What Investors Look for in Their Startup Picks

What Investors Look for in Their Startup Picks | BOLD

Investors don’t decide to invest in one go. They jump from lily pad to lily pad — deck, coffee, due diligence, terms — and each pad asks a different question. The panel walks through what they’re actually looking for at each stage, why the data room is a pile of clues rather than answers, and the one question Rachael asks every founder before going further.

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Key Takeaways

•Evaluation is a series of lily pads. The question shifts at each stage — don’t assume a “no” at the deck stage means a “no” forever.
•Read the investor’s website before you pitch. VC mandates are a Venn diagram of stage, sector, geography, and cheque size.
•Data rooms are clues, not answers. Use the documents you already run the company on, not custom artefacts created for diligence.
•Financial models are a proxy for ambition, not a forecast. “More fiction is written in Excel than is written in words.”
•The question that reveals obsession: “You could be doing anything in the world. Why this?”

More fiction is written in Excel than is written in words. I use the model as a proxy for how this founder thinks about the growth trajectory.

— Rachael Neumann, Founding Partner, Flying Fox Ventures

Featured Investors

Rachael Neumann – Founding Partner at Flying Fox Ventures. Flying Fox is one of Australia’s most active early-stage venture capital firms. Former Amazon executive with deep operator experience. Rachael backs founders at eye-wateringly early stages, invests off-balance sheet to build conviction, and champions Victoria’s tight-knit startup ecosystem. Portfolio includes 70+ companies.

Justine Carzino – Investment Principal at OneVentures. Justine focuses on Series A to Series B investments and helps companies build go-to-market strategies for international expansion. She brings a sharp lens on founder-investor alignment and long-term partnership over the 10-year fund lifecycle. OneVentures is one of Australia’s leading venture capital and growth equity firms.

Timothy Hui – Partner at Mandalay Venture Partners. Mandalay is a thematically focused fund investing in agri-food technology across Australia and Southeast Asia. Engineering background with a first-principles approach to startup evaluation. Timothy takes board seats selectively and brings deep commercial networks and governance expertise to early-stage portfolio companies.

Rohan Workman – Co-Founder + CEO at Skalata Ventures. Skalata invests at the pre-seed and seed stage across a portfolio of 80+ companies. Former accelerator leader with a practical, founder-first approach to early-stage support. Rohan is known for direct advice, strong co-investor relationships, and building the infrastructure that helps founders move from chaos to structure.

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