How should founders manage the timing and communication of a fundraising process with investors?

Sumeet Gajri · Jan 17, 2020

The real problem is founders who only talk to investors once they are actively fundraising, which disadvantages both sides

With over a thousand US venture funds, a founder who only appears when raising hasn't gotten to know the people they may be in business with for a long time, and hasn't had the back-and-forth needed to refine their narrative before going to market

34:15 20VC: Portfolio Construction, Optimising SPVs, Opportunity Investing "Between Rounds", Being Distribution-Centric Over Product-Centric and Capital Concentration Within Funds With Sumeet Gajri, Chief Strategy Officer @ Carta

David Tisch · Feb 27, 2023

Founders should continuously build relationships with potential customers, partners, acquirers and investors at every step of the journey rather than only engaging when raising

Investing in lines not dots is how the world actually works — the more two sides know each other, the higher the probability a deal gets done if both like each other

Scope: applies when not optimizing purely for speed

37:18 20VC: How Multi-Stage Funds Changed The Game For Seed Rounds, Why Signalling Risk is BS, The Three Most Important Variables for Founders When Raising Rounds & A Debate on Portfolio Construction: Does Ownership Matter with David Tisch

Harry Stebbings · May 12, 2023

Speaking to no investors between rounds is the wrong approach; founders should instead pick three to five deeply respected investors and build relationships with them in between rounds

People invest in lines, not dots — a fundraise is too short a window to build trust and authenticity for a relationship that will be prominent in your life for fifteen years, so raising without prior relationships is a shotgun marriage

32:39 20VC: Why The Future of AI Is Open Not Closed, Why We Are Years Away From AI Being Autonomous, Why AI Founders Do Not Need to Move to the Valley & Why Founders Should Not Meet Investors in Between Rounds with Clem Delangue @ Hugging Face

Imran Khan · Aug 26, 2024

Snap's IPO process was relatively easy because the company had built relationships with public market investors well in advance, who were already on the cap table and had watched the numbers ramp

Fidelity and T. Rowe were already investors so they knew the story and numbers, and even non-users understood the product through their children

56:10 20VC: Why the IPO Market is not Closed | Why Revenue Multiples are BS and Founders Need to Change | Advice From Jack Ma, Jamie Dimon and Evan Spiegel | Lessons from Taking Snap & Alibaba Public with Imran Khan

Mitchell Green · Mar 28, 2025

Founders should build relationships early with the biggest strategics and potential PE buyers, and guide conservatively so they beat the numbers they give those buyers

It's very hard to get bought if strategics don't know who you are; acquisitions come out of built relationships and a track record of beating stated numbers

25:20 20VC: Why Traditional VC is Broken: How VCs Learned Nothing from 2021 | Why LPs are More Important than Founders & Advice to Emerging Managers | Bull Case for Bytedance & Why TikTok's Ban Doesn't Matter with Mitchell Green, Lead Edge Capital

Zach Lloyd · Oct 17, 2025

When raising the next round, he will source it through existing investors or their introductions rather than inbound VC emails

He is optimizing for the relationship, which is hard to establish from a cold sales pitch over email

Scope: still takes occasional calls to gauge the market

53:23 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

Alex Bouaziz · Oct 22, 2025 · hedged

Not raising money since 2021 meant no one outside Deel's shareholders knew its numbers, and spending more time with investors so they understood the growth would probably have been better

They hadn't raised since 2021 and bought up every secondary, so people saw a $1B ARR announcement with no context; there is value in educating investors who may be your investors of tomorrow

Scope: called a 'small mistake'; framed as a learning opportunity

8:51 20VC: Deel CEO Alex Bouaziz on Raising $300M+ at a $17BN Valuation | Deel vs Rippling: WTF is Going On | Management Lessons from Ben Horowitz and Nik Storonsky | Deel's M&A Playbook: Lessons from 13 Acquisitions: What Works & What Doesn't

Alex Rampell · Jan 12, 2026

A CEO should run a permanent background process, spending 5-10% of their time casually meeting investors and potential acquirers long before they need either

Investors and acquirers back people they already know and trust — pitching cold when you're running out of money rarely works, whereas years of relationship meant Greylock would invest on the strength of knowing him

Scope: the CEO's number one job is not letting the company run out of money

58:43 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

Kathryn Minshew · Sep 2, 2016

Founders should run a structured fundraising process, including scheduling first meetings within a tight window so that all investors move more or less in sync

You have to be flexible, but too much flexibility means the process never comes together

Scope: some flexibility still required

18:14 20VC: How To Win The Strategic Process Of Fundraising and Optimising Co-Founder Relationships and Break Ups with Kathryn Minshew, Founder & CEO @ The Muse

Tom Blomfield · May 13, 2024

Founders should not start fundraising earlier than two weeks before Demo Day because running a competitive process yields better terms

Fundraising early leads either to VCs writing you off for lack of progress or to a preemptive offer at a worse valuation than the Demo Day auction would produce, and without competing offers a nervous founder cannot turn it down

Scope: YC strongly encourages rather than forbids

29:56 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

Dan Siroker · May 15, 2024

Founders should calendar the raise in advance — time-boxing all first meetings into one week and running processes in parallel — rather than taking investor meetings as they come

Taking meetings willy-nilly means you can get a term sheet from one investor before you've even started with the investor you actually want; a fixed public calendar runs everything in parallel

42:01 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless

Dan Siroker · May 15, 2024

Founders should batch inbound investor interest into a dedicated back-to-back 'investor week' every one or two quarters to hone the pitch without disrupting product and customer work

Batching keeps you out of distraction during other modes, and 30 back-to-back meetings where you tweak the deck each time produce a honed pitch like a stand-up comedian's set

44:45 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless

Shervin Pishevar · Jan 13, 2025

Engineering visible competition among investors — lining them up so they saw each other and imposing a hard term-sheet deadline — is what drove Uber's Series D from a ~$10-11B ask to a $17B valuation.

There was so much competition for the deal, which gave Emil leverage to negotiate up.

27:22 20VC: Shervin Pishevar on The Epic Uber War and What Really Happened in the Firing of Travis Kalanick | Raising $15BN to Win China | Why The Traditional Venture Capital Model is Dead | The Future of Quantum and How We Will Cure All Diseases in 10 Years

Max Junestrand · Aug 15, 2025

Founders should bundle VC conversations into a concentrated window rather than taking them early and spread out

Having those conversations too early creates too much context switching; bundling lets you get in the zone

29:52 20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand

Max Junestrand · Aug 15, 2025

Fundraising should be compressed into as little time as possible so founders can spend maximum time building, but a war chest is genuinely needed to compete

Time spent fundraising is time not spent on the business, yet competitive dynamics in the current market require capital

Scope: current competitive environment

62:02 20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand

Max Altman · Nov 21, 2025

Founders should run the Series A as a synchronized race — prep with the seed investor, maybe give one lead a week's head start, then open the gates to all firms at once via GP-level introductions

You want all eight horses chasing you at the same time; a random sloppy sequential process is the biggest way founders screw up their raise

49:26 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

Clem Delangue · May 12, 2023

Founders should not talk to external investors in between rounds

It's a waste of time and a defocus; building the company is hard enough that it demands 100% focus

Scope: he does run a fast, concentrated fundraising window and stops once he has enough term sheets

31:05 20VC: Why The Future of AI Is Open Not Closed, Why We Are Years Away From AI Being Autonomous, Why AI Founders Do Not Need to Move to the Valley & Why Founders Should Not Meet Investors in Between Rounds with Clem Delangue @ Hugging Face

Clem Delangue · May 12, 2023

Investing time in investor relationships between rounds is often wasted because founders can't tell in advance which investors are serious or will fit the company's future stage

Outside a fundraise every investor wants to talk to you, and in a fast-moving startup the right investors change — Hugging Face's seed investors for a consumer Tamagotchi AI product were very different from its Series B investors for a B2B AI platform

Scope: especially in fast-pivoting companies

33:18 20VC: Why The Future of AI Is Open Not Closed, Why We Are Years Away From AI Being Autonomous, Why AI Founders Do Not Need to Move to the Valley & Why Founders Should Not Meet Investors in Between Rounds with Clem Delangue @ Hugging Face

Fabien Pinckaers · Feb 12, 2025

Taking investor meetings outside of an actual transaction is a waste of a founder's time

He had better things to do, like developing the company; he only meets investors when there is an operation, roughly once every three years

Scope: concedes building relationships beforehand can be helpful

51:48 20VC: The $5BN Company Built from the Belgian Countryside | The Story of Odoo: The Company with No Plans to Sell, IPO & Their Billionaire Founder Who Does Not Care About Money with Fabien Pinckaers, Founder & CEO @ Odoo

Harry Stebbings · Oct 22, 2025

Founders today run a more transactional fundraising process than ever, largely because prior-round investors advise them not to take investor meetings or build relationships until they are actively fundraising

Founders arrive with compressed deadlines and rounds that are already essentially done, forcing new investors to decide without prior relationship

Scope: describes current venture market on the ground

25:17 20VC: Deel CEO Alex Bouaziz on Raising $300M+ at a $17BN Valuation | Deel vs Rippling: WTF is Going On | Management Lessons from Ben Horowitz and Nik Storonsky | Deel's M&A Playbook: Lessons from 13 Acquisitions: What Works & What Doesn't

Jason James · Aug 29, 2025

In fundraising, investor meetings and interest mean nothing until the first term sheet arrives, so founders should time-box the process and drive hard toward that first term sheet

Founders are looking for a yes while investors are incentivized to preserve optionality as long as possible; everything before a term sheet is theatrical, and once one is in, everything turns a corner

49:03 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi

Harry Stebbings · Aug 29, 2025

It is genuinely in an investor's interest to preserve optionality for as long as possible

51:21 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi

Harry Stebbings · Jun 27, 2026

A VC wanting to meet does not mean they want to do your round, and founders should not let those meetings distract them

Meeting companies is simply a VC's job

21:52 20VC: How We Got Fred Wilson, Benchmark and Index to Invest $94M | Why Robinhood's Strategy is Wrong | Why 1-1s are BS and What Every Founder Gets Wrong About Equity | Why Taste Beats AI But How AI Kills Org Charts with Paul Erlanger, CEO @ fomo

Jason Lemkin · Jan 13, 2023

Founders should not wait for markets to thaw; conditions are not going back to 2021 levels

Scope: addressed to founders considering delaying a raise

0:00 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

Matt Pohlson · Jun 6, 2025

In the first weeks of the March 2020 crash, waiting even a few days to re-pitch a wavering investor was the wrong move because incoming information would only get worse and investors would not become more bullish

Each new piece of news that week was going to be negative and the situation was not going to improve, so sentiment could only deteriorate

Scope: about the specific March 2020 crash window; they had just enough cash to survive the delay

50:09 20VC: The Science of Storytelling: Three Steps to Master the Perfect Story | From Near Death Experience to Unicorn Startup: The Untold Story of Omaze with Matt Pohlson

Miles Grimshaw · Sep 18, 2023

Founders should not wait for the perfect pitch to approach Benchmark, because Benchmark invests only at early stage and will not re-judge a founder later based on what they said in an earlier meeting

Firms with growth funds make founders pitch multiple times and carry judgments forward; an early-only firm doesn't, so founders should take advantage

17:16 Early only investors dont rejudge so founders should approach early without a polished pitch

Jason James · Aug 29, 2025

Relationship-building with investors should happen between rounds, not during them; once a process starts it should be run tightly, with flexibility only after someone has verbally committed to going deep

You're bringing on both capital and a partner so relationships matter, but inside a process founders get strung along because it's in investors' interest to keep you in the mix

50:26 Cultivate relationships between rounds run tight during flex only after verbal commit

Harry Stebbings · May 12, 2023

An intense three-day relationship formed during a fundraise is manufactured and gives founders no pure read on the investor

During a fundraise the relationship is one of hierarchy and imbalance where each side is selling the other, unlike a no-stakes conversation where you simply get to know each other; a good investor relationship is an equal balance like a marriage

35:17 Fundraise compressed relationships are manufactured and dont reveal true investor character

Clem Delangue · May 12, 2023 · hedged

The dynamic during a fundraise is closer to the real founder-investor relationship than a casual conversation with no fundraising stakes

36:17 Fundraise dynamics reveal real founder investor relationship more than casual conversation

Wesley Chan · Aug 22, 2022

Founders who don't need capital should not publicly fundraise in this market and should instead wait for the market to reset or raise quietly from investors who already know them

VCs don't want to price a falling knife and are doing fewer deals; the market is flooded with founders who have four months or less of runway, so anyone raising publicly gets lumped in with desperation

27:29 Avoid public fundraising in a down market raise quietly from investors who already know you

Dan Siroker · May 15, 2024 · hedged

Founders should avoid answering 'are you raising money?' with a flat yes or no, and instead say something like 'no, but if we get a term sheet we can't refuse we'll take it'

A yes starts a perceived clock in investors' minds, so if you haven't closed in three to six months they assume other investors know something they don't

39:54 Hedge when asked if youre raising to avoid starting a perceived clock

Fabien Pinckaers · Feb 12, 2025

Timing is the most important factor in any fundraise, and their second round was raised at the wrong time and a bad valuation

They needed the money, so they raised €7m at €23m pre-money on roughly €20m of revenue — not a good valuation

19:01 Timing is the most important factor in any fundraise raising out of need produces bad valuations

Trae Stephens · Apr 3, 2024

A founder running a clearly communicated, time-boxed fundraising process is responsible behavior that investors should respect

Communicating expectations and aligning people is important, and if a founder really wants Founders Fund involved they will let the firm walk through the process alongside them

23:10 Clear time boxed fundraising process is responsible behavior investors should respect

Kathryn Minshew · Sep 2, 2016

Founders should never be untruthful about the fundraising process, but should let VCs know roughly where the process stands and the expected timing of term sheets and decisions

Dishonesty always gets found out and comes back to bite you; but without timing signals investors say they'd have done the deal yet couldn't get alignment in time

20:48 Honest timing updates without manufactured pressure

Winston Weinberg · Jan 19, 2026

Founders should start a fundraise six months early by letting one or two target investors in for a small check with information rights, then hitting stated milestones — which makes the actual raise take hours instead of a full process

Repeatedly telling investors what will happen and then delivering builds the trust VCs care about most, so no materials or competitive process is needed

13:49 Seed target investors early with a small check and information rights then deliver milestones

Mati Staniszewski · Sep 8, 2025

Between rounds, the right way to engage investors you don't yet have on the cap table is with one or two concrete asks — an introduction, a hiring problem — rather than fundraising signals.

Investors are genuinely keen to help when the person is right and the problem is clear and doesn't overuse their time, and helping a growing company is good for them too.

26:08 Engage with concrete asks not fundraising signals between rounds

Harry Stebbings · Jun 20, 2026

Founders should raise when they are feeling genuinely confident, because confidence emanates in pitches

60:49 Raise when you genuinely feel confident