Mastering Early-Stage Investing: From Checklists to Decision Diaries

Mastering Early-Stage Investing: From Checklists to Decision Diaries

Mastering Early-Stage Investing: From Checklists to Decision Diaries

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Join Cheryl and Maxine on an insightful journey into early-stage investing in this episode of First Cheque. The discussion covers the transition from basic checklists to more sophisticated decision diaries, emphasizing structured evaluation and the importance of capturing and analysing decision-making processes over time. Key topics include understanding founder commitment, market size evaluation, and the balance between intuition and quantitative analysis. The episode offers practical advice on refining investment strategies through critical thinking, timely decision-making, and mitigating biases. Additionally, it explores the qualitative nature of early-stage investments and the value of leveraging instincts effectively. Tune in to transform your investment decisions with proven frameworks and mental models.

Chapters

00:00 Welcome to First Cheque: Your Guide to Early Stage Investing

00:22 Diving into Decision Making and Mental Models

02:05 From Checklists to Decision Diaries

07:20 Evaluating Founders and Market Size

16:28 The Importance of Timing in Investment Decisions

20:13 Understanding Mid to Late Stage Investing

20:56 The Role of Intuition and Quantitative Measures

22:38 Challenges of Data-Driven Investment Matching

23:17 Personal Experience with Investment Matching

25:49 The Potential and Limitations of AI in Investing

28:35 Decision Diaries: A Tool for Better Investment Choices

35:03 Key Questions for Investment Decisions

37:14 Reflections on Decision Making and Instincts

37:38 Conclusion and Call for Feedback

Resources

Maxine’s Decision Diary Template

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Day One® exists to help founders and startup operators make better business decisions more often

Subscribe for helpful content from other successful founders, operators and investors

Join 755 other founders & investors receiving our emails. They're cool, are you? :)

* Regrettably, mel@canva.com is not on our list… yet.

Day One® is a registered trademark of W2D1 Media Pty Ltd. All rights reserved. © 2026 W2D1 Media Pty Ltd.