Legacy Voyage

Every year, I interview myself (on my birthday) to reflect on life.

See all birthday interviews here :)

See full show notes here.

Summary

📖 Story: Environment is KING!

🔄 Weekly Round-Up

• 🗣️ Quote: Psychology of deep thinkers
• ❓ Question: What can I learn?
• 🎙️ Podcast: AI Debate on Modern Wisdom
• 📖 Book: Atomic Habits + Tiny Habits
• 👤 Creator: Jay Yang
• 📑 Article: Being a dad and being ambitious

🌟 Dub/Ls Of the Week

• Dub1: Going to Utah + Tonga
• Dub2: Investing in my skills (Jay Yang’s course)
• L1: Posting shorts
• L2: Losing my motivation for work

I went surfing for the fourth time in my life yesterday and got absolutely destroyed. Three wipeouts in a row. Which somehow turned into an episode about how I made the two hardest career decisions I've ever made, and why I stopped calling myself agnostic.

There's also a story about a wave swallowing me whole as a kid and my pants coming off underwater. I share that one for free.

It's the most connected these things have ever felt in my head. Waves, career math, and God.

Episode Summary

• Fourth time surfing ever. California waves are a different animal. Wiped out three times and paddled back out every time.
• Where the fear started. Got swallowed by a massive wave in SoCal as a kid, spun like a washing machine, and my pants and underwear flew off. Caught them and put them back on while holding my breath.
• Failing forward is still the motto. I'll fall 100 more times. That's the point.
• Decision one. Interning in Utah, got a full time offer with a one week deadline, right as I hit the final round with an SF startup. Chose Utah and finished school.
• Decision two. Graduated, all my friends moved to SF, and two weeks after one interview I had an offer out here. Chose SF.
• The framework that got me through both. The four Cs: cash, craft, connections, calling.
• Mapped on two axes. Practical vs purpose, internal vs external. Purpose side matters way more.
• Expanding the surface area of luck. Random yoga sessions. Meeting a guy who sold his company on a random night out. SF is a hub for this.
• The dream self. Picture who you are on your deathbed, then spend your life getting closer without ever arriving. Sisyphus, but on purpose.
• The faith story I've been sitting on. Raised LDS, went hard atheist, swung all the way back, then landed on agnostic in college. Now trying to live a Christian life.
• Being Tongan makes it harder. Religion is family and culture. Saying you didn't serve a mission marks you in a way nobody says out loud.
• "Faith is believing with the evidence and acting as if it's true." Evidence gets you 70% there. The last stretch is a decision.
• The Tinder connection. The founder came back to Northwestern for a fireside and explained the real insight: the thing stopping you from walking up to someone is fear of rejection, so remove it.
• The whole episode in one line. Avoiding failure and pursuing success sound identical, but you live them completely differently. Agnostic was just me avoiding failure. 🎙️

This one's the story of how I got into running. I hated running. Like most Polys, I thought marathon people were insane. Then I flew standby to New Zealand to film my roommate's Ironman and something shifted.

Also got two hot takes in here: networking is overhyped and startups aren't as risky as everyone thinks. And the question I keep coming back to: why not me?

Episode Summary

• Ran 14 miles this morning because my sister ran 13.1 a couple days ago. Gotta one-up everything. That's just how siblings work.
• My roommate's bike box never made it to New Zealand. No bike, no shoes, no wetsuit, no gels. We spent two days scrambling for rentals and he still finished the whole Ironman.
• Mid-race he goes "I'm gonna go do a marathon real quick." Real quick. A marathon.
• Watched people cross that finish line after 15 hours and decided on the spot I was running one. I had never run more than two miles in my life.
• 90 days later I ran from campus to the Chicago Bean and back. No race, no bib. Just picked a day on the calendar and did 26.2.
• "Why not me?" — the motto a Samoan entrepreneur told me he instills in his sons. Been living off that one ever since.
• Got my sister to sign up for her own marathon. She hated running worse than I did. Seeing her cross that finish line had me in tears. 😭
• My bunk buddy is the world record holder for youngest to do six Ironmans on six continents. Same guy will not pay 10 cents for a grocery bag. Grabs produce bags instead. His "hack."
• I did the bunk bed thing for the plot. Not doing it again next year but it was worth it for the story.
• Networking is huge when you know nobody. Once you know enough people it's basically useless. Just go build and people notice.
• Startups aren't risky. Even if the company dies, you walk away with skills you can take anywhere. I've lived this.
• Maybe ten people listen to this. Doing it anyway. Trying to be the Tongan in tech dude, because when I was a kid there was nobody who looked like me in any of this. 🎙️

Season two starts in a bunk bed. Twelve-hour days at a startup, 100K in the bank, and a spark that's gone monochrome for the last two months.

This one's the reset. It's about why I'm recording again, why I'm willing to be cringe on camera, and calling my shot out loud: the first million, documented the whole way.

It's raw. It's a little embarrassing. It's the start of something.

See full show notes here.

Description

I've been putting this off for ages. But here it is... the season 1 finale!!

The full rundown. From a freshman walking out the dining hall with a voice memo, to landing a 6-figure offer in SF with $100k in the bank. Almost four years!

Walking down memory lane:

• My first janky episode
• Backstage door in SLC
• Freshman summer where I fell apart
• The book that gave me permission to believe again
• The Hong Kong trip that changed everything.
• The marathon (then doing it again).
• Leaving my job

All of it.

Summary

• The first voice memo. Walking out of a dining hall freshman year in a winter coat, phone in hand, no plan. Heard a podcast say "imagine if Bezos recorded his journey at 18." Started the thing right there.
• "The first thing you do is always the worst." First episode was rough. Microphone half-cut. Yapping like I knew anything. Didn't matter. No one was listening anyway.
• The Salt Lake backstage moment. Walked through a "Do Not Enter" sign at a Polynesian professional event, found myself in a room with David Tafuna and every cracked Polynesian I'd been DMing for months. Pivotal.
• Freshman year reality check. Couldn't just study more to get the A. Sleep schedule destroyed. Watched all of One Piece in three months at 3x speed. Put on 30 pounds. Coped with binge eating.
• Sophomore summer collapse. The breakup hit me months late. Calling Domino's at 4am. Working till 9am. No idea what I was doing.
• The book that flipped it. Taking Pascal's Wager by Michael Rota. Didn't try to prove God exists, just that you can be rational living a Christian life. That lower bar was everything.
• The $1,000 Jumpstart challenge. Bombed the pitch so hard. They said "your interview was bad but we love your hustle, make $1k by summer and you're in." Convinced 6 Polynesian business owners in Utah to chip in. Got the rest from Coach V.
• Hong Kong, two weeks after meeting her. "Bro, pull up." So I pulled up. Crashed on her couch. One of the most life-changing trips of my life.
• The assumption that broke. Always thought hard upbringings were the only fuel for ambition. Met people in Hong Kong with stable homes who were just as driven. Wait, that's possible?
• New Zealand Iron Man finish line. Watching my buddy cross the line. Started training for a marathon that same day. Two miles in 30 minutes. Three months later I ran the full thing.
• 💔 The Leland goodbye and going to Sphinx. Three interviews in five minutes. Bombed the first round. Did a work trial on Valentine's Weekend. Took the offer.
• The actual takeaway. The money was never the point. The people, the faith, the failing forward — that's what $100k actually bought. Now onto the road to a milli.

Episode Summary

• “I live here now.” Driving around the city and realizing the new apartment in SF is actually home now—one of those surreal life-shift moments.
• Bunk beds were a strategic decision. More space, funnier vibes, and honestly… bunking with your boy just hits different.
• Leaving a company is harder than it sounds. Even after quitting, Slack alerts still triggered the instinct to jump in and fix everything.
• The founder dinner that sparked doubts. Jokes, vibes, and culture made me question if I’d actually made the right decision joining.
• First week reality check. Long hours in the office… but asking the real question: what work actually got done?
• Turns out the first day isn’t the full story. Day one felt rough, but by midweek things started clicking and the rhythm got better.
• Post-grad freedom finally hit. Turning in the last assignment felt like ripping off a four-year weight—school is officially done.
• Health completely fell off. Bad sleep, bad diet, no workouts—realizing I need to rebuild the habits that used to make me feel great.
• A random whale watching trip turned philosophical. Watching families laugh while rich guys sat silently on their phones sparked a deeper question about what actually matters.
• The big realization: money alone isn’t the end goal—family, meaning, and who you build life with probably matter a lot more. 🎙️

This episode is the aftermath. The grind. The goodbye.

You'll hear the voice memos from before I flew to Utah for my last week at Leland, after I'd been binge eating two pints of ice cream and a bag of 7-Eleven donuts every night for two weeks straight. You'll hear me admit I completely fell apart. Lost my routine. Lost my training. Lost my identity a little bit.

Then you'll hear what happened when I showed up to the office and slept there. Worked 8 AM to 2 AM. Did it again. And again. And walked out with the CEO calling me "a true shark."

It's about what happens after you make the big decision. The part nobody talks about. The relapse. The grind. The random college conversations about philosophy and pragmatism that hit different when you're about to leave it all behind. The tiny habits that pull you back from rock bottom.

It's messy. It's exhausted. It's weirdly beautiful.

Summary

• I relapsed hard into binge eating after deciding to leave. Two pints of ice cream and donuts from 7-Eleven. Every. Single. Night.
• Leaving Leland felt like a breakup. Lost a huge part of my identity and didn't know how to process it.
• I almost bailed on the marathon I got my sister to sign up for. Then I listened to my own podcast from a year ago and snapped out of it.
• Tiny habits. That's the whole framework. Give yourself permission to just run around the block instead of doing 10 miles.
• Slept at the office on my last week. My boss literally pulled out sleeping bags at 2 AM. I thought he was joking. He was not.
• We were pulling 15-16 hour days. 8 AM to 2 AM. I thought I knew what work meant. I did not.
• "I've seen a lot of people ramp down and off board. But I've never seen someone sleep at the office on their last week." — my CEO
• Had a wild conversation with classmates about stoicism vs. romanticism. I'm firmly on the pragmatic side. They're about to find out why.
• The HR guy told me straight up: "No one else is gonna look after you more than you." Facts.
• If I could go back, I'd have been more transparent earlier so it didn't feel like a slap in the face. But the way I handled the exit? Best case scenario.
• Done with finals. Done with Leland. Moving to SF tomorrow. Starting a new job Monday. Haven't had time to process any of it.
• There's a non-zero chance I come back. But right now? SF is the move.

This episode is me breaking the news.

I finally pulled the trigger and decided to leave Leland. And honestly… this one hurt. A lot more than I expected.

You’ll hear the raw convos — me calling the team, telling them I’m taking the San Francisco offer, trying to explain that I still love them, that this wasn’t easy, that this might even be the dumbest career move I’ve made.

But I'm leaving Leland for an SF startup (that I only found out abt 2 weeks ago).

It’s exciting. It’s scary. It’s messy. It’s real.

Episode Summary

• “Dude, I absolutely love Leland.” — which is exactly why this decision wrecked me.
• I didn’t fully process how disappointed they’d feel.
• This wasn’t an obvious decision — it was overthinking, second-guessing, and long talks with friends/mentors/family.
• “This could totally be the dumbest career move I’m making.” — but I still said yes.
• Start date is March 9th, I got 2 and a half weeks left at Leland. Time to sprint and not leave anyone hanging.
• I was lowk almost tearing up on the call. Forgot I was even recording.

Episode Summary

• I accidentally made the easiest $10K of my life by sending one text — then did it again.
• I thought I bombed an interview so badly it haunted my runs… and somehow still advanced.
• When opportunities stack up fast, clarity doesn’t — it actually gets louder and messier.
• Living with the boys in SF sounds fun, but a great culture is hard to walk away from.
• Having a high bar matters more than having an offer at all.
• Being the first non-technical hire sounds cool until you realize you’d be learning alone.
• A mentor reminded me: early career is about proximity to great people, not titles.
• Faith, fitness, and focus are slowly pulling me out of my own head.
• Hard moments aren’t setbacks — they’re feedback wrapped as gifts.
• I don’t know exactly where I’m going yet, but I trust that moving forward is enough.