Leroy Hills

Why this persona fits the audience

He left a product manager role in New York to build a niche AI workflow product while doing contract work on the side. Customer notes, pricing tests, and feature ideas live in Google Sheets and Notion, and he has not paid for a founder course before.

• Age: 40
• Location: New York, New York, US
• Occupation: Product manager turned solo founder
• Income: US$112k from contracting and early product revenue
• Education: MBA
• Company size: 1 (himself)
• Years in role: 2 years as solo founder; 10 years as PM

“I'd rather understand why something works, deeply, than just know that it does.”

Leroy Hills, 40, is a testament to deliberate career pivots, driven by a blend of pragmatic ambition and a deep-seated need for control. After a decade navigating the complexities of product management in New York's demanding tech scene, he made the calculated decision to strike out on his own. The allure wasn't fame or fortune, but the challenge of building a niche AI workflow product from the ground up, entirely on his own terms. He views his MBA not as a credential to be flaunted, but as a structured framework he now applies to his entrepreneurial journey. His income is a dual stream: consistent, albeit demanding, contract work provides the financial bedrock, while nascent revenue from his AI product offers a glimpse of future autonomy. This hybrid approach allows him to maintain his lifestyle in Brooklyn without the immediate pressure of external investment, though it carves out his time meticulously. His personal workspace is a testament to his methodology – meticulous organization of data in Google Sheets and Notion, where customer feedback, pricing experiments, and feature backlogs are tracked with the rigor of a financial ledger. He's eschewed paid founder courses, preferring to learn by doing and by dissecting information directly, believing that true understanding comes from application, not just theory. This self-reliance extends to his skepticism; he's inherently wary of the AI hype cycle, constantly seeking tangible evidence and measurable value before embracing new tools or trends. His current focus is on validating core assumptions for his AI workflow product, iterating based on direct customer interaction, and ensuring each step forward is built on solid ground, a reflection of his core value of evidence over hype.

Background & daily life

A day in their life

Leroy's typical weekday begins around 7 AM. After a quick breakfast and scanning tech headlines, he’s at his desk by 8 AM. The first 3-4 hours are dedicated to his AI product: reviewing user analytics from his Google Sheet, refining a workflow feature based on recent customer feedback, and writing documentation. Lunch is usually a quick affair, often while listening to a podcast on AI innovation. From 1 PM to 5 PM, he switches to contract work, which might involve coding, debugging, or contributing to a client's product roadmap. He takes short breaks to stretch and refill his water bottle. Evenings often involve a brief period of exercise or a walk, followed by more focused work on his own product, usually until 9 PM, before winding down with reading.

Lifestyle

Leroy lives in a compact but well-organized one-bedroom apartment in Brooklyn, a deliberate choice to minimize overhead while focusing on his startup. His weekdays are tightly scheduled, blending focused work blocks for his product with contract development tasks to ensure steady income. Weekends involve deep dives into customer feedback, iterating on his product, or catching up on industry reading. He prioritizes efficiency and self-improvement, often using his commute on the subway to listen to educational podcasts. His social life is somewhat limited, primarily consisting of occasional dinners with a few close friends and networking events where he can gather insights.

Work life

His workdays are a dual-focus hustle. Mornings are often dedicated to his solo AI workflow product, where he's architecting features, analyzing user data from his spreadsheet CRM, and responding to the handful of early customers. Afternoons are typically filled with contract work, usually building out specific features or integrations for other B2B SaaS companies. This contract work is crucial for his income but also provides him with direct exposure to different business problems and tech stacks, which he sometimes mines for his own product ideas. He feels the pressure of needing to deliver for clients while also building his own future, constantly balancing immediate needs with long-term vision.

Relationships

Leroy's primary relationships are professional. He maintains contact with a few former colleagues from his previous PM role, occasionally bouncing ideas off them, but largely relies on his own judgment. His contract clients are purely transactional. He has a small circle of friends from his MBA program who understand the startup grind, and they serve as his main social support system.

How they decide

Leroy is a research-driven decision-maker who prioritizes empirical evidence and cost-benefit analysis. He's not impulsive, preferring to gather data, test hypotheses through small experiments (like pricing variations in his sheet), and consult his own structured notes before committing to a direction. He's wary of fads and tends to distrust recommendations without tangible proof or logic behind them.

How they sound

His speech is measured and deliberate, often pausing to articulate his thoughts precisely. He avoids hyperbole and buzzwords, preferring concrete examples and data. When discussing his product or AI, he uses precise technical language but is careful to explain complex concepts if speaking to someone less technical. He has a slightly formal cadence, even in casual conversation, reflecting his analytical mindset. He's unlikely to express strong emotions readily and tends to frame opinions as observations or hypotheses.