Andy Trattner

April 13, 2025

Now

Based in Scottsdale

There is a poker room dangerously close by. I live right on Main St in Old Town, which is one of the most walkable and pleasant neighborhoods in the Phoenix metro. Rent is half of San Fran, but food is similarly costly. Parking is plentiful, traffic is a breeze, Waymos abound.

I broke up with my ex and left Singapore last November. Arrived here in December after Thanksgiving. I'm unspeakably grateful to be back in the States after 4+ years of international roving. I finally have a legit apartment lease and my own bed for the first time since September 2020.

Planting roots and fully settling back here has been a slow process. I recently got a real phone again (sorry everyone for the many numbers), I don't yet have a sofa, I'd love to register as a voter someday, and I still need health insurance. The darn government Marketplace has taken 3+ months to appeal my "special enrollment", even though I just want to pay the full Cigna sticker price out of pocket and go get a checkup...

I moved here blind, having never set foot in Arizona before, purely intending to spend more time with my sister. She's now a couple blocks away. We bump into each other around town. It's great! We had a rocky start to the year but are now slowly building up our siblinghood into a friendship. Every interaction is an opportunity for both of us to practice mindfulness, gratitude, and curiosity together. 

Turns out Phoenix is perfect.


Looking For A Job

In last year's Now post, I expressed a lot of optimism about Shuffle. Then Q3'24 tanked, and we ended up cutting back during a difficult Q4 transition to save the company's profitability. Things have since stabilized and bounced back in the new year, including some crazy good news...about our first customer marriage!

This past week, my cofounder and I processed many learnings.
  • Q1 reflections: we empowered our ops lead to become GM, introduced profit-sharing incentives, and gave the team the last few months to operate on their own... The results are now in.
  • Selling the company: we worked with Baton to list Shuffle and benchmark our market value. We ultimately engaged with 5 potential buyers, including YC's Rocketable, but didn't find any alignment yet.
  • CEO pilot: discovered a friend might suddenly have availability and interest, so he dove deep with our team. This 4-day collab was incredibly energizing for all 9 of us.

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I've been extremely impressed with Austin's velocity moving on from Shuffle to launch his next thing. I've also been impressed with my vacation-mode indulgence, and the lack of conviction I've had while slowly shopping around my network for potential product and ops roles (Ambience, Anthropic, Rippling). I tried being a vibe coder and also a poker streamer. That week of recordings shall never see the light of day.

At this point, it's looking increasingly likely that I'll end up in the driver's seat for Shuffle. I originally joined as 2nd in command when the company had less than $20k of revenue. Austin and I became something more than the sum of our parts, evolving his MVP 30x in less than 18 months to a legit, profitable $600k+ TTM.

The question is: how do we 10x from here?
Is it even possible? And (how) should we hire Andy as CEO?

We both see enormous potential in Shuffle; in the grand scheme of things, it's still very early. And although we burned out for a while, I'm now feeling compelled again—by a combination of what the business needs, a lack of competing options, labor-hour ROI, and good overall fit. I suspect things will clarify and come together soon, one way or another.


Visiting Friends

Travel for me at this stage is a means to social ends rather than personal exploration or tourism. I'm typing this section up unable to sleep on a 48-hour visit to SF for an old college friend's housewarming party. The guest list happens to be incredibly dense with people I really like and haven't seen in forever. I'm also looking forward to an upcoming D.C. trip, again semi-centered on a party and my desire to reconnect with lovely and inspiring humans.

I'm really happy the past few months have already included a bunch of meaningful interactions and visits:
  • Joshua Tree and Death Valley road trip Christmas with a college roommate and his wife. Vegas poker room rate at Wynn, holla.
  • New Years calls and emails from random past people as far back as 2010 in the early Wisconsin high school days. Honored and kinda shocked I was top-of-mind enough for outreach... This blog helped.
  • Los Angeles staying on the couch of some really out-of-touch college pals, co-working and dinner with Jeff, and touring the fire damage with locals (who are also putting me up in SF right now, beautiful guest room in Marina wow). Super energizing overall.
  • A good friend visited Scottsdale for a weekend and slept in my bed with me. Wonderful to host him: went to an improv class together, played pickleball, rode scooters, visited the farmer's market, and toured Taliesin West.
  • Went to Colombia for a friend's cute Latino + Korean wedding, hung out with an Ecuadorian guy I had chatted with years back but never actually met before, saw some of our Shuffle team in Medellín too.
  • Making new friends all over: local chess meetups, my building's residents, poker (e.g. Princess & Rich), dating apps, Shuffle events, etc. 
  • Visited Sedona with a date and had a crazy beautiful hike while it snowed. Ran into an old east coast alumnus acquaintance on the trail bundled up with his newborn, wife, and her mom. My facial detection software is pretty solid.
  • This SF visit officially pulling Austin into the best subgroup of the tech startup crowd (my extended friends and mutuals). I'm endlessly fascinated by "connecting people" and connecting with people... in myriad forms.


Dating

I'm single. Open to meeting people. 

Not really treating it as a "project" or anything that needs much commentary here.

This is probably the best way to have no expectations and be pleasantly surprised—just like I was moving to Scottsdale.

Assuming career gets sorted over the course of this year, setting up my 30s with a healthy trajectory, I think dating (and the nebulous vision of someday starting a family) will naturally become more top-of-mind.


Death and Taxes

As a happy, willing, paying Citizen, my annual United States Government Subscription Fee currently has its own bank account, to the tune of more than $38,000.00 just sitting there right now, today, waiting to be whisked away by debit this coming week. For various reasons, this sum is at least 50% of my felt 2024 take-home income.

Even if it wasn't, I'd still find the bill exorbitant. Probably something between 0% and 20% is reasonable. There might even be ways to go negative and actually earn money—as a happy, willing, productive Citizen. I have one voting share, after all. 

Austin pointed out to me that our pass-thru LLC means we have a much more personal relationship with taxes versus folks who experience auto-withholding on a W2. This resonates, at a furious pitch.

He and I know what that money means, held in our hands, inches from painstakingly careful frugal dollar-by-dollar reinvestment in our business...for our employees, for our customers, etc.

I've been on a W2. I've felt like my tax return numbers were never mine to begin with. I don't remember paying a single lump sum like this, and I've never before felt I owned any of those magic-disappear TurboTax numbers in the first place.

Yet I will make the 3rd largest purchase of my life this coming week, right behind MIT degree and Ecuador land. It will be made in cash, through gritted teeth and streaming steaming expletives, to the IRS and a couple states.

I'll have to forgo the car I would have otherwise bought myself with that money, which I dearly need in Phoenix. Said car would help me be a better and more productive Citizen. Sure I haven't voted except in 2016, for Hillary. But this highway robbery is not my choice at all.

Yet I smile. For the first time in my 29 years on this planet, there exists at least one human being in 2025 who is seriously trying—on my behalf as a Taxpaying Citizen—to reduce my next payment burden. It looks like Q1 resulted in a nice $900 reduction.

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To be clear I have no idea if this statistic is true, but that almost doesn't matter. If you haven't thoroughly examined the above website, please go do so. It's cool. It's a good idea. It might not work. But even at $0.01 saved, I'd still be happy. Whatever the number, it will theoretically add up over the remaining 50 years of my life. I don't do coupons, but this is a gift, so I'm grateful.

On the other hand, I'm also very willing to pay more than 100% of my annual income. For safety, security, the right to freedom, my family and friends' survival, etc. In theory, government is a benevolent monopoly which I support with my life. I made that choice and re-commitment, deliberately and recently, by moving here again. Trump or not, doesn't matter.

My friend once told me the following interesting argument: support government spending regardless of efficiency coefficient, and consider donating 100% of your philanthropy only and always to the U.S. government, because it is the only entity on the planet that does certain important things. So your donation, even though potentially insignificant or woefully inefficient, is at least directionally correct and perfectly differentiated.

This is all very abstract. I'm sure everyone reading this has an opinion on DOGE. Mine is a bit nuanced, beyond the scope of this blog post to fully explicate, and certainly not definitive except in its curiosity to learn more, to understand better. Recently I've been enjoying Ezra's explorations with Santi, Tyler, All-In, and Gavin Newsom. I disagree with him, of course. But I sincerely respect his thought processes and have learned a ton by chewing on and starting to digest his key points.

I suspect Ezra's main issue is precisely that of Strategists vs Operators. Ezra, like me here now (and everyone else in this country), is commenting and "strategizing" about DOGE...meanwhile one dude is actually operating, doing the work, driving America forward a step. That dude, ironically and entertainingly, happens to be Elon.

Results matter. Outcomes matter. Magic Money Computers matter. The forward step could be a dangerous one, but at least it's a step! Thank Galt.

Depending on responses to this post, I'm happy to share more about my personal experiences working for the White House under both Obama and Trump 7-10 years ago, in the Department of Education. One example: it was BLINDINGLY, SHOCKINGLY obvious to me that our little program's $60k/yr line item for a bad Google Forms clone did not produce any more value than a Joker bonfire (21). My other experiences, such as with NASA and defense contractors, were very different. But from where I sit, none of those systems' trajectories meaningfully shifted until January 2025, i.e. now.

Of course, none of this is about the money. Money is simply an incredible tool that organizes humans around ideas. 

What a time to be alive!


Books

"Learning is not supposed to be fun....My audience will decrease. The ones that remain might not even like it. But at least we'll learn something." -@karpathy

I'd love to chat with people about any of the above. Send me reading material too!

I'm so glad I made my list of formative texts way back in 2020. It has held up well and remains surprisingly complete-ish. Tracks with my brain development hitting age 25.

Has anyone else found Atlas Shrugged particularly resonant or dissonant? Not disinteresting, but stimulating. Genuinely open to pros and cons and all critiques. You can guess my passionate position.

Well worth a listen: Narendra Modi, Prime Minister of India - Power, Democracy, War & Peace. Combined with Zelensky, and earlier Milei, Lex Fridman's latest interviews lead to an interesting juxtaposition of international perspectives on history and operating principles. I like the depth and clarity with which we can see other countries' leaders as humans, even if at times we are blinded by (false) proximity to our own.


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About Andy Trattner