Time for a break

The signs that I need a break started coming out a few weeks ago. The all familiar signs which include:

• drinking much more coffee than normal during the workday

• taking much longer to finish tasks than usual

• frustration with pretty much everything and everyone

The list goes on and I’ve been through this so many times over the years at this point. Luckily the end of the quarter is near and with the 4th of July it becomes a natural time to really unwind.

It’s been a tiring year with my move to New York and a baby to care of. Work has been going well, but it’s always been exhausting. Top of mind right now is making sure I take the majority of next week to unwind and really recharge.

Early career moves

I had a fun night out with some old friends from PwC. I left the firm almost 7 years ago to this day and I spent 5 years at the firm, so at this point I’ve been gone longer than I was there. It was yet another time flies moment when I realized that.

I was excited to see them and I’m glad that we all remain friends to this day. They have all advanced in their careers and have moved up the ladder at the firm. My closest friend who I met during my internship in college and started at the same time is now close to making partner at the firm. He’s on track to becoming a lifer at PwC and he still loves the firm.

Obviously, I decided to take a different path than him and that was the right decision for me. I do think what my life could have been if I stayed, and I do think I would have a good life. But ultimately it was the right move for me to move on and do something different. Building something that was more like my own was what I needed in my life and career.

All that said, I am incredibly appreciative of my 5 years at the PwC. While I gave a lot of my life and time during my 20s to the firm, I truly believe I got just as much out of it. My years there set my career up for success and I learned a ton. While I personally don’t recommend staying at a large firm too long, it was a great place to be in the early part of my career.

Zohran-mania

Zohran Mandani pulled a shocker in the NYC Democratic primary yesterday beating out former Governor Cuomo. As someone who just moved back to New York, I’m just learning about the race and Zohran.

It seems that Zohran just ran an amazing campaign that put himself out there and aligned his messaging with the people. He campaigned on things that lost the Democrats the election in 2024. He was personable and approachable, and he’s very young. He was the anti-Cuomo and Trump.

Now I’ll be frank in that I don’t necessarily agree with all his policies. I remain skeptical in that they will actually work and I fear that he is the classic case of someone who says a lot of things, but nothing actually gets done.

All that said, I’ve grown to actually like the guy in my limited knowledge of him. At least on the surface, he seems like a good person who actually cares about people and wants to make a positive change. If he does indeed become Mayor, I hope he tries to enact change while ensuring that his policies are well-thought out.

My fear is that this is another situation like what has happened in San Francisco the last few years. But I remain hopeful that he can be someone that is different.

Can't escape the local politics

The last few years of local San Francisco politics has been tiring. We dealt with a handful of politicians that lacked common sense and it sent San Francisco into an awful few years especially post-COVID. Just as things started to turn around, I of course decided to move to New York.

As such, I’ve found myself in yet another brutal local political situation. With corrupt Eric Adams leaving office, we are now left to choose between Cuomo and Mamdani. I’ll be honest in that I just don’t know as much about this election given I have been in San Francisco.

My high level views are that Cuomo is that crafty politician that got things done, but was creepy and used his power to get away with being a creep. Whereas Mamdani is the classic young progressive who appeals to the younger generation by saying a ton of things that is just downright not going to work.

I suppose I still identify as a left leaning progressive and I welcome change, but I have also seen what happens first hand when these changes are not well thought out and we don’t analyze second order effects.

This ranges from common sense situations such as not prosecuting crime. Yes, that is unfortunately going to welcome more crime. We saw that in San Francisco. But it also extends to progressive policies such as raising the minimum wage to $30 which Mamdani wants to do.

Yes, I want people to get paid more and live better lives. But we perhaps have forgotten that many small businesses cannot survive running on a $30 minimum wage.

Again, some of these things Mamdani is saying sounds great. Fast, free buses. Freezing rent increases. I can see why young people like him. But I’m incredibly skeptical that any of this will happen. He sounds like an inexperienced individual who may win the election by saying a lot of things that just won’t work and we likely will be worst off from it.

I don’t have a vote in this election given when I moved, but I can see why New York is nervous right now given the two options.

Grateful

I’m feeling very grateful on this Monday after a great weekend with friends and Colin.

We had friends from San Francisco visit us and Sophia and I had a nice night out in Williamsburg. I almost fell asleep at the bar after dinner, but it was a fun night regardless.

On Saturday, I hung out with another old friend in town from Seattle and we had a great day hanging out at the pool with Colin. Despite probably being able to go to bed at 8pm, I decided to go out in the city and grab dinner. It was my first actual night out in Manhattan since moving back.

Life is obviously much different nowadays. Even without Colin, I’m not sure how much I’d still be going out or even if I can make it much past 10pm anymore. But it was great to just have a night out like the good old days and see old friends.

After a nice morning jog, I’m back at the grind for a bit. It’s going to be a tough week and half as we close out the quarter, but things are looking real great. Quarter-ends are never fun but the end of Q2 is nice because we have the 4th of July weekend. and I plan on ensuring our team takes at least a few days off to recharge.

Going international

It’s that weird Friday after a Federal holiday where it doesn’t really feel like a work day, but it is. I just dropped Colin off at daycare and it was pretty much empty except for one other baby. I need to make a note to myself that perhaps we should just make a long weekend out of this next year.

I worked the first half of the day Thursday and then took over baby duties in the afternoon. It was far from a half day off though as I just felt like I was basically working on my phone while also having to take care of Colin. But we made the best of it.

I’ve been doing a lot more work with non-US folks lately. It’s been really fun meeting people from all over the world from Australia to Dubai to nearly every country in Europe. Working internationally has it’s benefits for sure, but it also introduces a hell of a lot of complications.

Regulations, security laws, and tax laws are not fun to navigate through. Luckily most of the regulatory is covered as we’re based in the U.S. and don’t have a home base in any of these other foreign countries. However, the tax and security laws are a headache.

As first steps, we’re building out a good set of tax advisors and attorneys in each jurisdiction. It’s a tedious process and quite expensive, but we need to be sure to cover ourselves. Being on the right side of regulatory has always been our stance here at Secfi and we don’t plan on changing that.

Juneteenth

It’s Juneteenth and a Federal holiday. Unfortunately I’m quickly learning that these holidays aren’t really days off for parents as daycares and nannies are also off meaning the kids are home. It’s great to spend time with Colin but a Thursday “day-off” doesn’t mean the work stops unfortunately.

In world news - the situation in the Middle East is intensifying and it’s a bit terrifying to see where this will go. It appeared that the Trump administration was initially trying to stay out of the Israel-Iran conflict by publicly stating that the U.S. was not involved.

Just a few days later though, Trump seems to have injected himself squarely back into this. It’s pretty obvious to me that the unexpected welcome response from most of the west in regards to Israel attacking Iran is an open opportunity for Trump. If things go well, he’ll undoubtedly look to take credit for organizing the whole thing.

The one thing I do agree with Trump on is that we need a long-term solution here. Israel and Iran exchanging missiles and attacks every other month isn’t driving much stability either. I don’t know how this will all end up, but I hope this isn’t another conflict in the Middle East that the US has to get involved with.

On this day, I do need to remind myself of the progress that we’ve made as a country. It’s not a perfect country, but it’s my country and I still remain optimistic that we will make progress to bettering the country, albeit with a few bumps in the road.

End of quarter

End of quarter is always a tough time for us. In our world, naturally a lot of deals happen at the end of the quarter because of changing 409A valuations and perhaps a mental block for people to get something done. Yes, the metrics matter a bit for us, but it’s a bit different than a SaaS startup trying to meet their goals.

So we’re at the point where everything is a sprint and everyone is at capacity unfortunately. It’s not a fun place to be but it’s the reality of the job and at least it’s expected. For myself, I’m trying to make sure to prioritize accordingly.

There’s only so many hours in the day and while everyone thinks their needs are urgent, some things take priority. That’s easier said than done when everyone wants to hop on a call as soon as possible in this world. Priorities are priorities though and it’s important to keep our sanity as the same time.

I’m looking forward to a nice long extended period off after the quarter end for the 4th of July.

Father's Day

My first Father’s Day weekend was exactly what I needed.

We had a lazy Saturday morning and after a quick workout, I went to the city to eat and explore solo. Sophia had a friend come over and it was rainy so it was a great opportunity for me to have some alone time. Exploring the city and finding amazing things to eat was one of my favorite activities when I first lived in New York.

I ate lunch at one of my favorite restaurants in the city, Szechuan Mountain House. And then walked through the East Village and Chinatown for a bit. I was able to sneak in for a quick massage and then brought some food home for dinner. I cooked a delicious seafood feast for us.

On Sunday, Sophia let me go golfing. I’ve always loved golf, but I had an especially great time as we played a money game. Making things competitive made things a lot more interesting especially on a long and slow round. It was a bit of a reintroduction to New York golf as we had a 5 group backup and teed off 30 minutes late.

The best part of my Father’s Day was coming back and seeing Colin though. After I was gone all day, he was especially excited to see me and was being amazing. He was laughing and reaching for me, and all the Father’s Day emotions really hit me then. As great as it was having some time to myself this weekend, I love being a Father and being around Colin.

Fatherhood hasn’t been easy. Even having a relatively easy kid like Colin has pushed me significantly. The adjustment period has been a challenge for me. On top of that, I can list many more complaints about being a parent. However, the pros vastly outweigh the cons and being a Father is the best thing I’ve done in my life.

Being present

I have a friend who told us that she doesn’t schedule any social events for Friday as she’s just too exhausted by the end of the week with a young kid. I’m feeling that nowadays unfortunately.

With all the craziness in the world right now on top of work and an infant, it’s been a bit of struggle for me to stay present at times. I realized this last night while watching the Top Chef season finale.

Despite being perhaps Sophia and my favorite TV show, I felt like I never fully got into it the entire season despite being a great season. I thought about it and realized that I spent most of the time watching the weekly episodes while also on my phone or laptop distracted.

With Colin, the time that Sophia and I have to just sit on the couch and hang out is severely limited. If we’re lucky, we get maybe one hour of leisure time an evening to just unwind. Unfortunately for me, I’ve been spending that time mostly just multitasking whether it’s preparing for the next day, checking emails, or simply just catching up on text messages.

It’s a bad habit and likely contributing to my exhaustion. I need to be cognizant and do my best to stay present. Like my work time, my leisure and unwinding time needs to be protected as well.

Social media

I’ve done a pretty good job getting off social media lately. It’s been refreshing to try to focus on the present and the people around me, especially Colin.

I still have an Instagram which I check maybe once or twice a day to kill some time. And I have a Twitter account which I rarely use nowadays. Contrast this to a couple years ago and I was constantly doom scrolling Twitter during my downtimes, and I’m pleased with where I’m at nowadays.

For me, it’s just helped me become a bit more present and keeps me more focused. The constant context switching between work to get a 5 minute scroll in is quietly tiring on my brain. I’m much more productive nowadays.

Managing my anxiety

Sophia and I have a wedding in July in Seattle to attend for my good friend. Unfortunately it’s been giving me a ton of anxiety lately. I’m normally a very good planner and start booking things well in advance.

This time, I decided to procrastinate the booking of this trip due to the anxiety of the trip. With Colin, the logistics of the trip is incredibly difficult to manage. We had initially planned to fly to San Francisco and have my parents watch Colin for the weekend while we flew up to Seattle. That plan went out the door as my parents will be out of the country.

As such, we’ve had to pivot and decided to fly to Seattle with Colin. We have to rent a car to drive north a couple hours, and then take a ferry to the islands. We now have to find a nanny on the small island for the evening or Sophia is going to have to stay behind. Then we have to coordinate a ferry back, drive 2 hours to the airport, and then fly back to San Francisco.

This trip would normally be a ton of fun, but with a 8 month year old, it becomes anxiety inducing and it’s been really hard on me. Hence me procrastinating the booking of everything until last night. Of course, last night Delta was having IT issues and I spent over 2 hours trying to get everything booked.

Needless to say, I was stressed last night going to bed and that’s carried over today. My meditation this morning was a good one in that it helped me realize that my mind is in a self-induced spiral due to this trip.

Instead of focusing on the fact that I can take Colin to Seattle where I used to live on an awesome trip and see some of my closest friends, I’ve been thinking about stressful and tiring the trip will be. Yes the travel part will be somewhat stressful, but in reality, it won’t be the end of the world. We’ve flown long distances with him and been fine. He’s been a trooper.

I really need to do a better job changing my mindset around when it comes to these things. I think this all stems from the stress of the move last month that really put me in a hole. Yes travel can be stressful, but most of that stress is caused by my own mind.

We have an incredibly trip planned to fly to Seattle at a gorgeous time of the year. We’re staying with some of our closest friends for a couple nights who also have a kid. Then we get to take an awesome ferry to Lopez Island where I will get to see more of our close friends. Long travel day aside, we’ll be back at my parents house in San Francisco where Colin was born and get to relax that week seeing more close friends and family.

That feels a lot more exciting now.

A lose-lose situation

I absolutely hate the crazy shit happening in this country right now. Seeing large scale protests in San Francisco where I grew up and Los Angeles is disheartening. While most are peacefully protesting, seeing the bad apples take advantage to loot and cause destruction is frustrating.

I am pro-immigration. I believe that the country is built on immigrants and we should create a path to make access to the U.S. easier for those hard working people who want to come here and build a better life. At the same time, I do understand the need to tighten our borders and we cannot have a free for all type situation.

However what is happening now is just causing more divide. Trump’s policy to deport seemingly everyone is just not a realistic goal. We need to find a path for the good undocumented immigrants to become citizens, not try to deport everyone. It’s a losing battle all around and causing a bigger rift in this country.

At the same time, violent protesting also needs to be stopped. Destroying and vandalism homes, businesses, and property does nothing but further fuel the racism and justify more violence. Both sides keep throwing fuel into the fire. It’s brutal to watch as a native Californian and I hope that things get resolved as soon as possible and we can get back to making progress in this country.

Monday zest

It’s a rainy Monday here in New York and I’m in the office by myself. The entire coworking space is nearly empty and people seem to have decided to stay home today given the light rain. There’s no rain on my parade though as I’m feeling great.

After an exhausting but nice weekend trip to Baltimore, we’re back home and I finally got a great night of sleep. There’s just nothing like sleeping on your own mattress and being home especially after a lot of travel. After being gone for 2 weekends, I just want to be home for a few weeks to relax and enjoy the city. I’m finally getting some downtime.

I got up early and got a quick workout in the morning. I was at my desk a little after 9 and hope to have a full day of grinding to get my week started off right. My Mondays have been a lot better lately. I used to struggle mightily to get going on Mondays and I feel like I’m finally over the hump.

I believe part of that was just being exhausted from the weekends and overdoing things socially in the past. Perhaps another part of it is that my weekends are perhaps a bit more fulfilling now with Colin around.

Whatever it is, it’s been nice starting out my week energized again. Having the energy to go workout in the mornings is something completely new in the last month or so. I can only imagine how great I’ll feel once I start actually getting more rest on the weekends as well. Baby steps.

Baltimore

We’re off today to drive to Baltimore to see my in-laws. It’s exciting for Sophia and Colin that we now live on the East Coast and we’re able to make the drive down for a weekend trip. I know my mother-in-law is especially excited to see Colin.

Given the distance, they’ve unfortunately only been able to see him over the holidays when he was just 2 months old. It’s going to be a fun weekend for them to hang out with Colin and spend time with him.

For Sophia and I, it is also a great opportunity to get a bit of a break. We have dinner plans tonight and it’ll be nice to get out just us 2.

I suspect that we’ll be making a lot more of these trips to Baltimore for weekends or long weekends. Part of moving back to New York was to be closer to Sophia’s aging parents.

My bubble

Chime has always been an interesting company for me and presumably most of my peers. The company primarily targets Americans that are historically unbanked and/or lower income. Chime caters to these users with no overdraft fees and paycheck advances.

For myself, I’ve had a bank account with Chase (then Washington Mutual) since I was probably 12 years old. I am not a target customer of Chime so perhaps I haven’t fully bought into the company as much.

Undoubtedly, investing in companies in which I’m either a user or a target user is much easier for me to understand. Of course, in order to understand how the world works and become a better investor, I need to ensure to broaden my horizons outside my immediate bubble. I consciously try to do this, but I can be much better at it.

Congrats to Chime

I’m always excited for any tech IPO, but I’m especially giddy at seeing Chime hitting the public markets. I have a soft spot for fellow FinTech companies and it’s good to see a major IPO for us in the industry.

Chime’s journey to the public markets wasn’t easy. There were a lot of rumors that the company would go public in 2021 or 2022 given the large valuation at $25B.

Like many other companies, they will be going public at a much lower valuation with a $11B rumor. That is still a big win for most investors and more importantly for the employees who helped build the company.

So far the rumors seem to be trending positively for the company and I’m excited to see them debut next week.

A new era

We’ve officially moved into our new office off Broadway in the FiDi district in New York. Every morning I walk right past the tourist taking a picture with the Wall Street bull. I suppose it’s supposed to give me a bit of energy to start off my day.

For myself, I’m just happy to have a new comfortable office space we can call home. My commute got shorter by about 15 minutes which is nice, but more importantly, we have a bit more space to breathe in our new location. We actually have space to take calls now which is a major stress remover from my workday.

It feels good to be in middle of action in New York again. The energy levels are up again and I’m excited to get back into the office. Having colleagues to chat and grind with in-person is a whole new ball game. Running a small company fully remote is just not the way to go about things.

Although the FiDi the most fun area in New York, I’m excited to explore it and everything it has to offer. Coincidentally, the new Golden Mall food court is opening a few doors down in the months ahead. Perhaps they heard that I was coming.

Another great trip in the books

I’m back after a fun but exhausting golf weekend with the friends. It was really nice to get away, but after arriving, it was clear that things are different nowadays. I was basically running on fumes the entire weekend and instead of wanting to hang with friends, I kept thinking of good excuses to call it an early night and just sleep.

This is unfortunately the new normal at age 35 with a kid. Sleep is a premium nowadays. A golf trip with friends where we’re up at 5:00am to make an early tee time just isn’t as appealing as it used to be, even despite being in bed at a modest 10pm. Times have changed. I still had a great time and I’m glad I went as there’s probably not that many of these trips in the books going forward. But I suppose the next trip will need to have a lot more sleep built in.

We did 3 golf rounds at Coyote Springs, Sand Hallow, and Conestoga in the Mesquite, NV area. It is a popular golf destination and the courses did not not disappoint. The views on many of the holes up in the rock cliffs were epic.

My golf game was in shambles on Friday during my first round. I had not had time to practice my swing and things went awry starting last week. I was able to hack together a 90 on Saturday though with some modifications. And then on Sunday, my swing felt good and normal again. I had a great 44 on a hard front 9 at Conestoga. I lost steam on 10 and never recovered though resulting in a tough back 9 score.

This next month and half will be about relaxing, spending time with Colin, and focusing on work. We have a busy month ahead with closing out the quarter and I’m excited to get back to it. Getting back to a routine with our new office is going to be awesome.

Peaks and valleys

One of the harder mental parts of my job (and almost any startup) is that there’s a lot of peaks and valleys.

One week I can feel like everything is working well for me. I’m productive, I’m getting stuff done, and I’m recording a lot of wins. The next week everything can flip quickly. I feel overwhelmed and exhausted, and I take a lot of losses. In these “valley” times, it feels like nothing is going our way.

May felt like one of those valley times. I dealt with a lot of stress during my move and then on the work front, it seemed like nothing is going our way.

I can only imagine that this is what a professional baseball player goes through. Everyone goes through hot streaks where they are absolutely raking as a batter, and then cold streaks where they can’t seem to get a hit to save their life.

This is life and also the job that I signed up for so I’m not complaining. But when we’re in these valleys, life is tough. The beauty behind all of this is that the peaks can be just around the corner though.