New York, New York

Admittedly, I’ve been really sad to leave San Francisco. My family is there. My best friends are there. And my golf game just started getting good.

But holy hell I love New York. I’ve been in town less than 12 hours and I can notice that my energy levels are on a different level. The sheet amount of quality food everywhere is just mind boggling, even for someone who previously lived here for 5 years.

I spent a lot of my plane ride figuring out where and what I wanted to eat while I was here. My fat ass even went to 2 restaurants last night, Fish Cheeks and Szechuan Mountain House. I just had to sneak in two of my favorite spots. Of course, that list has slowly just grown in the last 12 hours. Walking around and seeing new spots I want to eat at is my favorite thing to do in New York.

It’s also incredibly energizing being here with the team in-person. Unlike San Francisco, the office culture in New York is thriving. I’ll be checking out some places to move the team to this afternoon.

It’s going to be sad leaving San Francisco, but being here in New York has got me incredibly excited again. I can’t wait to be back.

Being present

Sophia and I drove up to Lake Tahoe with Colin on Thursday and spent a long weekend out there. It was our second road trip with Colin and like the first, he was great pretty much throughout.

Colin is getting to a really fun age right now. He’s smiling more and starting to communicate via coos. He’s not crying as much and he interacts with us a lot more nowadays. He’s also sleeping nearly 10 hours a night leaving Mom and Dad a lot more rested.

By far the most common parenting advice we get from friends and strangers is to enjoy everything now as they grow very fast. As I sit here on the eve of Colin’s 12th week birthday, I can attest that things are moving very quickly.

I can’t stop time or make things go slower, but what I can control is being present when I’m with him. It’s easy for me to do emails while playing with him or have the TV on in the background. Those are obviously horrible habits and I want to be conscious about being present whenever I’m fortunate to have time with Colin.

Productivity with a baby

I’ve been trying to find ways to be more productive in the last few weeks. With a new child, I want to be home by 6pm almost every day so I can feed him and put him to bed. After not being with him all day, this is a special time for me and I’ve made it a point to be there.

This timing has clashed with my previous preferred schedule. I’m someone who loves working into the evenings and stretching my afternoons. I’m on call most of the morning and early afternoon, and I don’t get a chance to be my most productive until the late afternoon and evenings.

With a more condensed and busier schedule now, I need to find more ways to be productive and that means I need to peel back in other areas of my day. Unfortunately, this means my personal time gets shorter. I no longer have the luxury of taking long lunch breaks and having leisurely workouts at the gym. Previously, I could make up for that lost time in the evenings but that’s no longer a possibility.

I also need to peel back the amount of calls I have and sticking to bigger blocks to focus on getting stuff done. This will also be hard given that I seem to live most of my day on calls. It’s going to be a big adjustment for me, but one that needs to be made to keep my sanity and work-life balance in check.

Reset days

I blocked off my entire calendar today to give myself a “reset day”. I had done my best to get caught up on everything on Monday despite the holiday and was hoping to get caught up on my to-do list on Tuesday.

Unfortunately, I spent most of the day in calls and meetings. My checklist only grew bigger and I wasn’t even able to get to the most important thing I wanted to do. The writing was on the wall that I needed a day to catch-up on things.

These reset days are great for me as it gives me most of the day to solely focus on getting work done. I’ve moved or canceled nearly all my meetings except that pesky one hour of calls that I need to do.

I feel good and excited to get through everything. Note to self to schedule more of these reset days in the future when things get too crazy.

America 2025

The Trump Presidency has officially arrived and if there’s one thing I’m certain of is that this will be a much more interesting political climate than the last four years.

My stance going into the Trump Presidency is to remain positive and hope that he proves me wrong. Like it or not, he’s our President and there’s going to be changes that take place. I hope these big changes promised actually turn out to be the right thing for this country.

On the positive end, it does seem that Trump is aligning himself with much more positive advisors. Controversial as they may be, I’d rather see Trump advised by Elon rather than Steve Bannon. There is hope that he’s learned a lot from his last Presidency and he’s much more effective this time around to enact positive change.

On the scary side, Trump’s divisive rhetoric is worrisome. I don’t know what Elon’s intention was with his salute, but it was not great for the optics one way or another. I fear that we are once again giving people a platform for racism and xenophobia.

I’m an optimist so I’m going to remain hopeful for our country.

Living life with Colin

I’m feeling a lot better after taking a few days off through the long weekend. On Wednesday, Sophia and I decided to go to Carmel a bit early and roll the dice on two nights away with Colin. We really needed to get away for a bit and break out of our normal routine.

We had worried about Colin not adjusting well, but he adapted like a champion. He slept his normal hours and didn’t miss a beat. It was a test case to see what traveling with Colin would be like and the results were overwhelmingly positive.

We spent most of the trip doing casual walks around town and also visiting the aquarium one day. We spent more time in our hotel room than we’re typically used to on vacations because of Colin, but just getting out of our apartment and living a bit was really nice.

For the first time since Colin was born, things felt a bit like our old life but with the added benefit of showing Colin the world. While I’m sure he wasn’t too cognizant of what was happening the entire time, he’s been a lot more responsive and communicative lately. Bringing him with us on our adventures has been a treat.

Sophia and I are already talking about where to take Colin next. We’re going to be sure to take advantage of the baby years and travel as much as possible.

Tough decisions and conversations

Whether it’s deciding to let someone go or pulling the plug on a project, one of the biggest lessons I’ve learned from my 6+ years working at a startup is that tough decisions need to be made quickly and decisively.

The natural inclination for people is to delay or procrastinate that decision. It’s natural as it’s often easier to push things back and hope things fix itself out in the long run. It never does unfortunately.

For those reasons, it’s best to just make the decision and get it done. The conversations are never fun. There’s a human aspect to all this and often times these tough decisions impact individuals directly. But for the best of the company and that individual, it should be done quickly rather than a death by 100 paper cuts.

Time for a recharge

I’ve been running on fumes since December. I kept telling myself that I’ll take some time off when things slow down in January, but I’m sitting here mid-January and so far it’s been another busy 2 weeks of work.

Sometimes you need to hit rock bottom to realize things and unfortunately that’s what happened to me yesterday. I woke up exhausted and just generally negative about everything. I struggled through the day with some tough anxiety.

Simple tasks were just much more difficult and it was hard to focus for long periods of time. My run that serves as a stress killer and quick fix ended up being the most I’ve struggled in a run in months. Rock bottom indeed.

The toll of a newborn along with a stressful job doesn’t make things easy. Being a first time father adds fuel to the fire. Going forward, I know I need to do a better job managing my time and schedule. It’s just not sustainable to do what I used to pre-kid anymore.

For now, I’m going to take the rest of the week off after tomorrow morning. And possibly some time next week as well. There may not be a better time given things are slow and I need to take advantage versus creating more work for myself to stay busy.

It’s time for a recharge. I’ll be a better Dad, husband, and colleague once I do.

A sense of normalcy

Sophia and I had a fun weekend that we’re unfortunately paying for now. After over 2 months of new parenthood, we decided we needed a break.

Sophia had a girls dinner on Friday night and I had the guys over for drinks. It was a nice escape for Sophia and it sounded like a fun night. For myself, I had Colin still but it was also nice just having the guys over for drinks and watching football like we normally do.

On Saturday, Sophia and I hosted our “annual” crab feast for everyone. We had 8 friends over to our place for an afternoon and evening of crab and drinks. Colin was the star of the show and it was great to have all the friends over hanging out with him.

Having a kid there still makes things different but perhaps for the first time since Colin was born, it felt like things were “normal” as in the way things were before Colin was here. Of course, part of our journey now is understanding that there’s a new normal and getting used to that life style.

And yes, we’re paying for it today. Even with early bed times, the lack of sleep adds up. Spending the entire weekend socializing makes the next couple of days that much harder. For that reason alone, we may not be having many of these weekends anymore.

For one weekend though, it was a nice break.

Triaging the right partners

When you work at a startup, time is the most valuable resource. There’s just simply too many things to do at once and you need to prioritize accordingly. It’s always going with the highest value projects and deals.

We’re always trying to make sure we triaging the best deals. There’s always a trade off between amount of work and deal impact for us and finding that balance can be hard. Doing a sizable deal into a target company is always ideal, but if there’s complications that’s going to require a lot of work, we need to weigh that. Same goes for any projects we take on as a company.

One area that I need to really get better with is making sure we triage the right partners. Put simply, there’s some partners we work with that are great and worth the effort of building a relationship. They see the mutually beneficial aspect of working together and we help each other.

There’s others that are purely transactional and only come to you when you need help. Like in life, you don’t want to be friends with that person that only comes to you when you need something.

We’ve historically cast a big net here at Secfi in terms of our partners, but we’re at the point where it’s time to pick and choose better “friends”.

Losing your independence

So far one of the hardest things about being a parent is coming to terms that I simply can’t do much else besides parent anymore. There’s no going out to dinner anymore or grabbing a drink with friends after work. Well at least not often.

In my 34 years on this planet, I’ve lived mostly independent doing what I want. Things changed a bit once I moved in with Sophia, but still if I wanted to grab a drink with friends, it would just need to be a simple text message.

That all goes out the window once you have a kid. As much as I’d love to try this new restaurant, Colin needs to be in bed by 7:30pm to ensure he has a good night sleep. We could try to do an early dinner at 5pm and bring the kid, but it’s not the most pleasurable experience brining a 2 month year-old to a restaurant in the fussiest part of the day.

Sophia and I are trying to decide if we want to take a quick weekend road trip to Monterey in a couple weeks as well. Normally, this would be a dream weekend for me to get away and do something different. But of course, we’re thinking twice about doing it given that we now have a kid.

It’s a tough transition for sure and I’m still getting used to it. Seeing my son smile at me though makes it all the better. At least I have that to look forward to.

U.S. Digitalization in 2025

I spent over an hour at the Post Office today applying for a passport for my son. I suppose in the grand scheme of things it wasn’t the worst experience or the biggest time suck, but I showed up on time for my appointment only to wait 45 minutes before being helped.

As anyone would guess, the application process was filled out on paper and we had to print everything to bring to the post office. Once there, the post office worker had to hand print more things to finish the application. When I left, I could tell her was preparing the application to be mailed to the Government.

This is the year 2025 in San Francisco nonetheless and we still have yet to find a way to digitalize passport applications. Of course, this isn’t the only example of where our Federal, State, and Local governments are severely behind in tech.

I have no interest in helping fix the government’s issues, but I imagine that with proper incentives in place, there would be many entrepreneurs who would step up to fix these antiquated systems and processes.

The year of the degenerate

Life moves fast. I can’t believe it’s already 2025 now. I remember sitting in a management team offsite about 3 years ago outside of Amsterdam with the team. It was Q1 2022 and we were planning for the potentially bumpy road ahead.

Like everyone else, we didn’t realize just how bumpy it would be. The first interest rate hike was on March 2022 and like that, the startup and VC market started to grind to a halt. The last 3 years in VC and startup land have been tough. Valuations dropped significantly and the IPO market has been largely closed.

It feels like everyone is chomping at the bit. We have Bitcoin trading at near all time highs and lots of people seem to be having fun gambling with Memecoins. The degenerates are out in full force in crypto world. That has yet to translate to the startup/VC world and retail stock trading.

I expect that to change in 2025. With the IPO window seemingly heading for an opening shortly, more money will start flowing to the pre-IPO world. People are sitting on their hands ready to deploy capital.

The retail stock trading world seems also ready to participate. While the public markets have largely been held up by the largest companies, I expect more money to flow to growth and smaller cap companies this year.

It’s going to be a year of the degenerate. Everyone can be a trader and people are looking for a good excuse to gamble.

January

I used to think January was the most depressing month of the year. The fun of the holidays is over and winter is in full force. School and work is back in session, and it’s dark and cold. Nowadays, I love January as it’s a reset month for me.

With the holidays behind us, I use January to get back on a good healthy schedule. I eat better, I exercise more, I drink less, and I try to sleep more. My body gets a nice reset.

January is also a time to get back to a routine. With the holiday craze with travel, family, friends, etc. you lose track of time and it’s all a blur. In the new year, I get back to a much more predictable routine.

It’s also a good time to take a step back from work and look at everything we accomplished in 2024. We’ll celebrate our wins and figure out how to learn from the losses. In the heat of things, it’s difficult to really take a step back and look at things from a high level.

Lastly, it’s a great time to plan for the year ahead both personally and work wise. I start to get more excited about life during this month as I start to look ahead to everything that’s in store for us.

Bring it on 2025

I wish I could sit here saying that I’m feeling refreshed, but truthfully I am exhausted from life and work right now heading into the first weekend of 2025.

It’s been fun having the in-laws here, but there’s been very little downtime with them and Colin. I had a pretty good holiday season, but with a lot of activities also comes a lot of stress.

On top of that, we’re working through the constant ups and downs of a 2 month year old newborn. We have some amazing days and nights, and then some just brutal ones. Last night was one of those brutal ones and needless to say, I could use a nap this afternoon.

Lastly, work during the holidays are much more stressful than I had wanted. I didn’t get those magical couple of weeks of rest that I was hoping for.

Regardless, life goes on. For better or worse, this is likely to be the new normal for me. But nothing worth it in life is easy.

I’m going to have to be better across all fronts in 2025 — more unselfish, more disciplined, etc. It’s a new challenge, but one that I am excited to take on.

For now, I’m hoping to take January as a nice transition month for myself and Sophia. Things should slow down a bit for work and Colin will be starting to hit that age where things are slightly more predictable. It’ll be a good month to get my life back in line.

2025 Goals

If last year was the year of getting myself right and being selfish, this is the year of focusing on my family. Knowing that I’m going to be absolutely swamped with the move to New York while trying to learn how to raise a child, I want to keep things simple. It’s a transition year for me and my family, and the big thing is to be present and not take on too much.

Be Present

I hate to admit it but I’m addicted to my phone. It’s not just social media but also emails and Slack. I’ve caught myself emailing while feeding and playing with Colin. And I feel like shit. My first goal for 2025 is to be present and put away my phone when I’m with Colin. These are special moments that won’t last forever and I want to make sure I’m here for it.

Be more Patient and Chill Out

If the first two months of Colin’s life is any indication, my known impatience is heading to unprecedented levels. The lack of sleep and personal time has really made me a much less pleasant person to be around. I can sense it and I’m sure Sophia and others can sense it as well. I need to become a better partner and friend in 2025.

That means chilling the fuck out a bit more and becoming more understanding. Parenthood is hard and I need to be better when it comes to being a partner.

Teach more

One thing I’ve learned about myself in the workplace is that I’ve become much more of a boss rather than teacher. The last couple of years has required me to step up more and grind out more work. And my focus on developing my team has slowed down a bit. I want to flip that in 2025 especially as I start becoming a regular figure in the New York office.

For the better of everyone and Secfi, I want to make sure to become more of a teacher in 2025.

2024 Goals in Review

I don’t really believe in New Year’s resolutions. They are things people say and usually break after January. Rather, I believe in goals which are things that are achievable over the course of a year if you set them and put your mind to it.

Last year I set 4 goals and I’m fairly proud of how they turned out. Diving into each specific.

Become conversational in Mandarin

This one was probably my biggest miss in the year. After taking a class in 2023, I vowed to try harder in 2024. I continued my Duolingo lessons but I wasn’t committed. I adjusted course a bit in December and decided to start the lessons over again with a focus on becoming more conversational rather than trying to score in Duolingo which has helped.

However, as I sit right now. I know quite a few words and can understand tidbits. But I still struggle to actually converse with anyone in Mandarin. I give myself a D here.

Get sleep and feel good again

I wanted to start feeling healthy and good again in 2024. My transition from early 30s to mid 30s was rocky to say the least.

I got my sleep at least under control in 2024 and slept more. I drank less and attended less events than I have done in the past. Overall, I’d give myself a B here.

Be selfish

This was the year that I was going to be selfish with Sophia and try do as many things as possible for ourselves before we had a child. Sophia and I did travel quite a bit and we were able to focus on ourselves. Of course there’s always more fun things to do in the world, but given everything, I’m happy with the way this turned out and give myself a B.

Start exploring cash flowing businesses

For my professional development, I wanted to start learning more about cash flowing businesses as a potential next step. Perhaps I would run a side business in the future or buy a business when my time at Secfi comes to an end.

I’ve spent a good amount of hours reading about the various kinds of business and the challenges small business owners face. I’m proud of the work I’ve done here. I’ve gotten myself a good mental model of what I’d potentially be looking for if this were to happen.

I still want to learn more, but I’m happy with the work I’ve put in and give myself an A.

Life is good and unfair

I’ve been catching up with a lot of old friends over the last week. My best friend asked me today if I thought my 2024 was my best year.

It was a hard question to answer, but I think with the birth of my son, I’d say it defaults to being a yes. There is nothing in the world I care more about than my son and I will do anything for him. All that said, it’s been far from a perfect year as we’ve dealt with a lot of bad along with the good.

My father in-laws health and recovery from the stroke has been less than ideal. We had hoped he would be further along in his recovery, but brain injuries are difficult and unpredictable. We’re overjoyed to have him here with us still after such a big injury, but also realize how fragile life especially with our aging parents.

On another front, one of my good friends also told us yesterday that her younger brother has brain tumors. It was absolutely devastating to hear as he was a survivor of pediatric cancer. It is heartbreaking on so many levels and hearing stories of a 30 year old who has dealt with so much in life already talking about his potential early death really took a toll on me.

In a year of so much joy for me with bringing Colin into this world, I also realize just how fragile life is. Life is just unfair at a times. Horrible things happen to good people who deserve it the least.

I am grateful for everything I have in life and this holiday season, I’m counting my blessings. It’s important to remember that nothing in life is guaranteed and we need to live.

Colin's first Christmas

It was an exciting last few days with Colin’s first Christmas. We spent Christmas Eve at my Dad’s house with the in-laws in town as well. The whole gang was together. Most of my closest family members were there and as expected, Colin was the star of the show.

He did great spending the day at Grandpa’s house and enjoyed being held by pretty much everyone. Watching my Dad get excited to hold Colin was a moment I’ll always remember. It was a special time for sure and one that we’ll remember.

It was also an exhausting few days. Our worst comes out when we’re tired and I can’t say I was the best version of myself at times. The sleep debt adds up over time. Once you add in social events and alcohol to the mix, and it becomes a cocktail of exhaustion.

I finally feel a bit more normal today after getting some decent rest last night. I was able to get some work done this morning and I’m going to try to get a quick workout in after lunch. Work seems to be finally slowing down and we can see the light at the end of the tunnel.

My hope is that by Monday we’ll be completely wrapped up for the year. Then I can focus on recovering and taking a break. I’m clearly tired and burnt out and I need some time so I can be the best version of myself again.

The Holidays

The Holidays are always a mixed bag for me. The work, travel, and family stress can definitely add up in this period. It’s also been a time of personal loss for me as my mom and grandmother both passed away right before the holidays during my childhood.

Despite all that, I’ve always loved Christmas. Some of my fondest memories as a child were around the holidays. I loved decorating the Christmas tree every year. I loved going downtown with my Mom to all the fun holiday shops. And I especially loved getting a lot of presents every Christmas.

This year, we have my in-laws in town which has been fun in many ways and stressful in other ways. My father in-law’s recovery from his stroke last year has been up and down. It’s sad to see them in this state, but at some point, we have to just be happy that he’s still here after such a big stroke.

We’ve had a lot of fun. Having our families hang out has been a special time for all of us especially with the newborn. I also really enjoy taking them out to places that I love in San Francisco. But yes, nothing is easy nowadays with aging parents and a newborn.

This year especially I’ve been really relying on optimism and my meditation to get me through. I’ve had to be more patient than ever before which is one of my weaknesses. It’s a special few weeks for our families and I want to make sure to focus on all the positives as we don’t know how many more of these times we’ll have again.