Embarrassing confession that I haven't shared publicly until now.
A few years ago, I owed $250,000 in student loans.
Mega thread on:
- Student Loans
- America's debt addiction
- Learning to code
- Bootstrapping a Business
- Asymmetric risks (ex/ #Bitcoin
)
A few years ago, I owed $250,000 in student loans.
Mega thread on:
- Student Loans
- America's debt addiction
- Learning to code
- Bootstrapping a Business
- Asymmetric risks (ex/ #Bitcoin

I felt sick. It was Christmas 2016 and I'd logged in to Navient.
balance: $244,957
daily interest: $51/day
How did this happen?
Easy. Borrow $160k @7.5%. Enroll in income based repayment. Pay what they ask. Continue for 5 yrs. PRESTO - $85k to my tab.
balance: $244,957
daily interest: $51/day

How did this happen?
Easy. Borrow $160k @7.5%. Enroll in income based repayment. Pay what they ask. Continue for 5 yrs. PRESTO - $85k to my tab.
LESSON 1: Don't be on the wrong side of compound interest
SallieMae required $1600/mo just to keep it from growing. I was burning money and missing years of compound returns. When I realized I was imprisoned by them, I got ANGRY enough to do something.
SallieMae required $1600/mo just to keep it from growing. I was burning money and missing years of compound returns. When I realized I was imprisoned by them, I got ANGRY enough to do something.
I used to think I was the lone idiot in this situation.
But then I saw the 2018 student loan stats:
- 1.2 million with over $100k
- 520k with over $200k
Few jobs can even cover interest on these. Asymmetric bets can help you get free and give you hope.
But then I saw the 2018 student loan stats:
- 1.2 million with over $100k
- 520k with over $200k

Few jobs can even cover interest on these. Asymmetric bets can help you get free and give you hope.
LESSON 2: Place asymmetric bets often. They have outsized rewards
.
3 bets paid off and were key to paying off my loans.
Learn to code - 2012
Biotech - 2014
Bitcoin - 2014
Startup - 2015
SaaS Biz - 2016
Join Startup - 2017
New Biz - 2020

3 bets paid off and were key to paying off my loans.







LESSON 3: Coding is a super power.
You can earn a 6-figure income on your terms. Regardless of your pedigree or who you know!
Trading law for code was my best bet to date. "Elite occupations" could benefit as @bitstein noted last year https://twitter.com/bitstein/status/1088590816245878784?s=20
You can earn a 6-figure income on your terms. Regardless of your pedigree or who you know!
Trading law for code was my best bet to date. "Elite occupations" could benefit as @bitstein noted last year https://twitter.com/bitstein/status/1088590816245878784?s=20
Compare the financial prospects of a developer vs. attorney. Also consider $100k debt, 3 yrs opportunity cost, 2nd highest suicide rate.
For context, I was offered $50k as a new attorney in SC back in 2012.
In hindsight, the switch was a no-brainer, BUT...
For context, I was offered $50k as a new attorney in SC back in 2012.
In hindsight, the switch was a no-brainer, BUT...
EVERYONE thought I was crazy. We were broke. Posted a craigslist housing wanted ad & moved. Drove a shuttle while teaching myself to code for 9 months.
I ran into a 60 yr old former colleague who literally said, "your parents must be so disappointed."
I ran into a 60 yr old former colleague who literally said, "your parents must be so disappointed."

LESSON 4: Most people overestimate what they can accomplish in a year and underestimate what they can achieve in a decade.
2013 - landed 1st dev job
2014 - 2x'd income
2017 - 3x'd income
2019 - 2x'd income
2020 - Paid off debt and have 6-figure passive income
2013 - landed 1st dev job
2014 - 2x'd income
2017 - 3x'd income
2019 - 2x'd income
2020 - Paid off debt and have 6-figure passive income
The US is printing trillions and Americans are more addicted to debt than ever. It's critical that you TAKE CONTROL of your financial destiny now.
This is a LONG GAME.
Start a business.
Learn to code.
Read @indiehackers
Read @saifedean's Bitcoin Standard.
This is a LONG GAME.
Start a business.
Learn to code.
Read @indiehackers
Read @saifedean's Bitcoin Standard.
LESSON 5: You will fail continually, but keep pushing forward.
After 2 yrs of working every night and weekend, we failed to raise VC or monetize our product.
We kept pushing and from that failure we bootstrapped a new business to $100k MRR
After 2 yrs of working every night and weekend, we failed to raise VC or monetize our product.
We kept pushing and from that failure we bootstrapped a new business to $100k MRR
LESSON 6: No one is coming to rescue you.
It's important to realize this.
If you're stuck under a mountain of debt it's unlikely that you can count on a trust fund or family money.
You are going to have to sacrifice nights and weekends to get free.
It's important to realize this.
If you're stuck under a mountain of debt it's unlikely that you can count on a trust fund or family money.
You are going to have to sacrifice nights and weekends to get free.
LESSON 7: Free nights and weekends are overrated.
Yes, hustle porn is annoying... But you need to put in the work now to get financially freedom.
The short term sacrifice sucks, but your time investment will reap MASSIVE dividends in a decade.
Yes, hustle porn is annoying... But you need to put in the work now to get financially freedom.
The short term sacrifice sucks, but your time investment will reap MASSIVE dividends in a decade.
LESSON 8: You won't succeed as a lone wolf.
Thanks to biz partners @Fount @bairdhall @robmoore.
Also, grateful to fellow Bitcoiners and colleagues @Casahodl for constantly challenging me.
Lastly, huge thanks to @brittash for believing in me when no one did
Thanks to biz partners @Fount @bairdhall @robmoore.
Also, grateful to fellow Bitcoiners and colleagues @Casahodl for constantly challenging me.
Lastly, huge thanks to @brittash for believing in me when no one did
If any of this stuff interests you, I'm launching a weekly newsletter soon where I'll share regularly tips and growth hacks to building the life you want. https://bootstacker.substack.com/p/coming-soon