Rayn Ong is the angel investor a startling number of Australian founders trace a key introduction back to — Cheryl Mack and Maxine Minter call him the "all-seeing eye" who somehow sees every deal in the ecosystem. On this First Cheque he breaks down how he actually built that, and how he backs the breakouts.
It starts at ground zero. Rayn's first money out of the trust account was Blackbird Fund 1, in 2014 — he was one of the last five in before the final close, and paid three capital calls in one go. The same year he backed Instaclustr (later acquired for US$500M). Eight investments in his first year.
The network edge wasn't luck. In 2014 the ecosystem was barren, so he simply met everyone — Sydney Angels taught him to run deals and syndicates, and he'd reach out to co-investors on every term sheet. His real entry ticket: as a nine-year software engineer he did the technical due diligence the finance-and-legal crowd couldn't — interviewing CTOs, mapping competitors — so they looped him into the best deals. Do that useful thing in one niche, repeatedly, and the network compounds and sources deals for you.
That's also how he invests across wildly different industries — microchip maker Morse Micro, alternative protein, even literal ginger — by trusting domain experts and asking "what if this works?" rather than "what if I lose?" The common thread, in his words, is anything that grows.
The real money is in the breakouts. Rayn writes small first cheques to learn, then goes heavy on the one obvious winner per cohort — Eucalyptus hit US$100M revenue in four years; the crypto game Stepn made US$20M profit in a single quarter. His 25k becomes 250k. Counterintuitive to public-market investors: he buys more when the price has tripled, because the context has changed.
He's also built a "plug and play" proposition for founders. They raise once a year; he raises every month and knows the active angels and funds for each round — so he offers a low-friction path to the next raise, doing 10–40 reps a year. And he de-risks new bets with the portfolio he already has: a company whose customers or investors are his other companies. Evaluate the system, not the deal.
Inside the Archangel Fund, his gut-feel, zero-to-one "YOLO" allocation became the thing LPs (Maxine among them) most wanted in. He's the early-stage instinct guy; partner Ben Armstrong runs the later-stage follow-ons. The cojones moment: personally bridging a whole round when almost nobody believed it would work — and the LPs who passed on his 2018 fund coming back for the 2022 one, one of them screenshotting his old pitch deck to mark every "I told you so."
**Rayn Ong** is an angel investor and connector across the Australian startup ecosystem, investing through Archangel.
**Links**
- Rayn Ong on LinkedIn: https://www.linkedin.com/in/raynong
- Archangel Ventures: https://www.archangel.vc
- First Cheque: https://dayone.fm/first-cheque
- Cheryl Mack on LinkedIn: https://www.linkedin.com/in/cherylmack
- Maxine Minter on LinkedIn: https://www.linkedin.com/in/maxineminter
Thanks for listening to First Cheque.
First Cheque is brought to you by the Day One Network. (Sponsor read — confirm the current sponsor copy from the most recent episode before publishing.)
Episode Summary
Angel investor Rayn Ong joins Cheryl Mack and Maxine Minter for a masterclass in early-stage investing — how he built a network that filters the best deals, why he backs "anything that grows," how he goes heavy on the one breakout per cohort, the "plug and play" model he offers founders, and how he de-risks new bets with the portfolio he already has.
Time Stamps
00:00 - Cold open
02:04 - Why Rayn was Maxine's first call when she started angel investing
04:30 - His first cheque: Blackbird Fund 1, 2014
06:55 - Building a network that filters the best deals
10:04 - Compounding for early-stage investors
11:54 - Investing across every industry — and "anything that grows"
20:05 - Long on ginger: a 29% yield
24:35 - Backing the one breakout per cohort
27:14 - The "plug and play" fundraiser model
34:01 - Portfolio synergy: de-risking with your own companies
39:29 - The YOLO portfolio and the 2018 fund he couldn't raise
About the host
First Cheque is hosted by Cheryl Mack and Maxine Minter — two angel investors talking to the people building and backing Australia's startup ecosystem.
About Day One Network
Day One is a podcast network for founders, operators and investors. Find more shows at https://dayone.fm.
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