The best firsthand fundraising stories and advice on the internet, curated for founders. Real seed rounds, real rejections, real term sheets, told by the founders and investors who lived them.
The library, ordered the way a raise actually unfolds. Each step links to the strongest items on that part of the process.
Are you actually ready to raise?
Who should even be on your list?
How do you get the meeting?
What do you show and say?
How do you run the room?
What do the terms really mean?
How do you get to signed and wired?
If you only read eight things before your raise, read these.
Paul Graham's definitive essay on early-stage fundraising, distilled from watching hundreds of YC companies raise. Covers why fundraising feels harder than it is, breadth-first search weighted by expected value, getting to yes/no fast, and the dangers of raising too much or letting fundraising drag on.
Canva co-founder Melanie Perkins recounts pitching for three years and being rejected by more than 100 investors before closing Canva's first round, including how she reworked the pitch around each objection. She details the kitesurfing-with-investors period in Silicon Valley and how rejection shaped the company's strategy.
Suhail Doshi recounts Mixpanel's 2009 raise: $15K from YC, half the batch dying after demo day, 11 firms saying no, two firms wanting to replace him as CEO, and a VC telling him point blank he'd fail, before closing $500K at a $2M pre a week before running out of money. He extracts what actually drove the eventual yes: team and whether the idea is personally interesting to the investor.
Suster's most famous mental model: every founder-investor interaction is a dot, and investors gain conviction from the line those dots draw over time. Argues founders should meet investors months before raising and show progress against stated plans.
Airbnb CEO Brian Chesky talks with Jason Calacanis about the company's early days: living off credit cards, the cereal-box hustle, and the wave of investor rejections at a $1.5M valuation before YC and Sequoia came in. Strong sections on what rejection taught him about conviction.
Cloudflare's CEO shares two of the company's worst fundraising stories: a Sequoia partner who passed because he didn't think a woman (co-founder Michelle Zatlyn) could lead a security infrastructure company, and an unprepared meet-and-greet with Marc Andreessen that turned out to be a full pitch. Posted during the June 2026 viral VC horror-story wave.
Halioua details exactly how she raised $5.1M pre-product for a dog-longevity biotech as a solo, first-time, female founder: building the narrative for a moonshot, sequencing investors, and handling deep-tech skepticism.
Hustle Fund GP Elizabeth Yin takes live pitches from real founders and gives unfiltered feedback in real time, explaining her actual investment thought process as she reacts to each pitch.
Hand-picked reading lists that cut across formats.
Sleeping partners, ambush meetings, and the pitches that went sideways.
Firsthand accounts of real seed rounds, from first no to wire transfer.
Investors explaining, in their own words, what a pass really means.
Founders who published their decks, term sheets and numbers for everyone.
The rounds that did not close, written up by the founders who lived them.
Arguments against the standard fundraising playbook, from people who know it best.
All 234 items, ranked by editorial score. Filter by format, topic, stage or perspective.
Paul Graham's definitive essay on early-stage fundraising, distilled from watching hundreds of YC companies raise. Covers why fundraising feels harder than it is, breadth-first search weighted by expected value, getting to yes/no fast, and the dangers of raising too much or letting fundraising drag on.
A veteran VC and former founder walks through a fictional-but-realistic 'grim fairy tale' in which a founder builds a billion-dollar company and ends up with nothing, term by term: participating preferred, ratchets, guaranteed IPO returns, redemption rights.
Gurley's landmark analysis of the late-stage unicorn financing market: how dirty term sheets, valuation obsession, and the incentives of every player (founders, VCs, LPs, bankers) set up companies for painful recaps. Written at the top of the 2015-16 cycle and vindicated repeatedly since.
Lavingia raised $8M from top VCs at 19, failed to hit venture-scale growth, laid off 75% of his team after a failed Series B, and rebuilt Gumroad as a profitable, deliberately smaller company. A brutally honest account of what happens when you take venture money and land on the 'good but not billion-dollar' outcome.
Canva co-founder Melanie Perkins recounts pitching for three years and being rejected by more than 100 investors before closing Canva's first round, including how she reworked the pitch around each objection. She details the kitesurfing-with-investors period in Silicon Valley and how rejection shaped the company's strategy.
Suhail Doshi recounts Mixpanel's 2009 raise: $15K from YC, half the batch dying after demo day, 11 firms saying no, two firms wanting to replace him as CEO, and a VC telling him point blank he'd fail, before closing $500K at a $2M pre a week before running out of money. He extracts what actually drove the eventual yes: team and whether the idea is personally interesting to the investor.
First Round distills lessons from over 1,000 rounds raised by its portfolio into a tactical playbook for follow-on fundraising: narrative construction, running a tight process, benchmarking traps, and partner-meeting dynamics.
Airbnb CEO Brian Chesky talks with Jason Calacanis about the company's early days: living off credit cards, the cereal-box hustle, and the wave of investor rejections at a $1.5M valuation before YC and Sequoia came in. Strong sections on what rejection taught him about conviction.
Gagan Biyani walks through every mistake three first-time founders made raising Udemy's seed: 200+ rejections and 12 months of wasted fundraising before barely pulling through. Each mistake is framed as a lesson for new founders.
Cloudflare's CEO shares two of the company's worst fundraising stories: a Sequoia partner who passed because he didn't think a woman (co-founder Michelle Zatlyn) could lead a security infrastructure company, and an unprepared meet-and-greet with Marc Andreessen that turned out to be a full pitch. Posted during the June 2026 viral VC horror-story wave.
Suster's most famous mental model: every founder-investor interaction is a dot, and investors gain conviction from the line those dots draw over time. Argues founders should meet investors months before raising and show progress against stated plans.
YC's comprehensive seed fundraising manual: when to raise, how much, SAFEs vs. priced rounds, meeting mechanics, negotiation, and closing documents, written by a YC partner for first-time founders.
Buffer publishes every detail of its $3.5M Series A: the valuation, the actual term sheet, investor list, ARR ($4.6M), and the unusual structure that let founders and early employees take secondary money. A landmark in fundraising transparency.
Collin publishes the actual deck Front used to raise its $10M Series A, slide by slide, with commentary on what worked. Later viewed over 2 million times and followed by her Series B, C, and D decks.
Halioua details exactly how she raised $5.1M pre-product for a dog-longevity biotech as a solo, first-time, female founder: building the narrative for a moonshot, sequencing investors, and handling deep-tech skepticism.
The classic teardown of how VCs quietly lower your effective valuation by putting the option pool in the pre-money. Includes the math and negotiation scripts to fight back.
Graham on the emotional reality of raising: why fundraising is demoralizing by design, why investors herd and stall, and how to keep morale and the company alive through the process. Written mid-financial-crisis.
The CEO of Sonar (millions of downloads, ~$2M raised) explains the company's death: chasing engagement over growth, a failed nine-month attempt to sell rather than cut costs, and how investor incentives shaped the endgame. Read by over a million people.
After his bruising VC experience at Moz, Fishkin raised $1.3M from 35 angels under a novel structure allowing profit-sharing distributions instead of requiring a huge exit, and open-sourced the legal docs so others could copy it.
YC partner Brad Flora's Startup School talk on how startup fundraising actually works: what investors are looking for, how rounds come together, SAFEs, and how to run a tight process. Draws on YC batch data and his own founder experience.
YC partners share real investor horror stories from their founder days and from companies they've advised: exploding term sheets, tranched deals gone wrong, investors behaving badly after wiring, and how founders should protect themselves.
A first-principles walkthrough of how early fundraising actually works, synthesized from Biyani's experience raising roughly $70M from about 1,500 investors across three companies. Covers how to think about investor incentives, sequencing, and running a process.
Hustle Fund GP Elizabeth Yin takes live pitches from real founders and gives unfiltered feedback in real time, explaining her actual investment thought process as she reacts to each pitch.
Prince's follow-up horror story: after Khosla Ventures issued a Series C term sheet, Vinod Khosla allegedly leaned over at dinner, while Prince's co-founders were away from the table, and suggested Prince fire them and take their equity. Cloudflare didn't take the money.
Long-form conversation with Upfront Ventures' Mark Suster on how to pitch VCs, why he dislikes demo days, what separates the best founders, and how Series A decisions really get made inside a firm.
Isenberg describes pitching a $15M Series A at a top-3 VC firm while one of the general partners slept for 30+ minutes and everyone pretended not to notice. The post kicked off the June 2026 viral wave of founders sharing VC horror stories, drawing replies from Mark Pincus, Travis Kalanick, Matthew Prince, and others.
Michael Seibel's SaaStr session on pitching a seed-stage startup: the exact structure of a two-minute pitch, the most common ways founders confuse investors, and live Q&A with founders in the room.
A former founder turned pre-seed VC (20,000+ pitches reviewed) explains the questions investors actually ask, and the underlying reason behind each one, so founders are never blindsided in meetings.
Durkin founded 99dresses at 18, got into YC, lost her co-founders, and watched committed funding fall through at the worst moment, killing the company. An emotionally raw account of a collapsed round, visa pressure, and winding down.
The viral 2015 essay, written while Hamilton was broke and pitching her fund, calling out venture's failure to fund underrepresented founders. It directly led to her first LP check and the founding of Backstage Capital.
The Monzo and GoCardless founder (later YC partner) condenses raising ~$400M across six years into a practical guide: sequencing angels before VCs, running a tight process, and why business quality dominates fundraising tactics.
Altman observes that the best investments he's made were rounds nobody else wanted, and the hottest, most oversubscribed seed rounds mostly produced mediocre outcomes. Explains why consensus and quality are inversely correlated at seed.
A 4x founder turned VC lays out what actually drives fundraising outcomes beneath the standard advice: psychology, sequencing, the 'ladder of proof', and how VCs really talk about deals internally.
Index to Feld and Mendelson's 2005 series explaining every clause of a VC term sheet: liquidation preferences, anti-dilution, protective provisions, drag-along, and which terms actually matter. Later became the book Venture Deals.
Bessemer publishes the actual internal investment recommendation memos behind its best deals, showing exactly how partners argued for LinkedIn, Shopify, Pinterest and others: the risks flagged, the numbers at the time, and the bet being made.
Tovala founder David Rabie recounts the moment his Series B fell apart, what it felt like, how the company survived, and how they eventually got funded anyway.
Breslow frames fundraising as a game with learnable rules and lists the ten most common founder mistakes, including building investor relationships too late, over-long decks (VCs spend ~3 minutes on a deck), and taking rejection personally.
Backstage Capital's Arlan Hamilton on going from homeless to VC, her $5M crowdfunding raise for her own firm, and educating underestimated founders on how capital actually works.
A Founder Collective GP flips the diligence table: twelve specific questions founders should ask potential investors (fund size, reserves, decision process, references) instead of only optimizing for getting to yes.
Dalton Caldwell and Michael Seibel break down rookie mistakes founders make around investor terms and incentives: what investors actually optimize for, misaligned terms to watch, and how naive founders get squeezed.
A plain-English glossary thread decoding term sheet vocabulary (liquidation preferences, pro rata, anti-dilution and more) for first-time founders and new VCs, written before Doherty founded Behind Genius Ventures.
A first-time founder of virtual-workspace startup Branch narrates his first seed raise: struggling with traditional VC, generating ~$4M in commitments largely through online friends, and learning that 'money is expensive' — taking every offer would have cost over 30% of the company at seed.
Wilkinson, who built Tiny to hundreds of millions in revenue without VC, explains the structural problem with venture money: in the VC's portfolio math you're either a zero or a billion-dollar company, which forces risky bets on companies that could have been excellent linear businesses.
Helgesen relays a tactic from a mentor who raised $500M+ and went public: never accept a VC's term sheet — send your own, with a hard deadline and only two blanks (price and amount). Week 1 set meetings, week 2 pitch and send the term sheet, week 3 review offers and sign, exploiting the fact that VCs behave completely differently on 'hot' deals.
Pincus recalls pitching Zynga in 2007, when no firm wanted to back the company, to a partner who fell asleep mid-pitch. Zynga went on to a multi-billion-dollar IPO.
Kalanick describes intercepting a VC who was fleeing his own office to avoid their 2001 meeting, then pitching him from the passenger seat of the investor's parked Lexus during the dot-com winter.
Base44 founder Maor Shlomo explains building solo to an $80M exit in six months without raising venture capital, including why he turned down VC interest and how that shaped the Wix acquisition.
Stitch Fix founder Katrina Lake at Stanford ETL on building the company through investor skepticism about women's retail, raising less than peers, and going public anyway.
Aggregates advice from founders and investors who have collectively seen 1,000+ seed raises, organized as a step-by-step process with benchmarks for round size, dilution, timeline, and meeting counts.
Front CEO Mathilde Collin discusses her famously fast Series A and B processes, including the transparent metrics emails she sent investors and how she created competitive dynamics.
A former a16z partner turned founder describes how different fundraising looks from the founder's chair: what she got wrong despite knowing the investor side, and the gap between VC theory and founder practice.
Zapier CEO Wade Foster explains why the company raised only a tiny seed round and never went back to the well, plus contrarian takes on growth and hiring that follow from profitability.
Wilson's short, sharp definition: seed money is for building product and finding product-market fit, nothing else, and rounds sized or spent otherwise create broken cap tables and stranded companies.
Dixon's classic warning about signaling risk: when a large multi-stage VC seeds you and then declines to lead your A, the market reads it as a kiss of death, regardless of your actual progress.
Danco argues that recurring-revenue businesses funding predictable growth with dilutive equity is a historical accident, and predicts the rise of revenue-based and debt financing for startups. Sparked a wide industry debate.
Bessemer's famous public list of the legendary companies it passed on, with self-deprecating explanations ('friend rented her garage to Google's founders; David asked how he could leave the house without going near it').
Suster's process playbook: qualify investors like a sales pipeline, research partners not firms, sequence your best prospects after warm-up meetings, and manage the raise like an enterprise deal.
Sequoia's Julien Bek takes 20VC inside the firm's investment committee: how the SpaceX and Citadel deals actually went down, how memos are argued, and what kills deals at partnership.
Johnson's much-debated argument that the warm-intro requirement is not just exclusionary but bad investing: it selects for network proximity over merit, and firms serious about returns should build open top-of-funnel instead.
The essay that explained the 2021 Tiger Global phenomenon: how deployment velocity, price insensitivity, and low-friction terms let some funds play an entirely different game, and what that means for founders choosing among capital providers.
Graham on the substance of persuasion: convince yourself first, be a domain expert, and make the truth about your startup legible rather than performing confidence you don't have.
The 1/(1-n) rule: give up n% of your company only when the trade makes the remaining stake worth more than the whole was before. Applies the same math to investors, hires, and co-founders.
Argues for rolling closes on convertible instruments instead of monolithic rounds: take committed money immediately, reward early conviction with better terms, and dissolve the herd-waiting equilibrium among seed investors.
Defines the default-dead trap: moderate growth, months of runway, and an assumption investors will save you. Explains why bridge rounds usually don't come and what to do instead (cut costs or grow into default-alive).
Graham explains power-law returns from the investor side: the best ideas look like bad ideas, YC's returns come from a handful of companies, and even professionals can't reliably pick winners at the time of investment.
Seibel's formulaic, repeatable pitch structure: a two-sentence company description anyone can repeat, traction, unique insight, market size, and the ask, with examples of each done well and badly.
Seibel on the mechanics of leverage: investors respond to scarcity and competition, so batch your meetings, create parallel processes, and never negotiate from a single-bidder position.
Distilled from YC's Series A program data: how A rounds actually happen, why 'we'll preempt you' conversations mislead founders, benchmark metrics, and running a deliberate A process instead of drifting into one.
Yin documents raising Hustle Fund I with funnel numbers: hundreds of LP conversations, conversion rates, and tactics. Fundraising for a fund mirrors a startup raise, and she shows the whole pipeline including the rejections.
Polovets enumerates the specific risks investors price (team, market, product, execution, financing) and concrete actions that retire each one, reframing fundraising as selling reduced risk at increasing prices.
A seed VC analyzes 71 tech IPOs and finds no correlation between capital raised and outcome quality: the most efficient companies returned more per dollar than the most funded. Argues overcapitalization is a drug with real side effects.
The actual deck behind Front's $66M Sequoia-led Series B, published with commentary on how the narrative evolved from the Series A and what growth evidence carried the round.
Sequoia's actual 2005 YouTube Series A memo, made public through the Viacom lawsuit: written when YouTube was two months old with no CEO and no business plan, it shows how a top firm underwrote a raw, risky deal.
The definitive reported account of Everpix's death: a beloved product with paying users that ran out of runway mid-raise; the founders later open-sourced their pitch decks, metrics, and investor pipeline. A masterclass in how good products die from failed fundraises.
Rella co-founder Natalie Barbu documents exactly how she closed a $1M pre-seed round as a first-time founder: her investor pipeline, the number of meetings, how she handled passes, and the close.
A founder who failed 22 times before building a $2.5B company tells My First Million the full arc, including the fundraising dead-ends, near-bankruptcies, and the raise that finally worked.
A step-by-step seed fundraising process from a pre-seed VC: build a tiered investor list, gather external feedback on materials, and run the raise as a structured pipeline rather than ad-hoc meetings.
A compilation of seed-raising heuristics anchored on a Paul Graham paraphrase: pretend you're the VC, adopt their incentives, and convince yourself you'd invest — then that you could convince your partners too.
Founder Collective's content lead tears down the pitch deck team slide, the slide that looks most identical across all startups, and shows concrete ways to make individual achievements legible to investors.
Lemkin dissects a real cold email he received: an interesting startup near $2M ARR with no funding that killed its own chances by asking for an oversized round. He explains how ask size instantly reprices the deal in an investor's head.
Collin announces Front's $65M Series D (Salesforce Ventures, Battery) at the bottom of the 2022 downturn, linking her written reflections. She is the rare founder who has published her actual Series A, B, and C decks publicly, with commentary; her Series B was famously 11 investor pitches over five days yielding 10 offers.
Yin unpacks the rise of tiny angel checks: who writes $1K checks, why they aren't a waste of cap table space, and how operators-turned-micro-angels change early round construction.
ICEYE co-founder Rafal Modrzewski on raising for a satellite company in Europe: convincing investors to fund hardware with long timelines, and how each round's story evolved.
Wessel, now a First Round partner, recalls a 2015 Series A pitch where one famous partner slept and another scowled throughout, then the firm sent a term sheet two hours after IC and was shocked she declined.
Chemistry's Mark Goldberg (ex-Index) on why decision-making is broken inside large VC firms: politics, consensus damage, and what that means for founders pitching them.
Stanford GSB professor Ilya Strebulaev summarizes his large-scale research on how venture capitalists actually make decisions: what they weight (team vs market vs product), how many deals they screen, and how valuations are really set.
Named and documented the solo-capitalist phenomenon: individual investors raising nine-figure funds and winning competitive rounds against firms, and what founders gain and lose by taking their money.
Union Square Ventures' Fred Wilson in a long-form TWiST conversation on how USV picks investments, his views on founder-investor relationships, and stories from Twitter/Tumblr-era deals.
Practical demo-day-era advice on presenting: explain what you do in the first sentence, show a demo, and optimize for being understood rather than impressive.
Suster argues against DocSend-style gated links from the receiving end: friction kills investor attention, deck-tracking paranoia is misplaced, and your deck's job is to travel inside the partnership without you.
YC partner Aaron Harris's operational seed-raising manual: preparing materials, building the target list, running meetings in a compressed window, and closing with SAFEs.
The official home of the SAFE: current post-money SAFE documents, side letters, and YC's user guide explaining caps, discounts, and dilution math.
Three years after the unusual angel round, Fishkin reports real numbers: profit-sharing distributions actually paid to investors, growth against plan, and honest assessment of the model's tradeoffs.
Former YC president Geoff Ralston's fundraising fundamentals lecture: round mechanics, dilution math, SAFEs, investor psychology, and process design for a first raise.
YC CFO Kirsty Nathoo explains SAFEs versus priced rounds with worked cap table examples, showing exactly how caps, discounts, and stacking SAFEs dilute founders.
Altman on the pattern where startups treat closing a round as the achievement, coast afterward, and die: fundraising success is a lagging indicator that buys time, nothing more.
YC's Aaron Harris on how to get meetings with investors and run them: intro paths, meeting stagecraft, reading interest honestly, and converting interest into checks.
Gil maps what each round is actually evaluated on: seed buys the team and idea, A buys early product signal, B buys proof the machine works, C buys scaling economics, with implications for what to emphasize at each.
The index post for Wilson's MBA Mondays series covering every startup financing option: friends and family, angels, convertible debt, venture debt, preferred rounds, and when each fits.
DocSend's dataset of thousands of real fundraising decks quantifies the seed raise: how many meetings successful raises take, how long investors actually read decks, which slides funded decks include, and seasonal timing effects.
YC's Kevin Hale on pitch construction: clarity, the 'legible, obvious, conductive' framework, and live rewrites of muddled startup one-liners.
Part of Andreessen's legendary 2007 startup guide, written as a founder before a16z existed: how to size a raise against milestones and market windows, the pathologies of too little money and the subtler pathologies of too much.
Tunguz's index of his data-driven fundraising posts organized as a founder's guide: how VCs decide, round dynamics, valuation math, and negotiation, each backed by his analyses of actual funding data.
Janz describes later-stage investors pressuring founders to restructure or squeeze out early angels and seed funds, and argues founders must defend the people who took the earliest risk, both morally and reputationally.
A SaaS-focused VC admits the venture model's power-law needs are increasingly mismatched with how most healthy SaaS companies actually grow, and explores what that means for founders choosing capital.
Aaron Harris's deep guide to raising a Series A: metrics thresholds, building investor relationships pre-raise, running the process, and partner-meeting dynamics.
The third installment in Collin's published-deck series: the actual deck behind Front's $59M Series C, showing how a growth-stage narrative differs from the A and B stories she'd already published.
An Australian health-tech founder walks through raising a $5M seed round led by Blackbird: how the process ran, what materials mattered, and what surprised them.
Haus.com CEO Jonathan McNulty explains how the company raised a $7.13M seed round that included Tim Ferriss, covering how they built the investor list and landed non-traditional angels.
A young founder gives a step-by-step retrospective of raising $5M: sourcing investors, sequencing meetings, creating urgency, and closing, with real artifacts from the raise.
Ex-YC founder Diego Rojas (Shieldbase AI) shares fundraising lessons across YC and post-YC rounds, including what worked in investor conversations for an AI startup and what he'd do differently.
Brian Chesky reads an actual rejection letter Airbnb received from an investor, then unpacks what the rejections got wrong and how the founders kept going.
Yin argues investors over-index on TAM slides while founders under-argue market pull and go-to-market, and explains what she actually wants to see instead of a top-down market-size number.
A short thread on what actually gets hard after the seed closes: shifting from founder heroics to team-building, and setting up the metrics trajectory the Series A will be judged on.
sennder co-founder David Nothacker walks through his company's first fundraise at Slush's founder school: what worked in the process, mistakes made, and how they picked investors.
Iskold advises founders who recently closed sub-$2M rounds with momentum to open a SAFE at a higher cap and keep taking money, explaining the runway-as-leverage logic in a down market.
A longevity startup founder explains to TWiST why they raised in Japan instead of Silicon Valley: investor appetite differences, valuation trade-offs, and cross-border round mechanics.
A female founder and her investor jointly recount going from seed to Series A during the pandemic: both sides of the same deal, including what the VC saw internally.
A seed VC lists concrete behaviors investors should adopt in pitch meetings — pitch yourself first, show vulnerability, don't check your phone — acknowledging how stressful pitching is for founders.
A crowdsourced-and-curated list of 25 best-practice traits for early-stage VCs, cc'ing prominent investors who debated it in replies; a useful rubric for founders scoring prospective investors.
Chen's much-quoted maxim: the #1 fundraising mistake is treating the pitch deck as a delivery vehicle for facts when it is actually a delivery vehicle for emotions. It anchored his broader public work on narrative-driven deck design at Runway.
The closing post of Chen's June 2020 thread offering Black founders direct, live pitch feedback, the kind VCs are typically uncomfortable giving, naming the candor gap as a concrete fundraising disadvantage.
Bill Gurley argues venture capital is structurally a bad industry: excess capital, misaligned incentives, and what that means for founders taking money at peak prices.
Lavingia's post pointing to his 'How to Raise A Crowdfunding Round' guide, drawn from Gumroad's landmark March 2021 Reg CF raise: $5M in 12 hours from 7,303 investors (5,800+ first-time angels) at the newly raised legal cap.
Benchmark's Bill Gurley with Bloomberg on the VC landscape, staying private too long, and lessons from Uber's capital raising for founders and boards.
Angel investor Alicia Syrett catalogs the real reasons angels and VCs say no — most of which founders never hear — drawn from hundreds of her own pitch meetings.
Written at the start of the 2022 correction, the Skillshare founder predicts an unprecedented wave of shutdowns, layoffs, and down rounds over the following 18 months and lays out how founders should get to default alive before the fundraising window closes.
Hustle Fund's Elizabeth Yin on her high-volume portfolio strategy, how tiny first checks change the founder-VC dynamic, and her outlook on seed fundraising.
Elizabeth Yin's three concrete tips for raising a Silicon Valley seed round as an outsider, from her experience as both a funded founder and a fund GP.
Freestyle's Jenny Lefcourt on making non-consensus bets, avoiding hype-driven investing, and what founders misread about how seed VCs form conviction.
Jenny Lefcourt walks through her 'ultimate pitch' framework slide by slide, showing exactly what a seed VC wants in each part of the deck and the meeting.
Mark Suster returns to TWiST on the ANGEL podcast: alignment between founders and investors, setting reality with your board, and raising in down markets.
Plain-language breakdown of what pre-seed, seed, and A actually mean now, what each stage's investors expect, and how round sizes and expectations have drifted from the labels.
Mercury CEO Immad Akhund on launching a $26M fund, what he learned angel investing in 350+ startups, and what founder behaviors predict successful raises.
20VC roundtable arguing why the venture market today is structurally worse than the 2021 peak: pricing, AI concentration, and exit math — and what founders should do about it.
VenCap's David Clark shares 32 years of fund-of-funds data: how few companies drive all venture returns, and what that power law means for how VCs must behave with founders.
Launch post for Raise Millions, Hustle Fund's free book-length compilation of tactical fundraising guidance drawn from thousands of pre-seed pitches; the post links the full free resource.
YC founders confess their actual fundraising mistakes: optimizing for valuation, taking bad money, serial meetings, and misreading investor interest.
Michael Seibel's practical guide to cold-emailing investors: structure, brevity, credibility signals, and real examples of what gets a reply.
A founder who raised $1.5M+ across UK and US investors documents the whole process as a manual: what worked, the traps she fell into, and differences between London and Valley investor behavior.
Dalton and Michael debate when a startup should bootstrap versus raise venture capital, including honest talk about which businesses are venture-shaped at all.
A First Round partner's standing advice to new portfolio founders, including how to work with investors after the round closes and how to set up the next raise from day one of this one.
Founders at YC's Female Founders Conference compare fundraising experiences: rejection patterns, investor bias, and tactics that worked, with disagreement between panelists on the right approach.
A book-length, edited, citation-heavy reference on the entire venture fundraising process, from instruments and terms through negotiation and close, reviewed by dozens of practitioners.
YC's Carolynn Levy (inventor of the SAFE) and Kirsty Nathoo teach investor-school mechanics: instruments, rights, and what founders and angels each misunderstand about early-stage paperwork.
Newcomer interviews Substack's founders immediately after their $100M round at $1.1B: how the round came together after a rocky stretch (including a crowdfunded raise when VCs cooled), and how the narrative was rebuilt.
An analytical companion to Lavingia's essay: Baschez unpacks the structural reasons venture-backed Gumroad 'failed' at billion-dollar scale while succeeding as a business, examining how funding choices define what counts as success.
At TechCrunch Disrupt 2024, VCs give live unrehearsed feedback on audience members' actual pitch decks, disagreeing with each other about what works.
Wilson candidly reviews USV's own seed investing record and explains how a multi-stage firm actually thinks about seed checks, follow-ons, and the reserved-capital math behind them.
Hustle Fund reviews a real startup's deck slide by slide, narrating the investor's inner monologue and cataloging the seven mistakes they see most at pre-seed and seed.
Data analysis showing Series B is statistically the hardest round: seed enthusiasm has faded, growth-stage proof isn't in yet, and the company is valued on early scaling evidence alone.
Quantifies the second-seed phenomenon: how common repeat seed rounds are and what they do, statistically, to a company's Series A odds and terms.
Walk reframes seed as a multi-year, possibly multi-round phase of proving core value, not a single event, with implications for how founders should structure and sequence early capital.
A short, sharp diligence-reversal tactic: ask every prospective investor 'what's a risk you're more comfortable with than the average VC?' and use the answer to test fit and conviction.
Wilson Sonsini partner Becki DeGraw walks TWiST through negotiating a term sheet: which terms actually matter, market norms, and where founders should spend negotiating capital.
A sitting VC interrogates his own industry's meritocracy narrative: standard fundraising advice assumes network access and pattern-matching benefits that underrepresented founders don't get, and he discusses what honest advice looks like instead.
TWiST legal-basics episode on board seats: why you effectively can't fire a VC from your board, and the cautionary situations that produces.
An early definition of the pre-seed round from one of the investors who named the category: what qualifies ($750K or less, pre-product), why the category emerged, and how it chains into institutional seed.
With founders now raising 3-4 rounds before Series A, Go argues the total dilution math forces a choice: decide deliberately which round in the chain you'll skip, and shows how to reason about it.
The leading pre-seed investor argues stage labels below Series A have lost meaning: everything before the A is one continuous proving period, and founders should plan capital and milestones accordingly.
Aaron Harris on fundraising in the AI era: how AI company valuations diverge from SaaS norms, what investors currently over- and under-weight, and process implications.
Jason Calacanis answers founder questions about raising a seed round in 2026: current check sizes, AI-market dynamics, accelerator math, and what he funds today.
Jason Lemkin's fundraising workshop on what it takes to get funded now: real conversion rates from pitch to check, and what SaaS metrics clear the bar.
Point Nine's Christoph Janz presents the five metrics that matter when raising a SaaS Series A and B, with the benchmark ranges his fund actually uses.
Morrill explains publicly why Mattermark took a $2M second seed instead of the Series A she'd been pitching: two years of nonstop fundraising, a bridge from a customer-investor, and the honest math of raising below your hopes.
TechCrunch Live pairs a founder with the VC who led their Series A to reconstruct the deal: first contact, diligence, the partner meeting, and the close.
After raising a $500K seed and then nearly running out of money, Pigford describes negotiating with his investors to reset expectations and step off the venture growth track, with the actual numbers Baremetrics published all along.
Startup Grind panel on overcoming bias while fundraising as an underrepresented founder, with firsthand accounts of coded feedback and the workarounds that got checks written.
YC co-founder Jessica Livingston on entrepreneurship through the venture lens: stories from early YC batches, what founders misread about investors, and how the best founders handled early fundraising.
Sendbird CEO John Kim on why most startup CEOs fail, drawing on his own near-death fundraising moments and what actually earned investor conviction.
Frames fundraising as a status game and provides 20 specific questions founders can ask in VC meetings to signal selectivity and flip the chase dynamic.
From years of sitting in board rooms, an investor shares how first-time founders can run board meetings well: preparation, pre-reads, and engaging members strategically instead of presenting at them.
Reid Hoffman on setting fundraising goals and choosing investors as fundamental partners rather than money sources.
Allred announces Lambda School's $14M GV-led Series A with a two-word nod to Elon Musk's infamous 'funding secured' tweet. An artifact of the ISA-education hype cycle whose later unraveling gives it a cautionary second reading.
Marc Andreessen explains in two minutes what a16z actually looks for in startups and why strength of insight beats polish.
Chamath announces Social Capital's Emerging Managers program: money, training, and community for aspiring investors from diverse, nontraditional backgrounds — the other side of the fundraising table, on who gets to allocate capital.
Bill Gurley on why founders and investors over-index on TAM slides, with examples of huge companies whose initial TAM looked tiny.
Sheel Mohnot tells the story of raising his first VC fund — the LP rejections, weird meetings, and scrappy tactics — a mirror image of founder fundraising.
NextView's Rob Go gives the ultimate guide to raising a venture fund: LP targeting, momentum, first closes — directly analogous to a startup round and full of transferable tactics.
Michael Seibel explains why fundraising works differently in Silicon Valley than everywhere else: risk appetite, check-writing speed, and what that means for founders elsewhere.
Seibel contrasts pitching investors with pitching customers: investors buy the upside story and the market, customers buy the solution — and mixing the two kills both.
Dalton and Michael respond to criticisms of Y Combinator and explain how YC actually affects fundraising outcomes, including honest discussion of demo day dynamics.
A repeat founder and angel condenses his raising experience into a toolkit: list-building, sequencing angels and funds, materials, and close mechanics, with templates.
Dalton Caldwell and Michael Seibel at TechCrunch on YC do's and don'ts, including how founders should think about applying, demo day, and post-batch fundraising.
A young founder's candid, funny account of the performative side of fundraising: manufacturing 'I happen to be in town' moments, reading investor signals, and the theater everyone pretends isn't happening.
Recent YC Startup School session defining the key terms founders must know before raising: SAFEs, caps, pro rata, option pools, board seats, and liquidation preferences in plain language.
Founders pitch live at Startup Summit and get immediate teardown feedback from a founder-turned-GP, covering deck structure, delivery, and fundability.
VC Peter Harris rips apart a real pitch deck for Appointment.com on camera, slide by slide, explaining what he'd need to see to invest.
NFX's James Currier maps the four types of pitch decks and the six things a VC must know by the end of any of them.
Classic Stanford GSB session walking through a venture term sheet clause by clause with the negotiating dynamics behind each term.
The investor-side view of pre-seed construction: why NextView prefers small aligned syndicates over large party rounds at this stage, and what that means for founders assembling one.
Hustle Fund explains the YC SAFE and dilution with worked examples: post-money caps, stacking, and the cap table founders actually end up with.
Uses a $7.3M seed round raised by an American founder for a Nigerian-market app to examine who global VC actually trusts to build in Africa, and what local founders face by comparison.
Jason Lemkin and Founders Fund's Sam Blond on raising in the late-2022 downturn: what changed in diligence, pricing, and which companies could still raise.
A former VC who crossed to the founder side demystifies the seed process from both chairs: board seats, how much to raise, investor selection, and the parts of VC behavior that only make sense once you've sat in the partner meeting.
SaaStr session on six things no one tells you about raising a seed round: the emotional arc, ghosting, party-round pitfalls, and closing dynamics.
SaaStr session on the risky business of Series B: why it's the hardest round, what growth-stage investors diligence, and the trap of a too-high Series A price.
Written inside the COVID shock: a VC candidly reports what his firm and peers were actually doing (versus saying) about new deals, and advises founders on raising into a frozen market.
Lemkin's blunt list of first-founder mistakes, the fundraising ones foremost: assuming the next round is guaranteed, burning to a plan that requires it, and wasting months pitching the wrong investors.
Stanford CS183F Startup School session on how to raise money and succeed long-term, connecting fundraising decisions to company outcomes years later.
Kruze Consulting's Scott Orn on writing investor updates that work: cadence, structure, the ask section, and how updates set up the next round.
Stanford GSB's Building Momentum session on diversity in venture fundraising: data on funding gaps plus firsthand founder and investor accounts.
Stanford's Grit & Growth episode on fundraising as a marathon, following emerging-market founders through multi-year capital journeys across grants, angels, and VC.
Slush fireside chat on the psychology of raising money: fear, rejection resilience, and the mental game of a raise, told through the speakers' own rounds.
Seedcamp's Carlos Espinal teaches raising capital at Slush's founder school, drawing on his book 'Fundraising Field Guide' and hundreds of Seedcamp deals.
Dash0 founder Mirko Novakovic (previously Instana) on raising a Series A as a repeat founder: how his second-time process differed and what investors preloaded.
Harry Stebbings interviewed about his own raises: building 20VC's funds from a bedroom podcast, being underestimated, and what pitching LPs taught him about pitching generally.
Long-form biography interview with Harry Stebbings on raising $800M in funds starting at 18: LP rejections, the grind, and specific fund-raise mechanics.
AIVA TECH co-founder Lucia Mari Sanguino details raising a $1.5M pre-seed: the funnel, the materials, investor objections, and how the round finally assembled.
A recent example of the raise-announcement-as-explainer genre: XO Market breaks down what it raised in its $6M seed, what problem the round funds, and what comes next.
First Round's Bill Trenchard on pitch deck structure: ordering slides to build conviction and where most decks lose the room.
Early TWiST legal-basics segment on raising from angels: convertible instruments, accreditation, and the paperwork of a first close.
Slidebean's Caya compares SAFEs, convertible notes, and KISS instruments with real numbers, from his own experience raising for Slidebean.
TechCrunch session on building a later-stage investor network before you need it: mapping funds, nurturing relationships between rounds, and sequencing outreach.
TK Kader's structured walkthrough of preparing for a Series A after seed: milestone planning, narrative building, and process timing.
A walkthrough of raising startup funding as a first-time founder, from someone who raised angel through Series B as a solo founder in Silicon Valley.
Startup Boston bootcamp on raising a seed round: process design, materials, investor targeting, and Q&A with local founders and investors.
Jason Calacanis explains how to cold-email angel investors in a way he'd actually answer, with the exact structure and signals he looks for.
Mark Suster's 'Always Be Raising' doctrine in brief: relationship-building between rounds so the round itself is a formality.
Mark Suster on qualifying which VCs are actually right for your startup: stage fit, check size, partner-level fit, and portfolio conflicts.
NFX on why VCs now expect founders to move dramatically faster, and how speed itself became the core fundraising signal in the AI era.
Slush session on raising rounds above $10M in Europe: which funds can lead, transatlantic dynamics, and how European growth rounds differ from US ones.
Pear VC's Pepe Agell at Slush on raising your first round: readiness signals, meeting dynamics, and how Pear decides on pre-seed companies.
Flagship's David Berry on fundraising for deep tech: milestone-based financing, syndicate construction, and communicating scientific risk to generalist investors.
Uncapped founder Piotr Pisarz makes the case for revenue-based funding as an alternative to venture equity, explaining who it suits and its real costs.
Edith Yeung on fundraising globally: how investor expectations differ across the US, China, and Southeast Asia, and how founders should adapt the pitch per market.
Web Summit panel on finding the right VC match: founders and investors debate how much fit matters versus just taking the money.
Web Summit session on managing the investor-founder relationship after the round: boards, conflict, and keeping investors useful.
Web Summit hyper-growth panel on fundraising at scale: raising ahead of need, mega-round dynamics, and the costs of blitzscaling capital.
Startup Grind panel on managing a downturn and fundraising through it: runway math, investor communication, and which rounds are possible in a frozen market.
Startup Grind London panel on the snakes and ladders of fundraising: founders trade stories of near-misses, lucky breaks, and process disasters with investor commentary.
Startup Grind breakout on fundraising and valuation for AI startups: how AI valuations are being set in the current market and what justifies premium pricing.
Stella & Dot founder Jessica Herrin and Jenny Lefcourt — co-founders together in the 90s — compare notes across founder and investor seats on what raising money really takes.
Web Summit talk on winning funds and influencing investors: pitch psychology and meeting dynamics from the investor's chair.
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