Go Big with Gib Podcast
Go Big with Gib is a podcast for professionals, business owners and entrepreneurs to talk about their big wins.
Go Big with Gib Podcast
Ep 95. Raising Big Money the Smart Way
We break down why raising larger checks from sophisticated investors can be easier than piecing together small checks, and how to position your pitch, process, and updates to earn decisive yeses. The core theme is simple: competency, consistency, and character turn capital into a selection process, not a chase.
• core premise that big checks can be easier
• differences between small and large investor behavior
• due diligence expectations and data room readiness
• decisive funding and clean closing mechanics
• hold period reporting cadence and trust signals
• positioning to attract right-fit capital, not more capital
• mindset shift from persuasion to selection
If you found value today, share this episode with someone who's out there raising capital, building their business, or learning to think bigger
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Welcome to the Go Big With Gibb Podcast, where we talk to professionals, business owners, and entrepreneurs about their big wins. Welcome back to Go Big With Gibb. I'm your host, Gib Irons, attorney, entrepreneur, and real estate investor. This show is all about how you build health, wealth, and the mindset to live big. Today we're diving into one of my favorite topics, raising capital. And here's a truth I've learned after years in business and real estate. It's actually easier to raise big money from big check writers than it is to raise small money from small check writers. That might sound counterintuitive, but hear me out. When you're new to raising capital, you often start by chasing$50,000 checks. You're pitching friends, family, and small investors who are nervous and skeptical. They need constant reassurance and they don't often fully understand the investment. But when you start talking with experienced investors, people who write six or seven figure checks, everything changes. The conversation becomes more strategic, more efficient, and more professional. Big check writers are not just betting on you. They're analyzing the opportunity. They know what questions to ask, they understand the risk, and most importantly, they know how to make big decisions. Let me walk you through how the savvy investor approaches the process. Step one, due diligence. Big investors dive deep into the fundamentals, the market, the business plan, the debt terms, the track record. They're not afraid of complexity. They want transparency. If you're professional, organized, and responsive, you build trust quickly. And once that trust is there, the size of the check usually matches the level of confidence. Step two, funding. Once they've made a decision, big investors act decisively. They wire the funds on time. They don't nitpick over the details or shift terms at the last minute. They respect your time because they expect you to respect theirs. Step three, the hold period. Here's where you really see the difference. Small investors often require hand holding. They check in frequently, ask about every update, and can be emotionally tied to short-term results. Larger investors, on the other hand, understand that value creation takes time. They want clarity, consistency, and performance, not just constant attention. They judge success by your execution, not your ability to soothe anxiety. So if you're raising capital right now, here's the takeaway. It's not about chasing more investors, it's about attracting the right investors. When you show up prepared with clean financials, clear communication, and a professional offering, you'll find that the big check writers respect that and they'll invest accordingly. But because here's what they're really investing in competency, consistency, and character. That's what separates the amateurs from the professionals in this business. Now, don't get me wrong, there's nothing wrong with small investors. We all start there. But as you grow, your time becomes your most valuable asset. And working with sophisticated investors creates more leverage, less friction, and greater scalability. So focus your energy where it counts. Refine your pitch, tighten your operations, and position yourself to play in bigger arenas. Because remember, it's not harder to raise a million dollars than it is to raise a hundred thousand. It's just different. Thanks for tuning in to Go Big with Gib. If you found value today, share this episode with someone who's out there raising capital, building their business, or learning to think bigger. Once you start thinking like a big investor, you'll start attracting big investors. Keep going, keep growing, and as always, go big.