Changing up my routine

When I’m working, I’m a creature of habit and like my set routines in order to be as efficient as possible. I go into the office Monday-Thursday and try to be at my desk at 8am. I work out in the afternoons or early evenings and do the same class once or twice a week. Sophia and I cook our workday meals at home, and then finish up work or lounge on the couch watching TV.

Recently, I’ve been feeling that things have been a bit stale. I don’t like doing too much on weekdays to make sure I get enough rest to be efficient at work so my weekdays can seem a bit just boring.

This past week I decided to change things up a bit. Instead of my traditional running class on Wednesdays, I decided to get 9 holes in after work with some friends. On Thursday, we went out to a casual dinner instead of cooking at home. It’s minor changes, but I sit here writing this on Friday and feel a bit more energized heading into the weekend.

It’s a good reminder for myself that I need to go out and enjoy life a bit more and change up my routines from time to time on the weekdays. I hope to try new things in the future like new workout classes or other hobbies.

Prioritizing

I dug my own grave on Monday this week when I said this looks like a light and easy week. It’s the first week of August which is a very popular vacation time and my schedule was wide open. I was hoping to spend the time working through my checklist of to-dos that have been put on hold because of deals.

Of course, it never works out that way. My schedule quickly filled up a ton of unexpected tasks and I am running severely behind on Thursday. After working at a startup for the last 6 years, I should’ve been smarter to know better.

While I perhaps haven’t gotten wiser on that front, I will say that I have definitely gotten a lot better at prioritizing and making sure not to stress too much about everything. Long checklists of to-dos used to give me endless stress, but I’ve learned that is just the norm here when you’re one of the leaders of a startup.

There’s never a shortage of things to do. Ever. Unfortunately, that means that I’m pretty much always perpetually behind where I want to be. That’s part of the life here and I wouldn’t have it any other way.

The Walz VP Pick

The news of yesterday was that Kamala Harris has chosen Jim Walz as her VP candidate. I am a Shapiro fan and thought that would be the best pick, but I’m growing to like Walz a lot. I am far from a political strategist, but it seems that the idea here is to choose someone who can relate to the parts of the country that Kamala does not as well.

Simply put, he’s from the Midwest and speaks like someone from there. He is a veteran who was a former school teacher and football coach. He is wildly different than the prosecutor from the Bay Area, and I’d imagine the hope is that he can help win the Midwest for the Democrats.

So far so good from what I’m seeing from Kamal and Walz. Their rallies and speeches have been electric and they do a good job balancing attacks on Trump/Vance with humor. It’s a night and day difference from the Biden era.

So far we’ve seen Kamala’s team really lean into social media and speak to the younger generation. A month ago, I had thought that the election was all but wrapped up for Trump and the Republicans, but things have gotten a lot more interesting.

It’s still a long ways to go and I want to hear more from Kamal and Walz before I get too excited. But I have hope again which is all we can ask for.

Attacking this day with enthusiasm unknown to mankind

I have a love/hate relationship with Jim Harbaugh. He’s a hell of a football coach that almost led my 49ers to our first Super Bowl since 1994. He had a falling out with the organization and was ousted. He eventually took the job with Michigan and ended up beating my Washington Huskies last year in the national championship.

He’s a bit of an asshole. He rubs people the wrong way. He’s gotten caught cheating and he’s currently under fire for what he did last year with Connor Stallions. All that said, he’s a hell of a football coach and wins.

His sayings and antics corny are as corny as they are effective. I suspect that it works for him because that’s truly who he is. He lives and breathes what he says. He’s not someone to say something and then act differently behind closed doors.

I was listing to Harbaugh on one of my podcasts and one of his famous lines is “attack this day with enthusiasm unknown to mankind”. I didn’t really pay much attention to that in the past or know what it truly meant until listening to him speak about it on this podcast.

In short, he uses this phrase to encourage people to take control of their day. He never liked when people told him “have a great day”, because he wanted to take control and make it a good day. I loved that.

Listening to him speak about this corny saying made me realize that I have fallen a bit into a pattern of lethargy. My weekday pattern recently has been wake up, go to work, workout, go home, cook dinner, watch some TV and go to sleep. I live a good and happy life, but I had not been looking to make my day great.

In other words, I wasn’t attacking everyday with enthusiasm unknown to mankind. Perhaps the opposite actually. Every day on earth is a gift and I don’t know many days I have left. I might as well make every day the best I can when it comes to work, workouts, or fun.

The old internet

At this morning’s team meeting, we had a fun chat about the new generation entering the workforce and also what the old work life was like.

I don’t believe anyone in Gen Z really knows what the classic “I’m on the phone” sign with your hands mean nowadays. They grew up in age of smart phones and I’m not sure if many of them have ever used a typical desktop phone.

Even when I started work 10 years ago, every work station had a phone on the table and we would always call people rather than Slacking them. I think a new hire Gen Z graduate might panic if someone told them to call them via a deskphone nowadays.

I remember back in the day when we had to use dial-up internet and block a phone line to reach the internet. We were never permanently online when we were kids. Now, you can’t be offline.

Downloading a MP3 could take hours and often your download would be interrupted, and you’d have to start the 2 hour process again. I remember having to load my iPod with music and having to delete songs to make room for new music. It’s crazy to think cause now you have the world’s library of music at your fingerprints to instantly play at any moment.

Imagine what life will be like in the next 25 year.

Noise in the markets

It’s generally been a good year for the markets so far. The S&P 500 is up 14.8% YTD. Things have started to stabilize a bit on the inflation front and rate cuts seem to be on the horizon.

As we head into the second half of the year, there seems to be a lot of fear around potential war in the Middle East and the election coming up. As I write this, the S&P 500 is down 1.8% today.

For personal reasons, I don’t pay much attention to the daily changes in the market. I invest for the long-term so the daily fluctuations are simply noise to me.

For work though, we’re also in it for the long-haul and I feel fortunate to not work in a finance job where the daily changes in the market impact my decisions greatly. Of course, we do pay attention to what’s happening in the public markets as it impacts our views in the private markets.

No one likes to see red days like today and no one knows what will happen in these next few months for sure. I do know that there will be a lot more red days and perhaps weeks/months ahead. We knew this could be a tough Q3 and possibly Q4 due to the events in the world.

We’re bracing ourselves, but also hoping for the best. It’s part of the cost of being an investor.

Shitty people

One unfortunate truth that I’ve learned as I get older is that there’s just a ton of shitty people everywhere. It’s obviously a wide spectrum from people who just don’t care about others to being a downright awful person. It’s evident everywhere from work to just walking around day to day.

The internet is full of scammers and people pretending to be who they are not to take advantage of others. There’s that one asshole who opens their car door and drops their litter on the ground. I meet individuals often who will outright lie in order to get paid first.

It can be disheartening at times to see how shitty humans can be. I try to tell myself that everyone’s situation is different and perhaps they were just dealt an awful hand in life which caused them to be this way. Or perhaps they were hurt by others or taught wrongly and if it wasn’t for that, they wouldn’t be that way.

Regardless the reason, I need to do a better job at seeing the good in the world. The reality is that there are more good people than shitty people by a large margin. Unfortunately, the shitty people just tend to stand out more than the rest.

That person that does or says something awful to me can upset me and ruin my day. But the awesome person who helps pick up my headphones after I drop them doesn’t make my day. That’s a bad way to go about life and my own fault.

There’s always going to be people that are shit humans. Karma will take care of them. In the meantime, I need to focus on the good in the world.

Getting older and (possibly) wiser

I am 34 and the last couple years I’ve finally started “feeling old”. Perhaps old is the wrong word and adult maybe the better way to phrase things.

I value my sleep and rest over social life. I feel tired all the time. I no longer get excited for parties, but I do get excited to run errands and go to random stores like Home Depot.

With a baby on the way, I feel very ready to enter the next phase of my life. Of course I’ll miss the 3am nights with friends drinking every now and then, but it’s just not worth it anymore at this age. I look forward to trading in my 3am “nightcap” for a 3am baby feeding session.

Of course there’s a lot of positives to aging. I do feel much wiser. I listen more (but not enough). I know more of how the world works. I don’t let things that don’t matter bother me as much as I used to.

I feel that I’ve become a much better person overall. I’m proud of that part of my life, but I’m equally as proud to that I know that I have a lot of room to grow still.

If I do things right, I know that life should only get better as I age. I look forward to that.

New Mexico

For the second year in a row, Sophia and I went spent the weekend in Santa Fe, New Mexico with her parents during the annual Spanish Market. Her parents have been coming to this event for 30 years and we wanted to be there to help them attend again this year.

This year was much different than last given my father in-law’s stroke. It was tough to see at times. Sophia and I had much more alone time to explore New Mexico last year which we didn’t have this time around as we had to take care of him much of the trip. But despite moving a lot slower nowadays, he still remembers nearly everything about Santa Fe which was remarkable to see.

It was a fun weekend at times, but it was also a difficult one. We knew going in that this wasn’t really a vacation for Sophia or I. This was about spending time with family and ensuring her parents had a good time. It was great to see her parents really enjoying the weekend and have a sense of normalcy after a tough year.

The Democrats and tech

For the last 8+ years, I’ve had many issues with the way with the Democrats have handled most things. The party seems very fractured amongst the far left and the more moderate democrats. The reality is that most of the country is more moderate and the Dems have done an awful job relating to a lot of these folks.

I personally view that social issues outweigh any economic issues in this country so I’m remained steadfast in my commitment to not vote for Trump. But I’ve been more and more disgruntled by the direction of the party.

In regards to tech, it seems that the Dems have just decided to declare war on anyone rich. While there are obviously really shitty rich people out, I don’t subscribe to the thought that any billionaire is a bad person and we need to wage war on them.

This war on billionaires has naturally extended to the war on tech and has caused a rift in the typically very liberal Silicon Valley. This is not a good thing.

Yes, tech has created a lot of wealth, but it has also increased the pie and driven economic growth in the last 10 years. There has been a lot of innovation that has benefited Americans.

Yet, the focus among the Dems isn’t how much tech can improve the country, but rather on the individuals that have generated wealth. Tech has historically been a huge ally to the Democrats and most of their causes.

Until the Democrats can change their strategy here, they will continue to lose support. Given that the future is tech, that’s not a great sign for the party. I hope new leaders can finally figure this out and right the ship.

Wasteful spending

Like a lot of other startups, I feel like we had a ton of wasteful spend back in the early days of the company. When you raise VC money and hire a ton, it was just easy to get lost in software subscriptions, hardware for employees, and stuff for the office.

You start with a cheaper software subscription, add users, and then people forget to monitor that subscription and we run into auto-renewal despite perhaps not using it for the seats we have.

You allow an employee to buy tools to make them more efficient, but then everyone wants that extra monitor, chargers, etc.

We all want swag, but order extra just in case which ends up sitting in a box in the office or in the storage unit.

Unfortunately a lot of the spend didn’t contribute much on the ROI front. I’ve spent some hours this summer donating a lot of these things to high school organizations and Goodwill so that at least someone can use it.

We don’t want to be a company that penny pinches and counts paperclips. But wasteful spending is painful when you start to unravel these things. We’ve done a lot of good work being more diligent about our spend these last couple of years and it’s something I’m proud of.

What is a con-man?

I used to think that conman was just the word for describing a thief. It is widely used today that way. However, the origins of “con” was simply just short for confidence. In other words, it’s someone who has a ton of confidence in what they do.

Someone who wants to make a living as a thief or deceiving someone needs to have confidence to do so. They are just simply incredible at convincing someone else that they are someone they are not.

I am a Democrat born in San Francisco, but I am probably far from the stereotype of one. My views generally align more with the Democratic Party, but I have been just as critical of the far left as I have about the far right. I think the Democratic party needs some serious self-reflection even if they are able to win this election.

However, there’s one thing I know and that’s I believe Trump is a conman who struggles to tell the truth. I think he is in the race solely for his own grab for power, not for the good of the country. For everyone’s sake, I hope I can change my mind on him. But I’ve seen enough over the last 8+ years to form my opinion.

This won’t be a fun 3+ months in America. But I hope that I can write that I’m proud of the way the country reacted. We’ll see.

100 years

I am currently listening to Dan Carlin’s “Blueprint for Armageddon” podcast series which goes over World War I. I have always loved history. I always had a fascination about how the modern world has been shaped by the past.

Of course, I’ve been addicted to listening ever since I started the series considering that the shooting of Archduke Franz Ferdinand kicked off the shaping of the modern world. Prior to WWI, the planet had not yet seen a war between the great powers for 99 years since Napoleon.

Today in 2024, it’s been almost 80 years since World War 2 ended and 100 years since World War 1 began. The dynamics are of course different this time around with nuclear weapons. But I’d be lying if I said the “blueprint” for a global war is much different this time around.

We have world powers vying to be the top of the food chain. We have alliances supporting each of these world powers. As we’ve seen in the past, one shot could spark a global war and shape the world for the next 100 years. Let’s hope history doesn’t repeat itself this time around.

The AI age

We’ve had the pleasure of having Cody who is a recent high school graduate as our summer intern. It’s been a lot of fun having him here for the past few weeks. As an incoming college freshman, Cody’s work for the company has been more geared towards him learning the ropes of what it’s like to be in the workforce.

He’s joined multiple members of the team on calls and done a few job shadows. We’ve also set him up with a capstone project which is to research a company that we should invest in. I was not surprised to see him pick Canva as he’s had experience using it during school.

Kids these days definitely have an abundance of tools and resources and it’s awesome to see. I feel fortunate to grow up in the internet age. I can only imagine what it’s like growing up in the AI age.

I’m happy that my kids will not have to go to the library to checkout books to do research. The world’s biggest library is at their fingertips and can be accessed with a quick prompt. The pains of manual repetitive tasks will be gone by the time my son hits the workforce. I’m glad he doesn’t have to spend much of his first years in the job force doing a lot of copying and pasting.

I remember the older folks in my first job talking about the awful things they had to do when they were early in the workforce like manually printing reports and stapling thousands of copies together. In 18 years when my kid has his first job, I’ll gladly be that old guy talking about how awful the first few years of work were.

Office presence

Over the next month or so, I have a decision to make on whether I want to move our family back out to New York. There are many personal reasons which I don’t feel like discussing right now, but from purely a work perspective it makes a ton of sense.

We are building our office presence in New York primarily. All our recent hires have been focused in New York. While having a San Francisco office and presence is nice, we have made the decision that we won’t build out the office here any further. Simply put the office culture in San Francisco is more or less dead as everyone wants to work remote.

It does make sense for me to be out there in New York to help build out the office. Most of our partners and LPs are based on the east coast now as well.

From a personal work perspective, I dearly miss having coworkers to talk and hang out with. I’ve been pretty much by myself in the office for the last 2 years and it definitely gets lonely and has been impacting my moods. Even with Zoom readily available, it is definitely not the same vibe.

Work reasons of course are just one factor. And the harder part will be the personal impact on my family and I.

Things are getting ugly

I was out of pocket for most of the day on Saturday and found about the assassination attempt along with a group of friends at the same time. When someone mentioned that Trump was shot, I thought it was just a bad joke. I’m glad Trump is okay, but a brutal election just got a whole lot uglier.

I had known that was going to be a tough election for all of us, no matter what side we’re on, but I definitely did not have an assination attempt on my bingo card. The country is incredibly divided and this summer and fall is going to be bring out a level of nastiness that I’m definitely not looking forward to.

Baby fever

It’s a gorgeous Friday here in San Francisco. The theme of the weekend for me is baby advice. I’m heading to a birthday party where we will be the only ones without a kid. I’m going to be a sponge and just listen on everything from stroller recs to surviving the first 3 months.

The baby industry is incredibly overwhelming. As much fun as it is shopping for cool shit for my unborn child, there seems to be a million companies all making the same thing or variations of the same thing.

There are some fun things I plan on sneaking into the registry without telling Sophia. I can’t wait to see her face when I put a sushi costume on the baby.

The unfun parts about running a business

Often times entrepreneurship and startups get glorified in the media and amongst those who haven’t gone through the journey yet. Don’t get me wrong, I don’t think there’s a better path to growth and starting a company in my opinion is the greatest thing you can do with your career. But yet, everyone talks about the glory and doesn’t really focus on the journey to get there.

Sophia and I are watching season 3 of The Bear and it’s one of my favorite TV shows. There was a flashback scene where the restaurant owner was talking about all the shitty parts about running a restaurant such as the toilet exploding constantly. I’ve never run a restaurant, but I can definitely relate to a lot of the shitty things that come along with running a business.

For example, I’ve been on the phone on and off nearly all morning with one of our banks trying to get someone access to our accounts. I’ve also had to manually download account statements for a visa application for one of our employees. All necessary and important things, but of course I’d rather be doing other tasks like generating revenue.

It all comes as part of the job though. As Mikey in The Bear said, it sucks but he wouldn’t want to be doing anything else.

Just how big can big tech get?

Most of the market gains in tech this year have been driven by big tech with Google, Apple, Microsoft, Meta, and Amazon leading the way. Tech in general has been largely propped up by investors pumping money into big tech to capitalize on the AI boom. Big tech has undoubtedly been the biggest benefactors of the AI trends and I don’t see that stopping anytime soon.

I am using a Windows PC to write this blog post. I have an Apple iPhone. I use google personally and for work. I scrolled Instagram this morning while I commuted. And I will probably buy something on Amazon this week. AI will continue to further our dependence on these tech tools as they are implemented in our already everyday devices and platforms.

The news today is that Alphabet is looking to acquire Hubspot which is a $25B+ CRM that powers a large chunk of the world’s businesses. Alphabet is already a $2T+ business so they are one of the few handful of companies that could acquire a $25B+ company today.

I wonder just how large big tech can get. Will we live in a world where Google, Microsoft, Apple, and Amazon control pretty much everything? How big is too big? At what point does big tech get to the point where innovation is stalled as no one can compete?

Regulators are already all over big tech. We are seeing a modern day Rockefeller evolve in real time. It’s hard to see big tech not continue to dominate in the short-term as they are the biggest benefactors in the AI boom. But perhaps this AI boom will be the straw that breaks the camels back.

Sell in May and go away

I feel energized and on top of the world right now. After a sluggish jet lagged Monday, I got a tough workout in and slept like a baby. I haven’t felt this energized and motivated at work in what feels like months. Again, another reminder that I need breaks more often and I need to treat my body better.

There’s a saying in finance that goes “sell in May and go away” which goes to describe the summer mentality of investors. The idea behind the quote is that stocks go down in the summer so it’s best to sell. Of course - that’s a saying and not particularly great blanket financial advice that we don’t adhere to.

However, more accurately is that the summer months are typically slower in the finance world. I myself just got back from a two week trip and many of our team is out of office. Our partners are also shuffling in and out of the office the next couple of months.

For us, the deals don’t stop and we’re going to be grinding to make sure we have a good summer. But it’s also an opportunity for us to take a step back and work on some other projects that will be crucial for us to close out the year strong. I plan on taking full advantage of the “slower” summer months.