The Hare & the Tortoise: The Collaborative Investment Strategy

Do you know the story of the hare and the tortoise? Most people think it's about speed. Really, it's about assumptions. One moves fast, burns out, and loses. The other moves with focus, consistency and wins. Not because it was faster. Because it never lost the plot. In investment, we often play the hare. You buy into a company once it’s attractive enough to justify your capital. And then, almost immediately, you start again. Tear it apart. Bring in your own brigade. Shift the culture, the...

Most people think it's about speed. Really, it's about assumptions. One moves fast, burns out, and loses. The other moves with focus, consistency, and wins, because it never lost the plot.

In investment, we often play the hare. You buy into a company once it's attractive enough to justify your capital, and then almost immediately you start again, shifting the culture, the cadence, the structure. Maybe the founder had taken it as far as they could. Maybe the leadership team didn't have the range for the next phase. What happens next is predictable: the team scrambles to adjust while quietly grieving what they've just lost. And it all gets written off as the cost of transformation.

I've seen this play out more than once. And the truth is, it doesn't have to be this way.

Most staff already know what needs to change. Or they've been trained not to speak, or the founder was too attached to make the hard calls. They can see the beloved feature that never sold, the sunk-cost market expansion that's quietly failing, the four-year app build that's still "nearly ready." It often takes new owners two years to see what was already visible: two years of drift, two years of re-learning.

What if you didn't waste that time? What if you invited the team in from day one, told them the truth, asked for theirs, created space to speak without fear? You'd create a window where people can name what they know, where the future isn't something done to them but something they help shape. They'll tell you what's worth saving and what isn't. They'll help you move faster, not slower. They'll help you keep the soul of what works and let go of what doesn't. That's how you avoid two years of drift.

This isn't about softening strategy, and not every company can be saved: some are already over, even if no one has said it out loud yet. But what gets those companies unstuck isn't a machete. It's a map: a systems-aware lens on leadership, a refusal to accept destruction as the only path to growth. Adaptive structures, leadership without collateral damage, growth that doesn't require unnecessary loss.

Collaborative doesn't mean soft. The tortoise didn't win because it was slow: it won because it didn't waste time recovering from its own missteps. If you want to move faster, start by listening.