The Looking Glass: Fundraising, AI and Little Snacks

Tidbits from the past week

Dear Readers,

This is what I hope will be a weekly collection of bite-sized ideas and Q&A from my daily journal. Some of the rawer ones are gated to paid subscribers (thank you for the support! It means a lot and yes, I am writing more because of you :)

If you’d like to buy me a metaphorical cup of coffee every month — I’m here for it!

Now onto this week’s tidbits. (Paid subscribers see 4 more tidbits including one on the role of user research.)

Fundraising

I was asked What’s the best advice you have for fundraising? The question made me pause. There are trillions of tweets and tomes on this topic. Is there really any more uncovered ground?

I suspect the reason this question gets asked so much is because what’s hard about fundraising isn’t the actual fundraising itself. What’s hard is knowing the problem and solution space well enough to have a convincing plan. Successful fundraising comes from knowing your shit, not because you slid in a big TAM number on slide number 8.

It’s hard to break down “know your shit” into a single practical piece of advice. But here’s my attempt: Ask yourself What questions am I hoping investors don’t ask me? (If you don’t know what questions investors are likely to ask, do some more research or ask ChatGPT(.

Make a list of your answers. Be honest. Now stick that list next to your monitor. These questions are a map of your weak spots. They are your insecurities and uncertainties. Take each one as an action item. Go deep and make a study of it. Fortify your plan. Do this until there is no question that you dread, no question that you have not wrestled to peace with.

If you know your shit, the actual fundraising tends to take care of itself.

Onebox

Google got it almost right with the one box paradigm. What they missed is that it feels far more natural to use the one box as a text messaging box than a keyword search box. Same shape, different mental models.

Ephemeral Magic

AI generated art seems magical today, much as how photography must have seemed magical then. What happened to the magic? We pulled out the oldest human trick we know: taking it for granted.

We value what is hard and rare. AI won’t change that; it will only change our tastes.

Gains and losses

I have an obsession with finding the cost to every victory, the gains from every loss.

A wise person once said, If it sounds too good to be true, it probably is and There’s a silver lining in every dark cloud.

I suspect this obsession comes from the same place that made me a designer: a deep respect for intentionality. You must weigh the tradeoffs carefully to make the best decision.

Sounds great, right? Until you examine the costs. I suspect the real wellspring of my intentionality is a mad desire for control.

Put that way, it doesn’t look so wise. Life is uncontrollable, and attempts to deny this lead to plodding decisions and frustrated outcomes.

The kryptonite of intentionality is the unknown unknown, and years of my life will be sacrificed at the altar of this great force.

From the Archives: How To Talk About Yourself in the Best Possible Way

Excepted from the full post. If you’re looking for a new role or thinking about your next chapter, I hope this is useful.

Step 2: Realize that you’re the primary actor in your life and so you should also be its biggest narrator

“But my work speaks for itself!” This was always my excuse whenever people asked me why I never talked about myself. Also: “I value humility!”

Yes, your work says *some* things about you. Certainly if what you say and what you do don’t align, you’re going to lose credibility. But why would you leave the narrative of your life a mystery and ask people to interpret it from what you do? That’s like a teacher asking her students to watch her add fractions on the board in silence as a way to figure out math. If we want to be understood, we need our words to supplement our actions.

Don’t rely on your colleagues or friends to tell your story either. While it’s wonderful when they do, they only know a part of your life. No one else can read your mind and know your passions, your motivations, what you’ve learned, and what your dreams are.

In short: You are the director and star of your own movie. Nobody else thinks as much about you, or should care as much about your career or your aspirations as you do. So don’t rely on others or your actions to do the talking for you. Take charge of your narrative and realize that it’s good for you to talk about yourself.

Step 3: Find your nuggets of “why” and focus your story around those

Even if you’re convinced by now that you should talk about yourself, the question still remains: How do I do so in a way that isn’t icky?

The key here is to avoid the mistake of over-focusing on what you did. Nothing is more snooze-inducing than reciting a factual timeline of your life, your resume, or your achievements. The part that builds connection, that turns your story from a couple of black and white statistics into a colorful film, that adds the spice and herbs to your otherwise bland potatoes, is the passion and personal motivation behind your facts.

If you grew up in Nebraska, how are you shaped by that experience?

If you quit your job in 2018, why did you do that?

Why do you get up in the morning every day and do what you do?

Why do you care about the things you care about?

These questions — your whys — should form the backbone of your story. They’re the details that give someone a sense of who you really are. They’re what make you interesting. If someone decides they like you or relate to you, it’s because of these nuggets.

Often, our whys come from past failures or negative experiences. Maybe you quit your last job because you weren’t successful at it. Maybe you moved here because you were miserable in Nebraska.

Don’t shy away from talking about those struggles, or poking fun at yourself occasionally. You may worry that it makes you look weak or incompetent, but it does the exact opposite. It makes you feel more human, more authentic, and more trustworthy. Ask yourself: would you rather hang out with the person at a cocktail party who tells you everything they’ve ever done is perfect, or the one whose life story has the natural tensions, twists, and ups and downs of a good Star Wars movie?

In short: to tell your story well, help people understand not just what you are, but why you are the way you are. What are your motivations and passions?

Read the rest of the article.