Speaking
Keynotes, board sessions, fund offsites, and university programs. I have entered six industries from the outside, and every one of them told me politely that it could not be done by someone like me. That is the material. Every talk ends in something the room can use on Monday. English or Spanish, both native.
Each one is built from something I ran, not something I read. Pick by the room you are filling, not by the title.
Why the builders who matter most arrive without permission. How generalists enter technical industries, earn the trust of specialists, and win. Drawn from the book.
Every AI market is quietly becoming a clinical market. Three lessons from medicine, and the four questions every board should ask an AI proposal. Based on the featured essay.
Companies stall because the organization never evolves as quickly as its opportunity. The enterprise playbook for inflection points: leadership, governance, capital, and commercial model.
What I tell the CEOs I mentor through the Ascend program. The honest mechanics of crossing from founder-led sales to an institution that compounds without you.
Tell me who is in the seats and I will tell you which one to book. Sometimes the answer is none of the four. I will say so.
| Your room | What they actually want | Book this |
|---|---|---|
| Corporate conference or kickoff | Energy, plus a real argument. A reason to question something at their own company on Monday morning. | The Outsider's Advantage |
| Board or investment committee | A screen they can apply to the next AI proposal that lands in front of them, without having to become technical. | Selling AI When the Evidence Bar Is Clinical |
| PE or VC portfolio offsite | Why a portfolio company has been stuck at the same revenue for two years, and what to change first. | A Different Organization Before a Larger One |
| Founder cohort or MBA program | Specifics, not encouragement. What breaks when the founder stops carrying every deal personally. | From $5M to Real Scale |
| Latin American audience | Someone who has raised capital from Lima and Santiago as well as Zurich and New York, speaking in their language. | Any of the four, in Spanish |
The talk gets written in English. The slides go through translation. The same argument arrives with the jokes removed. The room is polite about it, and the Q&A goes quiet, because asking a question in Spanish means waiting for the speaker to catch up.
The Spanish version gets written in Spanish. Different stories, because the ones that land in Lima are not the ones that land in Seattle. Slides in Spanish. Questions in Spanish, answered at speed. I was born in Lima and I have raised capital in both languages. Neither one is the translation.
These endorse the book and the thinking behind the talks, not a specific event. Both are approved for use in programs and promotion.
“I worked with Juan early in his Microsoft career and admired his diverse industry and organizational insights. An Outsider’s Playbook is the product of his career perspective. Juan shares practical frameworks for identifying market shifts, communicating value, building enduring businesses, and leading through uncertainty.”
“In a business landscape obsessed with hyper-specialization, Juan Vegarra delivers a masterclass on turning the generalist mindset into a board-level superpower. Drawing on a career spanning tech, mining, and medtech, Juan demonstrates how an outsider’s lens turns perceived vulnerability into transformative innovation.”
The first email is almost always the same seven questions. Here they are, so you can skip to the date.
Fill this in and it opens a pre-written email in your own mail app. Nothing is sent from this page and nothing is stored here. If the topic and the audience fit, I answer fast.
Prefer to just write? juan@juanvegarra.com · +1.425.246.8496 · One-sheet · Media kit and approved bios