This advice is essential for CEOs and entrepreneurs preparing to raise $1M or more. You can leverage these proven strategies and resources to strengthen your approach and secure investor relationships that last.
Building Relationships That Lead to Investment
At the core of successful fundraising is relationship-building. Investors don’t just hand out $25,000 checks to strangers after one meeting. It typically takes at least 3 meetings, if not 3 years, to secure trust. Start building relationships early, even if you’re not actively fundraising today. Here’s a key principle:
- 5×7 Rule: Have 5 interactions within the first 7 weeks of meeting someone to establish a lifelong connection. This could be a coffee chat, a shared resource, or a quick check-in.
Relationships with investors are based on trust. Here’s how to build it:
- Warm introductions from trusted friends, colleagues, or entrepreneurs they’ve invested in are golden.
- Connect the dots: Keep investors updated on your progress—did you do what you said you were going to do?

Nurture Trust by Asking for Advice
As a CEO, you know that trust is built over time. Here’s one key method to do that:
- Ask for advice, get money twice. Investors appreciate when you implement their feedback and report back on the results. It shows you’re coachable and serious about your business.
- Connect the dots: Share what you plan to do in the next 1, 3, 6, and 12 months. Keep investors updated on progress.
Here’s a personal story from Mike Malloy:
A friend shared a helpful Google Sheet with him, which he passed along to 50 other people, creating a ripple effect of value and trust. Sharing valuable resources can strengthen relationships effortlessly.
Leverage Social Proof and Momentum
Another powerful strategy for CEOs and entrepreneurs is to leverage social proof:
- When an investor introduces you to someone, follow up with both people to close the loop. For example, if Danielle introduces you to Sarah, send Danielle a thank-you email and keep her updated on how the meeting went. This builds goodwill and keeps you top of mind.
- Use ricochet introductions: When someone like Ted Leonsis suggests you reach out to Jeff Bezos, ask permission to use their name in the introduction. This makes the introduction easier and faster, leveraging the social proof of that connection.
Communicate with Confidence
Effective communication is key to securing investor trust. Here are some principles to guide you:
- Make the math easy: Explain your financials in a way a 3rd grader could understand to make investors feel confident in your numbers.
- Do what you say you’ll do: Following through on commitments builds trust. Use a buffer when setting expectations to over-deliver.
- Ask, “Who do you know that I should know?” to expand your network further.
- What would you do if you were me?: A powerful question to gain valuable perspective.
Maximize Investor Engagement
Investors appreciate regular communication and transparency. Here are some key practices:
Send monthly updates: Use Paperstreet.vc to send company updates to everyone.
Turn a ‘no’ into feedback: When an investor passes, ask for feedback on why they didn’t invest. It shows your willingness to improve.
- Example: “I never like to let a ‘no’ go to waste. Is there anything you can share about why the group passed? I’m always looking to improve.”
Fast no > slow maybe: It’s better to get a quick rejection than waste time on a slow maybe. Focus on moving the conversation forward.
Coachable spirit: When investors ask questions, smile and nod. Acknowledge their question with a phrase like:
“That’s a great question. I appreciate you asking.” This gives you time to think and keeps the conversation positive.
Use Momentum to Your Advantage
Leverage FOMO: Mention other investors you’re meeting with to create a sense of urgency and importance.
Example: “We had a great meeting with [Investor X], and we’re talking to [Angel Group Y]. We’d love to connect with you before the next meeting.”Accept payments in multiple ways: Be flexible with how investors can pay—bank transfers, checks, or even Venmo. The easier it is, the better.
You don’t need one close date: Be open to receiving investments at different times rather than waiting for a single close.
Mastering Your Pitch and Storytelling
Your pitch should be simple and engaging. Here’s a basic framework:
Do you know how…?: Start by identifying the problem.
What we do is…: Present your solution and unique selling proposition.
Call to value > call to action: Focus on delivering value first to capture interest.
Cover the 7 key areas:
- Problem
- Solution
- Target profile
- Trigger: “How do you do that?”
- Objections
- Testimonials
- Risk reversal & uniqueness
Always have an ask: Don’t leave a meeting without asking for something specific.
Appendix slides FTW: Have additional slides ready in your pitch deck. If an investor asks a detailed question, flip to the appendix. It shows you’re prepared and thoughtful.
Applying Maslow’s Hierarchy to Investors
At the base of Maslow’s investor pyramid is transactional alignment. Investors need to see that the deal makes sense and that there’s potential to make money.
The middle is relationship alignment—would you want to have dinner with this investor? If not, don’t take the deal. The relationship will likely last 5-10 years.
At the top is pride of ownership. What will the investor brag about? How does this investment align with their personal values and legacy?

Fundraising Resources for CEOs and Entrepreneurs
Use these resources to improve your fundraising strategy:
- Share your pitch deck with 300+ investors in Malloy’s Monthly Deal Flow
- Investor CRM Template
- Due Diligence Preparation Guide
- M&A Due Diligence Checklist
- Cooley Go document generator
- Pitch Deck Outline Company Questionnaire
- VC Sheet Investor Database
- Gritt.io Investor Database
- VC Terminology: Hustle Fund’s Top 100 Terms
- VC Platform
- Startup Internship Seminar
- Presentations
- Networking
- 5/25/150: The Secret of the Best Networker I Ever Met
- How to Pitch Slides
- How to Pitch Video
- Grant Writing
Want Mike Malloy to Help You with Fundraising, Strategy, & Sales?
If you’re ready to level up your fundraising efforts and secure investor relationships, email Mike Malloy: <mike@malloyindustries.com>
Conclusion: Take the Next Step
If you’re a CEO or entrepreneur ready to secure your next round of funding, these approaches can help you succeed. Get in touch with Mike Malloy to apply these strategies to your business.
