The NCAA Tournament

It’s been an very “chalky” tournament once again this year. That is there is not a lot of upsets and the only “cinderella” is 11 seed Texas who is a large school with many resources and does not fit the bill of small school cinderella.

Of course, NIL and the transfer portal has a large part to do with this.

Since college players can make money, they are more inclined to stay than chase professional opportunities. Most players will make more money in college than they ever will in the rest of their careers playing basketball. So they are staying and also transferring to the big name schools that can afford to pay them.

This does create a situation where the top teams are just simply bigger, better, and deeper than most other teams. There is a clear divide between the top P4 leagues and the rest of the schools that didn’t exist in years past.

Also, Todd Golden who is Florida’s coach also made a great point in that the bigger schools adopted a more old school style of play. That is get bigger players and dominate the boards and paint in order to make them less “upset” proof. Size matters a lot more in college than it does in the pros where everyone is big.

While this may have created a chalky two seasons of the tournament, I do believe that there’s a bit of overreaction right now. What goes around come around. Teams will adapt. Play styles will change. And we will once again get upsets.

For now, it may be best to enjoy the tournament for what it is in the current state. Lots of heavy weights going after each other in very physical games. That’s also as much fun as watching a 13 seed make a deep run. Almost.

Parenthood isn't easy

It was a tough morning at home today. Colin woke up randomly at 5:30am with what appears like a stomach bug. We hoped it was a minor wake up, but had to take him into a bath shortly afterwards. He was inconsolable most of the morning and we decided to keep him home from daycare.

These days are really tough, especially on a Monday. I was already feeling behind from work as we had people in town from this past week, and I didn’t have time over the weekend to catch-up. Sophia did me a solid and let me go into the office in the morning and early afternoon before I we swap mid afternoon.

I’m tired and stressed, and I’ve got a lingering anxiety knowing that Colin is in a tough spot right now. These days aren’t easy, but I know I just need to take a deep breath and know I’ll get through it. Things will get better and some relief is coming at the end of next week with the end of the quarter hopefully.

War

War is hell. My generation had 9/11, Afghanistan, and Iraq. Each situation is horrible in it’s own right, but I do feel fortunate that we did not have a Vietnam like our parents, or a World War like our grandparents generation. There was an impact at home at each of these recent wars, but obviously nothing like a draft where everyday Americans were sent to fight.

Seeing the situation in Iran unfold is scary in it’s own right. I would like to see a regime change, but I do not want to see our country dragged into a brutal war where innocent folks will suffer the worst.

The war is going to start to hit everyday Americans hard soon. While we’re fortunate that Americans likely won’t be dragged to fight on foreign soil, we will soon be fighting an economic battle.

The war just hit another step with Israel attacking the gas fields. The markets have reacted accordingly. Things are unfortunately just beginning.

March Madness

We’re on the verge of one of my favorite sporting events of the year, the NCAA tournament. The storylines, the pageantry, and the unpredictability make this in my opinion one of the most fun times of the year.

Unfortunately, I have not had the opportunity to watch much college basketball this year. With the move to the east coast and a young kid, I’ve prioritized spending time with my family and sleep over sports. But the beauty behind the tournament is that you don’t need to be a mega fan to enjoy it.

Of course, maybe the star of the show is gambling. Estimated predict that over $3.3B will be gambled on this year’s NCAA tournament. According to the American Gambling Association, the number has grown from $2.7 to $3.1 from 2024 and 2025. I’m taking the over on the $3.3B. Given the rise of “prediction markets” and effectively unregulated sports gambling in these apps, I think we’ll see record breaking growth in gambling this year.

I’ll be mostly sitting on the sideline besides maybe tagging on $20 or so with my friends. I stay away from sports gambling as I know how much I’d love it. I’m not afraid about the money lost, but more of the time spent doing this. Maybe when Colin is a bit older.

Crunch time

It’s that time of the quarter where I feel completely overwhelmed and stressed. We’ve got some people in town this week which is a lot of fun, but it does add a lot of meetings to the agenda and throws off my routine completely. Shake-ups are welcome every now and then, but with the end of quarter rush looming, meetings, and a ton of initiatives, it’s a stressful week and period.

My hope is just to grind these next 2.5 weeks to close out strong and build some momentum going into Q2. It’s crunch time for us and we need to deliver. The good news is that these times don’t last forever and I’m already looking forward to some quality time off in April to recharge.

It’s been an exhausting quarter for different reasons compared to the previous quarter. It will all be worthwhile if we keep our heads down and grind things out in these next two and half weeks.

Sleep and recovery

I’ve had my Whoop for almost 3 weeks now and I’ve really been loving having it. I wrote a bit about the accountability aspect. Of course, at some point, I need to see results to make it all worthwhile.

I’m happy to report that I hit my highest sleep performance and recovery scores this morning on my Whoop. While the score is great, obviously the biggest benefit is that I absolutely feel great today. I’m optimistic and happy. I was a better father and husband this morning. I got into the office ready to crush the workday.

It was small changes that led to a big impact. I had been actively prioritizing sleep recently because of my Whoop. Simple things like getting into bed and starting my wind down routine earlier was helpful. Over the weekend, my Whoop told me I had a ton of sleep debt to make up and after a hard workout on Friday, I knew I wanted to use the weekend to catch-up. I stayed in both nights and kept the drinks to a minimal level in order to prioritize sleep. Low and behold, it worked and I feel like I’ve gotten caught up.

I know this is a small win, but I’m proud of myself for getting here. I made it one of my New Year’s goals to focus on my health and sleep, and I feel like a new person today. Of course, this is just one day and my goal is to be better all around so this is just the beginning. But if I continue to prioritize my sleep and recovery, things will slowly start becoming habits.

Democratization of private tech companies

The private tech market is once again the hottest ticket in town. Just this morning, I was fed another ad for a fund being launched by a former democratization of real estate company. This was on top of Robinhood’s venture fund launch last week. And likely many more that I have just completely lost track of.

It’s what people want right now and there are firms gladly to provide it. Unfortunately, I know how this will all end. It’ll be similar to the democratization of real estate craze but multiples worse. While you can lose money on a real estate investment, the prospects of losing a lot more money on tech investments are much higher.

Most retail investors just do not understand just how risky and volatile a tech stock can be. This age of AI has many folks feeling FOMO including myself at times and I’m not smart enough to go out and call this the “top”, but I do know that there is a good amount of risk right now. A lot of retail investors are going to get burned. I can see the articles in a few years now.

Data as accountability

I never got a Whoop or Oura ring in the past. I didn’t think it would benefit me to really confirm what I already know. I figured that I’d know if I was tired from going out the night before or that I worked out hard and my body has a lot of strain. I had actually thought it would have a negative effect, that is I’d feel worse about myself after a night out with friends.

Turns out I was wrong.

I’ve had my Whoop for about 2 weeks and the only reason I got it was that it was free with my Chase Reserve card. My coworkers convinced me that I might as well try it and I agreed.

I’ve really been loving it. The data that I receive on my body is above and beyond what I thought I would be getting. Yes, there’s some confirmation bias — okay I get it, I slept like shit and I know I’m going to feel like shit today and need to take it easy. But the Whoop’s data has propelled me and acted as a bit of an accountability buddy.

For example, I know I’ve been building up a lot of sleep debt the last week. My Whoop tells me that. Of course, I know and could feel that I’m more tired. But seeing that I have an hour of sleep debt allows me to actively try to make that up. I’ve been consciously in bed earlier and earlier ever since having my Whoop.

Yes, it does make me feel worse about myself when I do things that are counterproductive to my health, but I also suppose that is part of why it’s effective. Perhaps I should be resting more and having a few less drinks in order to maximize my sleep.

I can’t believe I’m saying it, but maybe I just took the entry level drug into biohacking like the other tech bros.

Self-inflicted wounds

I had a tough day yesterday which translated into a horrible night of sleep. Despite having a good start to my day with a workout, my brain started spiraling a bit throughout the day. It started with just a negative (and baseless) thought given everything going on, and then my monkey brain decided to cling on and the spiraling followed.

Unfortunately it followed me to bed as well and I spent a few hours just tossing and turning thinking about work. It wasn’t a fun evening and obviously I’m impacted a bit today. I am most frustrated that this was all self-inflicted.

It’s been a stressful couple of months for me with work and the events of the world. It’s one of those periods where seemingly nothing is going out way. It’s felt like we’ve worked incredibly hard on multiple workstreams all to hit a roadblock at the end. Simply put, I’ve been working my ass off and there hasn’t been many results to show. It’s a frustrating place to be when things out of your control impact your direct results.

Of course that’s part of the gig and will continue to happen so I need to do a better job at embracing the downturns. Dwelling in work stress all day does no one any good and I can’t let these things get to me and ruin my day.

Networking

I met a fellow UW alumni at the gym today. He noticed my UW workout shirt and he was also wearing a UW shirt. Despite graduating 42 years apart, we bonded over our school and he invited me to the Dawgs on Wall Street event. It was really nice seeing UW alum in New York. There’s quite a few of us here, but despite being a large school, we do not have as big as representation compared to some of the other schools. A large part of that is that I’d imagine most of our alumni are on the west coast.

It was also a good reminder that I need to do a better job at networking and attending events. It’s something I’ve deprioritized especially over the last year and half given my busy personal life with a kid. But in general, I have done a horrible job going to events and conferences over the years. You just never know who you may meet or what you will learn, and I seldom regret attending these events.

When is it worth it?

On Saturday, Sophia took me to a magic show and we followed it up with a late sushi dinner. We went to see Dan White perform in The Magician. It was an amazing show and my mind is still thinking about how he was able to perform all his tricks. Afterwards, we went to Hasaki in the East Village and chased an epic show with my favorite food, sushi.

It was a great night and maybe the most fun I’ve had since moving back to New York in May. Of course, it was a bit of a special occasion for my birthday and we can’t afford to do something similar every weekend. But it was a really nice reminder that as new parents, we need to live life and go out.

Naturally, we both woke up Sunday exhausted and half asleep. Sophia got a the worst of it because she let me sleep in while she did the morning. Unlike most of my other Sunday hangovers, this one definitely felt different. Yes, I was exhausted but I felt like I actually accomplished something and it was well worth it.

Unfortunately, I can’t say the same about some of the other times. At this point in my life where sleep and rest means I’m a better husband and father, there’s a clear cost-benefit to anything I choose to do socially. Those beers late into the evenings with friends or at home may be worth it, but it may not be. Now that I’m 36, it’s time to really double down on the nights that are worth it, and stop the nights that aren’t.

Grateful to be here for 36 years

I turned 36 today. I feel a bit old, but I am grateful for an amazing life at 36. Unfortunately, not many can say the same and especially today, I am counting my blessings.

I hit the birth lottery and was born in an amazing free country that allowed me to pursue education and my interests in my life. My parents made incredibly sacrifices for me to live the life that I do.

I am surrounded by an amazing wife and son, both of who I love. I have an amazing group of friends that care about me and my wellbeing. I do not know what I did to deserve what I got, but I am grateful and will forever try to contribute to the better of humanity for it.

Admittedly, today was not the most ideal birthdays. I had planned a day of exploring and doing things I love, mostly eating, but I spent a large part of it working and admittedly stressed. Sometimes that’s the way the cookie crumbles. Fortunately, I have an amazing job and I’ll make up for lost time in the future.

It’s not lost on me that age is just a number. At the same time, I am getting older and my time here on earth is limited. Having a kid who just turned 16 months has made me realize that time is moving incredibly fast. The days can be long but the years are short. I should never take my “youth” or my health for granted. My birthday every year is a great reminder that every day here on earth is special.

Change

We’re moving to a larger office within the same coworking space today. I’m excited for the extra space and room to breathe. It was getting incredibly tight here and this new unit will allow us to really grow into it.

Later today, Sophia and I are signing a new lease to move to a new apartment building just a block away. We had wanted to stay, but the rental market has dropped and we got a much better deal in a better unit and building.

Even though we’re upgrading on both fronts, the move is always a bit stressful. Change is something that stresses people out including myself at times. For me, I always think that I need to be upgrading and optimizing at all times of my life. And that always creates FOMO for me. Despite having an amazing apartment that we loved immediately, I had to spend a night or two looking at other buildings to be absolutely sure.

Same thing with the office. Never mind that everyone is upgrading to more space and light solely just by moving, many are probably thinking of which is the best spot in the new office. Change is a good thing and I need to focus on the exciting parts of new experiences and not what I’m missing out on.

When things don't go according to plan

Unfortunately we’re in a business where things don’t go as expected often. A favorite company of mine from years ago in 2020/2021 just announced an acquisition where all common stock is likely to be wiped out.

I was a fan of the business, but more than anything, I loved the people there. They were good folks who cared about their customers and what they were building.

We worked with them in a much different time period. The market was humming and FinTech was the hot space to be in back then. We all know what happened to the broader market, but FinTech was hit especially hard throughout everything.

Undoubtedly this company fell on more difficult times than even other companies during the downturn. It sucks and I feel for the people who worked their asses off to build it. But that’s the game you play in the startup world. Unfortunately the vast majority of companies do not result in any sort of payout for equity.

We do our best to educate people on this. But there’s undoubtedly a bias whenever you work for the company. You are always being fed aspirational information and almost everyone starts counting their chips.

Of course, there’s always shock when things don’t go according to that plan. It’s never a fun situation when your exit leads to a bad financial outcome. The best you can do is temper expectations and make sure you plan for all outcomes, not just the best one.

The mentals of being a parent

I’ve been really trying to find words to describe why parenthood is so hard. Lots of my friends are going through the journey of their first kid soon and it’s been more difficult than I expected to help prep them.

I’m 16 months in now and while I finally feel like I’m on stable footing, it was not an easy journey. The combination of everything really makes things difficult.

Of course the lack of sleep is big especially in the early days. But at least for me in the early days, I was able to power through with just pure adrenaline and knowing that I had to keep a child alive.

For me, things really got hard right around the 6 month mark and that lasted for about 6 months. As I reflect back on it, the biggest challenge for me personally was the mental aspect. All my free time became my kid’s time now. It was never about me for really the first time in my life.

I think it hit me hard at 6 months because that’s really when the adrenaline and the initial excitement of being a father really wore off. The initial excitement of buying him awesome clothes and cuddling with him wore off at the same time that I started to long for more personal time.

In other words, reality set in that this was my life now around that 6 month mark. And it took me almost half the year to really adjust and get used to that new reality. No weekend golf. No going out to dinner. Weekends are for playgrounds and kid activities. It was a big change.

Of course I’m likely in the majority of parents. At the same time, I’d imagine things were a bit harder for me because I was still very much living a different life prior to having a kid than a normal parent. I’d imagine there are many homebody couples that were already staying in the majority of time and going to bed at 10pm, and waking up at 6am.

Optimizing my health

Last week, my Whoop arrived as I took advantage of the Chase Reserve benefit which paid for my first year subscription. My colleagues convinced me to at least try it and see if I could optimize my health a bit better and I was and remain excited to see what could come out of it.

I came into this last weekend at less than 100%. I believe it was allergy related as my wife also experienced the same. Either that or we had yet another minor bug. We both limped into the weekend. For one reason or another, I felt an odd urge to go out on Saturday and be social despite not feeling 100%.

I had a good time with friends in the city. It was nothing crazy. Just a few drinks and watching some basketball. I was home by 11pm which is late, but not scary late. Despite my wife letting me sleep in, Sunday was an absolute brutal day filled with exhaustion and anxiety. Sleep debt wasn’t going to take care of itself, and the drinks on Saturday poured fuel on the fire.

I didn’t need my Whoop to tell me that I had a bad night of sleep and my recovery was low after Saturday night. But seeing some real hard numbers definitely put things in perspective. Contrast that to how I feel today after a 77% recovery score, and it obviously feels night and day.

I probably don’t come close to what the kids are doing nowadays with their bio-hacking or whatever. I still believe that life is a balance and you can’t optimize your health always. But in a constant battle to feel better as I grow older, I’m really loving what this Whoop is telling me.

If it helps me feel better on a more consistent basis, then this is well worth the $360 per year. We’ll see after a few months.

AI related stress

I’ve had lots of moments of feeling like a kid again playing with AI. It reminds me of my younger days when I loved learning about the internet and computer hardware. It was a genuine interest of mine growing up, and I was like a kid in a candy store whenever I could get time to play on the computer.

With how much technology has shifted in the last year or two, I feel like I’m relearning everything again. And it’s fun in many ways, but also stressful.

For one, I am not a kid and I have real adult responsibilities like a job and a kid to take care of. I can’t sit in front of a computer from the time I wake up until the time I go to bed just playing.

Secondly, we’re at the point where you learn AI or you’ll be left behind. I have no intention of being left behind so I’m doing everything I can to get caught up with the limited time I have.

For now, that stress and worry is at a good level. It forces us to take action. Those who don’t have that stress and worry are likely not taking it seriously enough. My biggest thing right now is making sure to force a lot of my work day through AI so I can maximize my time and learn “on the job.” After that, it’s making sure I carve out time every week and parts of my weekend for more exploratory work.

Life is good

Seems like there’s a ton of fear and panic right now in the markets. Fears of AI destroying software companies and potential war in the Middle East will do that to you.

It’s also the part of the year where I’m longing to get the hell out of New York and go on a vacation. The winter has taken it’s toll and I’ve spent most of my free time the last two months at home just being a Dad.

In hindsight, it would’ve been the perfect time to get away from reality for a bit. Alas maybe next year I need to be more ambitious with trips. For now though, I need to remind myself to live a little bit.

Colin is about to be 16 months and he’s at a very great age for Sophia and I to start doing more things. It would be wise of us to enjoy this time as much as possible. Perhaps it’s time to start doing weekly or biweekly date nights. Or maybe take an impromptu weekend trip somewhere.

There’s lots of shit going on in the world right now and it’s easy to fall in the trap of a negative news cycle and forget that life is good. Being a hermit at home with nothing to think about except work during my free times does me no good either.

Humbling

I feel lucky to be in a job that humbles me every day. For my own personal growth, it’s been an amazing experience. You want to be in a job where you are learning constantly. This career has fortunately provided that experience.

For one, I get to learn how to build a company or firm. With the ever changing nature of running a company in the tech world, there’s always something new and everyday is different. One day you’re dealing with people issues, the other day a tech issue, and another you may be on pitch calls for 8 hours. I can confidently say that I learn something new every day.

On top of that, the industry we are in of investing is perhaps one of the most humbling industries you can be in. It’s a world where if you are good at the job, you are usually wrong more than you are right. Even the top investors of the world get things wrong all the time.

I had yet another incredibly humbling moment this morning as I went through my inbox from a couple years ago. We had passed on investing in Anthropic back in the beginning of 2024. It was the right decision at the time as Secfi was a much different company back then and AI was still early. But obviously in hindsight, we would have done it. This world is full of regrets, but you can’t go back in time. So you just need to learn and make sure you take those learnings into the next opportunity.

Buying a home

With my rental lease ending on April 30th, I’ve been doing a lot of research on potentially buying a home.

My initial thought was that buying in Brooklyn for a place in a temporary stint would make little to no financial sense. I was able to confirm that with more concrete numbers from Claude. Simply put, the closing costs of everything just didn’t make sense. Not to mention all the other unexpected cost of the house like repairs. So for now, we’re going to continue renting.

On the other front though, this analysis did spark a conversation about buying a home in San Francisco in the next few years as well. I’m enjoying being here in New York, especially from a work perspective. But from a personal perspective, being home in San Francisco in the long-term likely makes the most sense.

When I moved here last year, I told myself that it would be a 3-4 year stint which would take Colin to 4-5 years old. Naturally with him starting school, that would likely be a good time to make the move. If we also want to have another kid in 2027/2028, living in New York undoubtedly makes things harder when it comes to space.

Financially, this timeline also works out nicely for buying our home in San Francisco for the next 15+ years. That process for us likely starts to get serious at some point next year.