Here’s what I wish I knew day 1:
1. Assume you know nothing on founder calls. Staying in a place of complete open-mindedness, without arrogance tainted from prior experience, allows you to see the founder’s brilliance much more clearly, obtain new understanding, and see what may have changed to allow for opportunity today.
2. Ask simple questions. The simpler the better to allow for quicker decisions. Technical, nuanced questions can come later, but often don’t drive decisions.
3. It’s a dance. Meaning, it’s a two-way relationship, not a one-way interview. That doesn’t mean skip your due diligence process, but engage the founder in such a way that both parties are evaluating an aligned fit. Show up to all calls with that framing.
4. A start-up is a founder’s metaphorical baby. Treat the engagement with grace, particularly when declining the opportunity.
5. Find ways to be helpful early if you believe in the opportunity. It was more true 2 years ago than today, but rounds can still get competitive, and the truly helpful investors stand out.
6. A quick no is a gift to founders, especially equipped with feedback.
7. Who the founder is matters more than almost all else (obviously there are table stakes around the business too). Lean on references, understand the founder’s psychology, and design questions to define human potential. Get clear on what traits drive success and with 1st principles design your process.
8. The litmus test of “Would I get a beer with this founder” is lame. Separate likability / personal resonance from the probability of success. Be more open and less judgmental about how a founder should be, look, and speak.
9. Moving fast (but thoughtfully) as an investor is alpha.
10. Getting clear on your “pre-screening” criteria (min criteria to make an investment) to avoid wasting founder’s (and your) time is critical to your operations.
11. Designing a clear process to rapidly intake and evaluate companies will allow you to win competitive opportunities.
12. Integrity is important. Do what you say you will. Follow up promptly. Less talk, more action. Don’t miss calls. If you have to reschedule, notify as far in advance as possible. Reputation is tied to integrity.
13. Listen v closely. Absorb as much detail as possible. People show you who they are, mostly.
14. “Vibes” are underrated. The energy you bring to a call is critical. You often don’t partner with competitive founders by virtue of being a Stanford grad or having some tier 1 VC firm on your resume.
15. Brand is also underrated. Share your mind and show up as you. Founders resonate with your deeply weird and authentic self.
16. Lean on the founder to ask the best questions possible. When addressing risks, clearly state what you’re looking to understand “Help me understand how you will…”. Ask the founder to reframe to a better question / cover anything crucial missed.
