Time, stress, and work

It’s been a tough couple of days for us. After a new good days, Colin seems to be going through his 6 week growth spurt and has been demanding an impressive amount of milk throughout the day and night.

We also have Sophia’s parents here in San Francisco for the holidays. It’s been awesome to have them here, especially since what they’ve been through the last year, but it adds another element to our already busy lives.

My hope of being pretty much unplugged for the next two weeks seems slim at best right now. Regardless, I’m hoping to keep the work to a minimal and be able to spend a lot of time with Colin, my parents and my in-laws.

I’m not sure when we’ll be able to get everyone together here for the holidays again. The work will always be there, but times like these won’t. It’s important for me to remember that as we enter the heart of the holidays.

Catering to the non-customers

One product improvement that we’re looking to tackle in early 2025 is improving the product experience for the customers that we reject.

Of course, our focus should be around bringing in customers at our target companies, i.e. the ones that can generate revenue for us. That has been and will always be our focus. However, there’s something to be said about creating a great experience even if we can’t work with you.

We have a difficult business and product. Our tools are available to all startup users for free so anyone can create an account at Secfi.com. From there, we offer two products Wealth and Liquidity solutions.

On the Wealth side, technically anyone can be a client, but the minimum cost pared means that only individuals with a lot of equity would benefit the most. Our services are personalized and 1:1 so there’s an inherent cost of assigning a personal advisor.

On the Liquidity side, we can unfortunately only work with late stage companies at this point. The subset of companies approved for a secondary or financing is less than 1% out of all the companies out there. This creates a difficult situation as quite often, people sign-up with the expectation that they should get funding.

We always respond to every request so we do not ghost individuals. However, there’s only so much feedback we can provide to every company/individual we reject. We simply just do not have the bandwidth. Most companies are just simply too early.

We can do a lot better though. There’s a lot of improvements that we can make to ensure that customers get as much info as possible. While we cannot hop on calls with every requests that we reject, we can improve our expectation setting and communication. This is one of our projects in Q1 next year.

This blog / journal going into 2025

Over time this blog has become more personal than work related for me. When I first started trying to write something daily, it was primarily driven by my desire to get better at writing for work and get comfortable with writing online.

As the years have gone on, I’ve found a lot more joy writing about my personal stuff more often than work. This blog has become more like a journal for me. It’s therapeutic and has became a place where I can write down my thoughts.

I suspect the other reason is that I’m just buried in work most days and the last thing I want to do is write more about work while living in work. I also help write our newsletter that goes out biweekly so most of my work thoughts have gone to there.

Going into 6+ years of writing this nearly daily, I still enjoy it and I want to continue doing so. I do hope to write more about more business/work/market topics though next year. I need to do a better job at consolidating those thoughts more like I do my personal thoughts.

Much needed break from social media

I probably hit my low point since Colin was born on Saturday. I was just exhausted from last week and it all hit me hard once I got to the weekend. The last two nights were great though and I’ve got a pep in my step this Monday morning.

It might be wishful thinking, but I’m hoping that now at about 6 weeks old, Colin has gotten over the early newborn sleep issue hump. He slept in one 4.5 hour stretch last night and has been going to bed and staying to sleep much easier the last few days. There will undoubtedly be setbacks, but I’m hopeful we may have gotten him to get flow.

On another note - one great byproduct of having a kid is just simply not having time to doom scroll social media. I haven’t deleted X or Instagram, but during my free times I’ve gravitated to reading more articles and playing some of the NY Times puzzle games daily.

I’ve had to become more productive since Colin was born. The lowest hanging fruit to buying more time in the day was not doom scrolling social media. I’m glad that’s happened naturally for me.

It’s been awesome and the impact on my happiness and mental health was been noticeable. Put simply, I just feel more optimistic about the world and less angry in general without spending hours in X or Instagram.

It’s a refreshing break and I recommend everyone do the same.

Don't be a d*ck

My number one rule in working with clients and partners is to not be a dick. Admittedly, it’s tough at times and there have been many moments where I want to give someone the cold shoulder or tell them to screw off. I haven’t been perfect, but I’m proud of myself for biting my tongue.

For me, it’s the simple things in my short time on this planet that may make a difference. Trying to help people when I can. Giving people the honest truth. Apologizing when I screw up or make a mistake. Being the bigger person.

Of course, we run into people all the time that don’t have that same mentality. Whether it’s someone who tries to walk all over you or use your time without the right intentions, it happens all the time. It’s often really frustrating and as much as I try to not let it get to me, it does at times.

I never really understood it. People usually want to work with people they like so you would think they would have learned by now. But perhaps they’re just miserable people all around.

I try to remind myself that for every shitty person, there are 10 other great people that I’ve enjoyed meeting and working with. This job is worth it for the 10 awesome people, not that one dick.

The new normal

After spending the first 3 days of the week from the office, I worked from home today to help Sophia out with Colin. While it is nice being around Colin and it’s been good giving Sophia a bit of a breather, it hasn’t been easy. I’m writing this at 4:25pm right now and I’m at step #1 of my checklist.

Of course, part of that is just simply craziness and calls at work that took me away from my to-do list. But Colin does what he does, and that’s making things more difficult.

My 7am and 7:30am calls were done with a noisy baby in the background feeding as he decided he wanted to sneak an extra meal in.

I wasn’t able to eat any breakfast until later in the morning as he didn’t want to get back to sleep.

The laundry, dishes, and prepping for his meals also took more hours out of my day and away from work.

I was hoping to be through my work and ready for the Niners on Thursday Night Football in 30 minutes. But alas, I’m probably playing catch-up for the next few hours during Colin’s naps.

This is the new normal with a kid. I had prepped on being more stressed and tired. That is going okay. But the drop in productivity aspect is stressful. That’s the sacrifice that parents have to make unfortunately and one that I need to get used to.

Things will get a bit easier with time and childcare help, but there will be more things that come up. For now, when I’m working from home, I’m going to have to squeeze in work where I can. That’s during naps in the early morning and late evening. I’ll also need to maximize the days I get to go to the office much more.

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.