What if the money you're chasing is actually slowing down your business? In this eye-opening episode, we break down the real-world implications of choosing between bootstrapping and taking on investors with finance veteran Salvatore Tirabassi. With over two decades in venture capital and as a CFO in high-growth environments, Sal cuts through the financial noise to help founders understand when to raise, how much to raise, and most importantly—when to avoid outside capital altogether. Discover why less than 1% of startups should actually pursue venture funding, how to identify your true fundraising milestones, and the hidden dangers of the "raise as much as you can" mentality.
Contrary to popular startup culture, most successful businesses are actually bootstrapped. The venture capital path that dominates tech news creates a distorted picture of how most companies actually grow. As Sal points out, there are specific criteria that indicate when external funding makes sense: when speed-to-market is critical, when you face lengthy sales cycles, or when your business is inherently capital-intensive.
The milestone approach to fundraising provides clarity that many founders lack. Pre-seed funding should get you to a solid MVP with beta customers giving structured feedback. Seed rounds should confirm product-market fit with actual paying customers. Series A proves you have a repeatable business model with predictable unit economics. Each round isn't just about runway—it's about reaching specific business validation points.
Perhaps the most overlooked aspect of raising capital is understanding the investor's perspective. They're pattern-matching against previous successes, looking for credible founders addressing large markets with defensible solutions. But they're also operating a portfolio model where they expect most investments to underperform. When your company isn't among their top performers, you'll often find yourself with less support precisely when you need it most.
The relationship with investors requires ongoing maintenance. Smart founders build investor relationships long before they need money, creating a network they can activate when the timing is right. This approach allows you to push further down the road with your business milestones before actually taking money, which puts you in a stronger negotiating position.
Watch the Full Episode on The Strategic Capital Decision with expert Salvatore Tirabassi below:
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