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.

Much needed work breaks

I needed to get my mind a bit right again yesterday so I took a break in the afternoon to go to the gym and unleash some steam. It was a really nice moment for me to unwind for an hour after a stressful morning. It’s really easy to spiral when your mind is not in the right headspace and that’s not productive for my health nor my work product.

Taking a break to work out always gets me in a much better mindset. Sometimes I just need to step away from the screen for a bit and burn off some steam whether that’s through meditation, a walk, or working out. I had been doing this since even the early days of my career working 70+ hour weeks.

My coworkers thought I was crazy going to take a break at 5pm to come back to the office at 6:30. Afterall, that’s an extra hour and half of work that could be done and some extra sleep. But I always found that I was almost always more productive after I got back. That project that would have taken me an hour could take me 20 minutes. Or that problem I was stuck on was suddenly not a problem anymore.

Yesterday, when I got back to the office, it was business as usual and I felt reinvigorated and ready to grind again. Things are trending on the up and up heading into the weekend. I just need to have all my brain cells in-tact to take advantage of the opportunities.

Mental strength

These next few weeks and months are going to require a lot of mental strength to get through. The trade war news and market volatility is admittedly taking a toll on me right now. This isn’t a fun time for anyone in finance right now. CEOs and companies are taking a lot of action and changing 2025 plans. IPOs are likely to be on pause for now.

I don’t have any control of the markets, but the markets always have an impact on us given the nature of our business. It’s a stressful time and everyone I talk to in the industry feels the same way.

I know what I need to do in the next few weeks/months. And that’s to dig in, keep my head down, and work hard. Positivity is going to go a long way for me and staying out of the negative news cycles is step one. Of course that’s a lot easier said than done as I want to scream into a pillow right now.

At this point, I’m trying to remind myself that everything will be fine and this is a long journey of a lot of ups and downs. Hopefully I’ll be able to look back at this period and be glad that I went through it. And also hopefully there’ll be a lot more ups than downs in the future.

Saving for a rainy

The rain is back today in San Francisco. We’ve had what feels like a rainier winter than normal and it looks to continue the rest of the week. I suppose the rain is a good excuse to stay in, spend time with Colin, and rest.

Metaphorically it continues to be a rainy winter in the markets. Trump’s trade war has everyone spooked right now and smart people I talk to are saying that we’re either already in a recession or we need to let it play out because it’s all part of the plan. I have no idea how long this will last or the outcome.

I wouldn’t say I’m a fiscally conservative person in the grand scheme of things. But now with a young child to support, my mentality is now to save for that rainy day. I’m going to continue to live my life, but I’m taking more action nowadays when it comes to things like budgeting.

For example, my budget for housing in New York is going to be much more strict. We’re likely going to be adjusting our budget downwards and trying to aim for the lower end of that budget rather.

We’re in a fortunate position that we do not need to panic about finances right now as we’ve done a good job saving. But I don’t ever want to not be in this position in the future. It’s best to be conservative and safe here, than be worried down the road if things do really turn south.

Colin's first day with a nanny

Today was Colin’s first day with the nanny as Sophia heads back to work. We feel like we made a great hire in our nanny and Colin seems to really like her. However, there was quite a bit of anxiety for us between yesterday and today.

Deep down, we know Colin will be fine and this is a normal thing parents go through. Colin will need to have a nanny and eventually grow into daycare and then school. It’s part of life and growing up. But it is hard officially losing control of his day to day. We’re just reminding ourselves that this is for the better and will be part of growing up.

I am excited for Sophia to go back to work again. She needs some time away from Colin for her own sake and I think she’ll start to enjoy parts of work again shortly.

Healthier habits

I had a rough weekend unfortunately. The sleep deprivation and stress with work and life really just caught up with me. I was exhausted coming back from Hawaii last Monday and went straight into a mountain of work. There was a lot of late nights and early mornings and I never felt good most of last week.

I did my best to try to catch-up on sleep and life over the weekend but my other full time job of being a Dad can’t really be put on pause. We didn’t do much over the weekend and it was unfortunately mostly spent just tiredly hanging out with Colin. There was a lot of low motivation and slugging around.

I’m finally feeling decent again this Monday morning, but it’s going to be a journey these next few weeks to close out and quarter and I need to make sure to take care of myself. That starts with getting back to healthier habits like reading before bed and moving my bed time earlier.

Over the last few weeks, I could tell that Sophia and I started doing more and more with life as we got more comfortable with Colin and he started getting on a good schedule. That meant more going out with friends, staying up later than the early days, watching more TV, etc.

All that stuff is fine of course, but it adds to our exhaustion levels. It’s time that we peel some of that back a bit. Like with most of things, it’s the simple things in life.

Keeping my head down

I’m glad it’s Friday. I had a pretty good birthday yesterday. Unfortunately I was just slammed at work and running on fumes most of the day. Sophia and I were able to go out to a nice dinner at Ernest while one of my friends watched Colin. I was really grateful for the opportunity to go out to dinner again, but I was half asleep pretty much the entire night.

The transition to crazy work schedule with a newborn hasn’t been easy. The work stays the same and I have less hours to get it done. My days are longer now to accommodate the schedule, but there’s still less hours than I had to focus on work. It’ll continue to be a challenge and I really need to make sure to use my weekends to rest and spend time with Colin as much as possible nowadays.

On another note, everything just feels crazy right now. Trump and his administration are following through on their tariff strategy which is causing a lot of uncertainty in the markets. There’ll be a lot of short term pain unfortunately. One of which is a possible delay in the IPO window. That is frustrating to say the least for all of us in the startup world.

The uncertainty is causing a lot of confusion and volatility. No one really knows how this will all end. I’m vowing to try to stay away from reading every news headline out there right now. It’s not good for my mental health. I need to keep my head down and stay focused on the goals and what we can control.