ITR #004: The Art of Investment: More Gut Feel, Less Checklist.

Welcome back to Into the Ring!

Thank you for your feedback on the most recent edition of ITR, on how to write great outreach emails. Happy to hear my advice resonated. As always, let me know if you have feedback or any suggestions for future editions - I’m all ears.

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I want to take a quick pause to congratulate my client Coding Giants, who have just announced a $9M raise, in a round led by True Global Ventures (TGV). Coding Giants are doing amazing work in hybrid coding education for students aged 6–19, helping 200,000 students across 12 countries. Super stoked for them! 🚀

The year may be winding down, but the race for investment only gets hotter. 2025 could be a key growth year for founders sending out the right signals. 🔥

This week, I’ve got some tried-and-tested guidance to help founders understand what signals VCs are really looking for in early-stage companies, and outline four mission-critical areas for founders to focus on.

There is No ‘Ultimate Investor Checklist’ 📣

A quick scroll through Linkedin would have founders believe that there’s an ultimate ticklist when it comes to securing VC investment. Check the boxes, ace the scoring and you’re as good as funded. Right? ✅

If only! ❌

There’s a lot more gut feeling and instinct involved than you might expect. In fact, the most exciting opportunities for investors I know often come in the guise of powerful stories and inspirational people. When you’re at the Pre-Seed, Seed or even Series A stages, it’s not about perfect data - it’s about building conviction.

Yes, great results matter, but early on, investors understand that your data will be incomplete, your product is still evolving, and your roadmap uncertain. They’re looking for something that’s much more difficult to quantify - excitement, possibility, and uniqueness. 

The most compelling signals center around four pillars: team, traction, market, and storytelling. Here’s how to layer these elements to paint an enticing picture that transforms hesitation into confidence.👇

1. Team 👥

The capabilities and experience of your founding team might be the most important signal of all. Many investors say they invest in founders first at the early stages.

Convince investors of your exceptional team attributes by highlighting your:

• Founder-market fit: Show why you as a founder are uniquely positioned to solve this problem, and how your experience and insights align with your mission. This is no time to be shy - push your relevant background and achievements.

• Diverse backgrounds: A team with diverse strengths - technical expertise paired with go-to-market capabilities, for example - signals balance, adaptability and the potential for rapid growth.

• Resilience track record: Maybe the most pertinent skill going for today’s founders. It’s a volatile world out there - share examples of how the team has tackled tough challenges or thrived under pressure.

2. Traction 🚀

Traction is the most tangible signal of progress and validation, and a key component of what investors are looking for.

Demonstrate growing traction by:

• Showing momentum: If you can demonstrate that you are building early momentum in terms of customer growth, revenue milestones, and engagement, you’ll be well placed to impress.

• Framing milestones strategically: Explain how your early wins validate your direction and lead the way for success.

• Connecting to the future: Join the dots for investors and lay out clear milestones to show how the current round of funding will accelerate your growth journey.

3. Market

No matter how inspiring a founder’s vision, even the best product will fail in the wrong market. Investors prioritize startups that address large, growing markets ripe for disruption.

Prove that you’ve done the important strategic work by highlighting:

• The defined opportunity: A classic signal for investors is an articulation of your Total Addressable Market (TAM). Most investors won’t consider a TAM under $10bn. Demonstrate the true size of the opportunity and why your space has room for significant growth - the bigger, the better.

• Emphasize timeliness: Introduce a sense of urgency. Why now? Highlight shifts in technology, consumer behavior, or regulations that make this moment critical. Investors love to be a part of meaningful transformation.

• Narrow your focus: A winnable niche demonstrates focus and strategic thinking while building a foundation for long-term success.

4. Storytelling 📖

Storytelling isn’t just an afterthought—it’s what ties everything together. A great story builds emotional connection and inspires conviction.

Draw investors in with a compelling story by highlighting: 

• An emotional hook: Share the ‘why’ behind your startup, and don’t be afraid to show passion. This signals to investors that you’re committed for the long haul, not just riding a trend.

• A clear, concise message. You’d be amazed how many founders struggle with this. Your message should be clean, clear and easy to grasp, and threaded consistently throughout your materials, including pitch deck, Q&A, data room and more.

• Passion combined with clarity. A strong story balances emotional resonance with data and strategy, making your opportunity both intriguing and credible.

The Big Picture: 20/20 Vision 🔮

As a founder seeking early-stage funding, your job isn’t to check every box, but to piece together a mosaic of important signals that excite investors. Team, traction, market, and storytelling all combine to instill confidence in your ability to deliver.

 Signal these effectively, and you’ll inspire investors to bet on your vision.

👉 Need help making sure you’re sending out the right signals? I can help.

Every other week, I’ll be reaching out to my network to get their take on important questions on every aspect of fundraising. Got a question you’d like me to ask? Let me know. This week, a look at useful tools.

Q: What types of tools or services do you find invaluable?

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