Chasing the money: A common Founder Misstep

This might be one of the most challenging and controversial blogs I’ve written—but it shouldn’t be.

One of my top five books is The Hard Thing About Hard Things by Ben Horowitz. It’s a constant reminder that being a founder involves making difficult decisions. Founders are bombarded with advice from countless mentors and advisors—many of whom claim to be experts. Some come from startup accelerators. However, I believe much of this advice is flawed. Why? Because few of these so-called experts have ever been founders themselves. Worse yet, many are under 35.

Now, I’m not suggesting that younger people aren’t incredibly bright or valuable. But there’s a reality that cannot be ignored—anyone under 35 is unlikely to have experienced enough of the real challenges founders face for their advice to be reliably applied. Sure, there are exceptions, but they are rare.

In a previous blog, I covered the top challenges founders face. Since then, I’ve personally engaged with over 300 founders, particularly in the digital healthtech space where my venture capital firm, Dreamoro Ventures, is focused.

One common and dangerous misstep I frequently see is founders “chasing the money.” And, unfortunately, it’s a mistake that’s often encouraged by accelerators and advisors. The advice usually goes something like this: “Do whatever it takes to secure your first revenue. It’s a proof point that will attract investors.”

Instinctively, this might sound reasonable. But 99% of the time, it’s the wrong move.

I’ve made the same mistake myself in the past, and after much reflection, I hope these examples will help clarify why chasing the money is not a strategy—it’s a costly distraction.

The Problem with “Chasing the Money”

The root issue lies in the fact that many founders lack a well-thought-out, objective commercialisation strategy. This is understandable—most founders don’t have experience creating or executing “strategies”. Many follow the “build it, and they will come” mindset, which is the right approach in rare cases but not for the majority.

Here’s a typical scenario:

A founder has identified an opportunity in the health insurance industry. During their market outreach, they’re approached by a company that packages health insurance for corporate clients. This potential customer likes 75% of the founder’s product but requires some extra functionality. They’re willing to sign up as a paying customer.

Naturally, the founder is excited—this seems like a great adjacent opportunity to bring in revenue. They begin customising the product to meet the new requirements, thinking it will be a quick adjustment.

The Hidden Dangers:

1.                          Resource Dilution: As a founder, your time and resources are limited. Diverting them to meet new customer demands distracts you from refining your core product.

2.                          Market Focus Drift: Engaging with this customer pulls you away from proving your original market thesis. Your primary focus gets diluted.

3.                          Side Hustle Trap: This deal doesn’t validate your core model; it’s a side hustle that could derail you from the original vision.

4.                          Investor Perception: Investors value focus. If they see you chasing small, adjacent revenue opportunities, they’ll question your ability to scale and use capital wisely.

5.                          Team Confusion: Your team will struggle to align on priorities. Are you focusing on your core product, or are you pivoting to serve one client?

6.                          Pricing Distortion: You may find yourself adjusting pricing to accommodate this one client’s needs, which doesn’t align with your long-term pricing strategy.

7.                          Tech Debt: Every customisation you make to satisfy a one-off customer adds to your tech debt, creating functions that aren’t core to your business, that you need to maintain and support.

A Second Example:

Let’s say you’re a founder working on a digital health platform that connects patients with specialists. You receive an inquiry from a large telemedicine provider. They love your platform but want an integration with their existing electronic medical records system. They’re willing to pay for this integration, and the offer is tempting.

But think carefully:

1.                          Integration Complexity: Building custom integrations could take months.

2.                          Non-Core Offering: Your product is about patient-specialist connections, not medical record systems.

3.                          Investor Red Flags: If you’re spending time on complex integrations rather than scaling your core model, investors will wonder if you’re distracted.

In both examples, chasing immediate revenue may seem enticing, but it pulls you away from validating and scaling your core business. This isn’t a pivot—it’s a distraction. And it almost always leads to bad outcomes.

The Takeaway: Don’t chase the money. Stay focused on your core product and market. Making the hard choice to say no is what separates successful founders from those who end up drowning in distractions.