cannot tell the difference

42:11 References only count from exceptional people

Harry Stebbings · Aug 24, 2026

Exceptional entrepreneurs rarely give enthusiastic references about anyone, which makes reference-taking from them hard

Torsten at Helsing and Alan at Fuse are exceptional founders but have never told him anyone is amazing — at best 'they were okay'

43:02 Muted references must be interpreted not taken literally

Julien Bek · Aug 24, 2026

There is no single best reader of founders — the right evaluator depends on the founder type and sector

Alfred and Shaun for young technical founders, Doug or Pat for commercial founders, Bogomil for reading people generally, George for fintech because he knows all of them and is calibrated

46:34 Match the evaluator to the founder type and sector

Harry Stebbings · Nov 21, 2025

You can see whether a company will work within the first board meeting and first few investor updates

The way they run the meeting — structure, mindset, approach, aggression — reveals it very quickly

19:07 First board meeting and updates reveal the outcome