As we've continued to fundraise for our second fund, I've had a few recurring experiences that I thought were worth sharing.

1> Asking how fundraising is going is a terrible question. If it's still going - it's hard. Fundraising is hard. The more I've been asked that question, the more I regret asking anyone the question myself.

I have resolved to ask different questions. Ones that might tell me something about the person I am asking and might create an opportunity to empathize and offer some help or feedback.

What have you adjusted recently in your approach to investors that worked (or tried and failed)?

What is the best question you got asked recently?

What was the hardest and why?

Have you said no to an investor yet?

We should always be learning and adjusting. I have never found fundraising easy or static. You never enter the same river twice, which is also true of conversations with investors.

2> Investor conversations don't move along independently. Progressing with fundraising is like a game of Tetris

Investors (and their preferred check) come in many different sizes, so composing a round requires the right combination of checks.

Investors also play different roles, and securing a lead investor is a critical 'foundation block' that you must focus on first.

But it isn't that simple; you can't just put off the other conversations. Some may need to slow down, and others need to be sped up.

Building to conviction is also a process, and you can find some investors who are more and less compatible with each other to move toward conviction.

Sharing diligence, setting up introductions, and proactively passing on good questions and answers from one investor to the next.

These are all ways to move the round forward and maximise the compatibility and synergy of the many conversations going on at once.

I'd love to hear what you have learned as you've progressed with your fundraising efforts.