One lesson founders consistently make is to listen and trust investors. Most investors fantasize about being founders but they do not have the balls to take any risk. The only risk they take is with the money of others, which they take a cut from. They call themselves “builders”, “operators” but the only reason they can sip a $7 latte at Blue Bottle in Palo Alto on University Avenue lies in the success of their parents and the trust fund built for them.
Investors will not have any personal consequence for their mistake. You will.
The only exception to this rule is investors who are previous founders or operators at an early stage (and better if they are repeated founders). Such investors know exactly what it takes to build a company, how much suffering you will go through. That’s why people like Peter Thiel built Founders Fund. Thiel attracted founders that wanted to avoid the traditional VC nonsense. It made Founders Fund known for having some of the highest-returning early funds in VC history.
Always operate with zero trust for investors and do not listen to their advice. Their incentive is to grow a fund, return capital and attract more investors to the next fund. An investor will dump you like a middle-age man dumps his loving, hard-working wife for a good-looking 20-years old during his midlife crisis. The reason is simple: they are not working for you and may have stronger incentives to be against you. This is the exact same why your board (where your lead investors) is probably going to fire you.
And when Khosla called out publicly a founder from one of his portfolio company (Factory) despite having invested in it, it was totally predictable - he was protecting a bigger investment in a competitor (Cognition) that is likely going to make more returns.
Take investors for what they are: capital allocators. They raise capital, distribute it and hope for the best returns.
The relationship is very transactional:
as an investor, you give money to put more fuel into the rocketship
as a founder, you should grow your business and increase shareholder value
Investors are capital allocators, not your friend.
And always remember that money is just a tool to build a business. In the early days, you barely need it and using too much of it is likely to do more harm than good.