Josh Whitaker.
Issue Nº 01Est. 20+ yrs
Black-and-white portrait of Joshua Whitaker, arms crossed, leaning on a brick wall

I am Josh.

I make you better.

Business. Pickleball. Life's a strategy game.

Joshua Whitaker in a white coat standing on snow under the northern lights
01 /

Build Better.

50+ brands launched. Two exits. Got an idea? Pitch me. I'll tell you if it's brilliant, terrible, or somewhere in between.

Joshua Whitaker holding a paddle in a St. Louis Shock jersey after signing with the Minor League Pickleball team
02 /

Play Better.

Pickleball is chess at 40 miles an hour. Stop reacting. Start thinking three shots ahead.

Good ideas are everywhere ✕Good execution isn't ✕Stop hitting the ball ✕Start playing the game ✕I don't sell dreams ✕I help build businesses ✕Good ideas are everywhere ✕Good execution isn't ✕Stop hitting the ball ✕Start playing the game ✕I don't sell dreams ✕I help build businesses ✕
§ 01The Pitch

Your mom thinks your business idea is brilliant. I might disagree.

You're not hiring another marketing consultant. You're pitching an entrepreneur who has spent 20 years figuring out what people actually buy — and who will push back.

If something's interesting, we might talk. Want an hour of my undivided attention? That'll cost you.

Free pitches are reviewed at my discretion. Submitting doesn't guarantee a reply.

§ 02The Record

I've been around the block. Built a few of them, too.

20+

Years in marketing & e-commerce

50+

Brands launched

2

Successful business exits

$1M+

First-year e-commerce revenue

I don't teach business because I read about it. I teach it because I've done it — the launches, the wins, and the occasional expensive lesson.

§ 03Current Projects

I practice what I preach.

I'm not just telling people how to build things. I'm still building them.

§ 04The Deep Dive

Want me to tear apart your business? In a good way.

One hour. Twenty years of experience. Your business under the microscope — what's working, what's broken, and what I'd do if it were my money on the line.

Business Strategy Deep Dive

$500

60 minutes · Live video · 1-on-1

  • Positioning & differentiation
  • Business models & monetization
  • Marketing & customer acquisition
  • E-commerce strategy
  • Product launches
  • Growth opportunities
  • Strategic blind spots
Apply for a Deep Dive
§ 05Pickleball is Chess
Joshua Whitaker holding a paddle in a St. Louis Shock jersey after signing with the Minor League Pickleball team

Stop hitting the ball. Start playing the game.

Your opponent isn't beating you. Your decisions are. Better shot selection, smarter positioning, and seeing the next move before it happens.

Play Smarter
Joshua Whitaker smiling with arms crossed in a white shirt
§ 06About

A little about me. Since you asked.

I've spent more than two decades building brands, launching companies, and making businesses better.

Somewhere along the way, I also became completely obsessed with pickleball.

Turns out the two have a lot in common. The right strategy makes all the difference.

That's what I do. I help people make better decisions.

More about Josh →

So, what do you want to get better at?