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 and 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 "blames others" founder. This person is honest about what's not working but blames other people (economy, investors, team, etc.) instead of taking accountability. As a founder, you are the boss and you have agency at the cost of 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, leading people to trust them and trust that they have a decent shot of succeeding.

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