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๐Ÿ‘‹Hi, I'm Craig Hewitt

Something Is Holding Your Company Back.

It's either you, or it's how it runs.

Two different problems with two different fixes, and most founders guess wrong about which one they have. I do both: 1:1 coaching for the founder, AI advisory for the business. Eight years bootstrapping Castos to 7 figures. Still operating.

15 questions, about 4 minutes. No email until the end.

Craig Hewitt speaking at TinyFest 2024
5โ€“7
Clients at a time

Who's telling you this

An operator, not a consultant

01

I Was the Bottleneck Too

For years Castos ran on my memory, my judgment, and my willingness to push everything over the line. I know exactly how that feels from the inside, and how badly it scales โ€” because I had to dismantle it myself.

02

No Burn Rate To Hide Behind

Eight years bootstrapping to 7-figure ARR, no venture money. Every call had to pay for itself. That constraint is why the advice survives contact with a real P&L instead of a pitch deck.

03

Audit Me Before You Hire Me

I publish the wins, the misses and the costs as I go. Read a year of it, watch the videos, take the audit โ€” you'll know how I think long before you ever get on a call with me.

What Founders Say

From founders I've coached

I always like talking with Craig. He has a way of cutting through noise and giving you exactly the insight you didn't know you needed.
PD
Pierre De WolfeScrapingBee
Craig is a great coach because he has literally been there and done that. He has the experience and the firsthand knowledge of building a business and he really helped me take a step back and evaluated where my business was and what it needed.
CS
Colleen SchnettlerHelloQuery
Craig is an outstanding coach who brings clarity and focus to every session. His thoughtful questions help me cut through the noise and leave each call with a clear action plan and renewed motivation. I feel both supported and pushed to grow every week.
MH
Matt HaymanLinklo
I've leaned on Craig countless times when blocked or confronted with a particularly tricky fork in the road. More than once, a single call with him has translated into clear next steps. Because he's actively scaling Castos himself, his advice is grounded in real SaaS operator experience. If you're a SaaS founder looking for a coach who keeps you moving forward, Craig's your guy.
CD
Cody DuvalKeeping

Prefer to learn alongside other founders?

Founder-Led Growth Engine

A 10-week live cohort for bootstrapped SaaS founders who need a growth channel and can't afford to hire a marketer. About 5 hours a week, with AI running the production line.

The Founding Cohort starts September 8, 2026 ยท 12 seats

See the 10-week plan

The newsletter

Not ready to work together? Read along first.

Every week I write up what I'm actually doing inside my own companies โ€” the AI workflows that stuck, the ones that didn't, and what it's costing me to find out. Join 10,000+ founders reading it.

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Start here

Start with the diagnosis, not the tools

Fifteen questions across the five layers of an AI operating model. You'll get your score, the one layer holding you back, and three concrete moves for this week. No email until the end.

Take the Audit
~4 minutes
Scored across 5 layers
Three moves for this week