A costly mistake with a Facebook Ads 'expert' taught the speaker to never outsource a function without first developing a foundational understanding of it. This knowledge is crucial for asking the right questions, spotting red flags, and properly vetting external help, preventing expensive errors.

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When leading a function outside your expertise (e.g., a comms leader managing BDRs), success depends on hiring a great functional leader. Your role becomes asking them to explain concepts simply until you understand, trusting their expertise, and advocating for their needs, rather than trying to become the expert yourself.

Before hiring for a critical function, founders should do the job themselves, even if they aren't experts. The goal isn't mastery, but to deeply understand the role's challenges. This experience is crucial for setting a high hiring bar and being able to accurately assess if a candidate will truly up-level the team.

Marketing leaders often fail when hiring for functions they don't deeply understand. Success comes when you've done the job yourself first, like Capsule's marketing lead who ran events before hiring a specialist. This first-hand experience allows you to know precisely what "good" looks like and evaluate candidates effectively.

It is almost always faster and better to do a task yourself once. However, this is a trap. The "cardinal sin" is failing to invest the extra upfront effort to delegate and train someone, which unlocks compounded time savings and prevents you from ever having to do that task again.

Before hiring a full-time specialist (e.g., for events or SEO), the existing team should first test and prove the channel's effectiveness. Hiring a dedicated owner for an unproven function is a high-risk bet. Validating the strategy first ensures the new hire is set up for success and the investment is justified.

To learn a critical skill like ad buying, don't just hire an agency to do the work. Instead, pay them their full fee but mandate that all work is done on live calls where you control the computer mouse. They direct you, you execute, and you learn the skill firsthand.

Jane Wurwand wishes she'd known sooner that no external expert understands your business, customers, or emotional drivers better than you do. While you can hire for experience, the founder's intimate knowledge is irreplaceable. For a long time, she felt like she was "winging it" before realizing this truth.

If your team lacks development expertise, don't hire an agency to build a complex SaaS. Instead, build a simpler product that aligns with your skills, such as a no-code app or a small utility. This approach avoids unmanageable technical debt and agency dependency.

To build an effective AI product, founders should first perform the service manually. This direct interaction reveals nuanced user needs, providing an essential blueprint for designing AI that successfully replaces the human process and avoids building a tool that misses the mark.