Every case

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• Revolut raises $500M at a $5.5B valuation on the app-bank bet2018–2020
• OneDev launches a lightweight GitLab alternative and grows to 15.2k stars2020
• LogMeIn's GoToMeeting buy bet ends in a $4.3B PE sale2016–2020
• Hasura raises $9.9M on a bet that instant GraphQL APIs beat backend glue2018–2020
• HashiCorp raises $175M at $5.1B on the enterprise multi-cloud bet2020
• DigitalOcean raises $100M in debt as its SMB cloud nears $300M in revenue2016–2020
• Aurora absorbs Uber ATG; $400M Uber stake values the merger at $10B2017–2020
• Story Creator App bets easy web video beats After Effects for non-designers; HN 8682019–2020
• Optimizely's enterprise pivot ends in sub-$600M Episerver sale; ex-staff: bad exit2010–2020
• MockMechanics bets mechanical programming needs physical intuition, not syntax; HN 7192018–2020
• Kosmi bets browser-streamed PS1 rooms revive couch co-op; HN gave it 676 points2020
• StudioMDHR mortgaged homes to finish Cuphead; the 1930s-style bet sold 6M copies2010–2020
• Fawry's corner-shop bet: Egypt's first fintech IPO in 2019, billion-dollar cap by 20202008–2020
• honestbee: premium grocery delivery scaled to 8 countries, then collapsed owing S$319.9M2015-2020
• Freepik: bootstrapped Spanish stock-image platform sells majority stake after a decade2010–2020
• Yalla's voice-chat bet: first UAE tech IPO on NYSE raises $139.5M2016–2020
• Paystack bet Nigerian businesses wanted a simple payments API; Stripe bought it for $200M+2015-2020
• InstaShop's Gulf grocery bet pays off: Delivery Hero buys the Dubai app for $360M2015–2020
• Veeam bootstrapped VMware backup to $1B revenue, then sold for $5B2006–2020
• Careem's bet on local ride-hailing paid off when Uber bought the Dubai startup for $3.1B2012–2020
• BarbBlock bets DMCA threats against blocklists backfire via an automated Streisand effect2017–2019
• Discord's game-store bet: $150M at a $2.05B valuation to challenge Steam at 90/102018–2019
• WeWork's IPO bet unravels: its $47B private valuation slides toward a $10B float2010–2019
• Wag takes $300M from SoftBank to scale dog walking, then loses share to Rover2015–2019
• Travis CI, the open-source CI that reached 700,000 users, sells to Idera2011–2019
• Slack's direct listing closes day one near $20B after betting chat replaces email2014–2019
• Pimoroni's Enviro+ turns Raspberry Pi into a citizen-science air quality monitor2019
• NGINX agrees to F5's $670M buyout after open-source web server bet2002–2019
• Microverse bets a teacher-free, income-share school can train devs worldwide2019
• Lyft files for a $20–25B IPO after losing $911M in 20182016–2019
• Heptio: VMware acquires the Kubernetes startup founded by two of K8s' creators2017–2019
• Gusto raises $200M to make payroll the wedge into SMB benefits and fintech2012–2019
• Grafana Labs raises $24M to bet open source wins observability2014–2019
• CosmicJS sells YC on replacing WordPress — KFC and MLB already pay2019
• Automattic raises $300M at $3B from Salesforce Ventures to keep betting on the open web2014–2019
• Apollo raises $22M betting GraphQL's data graph becomes how apps fetch data2011–2019
• Airbnb posts a second straight EBITDA-profitable year as it prepares to go public2017–2019
• AI Dungeon 2 bets a fine-tuned GPT-2 can make infinite text adventures2019
• Trennd tops Hacker News with a free trend tool, then sells to Brian Dean in 6 months2019
• Cash-strapped science magazine Nautilus is acquired by a fan-led investor group2017-2019
• Chatwoot's open-source Intercom alternative tops HN and grows to 36.5k stars2017-2019
• Algolia raises $110M Series C as search-as-a-service passes 8,000 customers2017–2019
• TeamViewer: bootstrapped remote-access software becomes Europe's biggest 2019 tech IPO2005–2019
• Gandi: France's no-ads registrar, bootstrapped to €37M revenue, sold to Montefiore1999–2019
• Souq.com's MENA e-commerce bet pays off: Amazon buys the Dubai marketplace for $580M2005–2019
• Noon's $1B Gulf e-commerce bet: Alabbar and Saudi PIF launch against Amazon — and survive2016–2019
• Interswitch's rails bet: Nigeria's homegrown card network hits $1B as Visa buys in2002–2019
• ConvertKit bootstrapped creator email to $15M ARR on $55K of founder money2013–2019
• DoorDash raises $535M at $1.4B on a bet that delivery can be profitable2014–2018
• Volley bets smart speakers become a family gaming platform2016–2018
• Telegram banks $850M in the biggest ICO pre-sale yet to build TON2014–2018
• TablePlus bets a fast native client can end the multi-database tooling grind2017–2018
• Swarm's rogue SpaceBee launch draws an FCC rebuke that imperils its satellite IoT bet2016–2018
• Robinhood's zero-fee trading bet survives 75 rejections, reaches a $5.6B round2013–2018
• Pilot raises $15M to prove software-plus-human bookkeeping can scale2017–2018
• N26's bank-from-scratch bet: $160M from Tencent and Allianz2015–2018
• Instacart raises $200M at $4.2B to stay the neutral grocer against Amazon2017–2018
• Front raises $66M from Sequoia to replace Outlook with a team email client2014–2018
• DIRT Protocol raised $3M to bet token staking can keep open data honest2018
• CoinTracker bets automatic tracking makes crypto taxes painless2017–2018
• Checkr raises $100M to scale API background checks beyond the gig economy2014–2018
• Bird's scooter bet: from $300M valuation to a $2B ask in three months2018
• SpaceX's 2018 raise bet: $500M at a $30.5B valuation while launch demand softens2018
• Slack raised $427M at a $7.1B valuation to fund its bet against Microsoft and Facebook2013–2018
• RevenueCat hit $350K monthly volume by YC S18 Demo Day on its outsource-subscriptions bet2017–2018
• PagerDuty raised $90M at a $1.3B valuation in 2018 after passing $100M ARR2010–2018
• Magic Sandbox taught Kubernetes on real clusters; the 2018 HN launch hit 500 servers2018
• Journal raised $1.5M to search email, Slack and docs like Google searches the web2017-2018
• HoneyLove sold $500K of engineered shapewear by its YC S18 Demo Day launch2018
• GitLab's all-in-one DevOps bet: $100M at a $1.1B valuation as GitHub went to Microsoft2014–2018
• Asana raised $50M at a $1.5B valuation to own work management2018
• Airtable raised $100M at a $1.1B valuation to make spreadsheets build apps2018
• Tuft & Needle: no-VC mattress startup did $170M in sales, merged into Serta Simmons2012–2018
• Konga's Amazon-of-Nigeria bet: $108M raised, then Zinox's 2018 fire sale2012–2018
• Snap Inc. raises $3.4B in its IPO and opens 41% above the $17 offer price2017
• Flexport raises $110M at $800M pre to become a real freight company2013–2017
• Whoishiring.io relaunches as a paid business after its #42 all-time Show HN2015–2017
• Robinhood confirms $110M Series C at a $1.3B valuation, joining the unicorn club2013–2017
• Pinterest raises $150M at 2015 share price, a flat-round bet on purchase intent2010–2017
• Instacart's $400M 2017 round at $3.4B bets groceries consolidate on one delivery app2012–2017
• Houzz confirms it is raising $400M at ~$4B to push remodeling into visual commerce2009–2017
• Change.org raises $30M led by Reid Hoffman after ad model forces layoffs2007–2017
• Atrium LTS raises $10.5M from nearly 100 investors to bring software to legal work2017
• Slack takes $250M from SoftBank's fund at a $5B valuation2016–2017
• Sitebulb's two-person team launches a desktop SEO crawler that sells pre-built reports2015–2017
• Plenty raises $200M from SoftBank to take vertical indoor farms global2017
• Patreon's $60M Series C at ~$450M bets fans pay creators directly2013–2017
• Jawbone liquidates after the wearable bet fails; CEO pivots to clinical health1999–2017
• Impossible Foods raises $75M to race its plant burger into grocery stores2011–2017
• Deliveroo raises $385M at $2B+ to fix thin margins with Editions kitchens2013–2017
• Canny reaches ramen profitability after pivoting to a paid feedback SaaS2016–2017
• Angie's List's paid-membership review bet ends in a $500M sale to IAC1995–2017
• Blink's no-wiring, no-subscription camera bet ends in an Amazon acquisition2017
• Grammarly: eight bootstrapped years, profitable, then a $110M first round2009–2017
• Basecamp refused 100+ investors and stayed profitable: $25M revenue, 52 staff by 20171999–2017
• Pixelapse bet designers wanted GitHub-style version control; Dropbox acquired it in 20152011–2016
• Mesosphere's $73.5M round backed its bet on a Mesos data-center OS2013–2016
• Unity raises $181M at ~$1.5B to fund its bet that AR/VR gets built on its engine2004–2016
• Spotify took $1B of penalty-laden debt rather than a down round to fight Apple Music2016
• Sentry, the open-source crash reporter, raises a $9M Series A from NEA and Accel2012–2016
• Scale launches at YC S16 Demo Day betting developers will call an API for human labor2016
• Podcat: a one-developer 'IMDb for podcasts' that drew 401 HN points at launch2016
• Petcube's YC W16 bet on interactive pet hardware: 20,000 cameras sold, $2.5M revenue2013–2016
• Hyperloop One raises $50M led by DP World and hires Uber's ex-CFO to build tube transport2016
• Deckchair: a bootstrapped holiday SaaS whose launch post hit 134 HN points2016
• Chariot acquired by Ford Smart Mobility after betting crowdsourced commuter shuttles2014–2016
• Brendan Eich's Brave browser raises $4.5M seed for its Bitcoin micropayment bet2016
• Viv Labs sells to Samsung in 2016 after betting its AI could write its own code2012–2016
• Unity Biotechnology raises $116M with Bezos backing to build anti-aging drugs2016
• Hipmunk bought by Concur after betting search could take the agony out of travel2010–2016
• WhatsApp bet messaging would kill SMS and ran 900M users on 50 engineers2009–2015
• Pinterest pushed lifetime funding past $1B with a $367M Series G at an $11B valuation2015
• Standard Cyborg's YC W15 bet: $800 3D-printed legs vs $23,000 hand-made2014–2015
• Stack Exchange bet developer trust pays via recruitment; a16z led its $40M Series D2008–2015
• Rescue Forensics' YC W15 bet: tracking online sex ads to find victims2015
• Wheelys' bike-cafe bet: 150 carts in 20 countries by its YC-backed Wheelys 3 launch2015
• Turing Pharmaceuticals hiked Daraprim from $13.50 to $750 a tablet, igniting a firestorm2015
• Tilt raised around $30M at a $400M valuation for its mobile crowdfunding bet2013–2015
• Standard Treasury Joins Silicon Valley Bank After Its Own-Bank Bet Failed2013–2015
• Square priced its IPO at $9, halving its $6B private valuation to go public2014–2015
• Medium raised $57M to bet it could become publishing's dominant quality pipeline2015
• Livecoding.tv (YC S15) launched Twitch-style coding streams after a 40,000-user beta2015
• Jukedeck's algorithmic-music bet won Disrupt London 2015, then a 410-point HN launch2015
• Gigster's managed-app bet booked $1M in two weeks, then raised a $10M a16z Series A2014–2015
• Adafruit: dorm-room DIY electronics kits bootstrapped to $33M, no VC2005–2015
• WooCommerce: free-plugin bet powered ~30% of online stores, sold to Automattic2008–2015
• Plenty of Fish: one-man free dating site nets $10M/yr, sells for $575M2003–2015
• Atlassian bootstrapped dev tools with no sales team to $319.5M revenue and a $5.78B IPO2002–2015
• Product Hunt bet a curated invite-only community would own new-product discovery2013–2014
• Dropbox's 2014 $10B bet: consumer sync had to become an enterprise business2011–2014
• Docker bets open-source containers replace VMs; Greylock leads $15M Series B2009–2014
• Uber's record $17B round bet cheaper rides would make it the default way to move2014
• Sysadmin Casts bet bite-sized screencasts could teach what scattered docs couldn't2013-2014
• SlideRule bet sequenced learning paths could teach web dev from scratch2014
• Mattermark bet on a second seed round when Series A terms were out of reach2012-2014
• Javelin Browser bet a free mobile-first Android browser could sell Pro and VPN2014
• Rap Genius raised $40M, renamed Genius, betting annotation could scale beyond rap2009-2014
• Square's $150M GIC-led round at $6B funded its bet on independent merchants over Apple Pay2014
• RelativeWave bet designers would pay for app prototyping; Google bought it, Form free2014
• Buffer raised $3.5M the 'middle way': founder liquidity, no board seat, at $60M2014
• dotGEARS' Flappy Bird: a solo dev made $50K/day in ads, then pulled the game at its peak2013–2014
• Mojang's no-VC Minecraft bet: $2.5B Microsoft exit2009–2014
• CameraLends bets a camera-gear niche can make peer-to-peer rental work2012–2013
• ZURB gave away responsive email templates, then shipped the Ink email framework2012–2013
• Tack Mobile launched its first game Adrift free after a founder quit his job2012–2013
• Segment.io's 2013 pivot bet: one analytics API instead of another analytics product2011–2013
• Microryza (YC W13) bets the crowd will fund the science grants skip2012–2013
• Meldium (YC W13) bets teams will swap password spreadsheets for managed logins2012–2013
• Buffer's no-name founders raised ~$500k seed on traction and a public deck2011–2013
• MongoDB raises $150M at a $1.2B valuation on its document-database bet2007–2013
• Macaw raises $275,929 on Kickstarter for its design-to-code web tool2012–2013
• Fitbit raises $43M to turn fitness trackers into a mass-market business2008–2013
• Cyanogen raises $7M to turn CyanogenMod into the third mobile OS2009–2013
• Boxee sells to Samsung for ~$30M after betting on streaming hardware2008–2013
• Ansgar Grunseid's Arc bets on Linux VMs in the browser to cut server costs2013
• AnsibleWorks raises $6M to make enterprise IT automation simple2012–2013
• Shopify's 2013 bet: one $100M platform for online stores and physical retail2006–2013
• Kima15's bet: fixed $150K-for-15% terms decided in days beat accelerators for some2013
• Flutter's wave-to-control-media bet ends with Google buying the YC W12 team2012–2013
• Dropbox's 2007 Show HN bet: a background-synced folder beats online drives2007–2013
• Draw Something: OMGPOP's viral hit, sold for ~$200M, shut down 440 days later2012–2013
• Appifier bets WordPress site owners will pay for native iPhone apps2012
• Treehouse raised $4.75M while betting a 4-day week beats burnout2011–2012
• Mixpanel's $10.25M Series A bet: engagement events, not pageviews2012
• Loopt bet on location sharing before smartphones; Green Dot paid $43.4M cash2005–2012
• Hackpad's bet: realtime WYSIWYG editing would make wikis usable again2012
• Gumroad raises $7M from Kleiner Perkins to make selling anything as easy as sharing a link2012
• Double Fine's Kickstarter bet: fans would fund a Schafer adventure, no publisher2012
• Curebit bet friend referrals would beat ads; $1.2M seed backed it in 20122011–2012
• Typesafe's 2012 bet: raise $14M to commercialize open-source Scala2012
• Pair (YC W12) raises $4.2M to build a social network for exactly two people2012
• Meteor's 2012 bet: $11.2M to make a JavaScript framework its only product2012
• Lockitron open-sources Selfstarter, the app behind its own crowdfunding2012
• FundersClub's 2012 bet: online $1,000 startup investing for accredited investors2012
• BlackGirlsCode raises $21K on IndieGoGo for nationwide coding classes for girls of color2011–2012
• Ark (YC W12) bets a neutral people-search layer can beat Google and Facebook2012
• Qualtrics: profitable and bootstrapped for a decade, then a $70M first round2002–2012
• Zynga files for a $1B IPO after its free-games, virtual-goods bet hits scale2011
• Viximo's core-group bet: co-founder, prototype and $5M in four weeks2007–2011
• Google acquires five-month-old TalkBin for its mobile-local feedback bet2010–2011
• MemSQL raises $2.1M to bet in-memory SQL can replace disk databases2011
• Mailgun bets developers rent email plumbing; $1.1M from SV Angel and Milner2010–2011
• Marco Arment kills Instapaper Free after paid-only tests lift sales2008–2011
• GitHacking, born at Startup Weekend, bets paid matching fixes open source2011
• Facebook raises $500M at a $50B valuation, betting it can delay its IPO2010–2011
• Wufoo, the bootstrapped form builder that raised $118K, exits to SurveyMonkey for $35M2006–2011
• Push Pop Press' interactive-book bet ends in Facebook's 2011 acquisition2010–2011
• Punchd's phone-loyalty-card bet ends in Google's July 2011 acquisition2010–2011
• PostRank's social-signal bet ends in Google's June 2011 acquisition2011
• Nest Labs' thermostat bet: turn the box that runs home energy into a beloved object2011
• MixRank (YC S11) raises $1.5M to sell small advertisers a spy tool for AdSense2011
• GroupMe's SMS group-messaging bet ends in Skype's August 2011 acquisition2010–2011
• RethinkDB raises $1.2M seed to bet SSDs on a ground-up MySQL engine2009–2010
• Keynotopia launched a profitable MVP in 3 hours — first sale in 10 minutes2010
• inDinero bets small businesses want a Mint of their own; Jessica Mah, 20, raises $1M+ seed2010
• GitHub bet developers would pay for private repos — bootstrapped, profitable by 20102007–2010
• BaseShield launches a sandboxed Windows app store for third-party software2008