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.

Let the games begin

The IPO window is open as many companies are on the road right now raising capital for their IPOs. By this time next week, we should see the first tech company list. Many more will follow in the week or two after.

It’ll be interesting to watch. So far, the theme has been to price the IPO at around the last priced round. Banks seem to be still erring on the conservative side with the hopes to generate a nice pop and ensure that it’s a successful IPO.

Meanwhile, Figma stock has come back down to earth which is not that surprising considering the volatility of IPO stocks. I do not expect that to have any major impact on the IPOs, but we’ll see what happens.

Let the games begin.

When the stress and anxiety is worse than the work

Yesterday was one of those high stress and skyrocketing anxiety days. The combination of being tired from the last few weeks along with Colin getting sick and having to stay home the rest of the week, on top of an anticipated busy few weeks of work was just a lot for me to handle.

Sophia and I spent most of the day just trying to survive between taking care of Colin and working. It’s not a fun time when both of us are working and we don’t have childcare. My checklist of to-dos and inbox just kept piling up.

At some point, I just needed a mental break and took 30 minutes to go destress by getting a quick workout in. It’s amazing what a little exercise and natural endorphins can do for my mind and mental state. Sometimes we all need a bit of time away to get some mental clarity.

I felt a lot better and helped get Colin to bed, cooked dinner, and then grinded out a couple hours of work before bed. When the mind is right, work seems to flow easily and everything feels productive. I’m still not there, but I was able to get a good place before a busy day of work.

Our emotions get the best of us at times, but like almost always, the stress and anxiety is almost always worse than the work that needs to be done.

When it rains, it pours

I’ve been feeling pretty brutal the last few weeks and it’s been a tough week. Colin brought home hand foot mouth a few weeks ago. The week after, we took a weekend trip to Virginia and that really took a toll on me just a few days after recovering.

I was able to power through last week, but really struggled with my energy levels most of the week. This past weekend, we had a planned trip to upstate New York which was fun, but a lot to handle. I was exhausted most of the weekend and was just happy to be home on Monday.

Of course, just as I hoped things would start to get back to normal and I could take some time to catch up on work, life, and rest, Colin may have caught yet another bug of some sort. As such, we have him home from daycare today and potentially the rest of the week which is a huge strain on both Sophia and I.

I’ve had a lot of this “learning to be a parent” moments the last few weeks especially. I never thought parenthood was easy, but even I have to admit that this was a lot harder than I thought.

Of course, a lot of the pain is on Sophia and I. We simply planned way too much this summer, and these trips absolutely exhausted all of us. I’m not happy about that and in retrospect, I should’ve been better at saying no. It was clear that we likely needed a longer more relaxing trip this summer to unwind and get away as a family, not these short weekend trips.

Luckily, we have the next 3 weekends home. I need a big reset on everything going on in life. It’s time to get some rest and get back to a nice routine. It’s going to be good to be nice and bored these next few weekends with not much on the schedule.

September

Things are starting to slow down around the office which is nice. I have a busy day today and fully plan to take my mind off everything for the next 4 days. I need a good reset and would like to get my mind in a good place for what will be a busy September. Luckily, I’m back home for a few weekends before my travel schedule picks up at the end of September and in October.

My mindset is to get through September and take some good time off in October to prepare myself for the end of year push which is never an easy time for us at Secfi.

Right now, everything feels like it’s about to pick up significantly in September. People will be back from vacations and the IPO market is going to open up leading to much more activity in the private markets. For the first time in a long time, people are thinking about IPOs and their equity again.

It’s a good feeling and it finally feels like we’ve made it through the down cycle after 3 years.

Secfi New York

We had 11 people in our office yesterday for meetings. I love getting the team together and doing in-person meetings. Of course, with distributed team members, we’ll never fully be 100% in-office so some folks had to dial-in, but I cannot stress how much better being in-person is than being fully remote.

It is simply a lot more efficient the majority of the time. We get to learn from each other more. Collaborating on a project or topic is as easy as turning around and asking, versus asking to schedule time.

Going forward, it’s going to be one of our priorities to get most of the team out here to New York quarterly.

The Gov't takes over

It’s an interesting time in our world right now as the President is looking to expand the Federal government’s power.

He’s brought in the National Guard to help control crime in Washington D.C. He’s been vocal about trying to control the Federal Reserve. The U.S. has now acquired 10% of Intel and there’s rumors that the administration is considering taking more stakes in companies.

For years, we blasted the “socialist” countries for taking stakes in their companies like the Europeans with Airbus and China controlling most of their companies. Now we’ve decided to do the same.

I’m not sure how to feel about it. On one hand - it gave these companies unfair advantages with the backing of the government. On the other hand - it feels un-American in many ways and allows the government to get involved with these companies. While the gov’t is always going to be involved through regulation, seeing them acquire a direct stake in the company is a much different animal.

It’s an interesting time right now and will likely create precedent for the government’s future control and policies.

Bring on the Fall

I’m absolutely beat after another fun but long weekend. We drove down to Virginia to see some friends and their kids. It was a ton of fun but these 5+ hour drives for the weekend are absolutely killing my energy levels.

We have one more trip to upstate New York this weekend. Thankfully it’s a much shorter drive and we’ll have an extra day up there. But mostly, I am looking forward to just being back in New York for a few weekends.

This would normally be a dead week for us with Labor Day coming up. But it’s not an ordinary year with a lot of IPOs on the horizon. We have the team coming in to New York tomorrow to do a lot planning and prep for the weeks ahead.

It’s going to be a fun and busy week as we prepare for some craziness on the other side of Labor Day. Luckily, I’ll have 3 weekends at home in New York during those weeks so I can get back on a routine and maximize my work hours.

It’s been a long summer with the move to New York and all these trips. I’m more than ready for the Fall and some time home watching football.

Friday

I’m absolutely beat after a long but productive week. While I quarantined at home over the weekend and beginning of the week, I had a lot of extra time that I normally don’t have and I spent a good chunk of that grinding out work. I finally got back into the office yesterday and basically ran around for 9 hours straight hopping from meeting to call.

Luckily I’m taking most of today off to drive down to Virginia so we can see friends and hang out at their house this weekend. It’s going to be a nice much needed break and will be nice to get outside after quarantining all last weekend.

August so far has been anything but calm with everything going on. That’s a good thing for the business but also stressful. I’m finding myself pushing some meetings out another week or two in advance as I simply just don’t have time to take some of these calls anymore. Some things simply just have to wait as life and other priorities need to take precedent.

The AI bubble

Last week’s news in tech has been around Sam Altman saying that there is definitely an AI bubble and that a lot of investors will get burned. Like always, the media made it a lot more controversial than it really was. This is the consensus among pretty much all investors.

Bubbles always form when there’s a new technology put out there. For every winner, there’s going to be 10s of losers out there where people will lose money. On one hand, that is the nature of venture capital.

At the same time, this admittedly feels a bit crazier with the valuations of these companies where they are at. The size of the bubble is definitely much bigger today than it was in previous bubbles such as crypto or social media. At the same time, these companies are also making and growing faster than we’ve ever seen before.

Ultimately, I think this all ends very similar to how the last bubbles ended. We’ll go through the peaks and valleys, but ultimately there will be a few very large game changing companies out there. And there’s going to be a lot of companies that don’t make it. That part to me is the easy part. The bigger question is when and how.

Battling context switching

A few months ago, I started blocking off my calendar on Wednesdays every couple of weeks or so in order to really sit down and grind some work out. It was great, but inevitably that started to go away as urgent meetings started showing up and slowly my protected Wednesdays disappeared.

Eventually, I just stopped blocking off my calendar altogether. And yet another productivity experiment had initial success and then became a failed experiment in the long-run. At the beginning of this week, I decide to block off my entire Wednesday again and have a get shit done day.

It’s been great so far and I haven’t been this excited for a day of work in a long time. There’s just been so much shit that I’ve wanted to do from a strategic and more creative side that I’ve wanted to tackle, but just haven’t had any prolonged blocks to do so.

Going forward, I know that blocking off my Wednesdays is just not manageable. And I’ll need to make to make adjustments.

In addition, my call schedule often creates a lot of context switching. I take a 30 minute call, and then have a 30 minute window until my next call. Those 30 minutes are just not enough time for me to sit down and really tackle a lot of these tasks. As such, I use those minutes to catch-up on Slack/Email and sometimes even take a break. It’s not the most productive use of my time.

My new experiment is going to be trying to adjust my calendar on Fridays for the week ahead. I’ll put in 2-4 hour blocks of time where I try to protect myself from calls and meetings so I can focus on these projects that take longer. I’m hoping this experiment lasts a bit longer and allows me to be more productive

A blessing in disguise

I'm through the worse of HFM and feel mostly normal except for these odd sores on my hands and feet. It definitely doesn’t look great so I’ve been mostly staying home. After being mostly quarantined in my room since Friday, I’m really starting to get the itch to get back out.

I will say it has been nice getting some rest and also getting caught up on a lot of things. I was able to get a ton done personally and at work, and I finally feel caught up with everything. It’s amazing what happens when you eliminate your social life and role as a parent for a few days.

While I definitely wouldn’t wish this illness on anyone, I’m starting to view it as a bit of a blessing in disguise. I really needed a break and a rest from the grind, and well getting HFM in a weird way gave me that opportunity.

On the personal and work front, I really just needed some extra hours to get caught up with everything that has been piling up. I was able to effectively get through my backlog of personal items and even booked a family vacation during my time.

As a parent, you don’t get 3-6 hour blocks of alone time often and I was able to take advantage of that. Maybe it’s a good idea for Sophia and I to try to manufacture these break periods every now and then for each other. We can choose a weekend where we eliminate our social lives and then alternate days where one of us just rests and catches up on life.

My battle with hand, foot, and mouth

Well it turned out that I was not only sick, but I was sick with maybe one of the most gruesome viruses out there, hand foot mouth. I ended up working more or less a full day on Friday thinking I had something like strep or a bad cold. My strep tests came back negative and I figured that I had something else.

Unfortunately, on Saturday the dreaded red spots on my hands and feet started to show up and I knew instantly that I caught HFM. Shit is a horrible virus that feels straight out of something you hear from the middle ages. You start out with a horrible fever and chills for 24-48 hours, and then once that subsides, the sores start showing up.

The sores start out itchy. Not as bad as a mosquito bite, but being that they are on palms and soles of the feet, it makes things a lot worse. Then the sores start to really sore up in the back of your throat making swallowing anything painful. Sleeping is tough as you’re constantly dealing with itchy palms and soles.

As such, I have not left the house since my Friday strep test mainly staying in my room. It hasn’t been a fun experience but I tried to make the best of it and really just relax, rest, and do nothing. While this is not a desirable circumstance to be lazy, I also realize that I simply just have not had the chance to do anything like this in many years.

I spent most of Saturday in bed alternating between watching movies and napping. Minus the whole feeling like shit thing, it was actually really nice to get some down time. Sunday was more or less of the same, but I sprinkled in productivity in half my day. I caught up on work and then booked our family vacation in October which I had been putting off for some time.

Of course, the most painful part of this is not being able to hang out with Colin. It was heartbreaking watching him crawl to me and want to hang out, but not being able to pick him up or hug him.

I’m hoping that in the next day or two, I’ll actually be able to be a human again and get out in the world. I’m making the best of it, but being locked up in a room isn’t something that I’m generally good at. Although, if I’m being honest, lots of parts of being locked in a room for the weekend was kind of nice. Maybe I should try being incredibly lazy more often.