The AI paradigm shift

For one reason or another, my random thoughts on my run yesterday were around how the people interact with the internet and how that’s evolved over time.

In the adoption of the internet in the 1990s and 2000s, users interacted through web pages on desktops or laptops. We’d use Netscape or Internet Explorer to go to a website created on Geocities. In the beginning, everything was static and mostly text based. Things got prettier and more dynamic over time and by the end of the 2000s, we had embedded videos and more interactive websites.

Everything changed with the adoption of mobile in the 2010s. We had armies of product managers and engineers making beautiful responsive webpages and apps. To encourage adoption and use, these apps were gamified and companies got very good at getting you to engage with the app. You needed a beautiful and easy to use app for that, and companies layered on incentives to use that app more.

There’s been an interesting shift in the last few years. While we still live on mobile and apps on a day to day basis, there seems to be a paradigm shift back to the old days of barebones and text based apps. ChatGPT’s website looks basic in black and white, and looks more like a Geocities webstie than let’s say DoorDash’s page.

I do believe both styles are here to stay of course. Tik-Tok and Instagram are still out there and one of the most popular apps in the world. But there seems to be a shift in how users consume information and we may be shifting back slightly back to a traditional text based learning. That will likely change as AI evolves. Voice and video are very interesting and perhaps sooner or later, we’ll have a ChatGPT narrator reading back answers to our prompts.

Colin is 9 months today

It’s almost a bit surreal but Colin is now 9 months old today. It was an eventful last 3 months. We moved to New York, put him into daycare, and experienced a lot of firsts. He started eating solid foods and started crawling. I had heard things move very fast in that first year and I can attest that it is the case.

As soon as it feels like they hit a period of time, it goes by quickly and next thing you know they’re onto to the next thing. It’s only going to be a matter of time until he’s walking and talking. For Mom and I, it’s been a big 9 months of figuring out how to parent.

We’re back in New York after spending almost 2 weeks in Seattle and San Francisco attending a wedding and visiting friends and family. I suppose we should consider ourselves baby travel veterans at this point as Colin took his 6th flight yesterday, 3 of which were cross country and 2 others going from SF to Hawaii.

Like most things Colin has taken on, he was a champ. We feel fortunate that we have a relatively easy baby that goes with the flow. After flying to Seattle, he had one morning with an early wake-up and then adjusted to the time zone the next day. After flying back and getting in the late afternoon, he had one wake up at 8:30 for about an hour and then slept through the night.

I realize how lucky Sophia and I are. We do focus a lot on schedule and sleep training, but at the same time, I know a lot of this is the luck of the draw. Despite being an easy kid that travels well, Sophia and I have learned a lot.

Traveling with a kid, even an easy one, is undoubtedly a lot harder and stressful. You have a ton to pack and plan around. There are many moments where he just doesn’t want to sit still and it’s an arm workout holding him for hours at a time. Traveling even by yourself across the country is tiring and stressful, and has always thrown me off for at least a day. With a kid, you’ll need a lot more recovery time.

At the same time, most of the stress and anxiety comes from my own head often. I had a ton of anxiety before this trip. I lost a bit of sleep thinking about how stressful the trip would be. Afterall, it was a great trip where everything worked out and I was glad we had the opportunity.

In these 9 months, I think my biggest learning is that I need to roll with the punches more and just embrace the situation. Having a kid is hard and a trip with him won’t ever be like it was before. But that’s part of life and there’s a lot of beauty in that as well. I should feel fortunate that I’m able to take Colin with us on these trips rather than stress about it. Everything always works out and I need to remember that.

Figma's IPO

I had a blast doing a solo parent yesterday with Colin as Sophia went into the office. I mostly took the day off and took Colin to the Bay Area Discovery Museum which was a ton of fun. He got to crawl and climb on everything there and I got to relax a bit knowing that everything was baby safe. Watching him grow and seeing his personality evolve has been a joy. Even with the stress of him pooping 3 times including one all over his pack and play was worth it.

In other news, Figma went public yesterday at $33 per share and opened at $85 per share. The stock closed the day at $115.50. We’ll see if it holds, but this appears to be a brutal mispricing by the bankers for a household tech name.

I expect to see a ton of VCs including Bill Gurley get back on the microphone blasting these traditional IPOs. On one hand, it’s good for employees as the stock price did go up which is what you want. On the other hand, the company sold shares at $33 when it was evident that they could have sold them at a much higher price.

I wonder what the discussions were around a potential direct listing. Admittedly I have not dug into the financials of Figma at all, but if they did not need the cash then this likely would have been a much better situation for everyone if they just went the direct listing route.

Not every company has the ability to do a direct listing, but for a company with a brand name like Figma, it could have made a lot more sense. I’m excited to dig into the commentary on this in the future by VCs and other investors out there.

San Francisco's comeback

It’s only been 3 months since I’ve left SF but it’s hard to ignore the work that new Mayor Daniel Lurie has done. It seems that new restaurants and stores are reinvesting in San Francisco again.

Take Jins, a Japanese eyeglass company, for example. They used to have a location in Union Square San Francisco many for years and shut down in 2022 like many other downtown businesses after COVID. Well, just down the street from my Dad’s house is a new billboard saying Jins is coming back to San Francisco in the Stonestown Mall.

It was good to see that companies are believing in San Francisco again. Many other areas of the city are being built up while downtown and the traditional tourist zones make a recovery. It’ll take awhile for downtown to get back to where it was, but there’s been a ton of companies pledging to stay recently.

I have fond memories of going to Union Square as a kid on a weekly basis with my Dad. And then shopping around the area for Christmas. I hope my kid has that same experience as I did growing up. The city seems to be on the right path and I’m loving what I’m seeing.

The kid grind

I always knew raising kids was hard but nothing can really prepare you for it until you actually do it. A friend said that she is “basically trying to survive everyday”. It is indeed a grind nearly every day.

Sophia and I are back home in San Francisco without childcare for the week. So we are alternating between working and taking care of Colin. Even with both parents here and a decent sized house for Colin to roam around, things are difficult.

There’s really not much time to relax and chill. During the day, we’re lucky to get 3-4 hours while Colin naps for both of us to feed ourselves, run errands, and catch up on work. Probably the most difficult part is trying to make sure that I’m caught up on work.

As such, I was up late last night after getting Colin to bed catching up. There’s definitely a feeling that I’m always behind though as I just have less hours in the day than I used to. I’m getting better at it, but we’re also learning how to parent on the job. Things will hopefully continue to get easier.

Recruiting in the age of AI

We’re back to hiring for the team again and it’s been fun. We’ve had to put hiring on my team on pause for the last six months with the uncertainty of the market. It was the right decision but also a stressful one as the existing team took on more work as we grew.

A big difference this time compared to the last times we hired extensively is the growth of AI. Cover letters and case studies can be put together in a matter of minutes using tools like ChatGPT.

I am generally not a huge fan of cover letters, but I do believe it’s a requirement to apply for the role to the join the team. In the days of LinkedIn Easy Apply, we get way too many applicants that are not serious about the role. Even with a required cover letter, we get a ton of applications who side step the requirement and do not submit one.

Of course nowadays with ChatGPT, we need to be careful that the person actually spent time reading about the role and position. I have no issues with people using ChatGPT to help write the cover letter, but it’s very obvious when someone has clearly just plugged the job description into the app and added no personalization just to get an application in.

That’s exactly what we’re trying to weed out. We want people excited about the job. We get the most out of our employees when they are happy and excited about their work.

Furthermore, ChatGPT also complicates the case study side of things. In previous years, we’d send a case study a day ahead and let the individuals present to us the next day. In the era of AI, I no longer believe that this is a good way to test what we’re looking for in a candidate. To combat that, we’ll likely bring a candidate in and let them use any tools possible to do their best but do it under a time pressure.

This will be a good learning experience for us as we navigate this new world.

Long weekend thoughts

I’m back home in San Francisco after spending 5 days in Washington State. We had a fun visit to our friends who bought a house in Marysville and then we took the ferry to Lopez Island for my other friend’s wedding.

I saw a ton of old friends and acquaintances from college and our early New York days. I feel fortunate that I graduated from UW 13 years ago and still can go and say hi to everyone, and catch-up like we were still sitting at a party when we were 22.

Now that we’re all between 35-40, the conversations have definitely shifted to talking about our kids and homes that we’re all buying. It’s a stark difference than when I last saw most of these people.

I’ll be both working and taking some time off this entire week in SF. Sticking to the theme of kids and old friends, I’ll be trying to see as many folks as possible despite only leaving SF 3 months ago. These west coast trips just aren't going to happen that often anymore with Colin starting to walk and the stress of a long cross-country flight.

I had hoped to spend more time off especially given the time of the year, but it’s a tough fully signing off for many days at a time. Simply put, things have to get done and there’s only so much I can offload.

Meme stocks are here to stay

When the Gamestop and meme stock saga was unfolding in 2021, I had thought that was a moment in time occurrence due to the ZIRP and COVID. People were bored and learned how to buy individual stocks for the first time through apps like Robinhood. They had extra cash to spend after being inside for almost a year and people were ready to gamble.

I was completely wrong that it was a one-time thing. Sitting here today in 2025, I’m reading about how Opendoor stock which was once a penny stock has surged over the last couple of days due to WallStreetBets. Meme coins are also still alive and well with people pumping these tokens still.

I personally don’t participate in any of this, but I have friends who do. The allure and appeal of getting rich quick is outweighing the obvious odds that this won’t work out in their favor. I don’t blame them. Perhaps if it was 10 years ago and I was a bored 25 year old with a lot of time on my hands, I too may be participating in the degenerate behavior.

Afterall, it can be a lot of fun despite perhaps likely being a losing proposition. For now, I’ll save my degen behavior for my maybe once a year trip to the casino with friends.

Finally getting the hang of being a Dad

It’s been 8.5 months since Colin was born and I’m finally feeling like I’m starting to get the hang of this fatherhood thing. The first few months were actually okay for me as my adrenaline powered through. Starting around month 3 or 4, I really started to struggle with the weight of work and personal life on top of Dad duties.

It was a rough few months for me. It was a stressful work situation and we also threw in a cross-country move into the equation. It felt like the excitement of moving back to New York was offset completely by the stress and anxiety of life.

We have now crossed the 2 month mark of being in New York and life is much better. We finally feel settled in and know our way around the city again. I’ve worked a lot on myself personally especially in the last month and I’m starting to feel the benefits of that as well.

It wasn’t rocket science for me, but really basic things. I aimed to get more sleep and ensure that I wasn’t a zombie most days. Part of that was reducing the drinks I had on the weekends as well as the amount of social activities. Doing less was more for me and allowed me to enjoy my days and life more.

I tried to be more present when I was with Colin which included putting away my phone and email and just focused on enjoying playing or taking care of him. I got into a good routine with working out and work. Lastly and maybe most importantly, I changed my mindset on things.

Instead of being anxious about taking Colin places, I embraced it and tried to look forward to things. This will again be tested as we take Colin to Seattle for a wedding this week. There will be a lot of travel and there will be parts that will be stressful, but I’m staying positive and excited that I get to travel with my son.

Being a Dad is an amazing thing and I’m glad I’m back in a place where the pros outweigh the cons by a large margin.

Work flexibility

It’s a lonely Friday in the office this morning. I am one of maybe 5 people including staff on the entire floor. I’m all for working from home and taking early Fridays especially in the summer, but I also can’t help but think how far work culture has come in the last 10 years.

I was a Senior Associate at PwC 10 years ago. We had a great office right by Grand Central. And the assumption was that most people were in the office 5 days a week. At this point, I was 2 years into my career and I was always in the office on Fridays alongside nearly everyone else.

As I got older and more comfortable, I started to earn more flexibility and was able to work from home on Fridays. But it was never a given. I’d always ask my Directors and Partners if they were coming in or not before making the decision to.

I do believe that flexibility and hybrid work is the future. We are currently hiring and the idea is that this will be primarily an in-office role with room for flexibility on days like summer Fridays and when people have to be home for certain reasons. But the standard needs to be set that this is a primarily in-office role and that flexibility is earned, not a right.

Content everywhere all at once

I find myself constantly overwhelmed by the amount of content out there. I have about 10 articles in my email inbox sitting there waiting to be read. I have two tabs on my current personal browser that I want to read. I have a checklist of TV shows and movies that I want to watch in my free time. Between my texts, X and Instagram accounts, I usually have a handful of videos my friends send me that I have to catch-up on.

I simply don’t have enough time to read through everything at this point of my life with work and a kid.

The world is consuming content at an insane rate. And also demanding more of it. Where there’s demand, there will be supply. I wonder at what point are we going to be at where the majority of content out there is created by AI.

Doing enough

It’s been a fun July so far. I’ve been doing a ton of things again on a personal level after a tough couple of months. I had some time off at the beginning of the month for the 4th. We’ve had a trip to visit the grandparents in Baltimore last weekend. And my friend from SF took me to go see the Fallon show on Monday.

We’ll end the month with a trip to Seattle for a wedding starting next week and then a week of remote work in San Francisco to visit family and friends. It feels good to have balance again in my life. Whereas the last couple of months really tilted towards work, this month admittedly is much more on the personal level.

This is a normal thing and I do feel like I deserve to not feel like I’m sprinting 24/7 at work all the time. But at the same time, there is a level of anxiety still that I’m not doing enough at work. It’s a weird feeling that is the result of programming myself to be this way, especially after the market of the last few years.

I always feel like I need to be doing something or else Secfi isn’t going to go well. Of course, that’s fully true. Things are moving along quite nicely at the company and we’re making a lot of progress every day. Deep down I know the most important thing is to relax a bit and make sure I don’t burn myself out. It’s something that I’m working on and will need to continue to work on.

Acqui-hires

There’s a big trend going on right now in tech where the large tech companies are out there effectively doing a ton of "acquihires”. I say that in quotes as this has been the the traditional way of acquiring smaller startups for the talent.

In the past, companies would buy out the entire smaller company usually with stock. It’s usually not the happiest outcome meaning that the product often never got off the ground, but these large tech companies would acquire the IP and all the employees. Yes, sometimes some employees got cut as part of it but at least there would be some conclusion or endgame to that startup.

Nowadays with the regulatory environment, many of these tech companies are changing their methods to bypass those regulations. For example, they’ll acquire a stake of the startup primarily to get access to that startup’s talent pool and IP. The big companies will spin out the top talent of that team.

Unfortunately this often means that the other employees who don’t make that cut are left in a weird situation. Their company is still running and often the IP of that company is being licensed to the big tech company. Meanwhile most of their top talent now works at the larger company. This effectively leaves that small startup continuing to operate but kind of left to dry out there.

Most employees receive common stock and they often do not get a payday out of it. They’re also left running effectively a zombie startup with seemingly little hopes of growing much and getting that big payday.

It’s an interesting and weird trend going on right now with the fight for AI talent.

Mid-summer

We’re in the heat of summer literally and figuratively. I’ve been sweating uncontrollably the last few weeks and have really struggled readjusting to the east coast summers which also feels like a particularly bad one. It’s also the MLB all-star game tomorrow which is dubbed the “mid-summer classic”.

It’s always this time of the year where things get really difficult to grind things out. For the next 6 weeks or so, there will be a ton of people out of office or “working remotely”.

We don’t really have summers in San Francisco so things were a bit different the last few years while living there. But being out here in New York, it’s hard not to notice that things are a bit more quiet in the office. A lot of the locals are gone, but the tourists are out in full force. My meetings are getting pushed back or I’m told that we’ll circle back in August.

For myself, I suppose I should be happy and take advantage of the relative quiet. While things never fully slow down completely for me, it is a great month to relax a bit and take it easy. There’ll be many more months ahead for me to go back into stress mode.

Startup and investor mode

It’s been a great week of meetings and building at Secfi. We kicked off the week with a management team “offsite” and then had some team events. Then we spent the rest of the week doing in-person meetings hashing out some of our plans for the rest of the year and going forward.

Secfi is such a unique business in that I feel like I’m always switching between “fintech startup” and “investor” mode. For better or worse, we are a bit of both.

In some meetings, I have my startup hat on where we’re figuring out different marketing strategies to reach more users, or how to grow a new product line. In the next meeting, perhaps we’re discussing a new company that looks promising.

It’s a lot of fun and I feel fortunate to have the opportunity to have my hand in both. Of course it’s a double edged sword and there are complications as well.

Cost of living tradeoffs

For better or worse, I’ve only lived in the 3 most expensive cities in the US. I grew up in San Francisco, went to school in Seattle, and then moved to New York. After a stint back home in San Francisco, I’m now back in New York (Brooklyn to be specific).

I’m unfortunately no stranger to the high cost of living. As such, I am 35 and have had a pretty good career overall and still don’t own a home. There are times where I talk to friends who lived in lower cost of living cities and are now buying their second homes and I do get envious at times. It’s nice to own.

At the same time, I don’t regret my decision. One of the trade offs for the opportunity to live in New York in your early to mid 20s is that even with a good salary, you’re typically not saving that much money. I’d imagine it’s similar for those who moved to San Francisco after school.

It’s definitely a pay to play world in SF or NY. In order to experience the big city life and all the best food and bars, you need to open up the bank account a bit. Of course, there’s a lot of pros versus the obvious con in that it’s expensive. You can accelerate your career in these cities. You get experiences that others do not as well.

There’s no right or wrong answer and I have friends that are very happy to not be living in NY or SF. But for Sophia and I, it’s been an awesome experience. The house and property can wait a few more years.

Office culture

It’s been a really fun week of work so far. We had the management team in town for an offsite on Monday and Tuesday, and then we went out for drinks and dinner with the broader team in New York.

Personally, this in-person connection is exactly what I’ve been missing the last few years in San Francisco. Being able to connect face to face with your colleagues and get to know each other on a much more personal level is just game changing. Working at a small firm is tough and being around your colleagues live is just simply a lot more fun.

It’s also just a much more efficient way to work. Even in this day and age where everyone is seconds away via Slack or Zoom, there’s just something about being able to turn around to someone on the team and ask a question, or grind through a problem together in-person.

The heat and humidity aside, it’s been a great few months back in New York and I’m excited for the years ahead.

Tokenized stocks

The newest trend in crypto is tokenized stocks. Given everything going on, I have been following from afar but have yet to do a full deep dive into this. All that said, I am very worried at the potential downsides here.

For the most part, it seems that companies are launching tokens to mirror private company shares without actually owning the shares or having rights to them.

One of my fears is that many retail investors will be buying the token thinking they own SpaceX when in reality all they own is just a token. Without anything actually backing the token, they could be completely exposed.

The implications of companies spinning up tokens could also cause private companies to further tighten up restrictions causing a lot of downstream issues. On top of that, I fear that when something inevitably does blow up, it could be a big negative to advance the legitimacy of crypto.

New quarter, same old BS

I’m back at it after taking the last 5 days off. I’m proud of myself for making sure that I truly took the time off and spent nearly no time in front of my laptop. There were a few things that I needed to get done, but for the most part, it was the longest break from work I’ve had this year.

Sophia and I finally had time to ourselves last week to explore New York. It was a nice break from parenting and both of us decided that we really need more time to ourselves away from Colin at times.

We officially kicked off Q3 this morning with the team. It’s the most optimistic start to the quarter in many years. We had a great Q2 and things simply just felt a bit different and more normal. Rather than trying to beat the bear market the last few quarters, the end of Q2 felt that things were starting to normalize. And stability and normalcy is a welcome sight.

Of course, as I get back from lunch I see that Trump is back at it again with his trade war imposing a new tariff on Japan and South Korea who happen to some of our biggest allies and trading partners. Where does this end up and how will it ultimately affect us in the private tech space? Who the hell knows.

The good news is that the team and I feel battle hardened at this point. We’ve been through so damn much over the last 3 years that nothing surprise me anymore and it’s almost busy as usual. Of course, I reserve the right to complain about everything, but at this point, I’m choosing to stay on the optimistic side of things. New quarter, same old BS.

Break time

Starting this afternoon I’ll be off for the rest of the week to unwind and recharge. I’m especially looking forward to these next 2.5 days as Colin will be in daycare. That means that Sophia and I can actually hang out and do some things by ourselves which will be incredibly nice. With both of us working demanding jobs and not having family locally, we don’t really get out much together.

My plan for the next 2.5 days is to simply just enjoy New York. I hope that I can relive some of my younger days when I lived in the city more carefree exploring and just living. We may go check out some museums, eat at some new restaurants, and just generally explore like we’re on vacation.

What I want to make sure we do is definitely not do many errands or work. These days are incredibly important for us both to recharge. It’ll be good to get away from my computer, the news, the markets, etc. and live a little.