Steve McLeod has spent years building Feature Upvote, a small bootstrapped software company, and along the way became fixated on a question most product literature ignores: how do founders with no product manager, no big budget and no army of researchers actually decide what to build next? He set out to write a book about prioritization frameworks — and discovered almost nobody uses one. This episode is the story of what he found instead, drawn from interviews with ten small, self-funded software companies (including Squadify's own Dan Hammond and Pia Lee) about how they really make product calls under pressure.

The conversation lands on the "Hippo" — Highest Paid Person's Opinion — and the reassuring discovery that it's rarer than founders fear: the companies that lasted were the ones who brought their whole team into the decision, even when the founder ultimately had to call it. Steve walks through the recurring traps (chasing every early customer request until the product buckles under its own clutter), the founders who held their nerve on vision anyway, and the practical habit — ruthlessly deleting your backlog — that keeps decision-making sane as you scale.

Key Themes & Takeaways

• Most software is built by small, bootstrapped teams, yet almost all published advice on feature prioritization assumes you have VC funding and a dedicated product management function.
• In companies under roughly 30 people, a dedicated product manager rarely exists — the founder is the de facto product manager whether or not they were ever trained for the role.
• The feared "Hippo" (highest paid person's opinion) showed up far less than expected: the founders who survived were the ones who genuinely brought their team into the decision before calling it.
• Early customer flattery is dangerous — saying yes to every request in the early days can quietly bury a product in clutter, technical debt and UX debt until the simplicity customers loved disappears.
• Some founders held firm to a narrow product vision under customer pressure and it paid off (Balsamiq's low-fidelity-only stance); others drifted toward enterprise features and had to consciously claw back to their original audience.
• Saying no needs a companion habit: regularly deleting (or archiving) your backlog, since an ever-growing "maybe later" list becomes its own source of stress and false hope
• Co-founder decision-making works best with clear domain ownership and transparency about disagreement — naming the tension openly beats either person quietly overriding the other.

Three Reasons to Listen

• Listen if you're a founder secretly doing product management without ever having the job title for it — Steve makes the case that this isn't a phase to survive, it's exactly where you're supposed to be right now.
• Listen if your backlog has quietly become a graveyard of ideas you'll never build — there's a blunt, freeing argument here for deleting almost all of it.
• Listen if you and a co-founder (or any two people sharing decisions) keep circling the same disagreement — Dan and Pia's own way of working through this at Squadify gets picked apart in detail, including what they actually do when they don't agree.

Notable Quotes

"Hippo stands for the highest paid person's opinion." — Steve McLeod

"Delete almost all of your backlog on an ongoing basis. It's good for you. It's good for your team." — Steve McLeod

"Until your product is a lot bigger, you are the product manager, so embrace that." — Steve McLeod

Steve McLeod's Bio
Steve McLeod is the co-author of "Kill the HiPPO: How small, bootstrapped software companies decide what feature to build next". The book is a collection of interviews with founders of stable, mature, profitable software companies, telling real stories about how founders make hard product decisions.

Steve is a three-time bootstrapped founder and currently CEO of Feature Upvote, a SaaS platform for managing customer feedback.

After experiencing near burnout in his first company, Steve intentionally keeps his running of Feature Upvote low-stress, aiming for modest, manageable growth, so that he can keep mentally healthy while running it.

Originally from New Zealand, Steve has worked in Australia, Germany, the UK, Spain, and more briefly, in Switzerland and France. He now lives in Barcelona, Spain.

Links

• Kill the Hippo
• Feature Upvote