Work with Milton
Five ways to get from here to your AI transition.
Start free. Transform when you're ready. No lock-ins, no upsells.
Free
Digest + signal + free Blueprint articles.
- Weekly Digest email
- The Signal (curated AI news feed)
- Free Blueprint articles
- 5-minute readiness assessment
Insider
Depth content + community.
- Insider Blueprint articles
- Insider video blogs
- The Path (full curriculum)
- Private forum + monthly AMA with Milton
AI Transformation (Individual)
Your personal AI readiness plan.
- Personal readiness assessment
- Custom 90-day transformation plan
- Delivered within 5 business days
- 1st month of 1:1 Coaching included
- Extend via 1:1 Coaching tier
1:1 Coaching
Work directly with Milton.
- Dedicated Milton hours
- Personal or organizational projects
- Extends Individual plans
- Email + async access
AI Transformation (Organizations)
Become a Native AI First Organization. Scope and scale AI projects to fit your needs.
- Organization-wide readiness assessment
- 90-day transformation roadmap
- Executive alignment
- Rollout + scale-up support
FAQ
What's the difference between the Individual Plan and 1:1 Coaching?
Individual Plan ($1,250) is a packaged product: personal assessment + custom 90-day plan delivered in 5 business days, with 1st month of coaching bundled in. 1:1 Coaching is ongoing dedicated time (Custom · 2 hr min) — you book it when you want to extend the Plan or for standalone engagements.
When will Insider launch? What do I get for joining the waitlist?
Insider launches once the waitlist hits a critical mass of members. Waitlist signups get 50% off their first year when Insider goes live — Milton emails you a promo code at launch.
Do I need to be an Insider to book Coaching or Org Consulting?
Nope. Insider is a separate content + community tier. Coaching and AI Transformation (Organizations) are service engagements — book them directly without an Insider membership.
What happens after I book a discovery call?
Milton replies within one business day to schedule a 30-min call. We map your goals, timeline, and budget — then propose a scope. No pressure, no upsell.
Payment + cancellation.
Individual Plan is Stripe one-time. Coaching is invoiced. Insider (when live) is Stripe recurring — cancel anytime, access until the end of your billing period.
Can I upgrade from Individual Plan to Coaching?
Yes — that's the intended path. The 1st month of coaching is included; after that, extend via the 1:1 Coaching tier at its Custom rate.