Ankur Nagpal 
@ankurnagpal
Sep 23, 2022
8 tweets
I sold my first startup @Teachable 2+ years ago for a life changing amount of money
At the time, I was *convinced* I would not start another business for a long time. Maybe ever?
Yet, two weeks ago, I decided to do it all over again
Here's why 
1 - I was plagued by what could have been
I am *convinced* the real reason founders start a 2nd business is because they realize all. the. stupid. things. they did the first time around
And want a complete do-over
I found myself thinking more & more about what I'd do differently if I did it over
And felt like I owed it to myself to give it another shot
twitter.com/ankurnagpal/st…
Ankur Nagpal @ankurnagpal
Jun 09 22
View on Twitter
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:
2 - Baseline happiness
After stepping out of an operating role, pretty much everything in my life got better
Better sleep, got in the best shape of my life, had a blast traveling the world
& spent a lot of time thinking about what truly makes me happy
twitter.com/ankurnagpal/st…
Ankur Nagpal @ankurnagpal
Dec 30 21
View on Twitter
I’ve found only 4 things that increase my baseline happiness:
1 - Time outside, ideally in nature
2 - Physical activity, preferably rigorous
3 - Meaningful relationships, with lots of play
4 - Work that has purpose, where I have agency
Here’s to more of all four in 2022 
Of the 4 happiness drivers, I started to miss "meaningful work" again
I love investing & will continue to invest in founders & startups for the rest of my life
But simply running a fund on its own didn't check the "meaningful work" box for me
Especially at 33
3 - A problem that mattered to me
I'll share more about what we are building in the coming weeks but
When I sold my business, I went through a crash course in personal finance & realized that I knew nothing about money
Chances are if I felt the way, others did too
I found the same thing talking to other business owners & @Teachable customers
No one teaches you about money & wealth
And this problem is amplified when you don't come from money
It started to feel like we could build something special helping business owners build wealth
Once the idea was planted, I tried to postpone starting the biz as long as I could
I was heading to Portugal to surf for 2 weeks before Labor Day
But when it was time to leave, I realized I was more jazzed about staying back & working on this
And that's when I knew I had to
Missing some tweets in this thread? Or failed to load images or videos? You can try to .