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.

AI optimism

Most of the world seems to be getting more terrified about AI. It’s the same old fears that are reverberating throughout the population. AI will take our jobs. We are headed for a dystopian society where we can’t think for ourselves. The world will be run by a select few elites. AI will eventually kill us.

I really do understand the fears to a certain degree. No one likes to think that their career which they’ve built over many years may be taken away by AI. And there will be some serious negative consequences that come out from AI. I’ve thought about all of them as well and how myself and my family may be impacted. I’m human afterall.

However, I truly deep down believe that everything is overblown by multiple levels. Like any new thing, we are overestimating the negatives and underplaying the positives. The one thing AI cannot be is human. For that reason, it will never take over.

I choose to focus on the positives which means a better life in where AI eliminates draining work in our lives. Whether that means that I will continue on in my chosen career path, or pivot to doing something different is yet to be seen and that is the part of life that can be exciting if you let it be a positive.

AI slop

We’re in the process of hiring and unsurprisingly, a lot of applicants clearly are just using AI to mass apply to roles. It’s brutally obvious, especially when most of the answers from each candidate turn out to be nearly the same.

I have no issues with people using AI to help them write or proofread, but there’s a level of authenticity that you’re looking for. Most of the answers I see have no original thought or even come close to learning about that person as ChatGPT wrote it.

In this era of AI, I believe that most human wins. Our brains is the one of the only things that AI can’t completely tap into. Those who want to think for themselves will be the ones who will thrive in this day and age.

The months ahead

It feels like there’s just not enough hours in the day right now between work and personal obligations. A lot of us are feeling the strain as we work to close out spring and head into summer. Unfortunately, the idea in finance of “sell in May and go away” is not an option for us with everything happening.

Luckily, it’s all good stuff as we are focused on growth and seizing the opportunity. After going through the last downturn, we’d obviously take a mountain of work for good reasons over the alternative. For me, this mindset shift is important to get me through.

I can sit here and stress about my entire day being packed with meetings, interviews, etc. Or I can look at it from a perspective that we are growing a successful business that is never easy to do. There will be growing pains and a lot of work upfront, but it will be all worth it once we get to where we want to be.

Post trip thoughts

I’m back in the office after a short few days in San Juan, Puerto Rico with the family and the in-laws. It’s an absolutely gorgeous place with amazing people and culture. I loved being able to explore a new place and culture again as this was the first time going somewhere new since Colin was born 18 months ago.

All that said, things are different obviously nowadays with Colin. I’ve learned a lot between our last trip to Mexico in the fall and this trip to Puerto Rico. Vacations aren’t really vacations for the parents anymore. It’s more about gaining quality experiences with your kids which is magical in many ways, but not as relaxing or enjoyable for the parents.

The highlight of my trip was yesterday morning before we packed up to fly home. We took Colin to the beach for the 2nd time this trip and this time around, he was a lot more comfortable and starting to love the water. He was smiling and laughing as he ran up and down the shore. It was a magical moment after an up and down trip.

I wish I could report that it was an awesome trip the entire time, but my stress levels felt at a medium-high level for large portions of it. Part of that is just being a parent of an active toddler where you just have no idea what to expect. Part of it was also having my elderly in-laws with us. And the last and probably worst part of it is my inability to deal to shut off and deal with my stress from other areas well.

I unfortunately let a lot of work stress seep into this trip and it was on my mind for large parts of the trip. This was something that didn’t need to happen and a lot of it was self-inflicted. I have a lot of work to do in this department to ensure that I stop bringing this stress home and impact my personal life. In retrospect, none of the things I stressed about moved the needle and ultimately it was a nothing-burger that lived in my head.

On the topic of stress, I wonder how much being in New York this last year has changed me. Sophia and I were chatting last night about how stressful getting an Uber in San Juan was despite not being a very stressful at all. The drivers were always helpful and patient, but we felt like getting a simple Uber was an incredibly stressful situation every time given Colin and my elderly parents.

I wrote a little bit a few weeks ago about how my perception of wealth has shifted a bit since moving to New York. I wonder just how much living in New York has changed me. Everything is well… just more stressful here. The crowds and the people. All the reasons that make it a great place to live also have a trade-off that nothing is ever easy.

I wonder if I’ve just become an angrier and less pleasant person in the last year. If I’m asking the question, I probably already know the answer there. It’s one of the many things that I need to work on this year.

Time for a break

I’m headed for Puerto Rico with the family tomorrow for a short vacation. I’m feeling a bit of relief today as I work to wrap up a long couple of weeks with an offsite over the weekend. It’s a much needed proper break. I’ve taken some days off here or there, but have not fully gone away to unwind since January. A few days on an island after a tough winter is much needed.

With Colin at 17 months, vacations nowadays are much more difficult. We have to brave the flight with a very active child. Then we’ll always be on his schedule which is basically just roaming around any chance he gets. Visiting new restaurants or seeing the sights is usually a short lived experience. On top of that, while on vacation, we don’t have daycare like we do at home where we can drop him off and take a break.

For that reason, we’ve decided to make our trips shorter than the usual 1-2 week trips we used to do when it was just us two. We just simply get too exhausted and want to balance taking a trip to do something new and parenting in a new location.

For me, that means that I need to maximize my short vacation and ensure that I get the proper unwind I need so I come back on Wednesday ready to hit the ground running. That means doing my best to stay off my email and work so I can actually recharge.

The fight for compute

The funny news of the morning is that Allbirds has just pivoted to AI compute which resulted in their stock jumping up 300%. The company’s assets were just sold to a party so the company was effectively a shell company at the time, so it is worth noting that it’s up 300% on almost nothing. But regardless, it’s representative of the times we are in.

Compute is everything right now. New frontier AI models are getting more and more powerful, and we do not have the compute to run them. Anyone providing compute seems to be signing large contracts. The question is whether all these providers can deliver on the demand.

We’ll be seeing data centers popping up everywhere. Perhaps Elon is onto something with the data center in space.

If a struggling shoe company is now pivoting to selling the picks and shovels of the gold rush of AI, I wonder who will be next. The fight for compute will be the story of the next 5-10 years. I hope we have our smartest minds and government support in winning that battle for compute.