114 talks, interviews, and teardowns, ranked and summarized: founders who survived a hundred rejections, VCs explaining exactly how they decide, and lawyers walking through the term sheet line by line.
1h 6m
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.
1h 9m
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.
28 min
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.
26 min
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.
58 min
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.
1h 26m
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.
47 min
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.
4 min
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.
1h 0m
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.
9 min
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.
22 min
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.
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.
21 min
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.
47 min
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.
47 min
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.
8 min
Sendbird CEO John Kim on why most startup CEOs fail, drawing on his own near-death fundraising moments and what actually earned investor conviction.
1h 31m
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.
51 min
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.
21 min
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.
1h 7m
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.
12 min
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.
25 min
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.
23 min
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.
1h 11m
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.
23 min
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.
1h 28m
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.
56 min
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.
6 min
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.
3 min
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.
8 min
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.
53 min
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.
1 min
Reid Hoffman on setting fundraising goals and choosing investors as fundamental partners rather than money sources.
1 min
Marc Andreessen explains in two minutes what a16z actually looks for in startups and why strength of insight beats polish.
1 min
Bill Gurley on why founders and investors over-index on TAM slides, with examples of huge companies whose initial TAM looked tiny.
9 min
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.
1h 3m
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.
10 min
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.
1h 11m
Freestyle's Jenny Lefcourt on making non-consensus bets, avoiding hype-driven investing, and what founders misread about how seed VCs form conviction.
53 min
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.
1h 7m
Mark Suster returns to TWiST on the ANGEL podcast: alignment between founders and investors, setting reality with your board, and raising in down markets.
11 min
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.
1h 4m
Mercury CEO Immad Akhund on launching a $26M fund, what he learned angel investing in 350+ startups, and what founder behaviors predict successful raises.
1h 34m
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.
1h 20m
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.
1h 7m
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.
52 min
Former YC president Geoff Ralston's fundraising fundamentals lecture: round mechanics, dilution math, SAFEs, investor psychology, and process design for a first raise.
45 min
YC CFO Kirsty Nathoo explains SAFEs versus priced rounds with worked cap table examples, showing exactly how caps, discounts, and stacking SAFEs dilute founders.
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.
7 min
YC founders confess their actual fundraising mistakes: optimizing for valuation, taking bad money, serial meetings, and misreading investor interest.
3 min
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.
7 min
Michael Seibel's practical guide to cold-emailing investors: structure, brevity, credibility signals, and real examples of what gets a reply.
6 min
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.
27 min
YC's Kevin Hale on pitch construction: clarity, the 'legible, obvious, conductive' framework, and live rewrites of muddled startup one-liners.
14 min
Dalton and Michael debate when a startup should bootstrap versus raise venture capital, including honest talk about which businesses are venture-shaped at all.
Dalton and Michael respond to criticisms of Y Combinator and explain how YC actually affects fundraising outcomes, including honest discussion of demo day dynamics.
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.
33 min
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.
59 min
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.
17 min
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.
36 min
At TechCrunch Disrupt 2024, VCs give live unrehearsed feedback on audience members' actual pitch decks, disagreeing with each other about what works.
25 min
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.
27 min
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.
4 min
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.
3 min
First Round's Bill Trenchard on pitch deck structure: ordering slides to build conviction and where most decks lose the room.
22 min
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.
24 min
TWiST legal-basics episode on board seats: why you effectively can't fire a VC from your board, and the cautionary situations that produces.
53 min
Classic Stanford GSB session walking through a venture term sheet clause by clause with the negotiating dynamics behind each term.
15 min
Early TWiST legal-basics segment on raising from angels: convertible instruments, accreditation, and the paperwork of a first close.
17 min
Hustle Fund explains the YC SAFE and dilution with worked examples: post-money caps, stacking, and the cap table founders actually end up with.
11 min
Slidebean's Caya compares SAFEs, convertible notes, and KISS instruments with real numbers, from his own experience raising for Slidebean.
58 min
Aaron Harris's deep guide to raising a Series A: metrics thresholds, building investor relationships pre-raise, running the process, and partner-meeting dynamics.
46 min
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.
57 min
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.
24 min
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.
SaaStr session on six things no one tells you about raising a seed round: the emotional arc, ghosting, party-round pitfalls, and closing dynamics.
23 min
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.
55 min
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.
30 min
TechCrunch session on building a later-stage investor network before you need it: mapping funds, nurturing relationships between rounds, and sequencing outreach.
19 min
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.
56 min
Startup Boston bootcamp on raising a seed round: process design, materials, investor targeting, and Q&A with local founders and investors.
53 min
Stanford CS183F Startup School session on how to raise money and succeed long-term, connecting fundraising decisions to company outcomes years later.
24 min
Kruze Consulting's Scott Orn on writing investor updates that work: cadence, structure, the ask section, and how updates set up the next round.
8 min
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.
1 min
Mark Suster's 'Always Be Raising' doctrine in brief: relationship-building between rounds so the round itself is a formality.
2 min
Mark Suster on qualifying which VCs are actually right for your startup: stage fit, check size, partner-level fit, and portfolio conflicts.
9 min
NFX on why VCs now expect founders to move dramatically faster, and how speed itself became the core fundraising signal in the AI era.
49 min
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.
52 min
Stanford GSB's Building Momentum session on diversity in venture fundraising: data on funding gaps plus firsthand founder and investor accounts.
30 min
Stanford's Grit & Growth episode on fundraising as a marathon, following emerging-market founders through multi-year capital journeys across grants, angels, and VC.
11 min
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.
24 min
Slush session on raising rounds above $10M in Europe: which funds can lead, transatlantic dynamics, and how European growth rounds differ from US ones.
23 min
Seedcamp's Carlos Espinal teaches raising capital at Slush's founder school, drawing on his book 'Fundraising Field Guide' and hundreds of Seedcamp deals.
27 min
Pear VC's Pepe Agell at Slush on raising your first round: readiness signals, meeting dynamics, and how Pear decides on pre-seed companies.
26 min
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.
28 min
Flagship's David Berry on fundraising for deep tech: milestone-based financing, syndicate construction, and communicating scientific risk to generalist investors.
26 min
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.
21 min
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.
23 min
Web Summit panel on finding the right VC match: founders and investors debate how much fit matters versus just taking the money.
18 min
Web Summit session on managing the investor-founder relationship after the round: boards, conflict, and keeping investors useful.
21 min
Web Summit hyper-growth panel on fundraising at scale: raising ahead of need, mega-round dynamics, and the costs of blitzscaling capital.
15 min
Web Summit talk on winning funds and influencing investors: pitch psychology and meeting dynamics from the investor's chair.
1h 7m
Startup Grind panel on managing a downturn and fundraising through it: runway math, investor communication, and which rounds are possible in a frozen market.
58 min
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.
26 min
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.
29 min
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.
1h 7m
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.
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.
1h 30m
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.
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