What I’ve Learned From 20 Years of Rainmaking

If you’ve ever been in a relationship, romantic, professional, or the kind where you’re still trying to figure out why the other person thought that email was a good idea, you already understand the core truth of rainmaking:

Relationships are everything.

Not “important.”
Not “helpful.”
Not “a key differentiator in today’s competitive marketplace.”

No.
Everything.

In fact, if rainmaking were a marriage, tactics would be the in‑laws: occasionally useful, sometimes annoying, and absolutely not the thing that keeps the relationship alive.

After 20 years of doing this work, here’s what I’ve learned, mostly the hard way, occasionally the funny way, and always with the reminder that people hire people, not proposals.

1. Relationships are the whole game

I used to think rainmaking was about tactics, clever lines, perfect pitches, the right follow‑up cadence. Then I realized something: people don’t remember your tactics. They remember how you made them feel.
Warmth beats wizardry every time.

2. The real work is done long before the RFP

If you meet the client for the first time at the shortlist interview, you’re basically showing up to a potluck empty‑handed.
The menu was decided months ago.
The seating chart is set.
And someone else already brought the good dessert.

3. The best opportunities come from generosity

Helping without expectation is the closest thing we have to business magic.
You answer a question, make an introduction, share a resource, and suddenly you’re the person they trust.
Generosity builds gravity.

4. Clarity wins more work than charisma

Charisma is fun at parties.
Clarity wins contracts.
When your message is simple, buyers relax. When buyers relax, they say yes.

5. Consistency outperforms intensity

A weekly rhythm of outreach beats a heroic sprint every quarter.
Rainmaking is like going to the gym: the people who show up regularly get results. The people who show up once a year get sore.

6. Curiosity is a superpower

The best rainmakers aren’t the ones with the best answers, they’re the ones with the best questions.
Curiosity uncovers the real problem, which is almost never the one written in the RFP.

7. Your network is a living system

It grows when you invest in it, weakens when you ignore it, and thrives on meaningful connection.
It’s less like a machine and more like a garden: water it, prune it, and don’t be surprised when it produces fruit years later.

8. Follow‑up is where deals are won

Most professionals stop one touch too early.
Thoughtful persistence signals commitment, not desperation.
(Desperation is sending a fourth email in 24 hours. Don’t do that.)

9. Confidence comes from reps, not personality

You don’t become a rainmaker by reading about it.
You become one by doing it, with feedback, with reflection, with someone in your corner helping you see what you can’t see yet.
The right coach doesn’t make you someone else, they help you become the version of yourself that clients already want to say yes to.

10. Preparation is a competitive advantage

Most teams wing it.
The team that rehearses like it matters usually wins.
(And yes, everyone can tell who practiced and who didn’t.)

11. The long game always pays off

Deals you plant today may bloom in five years.
Patience isn’t a personality trait, it’s a strategy.

12. Your brand is built in the small moments

The quick thank‑you note.
The thoughtful introduction.
The follow‑up that shows you were actually listening.
These tiny moments stack up into trust.

After two decades of rainmaking, the biggest surprise is that it’s not really about selling at all. It’s about showing up, consistently, generously, curiously, and becoming the kind of person people want to work with. The tactics change, the markets shift, the buzzwords come and go, but the fundamentals stay beautifully human. And if you’re willing to keep learning, keep practicing, and let a few trusted voices help you see what you can’t see yet, you’ll find that rainmaking isn’t a mysterious talent reserved for a chosen few. It’s a craft. A learnable one. If you want to learn more about Rainmaking Coaching use this link. The more you lean into it, the more fun, and fruitful, it becomes.