Decisive
Operator

I make your company money—or walk empty handed.

Telecom turnarounds. Amazon insider. Now betting on founders.

Equity or rev-share. If you don't win, I don't eat.

The Full Story Work With Me

The Pattern

In 1994, Sears cancelled their catalog—the original "everything store." Two years later, Amazon launched. Sears had the playbook. They let it slip away.

I've spent 20 years watching this pattern repeat. The incumbents get comfortable. The founders get hungry. Power shifts.

I cut my teeth in telecom—six companies, multiple turnarounds. Cbeyond, Birch, Xspedius, Airband, Alpheus, Windstream. Chaos was the job. At Cbeyond, I was their #1 rep nationally and watched us go from scrappy startup to IPO. Learned what it takes to scale—and what it takes to maintain control when the suits arrive.

Then I went to Amazon. Not to coast—to learn. I wanted to see how Big Tech actually operates from the inside. Grew my org from $1B to $3.2B. Built AI-powered systems. Pushed hard. Shipped fast.

And I confirmed what I suspected: They're stuck.

I love the people at Amazon. Brilliant, hardworking, good humans. But the machine is slowing down. Apple without Jobs. Amazon without Bezos. Big Tech struggles to innovate without founders at the helm. The same vulnerability they exploited in the 2000s? They have it now.

AI is the new catalog. The founders who grab it will be the next Amazon. The companies that committee-meeting their way through this window will be the next Sears.

Where I've Been

Amazon

$1B → $3.2B

Went inside to learn the playbook. Grew a $1B org to $3.2B. Built AI-powered partner scoring and sales intelligence tools. Led cross-functional teams across time zones. Pushed first-principles decisions in a culture that rewards consensus. Learned exactly how the machine works—and where it's breaking.

Cbeyond → IPO

#1 Rep Nationally

Joined when we were scrappy. Rose to #1 rep in the country. Had pull way above my title. Watched us go from startup chaos to public company. Learned what it actually takes to IPO—and how founders can maintain control when the board starts circling.

Telecom Turnarounds

6 Companies

Birch, Xspedius, Airband, Alpheus, Windstream. Operator experience across six telecom companies navigating chaos, consolidation, and reinvention. Not MBA theory—real decisions with real consequences. This is where I learned that speed beats perfection and bureaucracy kills.

Who I Work With

Ideal Founder

  • → Stage: Pre-seed to Series A. Some traction. Past the "idea on a napkin" phase.
  • → Problem: GTM bottleneck, ops chaos, or you need someone who's seen the pattern before.
  • → Mindset: Moves fast. Wants to build something huge. Sees the AI window.
  • → Vertical: AI-native, B2B SaaS, or tech-enabled services.

Not For You If...

  • ✕ You want validation. I'll tell you when your idea is broken.
  • ✕ You need six months to make a decision. I operate at founder speed.
  • ✕ You want decks and process docs. I ship outcomes.
  • ✕ You can't handle direct feedback. I'm not here to be nice.

How It Works

1

You Apply

Fill out the form. What you're building, where you're stuck, why now. I read every one personally.

2

We Talk

30-minute call. I'll tell you exactly what I see—good and bad. No pitch, just honest assessment.

3

We Bet

Equity, rev-share, or milestone-based. I only win if you win. Skin in the game—both sides.

The Thesis

Amazon and Facebook disrupted legacy companies in the 2000s because those companies couldn't adapt fast enough.

Now Big Tech is the legacy. Post-founder, committee-driven, slow. The same pattern is playing out again.

AI-native startups with hungry founders will own the next decade. The window is open right now—and it won't stay open long.

I'm not advising from the sidelines. I'm betting on the builders who see it.

Let's Talk

I make money—or I walk empty handed.

This isn't a newsletter signup. It's an application. Be direct.

I respond to every serious application within 48 hours.

Building in public. Real-time takes on X.

Follow @TheNathanOne