Your entrepreneurial wingman

Never build alone.

Milo is your always-on wingman: a real, experienced founder behind a friendly face. For one flat monthly fee you get a sharp, in-your-corner partner to think through ideas, solve problems, and keep moving. No equity. No meetings you dread. Pause anytime.

Flat monthly fee Pause or cancel anytime A real human behind the avatar
Milo, your entrepreneurial wingman
The 11pm moment

Every founder hits the moment with no one to call.

A half-formed idea. A hard decision. A wobble of doubt, and no one to think it through with. Cofounders are expensive and permanent. Advisors are slow and pricey. Coaches don't get the startup grind. You just need someone smart, fast, and in your corner. That's the whole job. That's Milo.

How it works

Simpler than booking a coffee.

1

Subscribe

One flat monthly fee. No contracts, no equity, no haggling. Pick the tier that fits where you are.

2

Message Milo

Drop ideas, problems, decisions, half-thoughts, whenever they hit. Voice note, doc, or one messy paragraph, all welcome. A real, experienced founder reads every message and writes back. Never a bot.

3

Keep moving

Get sharp feedback, a clear next step, and someone who actually remembers what you're building. Pause the month you don't need it.

What's included

A cofounder's brain, on tap.

Unlimited messages, answered by a real founder who actually knows your story. No bots, no scripts, no starting over every time.

💡

Idea pressure-testing

Send the messy version. We'll find the holes before your customers do.

🧩

Problem-solving & strategy

Stuck on a decision? Get a clear framework and a straight answer.

🪞

Honest second opinions

Not a yes-man. Milo tells you when the idea has a problem, kindly.

🎯

Accountability & momentum

Set the goal, get the nudge. Someone in your corner who notices.

📡

A sounding board, always on

The 11pm thought doesn't have to wait for a calendar slot.

🤝

Founder morale support

The lonely part nobody talks about. You don't have to carry it solo.

Why Milo

Not a coach. Not a consultant. Not a chatbot.

Milo Cofounder Advisor Coach Generic AI
A real humanYes, alwaysYesYesYesNo, it's software
CostFlat monthly feeEquity, forever$300–2,000+/moPremium hourlyFree–cheap
Always-onYes, asyncYesSlow, scheduledScheduledYes
Knows your storyRemembers everythingYesPartlyPartlyForgets
Pushes back honestlyAlwaysSometimesSometimesSometimesJust agrees
Actually built thingsYes, real operatorMaybeYesRarelyNo
Milo, here in your corner
Meet Milo
"Hi, I'm Milo. Send me the messy version, half-formed is exactly where I'm most useful."
Here's the honest truth: Milo is a real, experienced founder. Someone who has built companies, raised money, made the hard calls, and felt those lonely 11pm moments too. The avatar is just the friendly face, so the focus stays on you and not on a name. Everything Milo tells you comes from a real human. Never a bot.
12+
years building & advising startups
50+
founders helped, one-to-one
0
equity taken, ever
Milo (yes, a real human)

Founding members get 40% off for 12 months.

The first 15 founders to join lock in 40% off for their first 12 months. Help shape Milo, and get the lowest price we'll ever offer.

11slots left
Pricing

One wingman. Three ways to fly.

Start where you are. Move up when you need more. Pause or cancel anytime. Two clicks, no guilt.

Sidekick

For aspiring & earliest-stage founders finding their feet.

$149/mo
or $1,490/year (2 months free)
  • Unlimited async messages
  • 1 active request at a time
  • Reply within 72 hours
  • Monthly check-in
  • Pause anytime
Start with Sidekick

Co-Pilot

For scaling founders who want a true strategic partner.

$799/mo
or $7,990/year (2 months free)
  • Everything in Wingman
  • Unlimited active requests
  • Same-day replies
  • 2× 45-min calls / month
  • Weekly + KPI tracking
Start with Co-Pilot

Every plan includes a 7-day, 75%-back guarantee. Try a month. If it's not your thing, cancel in two clicks.

Questions

The honest answers.

Is Milo a real person or an AI?

Milo is a real, experienced founder. Full stop. The avatar is just the friendly face we put on it, for warmth and consistency, so you always know who you're talking to. Every reply you get is written by a real human who has actually built and advised companies. There's no bot writing your advice.

What kinds of things can I bring to Milo?

Anything. Ideas, decisions, fundraising nerves, a cofounder disagreement, a pricing question, a "is this stupid?" gut-check. If it's on your mind as a founder, it's fair game.

How fast will I hear back?

It depends on your plan: 72 hours on Sidekick, 24 hours on Wingman, and same-day on Co-Pilot. Built around your pace, not a rigid calendar.

Why not just use ChatGPT for free?

ChatGPT is a brilliant mirror. It mostly tells you what you want to hear. Milo is a real person who pushes back, keeps you accountable week to week, remembers your whole journey, and has actually built and advised real companies. You're paying for honest judgement from someone who's been there, not just information.

Can I pause?

Anytime. No guilt, no fees. Life got busy or cash got tight? Pause and come back when you're ready. Milo will be here.

Do you take equity?

Never. Flat monthly fee, full stop. Milo has no stake in your company, and that's exactly why the advice stays honest.

Is what I share confidential?

Completely. What you share stays between you and Milo. No exceptions.

Milo cheering you on Never build alone

Your next idea deserves a wingman.

Stop building alone. A real, experienced founder is in your corner for one flat fee, starting today.

Never build alone →