Secfi in New York

We have the US team here in New York for our annual holiday party. I always love when the team can get together. Obviously a big part of the trip is having fun and bonding with each other, but the amount of work that gets done in these few days together cannot be overlooked either.

Productivity goes through the roof and it feels like we get through things multitudes faster than we would over Zoom. It is a bit of a shame that we do not get together with the Amsterdam team more. Logistically, it is just a bit of a challenge and makes sense for why we don’t do that on the regular basis. But going into 2026, I do want to focus on doing more work in person and that may mean traveling much more than I did in 2025.

Baseline

It’s amazing how different I can feel from one day to another. I woke up this morning after a great night sleep feeling refreshed. I did a running class this morning and was at my desk with a positive attitude and energetic.

That was night and day from yesterday where I woke up feeling like shit and basically just trying to survive the day after a horrible night of sleep.

Of course, I know it’s impossible to have a great night of sleep every night and feel amazing all the time. Life and things happen and sometimes it’s unavoidable. Right now, it feels like my life is peaks and valleys.

I’d like to find a way to get back to standard baseline. The consistency will make things a lot easier on my life and happier overall.

The Monday sleep issue

One weird but consistent thing in my battle against sleep issues is insomnia on Monday nights. It doesn’t happen every week, but when I have trouble sleeping, it almost always falls on a Monday night. It happened yet again to me last night as I lay awake most of the night trying to sleep. It also happened again last week.

It’s something that’s been going on for years and I can’t explain it. I almost always sleep like a baby on Sunday night, but no matter how tired I am on Monday, I feel like I struggle to fall asleep. This includes good days where it’s a low stress day and I worked out, and had a nice meal.

By process of elimination, I have tried a lot of things to combat it. I have tested many theories that I felt could be the culprit including making sure I exercise on Monday, staying consistent on sleep schedule on the weekends, not drinking over the weekend, going to bed earlier, staying off the phone, etc.

At this point, my only thought is that it is just simply mental at this point. The idea of it being Monday makes me think it’ll be tough to fall asleep which gets in my head and becomes a self-fulfilling prophecy.

I look forward to the day that I can put this behind me. Having a day of the week where I sleep terribly is not a great way to live.

The college football mess

Yesterday, Sophia and I hired a nanny so we could go to my friend’s birthday party at a bar in the late afternoon. This was a friend from college who I’ve known since freshman year, and it was a bit of a reunion of our college friends in New York.

It’s funny how much things have changed in the last few years. There were a handful of us that have kids and we mostly congregated with each other to talk about parenthood. The others without kids were all still talking about their epic weekends. One of my friends went out to 4am on both Friday and Saturday. That gave me a ton of anxiety just thinking about it, but at same time I do miss those days a bit.

On another note, the news headlines dominating the sports world has been the college football playoff selection committee particularly around Notre Dame being snubbed out of a playoff spot. In addition, we have multiple teams opting out of playing bowl games and a coaching carousel controversy.

Despite a lot of calls for why college football is broken, we are actually in an interesting era where there is a ton more parity than ever before given the transfer portal era. We could be entering the golden ages where more teams can actually compete for the National Championship rather than the same 3-4 every year who previously bought their way to a title.

While I am actually excited about the future of college football, there does need to be some wholesale changes to the game I love to ensure that the system does not break. We need to fix the transfer portal and coaching carousel issues first and foremost.

There should be no reason that a team like Ole Miss in the playoffs has their head coach leave in the middle of the season. The transfer portal also needs to be AFTER the full season ends or else you risk a situation where players will leave contenders in the playoffs.

Finally, we need to some sort of regulation around NIL. We cannot turn this into a situation where the best team is the highest bidder always. That was the issue in the previous years of college football where teams in the SEC would pay their players and buy their rosters before it was legal. NIL becoming legalized paved the way for more parity, but we can quickly turning into a money war again as teams find ways to sidestep the rules.

The next few months will be interesting. I feel like we are at a bit of a fork in the road. We are either headed towards the golden age of college football or we are headed to a bad place that is unsustainable and will eventually hurt the sport.

Diversifying access or dumping on retail?

I just read this troubling article about YieldStreet which is a VC-backed platform play that looks to provide access to alternative assets such as real estate for retail investors. It turns out that up to 30% of the real estate investments that YieldStreet provided are in risk of default and the company is now rebranding to Willow Wealth alongside removing historical performance numbers.

In general, I’m fairly supportive of giving folks access. I would like to believe that the folks at YieldStreet had the right intentions in mind when they started the company. But when you go to retail, the risks are higher. These are everyday folks with jobs and families to support. Who knows how much of a person’s portfolio was put into these types of investments. The losses could be a material impact on one’s financial future.

I don’t know what went wrong with YieldStreet. I am not well-versed in the real estate space and I do not own any real estate at the moment. But I do know that there is a troubling trend right now with more and more platforms seeking out money from retail.

Audio tapes to live video to ?

I remember when I was a kid, I would often record audio tapes which we’d send to my Uncles and Aunts in Indonesia. I’m not that old so the phone did exist, but it was still a normal thing for audio tapes to be shared so loved ones could hear it.

It’s pretty crazy to think that just 30 years later, we are now doing live video calls from almost every corner of the globe at a price cheaper than it would take to record an audio tape. My son Colin is going to grow up being able to talk to any loved one with 2 clicks at any time and nearly anywhere.

At the pace technology is evolving, I wonder what Colin will have at his disposal. Is it that crazy to think that he may actually be able to go from San Francisco to Indonesia in an hour or two versus the nearly 24 hours now?

The future is fun and scary. There’s undoubtedly a lot of problems my generation and Colin’s generation will need to solve. But I think if there’s something to be excited about, it’s the prospect of technology making our lives better.

I’m glad I get to be in a job where part of my role is trying to predict what the future will hold.

Prediction markets

Fanatics announced that it was entering the prediction markets game today by launching in 24 states. It’s no surprise as Fanatics has been moving into gambling the last few years. But the big trend right now is these prediction markets which effectively utilizes a loophole to create legalized sports gambling.

Our current government does not seem that they are looking to regulate at all. As such, these startups like Kalshi and Polymarket now find themselves competing with the largest casinos of the world for their cut of the degenerate sports gambling market.

I don’t know how this will end up. I can only imagine that the casinos have these startups and this loophole in their cross hairs and they will spend billions of dollars trying to fight for their right to the market. It’ll be fun to watch from the sidelines.

What I do know that is that gambling is not going away. Whether it’s done through casinos, government regulated companies, offshore, whatever, people will find a way. There is too much of a demand for it.

I’ll do my best to limit my own willingness to sports gamble to vacations to Tahoe or Vegas. As anyone can tell, it’s incredibly addicting.

All quiet in the private markets?

It’s a bit of an interesting time right now in the private markets.

On the surface, you have the largest AI and AI adjacent companies raising round after round at large valuations. These companies like OpenAI, Anthropic, Databricks, etc. dominate the headlines day after day. It feels like every other day there is a new mega round into one of these AI companies.

But what about the rest of the market? There are hundreds (thousands depending on how you see them today) of other “unicorns” sitting underneath the top names.

On the other end of the spectrum of the incredibly fast growing AI companies are the startups that have plateaued in the last few years. They may be profitable, and possibly growing but doing so slowly. Many of them are going to have to effectively reinvest themselves in order to get back in the race to an exit. I suspect what will happen is that many of them will just turn into self-sustaining SMBs over the years as they are left by the VC market.

Somewhere in the middle, there’s a handful of these companies doing well albeit a bit more under the radar and much slower than what’s happening in those AI companies. These companies have been quietly growing towards an IPO and offering liquidity to their employees. The PR angle with these companies have seen to be to stay under the radar whether that’s by their choice or not.

For a fan of technology, the AI companies are the ones that I find interesting. It’s fun to learn about them and see how they are going to change the world.

From an investing standpoint, I’m more focused on the companies in the middle right now. There are a ton of great companies being built that are being overlooked. Joining the circus of the thousands of people chasing the top 15 names is something that does not make great business sense for us right now although that may change.

December

I had a fun but exhausting Thanksgiving. I went into the holiday week tired with a busy weekend before and some bad sleep early on in the week. Sophia, Colin, and I then pretty much made the trip to Baltimore and spent the next few days out and about.

It was anything but a relaxing week unfortunately. It’s once again, another adjustment that we’ll need to make in our new lives as parents. We just simply cannot handle overdoing things on these trips and we need to bake in more time to relax and recover.

On another note, it’s December and it’s crunch time. There’s a ton we need to get done at work in the next 2-3 weeks and there’s a ton I need to get done personally as well. My hope is that we can work hard to getting everything in a good spot in these next 2 weeks. Then we can spend one week of clean-up and wrap up the year casually before everyone takes off for the holidays.

It’s something that I have been preaching to the team. If we can work hard and take care of business these next 2-3 weeks, then we can have the full 2 weeks off at the end of the year to spend with our family and friends. It’s been a long year and I hope that everything goes to plan and we can get that much deserved break.

Going easy on myself

I slept like absolute shit last night. It had been awhile that I had a night of bad sleep that wasn’t a result of going out or a social event. It was a bit of a weird day and night as I was just tired from the weekend, and just felt a bit run down. My old friend anxiety kicked in when I got into bed, and next thing I know my alarm is going off at 6:00am and I felt like I never slept all night.

I always like to beat myself up after these nights. I hate feeling like shit during work and needing 3 coffees to stay awake is not really my ideal scenario. While bad nights of sleep happen to everyone, I probably have a bit of blame on myself for not getting enough rest over the weekend and doing too much.

At the same time, beating myself up over this and other small things is a big part of the cause of all my anxiety. It can be a vicious cycle and I need to do a better job of giving myself a bit of grace. That should probably start by getting a bit of rest today as we wrap up work for the holiday.

Personal investing

It’s been a good month or so at home, and my life has slowed down a bit which has been exactly what I needed. Thanksgiving is coming at a good time where I’m excited to make the short drive to Baltimore, and also get a little bit of a break before I go through the year-end rush.

On another note - I spent an hour or so going through my family’s finances and starting my year-end planning. That entails updating our personal balance sheet and portfolio to see if any adjustments need to be made.

While I don’t advocate for counting your cash too often, I think it’s an important exercise to ensure that you’re being smart with your money. I used to do this nearly every month. As life got busier, it went to quarterly, and now it’s at an as-needed basis.

I no longer have the time or interest to do a lot of investing myself. About 5+ years ago, I used to love researching companies and tracking the stock market, and even picking some individual stocks myself. That interest has waned over the years. I suspect a large part of it is that I spend my entire workday doing it on the private market side. Another part is that I just simply do not have the time to track things anymore.

Without the time or brain capacity to do so, I’m likely doing more harm than good by picking individual stocks versus just letting my financial advisors handle everything. I will likely shift a lot of that capital into my managed accounts and perhaps save a little bit to make angel investments in 2026. That is one area where I know well and can make better informed investment decisions with not much work.

Entry level jobs in 2025

I went into this morning thinking that I was going to try to wrap up early today and spend a few hours relaxing before daycare pickup. By the time I got into the office, I knew that hope was over. That is life and it being Friday, the work unfortunately takes precedent. This concept is ingrained in me especially as I spent my first five years at PwC where I had people breathing down my neck often.

For better or worse, the first years out of school were mostly 5 days in the office and sometimes even 6-7 days during busy times. While I don’t that should be the norm, it did teach me a good work ethic and that the job was optional. If I didn’t want to do it, there would be others that would.

Maybe I am getting old, but I am getting worried that this next generation may not be able to grasp this concept as things have gotten too cushy lately. So far we mostly have had good luck with younger Gen Z hires at Secfi.

However, I know others who haven’t been so lucky. I had drinks with some old colleagues who are really struggling with the younger classes right now. They are much more demanding and quick to put up unreasonable boundaries. They seem to complain more and put up a larger fight when they don’t get what they want like promotions.

I do think some of this is good and companies should not have the opportunity to crush their employees. But there is a balance here and based on what I heard, it seems like it’s gone a bit too far. Couple this with the fact that more entry level jobs are being eliminated by AI, and it does not seem like a good place for a lot of college graduates right now.

My old friend and colleague put it best. “They complain more and work less, but they also have less opportunities than we did. So for better or worse, they’re forced to stick things out nowadays despite wanting more.”

Impermanence

It’s been a weird and difficult morning for me.

I started off the day with an early wake-up as Colin has started to show signs that he’s ready to drop down to 1 nap. He’s been an amazing sleeper, but he has been tossing and turning in his bed for an hour before falling asleep, and also has been waking up early which he hasn’t really done since he started sleeping through the night.

The writing on the wall is that he’s now a toddler which means going down to 1 nap and having a lot more different needs in life. It’ll be a slight change with pros and cons, but more so Sophia and I were kind of in shock that we are now in this position of dealing with a toddler as it felt like just yesterday we were taking home a baby.

There were moments where I wish I could freeze time a bit. Colin at this age is one of those moments and while I’m excited for him to grow, it is another reminder of the impermanent nature of life.

On that topic, I was also dealt a curve ball this morning as I found out that a friend of mine who is my age of 35 is battling cancer. It was out of the blue and I was just texting him about meeting up a football game a couple weeks ago. It was a big shock this morning that someone so young with a new baby could be dealt something like this. It was hard not to imagine that it could have been me.

He seems optimistic and knowing him, I have no doubt that he’s going to kick cancer’s ass. But it’s yet another remind how fragile life is. I know that the impermanent nature of life is what makes life special, but at times, the changes and curve balls of life makes things sad and scary.

Staying disciplined

It’s a cold and rainy Wednesday in New York. The office is nearly empty save for a few of us. Work is busy… but slow in an interesting way. There is not pressing or urgent, but I’ve got a ton on my to-do and it feels like nothing is getting off that to-do list lately.

Thankfully, I’ve got my afternoon blocked off so I can finally sit down and try to knock out some of my work. If I’m lucky, I’ll have a good 2 hour block where I can just grind through my checklist.

Unfortunately, on days like today, it’s a bit easier said than done. The holidays are nearly here with Thanksgiving next week. We’ve had a busy and stressful year. With nothing pressing, I’d be lying if I didn’t have the thought that I should maybe just take an early day today and try to enjoy some leisure time in the city.

I know from experience that these types of days where you need to dig deep and find that discipline and motivation from within are some of the most important ones. It’s a chance to get caught up and possibly ahead so I can actually enjoy my time off on the weekends and next week for the holidays.

These days also add up when trying to close out the quarter and year strong. That delayed gratification will be worth it in the long run so for now, I need to grab a coffee, some headphones, and get back to the grind.

Zoox is live in SF

I’m excited to get back home to San Francisco for the holidays. Of course, seeing family and friends is top of mind. But on the side, I’m stoked to try out one of the Zoox driverless taxis for the first time as well.

I first heard about Zoox back in 2019 when I met a few of their early employees who were at the forefront of building the driverless car. I found it incredibly fascinating speaking with employees there trying to do something that seemed so bizarre at that point. Low and behold, 6 years later and we have driverless cars all over the roads in San Francisco.

I know folks at Zoox would tell you that they wished they were able to get out to market sooner than 2025, but it’s still an amazing accomplishment. For me, what’s most interesting is that these Zoox cars are not retrofitted Jaguars like Waymo, they are built specifically to be a driverless taxi and looks like one accordingly with seats facing each other.

This looks like a much more fun way to travel throughout the city and I can’t wait to get in one in December. I’m counting down the days when I can take a driverless car to Lake Tahoe.

2025 was the year of adversity

I’m enjoying every stage of Colin’s development, but I’d be lying if I said that this stage isn’t a lot more rewarding the previous stages. Now that he’s 1, he’s just much more interactive and his personality is really starting to show. He will now come up to me to play and we will sit there giggling for minutes at a time. It’s an incredibly fun phase and I wish I could freeze time sometimes.

On time, I can’t believe it’s the holidays already with Thanksgiving next week. Before we know it, we’ll be in 2026 and kicking off the next year. Things are good right now with work and life, and I credit 2025 as being maybe the most transformational year of my life. Simply put, I had to grow up quite a bit this year.

I’m not sure if I accomplished more in a single year both professionally and personally. Looking back, it’s quite amazing how much of my life changed this past year and I am proud of myself for fighting through the struggles. It really was the year of adversity for me and I’ll hopefully look back at this year as one of big change for the positive.

First, I want to focus on closing out the year strong. From a personal front, I want to stay present with Colin as much as possible, and enjoy this holiday season. In the next month and half of work, I really want to focus on our people and really focus on empowering them to grow and add more value for the team. It’s a period of transition for this team, and that’s where my focus needs to be.

The money is flowing

I’m officially starting to get a bit worried. It feels a little bit like 2021 all over again. Companies seem to be raising money at a ridiculous clip. I know of a handful of companies who have raised 2 rounds this year at significant markups that are about to raise yet another round in the next month or early next year.

I understand a bit of the game that the VCs are playing. The most money you can lose on a $1 investment is $1 and the opportunity for outsized returns and to be an early supporter in one of the big AI winners is massive.

Of course, there are differences than 2021 in that the money is largely flowing into the AI realm versus virtually every startup out there. Still it is a bit unsettling as everyone knows there is a bubble here and people will lose money soon enough. There will be ripple effects throughout tech and the entire ecosystem from this. We can only hope that it’s a correction versus a massive prolonged downturn like last time.

Accumulating assets

One of the struggles this past year with big life changes like having a kid and also moving to New York has been financially related. I should say that we are by no means “struggling” financially. Sophia and I are very fortunate to live good lives out here in New York.

With that said, the cost of living bump of moving to NY, even from SF, and the increased cost of living of having a child has me thinking about money more than I have the previous 5 years before that.

Firstly, moving to New York City even from San Francisco in itself would mean a cost of living bump. Simply put, housing is more expensive here and you get less bang for your buck. While the day to day may be comparable, it is definitely more expensive to live here. On top of that, having a kid is just more expensive. You need an extra bedroom which adds to the cost of living. And you also add childcare on top of other expenses to provide for a human.

Again, I am not complaining. I live a great life and Sophia and I are fortunate to be very happy with where we are at. At this point of my life at 35 with one kid though, accumulating assets has been top of mind and unfortunately, that has really stalled out in the last 6 months since moving to New York.

I’ve been telling myself to give myself a bit of a break as this increased spending would happen to anyone. At the same time, I want to make sure that we get back to a world of accumulating more assets in 2026.

A half-year break from saving due to life changes is acceptable, but it’s time to start reeling things back and putting some more cash and investments on the balance sheet.

Multi-tasking and the art of doing one thing at a time

In my ever growing list of personal self-improvement wishes, one of the top items that I am actively working on is eliminating multi-tasking and focusing on one thing at a time.

This almost always has to do with me trying to do something personally while also balancing work. I had a recent frustration yesterday morning. With Colin home from daycare and Sophia and I having to alternate childcare and working, I tried to get a quick workout in the morning before work began.

Working out is usually a great escape for me to be present and take a break from the realities of life for a bit. I love the break and the subsequent endorphin rush that comes from it. But I decided to effectively nuke the mental clarity from my workout by letting work seep up and ruin my workout.

I had planned to get a quick and efficient 45 minute workout in, and be at my desk by the top of the hour. Instead I spent over an hour doing a half-assed workout and half-assing my work with no major productivity gains but additional stress. It was the worst way to start my day.

Unfortunately, I do things like this way too often at this point from trying to work while getting ready in the mornings to trying to work while feeding or playing with Colin. It’s a terrible habit and I need to be better for my own sanity and happiness.

Loving what you do

Just when I thought I was becoming a well-seasoned veteran as a parent, we’ve been dealt yet another curve ball with a Tuesday Federal holiday and a daycare closure. With all due respect to the veterans, I don’t ever recall being granted this holiday off in the past and both Sophia and I were shocked to find out that we’d have to be home with Colin today. It’s going to be a challenging day navigating work and childcare, but we’ll get through it.

On another note, I saw a tweet from UW radio broadcaster Tony Castricone yesterday and it had me thinking even into today. It was a long tweet but described his hectic 24 hours flying to cover the UW football team in Madison and then the UW basketball team the following day in Waco before flying back to Seattle.

Tony said something in the Tweet that really stuck with me.

“They say if you love what you do, you’ll never work a day in your life.
I disagree. I think if you love what you do, you’ll never work harder on anything else, and that’s why you’ll be successful at what you love.

Happy to be home and grateful to do this everyday. 🙏”

— Tony Castricone

I do believe I like my job, but that cliche quote that I’ll never work a day in my life has never resonated with me. For one, despite really loving my job building a firm like Secfi, there’s a lot of things that you have to do as part of that job that just downright isn’t fun. Of course there’s parts of company building that feel more like work versus working on a passion project.

That’s why I loved Tony’s adjustment to the cliche quote. I do love what I do, and while it’s not all fun and games all the time, there’s nothing I’ve worked harder on before in my life than building Secfi.