Greg Isenberg

Greg Isenberg

High quality insights on internet communities, building products communities love and startups. This weekly email will get your creative juices flowing.

Simon Severino almost went home.

His audience… Six peoplesitting in folding chairs.

His first instinct: leave and play tennis.

He stayed. Gave his talk.

Afterward, one person approached him.

"I'm from Google. We need someone more agile than our current agency. Would you work with us?"

That decision to stay in an empty room changed Simon's business.

Here's what he did next—and how you can use the same approach.

The System Behind the "Lucky Break"

Simon had written Google at #1 on his Dream 100 list months earlier.

The list sat unused on his desk, working in his subconscious.

Dream 100 works like this:

  • Write down 100 people who need what you solve

  • Don't filter for "realistic" or "feasible"

  • Just write

The Charlie Munger Story

Chet Holmes created this for Charlie Munger.

Munger's newspaper ranked dead last nationally.

Holmes identified the 100 biggest advertising spenders.

Four years later, they'd signed 33 of them.

The newspaper jumped to second place.

The math is simple:

  • One prospect per week = two years

  • Two per week = one year

  • Scale accordingly

Uncovering AI

Uncovering AI

Learn how to leverage AI to skyrocket your productivity and create quality over quantity.

The Wingman Strategy

After the Google meeting, Simon developed a system.

He calls it "becoming someone's wingman before they become yours."

The 5-Step Process:

1. Find them on LinkedIn

2. Like and comment on their content

3. Learn about them

4. Create value in comments

5. Invite them to your platform (podcast, event, etc.)

Real Example: Landing Brendon Burchard

Sean Malone used this to land Brendon Burchard as a client.

He sent Twitter messages for weeks. No response.

Then he went to Africa, saw animals, and remembered Brendon's story about a car accident in a jungle.

He sent photos of lions with a note about Brendon's experience.

Brendon responded immediately.

The key: Study what they care about. Most people skip this step.

🐝 The Investing Show

🐝 The Investing Show

Join me as I turn $50K into $4M in public. Status: 🟩🟩🟩🟩🟩🟩🟨⬜️⬜️⬜️ Sharing the compounding portfolio (reliable compounders) and the income portfolio (monthly income).

Three Critical Mindset Shifts

1. Unlearn Everything

Rick Rubin never says he "failed."

He "explores."

This removes the paralysis that stops most people from attempting big partnerships.

2. Act Like You Know Less

Simon learned this from Socrates and the Sandler sales method.

When someone says "That's brilliant," don't keep talking.

Ask "What do you mean?"

Make them explain why your idea is valuable. It cements their conviction.

3. Work ON the Business, Not IN It

Simon cancels meetings to walk in the sun.

He talks to AI while walking, asking strategic questions he'd ask Jay Abraham.

Two hours of "not working" generates his best ideas.

Most consultants bill hours. Simon built systems that work without him—inspired by studying McDonald's, not other consultancies.

What This Means for Your Business

You don't need connections to reach influential people.

You need systems.

The entrepreneurs dominating their markets understand this. They:

  • Study their targets

  • Provide value first

  • Think beyond their industry for solutions

Your Dream 100 is waiting.

The question is whether you'll show up to the six-person audience when it matters.

Watch the full conversation to see exactly how Simon landed Jay Abraham as a partner and turned Strategy Sprints into a company that attracted Google.

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