Bootstrapping (self funding) seems attractive. You're an industrious entrepreneur building something meaningful with your own resources. No investor is breathing down your neck. You have full control. But the challenge is—how can this continue to work?
I have guided founders to this point. I've watched dreams funded by founders succeed until they collapse. Cash is depleted. Expansion grinds to an abrupt halt. Machinery is repaired rather than finding additional customers. This is where things get painful: determining where to draw boundaries.
It’s not bragging. It is about the money. If money is rolling in quickly continue. You're proving that your scheme is working. But if mere survival is wearing you down or competitors are leaving you behind in money, think again. Raising money is not evil; it is assistance.
Take Joshua T., a client of mine. He bootstrapped his SaaS tool for two years. Solid product, loyal users. But scaling? Impossible without more hands. One funding round later, he tripled revenue in six months. Timing was everything.
So, bootstrap until the numbers scream “help.” When your vision outgrows your wallet, that’s the signal. I’ve guided founders through this pivot—let’s talk if you’re there. Control’s great and winning’s better. Win-win.
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Unlocking cash for your business? That’s my superpower. I’ve fueled over 300 founders to raise $20M+ in funding.
Photo taken by me in my previous hike.
