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.

Monday musings

I had an exhausting weekend with the in-laws and other family in town celebrating Colin’s 1st birthday. On top of activities for Colin, Sophia and I also went out to dinner Friday to take advantage of the free babysitter for the night. And then I went out with some friends on Saturday as it had been a few months.

It was a fun time, and I was excited to have guests over to celebrate Colin, but these busy weekends do take a toll on me and my rest. While Sophia and I do not want to get to a point where we stop going out, maybe I need to stick to 1 night of fun and 1 night of rest going forward.

On that topic, I’ve made a lot of strides that I am proud of in the last 2 years. Perhaps a couple years ago after a busy and full weekend, I’d be sitting here in a terrible state on a Monday perhaps half asleep with a lot of brain fog. Today, I’m in a good spirits, ran 3 miles before work, and have had an incredibly productive day so far. Slowly but surely, I am learning how to treat my body better.

On the work front, things seem oddly quiet but busy at the same time. We are not expecting anymore IPOs this year with the government shutdown and the holidays approaching. I’m sure there will be a pick-up of private market activity as we get close to the end of the year, but I’ve also heard that many funds and companies are pushing off things until next year at this point. Perhaps the busy comeback year has people feeling content on where things are at right now.

Focus

I am certainly glad that I am not flying anywhere this month as this seems like a nightmare scenario. The government shutdown is really starting to take it’s toll and while it has not impacted the majority of Americans, that will start to change. Of course, the government workers and the most needy are taking the fall for the rest of us. It’s a sad situation and reflective of the political world we now live in. And for the record, I blame both sides here.

On another note, the theme of the week for me has been focus. I feel like I’ve got a million things going on, none of which are incredibly urgent but everything feels critical. My brain has been in a pretzel all week with the context switching and trying to keep my head above water working through the many different workstreams.

At this point, it’s really time to triage some of these tasks and things are simply just going to have to wait or be deprioritized. On a small team, there is always going to be the feeling that we need to do everything or else there will be a missed opportunity. But over the years, I’ve learned that trying to do everything is usually much more counterproductive.

In order to be the most efficient, we need to be diligent with our time and make sure we stay focused on the most important tasks. That will almost always mean better results when the dust settles.

The private markets resurgence

Two big moves happened in the pre-IPO secondary space recently that went relatively quiet. Morgan Stanley announced that they acquired EquityZen last week and today it was announced that Charles Schwab acquired Forge Global which was a publicly traded company.

It’s been fun to see some activity in this space as it’s been mostly quiet the last few years since Forge went public. Two of the biggest legacy secondary marketplaces have now been acquired by large financial institutions. Undoubtedly, clients at these firms are demanding access to pre-IPO investments and these acquisitions help them achieve that.

Of course, this is all great news for Secfi as we operate in this space. We are adjacent to EquityZen and Forge, and while some may see us as competitors, we partner with them more than compete. They are both great companies and I’ve enjoyed meeting and partnering with many folks there.

I’m happy for all my friends at EquityZen and Forge, and for everyone building in this space.

Happy Birthday Colin!

It’s Colin’s 1st birthday today. While I can’t believe that it’s been a year, I also can’t believe all the things that we’ve been through in the last year. Like the saying goes, the days are long but the years are short.

Prior to Colin being born, I did not know that I was capable of loving anyone or anything more than I love my son. There is nothing that brings me more happiness than seeing him in the mornings smiling back at me.

Watching Colin grow has been the biggest joy of my life and I’ve been doing everything possible to cherish the moments I have with him. I know that one day I’ll be writing a blog post on his 18th birthday talking about how time has gone and that he’s now an adult. That makes me sad, but the impermanence of everything is what makes life beautiful.

Life this past year has been the most rewarding year of my life, but at the same time, likely the most challenging. In order to be a better father, I’ve really had to grow up. I’ve had to come to terms that being a parent means giving up a large part of your own life. While it has all been worth it, it has not been easy. It’s been a rollercoaster of a year with a lot of highs and a lot of lows, but I’ve finally gotten to a really good place right now.

I suppose now Colin is officially a toddler and not an infant anymore. There’s going to be a lot of fun developments coming in the next few weeks to months with his first steps and first words likely. For now though, this week and weekend is about celebrating the little guy that has brought so much joy to his parents and family. Happy Birthday Colin!

Another election day

It’s election day here in New York and it’s going to be a heated one. While it’s been more or less accepted that Zohran should walk away a winner tonight, there seems to be a large push for Cuomo and maybe a sliver of hope for anti-Zohran folks.

I’m not one of the folks who believes Zohran is an anti-American who wants to implement Sharia law (these are real ads I was served today). At this point, I do believe that he’s a good person that wants to try to make positive change for New York and the country.

With that said, I do have a real fear that these policies simply don’t work and will make things worse for New York. I have seen this script before in San Francisco and other west coast cities where liberalism goes too far and we lose a bit of common sense.

If elected, my hope is that Zohran can surround himself with experience and smart individuals who can help guide him to implement change within reason and common sense.

Doing less to get more

We had a great weekend. It was Colin’s first Halloween and while he like won’t remember what was going on, it was really fun spending time with him on a festive day. On Saturday, Sophia and I spent some time in the city and then hired a baby sitter so we could go out to dinner. It was a great weekend.

One of the key learnings in my first year as a parent is that I need to do less to get more out of my weekends. There were many months where I had tried to do too much with Colin. Whether that was being too ambitious with my day with him, or just planning way too much social events, or traveling too much.

My life has gotten significantly better the last few weeks when I have committed myself to doing less. For example, we can go out trick or treating with Colin but also realize that he does not know what’s going on and we should head back so he can play and get some energy out versus sitting in a stroller. We can also grab lunch in the city but need to be back by 3:30 for his nap or else we’re going to have a cranky kid.

Our weekends are infinitely less stressful once we’ve come to terms with the new reality and stopped trying to force things to feel like the pre-kid days. Things are not the same as they were before and likely will never be. After about a year, I’ve finally figured that out and have been enjoying our weekends more.