It's good to be home

It was a fun but exhausting three and half days in Vegas for Money2020. A conference came and went, and I came away from the week absolutely spent and ready for recovery.

Part of that is the nature of Las Vegas. There’s always something about the place where I feel like I need to hop into a steam room and go through a detox for a week afterwards. The constant lights and feeling of darkness always puts me in an interesting mental headspace and it’s always hard for me to get into a routine when I’m there.

The other part is that I always bite off more than I can handle and I need to be smarter next time. Flying in Sunday morning means an early wake-up Saturday so I landed tired. I had planned to take it easy, but knowing where I’m at, I just need to accept that it’s not very realistic given the events and that the reason I’m there is to socialize.

Three nights in Vegas is one too many and I probably just need to accept things and fly out later or leave earlier to save myself a bit. Between all the events and dinners combined with the jet lag, it’s almost always impossible to get to bed early and actually feel rested. Two nights of good fun is plenty.

Lastly, there’s a mental block that I’ve been chasing on my health and recovery that I just need to get over at times. Nearly everyone on my flight home looked exhausted and that’s just the nature of conferences. You spend all day and evening walking around, socializing, and having fun. Not many people can feel amazing after that.

Money2020

I had a lot of fun last night as hosted a small happy hour at Money2020 for the 49er game. We had a pretty good turnout despite doing limited advertising and more importantly, we got to catch up with old friends and clients.

After last night, I’ve realized that we need to be doing a lot more of these events than we have in the past. It’s just great to be able to meet a lot of our partners in-person and really get to bond over some drinks and some football.

I had a lot of fun despite running on fumes and was able to get to bed at a decent time. I decided to let the young kids have fun at the 50Cent concert and went back to my room after a later dinner.

I feel a lot more energized this morning and even went on a quick 25 minute jog to get some endorphins going. But I am definitely tired and excited to get back home in my own bed tomorrow night.

For now, we have a full day of meetings sprinkled with some fun in between. Tuesday is historically a very fun day for Money2020 as people wrap up work and start to unwind a bit. Despite a bit of hesitation, I’m really glad I went to the event this year and I’m pumped for the day ahead.

Oh Vegas

I got into Vegas yesterday for Money2020. I spent the afternoon taking it easy, catching up on work, and just relaxing for the hectic few days ahead. I had fully planned to go to dinner with the team and be in bed early, but a couple close friends of mine were in town and hosting an event, so I decided to extend my night a bit and hang out.

I was half asleep when I got back to my room at 11pm. I have no regrets, but I could have used an extra couple hours of sleep as my jet lag got me up at 5am. Vegas has a funny way of doing this to me and seeing old friends in FinTech wanting to hang out is always a recipe for later nights.

On Money2020, I had thought the conference had gone slightly downhill over the last few years as less investors and companies seem to be participating. But I’ve been pleasantly surprised by everything so far. FinTech may be down in general, but the people here building do not seem to mind the outside noise.

I’ve had a lot of fun since being here. Seeing my old FinTech crew that I met 7+ years ago when I first got started in FinTech has me feeling a lot of nostalgia. Of course, we’re all a bit older now and the partying has subsided quite greatly. I have some members of my team who are here that can carry the torch forward.

For today, I plan on seeing more friends and partners. Then we have a Secfi happy hour for the 49er game which will be fun. Luckily, the game should be over by 8pm or so and I’ll likely make a beeline for my bedroom after a long day.

How do companies price in agents?

I have Muse checking in weekly on flights for me back home for Christmas. I can tell you that I’m not the only one doing this. While the ease of having someone check the flights and try to find the best price is as easy as it’s ever been, I’m not so sure this will be a net positive for consumers down the road in terms of pure dollar spend.

Companies aren’t naive to what’s happening right now. They have more data and insights on consumer spending than we do. As such, anecdotally prices seem much higher than before. Part of that is due to the war in Iran, but I struggle to believe that is the only reason.

As companies get smarter about agents and AI doing our shopping for us, I’d imagine we’ll start to see prices increase to accommodate. Perhaps that is the product of the free markets — consumers may be willing to spend more if AI does the shopping for us.

A new office

I moved back to New York a little over 17 months ago. We wanted to centralize our office in New York so we can be in-person. The results have been astonishing and we’ve grown significantly as a business while only growing headcount slightly.

I know remote first companies can work, but for me and Secfi, we’ll always be some sort of an office first culture with flexibility attached. The benefits of being in person are just too big to ignore.

We’re doubling down on our office and will finally be looking to move out of the coworking space and into our own unit. It’s time and it’s fun in many ways, but it’s also not easy. Hiring plans change all the time.

We want room to grow into, but not too much room that it feels hollow. We need something nice, but also within the budget. Every neighborhood in New York has pros and cons and everyone has preferences.

Given that we’re an office first team, a nice space will also go a long way in hiring and retention. Lots of fun times ahead, but lots of work to be done in the meantime.

The process

I haven’t watched the Saban documentary yet, but it’s been on my list when I have some free time. I heard it’s an amazing watch and there’s a lot to learn from the greatest coach of all time.

One part that I saw on social media that I’m excited to watch is when Nick Saban talks about his process and why that is the most important thing rather than results. He was once 3 holes from finishing at Augusta, and his caddy told him that he could bogey every hole from here on out and shoot under 80. You can probably guess what happened after that.

Saban uses that example to emphasize that it’s always about the process and what you can control. In sports, you can do everything right and still lose the game. Sometimes another team is simply better. But more times than not, if you stick to the process and execute correctly, that’ll produce the result you want. See Saban’s national championship records.

One of the more frustrating parts about my job is similar to sports, you can work your ass off and do everything right, but something just doesn’t pan out the way you want it to. Sometimes the numbers just don’t line. Or timing. Or the broader market just impacted you.

In business just like in sports, results matter of course. But how you get to a result is by focusing on the process, not the other way around.

Team culture

It’s been a tough football season so far for my Washington Huskies and an incredibly one for my San Francisco 49ers. It’s been an interesting tale of two cultures and teams.

My Huskies had a weird offseason with our Head Coach seemingly looking for ways to get out of Seattle. He flirted with the UCLA, Michigan, and Florida jobs, and got none of them. Then our “star” QB hopped into the transfer portal only to be brought back because of a contract he signed.

My worst fear was that the locker room had been lost and he players weren’t going to respond well to either of those. At the half way point of the season, it seems that things have gone worse than even what I thought was possible. We are simply too talented to be 3-3 and the coach has lost the locker room.

On the other end of the spectrum, the 49ers also had a weird offseason. Our head coach got into a car accident and was absent a lot of training camp. Injuries and jokes about the substation causing those injuries were everywhere. But the team has excelled all expectations and is currently the Super Bowl favorites and undefeated after a big win against rival Seattle on Sunday.

It’s clearly a tale of two cultures and locker rooms. One in the Huskies where there is no team chemistry when your coach and QB, two of the highest paid people in the building wants to leave. The other side with the 49ers shows a team that clearly loves playing with each other. They seem to be playing with a chip on their shoulders. The way they hit sand played on Sunday with unsung rookies making huge plays shows that type of culture in that locker room.

As a big sports guy, I’ve always tried to bring that locker room team mentality to work. There’s a lot of lessons to be learned here, but chiefly amongst them is that if someone doesn’t want to be here, it’s not worth it no matter how talented they are.

Ups and downs of life

It’s 1pm on Columbus Day or Indigenous Peoples Day depending on who you ask. I had an incredibly special morning with Colin. Sophia is working today and I’m supposed to have the day off, so I’ve been on childcare duty all morning. I took full advantage and was excited about a father-son day.

Colin and I spent the morning at the Prospect Park Zoo. It was a simple morning, but one that brought me so much joy. Watching him get excited to feed the farm animals and watching him glued to the window watching the fish swim was special. Showing your child the world is one of life’s simple pleasures that I won’t take for granted.

Right after I got Colin down for his nap, I got a text from one of my close friends from high school and she let me know that her sister’s cancer may have spread to her lungs. Needless to say, she is devasted and her heart is heavy. It was a heartbreaking moment reading that text and seeing someone that you love suffer and have to go through something like this.

It’s been a rollercoaster of emotions for the last hour or so. It’s a weird feeling watching my son nap and smiling knowing that I helped bring him to life, and also going through news like this where life is so fragile.

I don’t really know what else to think besides that this is a reminder that everyday on earth is a blessing, and I need to stay present and enjoy every moment. I plan to do just that with Colin this afternoon after his nap.

AI vs real-life trainer

It’s Friday and I’m ready for a nice relaxing weekend for a nice break between conference weeks. It was a great week of work but there’s so much going on right now and a breather is going to be nice. Monday is a holiday, and I’ll have Colin solo while Sophia is working and I’m looking forward to a nice father-son day.

I did a free session with a trainer at my gym yesterday. I was reluctant but they offered to help me get some of my metrics like my VO2 max and body composition so I thought the data would help. I had worried that the session would be a bit useless and a waste of time/workout and unfortunately that ended up being true.

He was a nice kid who had a degree in this space, but ultimately, my Whoop AI “coach” was a lot more knowledgeable and helpful than a real life “coach” from my gym. Of course, it’s not one size fits all and I’m someone who has been working out consistently for the last 20+ years so I’m probably not in the target demographic.

With that said, it got me thinking on where this world is headed when all the knowledge is in our phones and accessible at any point. A real life trainer does add value in that they provide motivation, accountability, and in-person coaching in which AI may lack. Most trainers provide that of course.

I don’t think most trainers are going away anytime soon. Many people prefer in-person coaching and need that help. But like any other profession, perhaps the low level work in the job will start to go away and the ones that will actually make it and build a large client base needs to uplevel quickly. Unfortunately, the trainer I worked with still has some ways to go until I get real value out of it.

Stocktoberfest

I’m back in office after attending the Stocktoberfest conference the past couple days. It was a great event and I regret not attending in previous years.

We kicked off the conference on Tuesday with a fun event at Century Country Club. A group played golf and another group played tennis. It was a fun, but tiring and long day. I feel fortunate that I get the ability to golf as part of my job and I need to do better being more appreciative of the times.

I was candidly a bit negative about this because I had to get up extra early, and then go into a long day of networking after golf. Yes, I was tired and my Wednesday was a bit of a struggle, but was it worth it to play a round at an exclusive country club? Absolutely and I need to have a more positive attitude. Horrible Whoop recovery score and sleep debt aside.

The conference part was Wednesday at City Winery and I learned a lot from some great presentations and chats. There was a wide mix of audience here, and a large group of public company investors and traders.

In the last few years, I just haven’t had the time or energy to focus on trading shares and I’ve gone pretty much full index save for a few positions. Stocktoberfest definitely got me thinking about things much more and made me want to get back into things. We’ll see if I can find the time to do things. Maybe once Colin is a bit older.

I’m glad to be back in the office and have mostly a clear schedule today and tomorrow to really get caught up after 2 weeks of conferences. It’s all good stuff and I’m grateful that I got to attend, but there’s work that needs to be done and I need to put my head down and get shit done again.

When will FinTech be back?

It was nice to be home and spend a full weekend with the family. I was only gone 5 days from last weekend, but it always feels like a long time away with how fast Colin has been growing. My weekends are much less interesting nowadays as a father, but I wouldn’t have it any other way. Plus the 50 minute nap I took on Sunday was magical.

I’ve got the next weekend and half at home before I fly back west to Vegas for Money2020. Myself and 3 others from Secfi will be attending and we’re excited to get back to Money2020 after a few years break.

In the last couple weeks of planning our attendance, we’ve noticed that the event is much more dialed down than it was a few years ago. There’s fewer companies and investors attending. The infamous Money2020 party spreadsheet is a fraction of what it used to be. I’ve heard that a lot of the FinTech focused VC funds have pivoted or have been winding down.

FinTech is a tough place to be right now. We went from everything is a fintech to the crypto boom, and now we’re sitting here in 2026 in the world of AI where people in fintech may have flocked to greener pastures.

I don’t believe fintech is dead by any means. Fintech in general is an industry that’s naturally going lag behind other industries due to the high regulatory environment. AI in fintech is really just getting started and I’m excited to see the future. This is my first time going back in 3-4 years, and I’m excited to learn about what’s being built in this day and age of AI.

It may be early for us as investors, but things are cyclical, and I’m willing to put money that fintech will be back in a few years, if not sooner.

The vibes seem off

Being at this conference the past week, I couldn’t help but notice that the vibes just seemed off among a large subset of investors. Not everyone of course, but the majority of investors that I spoke to had similar views into what’s happening right now.

The thing that I kept hearing was “the company is growing like crazy, but I just don’t know how this all shakes out”.

It’s a similar feeling to the one I’ve been having. We’ve never seen companies grow like this before this age of AI. Companies that are 1-4 years old are generating hundreds of millions of revenue and setting unprecedented growth rates. It seems like every other week a company claims “we’re the fastest growing X to get to $100M of revenue”.

That’s all great, but there’s a general uneasiness with what’s happening. Call exploratory revenue. Call it double revenue as lots of these companies are reselling inference. Whatever is happening right now is making a lot of investors uncomfortable and thinking that this won’t last forever.

Of course, there’s a lot of money in VC and they’re not foolish capital allocators so perhaps this is different. But especially among the public company investor pool, there is a general feeling that this is all being marked up way too high and the sentiment amongst the few that I spoke to was that they want no part of these IPOs at these valuations.

My Whoop coach

I’m back in New York after getting to bed at 2am after my flight last night. Waking up after sleeping 4 hours was not fun, but hugging my son after 5 days away cures everything. It’s going to be a 4 coffee kind of day, but that’s life.

Last year prior to getting a Whoop and having a “coach” in their AI chatbot, I would have used today as a way to catch-up on exercise and training that I missed out on. I’m tired but I always felt the need to power through and get a sweat in to get my body right. The thought process was that getting exercise in is always a good thing and the endorphins definitely help make me feel better.

It turns out that is the last thing my body actually needs. I argued with my “coach” a bit this morning on my commute, but it’s a pretty obvious that powering through a workout is actually counterproductive. Slowing down to get healthier always felt counterintuitive to me, but the data and science doesn’t lie.

I find it silly that for someone who prides himself on learning that it took me 36 years to figure this out despite working out consistently for almost 20 years. With that said, it’s better late than never and I’ve been feeling better overall since getting my Whoop and trusting the data/science.

Conference wrap-up

I wrote yesterday after my conference’s morning kickoff that the bankers seemed optimistic on the future. At the networking reception afterwards, I met a handful of public market investors who buy IPOs and there was a much more pessimistic sentiment among that small group that I spoke to. There was a strong feeling that private market valuations are inflated and they weren’t excited about investing in many of the IPOs going forward.

Who is right in the end? Well.. both could be right. We could see a crazy amount of IPOs before valuations reset back to a baseline. Of course neither could happen in the short-term either.

On the other hand, I was fortunate to sit in presentations and meet a handful of operators at the forefront of amazing technology companies. I met someone building an airplane/helicopter hybrid. I met investors discussing the physical AI companies. I learned a lot yesterday.

This morning I’m feeling grateful that I get to do this for a living. I’m constantly surrounded by smart and ambitious folks who are all trying to navigate this world of technology, company building, and investing. It’s not an easy job, but being able to learn and be part of this ecosystem is a blessing and I don’t take it for granted.

Optimism in Silicon Valley

I’m in Palo Alto for an investor conference and it’s been nice to get away from NY and get back to the heartland of tech. There’s a ton of interesting companies here that we don’t typically get to work with, whether they are just too early or in an industry that we just don’t focus on. Going to the humanoid robot demonstration just to see things live has been something that’s fun.

The overall view from the bankers here is one of optimism. The head tech banker expects to see 2027 become a year of IPOs greater than 2021. It’s a bold prediction and truthfully one that is self-serving for the bankers. With that said, it’s a prediction that I’d be more than happy to come through so I’m rooting for him to be right.

San Francisco

I was only delayed 1.5 hours on Saturday morning on my flight out to San Francisco. Out of perhaps the 10 delayed flights I’ve been on starting this summer, this was easily the best one. I got the notification while I was still in bed, and ended up going back to sleep another 1.5 hours. Besides that the flight was as planned and I had the President’s Cup to watch in the morning followed by college football. I wish all flights could be this easy.

I had a nice weekend seeing old friends and family. I’ve only been gone a year and few months but so much has changed. My Dad is getting older. My friends are going through lots of life events. The city is changing so much. It does make me a bit sad that I’m missing a lot of it while I’m out in New York for the next few years.

This morning I got an early lunch at West Portal where I spent a lot of my childhood with friends. The old movie theatre is shuttering and there’s new hot restaurants opening left and right. As I was walking to the MUNI station to catch my train to downtown, one of my childhood best friend’s Moms popped out of the store.

It was amazing to run into her as she served as almost another Mom to me during my childhood. I hadn’t seen her in maybe 10-15 years, and her son and I haven’t seen each other in a similar time frame. It got me a bit emotional just walking around West Portal where I spent a lot of my childhood years and also running into her.

It was yet another reminder just how fast life is going by. I’m planning on coming home for a little over 2 weeks during the holidays with the family, and I need to make sure to make a point to catch up with old friends and really make use of my time home.

Starting with Muse

I downloaded Muse yesterday and decided on holding off on connecting most of my personal accounts. It appears that it’s still a great personal agent even without access to my email and some of my other apps. Right now, I am using it monitor prices for my flights back to SF for Christmas and it seems to be pretty awesome at doing tasks like that.

With my guard up right now, I think the best course of action is to take things slow with these agents. They can do my flight research, but I can still take the 5 minutes to actually book the flight. Similarly, I’m happy to let Muse book my reservations and my golf tee times as well. I was hoping for a simple agent like this that can handle a lot of my basic tasks and Muse seems perfect for my needs.

Meta’s stock price has been skyrocketing since Muse was released. It’s up 36% this month. I can imagine that we’re going to see personal agent apps popping up left and right. The funny thing is that Claude and other providers are already doing the same tasks that Muse can, but distribution seems to be key here. Muse is an easy and user friendly interface for the non-technical folks. Not to mention that pretty much every American has an Instagram or Facebook account already, and your personal preferences (data) is loaded in automatically.

For now, I’m having fun exploring the different apps and tools. And I’m happy to have a personal assistant that can give me more time in the day.

Are we back in 2021 again?

I’ve been fighting a week of fatigue and feeling just a bit off. My data in my Whoop also shows it with a wall of yellow recoveries after more or less 2 full green weeks. It took me a few days but I’m starting to realize that the seasonal allergies are impacting me more than anything. My wife and coworkers are all going through similar or worse allergies.

Looking at my data and my Whoop has caused a bit of weird anxiety at times, but it’s the price I pay to learn about myself and my body. And I guess I’ve developed allergies over time that show up much more in fatigue rather than congestion.

There’s quite a bit of uneasiness in the market right now in my conversations. While the people that are much smarter than I am are generally not ready to call a reset or correction, I can see quite a bit of vibe shift in the recent weeks.

From my standpoint, it feels a lot like 2021 again. Companies with spiking revenues are raising at high multiples and valuations, but quite often that revenue is basically just reselling inference meaning it’s shakier revenue. We’ve now crossed over into the territory where companies with little to no revenue are raising ridiculous valuations. In addition, I’ve started to hear some rumors about some of those companies looking to go public. When do we start seeing SPACs again?

I get it. This time is different with a real new technology coming into the fray versus just inflated valuations due to ZIRP. But you can’t ignore a lot of the similarities of investors chasing logos and quick markups. How long this will all last is beyond something I can answer, but I don’t think anyone can deny there is a bubble as there always is a bubble when a new technology like this emerges.

More delayed IPOs

There seems to be something in the air this week. Some members of my team have been feeling off and that’s made me feel a bit better as I’ve always been feeling out of it. I woke up Monday feeling like I got hit by a dump truck. Tuesday and this morning have been much better, but I am far from my normal self and my Whoop is also telling me that I’m low on recovery despite good sleep and having a very normal schedule.

I need to not overindex on things like my Whoop score, but at the same time, it is pretty telling if I’m feeling off and the data also shows that. I reluctantly agreed with the Whoop chat bot that I should take today easy and not go on my normal hard run. It’s been a struggle for me trying to listen to my body and the data, but it’s the smart move.

The somewhat quiet news that’s been overshadowed by the UN meetings this week is a couple delayed IPOs and a much slower September IPO window. Two companies, Holtec Nucler and Bamboo Insurance decided to postpone their IPOs due to market conditions. While these companies are not typically in the hot AI/tech discussion such as Anthropic or some of the inference companies, there is some anxiety about the markets right now.

With Anthropic rumored to go public in October, there seems to be some doubts that they will actually make it out there. There was an unverified rumor that Anthropic delayed their IPO until November. The post Labor Day IPO rush seems to have gotten to a sluggish start and tech employees and investors are holding their breath.

Muse

I had heard about how impressive Meta’s AI agent app Muse was performing and I wanted to test things out. I downloaded the app this morning and got close to setting things up before I paused and decided to do a bit more research first.

I’ve been looking to play around with a personal AI agent for some time now. I went as far as to look to get a machine for OpenClaw and test out other agents months ago, but decided against it as I knew that it was still early. I figured that I could spend hours setting it up to likely be disappointed. Furthermore, the lack of safeguards was worrisome especially because I deal with a lot of sensitive data and I kept hearing that even technical people had problems.

With the launch of Muse which is meant to be a consumer AI agent app for non-technical folks, I was pretty excited to test things out especially after hearing the generally positive reviews. I was hoping to start small such as asking it to book reservations, research places, and search flights for me which Muse seems to be really good at.

During the set-up, I realized that I was going to be giving Meta effectively all my data including my emails and it gave me significant pause. Perhaps this point is all moot anyways. Anthropic already has most of my data from a work perspective and big tech companies getting access to train may be the trade-off.

But candidly, I had a weird feeling about Meta in general. I have an Instagram already so none of this is really new, but I do have a general distrust about Meta than I do perhaps a Google for many reasons. Perhaps I’m overreacting a bit as this is all inevitable, but for now, I decided to hold off and talk to some people before connecting everything.