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Why We Still Believe in Bootstrapping

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Koby Jackson

There’s nothing quite like the energy of the startup. 

When you’re bootstrapping, every decision matters. Every win feels massive. And every person on the team is rowing in the same direction, not because they were told to—but because they believe in where the boat is going.

In the early days of Calldrip, we didn’t have big budgets. We didn’t have deep-pocketed investors whispering in our ears. We didn’t have rooms full of strategists analyzing market trends.

What we did have was clarity.

  • Clarity of mission.
  • Clarity of urgency.
  • Clarity of customer focus.

We were just a handful of people who saw something broken in the sales process and believed we could fix it—starting with the most overlooked part: Quick response and follow-up.

Too many leads were going cold. Too many teams were responding hours (or even days) after a customer expressed interest. Too many sales opportunities were lost not because the product wasn’t great—but because the response time was.

So we built Calldrip to change that. To make speed-to-lead the default. To empower sales teams to respond instantly. And we did it without the cushion of millions in VC money. We did it the hard way.

Bootstrapping forces you to focus.

You’re not building for headlines or funding rounds.

You’re building for your customers.

We still live by that today. That startup energy? It’s still alive at Calldrip. It’s why I wake up every day fired up to keep building. We’re not here for the show. We’re here to serve.

That same focus on serving customers is what drives everything we do—and it's what I want to share more of.

And that’s why I’m launching a new blog series: The Startup.

This series will share stories from our early days, the power of unity and urgency, and why some of the best innovations are born from necessity—not from pitch decks. I’ll also be diving into something I believe more founders should talk about:

Why big capital and investment bankers are bad for customers.

When a company raises a mountain of cash, the focus starts to shift. Instead of solving real problems for real people, the energy shifts to satisfying board members, chasing hypergrowth, and hitting investor-fueled milestones which often leads to massively overpriced tools. 

Too often, the customer gets left behind.

At Calldrip, we’ve never forgotten who we’re building for. That’s the edge that bootstrapping gives you—and it’s one I’ll never trade.

Stay tuned. There’s more to come.


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