General Tech & Marketplaces
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5.1 Airbnb – Consumer Marketplace
Marketplace for short‑term stays and experiences that proved demand with scrappy hacks before institutional capital. Delayed heavy equity until PMF, surpassing 100k nights/month pre‑Series A and then raising a $112M Series B in 2011.
Capital stacking approach: Bootstrapped → Accelerator → Angel SAFE → Series A
Product‑Market‑Fit Phase
Bootstrapped via credit cards + novelty cereal (~$30k) to prove demand.
Y Combinator $20k / 7% (2009) to rebuild the site and run first bookings.
Angel SAFE $600k (Sequoia) to hire engineers and launch NYC.
Series A $7.2M (2010) once monthly nights booked >100k → PMF.
Scale‑Up Phase
Series B $112M (2011); Series C/D $650M (2013–14); 2020 debt + equity → IPO 2020.
References: Company site · S‑1 (SEC) · Sequoia seed story · Silver Lake financing
5.2 GitHub – Developer Collaboration
Bootstrapped code hosting that hit break‑even by 2010 and later exceeded ~$200M ARR by 2017; took one $100M round to scale enterprise before a $7.5B acquisition (2018).
Capital stacking approach: Bootstrapped → Early product revenue → Series A
Product‑Market‑Fit Phase
Bootstrapped (2007) on ~$10k personal funds.
Paid accounts (2008) → break‑even by 2010.
Scale‑Up Phase
Series A $100M (2012) for enterprise; MSFT acquisition 2018.
References: Company · a16z note · Microsoft press · DOJ closing statement
5.3 Mailchimp – SMB Email Marketing
Self‑serve marketing platform that scaled freemium + bank lines to ~$700M revenue by 2019 with zero VC, then sold to Intuit for ~$12B (2021).
Capital stacking approach: Bootstrapped → Early product revenue → Bank LOC
Product‑Market‑Fit Phase
Self‑funded pivot (2001–07) from agency; freemium in 2009.
Scale‑Up Phase
Cash flow + bank lines → 14M users; Intuit acquisition 2021.
References: Company · Intuit press · Founder interview · SEC 8‑K
5.4 ConvertKit – Creator Email Platform
Founder‑funded email + commerce stack that grew to mid–eight‑figure ARR on a lean team, financing working capital via annual pre‑pays and revenue‑based advances.
Capital stacking approach: Bootstrapped → Early product revenue → Revenue‑based financing
Product‑Market‑Fit Phase
Founder‑funded MVP (2013–14); price‑led niche focus.
Scale‑Up Phase
Profit‑funded growth; occasional revenue‑based lines; public metrics.
References: Company · Open metrics · Founder blog
5.5 Basecamp (37signals) – Project Management
Client‑funded v1 that remained profitable for ~20 years, prioritizing dividends and calm growth over blitzscaling.
Capital stacking approach: Customer capital → Bootstrapped growth
Product‑Market‑Fit Phase
Agency‑funded build (2003–04); opinionated SMB wedge.
Scale‑Up Phase
No VC; selective product expansion (HEY), long‑term dividends.
References: Company · 37signals essays · REWORK
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