Episode Summary

Some investor phrases sound helpful. Others feel like a riddle. In this episode, Cheryl and Maxine crack open the language investors use when talking to founders, and translate what’s actually being said behind phrases like “not a fit,” “too early,” or “let’s have one more meeting.”

They walk through the subtle (and not-so-subtle) cues that signal a pass, explain what “conviction” actually means in VC-speak, and share tactics founders can use to get clearer answers during fundraising. You’ll also hear the behind-the-scenes realities of ghosting, deal timelines, internal partner politics, and why “we’d love to stay close” usually means… they won’t.

Plus: a rapid-fire rundown of the weirdest (and most cringe) investor slang, from “due dilly” to “foundies.”

Whether you’re raising your first round or managing investor relationships post-close, this episode helps you spot the signals, ask better questions, and avoid wasting time.

Time Stamps

01:45 – “Not a fit”: Why investors love this vague phrase

03:40 – What they mean when they say “you’re too early”

08:30 – “You’re too late”, how stage mismatches work both ways

15:30 – “We’ll circle back” and other signs of a slow no

17:10 – How long does VC diligence really take?

19:15 – Why June 30 is a terrible time to raise

24:10 – Optionality: The excuse behind “we love what you’re doing”

28:00 – “Let the lawyers sort it out”: A red flag or not?

30:15 – The weirdest investor slang (please don’t say “due dilly”)

33:30 – Term sheet vs. side letters: what’s actually worth negotiating

36:00 – Understanding info rights vs. investor updates

38:50 – How to share bad news without burning relationships

45:20 – The shifting goalposts of traction and growth metrics

47:00 – Spotting investor doubts through team questions

48:10 – Final thoughts for both founders and investors

Resources

😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy

🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/

💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/

Sponsors:First Cheque is supported by our wonderful sponsors:

Aussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence.

https://www.aussieangels.com/

Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.

https://dayone.fm/galah

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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