Joshua Scutts
Back to Home

What would
Josh do?

#WWJD

Drop your business, founder, tech or AI question. The best ones get answered on camera and posted to @joshuascutts.

Just how I'd actually handle it, built from running a 100+ person insurance brokerage, four businesses, and the tech engines that run them all (still coding them myself).

How it works

Step 01

Ask your question

Anything in business, founder life, tech or AI. The more specific, the better the answer.

Step 02

I record an answer

The best questions get a short, no-BS video reply. How I'd actually handle it if it were my call.

Step 03

It hits Instagram

Posted to @joshuascutts tagged #WWJD. You'll get an email when yours is up.

Why my answers hit different

I'm not a guru. I'm an operator. Everything I say has receipts.

#1
Insurance brokerage in Australasia
100+
People hired and managed
4
Businesses + the tech engines that run them
15+
Years building, shipping, scaling

Ask me stuff like this

The sharper the question, the better the answer

01

“How do I take my service business from $5M to $50M without losing the culture that got me there?”

Done it.
02

“My first hire as a founder fell apart in 90 days. How do you actually hire a #2 you can trust with the keys?”

Hired hundreds. Fired a few too.
03

“Should I build my core systems in-house or buy off the shelf? When does custom actually pay off?”

Built the tech engines running my businesses end-to-end.
04

“My competitor just raised. We're profitable but slower. Do I raise too or out-execute them with cash flow?”

Bootstrapped to #1 in the category.
05

“How do I actually wire AI into a real business (not the toy demos) without breaking what already works?”

Done it across four companies.
06

“I'm the bottleneck in my own business. Every decision waits on me. How do I get out of the way without it falling over?”

Lived it. Solved it. Will share the actual playbook.
07

“How do you go from operator to investor without becoming a tourist in your own portfolio?”

Angel investor, NVDA bag, deal flow I say no to weekly.
08

“Three kids, four businesses, no EA. How does the calendar not eat you alive?”

Real systems. Real trade-offs. No woo-woo.

What gets answered first

  • ✓Specifics over vagueness. “How do I scale” gets skipped. “I'm at $3M ARR, 12 staff, churn 8%, what breaks first?” gets answered.
  • ✓Real stakes. Tell me what's actually at risk. The honest version, not the LinkedIn version.
  • ✓Stuff I've actually done. Operations, hiring, custom tech, AI in real businesses, scaling services, founder mindset, going from operator to investor.
  • ✓No legal/medical/financial advice. I'm a builder, not a lawyer. Use your head.

Ask Josh

One question per submission. The sharper the question, the sharper the answer. #WWJD

Min 20 characters0 / 1000

We only use your email to let you know when your question is answered. No spam, no list-selling, no nonsense.

© 2026 Joshua Scutts. All rights reserved.