The money is flowing

I’m officially starting to get a bit worried. It feels a little bit like 2021 all over again. Companies seem to be raising money at a ridiculous clip. I know of a handful of companies who have raised 2 rounds this year at significant markups that are about to raise yet another round in the next month or early next year.

I understand a bit of the game that the VCs are playing. The most money you can lose on a $1 investment is $1 and the opportunity for outsized returns and to be an early supporter in one of the big AI winners is massive.

Of course, there are differences than 2021 in that the money is largely flowing into the AI realm versus virtually every startup out there. Still it is a bit unsettling as everyone knows there is a bubble here and people will lose money soon enough. There will be ripple effects throughout tech and the entire ecosystem from this. We can only hope that it’s a correction versus a massive prolonged downturn like last time.

Accumulating assets

One of the struggles this past year with big life changes like having a kid and also moving to New York has been financially related. I should say that we are by no means “struggling” financially. Sophia and I are very fortunate to live good lives out here in New York.

With that said, the cost of living bump of moving to NY, even from SF, and the increased cost of living of having a child has me thinking about money more than I have the previous 5 years before that.

Firstly, moving to New York City even from San Francisco in itself would mean a cost of living bump. Simply put, housing is more expensive here and you get less bang for your buck. While the day to day may be comparable, it is definitely more expensive to live here. On top of that, having a kid is just more expensive. You need an extra bedroom which adds to the cost of living. And you also add childcare on top of other expenses to provide for a human.

Again, I am not complaining. I live a great life and Sophia and I are fortunate to be very happy with where we are at. At this point of my life at 35 with one kid though, accumulating assets has been top of mind and unfortunately, that has really stalled out in the last 6 months since moving to New York.

I’ve been telling myself to give myself a bit of a break as this increased spending would happen to anyone. At the same time, I want to make sure that we get back to a world of accumulating more assets in 2026.

A half-year break from saving due to life changes is acceptable, but it’s time to start reeling things back and putting some more cash and investments on the balance sheet.

Multi-tasking and the art of doing one thing at a time

In my ever growing list of personal self-improvement wishes, one of the top items that I am actively working on is eliminating multi-tasking and focusing on one thing at a time.

This almost always has to do with me trying to do something personally while also balancing work. I had a recent frustration yesterday morning. With Colin home from daycare and Sophia and I having to alternate childcare and working, I tried to get a quick workout in the morning before work began.

Working out is usually a great escape for me to be present and take a break from the realities of life for a bit. I love the break and the subsequent endorphin rush that comes from it. But I decided to effectively nuke the mental clarity from my workout by letting work seep up and ruin my workout.

I had planned to get a quick and efficient 45 minute workout in, and be at my desk by the top of the hour. Instead I spent over an hour doing a half-assed workout and half-assing my work with no major productivity gains but additional stress. It was the worst way to start my day.

Unfortunately, I do things like this way too often at this point from trying to work while getting ready in the mornings to trying to work while feeding or playing with Colin. It’s a terrible habit and I need to be better for my own sanity and happiness.

Loving what you do

Just when I thought I was becoming a well-seasoned veteran as a parent, we’ve been dealt yet another curve ball with a Tuesday Federal holiday and a daycare closure. With all due respect to the veterans, I don’t ever recall being granted this holiday off in the past and both Sophia and I were shocked to find out that we’d have to be home with Colin today. It’s going to be a challenging day navigating work and childcare, but we’ll get through it.

On another note, I saw a tweet from UW radio broadcaster Tony Castricone yesterday and it had me thinking even into today. It was a long tweet but described his hectic 24 hours flying to cover the UW football team in Madison and then the UW basketball team the following day in Waco before flying back to Seattle.

Tony said something in the Tweet that really stuck with me.

“They say if you love what you do, you’ll never work a day in your life.
I disagree. I think if you love what you do, you’ll never work harder on anything else, and that’s why you’ll be successful at what you love.

Happy to be home and grateful to do this everyday. 🙏”

— Tony Castricone

I do believe I like my job, but that cliche quote that I’ll never work a day in my life has never resonated with me. For one, despite really loving my job building a firm like Secfi, there’s a lot of things that you have to do as part of that job that just downright isn’t fun. Of course there’s parts of company building that feel more like work versus working on a passion project.

That’s why I loved Tony’s adjustment to the cliche quote. I do love what I do, and while it’s not all fun and games all the time, there’s nothing I’ve worked harder on before in my life than building Secfi.

Monday musings

I had an exhausting weekend with the in-laws and other family in town celebrating Colin’s 1st birthday. On top of activities for Colin, Sophia and I also went out to dinner Friday to take advantage of the free babysitter for the night. And then I went out with some friends on Saturday as it had been a few months.

It was a fun time, and I was excited to have guests over to celebrate Colin, but these busy weekends do take a toll on me and my rest. While Sophia and I do not want to get to a point where we stop going out, maybe I need to stick to 1 night of fun and 1 night of rest going forward.

On that topic, I’ve made a lot of strides that I am proud of in the last 2 years. Perhaps a couple years ago after a busy and full weekend, I’d be sitting here in a terrible state on a Monday perhaps half asleep with a lot of brain fog. Today, I’m in a good spirits, ran 3 miles before work, and have had an incredibly productive day so far. Slowly but surely, I am learning how to treat my body better.

On the work front, things seem oddly quiet but busy at the same time. We are not expecting anymore IPOs this year with the government shutdown and the holidays approaching. I’m sure there will be a pick-up of private market activity as we get close to the end of the year, but I’ve also heard that many funds and companies are pushing off things until next year at this point. Perhaps the busy comeback year has people feeling content on where things are at right now.

Focus

I am certainly glad that I am not flying anywhere this month as this seems like a nightmare scenario. The government shutdown is really starting to take it’s toll and while it has not impacted the majority of Americans, that will start to change. Of course, the government workers and the most needy are taking the fall for the rest of us. It’s a sad situation and reflective of the political world we now live in. And for the record, I blame both sides here.

On another note, the theme of the week for me has been focus. I feel like I’ve got a million things going on, none of which are incredibly urgent but everything feels critical. My brain has been in a pretzel all week with the context switching and trying to keep my head above water working through the many different workstreams.

At this point, it’s really time to triage some of these tasks and things are simply just going to have to wait or be deprioritized. On a small team, there is always going to be the feeling that we need to do everything or else there will be a missed opportunity. But over the years, I’ve learned that trying to do everything is usually much more counterproductive.

In order to be the most efficient, we need to be diligent with our time and make sure we stay focused on the most important tasks. That will almost always mean better results when the dust settles.

The private markets resurgence

Two big moves happened in the pre-IPO secondary space recently that went relatively quiet. Morgan Stanley announced that they acquired EquityZen last week and today it was announced that Charles Schwab acquired Forge Global which was a publicly traded company.

It’s been fun to see some activity in this space as it’s been mostly quiet the last few years since Forge went public. Two of the biggest legacy secondary marketplaces have now been acquired by large financial institutions. Undoubtedly, clients at these firms are demanding access to pre-IPO investments and these acquisitions help them achieve that.

Of course, this is all great news for Secfi as we operate in this space. We are adjacent to EquityZen and Forge, and while some may see us as competitors, we partner with them more than compete. They are both great companies and I’ve enjoyed meeting and partnering with many folks there.

I’m happy for all my friends at EquityZen and Forge, and for everyone building in this space.

Happy Birthday Colin!

It’s Colin’s 1st birthday today. While I can’t believe that it’s been a year, I also can’t believe all the things that we’ve been through in the last year. Like the saying goes, the days are long but the years are short.

Prior to Colin being born, I did not know that I was capable of loving anyone or anything more than I love my son. There is nothing that brings me more happiness than seeing him in the mornings smiling back at me.

Watching Colin grow has been the biggest joy of my life and I’ve been doing everything possible to cherish the moments I have with him. I know that one day I’ll be writing a blog post on his 18th birthday talking about how time has gone and that he’s now an adult. That makes me sad, but the impermanence of everything is what makes life beautiful.

Life this past year has been the most rewarding year of my life, but at the same time, likely the most challenging. In order to be a better father, I’ve really had to grow up. I’ve had to come to terms that being a parent means giving up a large part of your own life. While it has all been worth it, it has not been easy. It’s been a rollercoaster of a year with a lot of highs and a lot of lows, but I’ve finally gotten to a really good place right now.

I suppose now Colin is officially a toddler and not an infant anymore. There’s going to be a lot of fun developments coming in the next few weeks to months with his first steps and first words likely. For now though, this week and weekend is about celebrating the little guy that has brought so much joy to his parents and family. Happy Birthday Colin!

Another election day

It’s election day here in New York and it’s going to be a heated one. While it’s been more or less accepted that Zohran should walk away a winner tonight, there seems to be a large push for Cuomo and maybe a sliver of hope for anti-Zohran folks.

I’m not one of the folks who believes Zohran is an anti-American who wants to implement Sharia law (these are real ads I was served today). At this point, I do believe that he’s a good person that wants to try to make positive change for New York and the country.

With that said, I do have a real fear that these policies simply don’t work and will make things worse for New York. I have seen this script before in San Francisco and other west coast cities where liberalism goes too far and we lose a bit of common sense.

If elected, my hope is that Zohran can surround himself with experience and smart individuals who can help guide him to implement change within reason and common sense.

Doing less to get more

We had a great weekend. It was Colin’s first Halloween and while he like won’t remember what was going on, it was really fun spending time with him on a festive day. On Saturday, Sophia and I spent some time in the city and then hired a baby sitter so we could go out to dinner. It was a great weekend.

One of the key learnings in my first year as a parent is that I need to do less to get more out of my weekends. There were many months where I had tried to do too much with Colin. Whether that was being too ambitious with my day with him, or just planning way too much social events, or traveling too much.

My life has gotten significantly better the last few weeks when I have committed myself to doing less. For example, we can go out trick or treating with Colin but also realize that he does not know what’s going on and we should head back so he can play and get some energy out versus sitting in a stroller. We can also grab lunch in the city but need to be back by 3:30 for his nap or else we’re going to have a cranky kid.

Our weekends are infinitely less stressful once we’ve come to terms with the new reality and stopped trying to force things to feel like the pre-kid days. Things are not the same as they were before and likely will never be. After about a year, I’ve finally figured that out and have been enjoying our weekends more.

Fridays

It’s Colin’s first Halloween and it’s been a ton of fun for Sophia and I. We dressed him up as a piece of sushi and he’s incredibly cute today. It was a joy dropping him off at daycare with the other babies all dressed up. I’ve never been a huge Halloween guy but I’m loving it as a Father.

On another note, it’s a quiet Halloween Friday in the office where I am maybe one out of five people in the entire coworking space. I do find it interesting just how normal work from home on Fridays has become. I know it’s Halloween and whatnot, but the norm has really become to work from home on Fridays nowadays.

Not that long ago we had companies giving perks like Summer Fridays and work from home on Fridays during non-busy times. My old firm would let us work from home in the off months on Fridays and it was always a treat. I am generally a fan of the trend, but I do find it interesting that Fridays have just become effectively a half day for most people.

I’ve started coming into the office on Fridays myself to try to be as productive as I can with the hopes that I can log off early and enjoy some time before I have to pick-up Colin from daycare and be a Dad all weekend.

At the office especially when it’s quiet, I have all the time to myself to really sit down and grind out work. I’ll usually treat myself to a nice lunch in the city somewhere and then wrap up from a new spot like a coffee shop to enjoy Manhattan.

Keeping motivated

It’s a rainy and windy morning here in New York. Our coworking space feels like there’s maybe 25% of the normal traffic for a Thursday as presumably most people decided to just stay home.

On the work front, there’s not much urgent or pressing right now given the time of the year. There’s no shortage of things to do, but I’m enjoying the lack of hard pressing deadlines right now.

With the weather turning and work in a relative lull, I’ve been pushing myself to enjoy life a bit, but also doing my best to stay motivated and get shit done. It’s sometimes easier said than done especially on days like today where it may be tempting to stay home and have a slow day.

While it may not seem like it, these weeks are incredibly important weeks. Whether it’s knocking out some projects that have been lingering or just accelerating things to get ahead of an end of year rush, these weeks can make or break a quarter or a goal. What we do this week could mean the difference between having a relaxed Christmas or a hectic busy one.

There’s a balance of course. I’ve got to stay motivated and progress things, but it’s also the time of the quarter where we need to relax a bit.

Nvidia $5T and where does OpenAI end up?

Nvidia became the first company valued at $5T yesterday. Apple and Microsoft both crossed $4T as well. The AI boom has been good for the largest players in the space. Call it a bubble, but investors are hungrier than ever to get into the AI boom.

OpenAI also announced that they have restructured their partnership with Microsoft and are now officially a for-profit company. This paves the way for the company to eventually go public.

With the last round at $500B, I wonder how big this IPO can actually get? What is the end goal at IPO? A $1T valuation or perhaps even higher? At this point, I’d wager that $1T would be the floor that they would consider going public at. And if I’m being honest, I wouldn’t be surprised that they get there sooner than later depending on the demand right now.

Is it a bubble or a perhaps once in a lifetime technological advancement? It’s clear that this is both. I don’t know how this will all end up, but I’m still of the belief that the largest companies will benefit the most given the high cost of running AI. So far that has been true.

AI layoffs

Amazon was the big news headline in the tech world as it laid off 14,000 corporate employees today citing making the company leaner and leveraging AI. Apparently, it could affect up to 30k employees and will touch every area of the business. It’s also the largest layoff in company history.

I don’t doubt that companies, especially the large tech companies, need to downsize after the hiring spree post COVID. I know people who constantly brag about how little they work and how much they get paid. However, the size of this layoff is definitely eye opening.

Undoubtedly AI is going to continue to drive layoffs as companies seek to get more efficient. For better or worse, this is just the start of these AI driven layoffs, specifically in big tech. Other big companies are quietly also conducting layoffs just without the scale and noise.

Savoring the last few weeks of baby Colin

I had a good weekend as a solo parent with Colin. We had a fun time hanging out and I took him to playgrounds, play gyms, and even a restaurant for lunch. It was a much different weekend though as my entire day was pretty much focused on Colin. There weren’t many breaks besides his naps and I had 2-3 hours every night after he went to bed for myself at best.

As saying the goes, nothing easy is ever worth it. I suppose that’s why being a parent is incredibly rewarding as it certainly isn’t easy being a Dad. You are definitely giving up most of your personal life for your kids. It’s a choice that I’m happy to make and would make again, but I do miss some time to myself.

I don’t think it’s even the social events or the TV that I miss the most. For me, I really miss the days of being able to go to a cafe with my laptop and just catch-up on things leisurely with no agenda or time frame. I do know that things will continually change as Colin grows older.

It’s hard to ignore just how fast he’s growing. His naps are getting shorter. He’s getting more demonstrative and doing a lot more physically. His personality is starting to come out. I think it’s likely that he’s going to be walking in the next few weeks or so. I’m excited for him to be a toddler, but going to try to savor the last few weeks of him being a baby for now.

Enjoying the moment

Watching Colin grow has been the biggest joy of my life. This morning, I couldn’t help but just stare at him play with his toys. Just a few months ago, we bought him this toy chest where you can take balls and drop them in at the top and the ball rolls down like a roller coaster. When we first got it, he didn’t know what to do with it and barely would watch the balls roll. Now he’s picking them up and dropping them in to watch them himself.

It’s the simple things like watching him develop and progress. As everyone says, these days go by real quick and I need to make sure to enjoy every moment of it. I’m doing my best to stay present whenever I’m with him and focus on just being with him and enjoying the moment.

However, it’s a lot harder than I’d like to admit. There are many moments when I’m just thinking about work with him and I’m not fully present. Last night, I was trying to push through a grocery delivery order while also playing with him. The craziness of life does creep up and my monkey brain has always liked to jump around.

However, the most important thing right now is Colin and I need to remember that I’ll miss these days. Everything else can wait for until after bedtime.

Special weekend of solo parenting

Sophia left this morning to go back to SF for a wedding so I’m solo parent for the long weekend. I’ve done it before so I’m not worried or stressed, but undoubtedly it is much more difficult and you just have to be more on top of your game.

Difficulties aside, I’m excited for the alone time with Colin. It forces me to be much more present and focused on Colin. For better or worse, I have to be laser focused on just being a Dad and taking care of him.

I’m not sure what we’ll do yet. I’ll probably stick to the model of one activity a day as anything more than that is just too exhausting for me and I don’t want to overstretch myself. At the end of the day, at this age, it’s more so spending time with him.

Healthy politics

We’ve been having healthy and educated debates in the office about the NYC mayoral race. It’s been really refreshing given today’s politic environment. There’s a good contingent of folks who are pro-Zohran and a good contingent against him.

We come from different backgrounds and countries, and many of us have differing political views. Being able to have educated and civil conversations about the Mayoral race has been really interesting and eye-opening.

This is what it’s all about. We need to be able to listen to another’s opinions and views, and keeping an open mind about it. I’ve learned a lot from my pro-Zohran colleagues and while I haven’t changed my mind about him, I am more hopeful that he would work as Mayor.

AI content

Since OpenAI’s launch of Sora 2, my social media feeds have been filled with AI generated videos. These videos are getting so good that I’ve had to do a double take at times to make sure that it was indeed AI generated.

The speed at which AI is advancing is remarkable and we’re watching it all live. It was just a year ago where AI generated short clips were barely watchable.

At what point does the majority of content on social media just become AI generated? I’d guess that it’s going to happen sooner than later. I am curious as to how consumers, and social media platforms, reward or nerf AI generated content.

Will consumers remain partial to real people like content creators today? Or will it not matter if the content is AI generated in the future as long as the content is good? There’s something to be said about authenticity in the modern world. At the same time, content is king and people cannot consume enough of it.

Back at it

I’m much happier going into work on a Monday this week after the week off. It’s night and day to where I was a couple weeks ago. I’m stoked to get back into it and close out the year strong. On a personal level, these next 2 months are going to be about living a healthier life style. That means getting back into shape and also a much healthier work-life balance. I want to feel great going into the holidays.

On the work front - the government shutdown has put IPOs for Q4 in jeopardy. We had a strong Q3 performance of IPOs and had thought that we’d see another handful of tech IPOs in Q4. However, the uncertainty of the government shutdown effectively leaves a 2 week gap before Thanksgiving and a 2 week gap after Thanksgiving for companies to go public. I’d guess that many companies will likely just wait until 2026 at this point.