What You Can Learn from Serial Founders #109

Hey,

This week, I thought I'd share my experience as a first-time founder vs a second-time founder and what I learned about fundraising.

Also; 

💼 - Thunder is hiring a growth marketer

📸 - Social Snapshot- DEI in VC

📊  - A look at Q4 2024 funding

🎙️ - Ep: 73 - I make capital strategy easy

🆓 - Negotiate your term sheets like a pro

Welcome to issue 109.

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How Much Could You Sell Your Company For?

If a private equity firm or strategic acquirer made an offer to you today, would you take it? Would you know if it's a fair deal? Are you in the position to close a deal?

Getting acquired could transform your life.

Founders don't realize that it usually takes 12-24 months to prepare a company for a successful exit, the sooner you have a plan in place, the greater the potential outcome. 

If you want to get acquired, we can help. Book a free discovery call with our team of experts to explore your options and discuss getting a plan in place that could change your life.

Book a Free Discovery Call

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Social Snapshot

😂 A look at diversity and inclusion in venture capital by Edrizio De La Cruz on LinkedIn.

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Best Ways to Raise Money for Business Using Fundraising Quadrants by Jason Kirby of Thunder - EP 73

In last week's episode, I talked about what type of capital is right for founders at different stages of the "Fundraising Quadrants," a framework I coined to help founders navigate their capital strategy. It's a clear and short video that should answer many questions for you regarding what capital is right for you.

Watch Now

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Data Corner

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Raising Capital for your startup?

Thunder's mission is to guide founders toward the right path to reach their North Star, be it through securing equity or debt financing or navigating the path to a successful exit. 

Talk to us

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The Second-Time Founder Advantage

I've had 4 exits and founded a bunch of companies, before launching Thunder, and the first time I raised money, I made just about every mistake possible. Over-optimistic projections? Check. Wasted time pitching the wrong investors? Check. Taking bad deal terms just to close the round? You bet.
But the second time? That was different.

The truth is, your first fundraise is mostly about survival. You’re figuring things out in real-time, making up for gaps in your network, and navigating a process that’s not always transparent. By the time you do it again, you know what actually matters, what’s a waste of time, and what investors want to see.

So, what do second-time founders get right that first-timers usually miss?

1. You Know How to Control the Narrative

First-time founders pitch like they’re applying for a job: listing credentials, walking through the deck, hoping investors will “get it.” Second-time founders know that fundraising isn’t about getting approval—it’s about selling a compelling vision and making investors feel like they need to be in this deal.

This means controlling the story. Instead of rambling through every detail, you hit the key drivers:

• Why is this market ready now
• Why you’re the team to dominate it
• Why this is a massive outcome, not just a decent business

First-time founders hope investors connect the dots. Second-time founders draw the dots for them.

2. You Cut Out the Wrong Investors Early

In my first raise, I pitched anyone with a checkbook. If they had “VC” or “angel” in their LinkedIn bio, they were getting an email. Rookie mistake.

Second-time founders get disciplined fast. They only target investors who:

• Invest at their stage (no pre-seed VCs for a Series A raise)
• Have a track record of writing checks in their sector
• Can lead the round or add meaningful value beyond just money

You also recognize when an investor is just “curious” versus actually serious. If someone asks for “more materials” but isn’t engaging deeply, they’re probably just fishing for market intel. Next.

3. You Fundraise on Your Terms, Not Theirs

First-time founders take every meeting whenever an investor wants. Second-time founders set the pace.

They know momentum closes rounds, so they control the timeline:

• Investor outreach starts with a batch of strong, strategic names
• Meetings are compressed into a tight window to create urgency
• They set the close date instead of waiting for investors to decide

When investors feel like they might miss out, they move faster. FOMO works.

4. You Negotiate Like You Have Options (Even If You Don’t)

The first time I raised, I was so desperate to get a yes that I barely pushed back on terms. The second time, I realized that everything is negotiable.

Second-time founders don’t just accept the first term sheet that lands. They:

• Get multiple offers (or at least signal they have interest from others)
• Push for founder-friendly terms (board control, dilution protections, fair liquidation preferences)
• Play the long game—raising from the right investor at slightly lower terms is often better than chasing the highest valuation from the wrong one

A good investor relationship lasts longer than most marriages. You want the right partners, not just the biggest check.

5. You Build Fundraising Into the Business from Day One

First-timers think of fundraising as a moment in time, something you start when you need money. Second-time founders know it’s a constant process.

That means:

• Building relationships with investors before you need their money
• Keeping a tight data room so you’re always ready to share financials
• Running a business that’s actually fundable—strong unit economics, clear market traction, and a team that knows how to execute

Fundraising is easier when investors are already watching your progress.

The Biggest Difference? Confidence.

The second time around, you don’t just know how to raise, you know that you can.

You’ve been in the room before. You’ve seen the patterns. You know when an investor is serious and when they’re wasting your time. And, you’ve built something before and (hopefully) exited, giving you real leverage in the process.

If you’re a first-time founder reading this, Hope this helps. 

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Happy with Fundraising Demystified?

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Free Fundraising Resources

As you set goals for the new year, here's my guide to planning out your fundraising over 12 months:
🗓️ Your 12-month fundraising plan- Download it here

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Let's stay in touch:

• Written by Jason Kirby - https://www.linkedin.com/in/jasonrkirby
• Subscribe to our weekly newsletter for market and industry news and tips when it comes to raising capital and growing your business - https://join.thunder.vc
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