‘Treat outsourcing agreements like a pre-nup’ – Simon Azzopardi on asking the hard questions

Investor and tech entrepreneur Simon Azzopardi, was told by a founder “we didn’t want to overcomplicate things, we just needed to ship fast.”

At first glance, it seems like a harmless remark. But as Mr Azzopardi expressed on LinkedIn, just six months after that comment the company in question “couldn’t even access their own codebase” – a situation that, understandably, left him furious.

Mr Azzopardi acknowledged that it’s entirely normal for non-technical founders, directors, or leaders to depend on external development teams. The problem that many tend to overlook is that “outsourcing without clear guardrails is a huge risk.”

Comparing this conversation to a “pre-nup”, Mr Azzopardi stressed that whether or not it takes place, can be the difference between a project’s success or failure.

“Cash gets tight. Deadlines slip. The lead dev quits. The outsource agency’s equity structure shifts, changing service quality,” he warned.

He continued: “Suddenly, no one’s sure who owns what – or how to exit cleanly if things aren’t working. Worst case? I’ve seen founders locked in. Held hostage over invoices or disputes that were never talked about at the start. It erodes value. It kills momentum. And it creates stress that no team needs.”

Mr Azzopardi emphasised that asking the uncomfortable questions and confronting potential risks early on isn’t just a sign of maturity – it’s often what saves a project from falling apart down the line.

He went on to highlight some examples of questions that can be asked;

• What happens if we run out of cash?
• What if your team gets pulled to another project?
• What if I raise money and want to bring dev in-house?
• What happens if one of us wants out, for whatever reason?
• What happens to my IP, i.e. the code, the knowledge, the processes we build?

Mr Azzopardi noted that strong business partners don’t avoid tough questions – they face them head-on to achieve clarity.

“If you’re going to build together, plan for the bumps. It’s not about expecting failure. It’s about protecting progress,” he concluded.

Featured Image: LinkedIn