Be Optimistic and Honest
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One of the best parts of being an investor is meeting amazing founders. After hearing hundreds of pitches and reading 300+ investor updates, I've noticed that the best founders are disarmingly honest about what's not working, yet steadfastly optimistic about their ability to succeed .

Optimistic and dishonest
This is the "always crushing it" founder and a lot of people fall into this bucket. They project extreme optimism and that holds them back from being fully honest about the problems. Most startups are failing most of the time and if a founder is only ever talking about success, it starts to breed skepticism about how trustworthy they are.

Pessimistic and honest
This is the "undersells themselves" founder and it's also very common. This is the founder that is honest about the problems but doesn't project enough confidence in their ability to succeed. Startups are hard and if someone doesn't project optimism, you might trust them as a person but not trust their ability to succeed as a founder.

Pessimistic and dishonest
This is the "blame others" founder. This is the person that is honest about what's not working but blames other people or the market or whatever instead of taking accountability. As a founder, you are the boss and you have agency, at the cost of literally everything being your responsibility.

Optimistic and honest
This is the perfect combo and it's rare. These founders directly and proactively admit to problems and in the next breath they project a high degree of confidence in their ability to solve them. These people say, "we're failing but we're going to succeed and here's why" with a straight face, leading people to both trust them and trust that they have a decent shot of succeeding in the end.

One of the best ways to spot an optimistic and honest founder is they ask questions like, "why might this fail?" and they are genuinely interested in the answer, showing that they are more interested in succeeding than convincing you they will succeed. They also tend to put revenue goals to actuals at the top of their investor updates, sometimes showing zero revenue growth for months. You'd be surprised how rare that is and how tempting it is to bury those metrics or go MIA when things aren't going well.