The (maybe) last bachelor party

Tomorrow morning, I’m heading up north to a small town with my high school friends to celebrate my close friend Mike getting married. It’s a mini-bachelor party for Mike. It won’t be a traditional one by any means as we’ll all just be hanging out camping and just enjoying being with each other.

We’re now 35 and we’re mostly through these bachelor parties and weddings. We have a few friends still single, but the classic age 25-35 wedding circuit is coming to an end. I’ll miss them in the sense that it’s not often that we get to get all the friends together. In fact, I’d wager that in all likelihood, we’ll have less than 10 more of these gatherings left in our life times which is sad to say, but it’s the truth.

We all grew up with each other and I’ve known these guys for over 20 years now. Some in the group have known each other for almost 30 years. It’s crazy to think but they’ve been a major part of my life since I went to high school. I’m beyond grateful that we are all still close and stay in touch.

Managing my calendar

I’ve been really struggling the last few weeks in managing my calendar. Prior to having a kid, I would usually just spend most of my day on calls and then suck it up in the evenings to catch-up on all the work to-do items.

Nowadays, I often don’t have the luxury of that evening time anymore as I need to put my kid to bed, get dinner ready, and then usually finish up with chores. Even with a nanny at home, having a kid effectively shortens my day anywhere between 2-3 hours that used to be reserved for catching up for work.

It’s been a hard transition for me and I’m now just starting to get around to making adjustments. This starts with managing my calendar a bit better. In this job, where my role is giving people money, everyone’s case is almost always urgent so my calendar fills up with calls quicker than I’d like.

There’s a simple fix here in blocking times out of my day to focus on work and not making any exceptions to those blocks. It’s the only way I can get real work done nowadays and unfortunately this may mean putting off calls to the next days or weeks. It’s not ideal, but it’s necessary for me to be able to do my job effectively. It’s definitely easier said and done though in practice, and I need to be more disciplined.

Dealing with growing older

Since Colin was born, I’ve been thinking a lot more about my time left on this planet. Having a kid has expanded my love for life multitudes over. With that, I’m also now thinking about my own death in order to try to maximize my time with my son.

Watching him grow over these last 5 months has been amazing but it’s also made me realize just how fast life goes. It feels like yesterday that we were just taking him home from the hospital. I reckon that I’ll be saying the same thing when I’ll be dropping him off to college in 18 years.

Separately from Colin, there’s a lot of other things going on in my life that’s making me realize just how old I’m getting. Dealing with Sophia’s Dad's health scare in 2023 was an eye-opening experience that our parents are getting older and won’t be here with us forever.

More recently, we’ve found out that my childhood nanny who lived with me from age 5 until 15 or so and has been part of my life for 30+ years is now leaving to go back home to Indonesia in June. She is in her 70s and has been in the United States for 30+ years without going back to see her own family.

We knew that time would come eventually as it would make sense for her to spend the remaining years of her life back home with her family. But she has built a great life here and presumably delayed the process as long as possible as she loves it here.

Given the dynamics of visas and her age, I highly doubt that she’ll ever get the chance to come back to the United States again. And knowing that, we know that this may be the last time that we’ll see her.

It’s a surreal concept thinking that someone who has been in your life for 30+ years will be saying goodbye for the final time. She was instrumental in taking care of me and my sister when we were young and we’re forever grateful for that. She was part of the family and I’ve been really sad at the thought that I likely won’t see her again for the rest of our lives.

Fathertime is real and finally starting to hit me hard in life for the first time. Unfortunately, this is part of life and just the beginning of a lot of sad things that will happen. It’s yet another reminder to enjoy the time I have and be as present as possible with the friends and family I have.

Nobody knows

I saw a Tweet yesterday with someone saying that Trump doesn’t know that words can have multiple meanings and he thinks a trade deficit means they are losing. I laughed but then realized that this very well could be the truth. I’d like to think that Trump isn’t dumb enough to not know why a trade deficit happens, but I have no evidence to the contrary.

In fact, he seems to have doubled down on trying to eliminate the trade deficit with each country. Of course, there’s a reason why we buy more goods from countries like Vietnam than they buy from us. Another Tweet I saw the other day said that this trade war is like “Hiring a house cleaner to clean your house, but then fighting with the cleaner so you can keep cleaning the toilet”.

The problem with all this is that no one actually knows exactly what Trump wants or aims to get out of all this. Even the countries who he’s negotiating with and has been open to negotiate.

My two simple theories: Trump thinks a trade deficit is bad for some reason and wants to eliminate said deficit. And/or he simply just wants to flex his power over the rest of the world for a bit because of his ego. Unfortunately both these things can still be true.

We can only hope that this does not continue for much longer. There is no one I respect in the business or investing world out there that says that a prolonged trade war is good for the country or world. Let’s all hope this works out.

Colin's first Giants game

I’ve spent few weeks writing about myself. I simply just have not had the energy or will to write much about work. I hope that changes again in the coming days or weeks and I can get excited to write about things I’m seeing in the markets or at work.

For now though, writing here is therapeutic for me. I don’t know if I or anyone will ever go back and read through everything I’ve written over the last 7 years. But it’s been meaningful for me to try to write something down publicly almost every day. It’s a very grounding experience and I’ll continue to just write what’s on my mind every morning I can.

This morning, the biggest thing on my mind is Colin. I had an incredibly special weekend with my son. Sophia had a quick trip to Seattle for a baby shower so I was alone with Colin all Saturday and most of Sunday.

Despite things being a lot harder without having Sophia, it was a special weekend for us. I made sure to take him out and see the world. On Saturday, I took him to Ocean Beach for the first time on a gorgeous day. It was exhausting as he got a bit fussy at the end of the day, but watching him hang on out the beach and taking him to see the water was a great memory.

On Sunday, I took Colin to his first Giants game. San Francisco did not disappoint with a gorgeous 70 degree day and the Giants also held up their end of the bargain with a bottom of the 9th inning walk-off win. He was a trooper the entire day and despite being confused and perhaps overwhelmed, he did great.

Colin is now 5 months old. It’s not lost on me that he’s growing up fast and this is a very fun period of his time as a baby. I’m doing my best to savor every minute I have with him.

Week off thoughts

I’ve had a great 4.5 days off this week. It was exactly what I needed to get my physical and mental health back to a good spot before a hectic month ahead. Most of February and March were particularly brutal for me with Colin combined with everything happening at work. I let myself get to a really bad state and I’m not proud of it.

On this past week - I spent most of the weekdays just relaxing. I laid in bed a lot on Tuesday. I ran errands with Sophia on Wednesday. I went to the spa on Thursday and relaxed for two hours before grabbing a nice lunch by myself. I played 9 holes of golf and got a nice lunch on Friday. I needed a lot of time to myself and I did just that.

I’m not happy to report that I did think a lot about work during the week. Sitting in the hot tub and the only thing going through my mind was work at times. I felt like slapping myself a few times.

This week has made me realize that I let my work seep into every other area of my life way too much. The stress of the last month came home with me, went to bed with me, and woke up with me. It consumed me nearly 24/7. I lost being present with Colin when I had time with him. I lost sleep thinking about work in bed.

It’s an awful habit and I’m ready to put that behind me. Work will be work. And I need to put better guard rails up to make sure I’m present. There’s only so many hours in the day and I need to start accepting that I don’t have the hours I used to prior to having a kid. If I don’t make changes, I’ll keep running into this issue of burnout which helps no one.

Tomorrow it’s back to work, but the main thing I want to make sure I do this month is start putting those guardrails back up between work and personal.

The "secret" to sleep

It’s hard to ignore what’s happening in the market right now with Trump’s tariff plan. However, especially in my week off, I’m choosing not to torture myself and aim to distance myself away from that as much as possible. I don’t need the added stress on things I can’t control.

On a much more positive note, I had the best night of sleep in perhaps the last couple of months last night. It wasn’t that I slept any longer than normal, but I just had some amazing good deep sleep.

It turns out that having a fulfilling and good day leads to a non-stressful bedtime. When you’re not tossing and turning with anxiety and thinking about things like work in bed, you usually sleep a lot better. That' parts easy and obvious.

The harder part is ensuring that I continue to have good fulfilling days and not go to bed stressed out. Making the life changes to ensure that I continue to do that is exactly what I need to figure out this week.

Just do nothing

Yesterday was a glorious day. After wrapping up work with a couple hours of calls in the morning, I logged off with no plans except to lay in bed and watch Netflix all day. I made it out of the house to grab lunch and had to take one 15 minute work call, but besides that, I spent the rest of the day doing exactly nothing in bed until our nanny left.

I can’t remember the last time I did something like that. It’s crazy to think but it must be many years. I’ve always been someone who needs to get up and do fill my day with things to do when I have free time. The script is usually the same when I have a free day - go exercise, run errands, check out a new restaurant, etc. If I don’t feel like I’m getting ahead, I simply just feel lazy.

Sometimes being lazy and relaxing is much needed though. It was evident yesterday as I fell asleep for almost 2 hours during the day out of exhaustion. I’m getting older and my responsibilities are growing, it’s about time I adjust my schedule to fit my new life. That means less activities and more rest so I can stop feeling like shit all the time.

First order of business is peeling back my schedule so I can simply just get more rest when there’s free time.

Weight off the shoulders

It’s amazing how different I feel today from yesterday.

First, the quarter is officially closed and we had a great Q1 as a company. Given the events over the last 6 weeks or so, I feel incredibly proud of what we accomplished. We had to work harder than we’ve done in the past with all the noise. I’m burnt out from the work, but at least I feel accomplished.

Second, I’m officially free for the next 6 days to rest and relax. My inbox and immediate to-do list is cleared, and I’m ready for some much needed time off. I’m going to do my best to stay away from anything work related for the week. Unfortunately I will need to make some progress with the move, but going to also try to limit my time spent there.

For now, I’m planning on just hanging out at home and being lazy. There are no more workouts for the week. I may get outside at some point tomorrow and hit some golf balls or grab food somewhere I’ve wanted to go, but it feels amazing with no schedule or plans right now.

I feel like an entire weight has been lifted off my shoulders and it’s a great feeling.

Week to get my mind right

The exhaustion really hit me hard on Sunday as I fell asleep while feeding Colin during his 7am feeding. Sophia could see that I was struggling and let me go back to sleep. She’s been amazing through the last few weeks and has been a supermom while I’ve been trying to keep it together.

The built up exhaustion from the last 5 months of being a father combined with the stress of work has been really hard. Add in a cross country move in a month and you’ve got a perfect storm. My anxiety levels have been possibly at an all-time high and it’s definitely made things worse. I had a horrible night of sleep last night as my mind spiraled.

I had decided to take the rest of this week off once the quarter ended about a couple weeks ago. I could sense that I was going to need some time away to recover, and I knew the sprint to close out the quarter wouldn’t be easy. Unfortunately, I didn’t think things would get this bad.

Needless to say, this time off couldn’t come earlier. My main thing that I want to accomplish is to rest and get my mind right. As such, I don’t have many major plans for the week and we kept the nanny to allow me time to focus on myself for a bit.

After some morning calls tomorrow, I think I just want to simply do nothing the rest of the day. I may sit in bed and stream Netflix all day. A day for me to do absolutely nothing sounds fantastic and something I haven’t had in a very long time. I hope the rest of the week will be similar mixed in with some time outdoors, some time reading, and some hanging out with Sophia and Colin.

I want to do my best to just tune everything out when it comes to work. I’ve never been good at unplugging even while on vacation or during my “paternity leave”. But this time it just feels a lot different. It’s time that I get away from my inbox and work for a few days and focus on making sure I come back energized. That’s the best thing for myself and Secfi. Prolonging my burnout isn’t going to do anyone any good.

Friday catch-ups

I had the late afternoon and evening with Colin all by myself yesterday and it was an awesome few hours. Every day I tell myself that I couldn’t imagine loving someone more, but every day it feels that I love him more and more. Fatherhood is really an awesome thing and it’s been the best part of my life so far.

It is a reminder that I need to have more times like this. I’ve been around a lot and have limited my travel to be with him as much as possible, but these years go by fast and I want to maximize my time at every stage of his life.

On the work front, I’ve got the entire late morning after 11am through the rest of the day blocked off to catch-up on work. I’ve got a mountain of things to take care of work wise and also personally. Fridays are some of my most productive days even with mixing in some personal things like going to the gym.

Most of our clients aren’t reaching out on Fridays and it’s the perfect opportunity for me to catch-up on everything and feel good going into the weekend.

Moving in 2025 and beyond

I’m feeling a lot better about the move than I did earlier in the week. I think I just have a ton of anxiety from the last time I moved to New York which was when I was 23 in 20213. A big part of that is that I had much less capital then and no knowledge of New York. While things are more complicated nowadays with a kid and a wife, as well as many more belongings, things are a lot less stressful 12 years later due to advancement in technology.

A huge part of that is just simply how convenient things have gotten. It’s the simple things that add up in these stressful situations like a move. I used a local ISP in San Francisco and canceled with just a simple email. I then booked internet through another local ISP in New York and was able to schedule an installation using Calendly. No more calling Comcast and arguing with them to cancel for 45 minutes and then having to drop off rented equipment.

Moving all our belongings including a car is much simpler in this day of the internet as well. There are just many companies that specialize in this and it was easy to read reviews online to book a couple companies. I was surprised at the level of customer service with these movers and some of them even had online tracking.

Of course, there’s still a lot of challenges. Most notably, it does take at minimum a week to drive from San Francisco to New York. So we’ll be without our stuff for a week to two weeks. That’ll pose challenges here in San Francisco but luckily I have my parents house as a last resort. It’ll be a bit easier in New York without a nanny and with Sophia and I taking the week off.

I am interested to see what the process will be when we decide to move back. Driverless truck drivers are something to look forward to. The truck will of course still need to refuel and/or charge. I know the technology is there or at least close to being there. I hope one day we’ll be able to move all our belongings faster and cheaper with a driverless truck.

If things got this much easier in 12 years. I can only imagine how much easier it will be in 2035.

Balancing micromanaging and freedom

The beauty behind working at a startup is that there is a lot of freedom to go out and do what’s needed to move the business forward. When I left PwC to work at Secfi, I felt a huge weight off my shoulders. There were more or less no guardrails or processes which was scary at first, but allowed me to thrive as I got to build things out my way and move quickly.

When people join Secfi, I tell almost everyone the same thing that this is their company and they have the ability to make a huge impact, and they should never be shy about chasing what they think will help move the business forward.

Of course, you do need to set some sort of bumpers so people don’t stray too far off course. For example, I’m always for people getting exposure to other areas of the business or other teams, but if they aren’t taking care of what they are hired to do then it will be a problem.

In addition, the team needs to also know that they need to own the decisions they make whether it works or not. People can experiment and chase projects, but if it doesn’t work out, I expect them to own it and figure out why they/it failed and move on quickly lest they burn too much time and money for the business.

On top of that, the staff needs to know when something is too big of a decision for them to make and know when to escalate things. There’s simply some projects and tasks too big for one person to solely make the decision on.

Over time, these things become natural for the team if you work on them. But they need to be worked on and people need to be coached through it.

New York official

My lease is signed and flight is booked. Sophia and I have started the process of moving my family and our belongings to New York officially.

I’m trying to manage my sadness of leaving San Francisco by getting excited by New York and everything it has to offer. In my almost 7 years since leaving New York, I’ve almost forgotten just how much there is to do pretty much everywhere.

Despite living in the city for almost 5 years, I barely even explored other parts like Brooklyn. I spent an hour last night doing a quick Google maps search of the surrounding area and was thrilled to see everything to do so close by. It will undoubtedly be a ton of fun living in New York again.

I’m especially excited to have coworkers again in the office. I’ve really missed the camaraderie of having coworkers. Zoom just isn’t the same and I just simply miss being able to sit down and have lunch with someone on the team and chat about life.

Having the team together where we can collaborate and grind things out together will be a huge perk and I plan to be in office at least 4 days a week to take advantage of that.

For the next few weeks though - it’s going to be a lot of planning and packing. I’m fortunate that we have the ability to pay for movers and make things just a bit easier overall. When I left 7 years ago, I packed all my belongings in boxes and had to take it to Penn Station in order to avoid a multi-thousand dollar move.

Fortunately, we don’t have to go through that again but moving a 6 month year old across the country also poses a lot of challenges. It’ll be a stressful few weeks but I’m excited to be on the other side of the move.

Excitement and anxiety

Sophia and I signed a lease for an apartment in Brooklyn starting May 1st. Moving back to New York is now a reality and we now need to start scheduling and coordinating the move.

I am happy that we found a place that we liked. However, I have quite a bit of anxiety from it. It’s a brand new build with active construction still happening on the higher floors. The building and amenities are still yet incomplete. In addition, we’re really rolling the dice on a new up and coming neighborhood in Gowanus.

In a worst case scenario, the construction could be more annoying that we thought. And the amenities that we’re paying for could not be in use for at least a few more months. Lastly, since neither of us have lived or spent that much time in Brooklyn, we could really be moving to an area that we’re not happy with.

On the flip side, we are the first tenants in a brand new apartment that would typically be out of our price range. It could be a really fun year at minimum and perhaps we’re going to love everything about the apartment and realize we got an amazing deal. We’ve never lived in a building like this and it was an opportunity that makes sense for us. It was a chance that Sophia and I were comfortable with taking. Time will tell but it does add to my anxiety level.

We’re also going through quite a bit of period of sadness right now. I know deep down that this is the right move, but leaving San Francisco at this moment is tough. It’s been fun watching my Dad interact with Colin and I’m leaving my family behind. Our closest friends are also here and going through big life moments as well and it sucks that we’re not going to be together for that.

All that said, San Francisco will be here and we’ll likely be back sooner than we think, and we’ll also visit quite a bit. Life moves quick and this is in all likelihood the last chance we’ll get to live in New York City before Colin starts school and we try to set up a homebase. Soon enough my sadness will turn to excitement.

The move is going to cause a lot of stress especially with a 5 month year old so I really need to make sure to get my mind right in the next couple of weeks. I plan on spending this week focusing on closing the quarter strong and then taking most of next week off to get my mind right. I could use a break especially before going into a stressful time that involves moving my family across the country.

Consumer businesses

I’m a sucker for consumer businesses as I love cool products. No, I’m not that Apple fanboy that lines up for the new iPhone or anything, but I do love great products that make my life better.

I love my Hyperice Hypervolt massage gun. Since I bought it almost 6 years go, I’ve used it almost every day and it’s great for my sore muscles. I love my athleisure attire from Vuori and 7Diamonds. My AER backpack which has a compartment for my gym shoes has been my backpack for over 8 years.

Despite spending almost my entire workday primarily working on and investing in B2B companies with no tangible products, I always love when a consumer company comes across my desk. They are just simply a lot of fun to learn about.

The unfortunate part is that they’re typically much harder businesses than B2B given you actually have to manufacture a good or product and run a supply chain. I have the ultimate respect for the folks crushing it out there in a consumer business that manufactures products.

If I ever went and started a business, my heart would say do something for consumers but my brain and mental health may say to stick to finance and/or B2B.

Degenerates and gambling

I love this time of year as the NCAA Tournament kicks off. Unfortunately I haven’t had time to watch any of the games this morning, but I plan to get a healthy dose of basketball this weekend.

I do not gamble on sports at home solely for the fact that I know I would love it too much. I love sports and gambling separately and when you combine those two together, it’s a bad habit that I don’t need in my life right now. I save most of my degenerate behaviors for when I get the chance to go to a casino or Vegas which is maybe once a year if I’m lucky.

It is hard to ignore just how many people do gamble on sports on a daily basis. I have many friends who have apps and gamble almost every weekend either through a bookie or an app. It’s only going to grow larger. It’s a trend I stay close to and I’ve taken a few positions in my portfolio for that.

There’s a ton of startups banking on this trend as well. Gambling is now effectively open in Robinhood. It’s the age of the degenerate.

Being present with Colin

It’s an incredibly special time in my life right now with Colin coming up on the 5 month year old mark in a couple weeks. He’s grown so much in the last months and will continue to grow very quickly. He’s rolling and cooing like crazy right now. It’ll be a matter of time until he’s sitting up and crawling.

Of course, I wish I had more time with him everyday. I’m loving the relatively short windows of play time I have with him every day but I’m doing my best to be as present as possible whenever I’m with him. I do my best to wake him up and feed him in the mornings, and then get a bit of time with him before I leave for work. Then I look to get home early and try to get as much time with him before he goes to bed every day.

These days are long and it’s a bit of a slog. I’m perpetually tired, but I know that I’m going to miss these days when they are gone. And they will be gone quicker than I think. I can’t stop time, but I can control how present I am during these special moments. It’s a great reminder for me to put away my phone and turn off the TV, and focus just on enjoying every moment with him.

2050

I remember when my Dad showed me the internet through AOL for the first time when I was around 5 years old at his office. He had a Gateway computer and I want to say it was Windows 93 as the OS. It was a pretty remarkable experience. I don’t remember much from when I was 5, but I do remember that day vividly.

He logged onto AOL and showed me a chat room. I remember him messaging someone saying “Hi Flowers”. He quickly regretted that decision and X’ed out of the window and said it was for adults. It was a funny moment especially in retrospect, but it was the first time I fell in love with technology.

I am now 35 years old. If I’m lucky, I’m somewhere between a 1/3rd and halfway through my life. In 2050, I’ll be 60 years old and again, if lucky, I’ll be retired and heading in my glory days.

With the way technology is rapidly advancing, I’ve been doing a lot of day dreaming on what that future could look like for me. I joked with my friends that if there was a self driving car to take me to Lake Tahoe in the future, I’d be satisfied. But maybe I’m thinking too small given how fast things are advancing.

Is it really that farfetched that in 25 years an average joe like me could go to space? Perhaps air travel becomes so economically viable that instead of driving to Lake Tahoe in a driverless car, I could fly there in my hovercraft in less than half the time it takes. We all know medicine is getting better - I wonder what the age expectancy will be by the time I’m 60.

I don’t know what the future will hold. But I like to remain optimistic that my 60s will be better than my Dad’s 60s. And my son’s 60’s will be a lot better than my 60s. With the way things are growing, there is a lot to be optimistic about in tech despite perhaps all the negativity and doom in the news right now.

Monday musings

I got to the office just before 7:30am today which may be a record for a Monday. I’m not a morning person and have never really been one, but unfortunately having a kid makes sure you’re up at the crack of dawn every morning.

It’s been a struggle for me, but it hasn’t been all that bad. It does feel incredible being productive in the mornings and starting my days off right. My days feel a lot longer as I’ve had a full day by the time Noon hits. That’s much different than our past where on the weekends we’d try to sleep in sometimes to 9am.

This isn’t rocket science, but I’ve felt a lot better with everything recently these past 5 days or so as I feel that my sleep has gotten back to a decent spot. I’m more positive and I hit the ground running in the mornings versus slogging through. I’ve just got to be deliberate with my sleep nowadays.

On the markets - it’s almost the end of the quarter which means that it’s time for me to review my personal balance sheet and figure out if I need to make any adjustments. It’s always a lot more fun to do it when the market goes up then when it goes down and like almost everyone else, my net worth is going to be less than it was at the end of 2024.

On the work front - we have 2 weeks until the end of the month and we have a big push so we can start the year off strong. I need to stay laser focused and grind it out for a couple weeks and then make sure to take some time off to rest and recover.