Monday musings

My college friends and I were joking in our group text this weekend about how much we miss the younger days of partying where we could eat and drink what we want for how long we wanted. The days of being out at a beach with your friends and some beers, and nothing to do is something we were all reminiscing about.

However, at this point, I’d wager that almost equally as great to that freedom may be just be waking up feeling refreshed and amazing. This morning I woke up a rested man and popped out of bed. I got a 92% sleep score which is the best in recent memory. My sleep debt was reduced to basically 0 for the first time in weeks.

I went on a medium strain run that Whoop suggested before work, and I’m writing this feeling spritely at 11:30am and excited for the day ahead. If I could only replicate this feeling every day, life would be a lot better. The big question is what’s preventing me from getting there which unfortunately is a bit more complicated.

Behind this great Monday was a nice lowkey weekend with the family. We did our best not to overstrain ourselves and spent most of the time simply within the neighborhood with Colin. On Friday, we went out to an early and quick dinner with Colin that was magical as he was a champ throughout the evening.

On Saturday, we played basketball in the park in the morning and then went to a music class at Fort Greene park. Then we let him run around until he was exhausted at the Park Slope block party. We stayed on brand and on Sunday, we spent most of the day at parks or around our building just letting Colin play.

It was a largely boring weekend for Sophia and I, but the reality is that in order to feel good and get that rest that I need, our lives need to be more boring. That doesn’t mean we can’t have fun or go out and do things for ourselves. But it’s becoming more obvious to me that overdoing things has been Sophia and my achilles heel.

Another benefit of trying to slow down… I’m starting to learn that playing with my son is getting a lot of more as he gets closer to 2 years old. He’s starting to understand me more and more, and it’s getting easier to play with him. Playing with him doesn’t mean just watching him play with his toys anymore. I’m really loving this phase and spending time with him as much as possible.

Learning about recovery through Whoop

It’s amazing how much I’ve learned about myself and my body in the few months I’ve had a Whoop. A big part of it is the AI that’s built in that makes things easy to digest. I didn’t think I’d find the information very useful, but I’ve become one of those people that’s a bit addicted to it which is a net benefit for me.

I love learning and when you add an aspect of learning to be healthier and feel better, it’s a no-brainer and think that everyone can benefit from the data that’s collected.

One of the big things that I’ve been incredibly frustrated with the last few years is that I don’t seem to be making much progress in terms of my fitness. That is I work out 4 times a week and live an active lifestyle, but I don’t see the numbers go up a meaningful amount. My run mileage and pace is getting slower. My lifting numbers are stagnating a bit. On top of that, I feel constantly sore and tired.

With a combination of Whoop and ChatGPT, I’ve come to the realization the last week that I am not gaining because my recovery is poor. Just as important as working out is making sure that I recover and build on that workout. I was doing the opposite.

My tendency has always been to push through. If I’m tired, I would often prioritize a workout. On top of that, my Whoop has let me know that I do too much on my runs resulting into a counter-productive workout.

I always figured going hard on my runs would be better to building my cardiovascular health. Turns out that I need to slow my heart rate down on these runs significantly in order to actually build that health. I was not building a good foundation for gains.

My philosophy with my workout has changed and I need to trust the data and focus on recovery. My Whoop has now become my fitness coach and I love having it.

Learning from our kids

We had dinner with some old friends that were in town last night. It was a real nice night out eating great food and just relaxing which is rare for us on a Wednesday nowadays especially with Colin. Our friends also have a young toddler and naturally our conversation centered around our kids and our experience the last year and half.

My friend’s wife is an impressive founder who I’ve always known to be very introspective. She mentioned one of the biggest learnings for her as a new parent is just how fearless her daughter is and how as adults we live life naturally very fearful. She drew on her experiences a founder being worried about everything and just scared of making a mistake, and vowed to try to live life more fearless like her daughter.

It was an insightful thought and had me thinking throughout the night and this morning. She’s absolutely right and I can see how I’ve started to live life a bit more cautious than perhaps I did even a few years ago. As I’ve gotten older, I’ve realized that the stakes are much higher and that has made me perhaps a bit more hesitant and fearful of the outcomes.

Simply put, I’m more worried about making a mistake now than I was 5 years ago at Secfi. It’s perhaps time to change my mindset a bit. Great companies are not built by people who live life fearfully and hesitant. They say you learn a lot more from you kids than you teach them. It’s good for me to realize that and learn from Colin.

Protecting my blocks to learn AI

My list of videos and articles of the latest trends in AI is now surpassing 4+ hours worth of time. I’ve definitely got a bit of anxiety that I’m being left behind in this world. I suspect I’m one of many with how fast things are moving.

As someone who loves learning and playing with new tools, it’s incredibly frustrating that I don’t have much time between work and my family to sit down and play with the latest technology.

I’ve done an okay job carving out time at work the last couple of months to learn the tools, but it’s clearly not enough and my previous blocks almost always get taken up with more pressing work matters.

I think the good news with how fast everything is moving is that everything I want seems to be getting built for me and added as features in my day to day tools. For example, I was planning on building a morning briefing in Claude that research every meeting I have for the day. Low and behold, Granola just launched a feature that already has this built in and scans my inbox, Slack, and Hubspot. So that’s one less thing for me to build.

Regardless, I need to protect my blocks and really spend time on learning. In this day and age, there’s really no excuse not to.

A long weekend

It was a “long” long weekend in New York. Sophia and I decided to just stay home to try to relax and enjoy New York this Memorial Day. Unfortunately, the weather did not cooperate and we basically had rain the entire weekend. This normally wouldn’t bother me much, but with an active toddler, life was a lot more stressful.

We tried to make the best of it by going to a mall on Saturday which ended up backfiring and being an awful experience with Colin wanting to basically run around the entire time.

Our evening to ourselves on Sunday was canceled as we made a mistake and forgot to confirm the baby sitter. I did have a nice day on Friday golfing in the morning and hanging out. But besides that, I was pretty exhausted chasing Colin around and trying to keep him entertained indoors.

It was a good learning experience for Sophia and I. When these weekends happen, it’s quite obvious that less is more. We unfortunately did quite the opposite of that. After our debacle on Sunday, we tried to salvage the night by going out with Colin which just exhausted us even more. It was a long Monday and my Whoop recovery score was in the red most of the weekend.

My focus this week and weekend will be about getting back on track.

SpaceX S1

The SpaceX S1 is out and the largest IPO in history is officially on. I haven’t had a chance to read through it much and likely won’t until this weekend, but I’ve been reading some tidbits on Twitter and they are fascinating.

My favorite bit so far was Elon’s pay package which includes significantly more stock if he gets 1 million people to a Mars colony.

Anthropic is also $1.25B per month to SpaceX for compute. I wonder how many millions of dollars have been burnt in compute cost to analyze SpaceX’s S1.

The content from this is going to be fascinating. I’m interested in what the S1 says about the SPVs and the lock-up expiration in particular, but there’s going to be nuggets of gold staggered throughout this S1.

The tax industry

I no longer work directly in tax like I did at PwC, but given my Master’s degree in Tax, I still follow along quite a bit. I don’t have a burning desire to ever go back into the field directly, although I am a bit jealous of the new graduates in the industry that are going to be able to do this in an AI native world.

I ended up working at PwC one of the Big4 firms in their Asset & Wealth Management team on the tax side. My first two years were basically grinding spreadsheets, putting things in software, and checking things. The industry works in that you are basically a grunt and do all the boring low level stuff at the beginning, and with the 80 hour work weeks, you’ll eventually learn the ins and outs of taxes for large investment firms and corporations.

At some point, you’ll start to do more “value-add” projects like advisory work for firms and act as a true consultant. But it’s a grind and incredibly boring for the first few years. I ended up moving to a more technology consulting practice after 2 years just out of pure boredom and that worked out well for me.

With this new world of advance technology, I see no reason why those first 2-4 years of grinding really needs to happen anymore and that will easily be replaced by AI. The key thing is that the new graduates will need to learn still and part of learning is grinding through how everything works. It’ll be fascinating to see how firms manage this going forward.

I also think there is no better time to get into the tax industry right now. With technology, you can eliminate 80% of the horrible boring work like putting numbers into a tax return and focus more on the value add items like consulting and complex calculations that people are willing to pay a human for.

Relabeling blue collar work

I am curious as to the shifting dynamics of the modern American Dream. I was born in 1990 to immigrant parents, and for my entire blessed life, the dream has been for our kids to go to college and work a “white collar” job. Growing up that was to be a doctor, lawyer, engineering, accountant, etc. Naturally the tech side of the world grew as I became an adult and that’s where I gravitated towards after working at PwC.

I’m not saying this is a good thing, but the reality is that my parents never envisioned that I would be anything but a “white collar” job. They did not want me opening up a restaurant or working as an electrician or plumber. These jobs are of course incredibly important in our society, but for my immigrant parents, that wasn’t on the table.

I do believe that a lot of us are just not meant to sit in front of a computer all day for our jobs. My generation is burnt out and stressed despite making more money and working “cushier” jobs. But in my 13 year career, I have learned that a lot of people I’ve worked with and hired may actually be happier out there doing something different. For example, I had a coworker at PwC who said her dream job was to be a barista but she was at PwC because her Dad was a partner there.

Now in this day and age of AI, I wonder if there is more of a rebalancing back to the traditional “blue collar” world. These are essential jobs and I wonder if the perhaps somewhat negative stigma of “blue collar” starts to change. The optimistic view is that wages for these jobs will go up and life style could also improve at these roles. What was once a physically taxing 50+ hour a week job maybe could be improved with technology resulting in hours reduced, and pay increased.

A restaurant which has historically been known as a horrible business to get into maybe becomes much more appealing in 5 years. I have no idea and this may be overly optimistic, but I hope that is the case.

The confusing market

It was the first official summer weekend in New York with temperatures hitting 80 this weekend. I took full advantage and enjoyed life meeting with an old friend all afternoon Saturday, and then hanging out with a friend at the pool on Sunday.

It was the weekend I needed after a long couple of weeks. I haven’t been very social in the last few months with the demands of the job and life as a parent. I’ve focused a lot of my time into rest and being a good parent, and with summer finally here, I think it’s time to relax a bit and have some fun.

Prior to leaving on Friday, I got out our state of the private markets newsletter. And on Saturday, I had some good chats with some of my friends also in the industry. The vibes are definitely a bit… well weird and confusing.

One of my friends who has historically been in software PE has mentioned that things are just depressing at his old firm. They’re holding a ton of SaaS companies still and they’re all coming to terms that things are likely not going to end up at how they thought when they invested. The gist is that it may be 3+ years until they can sell some of these companies.

On the other front, AI is front and center and it’s hard to ignore Anthropic and OpenAI both looking to go public at $1T+ in the coming year. Even in the earlier stage AI world, it’s tough to see how this will all shake out.

Many of us have been at conferences the last few weeks and the consensus from all of us is that it seems like everyone is doing the same thing. AI CRMs, AI agent operating systems, etc. but it’s hard to see any differentiation at this point among the early players.

Of course things will change and the market will settle down over time. The first domino is of course the looming SpaceX IPO. I’m cautiously optimistic as we head into a monster June.

Colin at 18 months

Colin is now 18 months and I’m loving this stage. Of course every stage has it’s pros and cons, but this is really the first time that I’ve been able to “do things” with him in an interactive way.

For example, he loves his mini basketball that I bought him and he leaves going to the basketball court just to play with his ball. I get to shoot around and “teach” him how to shoot a basketball. Playing basketball with him is one of the biggest joys in my life right now and every weekend I’m looking for a park for us to play.

His personality is also really showing and he has his Dad’s appetite and desire for food. He is not a picky eater and will try nearly anything. He’s very vocal about wanting to try everything we’re eating and I find it absolutely hilarious. His new love for tacos brings me joy every time.

I’m loving this stage and being a Dad. It’s been a lot of work the last year and half of trying to figure out fatherhood and making big life adjustments so I can be present and be the best Dad possible. I still have a lot of work personally on myself to get to where I want to be. But I’ve made significant progress and that’s something to be proud of.

America's defense startups

It’s a gorgeous sunny morning here in Atlanta. I’m writing this from the garden of Hotel Granada which as the name implies is a Spanish themed hotel. Flight delays and going from meeting to meeting yesterday aside, it’s been a great short trip.

I met with some of our clients who are building the future of America’s defense. Unfortunately we live in a world where startups building weapons of war is a necessity to secure the future of our country. After meeting with some young, brilliant, and mission driven individuals yesterday, I feel better than ever that our country is in good hands.

Of course, my hope is that we’ll never have to use these said weapons of war. Fittingly, President Trump and lots of America’s business leaders are currently in China meeting with President Xi. I remain optimistic that the world’s two superpowers can work together for a more prosperous human race.

I’m intrigued at what the outcome will be of these meetings. I’m glad that President Trump isn’t going alone and he is surrounded by some of America’s smartest business leaders.

On to Atlanta

I’m off to Atlanta this afternoon for a quick 24 hour trip to meet with some partners and clients. I used to love traveling for work a lot in my previous job many years ago and early on at Secfi. With the pandemic and the rise of Zoom, it really did eliminate a lot of the need for travel.

Along with the rise of Zoom, getting older, and also having a kid, I’ve been more and more reluctant to hop on a plane. Reality is though that there’s nothing like in-person meetings both for productivity and trust.

For that reason, one of the goals for myself and the team is to travel more this year. It’s going to a challenge being away from Colin and Sophia having to solo parent more, but my hope is that I can be more efficient with my required travel. A big part of that will be making sure that I take care of myself and prioritize rest on these trips as well. There’s a happy medium here that’s possible.

Guaranteed change

We spent another weekend in Baltimore with my in-laws. It’s always an exhausting time down there for Sophia and I. Dealing with aging parents isn’t easy and layer on 18 month toddler in there and it’s like you have 3 kids at once. Of course, it is important for Colin to spend time with his grandparents so we’re glad to make the trip.

During this trip, Sophia wanted to get the ball rolling on moving her parents out of their home they’ve owned for 50 years. The home is old and not conducive for them to live in anymore and one of the goals is to move them to something more friendly like an apartment with an elevator.

I’d imagine this is a common problem, but this is proving to be a lot more difficult for my in-laws than we previously thought. You become attached to the place where you raised your family and your things. Downsizing and giving up that home is not easy for them. This should have been done years ago, but they’ve delayed year after year.

Ultimately though, I know my in-laws would love the new change of pace. Moving to an area where they can walk places without the hassle of driving can give them new life. A new living situation would breathe a lot of life into a 75+ year old couple. I hope that we can make them realize the pros of moving rather than focusing on the cons and that’s been my focus.

For a couple that has lived in Baltimore their entire lives, change is a good thing and inevitable. I hope they can realize that sooner than later.

Rising costs

For perhaps the first time in a awhile, I’ve really started to notice the cost of everyday expenses go up. Of course, the gas prices from the war in Iran is the obvious one, but I have never driven that much as I’ve lived in cities. Things that I never really paid attention to in the past such as groceries and menu items at restaurants have noticeable gone up in the last year.

For example, the cost of beef has gone up by up to 50% in my local Whole Foods that I shop at. A ribeye steak which used to be a treat used to cost close to $20 per LB, and over the last year that I’ve lived here, the cost has slowly risen up to $30 per LB. Salmon used to be priced in the low teens per LB. Nowadays, it’s up to $20 per LB.

I am fortunate that my family can bear these costs. But if I am noticing a difference and if that is impacting my buying behavior slightly, the impact on other families will be much more significant. If we’ve seen anything in the last few elections, Americans care about putting bread on the table first and foremost. Trump promised a more affordable America and to put America first. So far, we’ve seen the opposite.

New York giveth and take it away

New York has a funny way of energizing you and then draining you all at once. I spent most of my day at the AI Agent conference in midtown and then hopped over to my alma mater’s annual event, Dawgs on Wall Street. I met some amazing fellow Husky alumni and the guest speaker was David Finkelstein who is the CEO of Analy Capital Management, a public $100B REIT.

Networking can be draining, but I’ve made it a goal to get myself out there more since I moved to New York and being at the event gave me a lot of energy and excited for this opportunity to be in New York again.

Of course, the city also has a way to take it out of you as it took me about an hour and half to get home from Midtown yesterday. The F train got stalled due to a broken car in front of it so I switched to the 6, then the 5, then the R. That R train started running express so I had to wait for the next R train. By the time I got home I was absolutely drained and starving.

New York is the greatest city in the world. I do love this place and despite all the issues, I love being here and I feel fortunate that I get to spend at least the next few years here building a company alongside a great team.

Grateful to learn

I find myself in a fortunate position that I get to work a job where one of the the job requirements is that I need to learn and continue to learn. I’m at the last day of the AI Agent conference and my goal is to take it all in and enjoy learning and meeting people building.

These conferences can be a big drag at times and the networking is admittedly draining at times. But with the right mindset and will, these are great places to learn and meet very interesting people.

AI Agent conference

I’ve been at the AI Agent conference in New York which runs through tomorrow. I’ve been to a lot of conferences in my career, but I can confidently say that this was definitely the most eye opening purely on the fact that everything is so nascent.

When I got back to the office, I joked that a when I saw my first no code AI agent platform, my mind was blown with what could be accomplished so quickly. Fast forward to today, and I saw numerous other startups that I’ve never heard of with nearly an identical platform.

The presentations from the speakers were a mixed bag as always, but one of the takeaways from the handful that I sat in on today is that everything is early and no one really knows for sure how to do things fully yet. I did learn a lot of best practices from an organizational standpoint which was incredibly helpful.

In terms of the startups that I met, it was interesting as it felt like half the booths were 10+ year old companies launching new AI products like a startup again. Everyone seems to be reinventing themselves to become AI native nowadays.

Where has time gone?

I’m officially moved to my new apartment a whopping block and a half away. As someone who has moved across the country multiple times, this was a relatively easy move all things considered. But as someone who has also moved literally next door as well, no move is ever stress free.

I do love our new apartment and it’s been a clear upgrade over our last building. There are more families here and the building runs a much tighter ship. I’ll be spending most of the weekend and next week unpacking still, but it’ll all be worth it once settled in.

Probably lost in the craziness of the move is the fact that it’s now been a year since we moved to New York. It felt like yesterday that we showed up at 6am to our apartment to pick up the keys exhausted after a cross country flight. As the saying goes, the days are long but the years are short.

Looking back, the move has been great for myself and the family as a whole. We do miss friends and family in SF, but being in New York for another stint was a welcome change of pace. Being in office with my coworkers has made work a lot more fun, albeit a bit more hectic in a good way.

Going in my second year, I want to make sure to really enjoy my time in New York with Colin. If the first year was about getting adjusted, this year should be about living life a bit more. Before I know it, I’ll be writing here that our stint in New York is ending.

The state of the private markets

I’m writing our quarterly private market update for our newsletter to go out this week. Things are just a bit strange right now with the dynamics going on.

The window IPO is virtually closed for anyone not named SpaceX, Anthropic, or OpenAI. Those 3 companies will likely debut at over $1T each when they do decide to go public. Besides those 3 companies, there’s maybe 10 others generating interest in the secondary markets. The concentration of demand is something that I haven’t seen in my last 8 years working in this space.

On top of that, virtually all deals being done seem to be either VC selling off their positions or people selling SPVs. There are very legitimate SPVs and they serve a purpose in the market. However, whenever there’s a wealth creation event, there will always be grifters and people flocking to the space to get rich quick.

There are a ton of SPVs being offered and this feels like 2021 all over again, but on a much bigger scale. For better or worse, everyone wants a piece of the action again in the private markets. Once the dust settles, unfortunately a lot of people are going to get burned.

Moving and Gowanus

Colin woke up with a slight fever this morning so it was a stressful morning. Luckily it was low enough that daycare was still happy to take him in, but he wasn’t himself and I think one of us will have to go get him eventually. Your kid being sick is something that I never thought about until I was a parent, but it’s an absolute brutal situation and effectively one parent has to give up the workday to go take care of him.

Of course, this is all happening as I am starting our move to our new building tomorrow. When we moved to New York last May, we signed a 1 year lease in case that we didn’t like the area, apartment, or the market dropped. Fortunately, we loved the area and apartment but the market did drop so the lease ending gave us flexibility to negotiate.

Ultimately after an annoying negotiation, we ended up signing a new lease in a building down the street. We ended up upgrading in both the unit and building, and lowering our gross and net effective rent. It was a no-brainer but alas we have to deal with this annoying move.

I will say that it’s quite amazing how many new apartment buildings are being built right now in Gowanus. As someone from San Francisco who rarely sees new construction, what’s happening right now in Brooklyn is encouraging. By the end of the year, I believe there may be anywhere between 5-10 new large apartment buildings up and running in the area.

There’s a lot of hoopla about Gowanus and the canal. Yes, it doesn’t look amazing and can smell at times. But I personally love the area. The public perception seems to be very mixed. We view Gowanus as great location that’s up and coming nestled between the popular Carroll Gardens and Park Slope. We have access to both neighborhoods and our commute to the city isn’t that bad.

Most important for me is that the culture of the area is still in-tact. Whenever new high rises go up, the area almost always feels a bit stale and weird. See Mission Bay in San Francisco. But for now, Gowanus is still maintaining a cool culture with lots of great restaurants and spaces. I’m happy to be staying in the area despite a stressful move with a sick kid ahead.