Karl Hughes

Karl Hughes is a Chicago-based founder and former startup CTO who builds and acquires niche service businesses. They spent roughly a decade as a software engineer and engineering leader at venture-funded startups in Chicago, most recently as CTO of an education technology company.

When the pandemic hit in 2020 and their previous company was sold, they started freelancing as a technical writer. Demand quickly outgrew what they could handle alone, so they hired writers and editors and turned the work into Draft.dev, a content agency that creates technical articles for developer tools companies. Draft.dev passed $2.5M in revenue in 2022, and in 2026 Karl hired a CEO to run it while they stayed on as an advisor.

In 2023 Karl and partner Manuel Weiss bought The Podcast Consultant, a podcast editing and production company focused on financial and business shows. They have since been rolling up audio and video podcast producers, acquiring Sundial Media and merging in Rise25 in 2026, with a stated goal of exiting around 2030.

Karl writes regularly about scaling, valuing and buying digital service businesses on their blog and newsletter, offers a free Agency Valuation Handbook to subscribers, and hosts the Retained Trust podcast with agency owners.