Capital Raising

Last edited:

Mar 1, 2025

by

Kyle Edwards-Brooks

Capital Raising

Last edited:

Mar 1, 2025

by

Kyle Edwards-Brooks

Why the Fundraising Process Never Stops: Secrets to Building Long-Term Investor Relationships

Most founders believe that fundraising is a one-and-done event—something you tackle only when you're running out of cash. But ask any successful founder or seasoned investor, and they’ll tell you the truth:

Fundraising is an ongoing process that never really stops.

Building long-term relationships with investors, even when you’re not actively raising capital, is one of the most powerful things you can do to secure future funding faster, on better terms, and with aligned partners.

In this article, we’ll explore why ongoing investor engagement is critical, how to maintain momentum after a raise, and real-world examples of companies that succeeded because they never stopped fundraising behind the scenes.

Why Fundraising is a Continuous Process

1. Investors Back Relationships, Not Just Deals

Raising capital is fundamentally about trust and relationships. Investors rarely write checks to founders they’ve just met. Instead, they prefer to watch a founder's progress over time, evaluating how they handle growth, challenges, and opportunities.

As Mark Suster, venture capitalist at Upfront Ventures, says:

“Invest in lines, not dots.”

Meaning, investors invest when they see a track record of progress (lines)—not just a single impressive meeting (a dot). (Source: Both Sides of the Table)

2. Future Rounds Depend on Ongoing Trust

Your next round of capital—whether it's a bridge round, Series A, or Series B—will be infinitely easier if investors are already primed, informed, and engaged. You don’t want to start building relationships when you’re desperate for cash.

3. Markets Shift Quickly—You Need to Be Ready

Opportunities arise unexpectedly. Market dynamics shift, and new investors may show interest. If you’re always ready, with warm investor relationships, you can take advantage of funding opportunities when they come—without scrambling.

Real-World Examples: How Staying Engaged Paid Off

1. Airbnb: Ongoing Updates Helped Raise $112 Million

When Airbnb was struggling to raise capital in its early days, co-founders Brian Chesky and Joe Gebbia kept potential investors updated monthly—even after being rejected.

Over time, as Airbnb gained traction, these updates kept investors engaged and informed, making it easier to close their $112 million Series B led by Andreessen Horowitz in 2011.

💡 Lesson: Even after rejection, stay in touch. When traction improves, investors who’ve been following your journey are more likely to invest. (Source: Business Insider, "How Airbnb Raised Money Even After Rejection")

2. Stripe: Leveraging Investor Relationships for Rapid Scaling

Stripe, now valued at nearly $50 billion, built its investor network long before becoming a household name. Founders Patrick and John Collison were constantly meeting with investors, sharing product updates, and building trust.

When they were ready for larger rounds, they didn’t need to "pitch"—investors were already familiar with their progress and vision, making each round faster to close.

💡 Lesson: Build relationships before you need the capital—so when you do, the deal is halfway done. (Source: Forbes, "The Making of Stripe")

How to Maintain Momentum After a Raise

✅ 1. Send Regular Investor Updates

Founders should send monthly or quarterly updates that cover:

  • Growth metrics (revenue, users, engagement)

  • Key wins (new customers, partnerships)

  • Challenges and how you’re solving them

  • Ask for advice or introductions when needed

📝 Example of a simple structure for an investor update:

  • Highlights: Major wins or progress

  • Metrics: Growth stats (MRR, ARR, CAC, LTV)

  • Challenges: Key obstacles and solutions

  • Asks: Specific help or introductions

Example: Buffer, a social media company, publicly shared their investor updates template, which is now widely used by founders to maintain transparency and trust. (Source: Buffer Open Blog)

✅ 2. Build a Long-Term Investor Network

Engage with new investors even when you’re not raising. This can include:

  • Meeting investors at events and conferences

  • Connecting on LinkedIn and sharing company milestones

  • Sending occasional updates to new connections

🔥 Tip: Share personalized updates and insights—don’t spam them with generic decks. Keep them in the loop on your unique progress.

✅ 3. Always Be "Soft" Fundraising

You don’t need to actively "raise" to stay on investor radars. Keep conversations warm by:

  • Asking for feedback on strategy (without asking for money)

  • Sharing milestone achievements

  • Staying involved in investor communities

📈 Example: Companies like Hopin, which scaled to a multi-billion-dollar valuation in under two years, maintained ongoing dialogues with VCs, allowing them to close rounds in weeks—because relationships were already built. (Source: TechCrunch, "How Hopin Raised $400M Fast")

Why This Approach Works: What Investors Say

  • Nikhil Basu Trivedi, VC at Footwork, says:

“The best founders are in touch before they’re raising, building relationships so that when it’s time, investors already know the story.”

  • Sarah Guo, former VC at Greylock, notes:

“Some of the best investments I’ve made were in founders who kept me in the loop over months, even years.”

✅ Key Investor Insight: If you only reach out when you need money, investors may feel like an ATM, not a partner. But if you engage regularly, they feel like part of the journey—and are much more likely to invest when the time comes.

Final Takeaway: Build Now, Not Later

If you take one thing away from this article, let it be this:

Start building investor relationships today—before you need them.

Capital raising is never over—the better your relationships, the easier, faster, and less stressful it will be when you do need to raise again.

3 Key Actions for Founders:

1️⃣ Send monthly/quarterly investor updates—even to those who passed.
2️⃣ Meet new investors regularly to build a network before you need it.
3️⃣ Stay top of mind by sharing growth stories, insights, and challenges.

💼 At Brookstone Capital, we help founders craft powerful investor relations strategies that turn cold leads into warm investors ready to write checks when the time is right.

📲 Want to build investor relationships that lead to funding? Contact us today.

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