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Justin Welsh

Justin Welsh is a writer and entrepreneur sharing weekly essays on ambition, money, freedom, and building work that fits your life.

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Latest

Justin’s happenings, collected from public sources, plus their backstory and Starbook, where fans write.

Known for

Overview

Work: Writer, entrepreneur, and digital course creator
First LinkedIn post: October 30, 2018
Going solo: Left startup leadership in 2019 and began with healthcare technology consulting
Breakout: The LinkedIn Playbook grew into The LinkedIn Operating System
Weekly reading: The Saturday Essay, formerly The Saturday Solopreneur

Mini bio

Before the essays.

Justin began in pharmaceutical sales, following the field their father worked in. After several firings, a Craigslist ad sent by their mother led to a Zocdoc sales job in New York. Justin accepted a pay cut and moved to Brooklyn, where that job helped turn a struggling sales career around.

Starting over.

After years in startup leadership, Justin burned out in 2019. A severe panic attack at home in Los Angeles became a turning point. Justin and wife Jennifer left their jobs and moved to the Catskill Mountains. Healthcare technology consulting was the starting point for a different working life.

Finding an audience.

Justin began posting on LinkedIn in 2018. Readers eventually wanted to learn about building an audience as well as software sales. A small LinkedIn Playbook sold on Gumroad in April 2020, then developed into The LinkedIn Operating System. Courses on content and building an internet business followed.

Where the writing is going.

The Saturday Solopreneur began in January 2022 with short weekly business lessons. Today, The Saturday Essay explores ambition, freedom, money, and tradeoffs for more than 200,000 readers. In October 2026, Justin wrote about wanting to become a better writer and self-publish a book.

Creditschronological, newest first

Courses

2024The Creator MBACreator and instructor
2022The Content Operating SystemCreator and instructor
2021The LinkedIn Operating SystemCreator and instructor

Writing

2022The Saturday Solopreneur, now The Saturday EssayFounder and writer

Awards

Favikon creator rankingsJustin shared a ranking of No. 1 worldwide on LinkedIn and No. 1 in business and startups. This is a platform ranking rather than a juried award.

Quotes

Your career doesn’t need to make sense in advance to make sense in hindsight.Justin Welsh, “Illegible careers”

Published October 10, 2026: https://justinwelsh.me/essays/illegible

Trivia

Justin’s mother found the Craigslist ad for the Zocdoc job that brought them to New York.
Justin and Scott Leese started a weekly live show called Thursday Night Sales during the pandemic in 2020.
A failed 2017 YouTube series was called Tales from the SaaS Whiteboard.
A 2022 webinar with Dickie Bush and Nicolas Cole helped spark the idea for The Content Operating System.