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.

First boys trip post Colin

I take off tomorrow for a golf trip with a few of my close friends. It’ll be my first non-work related trip since having Colin. I am excited and at the same time feeling a bit anxious about leaving Sophia for almost 3 full days with Colin. It is a ton of work and it’s going to be hard on her.

I do think it’s important for both of us to get out and do these trips occasionally though so I am grateful she’s giving me the opportunity. On top of leaving Colin behind for a big stretch, I’m also anxious about my work piling up right now and the end of the quarter just a month away.

We’re short staffed right now so I’m handling multiple work loads and it’s been tough especially with the move the last month or so. I’ll need to be deliberate with my time and hopefully get a ton of work done on my flight over to Vegas.

It’ll be a nice break especially after the move, but I know when I get back it’ll be go time and I’ll need to really focus on work for the month of June. It’ll be a lot to handle, but I do need a bit of a break from everything for a bit. Hopefully I’ll come back nice and refreshed for the grind ahead.

Unofficial summer

Summer is unofficially here with another MDW in the books. Back when I lived in New York 10 years ago, my friends and I probably would have spent the weekend partying in a beach town or on a trip somewhere. Times have obviously changed now. Both my family and my few remaining friends in the city seemingly all stayed local.

After Colin and I beat this stomach bug on Friday, we had a great and fulfilling weekend. On Saturday, we stayed local in Brooklyn and went to check out Industry City, then hung out with some old friends throughout Brooklyn. On Sunday, we went to the city to do a “Vieje day” which basically consists of eating.

I finally got the chance to go to Mam which was on my list of places to check-out for over a year now. We ended the day getting happy hour at Fish Cheeks which is one of my favorite restaurants in the world. Getting out and especially eating out with a kid is undoubtedly harder and much more tiring, but it was great to have a sense of our old lives a bit again.

On Monday, I had a morning tee time with an old friend from high school. It was great to get out again and was my first in New York. My swing is in shambles right now and I’m officially worried for my golf trip this upcoming weekend. I have no idea how I’m going to fix this, but I’m going to have to figure something out soon.

The past couple of weeks were about getting back to a routine and getting settled in. Things feel like they’ve turned a corner and I’m happy to report that I’m feeling great again after this long weekend. After everything going on, we needed a sense of normalcy again. I’m excited for this summer with Colin — it’s going to be a special time for him and us.

Slowing growth

Well it didn’t take too long for Colin to get sick at daycare as he caught a stomach bug in his 2nd week. It’s been a less than ideal experience the last few days and he’s home with us today which is causing a tough disruption in both Sophia and my work days, and plans for time to ourselves this afternoon.

That is the unfortunate life of being a parent though and I suppose I need to get used to it. I’m someone who likes being organized and I try to manage my schedule meticulously. With a kid now, life is just a lot more unpredictable and I’ll need to roll with the punches more. It’ll be a nice change of pace for me to be a little more spontaneous in life.

On another note - I’m unfortunately still meeting with a lot of companies that seem to be struggling post-ZIRP years. On one hand, I am surprised that there have not been more companies with down rounds. It seems like a lot of companies were able to manage cash well and get to or close to profitability.

On the other hand, a lot of companies are struggling to continue to grow into their valuations they received in 2021. Growth rate have slowed and the prospects of an IPO are dimming for a lot of thee companies. With the rise of the next wave of companies, there is an interesting situation where these companies may miss their window.

Unfortunately that may mean not so great M&A opportunities. Of course, the hope is these companies will be able to reaccelerate growth and get to the IPO. Also, the IPO market could also improve in their favor.

Weee!

I was introduced to Weee! by my coworkers yesterday and I am hooked. I expressed that I don’t really have time to get to an Asian grocery store nowadays especially because there are none close by in Brooklyn, and both my colleagues told me to just use Weee!

I had heard of the company before, but as a company that specializes in Asian groceries, I just figured that things would be marked up like crazy. Plus I generally enjoy going to grocery stores and adjacent places like Costco. For those two reasons, I have generally stayed away from ordering groceries online through Instacart or Whole Foods.

Of course moving to New York has seemingly zapped the enjoyment out of an afternoon at Costco and at the grocery store. On top of that, I was shocked to see that the prices on Weee! were actually cheaper than most storefronts like H-Mart.

Given the growing Asian population in the U.S., a service like Weee! makes a ton of sense. They focus on specific cities and delivery next day in New York. I save money and time by shopping at Weee!

I have yet to see the quality of the produce, but my colleagues report that it’s high quality stuff. Given my lack of time with a baby right now, I suppose I’ll be happy to avoid a 2 hour weekly trip on the weekends to the grocery store and spend that time elsewhere.

Being deliberate with my time

One of the biggest changes for me since having a kid is that I have to be much more deliberate with my time. Even with childcare/daycare, having a kid means an extra 1-5 hours a day from one or both parents. Of course we want to be involved parents and spend as much time with Colin as possible, so I hope that Colin gets at least 4-5 hours of time with us as well.

Since Sophia and I both work, we’ve had to split the drop-off and pick-up times of daycare and that has worked well for us for now.

I go into the city early on Mondays and Wednesdays and go to the gym before work while Sophia drops off Colin. Then I leave work early at 4:15 to pick up Colin and spend time with him in the evening.

On Tuesdays and Thursdays, I spend more time with Colin in the morning and drop him off at daycare prior to commuting into the city. And then I have more time late afternoon to work or go get a workout in.

It’s definitely been a challenge as my days have shrunk now with a kid and I’m still getting used to things. I have to be much more deliberate with my time nowadays. That means less time wasted sitting around scrolling on my phone. That time could be spent working or hanging out with Colin.

I’ve had to find ways to be much more efficient at work as well. Of course AI helps to a certain degree here, but I’ve been also looking for ways to cut out the bottom 20% of my work that adds little to no value to advancing the company.

It’s been a good exercise in finding out what’s truly important and what is not. It makes me and the company much more efficient.

IPOs are back? (hopefully, maybe)

Sophia and I had our first night out in New York as we went to grab dinner with friends in the city. It was an awesome night and yet another reminder that we need to go out and live life a bit more.

On the market front - IPOs are back, at least for now, as Hinge Health is looking to go public in the next week or two. It seems that the bankers priced things relatively low, and there are more orders than supply.

I know we’re not the only ones watching Hinge Health and I can probably speak for most of the startup world in that we really need this one to go well. So far most IPOs in 2024 and 2025 have gone fairly well but whether that opens the market given the uncertainty is yet to be seen. Fingers crossed.

Back to enjoying life a bit more

It’s been an interesting week and half back in New York. Most of the time has unfortunately been spent trying to get our apartment in order. I am someone who likes to get shit done and it’s hard for me to leave unpacked boxes or things out of order.

As such, I spent most of my Friday evening putting up a shelving unit so we had some places to hang our pots and pans. Then I spent most of our time Saturday shopping for things for the apartment. Combined that with raising a 6 month year old and I unfortunately have had little to no time to enjoy the city much or see friends.

I did realize yesterday that most of this is my fault. I could probably use a chill pill or two in regards to the apartment. I also probably have my priorities completely wrong right now. Instead of enjoying my time off to go enjoy New York and see friends, I’ve beating myself up trying to knock out my checklist of shit to do.

I suspect that this started over a month ago as we started to plan for our move. I’ve been so focused on the move that I started to live my life off my to-do list. That’s no way to live life and it’s time to change that mentality. I live in NYC after all and there’s too much fun shit to do to spend my entire weekend running errands.

Feature Request

We currently use DocuSign for our eSignature uses and I often send 1-2 things per day to clients to sign. The process historically is to log-in to DocuSign, find the template, put in the info and send it to the client. Then send an email to the client letting them know it’s in their inbox.

Why are these eSignature services not built into any email clients for automation? It seems like an easy win that saves people a lot of time and annoyances. I’d love to open Superhuman, and then have a DocuSign integration that allows me to send a doc directly from my email client. AI could be used to populate the fields as well.

I’m not sure why this hasn’t been built by DocuSign or any other eSignature company at this point, but it feels like a no-brainer to me and I would switch providers to the ones that have this built in.

Stability please

After 3 nights of good sleep, I’m finally starting to feel normal again. My motivation and happiness is back, and I no longer feel like a brain dead zombie. That was a rough couple of weeks for me and needless to say I’m glad that’s over.

In other things I’m glad is over, it appears that the market has rebounded to a positive year after Trump’s self-inflicted trade war began. Our President seems to have folded on his bold plans and the market has adjusted.

Of course, we’re not in the clear yet and who knows what Trump will do next. But it seems like Trump has shifted his focus from destroying the economy to meeting other countries in the Middle East and getting deals done. At least this gives us a bit of a breather on the market side for a bit and we can get back to growing the economy.

For now, some stability is exactly what I need in my work and personal life and for the first time in awhile, I feel like I’m getting a bit of it. Life is good.

SF vs NY

It’s pretty funny just how many Californians and specifically people from the Bay Area are here in New York. I walk around my neighborhood in Brooklyn and I never have to go far to see a SF Giants hat or a Warriors T-shirt. Apparently a bunch of folks who have moved into my building are from San Francisco.

I have no actual data on this but I’d guess that there’s many more folks moving from SF to NY at this point than the other way around. At this point, NY is fully back. Things are looking even better than it was when I left in 2018. New buildings and restaurants are opening everywhere still. It feels like it’s even more lively than it was when I left.

San Francisco is just on it’s way of making it’s way back. I really love what the new Mayor is doing there working with businesses to come back and rebuild the city. But at this point, it’s a far cry from where New York is and likely going to be at least a few years until we start to see SF get back close to where it was pre-pandemic.

The energy in SF just has been dead the last few years with no one going into the office anymore. The FiDi and downtown area feels at best 25% of where it once was. It doesn’t feel like a ton of construction is happening and restaurants seem to be closing more than they are opening.

Of course, San Francisco will never be New York for better or worse. The beauty about San Francisco is that it is much more chill and relaxed than New York. But at this point, if I was in my 20s working my first job out of school, I would much rather be in New York than San Francisco.

I am excited for how the city changes in the next few years while we’re in New York though.

A new chapter

While we got to New York on Monday, it’s actually starting to feel real today. We dropped Colin off at his daycare for his first day. He went in smiling and was ready to be a big boy. The daycare uses Brightwheel to send us updates on Colin, and I’m loving the experience so far. As much as I love spending time with him, it is nice for Sophia and I to have some time and help with childcare.

I also commuted into the city for my first day in the office. When I lived in New York during the pandemic for a couple of months, I signed us up for Rise in the Flat Iron. Now that the space is closing this summer, we’ll be moving to the FiDi at some point this week or next. It’s yet another move to handle, but this time around I’ll have a lot more hands and we’ll definitely be hiring help to do everything for us.

It does feel like a new chapter began today. Things will definitely get a lot more difficult at times managing commutes and strict daycare drop-off/pickup times. But things will definitely be a lot more fun and exciting living in New York again.

We made it

We all made it to New York and the movers are coming with our stuff in about an hour. The nightmare of a cross country move with a 6 month year old is nearly over and I couldn’t be more excited to get back to a normal schedule.

Monday/Tuesday were brutal days as expected. Sophia and I worked hard to pack up our apartment on Monday, and then took a redeye to New York. Colin was a champion and had very little fussiness. Naturally, he slept the most out of all of us. We landed at about 2:30am PST and got Colin on schedule while Sophia and I slugged through the rest of the day.

I’m stoked about being here, but it didn’t take long to get a reintroduction to New York as we had to make a Costco run yesterday. That was probably the last time I’ll ever go to Costco in Brooklyn.

I’m hoping after today, we’ll feel a lot more settled and be able to actually enjoy being here. I cannot wait to sit on my couch and watch TV tonight. My back could use some support after a week and a half of sitting on the floor.

Countdown to New York

Another day and another moving annoyances. My car pick-up has been pushed back again and my schedule is now in-flux. The stress and exhaustion of the last few weeks is weighing on me.

I cannot wait until this time next week when we have everything and we’ll hopefully get back to a normal schedule. On my next cross country move, I’ll likely look to pay more of a premium for folks to take a lot of this stress of my hands.

Luckily work hasn’t been too crazy and I’ve been able to move the ball forward despite having a crazy schedule this week. I’m thankful for having a great team at work that’s been able to cover for a lot of my stuff this week.

I’ll need to make sure to use this weekend to get some R&R before a big travel day on Monday. On the other side of that travel day is hopefully a lot of fun and some time off to enjoy the city with Sophia and Colin.

Fire fast

One thing I’ve learned in my startup career is to always fire fast and hire slow. It’s the cliche statement that any experienced operator will tell you, but unfortunately most people need to live through a tough situation before they actually take action on it.

It’s simply just hard to fire people as there’s a human aspect to all this. We learned the hard way early on at Secfi with probably a couple individuals that needed to be let go months after the hire when we realized it wasn’t working out. As per the script, we let it go many months too long and it caused a lot more issues than it needed to.

Of course, the lessons from work could also be applied in real life. We hired a temporary nanny for two months in San Francisco as Sophia went back to work. We knew it was temporary as we were moving to New York and was upfront about it. We hired fast as it was just temporary and the first person we met seemed to be okay and had a good referral from the last family.

After the first week, it was evident she was not great. She complained a lot, made a lot of excuses, and did not seem to be on a good rhythm with Colin. We probably should have made the switch early on, but since it was temporary, we decided to tough it out.

She took good enough care of Colin that it wasn’t an urgent need to let her go. But she couldn’t stick to our schedule and make excuses for why she couldn’t. We now regret that decision and should have made the change early on.

Of course, with her last day tomorrow, she called in sick this morning. It seemed like the perfect day to call in sick as it was a payday and she had only 2 days with us remaining. While I wanted to believe it was innocent, we also noticed that she took her stuff with her yesterday when she left so this was clearly planned.

At minimum, we now know for future needs. But sometimes we have to learn the hard way.

Things don't always go to plan, and that's okay

Well the movers came and did a pretty good job getting everything out and on the way to New York. The service was right for the pricing but I wasn’t pleased with the carelessness of the way they handled things including causing a good amount of smudges on our hardwood floor. But you get what you pay for.

I wish I was sitting here feeling amazing about everything, but sometimes your plans just don’t pan out exactly the way you want it to. I had scheduled movers for yesterday with the hopes that everything would arrive on Tuesday or Wednesday next week leaving us with our stuff and a week off. Unfortunately they let us know that the stuff wouldn’t start the journey to New York until Friday and the earliest we’d get it is Saturday.

On top of that, the car pickup I scheduled for today got pushed back to Friday so again we’ll likely not have a car until the back half of next week. On top of that, our mattress has yet to ship so we may not have it ready for Tuesday.

So all my plans to basically have my stuff as soon as possible in New York while we’re out of office and getting settled has completely gone out the window. And the icing on the cake is that we may not have a mattress to sleep on when we arrive.

As a type-A planner, the stressful week has gotten even more stressful and my anxiety is through the roof right now. But thus is life and we’ll need to adjust as needed. I suppose in life part of having a good plan is making sure that your contingency plans are also good.

Luckily, Sophia and I are in a good position with friends in New York. In a worst case, we can always go to a nearby hotel that shouldn’t be too bad. As for our stuff, I had hoped we could casually unpack throughout the week, but we’ll just need to take some time over the weekend to do the big things and then just live with some boxes for the near-term. It’ll all work out, but it’s annoying nonetheless when things don’t go to plan.

Time to downsize

The movers are here and doing a great job getting all our shit out to New York. I’m happy to get everything out and start the process finally after weeks of packing. Unfortunately we’re about 50% more than our estimate of stuff.

As someone who likes to live as minimalist as possible with material goods, I have no idea how we accumulated so much stuff over the years. A big part of that is the kid, but I can’t deny that we have a ton of clothing and other goods that is probably excessive.

It’s probably time to try to downsize and get rid of as many things as possible while we’re in New York. The good news is that we’ll likely be forced to as our living situation is much smaller than it is in San Francisco.

It’s a done deal now, but we’ll probably have yet another garbage and donation run while we’re out in New York.

The return of San Francisco

I had an amazing and full weekend with friends and family. On Friday we hung out with my sister and family for a few hours before seeing friends for dinner. On Saturday we had our going away party and was able to see over 20 of our closest friends here in SF. And on Sunday we had a nice picnic on Angel Island to celebrate my good friend’s wedding.

It’s these moments that I’ll definitely miss while we’re back on the East Coast for a few years. There’s definitely a lot of FOMO right now especially as San Francisco is making a huge comeback.

I received a note this morning from one of the local city groups that I follow and there’s a ton of positive developments. Crime fell to it’s lowest point in 23 years and car break-ins dropped by 54%. Our newly elected Mayor has been doing a ton of great work in the city convincing cities to reinvest in San Francisco.

The road back from the lows of the pandemic have been especially hard for San Francisco, but I haven’t been this optimistic for the city in a long-time. I predict that when I finally do get back home, San Francisco is going to feel much like the bustling times of the 2010s rather than what we’ve seen from the first half of the 2020s.

Grateful

We’re just about 80% done with packing on our end. My allergies are gone and I actually feel rested and energized. I got a ton of work done over this week to set myself up to be largely OOO for the next two weeks. And it’s Friday going into a fun weekend of activities. Life is good and I am in a very grateful mood.

I am sad to be leaving San Francisco. We’ve been doing a lot during the move like getting rid of my plants that I got during the pandemic and finally throwing away some leftover stuff from our wedding. When one chapter ends, there’s always going to be some sadness.

Today, I’ve been really grateful for the last 7 years back home in San Francisco. Sophia and I came here and lived together for the first time. Got married here in SF and had our first child here. It feels just like yesterday when we went to our first Bay to Breakers a week after Sophia officially moved here.

I’m incredibly grateful for all our friends here and the experiences we were able to share with them. Being able to come home and watch my little sister grow into a teenager has also been special and I’m so happy to have been part of her life. It’s been a blessing being back home for the last 7 years.