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Sebastian.Gebhardt
Sebastian Gebhardt — Santiago, Chile

I believe Chile can produce world-class retail.And I'm building it.

Read the letterAbout me
Sebastian Gebhardt standing in the Drops store in Santiago
The operator · Drops, Santiago

CEO at Yáneken, a Chilean multi-brand retail group (160+ stores, 10+ brands — Bold, Drops, Hoka, Belsport — 1,500 people), third generation. I build and deploy production AI on the real operation: store operations, pricing, customer decisioning and forecasting. Founder of Andrea. More of an introvert than I probably look — writing comes easier than talking. Here I publish what I'm thinking while operating, building, and observing.

As seen in
La TerceraPulsoDiario FinancieroIdDCMás Que Un PitchStanford GSB
Right now

What's on my mind this month.

A living page. Updated every couple of weeks with what I'm actually doing, reading, and thinking.

Updated
  1. Building

    Yáneken's internal workshop — IRIS validating stores over WhatsApp across 160+ stores, Draper chasing every lead until it converts, and Project Cerebro putting the whole market on the pricing table. What we used to buy as SaaS, we now build.

  2. Operating

    Yáneken — designing the 2026 operating plan: how we keep growing inorganically while consolidating the omnichannel operation and shaving another point off cost-to-serve.

  3. Writing

    El Tío Bold/Drops — the site's series: my side of the stories, paired with what I post on LinkedIn. Writing Nº 002 now: how Bold began, and why betting on sneaker culture in Chile made sense before the market was obvious.

  4. Publishing

    Two whitepapers at Menlo & Oak. One on why citation replaced ranking in AI search, and what a retail operator can actually do about it. The other on marketplace unit economics: if ACOS exceeds contribution margin, you are paying for the privilege of selling. Both full text, no signup.

  5. Reading

    Work in Progress — Michael Eisner. The memoir of the CEO who rebuilt Disney through the '80s and '90s. Fresh off the Jamie Dimon biography: trading banking for the experience business, told from the inside.

  6. Listening

    Acquired — the Costco episode. Four hours. Ten times more useful than any MBA on retail strategy. I re-listen every time I'm about to make a big pricing decision.

  7. Training

    Coming back to triathlon base after a couple of months off for travel. Aiming for Ironman 70.3 Pucón in January.

What I believe

Five beliefs that shape my work.

  1. 01

    Experience is profitability, not cost.

    Bold Vespucio is our most profitable store. Drops grew 2x in sales when we put real design behind it. The data proves it over and over.

  2. 02

    The local operator is Chile's edge.

    Five of the largest retailers on the planet failed here. Not for lack of resources — for underestimating the person who lives inside the market. The real advantage isn't scale — it's context.

  3. 03

    Succession done right is a superpower.

    Third generation. My grandfather Pedro Rishmague opened the first store in 1985 on Paseo Ahumada. I didn't come to destroy what was built — I came to take it to another scale.

  4. 04

    Data beats assumptions. Always.

    The answer is in the customer and in the data — never in intuition. Experimentation wins.

  5. 05

    AI is our generation's biggest profitability lever — if operators lead the adoption.

    Not consultants. Not evangelists. Operators who have managed a P&L and deployed AI inside a real company.

Retail, executed

Experience isn't decoration. It's the lever.

Facades, activations, kiosks, windows — and the content that carries them beyond the mall. Designed and executed in-house. This is what that conviction looks like when it ships: the new Bold at Mallplaza Los Dominicos, the Drops flagship, and the formats around them.

See Yáneken
Bold storefront — yellow grid facade in full sun
Bold · the facade as a brand asset
The operation behind it
stores
160+
brands
10+
people
1,500

Third-generation family retail, run from Santiago — every store an argument that world-class retail can be built from Chile.

Los Dominicos · opening in bloom
Sneakers displayed among cherry blossoms at Bold Los Dominicos
K-pop opening · Los Dominicos
Window display with desert rock installation and mannequins
Windows · seasonal sets
Drops · narrated by SGR
Drops · launch day
CGI · product content
Yellow Bold kiosk with caps, merch and neon hangul
Kiosk · pop-up format
Suspended yellow Bold logo frame over the store floor
The Bold frame · in-store
Built inside

We build the software that runs Yáneken.

I replicated a SaaS in five days and the lesson ran the other way: the weak link is never the tool's horsepower — it's how many people on the team can actually operate it. So a growing share of our critical software is built in-house, with AI, on the channels the team already uses. Three pieces in production:

IRIS160+ stores · 10+ brands

Retail, run from WhatsApp.

A store manager sends a photo or voice note on WhatsApp; AI validates the visual merchandising in seconds, routes the issue to the right team, and answers reviews across 196 Google listings. Every store gets a health score.

View the project
DraperInternal · in production

Not a single lead slips.

Commercial AI agents deployed inside Yáneken: they answer instantly, follow up on WhatsApp until conversion, and the team steers the operation from an in-house console. The category others sell as SaaS, running as an internal capability.

View the project
Project CerebroInternal · in production

Pricing decisions with the market in view.

Competitive pricing intelligence: official prices, competitors, and data quality for three business units — eyewear, Belsport, and Bold — on a single risk table.

View the project

The same thesis as always: data beats assumptions, and the best way to anticipate the future is to build it. What used to take weeks now takes hours. Outside Yáneken, this work is called Menlo & Oak.

Letters

Letters.

Long-form essays on what I learned from inside. Not blog posts — pieces written to last, on family, third generation, retail, and building from Chile. Published only here.

View all letters
Blog

The Retail Brief.

One operator's question, one answer grounded in data and real deployment. Bilingual — here, on LinkedIn, and on Substack.

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Bold's launch campaign at Mallplaza Los Dominicos
Edition 9Aug 26, 2026

K-pop, anime, and a mall where we'd already failed.

The first Bold we opened in Los Dominicos failed. On Saturday we open there again — this time having read what the mall had turned into: the Korean wave, the Callejón Asiático, and why I'd rather compete on differentiation than on price.

Read
The Retail Brief — Ideas Edition
Ideas EditionAug 5, 2026

Double loop, ideas, and why Chile grows at 1.9%.

Chile's central bank put trend growth at 1.9% a year, with total factor productivity contributing just 0.35 points. Argyris, Romer and weak links: why the return isn't in automating what already works, but in finding the task that holds back all the others.

Read
PostJul 30, 2026

Our wholesale clients aren't a channel. They're partners.

With Oakley we brought our wholesale clients together to talk, try product, and look at what's coming — and launched our new B2B portal. Digital transformation isn't about adding technology; it's about removing friction and giving our partners their time back.

Read
Andrea — Society Twin, Focus Groups, Creative Auditor, Bayesian Attribution, Autonomous Agents. One creative jumped from 42 to 72 points.
EssayMay 2026

This is Andrea.

How I built a system that does to marketing what engineering already did to factories. A 100,000-person synthetic society, a creative auditor, focus groups with real group physics, Bayesian attribution. One creative jumped from 42 to 72 in a single iteration. Eight brands in production.

Read
Edition 5May 6, 2026

AI agents need their own rails in LatAm.

Ask Claude to pay your electric bill. It'll write a beautiful plan — and move zero pesos. The problem isn't the model: it's the layer underneath. The missing piece for AI agents to pay something in LatAm, and why no global provider has it. The AgentPay manifesto.

Read
Chile population 2024–2070 — peak 20.6M in 2035, falling to 17M by 2070, fertility 0.92
Special editionApr 15, 2026

0.92 children per woman. Chile's economy has an expiration date.

If you're between 25 and 40 in Chile, you're going to live in a country where half the population doesn't work, taxes double to sustain it, and your pension doesn't exist because nobody's left to fund it. The lowest fertility rate in our history — lower than Japan, lower than South Korea. Why the demographic crisis is an argument for AI agent payment infrastructure.

Read
About
Sebastian Gebhardt smiling at a table on Pixar Pier, Disney California Adventure, with Mickey's Fun Wheel behind
Pixar Pier · Anaheim, California

Operator. Engineer. Third generation.

I grew up inside a family business. My grandfather Pedro Rishmague opened the first store in 1985 on Paseo Ahumada in downtown Santiago. Three generations later I'm CEO at Yáneken — Chile's #2 multi-brand retail group: 160+ stores, 10+ brands, 1,500 people. We're competing to make the Chilean retail experience rival the best in the world.

Before becoming CEO I spent four years as CRO (2018–2022). I led the projects that professionalized Artículos Deportivos Belsport: changed the ERP, stood up ecommerce, built planning and marketing departments from scratch, set up real corporate governance. In 2020, after the first major acquisition, Yáneken was born. We grew EBITDA by 300% and launched store formats recognized as references across Latin America.

I hold an Industrial Engineering degree from PUC and an MBA from Stanford GSB, where I graduated as an Arjay Miller Scholar (top 10%). That combination — engineering, business, and real operations — is the foundation of how I think about retail, AI, and data.

Today, beyond running Yáneken, I'm building Andrea (the simulation marketing was missing) and AgentPay (payment rails for AI agents in LatAm), and advising companies through AI transformation from Menlo & Oak.

Stores operated
160+
Brands in portfolio
10+
People on the team
1,500
Year my grandfather started
1985

Figures as of August 2026.

Trajectory

Yáneken · Stanford GSB · PUC

  1. 2025 — Today
    CEO · Yáneken

    Leading strategic vision and P&L for the full portfolio. Efficiency program + inorganic growth + AI integration across operations.

  2. 2022 — 2024
    MBA, Arjay Miller Scholar · Stanford GSB

    Top 10% of the class. Certificate in Public Management & Social Innovation. Electives in AI, design thinking, and organizational design.

  3. 2018 — 2022
    Chief Revenue Officer · Belsport → Yáneken

    Grew EBITDA by 300%. Led the projects that professionalized the company: ERP, ecommerce, planning, marketing, corporate governance. In 2020, after the first major acquisition, Yáneken was born. Launched 4 store formats recognized as references across Latin America.

  4. 2016 — 2018
    Head of Bold, K-One, Ecommerce, Planning & Marketing · Artículos Deportivos Belsport

    Created Bold from zero — naming, logo, store design, launch. Today Bold Vespucio is the group's most profitable store.

  5. 2011 — 2017
    Industrial Engineering — Max distinction · PUC, Chile

    Top 7% of the class. Winner of the Bain Case Competition 2016 — first Chilean team to win in 10 years. Thesis with LATAM Airlines on operational robustness.

Off the clock
  • Dad to Alexander, husband to Andrea — in that order
  • Disney parks · obsession without apology
  • Full Ironman finisher · the bike is where I think
  • Linkin Park for running · Bad Bunny for everything else
  • Nerd for simulation, engineering, AI
  • Robert Langdon · because the nerd always saves the day
  • F1 Sundays · no exceptions
Moments

Life beyond the P&L.

Without triathlon I wouldn't have the discipline for everything else. The bike is where my ideas sort themselves out and where I make the hardest decisions of the year. Disney is the obsession that keeps reminding me experience matters — every time I go back I understand something new about building a place people want to return to. My wife Andrea, my mom, my triathlon friends, my Stanford classmates — they're the network without which none of the other things mean anything. The stuff below isn't a distraction. It's the source of how I operate, decide, and write.

  • Ironman 70.3 Pucón — bike leg
    Bike · Ironman 70.3 Pucón
  • Cycling in Patagonia with Fireflies helmet
    Fireflies Patagonia · USD 150K for cancer research
  • Triathlon team
    My triathlon crew
  • Disney World with my wife
    Disney World · with Andrea
  • Magic Kingdom castle with fireworks
    Magic Kingdom · obsession
  • With Mathieu van der Poel
    With Mathieu van der Poel
  • Abu Dhabi GP with my mom
    Abu Dhabi GP · with my mom
  • Google Gemini event with Stanford cap
    Google Gemini · Stanford cap
On my bookshelf

What I'm reading and listening to.

Goodreads live. Audible in my ears. Podcasts in rotation. What's shaping how I think this month — from business and operating to neuroscience, longevity, and endurance.

See everything on Goodreads
Goodreads54 libros
Audible · in my ears16 audiobooks
Updated 2026-08-12
Listening· 7
  • 7 Powers — Hamilton Helmer
    7 Powers
    Hamilton Helmer
    3h 16m left
  • Disney Adults
    AJ Wolfe
    3h 52m left
  • Dare to Lead — Brené Brown
    Dare to Lead
    Brené Brown
    7h 30m left
  • The Way of Kings — Brandon Sanderson
    The Way of Kings
    Brandon Sanderson
    40h 2m left
  • Fourth Wing — Rebecca Yarros
    Fourth Wing
    Rebecca Yarros
    17h 50m left
  • Atomic Habits — James Clear
    Atomic Habits
    James Clear
    1h 43m left
  • Outlive
    Peter Attia, Bill Gifford
    7h 52m left
Finished· 3
  • How the Mighty Fall — Jim Collins
    How the Mighty Fall
    Jim Collins
  • Great by Choice — Jim Collins, Morten T. Hansen
    Great by Choice
    Jim Collins, Morten T. Hansen
  • Brain Rules for Baby — John Medina
    Brain Rules for Baby
    John Medina
In the queue· 6
  • Zero to One — Peter Thiel, Blake Masters
    Zero to One
    Peter Thiel, Blake Masters
    4h 50m
  • Trillion Dollar Coach — Eric Schmidt, Jonathan Rosenberg, Alan Eagle
    Trillion Dollar Coach
    Eric Schmidt, Jonathan Rosenberg, Alan Eagle
    5h 40m
  • The Algorithm
    Jon McNeill
    4h 24m
  • The Snowball: Warren Buffett and the Business of Life
    Alice Schroeder
    36h 58m
  • Why We Sleep — Matthew Walker
    Why We Sleep
    Matthew Walker
    13h 52m
  • The Let Them Theory — Mel Robbins
    The Let Them Theory
    Mel Robbins
    10h 38m
Podcasts in rotation13 shows
Updated 2026-08-12
  • Acquired — Ben Gilbert + David Rosenthal
    Acquired
    Ben Gilbert + David Rosenthal

    Historias profundas de las empresas que construyeron el mundo. Cuatro horas por episodio. Sin atajos.

  • Dwarkesh Podcast — Dwarkesh Patel
    Dwarkesh Podcast
    Dwarkesh Patel

    Las mejores conversaciones largas sobre IA y economía. Cada entrevista preparada como tesis doctoral.

  • How I Built This — Guy Raz · NPR
    How I Built This
    Guy Raz · NPR

    Las historias de origen de los founders que dieron forma a la industria moderna.

  • MAS Pitch — Juan Pablo Silva · DF MAS
    MAS Pitch
    Juan Pablo Silva · DF MAS

    Las mejores historias y consejos de los founders chilenos. Fui invitado en el episodio de Bold.

  • Money Talks — La Tercera
    Money Talks
    La Tercera

    Economía, mercados y dinero, en chileno y al grano. Producido por La Tercera.

  • Millions: El arte de invertir — Betterplan
    Millions: El arte de invertir
    Betterplan

    Inversiones y mercados explicados en español, con perspectiva LatAm.

  • Política para Adultos — El Líbero
    Política para Adultos
    El Líbero

    Análisis político chileno con la profundidad histórica que el debate público no tiene.

  • No Negociable — Francisco Pereira
    No Negociable
    Francisco Pereira

    Conversaciones reales sobre negociación: lo que funciona, lo que no, y por qué la mayoría lo está haciendo mal.

  • Alto — hi.vc
    Alto
    hi.vc

    Conversaciones largas con founders y operadores LatAm con ambición global. Curado por hi.vc, los inversionistas detrás de Cornershop.

  • El Garage de Gonzalo — Gonzalo Raggio
    El Garage de Gonzalo
    Gonzalo Raggio

    Conversaciones largas con líderes chilenos sobre lo que de verdad mueve sus decisiones.

  • Huberman Lab — Andrew Huberman · Stanford
    Huberman Lab
    Andrew Huberman · Stanford

    Neurociencia aplicada al sueño, foco, ejercicio y rendimiento. Protocolos basados en evidencia.

  • The Drive — Peter Attia, MD
    The Drive
    Peter Attia, MD

    Longevidad, salud metabólica y entrenamiento. El podcast que acompaña a Outlive en mi librero.

  • The Forward — Lance Armstrong
    The Forward
    Lance Armstrong

    Conversaciones con atletas de resistencia, fundadores y outliers. Resonancia personal: Ironman.

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