more about me

end of a hike with my brother John
end of a hike with my brother John

🐣 hello hello!

This is a page about who I am & how I became that person.

Contents:

👶🏼 My Story

☀️ Career Approach

🌱 Life Philosophy

Questions On My Mind

👶🏼 My Story

I grew up in Oak Park - a nice Chicago suburb wedged between the poor and the rich.

As the youngest, my childhood was filled with learning. My brother Paul taught me hard work and determination. My brother John taught me benevolence & humility. My sister Maureen taught me connection & emotional intelligence. My Mom taught me curiosity & authenticity. And my Dad taught me logical reasoning & gratitude.

Despite that — I was an ultra-competitive, attention-needing, know-it-all shithead from 0-14 years old. I eroded all of the meaningful relationships around me. Friends, family, teachers. It didn’t matter. Through a series of life-changing events, timely books, & honest conversations with myself — I turned it around my freshman year of high school. I began to prioritize personal growth, meaningful connection, fitness, & emotional intelligence. I also lived by the motto “make someone’s day every day”.

Still do.

My high school experience was also filled with tons of diversity. I played sports with rich & poor teammates. I studied with white & black classmates. I partied with nerdy & athletic friends. And I volunteered with Catholic & Atheist neighbors.

It was beautifully holistic.

I graduated with a child-like curiosity to explore and a skillset to connect with anyone. I also left with a sense of duty — a duty to use my privilege and take career bets that positively impact the world.

Why?

Because I met a lot people far smarter than me who simply didn’t have the resources to pursue what they want. They were dealt a bad hand.

I wasn’t. I got really f*cking lucky. As wealthy white American man with a supportive family, I know I was dealt pocket rockets. You better believe I’m going to use that hand to stack the deck for future generations.

That said, let’s recap high school and move onto college.

Some formative high school memories:
Freshman Year
  • Learning mental toughness & becoming authentically weird in cross country.
  • Getting cut from (& humbled by) the basketball team.
    • Lone wolf lifting & skills training for next year’s basketball team
  • Getting destroyed in a 400m track race.
  • Winning Freshmen B baseball team conference
  • Completely changing my mindset by reading How To Win Friends & Influence people & other personal growth stuff like Tony Robbins
  • Rebuilding worn down houses in the most impoverished areas in the US through the Appalachian Service Project (ASP)
  • Learning life-changing insights from a friend’s passing
Sophomore Year
  • More toughness & weirdness in cross country. Ran 3 miles in 18:21!
  • Making the basketball team after getting cut freshman year.
  • Finding my best friends & becoming besties with my siblings.
  • Pitching a 14 strikeout complete game 1-hitter with my Grandpa in the stands
Junior Year
  • Becoming more like roommates / friends with my parents since I was the last sibling left.
  • Throwing parties to connect my grade’s far-too-siloed friend groups.
  • Training hard for baseball & making Varsity
  • Re-establishing great friendships with my current best friends
Senior Year
  • Writing common app essays & reflecting on my high school experience.
  • Voted as varsity baseball captain after being a local junior high team benchwarmer.
  • Becoming a boyfriend for the first time
  • Gaining 55 lbs of muscle & growing 9 inches in 4 years.
  • Learning a lot about mental health & careers from my older siblings
  • Giving the commencement speech to my graduating class.
  • Covid garage workouts with my best friends.

Like 8 of my 10 recent college-educated relatives, I took my talents to UIUC. ILL baby! Long story short, it’s been one hell of a ride. I started in Engineering Undeclared - a program that allowed me to choose from any engineering major. I ultimately decided on Industrial Engineering because it gave me a general engineering skillset & ample time for to pursue outside-the-classroom passions. That available time led me to more formative experiences & personal growth.

My growth through each semester has been distinct. But, they all followed the same directional arrow of holistic growth. All involved my 4 words: authenticity, connection, growth, & exploration. And all have made me more grateful.

A breakdown of each college semester

Freshman Year: 2020-2021

1st semester was filled with engineering classes, biz frat pledgeship, & new friendships via my classes, brother, biz frat, & dorm. My time management abilities skyrocketed & I loved hanging out with a wide variety of people.

Early on in my 2nd semester, I had a seizure and developed lifelong epilepsy. It sucked at first but has been a huge life blessing. It forced me to stop drinking heavily, manage my stress levels, & get good sleep. I grew into a more authentic version of myself while maintaining great habits. Pretty sweet deal if you ask me. Apart from that, I continued on first semester’s trends — more hard technical classes & meaningful friendships. I also dabbled in a consulting club & continued to learn about decision making.

During the summer, I dove deep into emotional intelligence & creativity via books & podcasts. I spent a lot of the summer writing my operating philosophies for life on Chicago’s river walk. I also designed & built a custom CRM architecture to automate away lots of operational work for my mom’s business. Finally, I went on my first hiking trip & fell in love with big nature.

Sophomore Year: 2021-2022

My 3rd semester was consumed with building Illini Blockchain & learning about the blockchain space. I was completely obsessed. It was amazing to feel that level of passion. It also felt great replace my “entrepreneur wannabe” feeling into a real “builder”. Along the way, I managed to maintain good grades, stay in shape, & develop meaningful relationships.

My 4th semester was a series of authentic moments and “pinch me” views. I studied abroad in Madrid and got to see 13 countries & 45 cities. I lived above an awesome private social club & learned a conversational level of Spanish. The experience opened my eyes up to the grandness of the world & the tinyness of myself. I also worked part time for a VC-backed blockchain startup. I wrote down what I did each day and became comfortable with consistent reflection.

That summer, I lived in NYC with 7 strangers. I did growth full-time for the startup & wrote a newsletter on the side.

Junior Year: 2022-2023

My 5th semester was quite the doosy. I grinded full time on Illini Blockchain, wrote my newsletter every Sunday, dated an awesome gal, hosted jam sessions, lifted heavy weights, spent time with friends, dabbled in rock climbing, & took 18 credit hours. I eventually dropped the newsletter to make some more time for my mental & physical health.

My 6th semester was a more balanced doosy. I delegated many Illini Blockchain responsibilites, wrote the occasional essay, hosted weekly jam sessions, met tons of student founders, got in great shape, did my first sales job, traveled to Eastern Europe, made some new besties, & took a chill class schedule.

The following summer, I lived in NYC while interning for Deloitte. I properly explored NYC, made tons of friends, wrote essays, read books & blogs, listened to podcasts, ran cold email campaigns, lived with 7 new strangers, went on runs for the first time in years, lifted heavy weights, & stayed present as much as possible.

Senior Year: 2023-2024

More living & growing.

Some formative college memories:
Freshman Year
  • Business frat pledgship and all of the memories and time-management skills that come with it.
  • Salt Lake City ski trip with my brother & his friends
  • Smoky mountains Christmas with my family
  • Organizing a 80 person bar crawl for my dorm hall. Partaking in many other shenanigans.
  • Countless new beautiful friendships
  • Getting epilepsy, being told I’d never be able to get buzzed or drunk again, & it becoming the most rewarding moment in my life.
  • Helping my Mom grow her business.
  • Writing essays on my life philosophy along the Chicago river walk.
  • A trip to Maine with my good friends & some strangers.
Sophomore Year
  • Going deep down the web3 rabbithole.
  • Building Illini Blockchain from nothing into a premier student org on campus.
  • Getting on Twitter
  • Falling in love for the first time.
  • Skiing with my brother John & his friends in Salt Lake City.
  • Studying abroad in Madrid. Countless pinch me moments: Crying from laughter with my roommates. Easter mass with the Pope. Soccer with teenagers off the Amalfi Coast. Hiking to Canary Island villages. Paragliding in Switzerland. Pubs in Ireland. Orange throwing in Sevilla. Pastries in Lake Como. Gyros in Greek islands. Beach volleyball in Barcelona. Workout at the Olympic Stadium in Athens. Hiking in Austria. Springfest in Munich. Kayaking in Croatia. Driving around Tuscan vineyards. Dancing in Madrid. Living w/ 75 year old strangers in Nice after a 5 minute conversation. That’s not even the half of it.
  • Writing over 200k words of reflection.
  • Working on the growth at a VC backed startup & living in NYC.
  • Hiking mountains in Colorado w/ my family.
Junior Year
  • Scaling Illini Blockchain from 25 → 50 members.
  • Interviewing people I had no business talking to.
  • Flown out to Lisbon for conference.
  • Creating a vibrant intellectually curious community through jam sessions.
  • Planting seeds for UIUC’s founder / builder / creator community.
  • Giving back to AKPsi through mentorship, essays, & presentations
  • Turning Twitter friends into IRL friends.
  • Inspiring my friends to build cool shit. Recorded some cool podcasts w/ them.
  • Attending a weekend founder retreat with UMich killers.
  • Eastern Europe trip with my boys.
  • Dancing in classes, at bars, & during my showers.
  • Writing 150k words of reflection. Writing a few banger essays too.
  • Getting dream jobs off Twitter.
  • Living in NYC again (this time with more money, in better location, & the access of a 21 yr old)

To be clear, I am not a golden goose who can do no wrong. I’ve still got lots of growing to do. I know very little about how the world works. And I am barely starting to understand what makes me tick. That said, I know a lot more than I did a few years ago.

Now, where will these experiences lead me to in my career? I don’t totally know. Nor do I want to know. I’m confident I’m on the right path. But to me, medium term plans are dangerous. I want to think in decades & take action in days. And ideally, the things I do now lead to unpredictable outcomes. That said, I still have a few hypotheses on what my post-grad life may look like…

☀️ Career Approach

Generally, I’d like to become 3 things: (1) A “thinker” who improves many peoples lives through teaching. (2) A badass business builder who works with great people. (3) A person with the internal awareness and financial flexibility to change their life approach (if needed).

My ideal lifestyle
  • Living out my 4 values: authenticity, connection, growth, & exploration
  • In top 1% of health & happiness
  • Challenging, intellectually stimulating work done on my terms.
  • In a job that feels like play to me & work to others.
  • Contributing to a 100x positive future in humanity.
  • Consistently “amped up” by my professional and personal projects
  • Operating in my zone of genius
  • Zone of Genius
    image
  • Be in spaces with some of the most brilliant, optimistic, and high-agency people alive today.
  • Morning free to read, write, & think
  • At least 1 active creative/personal project always
  • Control 90% of my schedule
  • Lots of sunshine & time outside
  • Ability to live & work anywhere
  • Lots of local & global adventures w/ friends, family, & strangers
  • Consistently clear headed & present
  • A handful of deep intimate relationships.
  • Many other meaningful friendships around the globe.
  • Surrounded by positive, ambitious, & authentic people
  • Give back & help others grow
  • Eat an “80% clean” diet
  • Financial assets that fund this lifestyle indefinitely

As of now, I know I’m good at 4 things: (1) Connecting with people. (2) Explaining complex ideas. (3) Getting operational shit done. (4) Learning fast.

And I know I care about 3 things in my first job: (1) Building relationships with great people. (2) Learning a lot about how to run great businesses. (3) Being in a culture where it is fun to come to work.

I could see myself thriving in a chief of staff / sales type of role working for a Series A-B startup or an entrepreneur I admire. Probably based in San Francisco or NYC. And ideally building the future of education, wellness, community, climate, blockchain, or investing.

Other cool post-grad outcomes

To be clear, these are just hypotheses on jobs that could help me go post-economic & move the world forward. Another opportunity may come my way that doesn’t look anything like these — if it makes me say “hell yea!”, I’ll do it. Gotta leave room for serendipity.

  1. A startup with killer, proven founding team (ideally post-PMF)
  2. A media company at intersection of tech / startups
  3. A high-growth business where I can apprentice the owner / founder.
  4. Big company (good brand name) + side projects
  5. Traveling the world with a super low burn rate
    1. Live in a car, WorkAway programs, cheap country, remote job, etc
  6. Running my own business

During that time, I also hope to make a good chunk of change, build assets that cashflow, and keep my burn rate low. I think that will help me live a flexibile life where I have the space to go on side quests of life, take sabbaticals, and honestly evaluate if I’m still on my authentic path.

Then, I’ll use that time & experience to pursue my noble mission. I want to tackle a problem that, if solved, can 100x the future of humanity. I’ve only got 3-5 shots on goal to punch my dent in the universe. So I want to go big. For what it’s worth, I’m also actively questioning if “big” is good. I could be wrong about what I really want. That said..

I’m talking re-creating Golden Age Athens, providing universal basic everything (food, water, shelter, healthcare, education, economic freedom), quantifying physical & mental health to build proactive and precise healthcare systems, becoming an interplanetary species, having personalized AI assistants to outsource all bullshit tasks, reversing climate change, living off of sustainable energy, & installing high speed trains. PS: I wrote an essay on this.

Now, I know that’s a lot to ask for. But I think I can pull it off by spending my time doing 3 things: (1) honing in on a rare and valuable skillset, (2) building leverage, & (3) pursuing asymmetric opportunities.

(1) Skillset

I like to think of this as my “skill portfolio”. Similar to a stock portfolio, each bet serves a specific purpose for the overall portfolio.

  • Meta Skills: learning, executing, & decision making
    • the most important skills in professional life (always improving these)
    • Why Decision Making Matters

      Decision making are like a lever.

      If you have make good decisions (ex: pick the right thing to work on, pick the right people to work with, pick the right place to live), you don’t have to be that hardworking or crazy smart.

      But if you make poor decisions, no amount of hard work or intelligence can get you out of that.

      Build systems to help you improve at decision making. Wisdom > intelligence.

  • Core Skills: building genuine relationships & translating complex ideas
    • these align with my natural strengths & feel like play to me
  • Multiplying Skills: sales, writing, meditation/clarity, focus, leadership, speaking, storytelling, content creation, & marketing
    • these enhance my meta and/or core skills
  • Differentiating Skills: automation, coding, 2nd language, computer science, statistics, math, physics
    • these combine with my core skills and make my skillset rare & valuable

(More on skillset building here.)

(2) Leverage

Leverage is one of those things I learned about and simply couldn’t unsee. It’s the secret currency of professional success.

In short, leverage determines how much output you get for your input. The more you have, the easier it is to do the things you want to do.

As someone who’s cares about impact & freedom, I want a lot of it!

Here’s the types of leverage I’m building, and how I’m building it:

  • People: forming genuine IRL & URL relationships with high-potential & high-integrity people, convincing people to work on my projects with me
  • Digital Media: growing my newsletter, writing evergreen tweets & essays, growing my Twitter / LinkedIn reach
  • Tools: these help me learn & execute better (ex: Notion, ChatGPT, Zapier)
  • Products/Companies: Illini Blockchain

(Learn more about leverage here)

(3) Asymmetric Opportunities

I’m gunning for a pretty asymmetric outcome (early-ish financial freedom + meaningful lifelong career). So, I need to bet on opportunities with asymmetric outcomes. If they go well, I win big! And if I win big, I’m more likely to gain control over my time!

  • Projects: writing in public, Illini Blockchain, Jam Session Community, UIUC Founder Community
  • Apprenticeships: sales for Cyber Patterns & Third Wall Creative
  • Companies: coming soon
  • Random: going to events, providing space for serendipity, cold outreach to people I admire

If you’re working something cool, hit me up!

(More on asymmetric opportunities here.)

At the end of the day, spending time doing the bare minimum at a soulless, clock-in clock-out big corporation is not for me. I want to build meaningful things with long-term, positive-sum, high-energy people. Whether those things come in the form of product, company, community, content, or experiences… we’ll see!

Right now — I’m just pursuing my genuine intellectual curiosity, meeting awesome people, and enjoying the ride!

Ideas & principles that guide my professional decisions
  • Learn through doing. Have a bias for action.
  • Pursue Ikigai
  • Ikigai
    image
  • Define success for yourself. Then pursue it.
  • I'd like my reputation to be “talk to that guy and you'll leave energized, thinking about something new. Good things will happen, and it'll generally cost you nothing.”
  • Don’t be the best, be the only.
    • Be in top 20% of 3+ skills.
  • Be so good they can’t ignore you. Expertise > passion
    • Valuable expertise → freedom + positive reinforcement + (possibly) passion
  • When recruiting for jobs… (source)
    • Overweight: network, culture / leadership, market growth, firm growth, location, firm brand, exit optionality, decision making & applicable learning
    • Underweight: role, compensation
  • Build magnets for talent (ex: newsletter or hosting events). At the beginning, they have very little strength. As things compound, so does the strength of the magnet. However, the magnet can weaken with lack of use.
  • Be the person who organizes stuff.
  • So the highest +EV decision you can make as a young, ambitious person is to move to the absolute GEOGRAPHIC CENTER of your field.
  • Work in your overlap of what's genuinely interesting to you, skills you have (or could easily possess), and opportunities that present themselves. Every job you take...should get you incrementally closer to the absolute intersection of those three things.
  • Don't optimize for the additional $ especially early in your career.
  • Great work = creativity + impact + control
  • Learn to sell. Learn to build. If you can do both, you’ll be unstoppable.
  • Build leverage.
    • Leverage = tools + products + people + capital + skills + experience
    • Equity and ownership are the only tickets to financial freedom
  • Build specific knowledge
    • Specific knowledge = apprenticeships + genuine intellectual curiosity + passion
    • Something you know that the world can’t easily outsource / replace
  • Embrace accountability. Take risks under your name.
  • Good things come to those who write (& teach) what they learn for anyone to see.
  • Projects that can’t fail: meet cool people + learn helpful skills
  • Pursue (asymmetric) opportunities.
    • It’s either “hell yes!” or “no.”
  • Build a portfolio of work. You have to do the work before you get the job.
  • Create genuine relationships. Network = net worth
  • Play long-term, positive sum games with high-integrity, high-growth people
    • Long-term → compounding interest. Positive sum → everyone wins. High-integrity → duh. High-growth → exciting future
  • Define your anti-goals. Then avoid them.
  • To get ahead in a company, all that matters is whether the decision maker likes you. Also, stay off the org chart and report to multiple people.
Other things I’m doing to increase the odds of a great career

In 10 seconds:

  • meeting folks aligned with my values & pursuits
  • building skills that make companies more money
  • keeping up with emerging tech trends to spot future markets
  • creating a portfolio of work
  • building a learning engine & systems to keep it going for decades
  • figuring out what my trillion dollar skillset is
  • balling on a budget
  • internalizing the fundamentals so I can tackle anything (philosophy, economics, psychology / persuasion, politics, mathematics, spirituality / religion, writing, evolution)

In 10 minutes:

Resources that formed my professional approach
Career arcs I take inspiration from

Common themes: built cool shit, crazy life experiences, startups, flexible work for travel, dope network, investor / advisor, share their knowledge, & breadth / depth of knowledge

Tim Ferriss: successful founder w/ awesome network → pro tango dancer + pro martial arts + multi-lingual → great investor + advisor → shares knowledge thru pod & writing → always learning & growing

Steph Smith: indie hacker → 10x startup employee → big media influence → a16z pod → always sharing, experimenting, & building

Julian Shapiro: successful founder → hacker + marketer → startup investor & growth advisor → awesome writer

Andrew Finn: successful founder → buy, hold, & operate SMBs → cool friends

Sam Parr: successful founder → fit + community builder + awesome pod

Shaan Puri: serial entrepreneur → shares knowledge thru pod & blog → angel invests → always experiment & has fun

Ben Gilbert: VC + awesome tech podcast storyteller

David Rosenthal: angel investor + awesome tech podcast storyteller

Chris Sacca: lawyer → successful investor & advisor → awesome network → lives by lakes & mountains → investing in shit that matters → quit the rat race, lots of crazy ultra-race experiences, has good head on shoulders

Joe Rogan: comedian + martial artist + hunter + sports commentator + awesome podcast + awesome network → intertwine the shit he loves with his work

Matthew McConaughey: regular joe → famous actor → philanthropist → wrestled African villagers + swam in Amazon + played the bongos + lived in an RV → authentic, mindful, Alchemist-type approach to life

Jesse Itzler: record label owner + producer + artist → private jet company founder → lived with Goggins + lived with monks + 100 mile races → chased discomfort, awesome wife / family, & shared knowledge

Packy McCormick: combined his love of technology x startups x writing into a beautiful investment fund

Josh Elman: led growth at a ton of dope tech startups

🌱 Life Philosophy

Many people spend most of their time doing things they don’t really enjoy for reasons they can’t articulate. We all work too much, fall into mimetic traps, do bullshit jobs and all kinds of other busy-work type stuff.

Personally, I’m terrified of unconsciously drifting through an inauthentic life. So, I read. I reflect. I listen to smart people. And I try to be present as much as possible.

I also surround myself with friends who define success for themselves, grab the universe by the balls, and make their dream a reality. I highly recommend.

❔Questions On My Mind

Big Questions On Life & Society

Who’s having the most fun?

How can I better listen to the wisdom of my body & emotions?

What ancient texts (from religions & philosophies) can teach me about life?

How can I build a meaningful career that gives me leverage in the future?

What was the secret sauce behind Golden Age Athens, Renaissance Florence, Enlightenment Age Philadelphia, and Early 2000s Silicon Valley?

Where is my thinking irrational or unclear enough that it’s hurting my quality of life?

How can I be ambitious and high-agency without stunting my personal relationships?

What stories am I telling myself that are bullshit? What is my real end goal with X action/belief?

Where am I copying others that I don’t want to be or shouldn’t be?

What impactful ideas can I share with my communities and eventually the world?

For the things I want to get better at, have I been deliberately practicing or just going through the motions?

Do my current typical actions bring me closer to or further from my idealized self?

Reflection Questions That Bring Clarity

Am I closer to freedom?

What did I ship this week?

Is my calendar optimized for flow?

Where am I trying to be too clever?

Does my calendar reflect my priorities?

Was I going too fast, too slow, or just right?

What 20% of actions drove 80% of results?

What’s giving me energy? What’s dulling me?

Can I intentionally slow down to move faster?

What am I putting off? What if I just did it now?

Did I let other people dictate how I spent my time?

Am I calm? Am I fit? If not, what's in place to change that?

What can I remove, digital or physical, to improve coherence?

Am I sticking to the schedule, or am I letting life get in the way?

What’s the real goal here? Is there a better way to accomplish it?

What are my strategies for this org/goal? What habits do I have that represent those strategies?