Carter Simmons

I built the
system.
Now I'll build
yours.

I built AI tools and sales systems from scratch to grow my own businesses. Now I install the same playbook into yours — in 90 days.

Apply for coaching → See how it works
90d
Program length
3×
Tiers to fit your stage
$0↓
Risk. Guaranteed.
Positioning that converts · Outreach systems that actually work · 90 days to first traction · No fluff. No theory. Real results. · Coaching for early-stage founders · Built for founders who are done guessing · Positioning that converts · Outreach systems that actually work · 90 days to first traction · No fluff. No theory. Real results. · Coaching for early-stage founders · Built for founders who are done guessing ·
Who this is for

Three walls every founder hits.

If any of these are you right now — you're exactly who I built this for.

01

You can't explain what you do

People nod and say "cool" — but they don't buy. Your positioning is blurry, and blurry doesn't convert. You know your product is good. Getting others to see that is a different problem entirely.

02

You have a product. No system.

Some days feel productive. Most don't. There's no repeatable way to find customers, start conversations, or close. So revenue is unpredictable at best. You're flying blind every week.

03

You don't know what to do next

The to-do list is long. Distractions are longer. Without clarity on what actually moves the needle, you stay busy and broke — doing everything except the one thing that would change everything.

Who's coaching you

I built this
from nothing.

I'm Carter — a founder who built Milo, an AI CRM for home service contractors, from zero to paying customers — and have since built multiple AI tools helping businesses operate and sell smarter.

I figured out positioning, outreach, and sales the hard way — by testing, failing, and building until something worked. That system is exactly what I teach.

Built for founders like you

You're 0–18 months in. You have something real.

But you're struggling to explain it in a way that makes people want to buy — and you don't have a reliable way to find the right people.

That's not a product problem. That's a positioning and systems problem — and it's 100% fixable in 90 days.

10+
Customers targeted by day 90
3×
Packages for every stage
The process

Three phases. Twelve weeks.

01 / Full audit + action plan
Week one. We go through everything — your offer, messaging, outreach, and positioning. You walk away with a 30-day action plan that has zero ambiguity: what to do first, second, and third.
02 / Build and execute together
Weeks 2–10. Bi-weekly calls, async Slack access, copy reviews, outreach feedback. We build the system in real time and you run it. Every session ends with a diagnosis and a specific next action.
03 / Review, iterate, and scale
Week 12. We audit what worked, fix what didn't, and map the next 90 days. By now the system is yours — and it runs without you. You know exactly how to repeat it.
Program at a glance — 90 days
Onboarding audit call — full review
Wk 1
Positioning document drafted
Wk 2
Offer clarity doc + outreach system
Wk 4
First outreach sent, loop live
Wk 6
Sales conversations happening
Wk 8
Final review + next 90-day map
Wk 12

Guarantee: Complete all sessions and don't have 3 qualified sales conversations by day 90? You get 30 more days free. No questions asked.

Pricing

Three ways to work together.

Not sure which fits? Start with a Clarity Sprint — the cost credits toward Core or Elite. Most clients move up within 30 days.

Entry
Clarity Sprint
One session. Full diagnosis. A written plan you can execute the same day.
$297
One-time · No commitment
  • 90-min 1:1 deep-dive strategy call
  • Full audit — offer, messaging, positioning
  • Written 30-day action plan delivered
  • Positioning statement drafted live on call
  • Full session recording sent to you
  • No ongoing async access
  • No outreach system buildout
Book a Sprint →
Cost credits toward Core or Elite upgrade
Most popular
Core
Core Program
The full 90-day engagement. Build your positioning, outreach, and sales system — together.
$3,000
Pay in full · or $1,100 × 3 months
  • 6 bi-weekly 1:1 calls (60 min each)
  • Async Slack/Loom access between calls
  • Positioning doc + offer clarity doc
  • Full outreach system — list, scripts, follow-up
  • 30-day action plan, zero ambiguity
  • Templates, frameworks, resource library
  • Guarantee: 3 convos by day 90 or +30 free
Apply for Core →
Application required · Limited spots
Premium
Elite Accelerator
Everything in Core — plus weekly calls, done-with-you execution, and daily access. Two spots only.
$6,500
90 days · 2 spots maximum
  • 12 weekly 1:1 calls (60 min each)
  • Daily async access Mon–Fri
  • Carter writes your first 20 outreach messages
  • Landing page copy written for you
  • Full offer buildout + pricing strategy
  • 60-day extension guarantee
  • Priority access to future course + community
Apply for Elite →
Application required · 2 spots only
Results

What clients say.

"

Carter helped me nail my positioning in the first session. Within 45 days I had 4 paying clients and a repeatable outreach system I actually understood. Best investment I've made in my business.

JM
James M.
SaaS Founder, Tampa FL
"

I'd been stuck for 8 months trying to figure out who my customer was. Carter diagnosed it in 20 minutes and gave me a 30-day plan. I closed my first client the following week.

SR
Sarah R.
Service Business Owner
"

The outreach system Carter built with me generated 11 qualified conversations in 30 days. Before working with him I was sending cold messages into the void. Night and day difference.

DK
Derek K.
Agency Founder
Common questions

Everything
you want
to know.

How is this different from a course?+
A course gives you information. This gives you a system built specifically for your business, with someone holding you accountable every step. You're not watching videos — you're executing with a coach who's done it himself.
What if it doesn't work for me?+
Complete all sessions, do the work between calls, and if you haven't had 3 qualified sales conversations by day 90 — you get 30 more days free. No questions, no fine print. The guarantee is real.
Why should I trust you?+
I'm not a career coach who's never built anything. I co-founded Milo, built multiple AI tools for real businesses, and figured out positioning and outreach through genuine trial and error. I coach what I've actually done — not what I've read.
How much time does this take per week?+
The bi-weekly calls are 60 minutes. Outside of that, expect 3–5 hours per week executing on your action plan — outreach, copy, follow-up. This is a hands-on program. If you're not willing to do the work, this isn't for you.
What stage does my business need to be at?+
You need a product or service that exists — even if it's rough. This program works best for founders 0–18 months in who have something to sell but aren't selling it consistently yet.
The guarantee

No results?
You don't pay.

Complete the program fully and don't see results — you get 30 more days free. Here's exactly what that means:

✓Attend all scheduled calls
✓Submit work between sessions for review
✓Execute on the outreach system built for you
✓3 qualified sales conversations by day 90 — or 30 more days, free
"
Complete every session. Do the work. And if you don't have 3 real sales conversations by day 90 — you get another 30 days, free.
The guarantee. No fine print. No hoops. Just results.
Ready to start?

Stop guessing.
Start growing.

Applications take 3 minutes. If it's a fit, we book a call within 48 hours.

Apply now → or email me directly

Spots are limited and reviewed personally by Carter.