# Nate Kontny

> Nate Kontny is a Chicago-based serial founder, engineer, and writer who went from chemical engineering at UIUC to co-founding two Y Combinator companies (Inkling W06, Cityposh S11), running Highrise as CEO for Jason Fried, writing prolifically across Medium, HuffPost, and Fast Company, and building a suite of solo products - most recently AlliHat, a Safari extension embedding Claude AI directly in the browser. Currently Staff Engineer at Fivetran (post-Census acquisition), he is known for his radical transparency about failure, his 250-words-a-day writing discipline, and a philosophy that shipping imperfect work beats endless polishing.

- **Role:** Staff Engineer at Fivetran
- **Organizations:** Fivetran, AlliHat, Draft (draftin.com), Census (acquired by Fivetran), Highrise (former CEO), Inkling (YC W06), Cityposh (YC S11), Rockstar Coders
- **From:** Chicago, Illinois, USA
- **Nationality:** American
- **Education:** BS Chemical Engineering, University of Illinois Urbana-Champaign
- **Known for:** Two-time Y Combinator founder (Inkling W06, Cityposh/Draft S11), CEO of Highrise (2014-2018), growing it to millions in annual profit with a 7-person team, Built Draft solo - a writing tool used by tens of thousands of customers

## Career timeline

- **1999** — Graduated UIUC with Chemical Engineering degree; taught himself programming after an injury during a uranium plant internship
- **1999-2005** — Worked at Accenture (then Andersen Consulting); taught himself Java using office internet after hours
- **2005** — Co-founded Inkling, accepted into Y Combinator Winter 2006 (second-ever YC batch)
- **2011** — Co-founded Cityposh, accepted into Y Combinator Summer 2011
- **2011** — Demo Day disaster with Cityposh - even with Ashton Kutcher in the room, nobody cared
- **2012** — Pivoted Cityposh into Draft (draftin.com), a version-controlled writing and collaboration tool
- **2012** — Engineered for the Obama re-election campaign
- **2014** — Jason Fried tapped him as CEO of Highrise after Basecamp spun it off
- **2014-2018** — CEO of Highrise; ran 7-person team generating millions in annual profit; wife Lynette joined as COO
- **2018** — Left Highrise; team departed March 30, 2018; Basecamp took operations back
- **2018-2020** — CTO and CMO at Rockstar Coders
- **2020** — Joined Census as Founding Engineer (reverse-ETL / composable CDP data platform)
- **2020-2025** — Staff Software Engineer at Census
- **2025** — Census acquired by Fivetran (May 2025); continued as Staff Engineer at Fivetran
- **2026** — Launched AlliHat - Safari sidebar extension embedding Claude AI in the browser (February 5, 2026)

## Achievements

- Two-time Y Combinator founder (Inkling W06, Cityposh/Draft S11)
- CEO of Highrise (2014-2018), growing it to millions in annual profit with a 7-person team
- Built Draft solo - a writing tool used by tens of thousands of customers
- Founding Engineer at Census, acquired by Fivetran in 2025
- Open-source Ruby/Rails library multi_fetch_fragments has 538+ GitHub stars
- Published in HuffPost, Fast Company, Quartz, Signal v. Noise
- 22,000+ Medium followers
- Launched AlliHat in 2026 - a Safari extension integrating Claude AI
- Engineered for the Obama re-election campaign in 2012
- Arctic Code Vault Contributor on GitHub
- Maintained 250 words/day writing discipline for 8+ years

## Latest updates

- **2026-02** — Launched AlliHat, a $29.99/year Safari sidebar extension embedding Claude AI in the browser with agent mode, page awareness, and local privacy
- **2026-01** — Active blogging: 'Make more cheap garbage' (Jan 5), 'It just takes a minute' (Jan 15), 'Can you make Claude cry?' (Jan 27)
- **2025-05** — Census acquired by Fivetran; Nate continued as Staff Engineer at Fivetran
- **2025-12** — Difficult personal period - his father's senior community building closed; wrote candidly about running out of steam on personal projects

## Links

- Website: https://ninjasandrobots.com/
- LinkedIn: https://www.linkedin.com/in/nathankontny/
- Twitter/X: https://x.com/natekontny
- GitHub: https://github.com/n8
- YouTube: https://www.youtube.com/nathankontny
- Instagram: https://www.instagram.com/imn8/
- Facebook: https://www.facebook.com/nathankontnytv

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Profile page: https://yespress.io/nate-kontny
Published by YesPress — https://yespress.io
Last updated: 2026-04-28