2025 (Part I) – Reflecting on the year

Note • April 5, 2026

I wrote this back in June 2025 and after a long hiatus I figured it’s finally time to get something back out to my friends on Substack. The cadence of future posts will be guaranteed to be sporadic, but I hope that getting something back out there will help kickstart a bit of momentum for writing more again.

With that being said, please enjoy this post I drafted last year.

It has been a long time since I’ve written on Substack, and I’ve felt that I’ve neglected all of you by not sharing what’s been going on the past couple of months.

The TL:DR; I moved to San Francisco to do Y Combinator, and decided to stay here and build my company, Onlook.

In late December, I left NYC for a trip to Mexico City with friends to celebrate New Years Eve. It’s been a few years since I’ve been there, but it’s always so refreshing to be back in that incredible city. This time I came prepared with plenty of Claritin – I’m not sure if it’s the polution or pollen, but being able to breathe was a big improvement on this trip vs. last time I was there. A few days after New Years, I flew out to SF and began the YC batch.

For those of you that have known me for a long time, you know that I’m a startup guy. I love the ambition and creativity that it takes to build a company, and getting accepted to Y Combinator – THE startup accelerator – is something I’ve wanted since college. But for as much as I have wanted to do the program for the majority of my professional life, joining the program was… extremely unceremonious. Mostly because it was grind time, and the company was something that was going to get built with or without the program, so it was almost like “oh awesome, we’re in YC! That’s great. Ok well let’s get back to work!”

With that being said, January through March was just an absolute blur. The experience deserves its own separate post, but I’ll highlight some of the most memorable moments:

• Taking green tea shots with Garry Tan, Aaron Epstein, and the other YC partners in our crew.

• When YC rented out a game / sports bar and got all of the founders in one place. It was a great opportunity to break the ice with people, and I ended up closing the bar out with two younger founders who ended up becoming our first customers (and friends! Heyo Pablo and Tannen and the guys from Sales Patriot!).

• Doordash CEO Tony Xu speaking genuinely about the experience of building a company. He’s an incredibly authentic leader. It’s inspiring to hear how he operates, and I had no idea he was so intentional about DoorDash’s culture.

• Driving down to YC’s original mountain view location – where I participated in the YC hackathon back in college back in like 2016(?)! – to see Paul Graham and Jessica Livingston talk about startups. And also getting lunch / coffee with Alberto, another founder in our batch, and my cofounder while we were at the YC office. You can feel the ambition oozing in the walls when you step into a place like YC’s original office… it might be the only place in the world that feels that way. It’s just… raw potential. Also, hilariously, during the hackathon I slept on one of the 3 couches they had at the time where they definitely interviewed the top tech founders at the time.

• Getting dinners with Joe, Shav, and Josh – three chaotic Brits who always seemed like they had a crisis going on but were so entertaining to be around.

• Demo Day – waiting to go on-stage with all of the other founders. We’re all lined up, ready to perform for our short 1-slide presentation, and you really feel the weight of the experience. It felt more important than walking for my university graduation, but with much less fanfare.

• Demo Day – post-batch celebratory drinks with batchmates (and another round of shots with Garry and Aaron and the other YC partners). Definitely enjoyed chatting and hyping up the other founders over drinks and pizza outside by the fire pits.

• Getting investment from designers / design-founders I really admire. Oh and also having friends and family invest in the company before anyone else… really appreciate everyone being along for the ride! It’s been really validating to have the support of some of my closest friends. As well as some of my founder friends I met!

They say there’s a bit of a post-YC-slump that happens. I’m not sure if it was exactly a slump for us, as we quickly kicked into gear and started figuring out housing, an office, and more. For the last weeks of April and the first week of May I had the Airbnb to myself (Kiet and I were living and working out of an Airbnb in Potrero Hill, but he went back to Cincinnati to pack up for SF) which has been nice for just having a bit of space, but definitely a bit distracting relative to during the batch when every day was grind time.

I’ve realized I’m someone that really needs a commute in my day – or at least a very explicit separation between work and where I live. I had this issue in New York when I was going stir-crazy in my apartment before I had a WeWork membership.

Cities are meant to not just be lived-in, but experienced, and despite the Airbnb being extremely extremely nice, it is exhausting to be in the same place day-in and day-out.

I went back to NYC for a week and a half in May to pick up the last of my stuff (I find out that it was only 1 box when I arrived to my old apartment LOL), say hi to friends, and see one of my favorite paintings on display at the MET.

The descent into JFK combined with the subway ride into Manhattan, gave me that feeling of coming home. I think there’s something really special about a plane + train combo. Denver has a very similar setup, and taking the train is always something I look forward to, despite its inconveniances. Maybe it’s my early years of train-obsession that adds to the feeling of coming home. Also, it was especially pleasant to see Prat right as I arrived. Thank you Prat, for generously hosting me at your apartment!

In many ways I think the timing of this trip and seeing this specific painting (Wanderer above the Sea of Fog by Caspar David Friedrich) was just what I needed, especially after graduating from YC and being at a new milestone in both my life and career.

It’s hard not to look at this painting and feel like it was made for me.

The man in the painting – painted 200 years ago – is about my height, has red hair, and is looking out over a scene he presumably is going to traverse. I am always thinking about what is ahead, and after making the fourth move to a major city I’ve made in my life, I look at this painting and not only feel like I’m truly an I-moved-to-a-new-city pro, but also like I am overlooking this new phase of life just like the Wanderer: with an air of experience, the tools needed to succeed (see he has a walking stick!), and a courage to embrace what’s in the fog (i.e. the city of San Francisco which, appropriately, is frequently foggy).

It’s hard to overstate how much I miss NYC though.

I will staunchly defend its position as superior to San Francisco in so many dimensions. While I was back, I realized though that NYC is ultra demanding on your energy and attention. It’s probably why the city is so engaging – every time you step outside you’re drenched in stimulation. I still love watching videos of NYC lore on social media. It’s like the center of the universe, and to have been there long enough to recognize the streets and people is something I cherish.

I’ll write a more in-depth argument about the move to SF later in contrast to being in NYC, because this is an especially nuanced situation to critique and there are just really weak arguments tossed around social media about SF vs. NYC. Specifically in the topic of company-building.

The weird thing about startups is that they come pre-loaded with timing expectations. You need to hit a certain metric by a certain time, to then raise the next round, and go on, etc. etc. But you also realize that so much of company building is narrative-control. It’s why people are able to raise huge rounds – they spin or craft a pitch into this brave, intoxicating vision for the world and investors and employees and customers and the media just eat it up.

This year has been a bet on myself, and has come with so much growth. Every week has its own struggles, whether hiring, or building our product, or trying to find an office or apartment. I have experienced so many highs and lows that I’ve found my mood has had to be mastered.

The thing I tell people is when you’re building a company, your emotional oscillations have to be in-control. There seems like very little room for emotion because you can’t really afford to be emotional about things. The highs and lows will wreck you if you can’t sway with the waves.

YC tells everyone to simply “don’t die” and you’ll find success. I believe it too – there are so many external forces that you’re being forced to internalize or interpret, that I can understand why people just throw in the towel after a while. Company building is an assault on your attention and if you can’t control your attention from spiraling into the negatives.

The first half of 2025 has passed at a blistering pace and I think it’s because most days were groundhog day – the weather in San Francisco is essentially the same every time (again, frequently with fog), I’ve almost exhausted all the fast-casual food options within my radius of work and where I live, and this city is just… smaller than NYC.

The first half of 2025 has been incredibly difficult though. I think because it’s been a huge amount of change, and feels like a test of all of the lessons I’ve learned in my 20s.

The main storyline in my life is my company – that goes without saying. Outside of the company though, I’m hopeful that I’ll get to travel at least a few times. I’ve been really craving a beach or some kind of escape, and fear the only way it’s gunna happen is if I just book a flight and go.

We’re going to be growing the team which will be… so so so exciting. We have the office locked-in (it’s an incredibly cool space), we are going to rally a crew of great people, and we’re going to continue to execute.

It feels like there’s an inevitability of so much of what we’re doing. I’m not sure if it’s mindset, or the repulsion my cofounder and I have of the alternative (working somewhere big?), but I am feeling very fortunate that a lot of the bets we’re making are directionally accurate, and I’m grateful to have an unbelievably relentless cofounder. I mean Kiet does not and will not stop working.

As with any city, it takes some time to get situated socially and I’m fortunate to have the YC network as a good starter. I’m hoping to have a bit more regular of a social cadence of events vs other cities I’ve lived in because, after being in NYC and LA where it can take 40ish minutes to get to places, San Francisco feels so so small. Especially with escooters.

I was getting dinner with Andres, a new designer founder friend building item, and he said the thing about San Francisco is that socializing in this city is mostly a result of returning to your regular spots and running into people. And he’s right – I’ve run into other founders out and about, and the serendipity feels on-par if not better-than NYC’s on some occasions.

I’m starting to get settled in my apartment, and have been inspired by the creative genius of Kelly Wearstler (who also writes a Substack!) to really invest in my space. I started with the basics – a couch, bedframe, some side-tables – then recently acquired two brutalist scultpures which I am so stoked about. I get physically excited when I come home and see them, and I’m trying to understand why, but it’s pretty absurd that 1) I have a physical reaction to essentially fancy trash, and 2) I purchased sculptures before I own mugs, a dining table, dining chairs, a rug, a desk, or anything else really. You can see where my priorities are.

Between now and the end of the year I am looking forward to having my space have some more of those essentials and not just art, but I’m taking my time and I’ve enjoyed the creative process. A lot.

Every time I open my laptop I get pulled-into work, so I’m not sure when I’ll write another newsletter (I think my 29 going on 30 article is a safe bet for what’s next. Oh man… 30…), but I did want to ask myself what advice I’d give to my January 2025 self.

I think I’d say to be easy on yourself.

It’s hard enough to build a company, and I think that might just be what happens when you get to a later stage of any pursuit. Fewer people understand your journey, you measure yourself to people who are now at your level, and there will always be a new set of challenges to tackle.

Holding myself to a high bar is important, but if I never clock a “win” or acknowledge how far I’ve come, it can be draining. Luckily, I think I’ve been especially open to the journey of building the company, but I think I could be a lot more chill with myself.

The last thing I have been telling myself recently is along the lines of the pain of change being a sign of personal growth. Someone once mentioned that when you weightlift you should start counting reps once you start feeling the pain… That’s where you really know you’re growing. It feels like there’s been a lot of healthy pain from pushing myself these past few months (and even year, really), and I am certain there will very likely be more to come.

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