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.

Spontaneity

It was an interesting end of the week and weekend. With the end of the quarter, I had hoped that I could take things easy and unwind a bit. It was indeed a fun few days, but anything but relaxing.

It was a heat wave in New York with temperatures reaching over 100 degrees at points which made things even crazier. On Thursday morning, my building’s power went off and Colin seemed to have caught a stomach bug at daycare. That alone was a stressful situation, but we were supposed to leave the next morning to visit our friends in Virginia for the long weekend.

We had a decision the next morning on a go/no-go with Colin seemingly better and our A/C in our apartment still off. I was candidly worried and thought it was a force, but Sophia ultimately won out and we started to make the drive down.

We made our first stop once we got to Maryland for breakfast, and the minute we took Colin out of the car seat, we knew that he was off and it would be irresponsible for us to continue onto our friends and spread the stomach bug.

I’m proud of the way Sophia and I handled the situation. In perhaps earlier days of our parenting journey, I or we may have panicked and stressed each other out. But we both decided to make the best out of it. Instead of turning around, we found a park and figured out our game plan. After quick deliberation, we decided to go to Annapolis for the day and night and see how Colin was the next day.

We turned a disastrous situation into what ended up being a really fun weekend. We booked a nice hotel in Annapolis and ate some great seafood for lunch and dinner, and also squeezed a much needed mid-day nap. The next day, we continued to our friends place and had a great couple of days with them.

While reflecting back, I realized just how much I was missing those spontaneous moments or events. Everything in my life is planned down to almost the minute nowadays. My workday calendar is packed back to back. Colin’s nap and sleep schedule gives us structure when we’re not at work.

For once, it was really fun to just go off script and do something different. Colin is 20 months now and he’s fine and happy to be along for the ride. As we head into the middle of summer, I’m hoping for a lot more of these spontaneous moments.

America 250

Apparently I’ve decided to bring all the extreme weather to New York as it’s supposed to be the hottest in over 10 years in the next few days. As much as I don’t like the extreme cold, I absolutely hate the heat and humidity so this next week is going to be a brutal and sweaty time for me.

All that said, I am excited for the quarter to be over and things to slow down a bit. I’m taking the family to Virginia to visit friends for July 4th. Luckily they have a nice big house with great AC where I likely will be hiding indoors most of the time.

I’m always a fan of July 4th given the summer aspect, but this year feels especially unique given the 250th celebration of the USA. I think a lot of Americans feel down about the country and where we are headed right now. My stance has always to stay on the optimistic side of things and I am glad to be alive for our 250th year as a country.

We’re imperfect as a country like every country, but I still firmly believe that this is the greatest country in the world and I feel fortunate to have been born here. In a funny way, the World Cup event has really shined a positive light on America recently that has made me feel a lot better about things.

A lot of the world has explored America for the first time and has been fascinated by the things that we take for granted in this country. While some things are probably less glamorous, see gigantic soda cups, I’ve loved how visitors are finding joy in simple things such as our gorgeous scenery, vast road network, and barbeque.

It’s yet another reminder that life is good and we need to take time to appreciate life a bit more. We have it really good here in America despite all our flaws.

Balance

I checked another state of my list as we went to West Virginia for a family wedding. It is a gorgeous place with lots of greenery and mountains, and I enjoyed my time there. It was really special watching Colin play with Sophia’s family members and quite frankly, something that we won’t be able to do too often.

There’s always give or take though. We left West Virginia at 10am yesterday and got home past 6pm after a stop in Baltimore. These trips are absolutely exhausting especially on the way back after spending the whole day partying for the wedding. I struggled out of bed this morning but felt a lot better after my morning run.

It’s always a balance between having fun and living life, and also feeling great the next day. It feels like the more “fun” you have nowadays just drains the tank the following day or even two.

These events start to decrease as we get older and I’m well aware of it. I’m only getting older and it won’t be long until we start saying no to more social events in light of rest and also to prioritize Colin. For that reason, these weekends are well worth it still even despite the trade-offs of feeling tired for a couple days.

Learning from AI

AI has changed the way I work on many levels. One of the biggest benefits at work right now is that I have my own lawyer. One that cost much less than calling one of our lawyers and also works a lot faster. It won’t replace lawyers anytime soon, but it helps flag any relevant issues with the docs I see on a day to day basis and drafts most of our basic legal language nowadays. Legal works used to be incredibly draining for me, and it’s much more manageable.

A byproduct of working with my AI lawyer is that I’ve learned a ton as well which is likely the biggest benefit for my career. I have the LLM explain concepts to me that were previously foreign so I know for next time. My legal skills have improved significantly over the last few years.

On a personal front, I’ve used ChatGPT for most of my personal life. I learn more about nutrition and food over the last year than I perhaps have in my 30+ years prior. My Whoop AI has become my personal trainer to get me more fit but also feeling better on a day to day basis.

AI is a wonderful thing for people who are interested in learning. For me, I need to know why running in Zone 2 for the majority of my runs is better for my aerobic health than sending it full go. Of course, many are more interested in the output rather than the process, and I do believe they are short changing themselves and their career and personal growth.

Dog days of summer

Things are shaping up nicely for us as we wrap up the quarter. There won’t be a hectic rush to wrap things up in the next week which is great. Most quarters for some reason just end up being a bit crazy at the end with people waiting last minute.

The end of Q2 especially with the July 4th holiday is a nice one for all of us to unwind a bit after bust first half of the year. So far things are shaping up that we’ll all be able to take some time off as we had planned and I’m really looking forward to it.

All that said, we’ve got a lot of “debt” built up over the last couple quarters that we’ll need to focus on in July. Lots of clean-up work and things that need to get done in order for the second half to go well. As we head into the dog days of summer, it’s important that we make sure to keep pushing these items forward while also making sure that we all get some rest.

Sunsetting of the DAOs and NFTs

Back in 2021, I started to play around with NFTs and DAOs. It was a crazy bubble and everyone knew it, but it also brought me back to the days of IRC and gaming. The online communities being created was a ton of fun to participate in.

I joined a golf club DAO, a sports gambling DAO, a gaming platform, and a couple other just random communities. You basically needed to buy a NFT to get access to these communities, and I shifted some of my crypto gains for play money to participate.

It was always a mixed bag. For most, it felt like speculation was the #1 reason they were there which is natural in a crazy market like that. I had no expectation of making money from these NFTs so things worked out rather nicely for me. But I was able to meet some cool people.

I golfed with a group of folks from LinksDAO and attended a few events. I still talk to some of them every now and then. That DAO eventually did succeed in buying a golf course in Scotland and is still running despite things slowing down significantly.

Most of the other projects I’m part of does seem like they are wrapping up and closing down. It was a fun run while it lasted, but most of these communities were built on the fact that the NFT prices would go up. It’s impossible to build a real community when all you can offer is an increase in value.

It’s the end of an era of these crypto projects. But I’ll probably pick a couple to stay involved with. It was a fun period especially when the world was still coming out of lockdown.

Grateful Monday

There’s a lot of miserable people in New York. This morning I had a grumpy guy push my backpack aside with a swipe as I waited behind a Dad and his kids trying to get through the turnstile. The train was still minutes away and there was zero reason to get agitated or frustrated.

I really try to my best to not let these things impact me. I had to catch myself this morning to not say something to the guy. Misery loves company, and I have no reason to ruin my morning. Life isn’t perfect for me, but life is really good. After this amazing Father’s Day weekend, I’m feeling especially grateful for everything.

I had an incredible Friday “day-off”. With Sophia back in town, she let me go out and spend some time by myself. After a few hours of morning work, I went to to get a massage to relax. And then got a nice sushi lunch by myself. I met up with some friends at a bar for the US Men’s National Team game and had a few rounds with the guys.

On Saturday, we got a baby sitter and went to celebrate our friends’ baby shower. We don’t get to go out much, and it was again really nice being at a bar with friends just socializing. Even better, we were in bed by 10:30 and it made Sunday a bit better.

On Sunday, I got to celebrate Father’s Day by not doing too much but spending time with Colin and Sophia. I was a bit exhausted from the prior two nights, but just relaxing and watching Colin run around and live his best life was a special core memory for me. He’s at such a fun age where he’s now seeking me out and looking to play with me all the time.

Parenthood is exhausting, but every day is so incredibly special if you take the time to sit back and embrace the small moments. Core to being able to enjoy those moments is definitely being a better mind space. My sleep, rest, and health have all significantly improved in the last 6 months that I’ve prioritized it. That’s allowed me to be a better father and husband.

I’m not one for holidays and Father’s Day always felt like a bit of a fabricated and commercial one. With that said, it was a really good day to sit down and celebrate Colin, be proud of how far I’ve come as a parent in the last year, and also remind myself how grateful I should be for the life I have right now.