It's been 2 years since we sold @teachable for a healthy 9-figure amount

In that time, I've traveled to lots of places, invested & worked with 50+ startups and had a ~lot~ of time to reflect on the journey

Here are all the things I'd do differently if I started over:

1/ Be *very* intentional about culture

For the first few years, until we hit ~30 employees, our culture just worked

The team dynamic was incredible, everyone worked hard and cared deeply - truly, the best years of the startup journey

So I assumed it'd always be that way...

So, we never explicitly codified our culture

We had no values that we were willing to lose people over

And as we scaled... the cracks started showing

Different teams hired differently and had their own culture

By the end, our culture was unrecognizable from where we started

2/ Hire fewer people and pay them more

Headcount is the worst of all vanity metrics

I would fight harder next time to keep the team as small as humanly possible

That also means hiring executives aligned with that vision, who don't derive their self worth from their team size

Related: I'd still spend as much on headcount

Instead of having a larger team, I'd just pay the smaller team much more than we did

And have every employee understand the tradeoff

There were multiple occasions we could not close a key exec because of being excessively frugal

3/ Have less ego about being the CEO

I loved being a founder

And for the first few years, being the CEO is a pretty similar role

But somewhere along the way (year 3/4?), the roles diverge

And it's now clear to me that being the CEO of a somewhat mature company isn't for me

But as a young egotistic person and a first-time founder, I had tons of ego wrapped up in being the "person in charge"

Even though, I did not derive energy from a lot of the B.S. a CEO needs to deal with

And wasn't particularly good at it

Next time, I'll step aside sooner

4/ Only hire people that really value working at a high growth startup

Growth is painful and unnatural

Everything is always breaking

But to a certain type of person, growth is also wildly stimulating and fun in a somewhat perverse way

These people were our best performers

A corollary to measure this is:

If a candidate is debating between joining a tiny, growing startup and very large tech company, they are automatically not a fit

I'm sorry but if you come from a world where 40% y-o-y growth is "fast", it's not a fit for an early startup

5/ Pick an even bigger, more exciting market

At the time, the universe of online courses felt massive

And there have been many $1B+ companies built in the space

But now evaluating Teachable as an investor, I'd candidly say our market size is only moderately interesting at best

This sounds downright delusional outside the Silicon Valley bubble but:

Your probability of a $1B+ exit increases dramatically if you shoot for a $100B+ exit

A disproportionate amount of venture $$ goes to those ideas even with very high mortality rates

And even more importantly:

Audacious ideas in massive markets attract the highest quality of talent

The more expansive the mission, the more appealing it is to a certain type of intelligent, motivated individual who wants to work on hard problems

Fin/

That's all for now

There are many, many more things I'd do differently but this was a start

And at the end of the day, I'm still immensely grateful for the journey

You can do all this right the second time but still never find product-market fit...