Will Roman

Crafting bespoke quality boots in small batches @ChisosBoots • Previous startup acquired by @UpholdInc • Doing my best to build a meaningful life.

[Will Roman @willroman]

Lessons I Wish Someone Had Told Me

Tomorrow I'm conversing with students in a university setting. The below lessons are what I'll be sharing with them.

Anything you'd add?

1. All the old cliches are true.

2. Figure out which game you’re playing.
a. If you’re driven to achieve, make sure you actually want the prize.
b. Challenge the traditional metrics of success (prestige) and make your own.

3. Life (and career) are a series of experiments. The linear path is a myth.

4. You will suffer. So make sure you’re suffering for something that matters to you.

5. Get married after age 24, but before age 30. Have kids. Lots of them.

6. Make a small number of high-conviction bets to build wealth.
a. Except for birth, you achieve wealth through Time x Risk x Being Correct
b. Build conviction by writing a thesis based on your unique perspective.

7. Find a wave and ride it.

8. Ultimately, the value you create for others is what matters in most scenarios.
a. You don’t need permission. Credentials don’t matter.
b. Your background/limitations/hardships are not an excuse.

9. Optimism, obsession, and raw horsepower are how things get started.

10. Cohesive teams, the right combination of calmness and urgency, and an unreasonable commitment are how things get finished.

11. It’s easier to do hard things that really matter.

12. Moving quickly is a competitive advantage. So is focus.

13. Being “real” is magnetic to the right people. And repels the wrong ones.

14. Think long term.

15. Relationships are all that matter in the end.

[Will Roman @willroman]

@mattragland Love the family photo, Matt!

[Will Roman @willroman]

@ACC_National This is the dream.

[Will Roman @willroman]

Austin, TX would be a spectacular place to live if a zero tolerance policy on crime and disorder were enforced.

[Nick shirley @nickshirleyy]

@nayibbukele Nayib Bukele has shown the world that a country that locks up criminals, puts law abiding citizens first and incentivizes innovation will thrive.

Bien hecho El Salvador 🙏🏼

[Will Roman @willroman]

@elijahwood @alamodrafthouse The new Austin in a nutshell.

[Declaration of Memes @LibertyCappy]

Never forget who you are, American boy.

[Will Roman @willroman]

@alex_prompter Yeah, but they did not burn the library down. They are making access to the sources more efficient. You can still browse the internet yourself. You can still walk down to the library. Or you can pay for quicker access.

[Will Roman @willroman]

@johnrea Agreed. A shell of its former self. Boom town it may be, but it’s not ideal for families.

[Will Roman @willroman]

@TheJusticeDept The moral panic was manufactured.

Always has been.

[Will Roman @willroman]

@pauljauregui @hasantoxr @bandholz 😎

[Will Roman @willroman]

@walterkirn Thank you for @countyhwy

Never stop

[Will Roman @willroman]

@avidseries A modern cult in all but name, dividing families over allegiance to an unfalsifiable purity test of dogma.

[Will Roman @willroman]

@Rob_ThaBuilder But, racism

[Will Roman @willroman]

@joelrunyon @ImpossibleHQ @braunhagey Your tombstone: “He made no peace with evil.”

[Will Roman @willroman]

@CaseyBHead Thank you, Casey 🫡
Family is everything.

[Will Roman @willroman]

A flowing sense of grounded joy. Rightness.

Married 3/27/26

[Will Roman @willroman]

@SantiagoPliego Appreciate you, sir—keep building up the citadel, we meed men willing to fight for what's right

[Will Roman @willroman]

@pinpulleddrmf @ChisosBoots

[Will Roman @willroman]

@cathrynlavery @joelrunyon YESSS 💪💪🇺🇸🇺🇸🎉🎉

[Will Roman @willroman]

@rb5064 @ChisosBoots short answer: we'll have something similar this fall

have not been able to replicate the whiskey tone in the desired range at a larger scale

[Will Roman @willroman]

@dhh Thank you, DHH. We must bring these facts into the light.