Rowan Simpson
About Rowan Simpson
Rowan Simpson trained as a software engineer and holds a Bachelor of Science in Computer Science from Victoria University of Wellington. He was part of the founding team at Trade Me, which he says grew from nothing to a NZ$750m exit in about seven years. A podcast listing describes him as employee number 3.
After Trade Me he became an early investor in Xero. He was also part of Xero's early executive team around its 2007 IPO and stayed about a year afterward. PitchBook lists him as founder of Electric Fence and chairman of Hoku Group. He is based in Nelson, New Zealand, and writes occasionally for The Spinoff on technology and government policy.
In a Q&A with AirTree, Simpson said he had invested about $8m in 29 ventures since Trade Me. He said 16 were still active at that time. He has often been the first external investor or part of the first round, and sometimes had a role in the venture as it started.
PitchBook credits him as a pre-IPO investor in Xero (2007), one of the initial investors in Vend (2010) and the first investor in Timely (2013). Other investments listed there include Atomic.io (seed, 2014), Melodics (seed, 2015), Parkable (2021) and Huckleberry (2025).
Lounge's deals desk lists Sterling's A$3.15M seed round (August 2026) as his AI round. PitchBook categorises Sterling as financial software and also dates his investment to August 2026. Tracxn describes Thematic, another portfolio company, as an AI-based customer feedback analytics platform. PitchBook dates his Thematic investment to 2017. Beyond these, we found no public statement from him about an AI-specific investment thesis.
Public databases show early-stage software investments, including seed rounds, in business and productivity software, financial software and applications. Tracxn lists New Zealand and the United States as his main investment locations. Simpson has said the way he invested in the past may no longer apply. He cited the stronger support now available to founders and the wider range of ways to raise money. He has not published a check size, so none is given here.
- Xero: cloud accounting software; pre-IPO investor in 2007.
- Vend: retail point-of-sale software; one of the initial investors in 2010.
- Timely: scheduling software; first investor in 2013.
- Atomic.io: design and prototyping software; seed investor in 2014.
- Melodics: music learning application; seed investor in 2015.
- Thematic: AI-based customer feedback analytics; PitchBook dates his investment to 2017.
- Parkable: business software; investment listed in 2021.
- Huckleberry: business software; seed investment listed in October 2025.
- Sterling: financial software; A$3.15M seed round in August 2026.
- pitchbook.com/profiles/investor/222661-99
- airtree.vc/open-source-vc/the-halo-effect-rowan-simpson
- tracxn.com/d/people/rowan-simpson/__7cNI-wsuR4XPfRI6HT2NY4cpTd06ocBt_n
- thespinoff.co.nz/authors/rowan-simpson
- crunchbase.com/person/rowan-simpson
- linkedin.com/posts/betweentwobeerspodcast_rowan-simpson-was-employee-3
Investing activity
Rowan Simpson appears in 1 AI deal tracked by the Lounge deals desk. The rounds are mostly Seed, with a median round size of $2M. The most recent is Sterling (Seed, A$3.15M, Aug 2026).
Rowan Simpson most often invests alongside Blackbird and Eliot Crowther, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Rowan Simpson
Who is Rowan Simpson?
Rowan Simpson is a New Zealand software engineer and angel investor. He was part of the founding team at Trade Me and an early investor in Xero. He is based in Nelson.
What AI startups has Rowan Simpson invested in?
The Lounge deals desk lists Sterling's A$3.15M seed round from August 2026. Tracxn describes his portfolio company Thematic as an AI-based customer feedback analytics platform.
What is Rowan Simpson's check size?
He has not published a check size, so we do not list one. Founders should ask him directly.
What stage does Rowan Simpson invest in?
His listed deals are early-stage, including seed rounds in Atomic.io, Melodics and Sterling. He says he has often been the first external investor or in the first round.
Which companies has Rowan Simpson backed?
They include Xero, Vend, Timely, Atomic.io, Melodics, Thematic, Parkable, Huckleberry and Sterling. Years vary by source, and the Trade Me and Xero history comes from his own account.
Where is Rowan Simpson based and where does he invest?
He is based in Nelson, New Zealand. Tracxn lists his top investment locations as New Zealand and the United States.
Is Rowan Simpson an angel investor?
Yes. Rowan Simpson invests personally as an angel.
What AI companies has Rowan Simpson invested in?
Rowan Simpson's AI investments include Sterling. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
What stage does Rowan Simpson invest at?
In the rounds tracked on Lounge, Rowan Simpson has invested at Seed, with a median round of $2M.
Who does Rowan Simpson co-invest with?
Rowan Simpson's most frequent co-investors on Lounge are Blackbird (1 deal) and Eliot Crowther (1 deal).