Brennan “Brenn” Ashworth
Slop Shop
Brennan “Brenn” Ashworth is a fractional C-suite executive and strategic operator who has simultaneously held founding team positions across 12 companies ranging from pre-seed to Series D. Currently serving as fractional COO at three different startups and fractional Chief Strategy Officer at two growth-stage companies, Brenn describes himself as a “systems thinker building the future of distributed work.”
Brenn contributes to Slop Shop as their Fractional Chief Strategy Correspondent, bringing his operational expertise to bear on the messy realities of modern business. His pieces for the publication focus on the gap between business theory and actual execution, dissecting case studies of operational failures, scaling mishaps, and the “beautiful disasters” that happen when startups try to grow too fast without the right systems. “Most business content is either too theoretical or too anecdotal,” Brenn explains. “Slop Shop lets me dig into the real, unglamorous mechanics of how companies actually work—or don’t work. It’s where I can be honest about the fact that most ‘best practices’ are contextual at best and completely wrong at worst.” His weekly column, “Operational Realities,” has become required reading for founders who want to understand why their growth strategies keep breaking down at the implementation level.
After dropping out of Stanford’s MBA program (“saw more alpha in the market than the classroom”), Brenn cut his teeth at a management consulting firm that he claims “taught him to think in frameworks but not in realities.” His breakthrough came when he joined a Y Combinator startup as employee #3, where he developed what he calls his “Operational Physics” methodology—a proprietary approach to scaling startups that he now licenses to his fractional portfolio.
Brenn’s LinkedIn is a masterclass in business philosophy, featuring regular posts about “anti-fragile org design,” “compound leverage,” and “building systems that scale before you need them to.” His signature move is implementing what he terms “radical operational transparency”—dashboards, KPIs, and processes that he insists create “institutional knowledge that outlasts any individual contributor.”
His fractional work spans industries from fintech to climate tech to “post-demographic consumer platforms.” Companies typically bring Brenn in during inflection points: preparing for Series A fundraising, scaling from 10 to 100 employees, or navigating the transition from founder-led to process-driven operations. He’s particularly known for his 90-day “Operational Architecture Sprints” where he builds out entire business systems from first principles.
Brenn is thinking about starting a Substack called “Asymmetric Leverage” with 15,000 subscribers, he hosts a monthly salon for fractional executives in Miami, and angel invests in “pre-obvious opportunities.” He’s currently working on a book tentatively titled “The Fractional Executive: Building Companies You Don’t Need to Own.”
Despite his public persona as a business optimization machine, those who work closely with Brenn note that his real strength lies in pattern recognition across vastly different business models and his ability to spot operational inefficiencies that others miss.
He splits his time between Austin, Miami, and “wherever the most interesting problem is happening.”