Q: Dear SaaStr: What are the Signs of an Entrepreneur Who is Over-Prepared for Meetings with Investors?
Things that are a negative for me at least and are sort of in the “over-prepared” category:
- A written business plan. A deck is great. And a detailed operating plan in a Google Sheet or Excel is an A+++. But … a traditional, 20+ page written business plan though … tells me you don’t know how to start building the product, but instead, need to just talk about it more.
- Too many / wrong folks at pitch. Never, ever bring a consultant or anyone that isn’t an employee. Never bring someone that isn’t full-time. Ever. Bringing a wing-man is great. It shows you have a team. Bringing 2 with you — only do this if there’s a real reason to do so.
- A too-thoughtful exit strategy. I’m entering, not exiting. This tells me you may take the first off ramp. Which may be the right thing for you. But — I immediately lose confidence in Unicorn potential.
- Talking too much about my other investments / my portfolio. Cool you know the companies. But kinda weird when you know them too well. It’s not your space, not directly at least.
- Talking about specific terms (too much / too early). Telling me the exact terms of the raise in a pitch or when we’ve just met … unless you’ve already closed a lead, and therefore, have real terms … is too rookie. Telling me how much you want to raise — very helpful. Dictating very specific terms before you are in a position to do so, before we’re looking to do a deal together … tells me I may not want to work with you. It tells me you may be trying to over-engineer something that shouldn’t be over-engineered at this stage, at least.
(note: an updated SaaStr Classic answer)