What actually kills startups? Sometimes it’s not product… it’s timing.

In this episode, I’m joined by Alan Jones: angel investor, startup mentor, ex-founder, and co-manager at M8 Ventures (backing early-stage tech across Australia & New Zealand). Alan’s also the host of Pick My Brain, where founders pitch live and get the kind of feedback that’s equal parts practical and slightly brutal.

We talk about:

• why timing is the variable no one can control (and why it quietly decides so many outcomes)
• Alan’s “life is a side-scrolling shooter” metaphor (and why it’s weirdly accurate for careers + startups)
• what he looks for in early-stage founders — and the red flags that make him pause
• why he says he likes to invest in time (not just money), and how relationship-building scales… until it doesn’t
• why diverse teams are often more resilient than “perfect” monoculture founder duos
• the balance founders need: what to do carefully vs what can be tested fast and messy
• a classic story of moving fast… and sending the wrong cover letters (painful, hilarious, and a real lesson)

If you’re building in a world where AI is speeding everything up — this one will make you rethink what you can control, what you can’t, and how to keep moving anyway.

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