Oprah Winfrey has interviewed over 37,000 people throughout her career.
Oprah says that after each interview, without fail, the person she interviewed asks her, "How'd I do?"
Humans crave feedback. Even the most remarkable among us want validation that we're on the right path. That we're doing well.
Sales reps get feedback from managers. Athletes get feedback from coaches. Pop stars get feedback from TikTok.
In those situations, the feedback is instant. You do the thing, you get feedback, you identify your weakness, and then you improve.
Investing is different.
When you invest in early-stage companies, the cycle from investment to exit will take years.
So how do you know what your weaknesses are, and if you're improving as an investor? How do you get feedback?
Option 1: Work with the company
Once you invest in a company, write down a hypothesis. For example: "I think this team will find scrappy ways to get sh*t done."
Then, work with the team on a project to test your hypothesis.
For example: Offer regular feedback on their marketing emails. Help them with a project. Work with them on their deck.
You'll quickly learn if your hypothesis is true or false.
You may find that the team doesn't have any developers, yet managed to scrap together a website so they could start selling their product.
Or you'll discover they spend tons of time forecasting revenue, but haven't contacted any leads.
Whatever happens, you'll get firsthand information about how a startup can operate – whether that's good or bad – and learn how to recognize that behavior moving forward.
Option 2: Mentor startups
Nowadays every accelerator, incubator, and VC firm has a mentorship program (guilty).
And they're always looking for experienced operators to provide guidance to early-stage startups.
If you do this, you'll get critical insights about the business and team before putting any money into them.
And even if you work with a bunch of companies and decide not to invest in any of them, you'll learn how to spot teams that hustle (and teams that don't).
If you don't take the time to get feedback, you may find yourself making the same mistake over and over again... like consistently investing in teams that are great at pitching but bad at building.