The pushback you need before the stakes are real

Not a coach. Not a consultant. A peer who thinks with you, challenges you, and helps you get to action.

Get in Touch
The Problem

Big decisions need real pushback

The bigger the decision, the fewer people will tell you the truth. Your team waits for direction. Consultants validate their frameworks. Your network gives well-meaning generalizations.

What you actually need is someone with no agenda except helping you think clearly. Someone who challenges you before the decision is made, not after. Someone comfortable enough with complexity to sit in the uncertainty with you.

The hard part is never the strategy. Strategy is easy on paper. The hard part is navigating the messy reality of making it happen. Stakeholder politics. Competing priorities. Trade-offs that could go either way.

Strategic Sparring is built for this. A peer who's done the work themselves. Someone who respects what you're facing and won't oversimplify it. We think together, challenge assumptions, and figure out not just what to do but how to actually do it.

The Solution

The Sparring Process

01
We challenge your assumptions
We ask sharp questions that force clarity. We call out fuzzy thinking and tell you when we think you are wrong.
02
We stress test your ideas
Before you commit, we pressure test your logic. We poke holes, play devil's advocate, and surface weak spots while they are still cheap to fix.
03
We use AI, then we shut it up
We bring AI in to generate alternatives, surface blind spots, and stress test the reasoning. Then we kick it out when it is time to decide. The call stays human.
04
We rehearse through scenarios
We create realistic situations and run them end to end. We simulate counterarguments, trade offs, and second order effects so you can practice before it is real.
05
We help you execute
We turn thinking into moves. Not just what to do, but how to do it in your reality: constraints, stakeholders, sequencing, and next steps.
06
We build you leverage
When thinking isn't enough, we roll up our sleeves. Mental models you can apply tomorrow, small automations that reclaim your time, and practical artifacts that amplify how you work.
Examples

See what you could explore

A sparring partner with decades of experience. AI systems that surface what humans alone would miss. Your challenge gets both.

AI + Strategy

Scenario planning with AI in the room

Too many variables, not enough time. We use AI to model scenarios and surface blind spots, then decide together.

People

Preparing for a board conversation

A big ask or a tough update. We rehearse the conversation, anticipate pushback, and sharpen your argument before you walk in.

Decisions

Should we pivot or push through?

Your product has traction but not enough. We stress-test the arguments for both sides and find what the data is actually telling you.

Decisions

Killing a project your team loves

The numbers say stop but the team is invested. We rehearse the call and how to communicate it without losing trust.

AI + Strategy

Figuring out where AI fits in your business

Everyone says you should "do something with AI." We cut through the noise and find the two or three places it would actually matter.

People

A co-founder relationship under pressure

Things are tense and avoidance is making it worse. We map what's really going on and figure out how to have the conversation.

People

Reorganizing without losing your best people

The structure needs to change but the politics are real. We think through who to move, when, and how people will react.

Decisions

Taking a role you're not sure about

A compelling offer, but something feels off. We work through the trade-offs so you walk in clear, or walk away confident.

AI + Strategy

An AI system that knows how you think

We structure your context, decisions, and thinking patterns into a system that compounds. Your AI stops starting from scratch and starts building on everything you already know.

The Partnership

What you get

Strategic Sparring

  • 4 hours per month of 1:1 sessions
  • Flexible scheduling: 4x1hr, 2x2hr, or any combination
  • Direct WhatsApp access (weekdays)
  • Session summaries with key insights
  • Clarity on what AND how to execute

What to expect

  • Honest, direct feedback (we don't sugarcoat)
  • Challenge when we think you're wrong
  • Pattern recognition from 25+ years in the field
  • Help navigating complexity, not just strategy
  • A peer relationship, not consultant/client

Need your team in the room? Strategic Sessions are facilitated deep-dives for you and your key people. We design and facilitate a focused session around a specific challenge. You leave with clarity and an action plan. Tell us about your challenge →

Compatibility

Fit check

Who this is for

  • Leaders at inflection points. You're facing a transition, a major decision, or a period of uncertainty.
  • Founders navigating complexity. Building something new is hard. Having a thinking partner makes it easier.
  • Executives who want a peer, not an advisor. You're tired of consultants who don't understand your reality.
  • People who value being challenged over being validated. You want someone who'll tell you when you're wrong.

Who this isn't for

  • People looking for someone to tell them the answer. We help you find your own answers, not hand you ours.
  • Anyone expecting 24/7 availability. We're a thinking partner, not on call staff.
  • Leaders who want validation, not challenge. If you want someone to agree with you, we're not a fit.
  • Organizations needing team training. For teams, see AI Activation or AI Acceleration.
Lived Experience

Your Sparring Partner

Gustavo da Cunha Pimenta
Founder Story

Meet Gus

Most leaders need a thinking partner, not a cheerleader. Someone who can handle complexity without simplifying it away. Someone who's been in boardrooms and backstreets and knows both worlds matter.

Gus has spent years advising companies and mentoring leaders through the moments that shift everything: the pivots, the hard calls, the decisions you can't walk back. He's as at ease helping executives craft bold strategies as he is supporting young people chasing second chances.

He boxed for five years. Sparring taught him more than any strategy deck ever could. You can't see your own blind spots. You need someone across from you who cares enough to point them out. That's the partnership he offers.

Track Record

What people say

"His insights have been extremely useful to challenge our vision and scale up strategy. He's always been a great listener, an honest and transparent professional."

Matthieu Douziech
Matthieu Douziech
Founding Partner at Harpoon

"His insights, based on an extremely clear way of thinking, really help me in setting a course of action for my company and my life in general."

Pedro Andrade
Pedro Andrade
Forbes 30 Under 30

"For me, it's a no-brainer: Thinking about hiring his company? Go. Looking for advice/mentorship? Go."

Pedro Oliveira
Pedro Oliveira
CEO at Talent Protocol
Our Approach

Why this works

We've been in the room.

We've seen how leaders think when stakes are high. We bring that perspective, not as consultants, but as peers who've been through it.

We give you tough love

Honest feedback that others hold back. Not harsh, just direct. Because you need clarity, not comfort.

We ask powerful questions

That challenge your assumptions. We tell you when we think you're wrong.

We share what we've seen work

And what we've seen fail. When we recognize a pattern, we tell you.

We help you figure out how to actually do it

Not just what to do. Strategy is easy. Execution is where it gets real.

Investment

Choose your corner

Test the Waters

Single Round

500 EUR

one-time session

  • 90-minute deep dive
  • Come with one challenge
  • Leave with clarity
  • No commitment
Ongoing Partnership

Strategic Sparring

1,000 EUR

per month, month to month

  • 4 hours/month of 1:1 sessions
  • Flexible scheduling
  • WhatsApp access (weekdays)
  • Session reports
For Your Team

Strategic Sessions

3,000+ EUR

per session, case by case

  • Up to 6 participants
  • 2 hours to half day
  • Designed and facilitated
  • Clear outputs and action plan
Get in Touch Talk to the Founder

Limited to 3 to 4 ongoing clients at a time.

Questions

Common questions

What does "strategic sparring" actually mean?
It means we think through hard problems together. We challenge your assumptions. We share relevant experience. We push back when we think you're wrong.
How is this different from coaching?
Coaches help you find your own answers. We'll challenge your answers and tell you when we think you're heading in the wrong direction.
What's the difference between a Single Round and ongoing sparring?
A Single Round is a 90-minute one-time session. You come with one challenge, we work through it, you leave with clarity. No strings attached. Ongoing sparring is a continuous partnership: regular sessions, WhatsApp access, someone in your corner month after month.
When should I use Strategic Sessions vs regular sparring?
Use Strategic Sessions when you have a specific challenge that needs your team involved: a strategic decision to make, a problem to crack, alignment to build.
What does WhatsApp access mean?
You can reach us weekdays for quick questions or when something comes up that can't wait. We respond within a few hours. It's not 24/7 support. It's having a thinking partner you can reach when you need to.
Let's Talk

Step into the ring

Book a 15-minute call. No pitch, no pressure. Just a quick conversation to see if there's a fit.

Start the conversation

Talk to the founder
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