Courageous Conversations Coaching Transform in 60 minutes or less
Courageous Conversations Coaching

Bring your problem.
Leave with a plan.

One focused session on the thing you want to break through. Bring your pitch deck, GTM strategy, resume, or mindset roadblock. No homework, no course, no twelve week programme. Just Instant Results!

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What it is

Bring the one thing
you are stuck on.

If you are talent, bring us this

  • You graduated, you have applied everywhere, and nothing is landing.
  • You were laid off, and the way back in is not the way you got in the first time.
  • You have the job, the room is toxic, and you can no longer tell whether it is you or them.
  • You are good at the work and still being passed over, and nobody will say why.

If you are a founder, bring us this

  • You have the idea and a first version, and you cannot tell what to build next.
  • You are growing, and the bottleneck stopped being the product and became the people.
  • You are hiring, and the last two hires were wrong.
  • You are scaling, and you need capital, investors who actually help, and talent who do not need managing.

What happens

You bring one problem. The real one, not the tidy version you give people at events. Most of the first few minutes go to finding the actual constraint, because it is rarely the thing you came in to talk about. Then we build the fix together, out loud, and you will see how much of the answer was already yours. Nothing gets parked for later. Nothing arrives afterwards as a worksheet. Expect the question nobody around you is close enough, or brave enough, to ask. And expect to be reminded of strengths you have stopped counting.

How long

One focused sitting. Long enough to get to the truth, short enough that you cannot hide inside it. No deck. No pre work. Bring the real numbers and the thing that is actually keeping you up. You have been circling this decision for weeks. You are closer to the answer than you think, and we do not leave it circling. The session runs on your strengths and what actually motivates you, because that is where your best moves come from. You came in with one problem. You leave with your next moves on it.

What you leave with

Your next moves, in order, with an owner and a date on each. The reason the first one is first, so you can defend it to your team, your board, or yourself at two in the morning. The one thing to stop doing, which is usually worth more than anything you start. The recording, so you can go back to the exact sentence that unlocked it instead of trusting your memory of it. And the session gets published, because that is the deal here. What breaks your week open helps the next person stuck in the same place.

Speed Coaching

Coaching videos
to unlock your mind.

Try speed coaching for instant unlocks

Networking Coaching

The Power of Feedback

Working in Teams

Communication Skills

Growth Mindset (Failure)

Growth Mindset (Success)

First Impressions (30s Pitch)

What it costs

Start free.
Go further when you want to.

Tier 1

Hot Seat Speed Coaching (Trial)

Free

Every week there is a live coaching call. The first 30 to 40 minutes are open. Anyone can join that part, no payment, no membership.

Sessions are recorded and may be published.

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Tier 2

Courageous Conversations Coaching for Founders & Talent

USD $29/mo

Usually USD $99. Founding price.

  • Every week, a live coaching call. Bring the thing that is stuck.
  • The first 30 to 40 minutes are open to everyone. Members then move to a private room for 90 minutes of hot seat coaching.
  • You get the chair. Not a lecture, not a replay.
  • Come in with a mess. Leave with a next step you can take that afternoon.
  • No application, no prep. Turn up and raise your hand.
  • Founders and talent in one room, because someone in that room has already solved the thing you are stuck on.
Tier 3

Talent to Leader Promotion
Fast Track Mastermind

USD $499/mo

Usually USD $999. Founding price.

  • A small room of high performers on the same climb, so that you can encourage each other while you level up.
  • High performance talent nervous system regulation training, so that your biochemistry and your neuroscience are in alignment with your high performance game.
  • Find out what your manager needs to see before they can say yes, then practice showing exactly that.
  • Scripts for asking, for the pushback, and for the number, rehearsed until they sound like you on your best day.
  • Practice the conversation with us first, live, so that you are ready with both your words and your nervous system on the day it is go time.
  • A reputation inside your company that speaks before you do, so the people deciding already know what you bring.
  • Month to month. Take it for the stretch where it matters, stop when it does not.
Tier 4

Visionary Founder to Fundable CEO Growth Mastermind

Paid in full. 12 months. Application only.

USD $7,999/year

Usually USD $9,999. Founding price.

  • Building the future can be a lonely business. This is the room where you stop carrying it alone.
  • Fundable is a standard, not a lottery. You build the metrics story, the data room and the raise narrative that an investment committee already knows how to read.
  • The grant and non dilutive track: the federal, provincial and state programmes you already qualify for, mapped to your business, so you fund the build without giving away a point of equity.
  • Warm introductions to funding partners who have raised over $50M, and to venture specialists who have raised over $100M, made when your numbers are ready and not before.
  • The team behind $38.8M raised in 2.5 years sits with your numbers and shows you what the people on the other side of the table are actually reading.
  • Your own $1 million in 12 months roadmap, quarter by quarter, with an owner and a date on every move, so you stop rebuilding the plan every Monday.
  • A monthly hot seat with Sheldon in a room capped at 20 founders. Bring the real numbers, make the decision you have been circling for a month, and leave with your next moves.
  • Weekly visionary founder peer pod of 4 to 8 founders at your stage, so this week's problems get solved this week instead of costing you a quarter.
  • The personal brand that makes you the obvious founder to back. Positioning, thought leadership and a key person of influence profile, so investors, clients and senior talent arrive already knowing who you are.
  • Coaches, experts and mentors on brand growth, sales, finance and leadership psychology. Every play in the room has been run by a founder and CEO at your stage, with the numbers and the scars, not just theory.
  • The agentic AI systems that do the work a founder should never do by hand, so the week gets shorter while the numbers get bigger.
  • High pressure founder nervous system regulation training, so that your biochemistry and your neuroscience are in alignment with your high performance game.
  • Build ARR and LTV out of the accounts you already have, because revenue that renews carries a higher multiple than revenue you chase.
  • First right to a seat at the 50 Founders Mastermind Retreat and the path into the Brand & Growth Accelerator when you are ready for leveling up into hyper-growth mode.
Courageous Conversations Coaching Transform in 60 minutes or less
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Courageous Conversations Coaching

Claim your session.

Every session is recorded, and we may publish it. That is part of the programme, not an extra.

As it appears on your ID. This is your signature on the release below.

Recording release

Trybe coaching. Recording release

We record every session and we publish from them. That is part of the deal. This page sets out exactly what you are agreeing to.

Who you are agreeing with. Trybe Strategies Inc., a corporation incorporated under the Canada Business Corporations Act, corporation number 1194035-0, of 428 King William Street, Hamilton, Ontario, L8L 1P7, Canada. We trade as Trybe.

What we record. The session, including audio, video, your name, your voice, your image and likeness, and what you say during it.

What you are giving us. You grant Trybe Strategies Inc. a worldwide, perpetual, irrevocable, royalty free licence, which we may sublicense, to record, edit, reproduce, distribute, publish, broadcast, stream and display the session, in whole or in part, in any media now known or invented later. That includes full sessions, clips, quotes, captions, translations, transcripts and promotional material.

Publication is part of this, not an extra. Every session is recorded and may be published. There is no version of this coaching where the session stays private, and there is no box to opt out of it. If that does not work for you, this is not the right programme and you should not book.

What you get for it. The coaching itself, and the recording of it for your own use. That is the exchange, and it is what makes this a licence rather than a permission you could withdraw later.

Say only what you are willing to have published. Because the session may go out, do not bring confidential information, anyone else's private information, or anything you owe a duty of confidence over. If something sensitive comes up, say so during the session and we will try to cut it, although we are not obliged to.

Editing. We cut, clip, caption and translate. You are not entitled to review or approve a session or an excerpt before it goes out.

We are not obliged to publish. We may decide not to publish a session, or to take it down later, and we do not have to give a reason.

Who owns what. We own the recording. You keep everything you owned before, including your business, your content and your intellectual property. Anything we build specifically for you is covered by your own agreement with us, not by this page.

Group sessions. Other people are in the room and they are recorded too. Whatever they share stays in the room. Do not record, screenshot or repeat it anywhere.

Moral rights. You waive your moral rights in the material so that we can edit and adapt it. You keep the right to be credited as agreed.

What we will not do. We will not use the material to suggest you endorse a product or service you have not agreed to endorse. We will not sell your personal contact details.

This is not advice. Coaching is not medical, legal, financial or professional advice. We are not your doctor, lawyer or accountant, and nothing in a session replaces one.

No guarantee of outcome. Coaching depends on what you do with it. We do not guarantee any result, revenue figure or outcome.

Your data. We store your name, email, the time you signed, and the version of these terms you agreed to, as evidence that you granted this release. You can ask us what we hold at any time.

The law. Ontario law, and the federal laws of Canada that apply in Ontario.

Age. You must be 18 or over to grant this.