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.

Paralysis by options

Sophia and I have been trying to get to regular date nights every other week or so. It’s an endeavor every time as we have to figure out a date, find a baby sitter that works, and perhaps the hardest thing… pick the restaurant. It’s a blessing to be in New York with all these food options. A lot of the world’s best restaurants are here and there’s not a cuisine you can’t get in New York. The downside is that I get severe fomo especially now that we have a kid.

Sophia and I get out if we’re lucky twice a month together so we always want to try to maximize our time. That means always trying to book the best restaurants. Sometimes that doesn’t happen and we lose excitement by suggesting some place very damn good but maybe not high on our current list.

Every time we go through this process, we usually take multiple nights to figure things out and go back and forth. It’s a painful process and kind of a sad one to be frank, but it’s a real human thing and we aren’t the only ones who do the same thing.

When I think about this in the business sense — sometimes having too many options and offerings just leads to someone getting overwhelmed and just deciding to do nothing. Simplicity is still king and having one perfect solution beats having 5 good solutions. People naturally will always try to optimize and especially in complex financial situations, sometimes it’s best if you pick the best solution for them.

Summer breather

The event of summer is now over with Spain winning the World Cup and things are calm and quiet. It’s the end of July and as we head into August, everything seems to be slowing down. My email inbox is abnormally quiet for a Monday morning. A lot of the team is heading into the peak of their summer travel. The office is going to be very quiet for the next 6-7 weeks.

I’m personally welcoming the change. It was a crazy 6 months or so to start the year. Business is going so well that we haven’t had much time to breathe. These next few weeks will give us a much needed breather across the entire company.

For me personally, I’m excited to be home for 2 weeks and I’m looking forward to calm time at home. Sophia and I have a few date nights lined up so we can enjoy New York over the next couple of weekends. I hope to see some friends and just chill.

In a job where everything feels crazy always, a few weeks of slow and easy is exciting.

Office culture

It’s Friday in the middle of summer and most of the coworking space is empty except our office. It’s a great thing to see when the entire team knows that there’s a mountain of work to get through and we all come together to collectively grind in the office together.

Since moving to New York last year at this time, one of the top priorities is making sure we set a good office culture for the company that we wanted to be in the future. We work together as a team and we get shit done as a team. As someone with a sports background, it’s always how I’ve run my team and how we’ve built the culture out in the New York office.

Working as a team means putting aside individual accolades to a certain degree. It means that we don’t let each other down when we’re dependent on each other. And it means we celebrate winning as a team. As always, culture is how you act not what you say, and that’s been an emphasis for me to lead by example.

After a year, I’m proud of the culture we set and we have the right base culture to expand and grow the team.

Post vacation thoughts

I’m back in the office today after spending almost the last week in Mexico City. I was happy to be home yesterday and get back to work. I always felt a vacation did it’s job when I’m ready to go back to work afterwards and that’s how I felt this morning. For the first time in awhile, it was not a drag to turn on my laptop in the morning and get started with my day.

Mexico City is an amazing place. Great bars, restaurants, and people. The vibes all-around were great throughout the week. I would have loved to spend extended time in Mexico City at some prior to having Colin. It felt like the beauty of the city was mostly built around just relaxing with a coffee and a laptop in one of the many outdoor sidewalk cafes. I can see why so many people moved to Mexico City during the pandemic.

For Sophia and myself, we did more with Colin than we have really in any previous vacation. We sat down for lunch and dinner every day. We stretched his bed time. We went on a tour to the pyramids even. All things considered, he did great and most of my fears of having a crazy toddler were unfounded.

It’s great that he’s at the age where he can actually go out and do more. With a kid though, there’s another side of it in that it’s hard for him to sit down for an extended period and he now wants to be able to walk everywhere. Grabbing a drink at a restaurant is a difficult task as one of us is likely chasing him around the block at some point. With all the amazing bars in Mexico City, I had a ton of FOMO.

My Dad also joined us on the trip. It was really nice seeing him and he seems to have taken a liking to Colin. It was the first time in my life that I felt that he was old though. He turns 70 later this year and while he’s still active and healthy, he felt much more like a “Grandpa” than my Dad. He’s no longer young and he’s starting to have hearing and memory issues. The inevitability of our parents getting older is here and it’s a scary thought.

On the work front, I’m planning on spending the rest of the week just getting caught up. I didn’t get the chance to do a clean-up of the last quarter and I look forward to getting to a clean slate starting on Monday.

I largely stayed away from watching the markets but it appears that SpaceX stock has dropped below the IPO price for the first time. Naturally, the media is having a good time reporting on the stocks drop which feels sensational at this point. We’ll see where it ends up in a few months and whether it has any impact on Anthropic going public.

Mexico City 2026

We’re flying back to New York tomorrow after a family trip to Mexico City. We met my sister here on Thursday and then my Dad, stepmom, and half-sister came on Saturday. I honestly don’t think we’ve ever taken a family vacation with all of us. My half-sister is 15 so she’s much younger and they did their own thing when they were younger.

Being on a family vacation isn’t the easiest thing in the world. The extra hands to help with Colin is nice, but my family isn’t one to do the heavy lifting or really much of any lifting for that matter. All that said, we’re all getting older and I need to remember that these moments are special and I’m going to wish we could do more of these down the road.

In yet another vacation with a kid, there has been a bit of FOMO especially as Mexico City is just an amazing place with lots of great bars and restaurants that are just not conducive for sitting down with a 20 month old. I’ve still had a great time though and it’s been fun exploring the city.

We’ve made a lot of memories with Colin and my family got to spend time with him. He’s no longer a baby and he’s a full on toddler with opinions. Mine and no are some of his favorite words now which makes things more difficult. But he’s also finally at the age where we can play together and it’s been incredibly fun as well.

I’ve always said a vacation feels proper when I’m ready to go home and I’m excited to get back to New York tomorrow. A few weekends at home after being gone the last 3 is what is needed.

USMNT and Pressure

I was incredibly excited for the USMNT game last night versus Belgium in the round of 16. We had the opportunity to get to the quarterfinals in a home World Cup in a soccer crazed city of Seattle right after celebrating our 250th anniversary on the 4th of July. We had played great the last 4 games and Belgium was an aging team that wasn’t the same.

It had all the makings of a magical evening. Then the game began and the team froze under the pressure. Disappointed is one of many words that comes to mind watching the game yesterday. Not only did we lose, but we were utterly dismantled.

There were not a ton of expectations for the team to get past the quarterfinals, but getting there would show meaningful progress that we may be over the hump and one of the best teams in the field. I still do believe that the team has what it takes to compete and beat Belgium, but it was evident to me that the pressure just simply got to them.

In the first 4 games, we saw a team that was free flowing and playing loose and having fun. Last night, we saw a team who came in playing scared and afraid to make mistakes. Credit to Belgium for also playing against our strengths well, but just looking at the way most of our players played yesterday was just awful to watch.

I have never been in any situation where the pressure is even in the same stratosphere for what the team went through last night. But I do know how much pressure can impact performance. Often I’m able to channel that pressure and stress into something great, but sometimes the pressure gets to you and you can crumble.

I have no insight into the practices or what was said or done over the last week since the last game. But perhaps the hype and enthusiasm for the team from celebrities, politicians, etc. was just too much for them.