Certain Decisions Are Worth Someone Else's Scar Tissue

Founders ask me why they'd bring on an advisor instead of just hiring more staff and figuring it out live. Because certain inflection points are worth far more from someone who's already been through them than from someone learning it on your dime.

Five moments where I've seen an outside advisor completely change the outcome:

1. Purpose and vision. A CEO is usually too close to see what the company actually stands for.

2. Board management. Someone who's sat in that room before can help you pick the right members and run a meeting that produces decisions, not just updates.

3. Company and category positioning. Most founders are too close to their own product to see the bigger market story. The right person helps you position not just a product, but an entire category (read Play Bigger).

4. Crisis management. How you handle the first 48 hours often matters more than the crisis itself, exactly when founders are least equipped to think clearly.

5. Mergers, acquisitions, and market exit. The moments with the least room for a rookie mistake.

I'd add plenty more: hiring and comp, fundraising strategy, hard firing decisions, budgeting after a raise, planning, product roadmapping, vendor selection, customer pitches.

A good advisor isn't just there for the big moments. They're the one asking what happened to that idea you mentioned three weeks ago, or suggesting you add a zero to your thinking. Planning is worthless without execution, and a trusted advisor is often the one holding you to it.

Which of these do you have coming up? In my experience, that's the moment to bring someone in... not after.