Not a victim

I’ve held a lot of anger and frustration these last few months than I have in my life. The combination of exhaustion from new fatherhood alongside the work stress has really taken a toll. When these stressful moments hit, I have recently had a tendency to blame others for the issues. Some of the things that I’ve said over the last few weeks:

“This person is causing me a lot of stress”

“I’m tired because you made me go on that weekend trip”

I’ve unfortunately let things spiral especially the last couple of months. It’s easy to play victim here when things are tough and I’ve let that creep up in my life. This isn’t me though.

One of my mantras in life is that I am responsible for everything in life whether that is good or bad. Of course that’s never fully 100% true, but it’s something I’ve lived by the last 10 years. In other words, I take full responsibility and ownership of my life and I am in control of it.

Playing victim does me no good in life and puts the blame on other people. In reality, I am in control of my life and I need to do better. I can say no to things. I can force myself to get more rest. I can get myself to a better physical and mental state. It all starts with realization though and I hope today is a good turning point to get everything back on track.

The Degenerate Era

The news of the private markets was prediction startup Polymarket raising a massive round at a $9B valuation yesterday. There’s many crazy aspects of this, but one of the things that stood out was that there are only about 50 employees at the company right now. Hats off to the Polymarket team.

When COVID hit, I fully bought into the degenerate era. Between stock picking and traditional gambling, Americans were flocking for entertainment. I definitely did not predict that the vehicle that degenerates would flock to in 2025 is through the “prediction market” startups. Of course, they are not just offering predictions on real world events anymore. They have gone into where events happen almost everyday which is in sports.

The regulatory agencies do not seem intent on slowing this down although I do see the big money casinos possibly having a say in this down the road. Regardless, the product-market fit here is proven.

Americans love to gamble and this is the era of the degenerate. We’ve only begun to get started.

Recovery and the AI upcharge

While I’m far from feeling great again, I feel a lot better than I did yesterday. My voice and energy levels are starting to come back, and I’m no longer coughing every 30 seconds. I’m viewing the next few weeks as a “recovery” period for me.

The past two months have been filled with various illnesses, exhaustion, and elevated stress levels. Some of this was was unavoidable like my son bringing home various sicknesses from daycare constantly which seems to be the norm in the fall. But of course a lot of it was very much avoidable as well with way too many trips and exhausting travel.

With our vacation next week and then the rest of October and November prior to Thanksgiving at home in New York, this is the period of recovery for me where I can focus on my physical and mental health. Life should get a lot more boring which is exactly what I need right now in my life.

On another note, it feels like the “AI upcharges” have started to hit our SaaS subscriptions. We upgraded our Slack this morning and it’s now loaded with AI features that supposedly previously weren’t there. Of course, this all came with a cost of these features and it was not a optional upgrade.

I suspect nearly everyone of my SaaS subscriptions will try to do the same. Slowing growth rates across the board for SaaS is going to create pressure to find growth in some areas. While this is all predictable and I’m not surprised, it’s going to be interesting to see what new products actually add value and what is effectively a wrapper on an existing product.

It’s only been an hour, but I have yet to see anything in my Slack look any different than before.

Slowing life down a bit

I’m finally back home after being on the road for the last 2 weeks and it was an incredibly exhausting one. Between all the personal events like a wedding, spending time with the inlaws and Colin, and traveling mixed in with a hectic work schedule, I feel like these last two weeks took years off my life.

It wasn’t all so bad though. I had a good time out in Amsterdam and then had some time with a friend in DC for the UW and Maryland game which was a lot of fun. We also closed out the quarter strong despite all the craziness. But alas, I am sitting here on a Monday at home and the cold I caught last week seems to have struck back, and I do feel like I’ve been hit by a dump truck.

Once again, my body is telling me once again that I need to do a better job taking care of it. I am 35 and I am no longer in my “youth”. Despite this, I am still very good at “powering through” when I am tired and exhausted. Whether that’s staying up for another drink with a friend despite the yawns, or simply just saying yes to a social event despite really needing a night in, I’m pretty damn good at it.

With Colin at 11 months now and both Sophia and I feeling exhausted from life, it’s a good time that we take a breather and slow down our lives a bit. That likely means more nights in and less alcohol. More healthy eating and exercise. My body and mental health could really use that break.

Time to relax

I’ve got yet another cold. I can’t tell if Colin just picked up something and gave it to me, or if I just caught something during all my travels. Either way I suppose it’s the new normal to be sick all of fall now with a kid and lack of sleep.

Luckily, the quarter is finally over and after spending the morning wrapping up on a few things, I can take some time off to relax the next few days and try to get caught up on life.

That leaves me with about a half day to go out and try to enjoy Charlottesville. It’s a gorgeous day and I need to get out and get away from my computer for a bit. I’m fortunate to have this time with Sophia, Colin, and my in-laws and I plan on focusing on that the next couple of days. It’s time to relax a bit after an exhausting quarter.

Another end of the quarter

It’s yet another end of the quarter. For better or worse, every quarter is the same with lots of deadlines going to the last minute. It’s the nature of the business as startups have lots of changes at the end of each quarter and people are busy in the last month of the quarter.

For me, I have most of the day booked to focus on closing things out. Then I’m hoping to wrap some things up in the morning tomorrow. My hope is that I’ll be able to take pretty much the rest of the week off to relax.

I’m always spent by the end of the quarter. This quarter was especially difficult with all the travel and I could use a few days of rest and some good quality time off. Luckily, I have a trip to Mexico with the family in a week and half that I’m really looking forward to. It’ll be our first extended vacation this whole year.

Before I know it, it’ll be the holidays and the end of Q4 which comes with it’s own set of challenges. My focus this month is making sure I get some good rest and get back to a good mindset. I can feel the burnout creeping up and that time off is going to be critical to make sure I’m on top of my game to close out the year strong.

A change of pace in Charlottesville

After a long week and weekend, I’ve made it to our Airbnb in Charlottesville where we’ll be staying for the week with the in-laws. As expected, it was a rough Friday of travel flying from Amsterdam to Virginia for a weekend wedding.

I made it to the welcome party for a beer and then volunteered to take Colin back to the hotel and sleep. I had a good time during the wedding on Saturday, but I bowed out early and took an Uber back with Sophia before the shuttles left. Thus is the life of a parent I suppose.

Candidly, I wasn’t very excited to be here in Charlottesville for the week. After being gone, I just wanted to be home. But now that I’m here, I’m glad we took the time. It’s great for my in-laws to get quality time with Colin and they seem to be loving being grandparents. It’s also helpful to have an extra set of hands helping out.

It’s also fun to change the scenery a bit and get out. I feel fortunate that I can work remote from here. A change of pace in my hectic life was exactly what I needed. I’m hoping to grind things out the next couple of days so I can enjoy the last two days exploring the city a bit. There’s a ton of history in the area and I’m excited to see what it has to offer.

Last day in Amsterdam

Just as I’ve started to beat the jet lag and get comfortable, I’m nearing the end of my trip to Amsterdam.

We had a great 2.5 half days with the team here so far. We spent all of Tuesday and Wednesday at an offsite planning for the next 2 years of Secfi. We touched upon everything from hiring plans to potential company trips. It was an incredibly productive couple of days.

Of course, we had to mix in some fun in the mix so we had working drinks and dinner. I’ve known everyone on the team for 4+ years now, but it is always a good idea to get together and build some camaraderie.

I decided to stay an extra day so I could hang out with the product and engineering team at our office all day. I’m not here in Amsterdam often anymore so I thought it was a good idea to dedicate an entire day to see them and also hang out a bit. I’m glad I did as it would’ve been a shame to head back last night or this morning so quickly. So today’s focus is definitely around spending time with the team more.

I do love it in Amsterdam. Perhaps after my 10th+ trip a few years ago, I took it for granted and didn’t appreciate it as much. I’m already getting sad to leave. Luckily, I have the morning tomorrow to walk around and explore a bit before my flight. Perhaps next time, I’ll carve out an entire day before or after work so I can do a proper catch-up with the city.

Hello from Amsterdam

I powered through the red eye flight and made it to the Amsterdam office with only a 20 minute power nap at my hotel. Like almost always, the thought and anxiety of the flight was a lot worse than the actual flight. I’m sitting here at 3pm Amsterdam time in fairly good spirits and energy.

The gorgeous Amsterdam day definitely helps things. I forgot just how much I love the city and Dutch culture. The Dutch are some of the best people in the world. There’s not too many other countries with such a focus on community and the environment.

Ideally, I’d have a bit more time to hang out and explore Amsterdam again. But this trip is for work and I’m hyperfocused on making the best use of my time out here. It’s going to be a great week and there’s not many better places for me to get shit done than Amsterdam.

Amsterdam

It’s Friday and I’m absolutely beat. Long hours at work and a young kid does not make life very relaxing. While I’m still overall loving being a Dad, there’s many times where I wish I could just escape life for just a week.

One of my good friends is in Bali right now for his honeymoon and I have been thinking about how nice it would be to spend a week with just Sophia on an island in Asia. The thought of being on an island with no agenda and no responsibilities is a dream right now. Of course, that’s not a reality right now. Those days will come again in the future.

For now, I’m headed to Amsterdam for work on Sunday night. While not a trip for “leisure”, I am still excited. Flying by myself without having to take care of Colin is a bit of a treat in itself. The thought of just being able to sleep in a hotel room with no monitor and alarm clock sounds amazing right now. Of course, the jet lag is probably going to play into that quite a bit, but hey I’ll take it at this point.

I am also excited to see the rest of the team. Most of which I haven’t seen in over 3 years. There’s even some team members I’ve never met in person before. It’s going to be nice being out there with everyone again.

Arrogance

I am rounding out my 7th year here at Secfi. I feel like I’ve worked 3 different jobs here during my time, and at a the same time, am always shocked at how fast these 7 years have gone. Besides our CEO and Co-Founder, I am now the longest standing employee of the company. As the say, the days are long but the years are short.

As I enter into my 8th year, one of the biggest things on top of my mind is keeping my arrogance in check. Being here for a long time means I’ve built up a lot of knowledge of the company, processes, and and history. I know what has worked and what has not worked in the past.

That’s a positive thing of course, but at the same time, it can breed a lot of arrogance. Admittedly that arrogance has come up many times this year. It’s not a good thing. We are still a small company and we need to keep a startup mentality going into things. For example, just because we’ve been doing one thing one way for years, does not mean it’s always the best way or can’t be improved.

Arrogance has ruined the careers of many people. As a college football fan, I’ve seen first hand when a star coordinator has moved up the ranks and gotten too arrogant which eventually led to their downfall. It’s important that I focus on keeping that in check so I don’t follow a similar fate in my career.

Driverless cars

One of the things I really miss in San Francisco is the driverless cars, specifically Waymo. It was an amazing way to get around. I always found it much more comfortable and enjoyable than taking most Lyfts or Ubers. On top of that, I always marveled at the human progress that was made to get to this point.

I was stoked to see that Waymo was starting to test out in New York. The city’s traffic and issues is insane. I saw my wife get stuck 3 blocks away from me while picking me up in the city this past weekend. I waited 20 minutes for her to go 3 blocks and most of the issues were solely caused by bad and selfish drivers blocking each intersection and gridlocking traffic.

In theory, driverless cars would solve most of that. Of course this is going to be a long battle. I read that there was a large protest of cab and Uber/Lyft drivers protesting Waymo coming to New York claiming that the city was too crazy for driverless cars to navigate. This is of course a convenient excuse and there’s a ton of self interest here.

I understand. People don’t want to lose their jobs and livelihoods. But I have no doubt that in the long run, a New York with driverless cars will be safer and make the city a better place. For those former drivers, I do believe there’s plenty of new opportunities for them as well in this new world that allows them to live better lives. That may be hard to see in the short-term, but I truly believe that in the long-term it will play out that way if people keep an open mind.

Correcting mistakes

It’s been a tough few weeks. For one, the team is short-handed with a paternity leave. Secondly, it’s been incredibly busy especially after Labor Day. On top of that, I have work travel next week and personal travel the week after that. So between work and personal, there’s a ton to handle.

Things the last two weeks haven’t gone according to plan. It wasn’t for a lack of preparation. Prior to the busy period, I sat down and put down my priorities to try to get through this busy period as efficiently as possible.

But sometimes, things just don’t go according to plan. Long story short, I simply just prioritized the wrong things and took the wrong bets. I don’t regret making the decisions, it was the best choices I had based on the information I had a few weeks. Things just didn’t work out with those choices as I thought.

Luckily, we have time to correct that and that starts this week for the next 2 weeks. The most important thing is to rip the band aid off and not double down on my mistakes. That starts today and I’ve reprioritized what needs to be our focus. Time to right the ship and close the quarter strong.

Gratitude Mondays

I had a great weekend in New York. We caught up with an old friend on Friday evening and had a mini-night out. Then I spent Saturday in the city, doing my favorite things in New York which is eating and exploring. On Sunday, I spent quality time with Colin just hanging out.

I’m feeling incredibly grateful for everything I have right now. Watching Colin grow has become the biggest joy in my life. He’s such an amazing kid and despite all the hard things that come with it, being a Dad absolutely rocks.

I’m also incredibly grateful for my team and my job. There’s always challenges, but push comes to shove, I get to build an incredibly firm with people I consider my friends. Not many people can say that.

Lastly, I’m grateful that I have this opportunity to be in New York again. When I left 7 years ago, I didn’t think I’d ever live back here. The opportunity to live here is something people dream their whole lives about.

The next two weeks are going to be a grind. I’m here for the next week, and then will be on the road for 2 weeks afterwards. It’s time to put my head down and get shit done.

Stepping up my AI game

I started using AI tools like ChatGPT on the regular since it first came out years ago. The progress just even in these few years since it was first launched is pretty remarkable. For me, it’s the simple things that have been the biggest game changers.

Back at my last job at PwC we used to sell a tool that would extract data from tax forms and put them in an Excel. The OCR tool was very imperfect and you’d still have to review everything, and often times fix the reader. It was a specialized tool for this specific tax form.

Nowadays, in any form of data extraction, I just put the PDF or screenshot into ChatGPT and nearly every format gets extracted to Excel spreadsheet nearly flawlessly. That is many hours worth of work that would have been eliminated at my last job. And even today, it saves me a lot of time.

ChatGPT has done wonders for me personally with the lowest hanging fruit. The very manual and menial tasks have been nearly eliminated from my workday. However, I know there is a ton of potential for further automation in my life. I know I have been slacking in this department and I’ve been doing basically the minimum with the tools at my disposal.

I definitely need to invest more time in AI proficiency and seeing what can be done to further simplify my personal and work life. That does take time, but it’ll be time well spent.

Crazy times

It’s the 24th anniversary of 9/11 and I’m in our office in lower Manhattan. While I have been in New York for the 9/11 anniversaries in the past, this time feels different just by being here. I was just 11 when 9/11 happened. I remember turning on the 10 inch TV in my Dad’s room and seeing what happened when I woke up in the morning.

I went to school and like many other classmates, I had no idea really what this meant or what happened. Of course, by watching the news, I had learned that this was a major deal and the world was going to change afterwards.

Of course, just yesterday the country dealt with another crazy situation as a shooter killed Charlie Kirk. It’s an awful situation and a incredibly dark moment for America. The country feels like we’re headed in a terrible direction of more violence and dark moments. Political views aside, any sort of violence is just a terrible stain in America.

Productivity and bad habits

In my never ending quest looking for more time through productivity, I’ve built up a lot of bad habits over the years. Perhaps the biggest of those bad habits is checking my phone when I wake up and while I get ready for the day. Not only is this bad for my mental health, it is also often counter-productive.

I wake up groggy and tired, and often the first thing I do is check my Slack and emails. This isn’t great as I’m not in a proper mindset to actually be constructive. Therefore, not much work actually gets done here. And even worse, my crankiness bleeds into some of my responses and it’s not a great situation all around.

On top of that, it is deteriorating for my mental health. In the mornings when I should be focused on getting ready and hanging out with Colin, I’m already thinking about work and not living in the present. If it’s something annoying that I have to deal with, that could put in a bad mood for the day already 10 minutes after I have woken up.

Of course, this is entirely preventable but has become a morning routine for me. It’s something I had hoped to stop years ago with mild success but me relapsing into the awful habit. This time something needs to change and I think the solution is likely very simple.

When my alarm goes off and I get up, I just need to put my phone down somewhere inaccessible until I’m ready to leave for work. Having my phone with me when I’m doing menial tasks like brushing my teeth just gives me the option to check it. It’s time to end this awful habit.

Pricing IPOs

I’m feeling a lot more like myself after finally getting some rest over the weekend. Colin is back in daycare for the first time and my sleep schedule is back to normal. I’ll chalk up the past 3 weeks as part bad luck, and part a learning experience for Sophia and I. We need to do a better job planning and saying no. Sometimes that weekend trip just isn’t worth it when we need to rest.

On another topic, the first IPO of the window will launch with Klarna on Wednesday and with Figure going public on Thursday. Then we expect Netskope to go next week.

So far, the theme of pricing fairly conservatively seems to have continued. But it appears that the increased demand has led to the bankers raising the price on these IPOs. Both Klarna and Figure have raised their IPO pricing due to demand. Netskope has announced a $6.5B initial valuation, and I expect that to also increase by the time the company lists next week.

It’s a great indication. Let’s hope that this trend continues.

Making equity decisions

It’s my job to help people with stock options in private companies navigate their decisions. I’ve been doing this for 7 years now. And I know pretty much all the ins and outs of stock options and equity.

Funny enough, it came time down to plan for my own equity in Secfi this weekend. And of course, I did what almost everyone does and procrastinated until Sunday night.

A fintech consultant who advised many of the leading fintechs once told me that financial planning is a really hard thing to get people to do because there is no immediate gratification. It’s a lot of work, and often tough decisions that you need to make today. And the benefits usually come many years down the road. As humans, we want immediate gratification.

That explanation makes sense. And despite my constant efforts telling people to plan around their equity early, I procrastinated. Making these investment decisions when it comes to you and your family’s finance can be tough.

There is no certainty that things will work out and you don’t want to make the wrong decision. And this is coming from someone that is very knowledgeable in this world.

Back on the up

After a couple decent nights of sleep and a good day of rest yesterday, I’m starting to feel like a semblance of my normal self.

The last 3-4 weeks have been absolutely brutal. We’ve had pretty much a perpetually sick kid and I’ve also had hand foot mouth alongside a cold. This also marks the first weekend home in 3 weeks so the travel has been more exhausting than fun.

During this time, work has picked up significantly and I just simply have had much time to breathe. Needless to say, I’ve been a shell of my normal self and that’s impacted a lot of areas of my life.

Of course, the only constant in life is change. Nothing last forever and I’m hoping that I’m back on the up. My illnesses are gone and Colin’s illnesses seem to be at the tail-end. I’m finally feeling decently rested again. While still not there, I’m feeling that I’m back in control of my work and life again for the first time in 3 weeks.

My travel picks up again in 2 weeks. Luckily, that gives me 2 full weekends at home in New York to rest and get caught up. Boring and relaxing is what I need right now in my life and I plan to do that.