Getting back in-office

It’s holiday party season and it’s at this point that I’m really missing having a full office of colleagues. We’ve been doing more bonding activities as a company recently which has been nice, but it’s not the same.

Work is simply just not the same when you are more or less fully remote. I have our clients and partners in San Francisco still, so that allows me some human interaction from time to time.

But I simply just miss the water cooler chats and commiserating with my team at times. When it comes to being remote, the fun times aren’t as fun and the shitty times are shittier.

With a potential move to our New York office on the horizon, I’m excited to finally get back in office with the team. We’re growing our office out there again and on my list is getting a more permanent space in the city. I’ll be sad to leave my home in San Francisco, but work is going to be a lot more fun and productive.

Growing up in the 90s

Some of my favorite social media accounts is the 90s retro ones. Throwback videos, pictures, and memes to the 90s. I was born in 1990 and it was a really fun time to grow up.

Video games were really starting to take off. The era of music with rap and pop rock was great. And the internet was fun and new for all of us.

Things were a lot simpler back then. One big obvious reason was well.. because I was a kid. But it was also an era where things just seemed a lot slower.

While almost everyone had a TV, it wasn’t a time when looking at a screen all day was normal. You had to call friends during certain time frames. There was no text messaging. Emails were more similar to sending a letter via snail mail rather than instant responses. Probably most importantly, social media didn’t exist and demand our attention all day.

Of course, this ignores all the positives as well but the point I’m trying to make is that it just felt like kids connected more with each other back in that era. And there was a lot more spontaneity and adventure in the real world.

Obviously, I can’t put Colin in a time machine so he can grow up in the 90s. But I am hopeful that I can instill some of the positive experiences from my childhood and bring that to today’s world for him. I think a lot of that starts first with being more present and not glued to our phones. It’s something I’m working on.

Babies will be babies

Colin decided to do newborn things last night and decided he was hungry for an entire extra meal in the middle of the night. I suppose I shouldn’t be too surprised because I’ve been known to eat a ton of food and he is my son. Nevertheless, it was frustrating as my planned 5 hours of uninterrupted sleep got cut down significantly with an unexpected wake-up at 4am.

I spent much of this morning in disarray and googling how to fix my baby’s feeding schedule. Unfortunately, it turns out that babies are babies and some like to eat more than others. That is to say that there is likely no silver bullet here and I’ll just need to suck it up until he ages a bit.

All this made me realize that Sophia and I have spent too much of the last week or so obsessing too much over his schedule. We’ve been fortunate that Colin has stuck to some semblance of a schedule for the last few weeks. Through this, we’ve had some really good days and nights.

However, whenever things don’t go according to plan or the schedule gets disrupted a bit, Sophia and I have started to stress about it. This isn’t healthy for us and it’s not setting proper expectations for our son. Babies are unpredictable in nature and there’s a wide range of differences depending on the baby.

Going forward, I’ve realized that we need to go with the flow a bit more. It’s okay to get a bit off schedule at times when we want to be out and about. It’s okay if Colin misses his bed time by a little bit. And when he does decide to wake up randomly in the middle of the night because he’s hungry, we just need to suck it up as it won’t be the last time it happens. We’ll be happier once we do.

Trump and Elon

I didn’t vote for Trump and I don’t like the guy. I think he’s self motivated and doesn’t really care for anyone but himself. I don’t think he’s good for the country or the world for that matter. All that said, I would want nothing more than to be completely wrong. I hope that I can write in 4 years after his presidency is over and say that he did a damn good job and I was wrong.

At the end, I am still optimistic for the future of America. While I can’t say I agree with a lot of his cabinet picks right now, I also can say that I am hopeful in a lot of these moves.

Elon has clearly been a controversial figure and my feelings on him are mixed, but he is the greatest entrepreneur of our generation. Perhaps he can inject some new life into our government which is much needed.

Perhaps we are a bit stuck with classic political figures in cabinet positions and it’s time for a bit of a change. Maybe that change is what’s needed for the country to move forward.

Maybe it’s all blind optimism right now. Maybe he fails miserably and the next 4 years are more painful the last 4. I have no idea how this will all end, but I hope it all works out. It’s all I can do.

Bitcoin crosses $100,000

What a trajectory in just over 11 years.

Bitcoin hit $100 on March 31, 2013
Bitcoin hit $1,000 on November 28, 2013
Bitcoin hit $10,000 on November 29, 2017
Bitcoin hit $100,000 on December 4, 2024

I first heard of Bitcoin when my friend Francis was talking about a digital currency. On March 2014, he sent me 0.015 Bitcoin.

That 0.015 Bitcoin he sent me on my 24th birthday was worth $9.15 at the time. By the time he followed up in 2017 it was worth about $150. Yesterday, it was worth about $1,500.

Like everyone else, I followed the crypto boom in 2017. I didn’t participate then. But when the bubble burst in 2018, I thought this was a good time to buy in. I’ve been a holder ever since although I’ve trimmed and diversified my position significantly to make sure my personal balance sheet is somewhat in line.

Admittedly, taking profits on crypto was hard to do as we’ve never seen anything like it in our life and I do believe in the long-term upside. But overconcentration is overconcentration.

I still remain long on a sizable portion of Bitcoin and Ethereum. I’ll be curious to see where things go from here as the technology evolves and adoption picks up.

Focusing my attention

With a newborn, a short staffed team, and the holidays around the corner, I’m very focused on prioritization right now. The reality is that I won’t be able to take on as much as I’d given everything happening right now.

This has always been the case with just being a startup in general. You just simply cannot do everything and have to pick and choose your priorities. However, it’s definitely a bit harder for us right now with key members of our team out on leave. There’s only so many hours in the day.

For my team, that’s really focusing on a certain subset of companies right now. We’d love to take a look at a lot more companies that are building interesting products but our limited time means that our bar is higher. There’s too many great companies out there and I’d rather focus on our handful of opportunities than spread ourselves too thin.

The calm before the storm?

I’m back in the office for the first time in a month. Getting out of the house and getting to the place where I’m most productive feel good.

So far this November and December in the private markets seems a bit… well dead. That has been mostly the same as it has been the rest of the second half of the year. After an initial pickup in Q2, things started to calm down in Q3 and has not yet picked up in Q4.

We had thought there could be a small surge due to noise around IPOs in 2025 after the election, but that has yet to really happen yet. It looks like December will close on a relatively calm note.

Once again, we’re sitting here waiting for the markets to pick up. Let’s all hope that this is the calm before the storm in Q1 in 2025.

ServiceTitan IPO thoughts

I’m “back” working again full time and it does feel good to be back on the grind. My plan is to really get after it for the next 3 weeks and close out the year strong. It’s going to be a challenge for myself with a newborn here, but one that I’m excited to take on. Life isn’t getting any easier so might as well rip the bandaid off and try to adjust to the new normal.

On the news front, the latest in the VC and private company space is ServiceTitan’s S1 disclosing the compounding ratchet. There’s a lot of interesting commentary out there and I don’t feel like writing too much about it at this point.

What I will say is that I would love to get the inside scoop on the negotiation of these funding rounds. Obviously there’s a reason why ServiceTitan agreed to let investors have a compounding ratchet here in their term sheet.

Was the company really strapped for cash that they needed to get something done? Were the executives against taking a further down round and instead had an optimistic view on the market? I’d guess there was a lot more to the story than what’s on the surface.

The strategy and reasoning here is what’s unfortunately missing in the discussions. Undoubtedly 2022 and 2023 was a rough time for startups. Many of them were being forced term sheets at high valuations and it was hard for them to say no. Then when the market crashed, their hands were forced.

There’s unfortunately a lot of negative sentiment right now given the talks, but even with the dilution of additional shares, if it happens, it could still be a successful IPO. So I remain positive for my friends and investors at ServiceTitan.

Back to the grind

Just like that November is over and I’m officially “going back” to work tomorrow. I feel incredibly fortunate to work for a company that is supportive and encouraged me to take things easy. My team members were able to cover a lot of my work the last few weeks allowing me to spend more time with Colin and Sophia.

While I’m going back to a more full schedule tomorrow, I do feel like I never truly logged off. For better or worse, I worked a bit nearly every day from the day Sophia went into labor on the 5th all the way to today.

There are times where I do wish I could fully log off and just disappear for weeks/months at a time. That’s a big benefit to working at a large company. I have friends in big tech that can take full 4 months of paternity leave and never work a day. That does sound nice at times.

However, that’s just not possible at many small companies where you have a critical role in the day-to-day functions. That’s the case at Secfi. While my team allowed me to only work an hour a day at times, there were just some things that I couldn’t pass off.

All that said, there are great benefits as well as flexibility goes both ways. As the business slows down after Christmas and in January, I hope to take some more easy days to bond with Colin. I’m more than okay with this tradeoff and it fits me and my personality much better. I’m not even sure I can stay away from working for 4 months anyhow.

Looking at my schedule ahead, I’ve got 3 full weeks of work until the holidays really kick off. It’s going to be a bit of a challenge trying to adjust to the new normal with the child. I can’t do my normal in the office at 8am 4 days a week schedule anymore as I have to help Sophia with Colin and ensure she’s getting enough rest.

I’m fortunate to be able to work from home so I’ll likely look to spend 3 days at home and 2 days in the office in December just to start out. We’ll see how that goes for now and I’ll look to make adjustments as they come.

Thankful

I’m incredibly thankful for life right now. My life changed 3.5 weeks ago when my son was born and this November has been a blessing.

Nothing makes me happier than picking up my son and watching him stare back at me. Yes, this includes those 4am crying sessions. Every moment with him is a blessing.

Life is undoubtedly different. I no longer can go to bars for hours at a time to watch football with the guys. I can’t go play golf anytime I want. Sophia and I haven’t had a nice dinner out this month.

My life is a lot more boring in a lot of ways. At the same time, I’ve never felt more love and happiness in life. It’s a great trade off that I'm happy to make.

I’m thankful for everything right now in my life and feel incredibly blessed.

The growing to-do list

My to-do list has piled up over the last week between personal and work items. At this age, Colin allows a lot of downtime when he’s napping during the day. But Sophia and I have really taken the opportunity to take him on long walks and get him outside. It’s been awesome and it does feel nice getting out after being cooped up inside most of the first few weeks.

However, that means everything else on my checklist gets pushed down the priority list. I’m okay with that in theory. This month has been about bonding with Colin and helping Sophia. Those are priority 1 and 2.

At the same time, old habits are hard to break and I can’t help but feel unaccomplished and stressed about my growing checklist of everything else. This will continue to be a thing going forward and it’s something that I have to learn to live with.

I’ll need to either find more hours in the day or learn to mentally deal with it. The latter seems to be a bit easier at this point.

Embracing the moments

Like most new parents, I’ve been incredibly frustrated by my son’s 4am antics. His 3am feed goes without issue, but he generally just refuses to get back to bed at this hour. You’re tired and there’s seemingly nothing you can do to calm him down and help him go to sleep.

Last night, I decided to take a different approach. I decided that I was just going to embrace this time as a special time where my son and I can bond. I told myself that the reason he won’t go to sleep is because he wants to do nothing else but hang out with me at that moment.

I’m not sure if that’s actually true, but he was incredibly cute and cuddly this morning. Yes, I was tired and it would’ve been nice to sleep for 3 more hours. But the 3 hours we spent from 4am to 7am just cuddling and hanging out was special. Afterwards, I realized that I might miss these days even.

Learning to be on someone else's schedule

I’ve spent nearly my entire life as a “scheduler”. As a teenager, I had my notebooks with my schedule locked down. At the beginning of each school year, I’d plan things out and have a great planner so I stayed on top of everything.

As I got to college, that shifted to an Excel sheet where I planned my quarters/semesters ahead. It wasn’t perfect, but I knew what I needed to do weeks in advance and planned around it. That included my social calendar. Yes, it’s a bit embarrassing to write that but I’m a nerd at heart and I still have nightmares of missing a final or a class due to forgetting my schedule.

When I got to the workforce, my work calendar became my life calendar filled with both personal and work events. I meticulously plan my weeks every Sunday evening or Monday morning for the week ahead. This help my anxiety quite a bit and I have gotten even more anal about my calendar which includes making Sophia send me calendar invites.

My planning lifestyle has definitely helped in my first 3 weeks of fatherhood. But one area I’m struggling with is the fact that I’m no longer on my schedule. I can plan all I want, but my son dictates everything now.

Today, I had a great plan to get up early and take my son to get coffee prior to his 9am feeding. That went out the door when he decided not to sleep after 4am and didn’t go back to bed until after his 7am feeding.

I had a 1-3am block to grab lunch with Colin and go to the grocery store. I was going to be back by 3am to make his next feeding at home. Of course, that went out the door when he got fussy at the grocery store delaying everything and forcing us to feed him in a Walgreens parking lot.

Everything got shifted back and all of my sudden, my 4-6pm window to go to the gym was no longer. This all seems very minor of course and an excuse not to go to the gym in the rain can be a seen as a positive. But as a type A scheduler, this really threw me for a loop and stressed me out.

This is unfortunately my life now. I’m no longer scheduling for myself, but rather for my son. He takes priority. And his mom comes after that. I’m third in line at best in this equation. I suppose that’s what parenting is about - making sacrifices for your kids and putting them first.

It’s easy for me to say that I’d be happy to do it, but 3 weeks in and it’s proven harder than I thought. I know I’ll get used to it though and make the right adjustments. Soon enough, I’ll start having nightmares about missing my son’s events and not mine.

3rd weekend with Colin in the books

It’s our 3rd weekend home with Colin and we’re coming up on 3 weeks since his birth. Things seem to be moving incredibly fast right now. Everything is kind of blended into one.

We’re not doing a ton right now. We’re leaving the house for lunch or errands or a walk perhaps once a day. Colin sleeps for 2/3rds of the day. And spends half his waking time feeding. I am having a lot of fun bonding with him when he is awake. But there’s a ton of “downtime”.

I’m keeping myself busy by trying to get some stuff done at work here or there. It’s not ideal, but it also feels nice being productive. I was working out, but I got some tendonitis on my foot after pushing myself early last week so I’ve been on rest for the last 5 days.

Sophia and I have filled in time by mindlessly scrolling our phones and watching TV. It’s nice at some points, but it’s not my cup of tea for the long-term.

As Colin grows, we’ll be able to do more with him which I’m excited about. In the meantime, I’m just just trying to be present and enjoy the downtime while I have it.

Paternity leave (work?)

My paternity leave has been going… well as expected. I had hoped to have a lot more downtime and not work as much. But I’ve steadily been doing at least a few hours of work a day for the past few weeks.

A big part of it is that we’re a small team and there’s only so much I can offload to others. I know that I won’t be able to ever fully 100% be offline while working at Secfi. From things as simple as approving bank transfers to certain deals, I just simply need to be the one doing it at this point at Secfi.

The other part of it is that I’m also wired to be productive. I’d be lying if there wasn’t some times I could easily pass off but have decided to take on as well. Watching Netflix for hours is great at times, but I do get bored and find myself gravitating to being productive whether that’s working out, errands, or work.

It’s not so bad. I’m still making sure I bond with Colin as much as possible and I’m present during his wake windows. But he does sleep a lot and that gives me some windows to be productive.

Although my wife thinks I should be relaxing more, I’m not complaining by any means. Secfi and my team has been great to me and I will find more pockets of time to recharge when I need it. The company has been flexible for me and I’m happy to be flexible for the company.

On top of that, we’re on track for a monster November and a killer Q4. Taking more time to relax in the beginning of January sounds a lot better than missing out in November.

Bitcoin edges $100k

The degenerates and crypto-maxis have been out in full force since the election and it’s looking possible that Bitcoin surpasses $100k for the first time today.

There’s rumors that Trump is toiling with the idea of creating a crypto head in the White House and he’s looking to buy his own crypto exchange too.Whether he believes or even understands blockchain technology at all is to be determined, but one thing is certain and that he’s looking to at least profit off it.

I have been long Bitcoin and Ethereum for over 6 years at this point. I bought into crypto for the first time after the crash in 2018 and have mainly just been in a buy and hold pattern.

Nowadays, we’re seeing that stablecoins are becoming a staple in the U.S. with Stripe now accepting payments in stablecoins. There are a ton of other crypto uses cases that have yet to materialize though and the idea of web3 has not taken hold.

The expected easing of regulations around crypto will hopefully provide a needed boost to actual uses cases. There are real people and companies who believe in the technology and are not just in crypto for the payday.

However, degenerates will degenerate. Volatility will be high as everyone decides to become a day trader and the scams will continue to be rampant.

For me, nothing will change. I will continue to hold bitcoin and ethereum as I have the last years. I will continue to be on the lookout for great use cases. Now with a kid, I’ll sit out the majority of the degenerate trading though.

Seeing the positive side

I’m completely dumbfounded by how my baby can be the sweetest little boy for the majority of the day, and then become just an absolute nightmare for no reason. He loves to turn into a monster right after we feed at him at 3am. No amount of food, cuddles, diaper changes, or soothing seems to work between the hours of 3 and 5:30am.

I suppose we should consider ourselves lucky. I spent some good minutes on Reddit reading about other parents’ struggles with their babies and I suppose if he’s only a nightmare between 3 and 5:30am, that’s a big win comparatively.

Like with almost everything in my life, I would do better to look at the positive side of things versus focusing on the negatives. That applies to work too.

Today, I had a jerk reach out about looking for help on financing and he was just simply an asshole about things. He demanded absurd terms and had no intention of working with us. We do our best to help people and understand that our products aren’t for everyone, so these people who come in always bother me.

Again, this one asshole shouldn’t ruin things for me. For every one of these guys, we work with a ton of amazing clients that are grateful and amazing partners for us. Again, I need to focus on the positive side of things rather than the minority of the negatives.

Going back to parenting, I can only hope Colin’s 3am transformations will stop with enough time. Until then, I I should try to enjoy my bonding moments with my son during these times. And also be grateful that it’s only a 2-3 hour period of the day that he’s like this. He’s an awesome kid all around.

Distributions are coming

Pitchbook published data that VC distributions in 2023 were a 14 year low. That’s the lowest level since the great financial crisis. That’s no surprise to anyone that follow the space as there were more tech IPOs in 2008-2009 than there were in 2022-2023.

There is a severe lack of liquidity in the private markets right now. Founders and employees are starving for liquidity as well as LPs who invest in VC funds.

The only thing that can really jumpstart things is the IPO market opening back up. Luckily, we’re starting to see indicators that 2025 will be a better year for the IPO market.

ServiceTitan filed their S1 a few days ago and expects to go public in the next coming few weeks. We’re hearing that many will watch closely and hopefully follow behind them.

This feels a bit like 2020. In 2020, we saw the elction get past us and then a few tech companies such as DoorDash and AirBnb go public in December. That opened the window and a ton of companies went public in the following year.

Of course, 2020 was a different day and age. COVID was still a thing and interest rates were nearly 0. No one expects a mad rush like it was in 2020, but the consensus is that the window will open and liquidity will start flowing again. Let’s hope for the best.

The newborn downtime

We’re past the second weekend with Colin in the books and it was relatively uneventful which is obviously what we hope for. We did start getting out a bit more and we even ate out with him once. That was really fun and exciting for me. Perhaps it was less exciting for Colin who pretty much slept the entire time.

With a newborn, it’s pretty much a consistent schedule of sleep for 2 hours and be awake for 1 hour. You do this about 8 times per day. So far we’ve been lucky that Colin has been somewhat predictable and has slept well.

I’m loving every minute I have with him, but I’d also be lying if I didn’t feel cooped up and even bored at times when he is asleep. There is a lot of downtime and while it’s nice catching up on my TV shows, I’ve never done well sitting on the couch all day everyday. These last few days, I’ve had this urge to get up and do something.

Of course sacrificing for your child is part of parenthood and I’m happy to do it. We’ll also be able to go out and do more things as he ages and he gets to a more consistent schedule and ages.

In the meantime, I want to be present with my son and enjoy the newborn time. Everyone says it happens quick and they miss this phase, so I’m not taking it for granted by any means. The consistent long sleep and nap windows also allow me to get out and do things like workout which will help me fresh and on my toes.

Weekends with the baby

It’s the weekend but it hardly feels like a weekend. Two weeks into fatherhood and it feels like every day and night is just one big blur.

Just when we thought things were starting to get into a consistent schedule, Colin decides he wants to change things up and go absolutely bonkers last evening and all night. That wasn’t fun and was probably the most frustrated I’ve been since he was born.

This early newborn period has a lot of sitting and hanging out at home. As someone who is home, I’ve always struggled with that. While it is nice and does allow us to get some rest when Colin naps, I do feel a bit cooped up at home.

I’ve got a sudden urge to want to go out and do things now. The tough part is those activities are severely limited with a newborn. You don’t have a lot of time as feedings happen every 3 hours at the latest. You also simply can’t do many activities as they can get fussy.

As time goes on, Sophia and I will need to do our best to try to maintain our lives and get out as much as possible. It’s good for Colin and our sanity.