The Idea: In 2013, Adam Ryan was a 9th grade government teacher in Tennessee with a master's degree in workforce education. He'd spent his college years as a campus brand ambassador for Procter & Gamble, HP, and Red Bull - convincing the mayor to shut down streets for a chariot race, throwing events, and learning how to build trust with audiences. After graduation, he realized he couldn't teach business if he'd never actually done business. So he got a job at a media company - and fell in love with the industry. A few years later, a high school friend launched a daily email called The Hustle. Adam joined part-time to sell ads. Four months later, he quit his job. During his honeymoon, he told his wife he was going all in. This was the beginning of Workweek.

The Execution:

• August 2016: Adam joins The Hustle as the first salesperson when the company is doing $10K/month. He helps define the newsletter advertising model that would become industry standard.
• February 2021: The Hustle is acquired by HubSpot for $27 million. Adam leaves as President, a few months before the deal closes.
• November 2021: Adam and former Hustle colleague Becca Sherman launch Workweek with $1.5M in seed funding from LightShed Ventures, Packy McCormick, and Lance Armstrong.
• 2022-2023: Workweek onboards creators across healthcare, HR, ecommerce, fintech, and marketing. Grows to 500,000+ subscribers and $1M+/month in revenue.
• June 2024: Raises $12.5M Series A led by Next Coast Ventures to build niche professional communities. Implied valuation of $60M+.
• 2024: Hits $10.9M in annual revenue with a 50-person team. Launches paid communities at $500-$1,500/year per vertical.

The lesson? Adam didn't start by building a media company. He started by learning how to sell - first energy drinks on campus, then newsletter ads at The Hustle. When he launched Workweek, he knew exactly what creators needed because he'd spent years watching them get underpaid and undersupported. He built the company he wished existed when he was on the other side.