If you've ever wondered how angel investors actually think — what makes them write a cheque, what makes them walk away, and what founders get wrong when courting them, our latest CDH Lunch & Learn had you covered.
This session was built for founders who are angel-curious: not yet raising, but keen to understand the earliest layer of startup capital before they get there. CDH General Manager Alan Tsen stepped in to share his own angel investing playbook built over 8 years and 11+ personal investments, predominantly in early-stage fintech.
Before CDH, Alan headed up IAG's accelerator program, led revenue strategy at a global fintech startup, was founding GM at Stone & Chalk Melbourne, founded a company and started his career in tax. He's sat on both sides of the cap table as a founder and as the person writing the cheque.It showed in how practically he broke things down.
Here are the biggest takeaways for founders thinking about bringing angels onto their register.
1. Angels fill rounds — they rarely lead them
Outside of syndicates, angels typically don't set the terms of a raise. Think of your round like a jar: a lead investor (usually a fund) provides the "big rocks," and angels are the sand that fills the gaps. In Australia, most angels write cheques in the $5K–$50K range, and they typically prefer that the round's terms are set.
2. They're backing people and insight, not traction
At pre-seed and seed, there usually isn't meaningful traction to point to anyway. Alan's most recent cheque went to a founder and a concept — no product yet. Angels who invest this early are pricing in belief in the person, not de-risked metrics.
3. Understand why they're investing
Motivations vary. Some want the asymmetric upside of the "next Canva," others want proximity to sharp operators and a front-row seat to how they build, and some are quietly building a track record toward launching their own fund one day. Knowing which type you're talking should shape how you pitch them.
4. There are two broad angel archetypes
- Capital angels write the cheque and step back. That's not a bad thing — sometimes all you need is fast, low-friction money.
- Operator angels have been in the trenches and can genuinely accelerate you, unblocking a go-to-market problem, opening a warm intro to a fund, or lending credibility that helps your next raise. Don't assume every angel is this type, and don't be disappointed when they're not.
5. Ask direct questions before you take the money
Alan's suggested checklist for any prospective angel:
- What's your average ticket size?
- What stage do you usually invest at?
- What do you actually invest in?
- How do you typically help founders?
- When should I come back to you?
The answers tell you whether they're a fit and whether they're going to be useful or just another name to manage on your cap table.
6. Good angels leave a paper trail
Want to find angels who actually operate in your niche? Skip the generic spray-and-pray lists. Look for people who write, podcast, or blog about the space, sharing how they think is often a strong signal of both operator credibility and a willingness to be genuinely helpful.
7. Cold outreach works, if it's thoughtful
Alan is a fan of cold DMs and cold emails, provided they're specific and well-researched. A short, direct note explaining what you're building and exactly what you want from the conversation goes a long way. Treat it like a sales outreach: know why you want them, specifically.
8. Be deliberate about who joins your cap table
Bringing on angels is a rare chance to assemble a bench of advisors you could never otherwise afford to hire. But more angels means more admin, more small cheques to chase, and occasionally a "meddler" who gives strategic advice without understanding the day-to-day reality of an early-stage company. Screen for fit, not just for money.
Want to connect with Alan Tsen directly? Find him on LinkedIn.
