Why Pestering Pays Off

The best deal we closed in 2024 (and how persistence made it happen)

Author

Bryan Wish
November 21, 2024

What do Nelson Mandela and closing sales have in common? Stick with me here—this connection changed how I approach closing deals forever.

Two and a half years ago, I was deep into Mandela's "Long Walk to Freedom" when something unexpected jumped out at me. 

He was talking about dating, of all things, and mentioned how a woman he was pursuing actually appreciated his persistent follow-up.

While Mandela's dating advice hasn't exactly revolutionized my love life (still working on that one), it completely transformed my approach to sales. 

Here's how that wisdom helped me land our biggest deal of 2024.

The Setup: When Opportunity Knocked

My dopamine levels shot through the roof like a kid who just found where his parents hid the Christmas presents.

The prospect? Pure gold. 

They had everything we love: finesse, grit, an awesome business built from scratch. Classic underdogs in their industry, but you could smell the potential from a mile away. The founder reminded me of those rare breeds who are truly destined for greatness.

First call? Smooth as butter... or so I thought.

The Plot Twist

They asked for a proposal. I sent it. And then... crickets. Well, worse than crickets—a "thanks, but no thanks." 

It felt like getting dumped before the first date even happened.

But here's where Mandela's wisdom kicked in. What did I have to lose?

The Persistence Playbook

Here's what I did next:

1. Sent a thoughtful follow-up with key compromises

2. Tapped into my network (shoutout to Marty Pollak and Andrew Unger!)

3. Made unsolicited introductions to potential customers

4. Put my social capital on the line with at least five different connections

The result?

They came back. But the real validation came during our first onboarding call when their business partner said they had met their match. 

Of course, the goal isn’t to annoy the crap out of potential customers. It’s to be persistent, even if the odds don’t seem to be in your favor. That takes some skill. Here’s how I do it:

How to Pester Effectively

1. Be Relentlessly You: Highly driven people appreciate relentlessness in others. When you find clients who match your team's DNA, know that magic can happen—even if they don’t see it yet. Keep showing them. .

2. Leverage Your Network Wisely: Your relationships are like chess pieces—use them strategically to demonstrate value before you're hired (and maybe even after they’ve hired someone else).

3. Walk the Talk: There's nothing better than knowing your persistence was worth it because you can truly deliver results. We’re crushing it for this client right out of the gate because there’s so much alignment between our companies and we’re committed to getting it right. 

Sometimes, the best relationships start with a "no."

What's your take on persistence in business? Have you ever had a "no" turn into your biggest win? Hit reply and let me know—I'd love to hear your story.

P.S. If you're wondering whether you should follow up with that prospect one more time... this is your sign. Do it.

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