In my book Progressive Partnerships, I suggest that aspiring dealmakers start with deals they don’t care too much about.
Why? Because low-stakes wins build something more powerful than just momentum, they build trust.
Inside GILD Members, we go a step further: “Pitch the relationship before you pitch the investment.” No one wires money to a stranger.
The same principle applies to governance. Through the Veblen Director Program, we advise first-timers to accept any board seat, no matter how modest. The goal isn’t prestige, it’s proof. Prove you can govern, then leverage that seat into something bigger.
Add Value First, Always
This pattern repeats itself across domains:
- Add value before making an ask.
- Deliver on what you promise, no matter the scale.
- Keep showing up.
When you reduce the pressure and focus on consistent value delivery, doors open naturally. Trust becomes the currency that accelerates growth, whether in business, partnerships, or boardroom leadership.
Shrink the Goal, Score the Win
Grand strategies often collapse not because the strategy is flawed, but because people around you don’t yet trust your ability to execute.
So, shrink the goal. Score the win. Earn the confidence that allows you to take the next step bigger, better, and with more buy-in than before.
Take smaller steps. Remove the pressure. The results compound.