Thread by @Austen

My muse is speaking to me today: Some of the (many) things I got wrong building @bloomtech, in no order whatsoever.

1. I initially underestimated the importance of instructional design and the incredible skillset that being a phenomenal teacher is.

There are millions of talented engineers. The number of talented instructional designers who are also engineers is a tiny fraction of that.

2. I optimized too much for people being debt-free as quickly as possible.

Because this is a value I hold dearly, we started with a high repayment amount for a short period of time.

I think students are generally grateful when it's over, but it was more extreme than many wanted

3. I wrongly assumed that anyone who was willing to work hard enough to learn the skill engineer would work just as hard at getting their first job. (Plus other soft skills)

These are different types of skills with different levels of appeal.

You have to have both.

4. I used to think the only way to reliably motivate people to do the thing that needed to be done was to force them to come to a live class.

That was wrong, though most things people try to motivate are also wrong.

5. Having never worked at a massively successful, super sexy company before, I assumed everyone who had possessed discrete knowledge that would be invaluable.

Turns out a whole lot of people at [super hot company] are simply along for the ride.

6. I used to think enough bad press could kill a company.

I didn't realize how much bad press helps.

7. I learned that being very mission-driven is a two-edged sword.

Everyone at @BloomTech *desperately* wants to help our students. Those who are the most effective in doing so are the best at building systems that help students, and are not always the most empathetic one-on-one.

8. I used to think (to some extent) fundraising could solve almost all problems; that the companies who had raised enough would have time to figure it out.

It's just as often the reverse; companies who have figured it out find it easy to fundraise.

9. I could write books on the importance of focus and clarity.

Maybe one tweet will do.

Doing even one thing incredibly well is really hard. Doing many things well can be necessary, but is orders of magnitude harder.

10. I underestimated how much value a person could create, and that measuring created value is hard. We try, but I'm sure there are people with net worths of $10m from companies where they created billions of dollars of value.

Also people with $10m net worth who created <$0.

11. Tweeting whatever comes to your head at any given moment really makes Twitter easy (and grows an audience quickly), but will definitely get you in trouble sometimes.

Trade-off for everyone to make.

12. People desperately need role models.

13. When you meet [famous person] who you've looked up to your entire life, you discover something very interesting and important:

They're not very different than you.

14. Feeling imposter syndrome is great. If you're not feeling it, you should probably be pushing harder or doing something else.

Even absolute masters are still learning.

15. Very few investors understand your business well enough to give real advice. You will know how well they understand your business intuitively, and if they don't understand it very well only listen to the highest-level advice.

They mean well, they just don't know.

16. It's difficult but important to remember what context people have going into a conversation.

17. Reading, exercising, and sun are still underrated.

18. Your company won't look like every other company, and your job as a founder/CEO won't look like every other founder. Those are built around you, the industry you're in, and the problem you're trying to solve.

19. Often people look at the wrong determinants of success when emulating other companies.

Do you know what made Google so successful? Probably had more to do with a search algorithm that actually worked than the food or camps.

Yet everyone talks about the free food.

20. Almost everyone analyzing a company from the outside has absolutely zero idea what they're talking about.

At best when a random person tries to understand what makes a company work or not they're ~50% correct?

21. You can safely ignore the news. Yes, all of it.

If something is important it will slap you in the face just by existing as a human, and you won't need to make any effort to seek it out (assuming you're not literally living in a cave).

22. The vast majority of people truly mean well and are playing the long game.

A very small number of people aren't.

If you backchannel you'll find those people quickly.

23. Time and loved ones are the only thing that you can't get back.