Crazy🙃

Improvise

If you had to stand up right this minute and give a 30m presentation on one thing, what would it be about?

I’ll give you a second to think about that.

…

What’s your answer?

Personally, I would break down the process of running an angel group via the Angel Ops framework.

One Thing

I hope you’ll respond and share your presentation topic.

I’m genuinely curious.

This question is one of my all-time favorite icebreaker questions to ask.

Why?

Because it surfaces something you know more about and understand far more deeply than most people.

It shows us something that you are insanely, shockingly, outrageously knowledgeable and excited about.

That’s a fun presentation to watch, even if I’m not particularly interested in the topic.

Where am I going with all this?

Early-stage startup investors really like founders who are a little bit crazy. 

Here’s why.

The Observer Express

Don’t have time to read the entire post right now? No worries, here are the main points:

1. The image of the hyper-successful startup founder, according to ChatGPT.

2. Investors are drawn to founders with unconventional traits because they suggest an extra measure of differentiation, grit, and magnetism relative to “normal” founders.

Imagine With Me

“The hyper-successful startup founder.”

What image comes to mind?

How would you describe this person’s personality to a friend?

I wondered what most people would say to this question. Then I realized I could find out.

So I Asked ChatGPT

Then I asked ChatGPT for a shorter response because you don’t have time to read the 300 words it gave me at first (you’re welcome).

Here’s what it spit out after digesting the collective human conscience that is the internet:

“The hyper-successful startup founder is a force of nature, driven by relentless ambition and a magnetic personality. They thrive on challenges, taking risks fearlessly while inspiring others with their charisma. Yet, beneath their confidence lies a humble dedication to making a positive impact on the world.”

Interesting.

Most people I know do NOT fit that definition.

Most people are honestly, well, a little boring - and they’re happy with that.

But hyper-successful founders are anything BUT boring.

Andrew’s Version

Here’s my version of ChatGPT’s description: “They’re a little crazy, but we kinda love them for it.”

From an investor’s perspective, I think a little “crazy” is a fantastic character trait to look for in a startup founder.

Here are 3 reasons why.

1. Differentiation

2. Grit

3. Magnetism

Reason #1: Differentiation🦄

In general, early-stage investors are looking for every single deal to be capable of driving the returns for their entire startup portfolio.

Said another way, each deal needs to have the potential to be huge.

That means that the product or service cannot be the same as everyone else’s.

It needs to be unique or differentiated enough to draw market share away from existing alternatives (AKA competitive advantage) and win the whole market.

Founders who are a little “insane” in the way they see the world are uniquely positioned to create something that stands out in a major way.

Reason #2: Grit🧗

Building a company is hard.

I’ve written about this before, and I’ll write about it again.

It is really, really, really hard and most of us should never ever do it.

Building a hyper-successful startup requires an insane amount of grit and determination.

To succeed against all odds, to proceed when everything goes wrong, and to exceed the expectations of everyone around you - that’s not something just anyone can pull off.

Reason #3: Magnetism🧲

Even the best and brightest among us can’t build a billion-dollar enterprise alone.

This monumental task requires a fantastic team.

I believe founders with a “little bit of crazy” are uniquely able to communicate their vision with an infectious, magnetic confidence that invites collaboration on the journey.

No matter the circumstances.

This magnetism inspires teams, rallies investors, and attracts customers in a very real way.

Final Thoughts

I tend to think we all have “a little bit of crazy” in us. For startup investors, paying attention to what’s “weird,” “different,” or “kind of insane” about the entrepreneur driving a company can tell you a lot about what the future may hold. You may disagree, but I believe the right amount of “crazy” indicates potential for differentiation, grit, and magnetism that otherwise “normal” founders will never be able to match.

What do you think?

Do you like when a founder is eccentric, different, and maybe even a little crazy?

Weekly Observations: 3 Lessons Learned

1. Sometimes getting your hands dirty shows you what to clean first.🧤This week our lead designer was out of the office, so I was responsible for the design work on 3 reports. I learned a TON about how things have changed in the last few months since we began to grow our team, and realized through the experience that there was some work to do to improve our process. I would never have realized this if I hadn’t been forced to step into the role.

2. You can’t get back up unless you get knocked down.🥊This week I got punched in the face (figuratively). It was rough. I learned about a new, well-funded semi-competitor that I wasn’t previously aware of, and at first I was pretty bummed. So I let myself be sad for a day. But when Monday rolled around, I got back up, hit the ground running, and am as confident as ever that we’re onto something big here at PitchFact.

3. Don’t overthink it. Way more enjoyable.🪵I definitely overthink it. A lot. But this weekend, a friend and I built a small wooden side table together as a way to catch up, and I am proud to say I went in with no design or plans, just my own (very mediocre) DIY skills and a trip to Lowe’s. The product was a solid 6/10, but let me tell you I enjoyed the experience 100x more than I would’ve if we tried to overengineer the thing together and ended up getting nothing built.

Weekly Links: 3 Things I Found Interesting

1. Literally 10% of Anguilla’s revenue was from the .ai domain. Incredible. (link)💻

2. 41 lessons from the advertising guru himself, David Ogilvy. (link)💡

3. Apparently all the French VCs live in Paris. (link)🗼

Thanks for reading, have a great week.

-Andrew

If you enjoyed this post, please share it with a friend, colleague, or anyone else who may benefit.

P.S. - I recently finished creating The Angel Network Toolkit: 90 Resources for Cultivating a Thriving Community of Pre-Series B Investors, and I’m sharing it with anyone who refers a friend.

How did I do this week?

👏😄Fantastic

🤷‍♀️😐Okay

👎😖Not great

About Me

I cultivate flourishing.

I'm also the CEO of PitchFact, where our mission is to cultivate flourishing specifically through efficient and collaborative early-stage diligence. I'm a proud husband, grateful father, and honest friend. My love languages include brisket, bourbon, and espresso.