How do you overcome common venture capital challenges?

This is so aptly said. Finding the right set of investors for the future growth of your company can make or break the company. There have been innumerable examples of network-effects being amplified due to a right sectoral fit of VC investors. The vision alignment will fairly fall in place once you have the right fit of investors alongside in the company.

This is absolutely the hardest matching game! Probably is quite similar to dating. You will find who are looking for probably won't be interested in you or what you're doing. The secret is to think in the shoe of the other party, what is their perfect investment, startup or matching founder? Woking backwards to see if you are satisfying their needs. It is like thinking about what you can offer first, or working hard and growing fast and eventually becoming what they are looking for.

It's beyond dating, more like going steady, even getting married. It's important to differentiate between stated (intended) vision, values, and goals of the fund / company vs. personal orientation and horizon of the individuals (principal investors). Talk to other firms/founders the VC has invested: what are the principal investors' like when the going gets tough? tough but fair and supportive, or quick to externalize responsibility and look to cut their losses. how passionate and committed are the principal investors' to building real companies, vs. timing the entry and exit of the investments. founders also need to know yourself well - what really motivates you, who brings out the best from you?

Founders should consider that the eventual exiting valuation outcome is far more important than the highest valuation in the current round. Raising at too high of a valuation is a risk that the Company may not grow into that lofty valuation. And if taking money from a less reputable firm, that risk compounds as there are fewer investors interested in leading flat or down rounds. Who you take money from and their track records should be part of the calculation when determining fair terms.

This is a significant point to keep in mind, both for founders and investors alike. For future investors can shy away from projects, however promising they might be, where founders have been diluted to an extent (i.e. they hold less than 50% of the shares, pre series A). Founders who set out to raise funds must seek investors who are long-term thinkers, with whom they can plan ahead for the future rounds.

This calls for an importance balance between confidence and humility, and the ability to hold your own sense of what you/your company's worth lightly. This will allow you to judge offers and terms more objectively, and not let emotions dominate - both the high "wow someone thinks I am worth that much", and the low "what if there is no other offer, I better take this."

In our experience working with Founders, Owners, and CEOs, unrealistic expectations abound, and are the toughest to manage. But manage them FOC must, by keeping coming back to it, share the facts, discuss the underlying assumptions and beliefs, and gently confront sometimes the emotions and wishful thinking driving these expectations.

Thinking about the unspoken rules. Don't listen to what people say, look what they do. Even for VCs, looking at what is great about their portfolio