Am I a boomer?

I played another 9 holes this morning with an old friend of mine. My swing was atrocious and I seem to have overcorrected my hook and now I’m slicing everything. It was frustrating but I was having a great time catching up with my old buddy Alex on a gorgeous morning to really care too much.

I’m 36 now and most of my friends have kids, and time with friends is incredibly limited. I moved back to New York over a year ago, and I had yet to see Alex which I didn’t feel great about, but with kids and life things are just too busy to hang out with friends every weekend.

On the topic of age, it feels like the new status symbol amongst the youth is having AI agents. I heard on the golf course today that “my tee times are all booked by my agent”. Almost every day, I come across a tweet of someone bragging about their 10-50 agents basically running their lives.

Admittedly, I feel like a bit of a boomer as I have 0 “agents” running my day to day life. Most of my work life right now is relationships and talking to people, and mostly decision making. I use AI as an assistant for most tasks to review, research, or prepare things for me, but I am far from that person that is sitting in a coffee shop while 30 agents do their jobs.

Despite not being to automate perhaps my actual work life, I still would like the thrill of having a so-called agent. It’s probably time that I set-up things the right way and at least give it a shot, even for miniscule tasks like booking a tee time.

AI as my reviewer not associate

I’m doing a fairly brutal (boring) administrative tasks that involves aggregating data from multiple sources and verifying the numbers on a spreadsheet. It’s something that needs to be done as our back-end team is cleaning up our data.

On the surface, this is a great task for AI which is great at searching data sources and pulling that information together. And indeed, it does a very good job of doing that.

The downside? Well it takes forever and won’t always be fully accurate so I have to still check my work. Not to mention of course the token usage.

I started using Claude at the beginning, but I found that I could do it much faster manually and just decided to grind things out for 30-45 minutes while listening to a good podcast. There’s of course probably a better way to do things with AI that’s more accurate and efficient, but at the same time, for a task where accuracy matters a lot, AI is a much better reviewer than preparer.

August golf

I played 9 holes in the morning before work today for the first time in a long-time. First, my golf game is finally getting decent again and I’m much more comfortable over the ball again. That obviously makes things a lot more fun.

Equally as important, it was really nice to get out and do something different in my day to day routine. I’m a creature of habit, and sometimes I fall in the trap of just doing the same thing every day. Wake-up, take Colin to daycare, workout, work, cook dinner, watch TV, and sleep. Even as new parents, we need some excitement in our lives and an occasional round of golf on a Wednesday was great.

On the work front, I was reading that OpenAI only grew 18% last quarter compared to Anthropic more than doubling their revenue. While OpenAI focused on getting to the consumers and chasing everything such as video production, Anthropic just stayed focuses on getting to all businesses. They’re paying for that strategic decision today as Altman continues to reshuffle leadership amidst an exodus of top talent.

It’ll be interesting to see where things go from here. Does Anthropic continue their dominance in the world or do things level out as the cost of AI continues to rise? It feels like it’s all rainbows ahead for Anthropic, but unfortunately that’s not how the business world works and the road likely is a bit bumpier than most optimistic people think.

Sticking to the plan

When we made the decision to move to New York last year, I put together a high level financial plan for us. The idea was that we would go to New York, enjoy our time, but at the same time look to aggressively save. The idea was that in 3-5 years time, we would likely move back to San Francisco and look to buy a house. The plan was to start looking perhaps next year casually and hopefully find a place to settle the family into long-term.

So far that plan has been great for us as my wife and I have been consistently putting cash into the market while still largely having fun being new parents.

The big curveball that was thrown into my said financial plan was that I was not expecting San Francisco’s housing cost to rise over 50% in this short time. Thank the AI boom for houses going for 50-100% over market price right now. This obviously makes buying a house at the moment nearly unattainable.

Knowing how markets and booms work, I’m mostly keeping a level head about this as things likely will settle and come back down to earth. At the same time, I’d be lying if this didn’t give me a bit of angst as it’s currently just somewhere between unattainable and non-smart financially for us to buy right now in SF where I grew up.

Stresses aside, I’ve been telling myself to just stick to the plan. Putting money to work in the market is never a bad thing, and owning a house isn’t the end all be all. We’re all on different timelines financially, and my plan is different than others. Furthermore, situations like these do create opportunities and it’s good to be patient.

Safety and abuse

I had a great low-key weekend with lots of sleep and recovery. It was admittedly a bit “boring” where most of my weekend was mostly just being a Dad or running errands. For better or worse, at this point of my life, you either choose boring and relaxing so you can feel rejuvenated and great after the weekend or choose a more fun weekend where recovery suffers.

On another note, I was reading about the increased public scrutiny against Flock cameras. There’s a lot of concern about privacy and police misuse of the cameras. Most of which I completely understand. There’s a reported number of abuse of the technology where police officers are using it to track down people for personal use. That is indeed alarming.

On the flip side, I also know how powerful the technology can be to deterring crime. In San Francisco where I grew up, crime is now down especially in car smash and grabs. For some years during the after the pandemic, San Francisco was the hot bed for smash and grab theft. It was brutal walking the streets seeing multiple car windows smashed. It still happens, but I read that it’s been down almost 10 fold since Flock cameras came on.

Overall, I believe the bigger issue at hand is the mistrust of police and government in general. Yes, it’s hard for me to still be a staunch supporter if our police is going to abuse the technology to track ex-partners down. There is a much larger systematic problem here and that is that there are a lot of bad cops and abuse in the system. I do believe that we need to address the root cause of the problem here, not blame the technology.

Recharging

I’m loving being back in New York in this slower time period of the year. With the travel hell last week, getting back to a routine, good sleep, and hard workouts has done wonders for me. This week and the next couple is all about aiming to catch-up and get ahead of work, while balancing just enjoying life a bit more.

Most of our team is on vacation in August. And our partners/clients also seem to be taking time off. My inbox may be at an all-time low this week for the year. These times don’t happen so it’s good that I take advantage and recharge my batteries now.

It’s a much needed break after what felt like 7 months of just craze. I expect some more work from home days and perhaps some early rounds of golf. I hope to get my golf game back to a decent spot as I was shaky during yesterday’s 9 hole outing. I also hope to enjoy New York a lot more with Sophia. We haven’t had too many chances to go out like we used to when we last lived in New York so now is as good as time as ever to go enjoy the city.

The start of the return to normalcy?

One of the trends the last few weeks that I’ve been monitoring is the demand in the private markets for the top tier names. The poster child of this in the last 6 months was of course Anthropic.

By no means am I saying that this is the top or the market will drop, but there seems to be indicators that the interest level has been declining so far in Q3.

For one, the bids in the private market platforms have sharply declined over the last twelve months. It used to be a wall of bids of individuals looking to get into Anthropic, but that has seemed to reverse so far with a lot more offers of stakes in SPVs. Of course a part of that may be Anthropic clamping down on SPVs, but I for one do not believe that the public scrutiny would stop buyers.

Also, very anecdotal evidence, but the inbound outreach that I received on LinkedIn and email for access to Anthropic seems to have sharply dropped. It used to be that every other day I had cold outreach for individuals looking to buy Anthropic and asking me to source it. For what it’s worth, I haven’t had one inbound in the last month.

This all could just be a product of the the summer months of August where investors are known to take a lot of vacation. At the same time, it’s also hard to ignore that there could be something more to it. I still believe in Anthropic, but perhaps this is the start of the valuations coming slightly back down to earth as competition heats up and perhaps having the best model does not declare you the winner in the space anymore.

Recapping Black Hat

I’m feeling like myself again and can finally put that week of travel hell behind me. As a new parent, my normal baseline is to usually be tired but the combination of work, social events, multiple city travel, and especially the delays really put me in a bad spot the last couple of days. Sleep deprivation is a real thing and needless to say I’m glad to have positivity back in my brain.

It’s the middle of August and it feels like everyone is on vacation but a handful of us. I am jealous in many ways, but I’m also happy to be here to catch-up on things and just enjoy being a Dad for a few weeks.

On the work front, it was my first time at the Black Hat conference last week. As a non-technical person at a cybersecurity conference, I did find it interesting to learn where the industry is headed. To no one’s surprise, the big topic was AI and agents. It seemed like every company was out there touting their new products for agents and marketing budgets were all focused there.

Like most of these industry conferences, I did feel like the most productive use of my time was scheduling meetings with my network ahead of time. Secondly, it was going to the small presentations and meeting executives at companies we’re following. The business hall was interesting to learn, but I’m not a CSO looking to buy a solution so it was always a bit awkward asking for a demo from a BDR there.

The focus of these conferences is to sell product and meeting investors is almost always secondary. All that said, it’s a great meeting place for the network so it’s always a bit of a toss-up whether the conference is worth going to or not. Going forward, we’ll definitely need to figure out a more defined plan on what we want to accomplish and schedule more meetings ahead of time.

No good deed goes unpunished

My flight back to New York on Saturday capped out a very difficult travel week. My flight back to San Francisco from Vegas after the conference got delayed and I didn’t get back to bed until late on Thursday. I spent most of the day with family, and then saw some friends on Friday night.

Unfortunately, the travel exhaustion caught up with me on Saturday which ended up being a rough day as I was traveling back to New York. After almost 4 hour delay, I didn’t get home until around 1:30am. It took me longer to fall asleep and I probably slept perhaps 4 hours before having to get up and be a parent. I was absolutely a shell of a human yesterday and I’m still feeling a bit of the effects as I write this Monday morning.

Perhaps the most frustrating part about the whole ordeal was that I really did aim to prioritize rest and recovery on this trip. I am not someone who can sleep everywhere and my philosophy in the past was always to power through. I did not want to feel awful coming home after a long week, so I did my best to get to bed early, exercise, and keep the drinks low.

Of course, no good deed goes unpunished as flight delays threw a wrench in all my plans. These situations are incredibly frustrating and stressful. There’s the physical toll on my body which I can overcome, but the mental aspect has always been much harder for me. I feel like a shell of myself and happiness is much harder to come by when I’m running on fumes and sleep deprived.

These temporary physiological dips are not fun, and my brain needs time to catch-up. Despite good sleep last night, it’ll likely take another night of good rest to start to feel normal again. Until then, I’ve been doing my best to stay positive and realize that this will all pass soon enough.

SpaceX lock-up expiration

It was a good and fruitful Black Hat conference and overall I had a good time in Vegas these past couple of days. These conferences are always exhausting and yesterday was no exception. Even after getting pretty good rest Tuesday night, I was running on fumes most of Wednesday and relying on caffeine to get me through. The earlier week travel and craze definitely contributed.

I suppose I’m officially old now as I was in bed before 9pm last night. We had a nice dinner and I had a thought of perhaps gambling a bit more after, but ultimately I decided to prioritize recovery. I’m thanking myself today as I look to close out the conference and head back to San Francisco.

The big news of the day is the SpaceX lock-up expiration. We have never seen anything to this scale before. The available shares to trade has more than doubled today as the first lock-up expired. The stock has taken a dip in the last weeks with the expectation of the expiration. But it does appear to be holding fairly steady today as investors had planned around this for awhile.

This is going to be a story for the coming months as more lock-ups expire with a very staggered approach. Given the scale and size of the SpaceX IPO, we’re going to have billions of shares of SpaceX unlock and it’s going to be interesting to watch what happens with the price.

Vegas Again

I’m in Vegas for the Black Hat conference. Vegas is always a bit of a trip for me every time I come here. On one hand, I have to appreciate everything built here. It’s vast and gigantic adult playground with genuinely impressive buildings. I walk around and go, damn this is crazy. And I always have fun here. The food is good. I like to gamble a bit. And there’s no shortage of things to do.

On the other hand, it is a melting pot of craze in lots of bad ways. It’s not my vibe generally at this point of my life and that’s okay. I’m here for work and will sprinkle some fun in there, so that’s where I’ll be focusing this time around.

Like any major Vegas conference, it’s going to be hectic and extra in both great ways and bad. I’m always interested to see how some companies are burning VC money in the exhibition hall with the structures they are building. The ROI of these conferences have to be positive, right? I’d be curious to see a detailed analysis for a large subset of companies and how much new business actually get drummed up.

The return of SF

I had a brutal travel day yesterday getting to San Francisco. I was worried I would be delayed given the storms, but we departed on time and thought we were in the clear. Right before take-off, we got grounded and spent the next hour and half on the tarmac. Luckily, we were cleared for take-off again but then ran into an engine issue and had to switch planes.

I eventually got to San Francisco about 6 hours late and unfortunately condensed my busy travel schedule this week. I had to cancel some meetings yesterday and basically just got to my Dad’s house, ate dinner, and went to sleep. Thus is life and at the end of the day, it could have been a whole lot worse.

It’s only about 15 months since I left San Francisco. After walking around downtown today for a few minutes, I could instantly tell that things are starting to come back. There are a ton of new restaurants open in the area. The area was a lot more crowded than I saw when I left a little over a year ago. Even my old coworking space is much more crowded to the point where there was only one conference room open to take my call.

It’s obviously a much different vibe than New York here, but it doesn’t take long to realize that the city is back and moving in the right direction. Of course the AI boom is a big part of it and it was interesting to see all these new companies that moved into my coworking space in the last year.

Lack of IPOs

Colin has been in full toddler mode this week. We were warned of this phase but now that it’s hitting, it’s been interesting to say the least. One morning he can wake up and be the sweetest funniest boy. The next morning he wakes up and will be cranky nearly all morning. His preferences for things and demands for his choices now is something that we’re also dealing with head on. It’s a bit exhausting, but I suppose every stage has it’s pros and cons.

On the work front, I’ve been wondering what will need to change for companies to actually willingly go public.

With billions of dollars looking to get access to the private markets and the regulatory strain of being a public company, many founders and executives are just very content staying private. And I can’t blame them.

The stress of quarterly reporting and the public scrutiny behind being a public company is very real. The President has proposed moving to bi-annual reporting which could help the case going forward and easing the requirements to go public.

But perhaps equally as important is the fact that there is just a ton of money in the private markets now. VC and PE firms are able to provide liquidity at the company and personal level for companies that could be public. Yes, the cost is higher than if they were a public company but there is a big tradeoff and right now, for most companies, the pros of staying private are outweighing the cons.

It’s a trend that has been happening the last 20 years and I don’t see it stopping anytime soon unless there’s some changes on the macro environment and/or regulatory.

Getting back into golf

Last week, I joined Gowanus Golf Club which is a simulator “club” based in Brooklyn. I had wanted to get back to golf as my primary hobby again. I had mostly hung up the clubs once Colin was born and had only gotten out to a course a handful of times since.

As a busy Dad trying to balance being the best Dad possible with work demands, it was easy to put aside my hobbies in favor of more time for work and Colin. With these last 6 months, I did feel that I had a void in my life… something outside of work that I was personally invested in. In an interesting way, that void led to work becoming more of my hobby. I would fill the short empty times on weekends catching up on email or reading about work related things.

For that reason, I decided to try to get back into golf. I used to obsess about my swing and scores in a constant battle with myself to try to get better. It was time consuming and that’s probably why I put things aside, but in actuality, it was a very healthy hobby and fueled the competitive fire in me.

I obviously won’t have nearly as much time to think about swing like I did last time. I’ll be lucky to get out to the course once a month. But there’s a healthy balance that’s possible here and it’ll make me happier.

First thing for me is using my swing coach (Claude) to make a plan to get better. After a long time off, it’s going to be great to get back to the fundamentals. I never had a long term switch coach before but with AI where it’s at, I’m excited to leverage it to improve my game.

Training

Things are quieter right now, but I feel like my list of minor small things to tackle just keeps growing. Review this copy, review this content, update this deck, etc. The work is usually a bit more tiring than my usual of just closing deals. The context switching every 10-30 minutes wears me out a bit.

On top of that, it always feels like my checklist gets bigger by the day and it’s always like whack-a-mole. There’s really only a couple ways to fix this in the future.

First, look to leverage AI to automate some of these tasks. Unfortunately, it can only go so far as a lot of these items are judgement calls where obviously a human like myself needs to make. Nevertheless, there are definitely some tasks that are worth exploring AI to take over.

Second and most important will be training new staff to take over and delegate tasks to. We’ve got a lot of new young talent that is joining the team and I’m incredibly excited to get them onboard. It’s going to be a lot more work up front, but what we need right now is an infusion of hungry talent to come in and help take us to the next level. That’ll be one of my biggest priorities to close out the year.

Quiet period

SpaceX stock continues it’s dip and the media is having a heyday with it. For me personally, I did not want to own SpaceX at anywhere near the IPO price. But I also know that there’s a lot of hoopla with the media as politics has become involved in one of the objectively most impressive American companies. It also does not help that it’s the middle of summer and not too much else to talk about.

New York and the broader finance/tech world seems very quiet right now. Things always slow down this time of the year, but it does feel like people are taking more extended vacations. I spoke to an exec at one of companies we work with, and the message from their executive team was to take vacation this summer as they think things will heat up in the fall.

I’m welcoming the quieter period and plan to fully take advantage.

Open-weight pledge

It was a perfect summer weekend in New York. It was sunny, 80ish degrees, and a slight breeze. Sophia and I got a baby sitter for Friday night and had drinks and dinner outside. On Saturday, we had friends over for drinks and the pool, and we spent Sunday mostly just hanging out in the pool as well. It was a perfect weekend in terms of a balance of having fun and not overdoing it.

Given the time of the year and prioritizing my personal life a bit, it’s been hard to keep up with the news front, as little as it may be. But it seemed like the big news topic of the weekend was a lot of companies signing on to the open-weight model pledge.

On the surface, it’s hard to disagree with the concept that restricting open-weight AI models could reduce competition and push innovation abroad. Overall, it should in theory be better for consumers as businesses can use cheaper open-source models rather than be tied to a company like Anthropic.

But the topic is a lot more complicated and I understand why Anthropic has not yet signed on to it yet. For one, they may be the biggest loser in this as these open-source models will train on Anthropic’s proprietary models and inherently, as the current front-runner out of the frontier labs, it could jeopardize their top spot and valuation. It’s a tough position to be in right.

This will likely be a hot topic in the AI world for awhile now as everyone is looking to get most cost-efficient models to do their work. For the majority of companies and Americans, the models have gotten to the a point where a marginal increase in performance is likely not worth the cost and the focus is much more on the cost.

Conference season

The conference season is about to start once summer ends and I’m excited to get on the road again. These conferences are a nice change of pace to the day to day grind.

I get to learn from industry leaders and see what’s going on in the world. More importantly, I get to meet a ton of builders and leaders. And catch-up with a lot of our friends and partners which is always a fun time.

As always, I focus a lot on ROI and making sure that I get as much out of these conferences as possible. For me, it’s no longer like the old days when I could go to every conference and travel whenever.

Each trip means my wife is solo parenting while also working which isn’t easy. Time spent away from Colin is also tough. For that reason, I’ve had to be very selective and pick and choose the business travel I get to do.

That means making the best use of my 2-3 days at these conferences prioritizing the biggest meetings, dialing down the “fun” and social events a bit, and ensuring that I come back energized to be a parent.

Summer and fall of golf

I decided yesterday that this is going to be the summer and fall of golf for myself. With only one kid who is getting close to 2, things will not get any easier for me to get out there and work on my game.

I miss having a hobby to obsess over. It’s been a gap that’s been missing in my life the last year or so since I moved to New York. Despite the frustrations, there’s a competitive aspect of golf that I love. The idea of continuous improvement and making strides, and then watching the practice play out during a round.

Unfortunately, I won’t have a ton of free time to practice and play, but there’s not going to be an easier time so I’m hoping I’m able to carve out some weekday mornings or late afternoons to make time. First up is figuring out how to get my swing into a stable place again.

Balance during the slow periods

With everything slowing down a bit as people take time off in the summer, it’s been a nice week to catch-up on everything both personally and workwise.

My inbox is getting cleared out. My admin tasks that always get pushed off like cleaning up our CRM is finally get tackled. My non-urgent projects are finally getting started. And probably most fun, my creative and learning work can begin again.

The big issue for me right now is finding motivation. With a light office and great weather, it’s very easy to just slack off. A long lunch somewhere in the city sounds pretty damn nice right now. Especially after a hectic couple of months.

All that said, I find these times incredibly important to keep moving the ball forward. This is valuable “dead” time that allows me to get ahead of the game and prepare for a bit more hectic time period after Labor Day. More importantly, it’s quality time for me personally to learn and work on projects that can help me grow such as getting more AI native.

There’s a balance between making sure I get time off to relax and enjoy the end of summer, but staying productive. Finding that balance is key.