If you’re like me, it might have been Labor Day in the U.S., and it was a beautiful one here in Austin, not putting in any work is more or less impossible; besides, entrepreneurs throughout the world were working and so with the focus on work, I couldn’t help but put thought to this frequently asked question, “How do I know if I should bootstrap or raise capital?” Bluntly, if you’re asking whether to raise capital or bootstrap, you’re falling into a trap. This question is framed like some sort of morality test for entrepreneurs; are you pure enough to “do it yourself,” or are you “selling out” by taking investors’ money? That’s nonsense. The right decision isn’t about pride or purity; it’s about math. Specifically, it’s about return on investment (ROI) – for you, for your partners, for your customers, and for anyone who might put money into your business.
The problem is that too many people peddle bootstrapping as the one true path, like entrepreneurship is a monastic order. “Never take outside money,” they say. “Build it yourself, rely on customers, keep control.” Nice sentiment. Except, of course, when your company collapses because you needed capital to scale, compete, or even survive, and you refused to take it because some LinkedIn guru told you to stay “lean.” That isn’t wisdom, it’s negligence.
Article Highlights
What Bootstrapping Really Means
Bootstrapping simply means you’re financing the business out of your own pocket, or from customer revenue. That’s still capital. It’s just your capital. I have a saying, “everyone bootstraps, until they don’t,” given the fact that there is not funding to start something. Requiring your own capital, like any other source of money, it comes with an ROI question. Can you spend your limited cash in a way that sustains the business, grows revenue, and keeps customers happy? Sure. But what happens when your competitors raise $10 million, hire a sales team of 50, and suddenly every one of your leads is getting cold-called three times a day? Being “lean” is noble; being undercapitalized is fatal.
Bootstrapping can work beautifully when:
- The cost of acquiring and serving customers is low.
- Growth is steady and predictable.
- You’re not in a market where scale itself is the moat.
But if any of those conditions break, bootstrapping can become a slow bleed toward irrelevance. If we’re being blunter, given the distinction of startup from a new business, most need to raise capital.
External Capital: Same Math, Different Players
When you raise money, you’re not dodging the ROI question; you’re multiplying it. Now you have to deliver returns not only to yourself but to whomever gave you money. That means different expectations depending on the source, for example:
- Banks: They don’t want equity, they want interest. The math is straightforward—can you pay back principal and interest without burning your assets as collateral? Fail that test, and you’re toast.
- Government / Grants: Government grants offer “free” non-dilutive capital and credibility but come with strings; reporting burdens, restrictions, and the risk of chasing bureaucracy instead of customers. Besides, this less-restricted capital in early, is actually known to cause challenges when you need investors later.
- Business Partners: Friends, family, or co-founders bringing in capital will expect both repayment and influence. The math here isn’t just financial; it’s emotional. Can you meet their expectations without hating each other by year three?
- Investors: This is where things get hairy. Investors aren’t writing checks because they like your product demo and certainly not on an idea. They’re buying a return. For small businesses, that might mean a 2–5x return over a decade. For startups, actual startups, not just “a new business,” the expectation is closer to 20x. Yes, twenty. Why? Because most startups fail, and the few that succeed need to cover all those losses.
This is also why founders whine that “investors tried to take over my company.” Well… yes, sort of. They gave you money and have a fiduciary duty to get it back, multiplied. That’s not “evil VC culture,” that’s literally their job.
Startups vs. Businesses: Stop Confusing Them
Here’s where most founders get it wrong: Venture Capital isn’t for businesses. It’s for startups. A business is built to operate within the rules of the market. A startup is built to change the rules of the market. Businesses generate steady returns; startups swing for moonshots. Conflating the two is like blaming a casino for not offering mortgages, different game, different math.
If you’re building a bakery, investors aren’t looking for a 20x return; they want steady repayment or maybe a modest equity exit. If you’re building AI that replaces every bakery cashier in America, that’s where VCs line up, because the upside could justify the risk.
So, Bootstrap or Raise Capital?
You don’t decide based on ideology, ego, or what your Twitter feed says. You decide by answering a cold, clinical question:
Does your venture both warrant outside capital (meaning it needs it) and have the capacity to deliver the expected return?
- If yes, you raise.
- If no, you bootstrap.
- If you don’t know, you’re not ready for either.
That’s it. Everything else is noise.
and have the capacity to deliver the expected return?
The tragedy is that entrepreneurs often approach this question emotionally, not mathematically. They conflate control with prudence, or they confuse ambition with necessity. The only real mistake is assuming one path is inherently “better.” The right choice is always the one that aligns your venture’s needs with the capital structure that can sustain it.
Harshly? If you insist on bootstrapping when your market dynamics require scale, you’ll die. If you chase VC when your business can’t produce venture-scale returns, you’ll also die; just slower, with fancier coffee.
The entrepreneurs who thrive are the ones who stop asking “Should I raise or bootstrap?” and start asking, “What capital structure gives my business the oxygen it needs, while delivering the returns my stakeholders require?” And here’s the trick, knowing who to ask… you should be connecting with and talking to investors NOW, not when you are ready or need to raise capital. Venture Capital firms have teams of people who have a job and responsibility to meet with you and share expectations. Angel Investors should meet with you (or at least answer an email) and explain. If you’re struggling with either, well, that’s why I write, that’s why Founder Institute exists, and that’s why you should be questioning advisors when they tell you what you think, “Great, thank you for that advice. Now, how do I do that and put me in touch with someone.”
