For bootstrappers with traction, raising a small amount of capital isn't about chasing venture scale. It's a strategic move to accelerate quitting your day job, buying back precious time. Trading a small percentage of equity to go full-time faster is a powerful bet on yourself and your own efficiency.
The primary purpose of hiring is not to add capacity for growth, but to free up the founder's time from low-value tasks. This allows the founder to reinvest their unique talents into activities that truly drive the business forward, making growth an outcome of strategic time reallocation.
Raise capital when you can clearly see upcoming growth and need resources to service it. Tying your timeline to operational milestones, like onboarding new customers, creates genuine urgency and momentum. This drives investor FOMO and helps close deals more effectively than an arbitrary deadline.
By selling your personal time at a premium to one client, you can cover your personal living expenses. This frees up 100% of the business's revenue for reinvestment, dramatically accelerating growth without needing external capital. It's a key bootstrapping strategy.
Avoid the classic bootstrap vs. raise dilemma by using customer financing. Pre-sell your product or service to a group of early customers. This strategy not only provides the necessary starting capital without giving up equity but also serves as the ultimate form of market validation.
The act of raising capital is not an achievement in itself; it's merely acquiring a tool. The real accomplishment is using that capital to build a durable, lasting business. Shift your focus from celebrating funding rounds to celebrating the creation of a sustainable enterprise.
The primary goal of hiring should be to reclaim the founder's time from low-value tasks. This frees up the business's most valuable asset—the founder—to focus on high-leverage activities that truly drive growth, rather than simply adding capacity.
Despite a $50 million exit from their previous company, the Everflow founders intentionally limited their initial investment to a few hundred thousand dollars and didn't take salaries for two years. They believed capital scarcity forces focus and efficiency, preventing wasteful spending while they were still figuring out the product.
Bootstrapping is often a capital constraint that limits a founder's full potential. Conversely, venture capital removes this constraint, acting as a forcing function that immediately reveals a founder's true capabilities in recruiting, product, and fundraising. It's the equivalent of 'going pro' by facing the raw question: 'How good am I?'
Reflecting on raising $35M, Ergatta's founder suggests taking less capital might have been wiser. While tempting to raise as much as possible, large funding rounds lock the company into a specific financial trajectory and set of expectations. Raising less money can preserve crucial optionality and flexibility for the business's future.
Accel Events' founder challenges the 'go all in' mantra. He worked a day job for 5 years to bootstrap to $1M ARR. He argues this path, while slower, de-risks the business and proves the concept, allowing founders to hold onto significant ownership instead of raising a large, dilutive seed round early on.