Staying strong

We’re rounding out our first week here in Zadar. This afternoon, we went and found a new apartment in old town which we will be renting for all of November. In a different time, I would normally be stoked to get this awesome apartment in a historical ancient Roman city.

Now I’ve got to temper my excitement as we’re here to take care of my father in-law who has a long recovery back and my mother in-law who is grieving and stressed. There’s no great fix here. It’s becoming evident that my father in-law is going to have a long recovery back even once he gets back to the states. My mother in-law is not handling that well.

I know I need to be strong and support in every way I can. My friends may be the first to say that patience is not my strong suit, and I know I’ve got to be extraordinarily patient in these next few weeks. I know it’s my role to be there for my wife and the family right now.

Difficult situations

We had a lot of great news yesterday after my father in-law got his CT scan back. The bleeding has stopped and it looks like things are trending in the right direction. He is alert and chatting with us. That’s the most important thing.

The difficult part with all this is that the recovery is likely a month or two for the blood to fully get out of his brain. It’s undoubtedly going to be a difficult situation for my mother in-law, Sophia, and myself. We’re still working out details, but I believe the most likely scenario is that we’re all going to be here for at least November together.

This obviously was not part of our plan for November. But I’m choosing to taking things in stride and staying positive about everything. It’s really easy to spiral and complain about being here. Being in a coastal summer vacation town in November is less than ideal. But there’s also a lot of positives.

We can have fun and live a normal life. The Croatians and Zadarians are great and welcoming people. Our work has been very understanding. It will require a lot of flexibility on everyone’s part, but we’ll make it through and hopefully bring my father in-law home healthy with some great stories and experiences.

Why does the world need another X?

Many months ago I was on a tour visiting a bunch of the brand name VCs in Palo Alto. One of the sayings that I kept hearing from multiple investors was, “why does the world need another X?”

That one really resonated with me then and especially now as I’ve gotten more and more into angel investing. Perhaps this is just the nature of Silicon Valley and tech. We are a copy cat world after all. Facebook was not the first social media provider. Google was not the first search engine.

But it’s hard not to see just how many similar companies there are attacking the same problems and competing with each other. In a lot of markets, there would definitely be room for multiple players to be successful. In some, it’s hard to see more than a couple dominate the space.

Of course, sometimes the market just expands much bigger than anyone could imagine… but that’s in rare situations. Nowadays, I’m really looking hard at the market when it comes to my investments as there’s only so much to capture especially in crowded spaces.

Zadar

My schedule and life this week has been weird to say the least. Obviously being here to tend to my father in-law who is bedridden in a hospital has been strange to both Sophia and I.

This is first time in our adulthood that we’re dealing with an immediately family member being seriously sick. Unfortunately, we’re getting to the age that this is likely going to be more common than we’d like. It’s a harsh reality of growing older. Luckily, my father in-law is stable and making good progress every day. Hopefully we’ll be able to get him home in the next week or two.

Both Sophia and I have been battling weird jet lag and odd hours. We’ve been trying to get to bed at normal times, but have been waking up for a few hours, and then falling back asleep until the late morning. That’s been annoying as we haven’t really been able to take advantage of the day, and then we end up working at night.

So far, the city has been kind to us. The lodging here is cheap and we found a great Airbnb host who was very understanding of our situation. He blocked off the entire week for us at his 1 bedroom Airbnb at a great price. The apartment has been a godsend as we can work and have a sense of normalcy.

The Croatians have also been very pleasant people. It’s safe here and there’s no worry about walking around at night. Most people speak good English. And the food is pretty darn good at cheap prices. It is definitely a coastal beach tourist city though and that comes with some drawbacks.

Overall, we are making it through and making the best of the situation. It’s not vacation, and we are still working and tending to the situation, but we’re trying to enjoy our time here as well.

Life and Croatia

I landed in Croatia last night. I wish I was here for more pleasant reasons, but unfortunately Sophia’s father had a stroke while on a cruise in the Mediterranean. He was fortunately able to be brought ashore to a hospital in Zadar. He’s currently stable, but still going through a bit of internal bleeding so things are not in the clear yet.

Sophia and I were debating coming to Croatia or not. We’re glad we did. It’s good to be here for her Mom and help provide some support. We’ll know a bit more today when we visit in a couple hours.

I was able to walk around the town a bit today and this city is beautiful even in the late fall. I don’t know what the next days ahead will look for, but Sophia and I are trying to stay positive. We’re hoping for some better news ahead, and then perhaps we’re able to enjoy Croatia a bit more.

Home

I had a good last day in New York. We had some good meetings and got some work done. At night, I went to see an old friend from college for a drink. That led to meeting some more college friends who were in town. And that led to a very late New York night.

I had purposely booked an early afternoon flight so I could get some sleep so I was thankful to be able to sleep in a bit. It was unfortunately a long journey home though and I couldn’t have been happier to crawl into my bed last night. Even after sleeping nearly 10 hours, I’m still feeling sleepy sitting here writing this at Noon.

After making the New York-San Francisco trip many times over the last 10 years, it unfortunately does not get much easier. The 6 hour flight feels a lot longer and rest comes at a premium. I’ll need to find better ways of traveling going forward if I’m going to continue to make that journey.

NY Tech Week

The exhaustion from the weekend, travel, and long days of meetings finally caught up to me yesterday. I hit a bit of a wall in the afternoon and really had to do my best to power through. I ended up grabbing a quick dinner with a couple people from the team and took the night easy. I feel great today and I’m ready to have a great day to close the week out.

I’ve gone to a couple NY Tech Week events, but admittedly skipped out on a few I registered for as well. There’s definitely a noticeable tech crowd around the city, but being such a large city makes the events a bit spread out. Unlike some of the events in San Francisco when there’s a real concentration downtown, the NY one seems to be a bit more all over the place.

In terms of events, I will say that I always end up enjoying them more than I expect. I went to a talk with the Founder of Rent the Runway and COO of Reddit at the Reddit offices yesterday, and I really enjoyed what both of the presenters had to say. I met a few awesome people and even met a client randomly in person from many years ago.

Generally, these conferences and events are not usually very helpful for Secfi as a business. We work typically with late stage companies and these events almost always skew early stage. With that said, they are definitely great networking events and serve as a good excuse to get a lot of partners and investors together in the same area.

I’ve got one big day today of meetings and getting stuff done. Then I’ll take tomorrow morning off before I fly back home.

The year ahead

New York has been good to me so far. We’ve had a lot of meetings and planning yesterday. And plan to do more of that today.

One prevailing sentiment that we’re consistently hearing from other investors and veterans in the industry is that 2024 is likely going to be another tough year for us in tech. Surely, there will be some IPOs, but the macroeconomic events combined with an election may force a lot of companies to wait for 2025.

Of course, everyone hopes they’re wrong. It’s not what we want to hear, but it’s a very real possibility that we all need to prepare for.

The good news is that strong companies will continue to grow and hopefully start getting close to their 2021 valuations in the coming year or two.

We’ll see how things go.

Epic weekend - Go Dawgs!

This past weekend was one that I’ll remember for the rest of my life. My Washington Huskies knocked off Oregon in a classic college football rivalry match-up. The spotlight was on us as College Gameday was on campus for the first time in a few years and we had the marquee game slot of the week.

The game lived up to it’s bill and there was excellent play by other sides. The Huskies eventually edged it out and set ourselves up for a potential epic season. There’s a lot of hype around us right now, so I hope the team is taking it in stride and continuing to put in the work. Anyone can lose on any weekend in college football.

I came home for an evening and night, and then immediately flew out to New York. I’m a bit tired from the weekend but doing what I can to power through and make sure that we keep this week as productive as possible.

There’s definitely a lot of challenges right now. My biggest thing is making sure that I keep laser focused on the things I can control. I can’t change the macro environment, but I can control my effort and focus.

Nerves

I’m finishing things up at work and headed to Seattle later this afternoon. My Huskies have a huge rivalry match-up against Oregon and it’s being dubbed as the biggest game in perhaps 30+ years. I can’t wait to get to the tailgates tomorrow. I’d be lying if I wasn’t a bit nervous though.

If you’re a true Husky, you absolutely hate Oregon and everything they stand for. They bought their way into prominence with Phil Knight’s money. They are a school known for their athletics first because of Nike. Credit to Oregon as they have been winning the last 20 years and you can’t take that away from them.

My high school football coach always said it’s okay to be nervous before a game, it just means that you care. While I know I’m not playing, I feel like I have just as big of pregame jitters as I did when I wore the pads.

Go Dawgs!

Atlassian acquires Loom

Some relatively big news in the VC/startup world as Atlassian announced that they are acquiring Loom for $975M.

Loom makes a great product that we use at Secfi. In a nut shell, it’s a way to record a video of yourself and your desktop like you would be on a Zoom. Once those videos are recorded, you can send it internally or externally. At Secfi, we use it to send instructions or a walkthrough to our clients in lieu of setting up time for a call. We also use it to communicate async internally. It’s a great product and we’ve been happy with it.

The acquisition price comes in a bit below the Series C at $1.5B in 2021. While maybe not the outcome they envisioned when they raised that round a couple years ago, it’s still a great exit for the employees and most of the VCs. The acquisition clears the preferred stack and employees who hold common stock will have a sizeable payout from their shares.

I am not tied into Loom at all besides being a user. But my guess is that the acquisition comes at a fork in the road. They have a great product that has grown significantly and continues to grow, but growth is likely slowing. So they had a choice to make.

In order to continue to grow, they would likely need to create new products. And if they had an IPO in mind, they likely would’ve had to go down the “platform” route that combines all those products. I assume at some point, they felt that they were best joining forces with Atlassian instead.

Congratulations to the Loom team on getting to an exit!

Reflecting back on the NFT craze

I had a nice night catching up with a couple high school friends yesterday. It’s been really awesome that our high school group of friends has stayed so close over the years. I’ve now known all of them for the majority of my life and I plan to stay close with them for the rest of it.

Sophia told me that I needed to be better at catching up with my friends and I agree. I often get carried about with life and think that friendships nurture themselves. In reality, they need a lot of nurturing and I haven’t been the best at it.

On another note - my friend Francis and I were discussing NFTs as a bit as he still works at a NFT startup. The bear market has definitely taken a toll on the industry.

When the NFT craze was happening, I wrote that I was planning on participating in projects that I wanted to get involved with and trying to stay clear of buying into something for the sake of making money. I’m glad I stuck to that as I don’t have a gaping hole in my net worth right now.

Unfortunately, for those actually building in the space, it appears that the vast majority of those participating in the NFT craze was solely just to try make money, not for any utility. Now that the money has dried up, most the users and participants are also gone.

For myself, I’ve lost some money on the project I’ve bought into just like everyone else. But I did so mainly with gains so I’m in a good spot. I also only bought into projects I wanted to be in long-term which include LinksDAO, Knights of Degen, and the Illuminati projects. I’m still part of all 3 right now, and even golfed last Sunday with a friend I met on LinksDAO.

I hope there’s a bit of resurgence cause there’s some genuinely great projects happening right now. It’ll be interesting to see where things go from here.

The startup risk

In normal times, everyone who signs up to join a startup knows that the risk is failure is very high. For better or worse, that risk seemed to have disappeared during 2020 and 2021 as startups were able to continually raise capital to stay afloat. We’ve now gone back to the normal times and that risk is perhaps never been higher in the last 10 years.

When I joined Secfi in 2018, I came in thinking and knowing that this was more likely than not to fail, purely just on pure percentages and odds. We’ve luckily have been going for 5+ years since then and we have no plans on stopping anytime soon. Still we are a startup and that risk still always runs much higher than working at a much more established business.

The good news about this is that the higher the risk, the higher the reward. A lot of people who are at a startup or have been may not want to stick it out through the bad times. Those that do and are able to make it out will reap the rewards.

Progress takes time

It’s been a tough weekend for the world and humanity. We saw innocent civilians being killed and kidnapped by terrorists. We now have a full-scale war raging in the Middle East and there will be a lot more bloodshed.

As I wrote when Russia launched war against Ukraine that it’s a bit difficult to be optimistic about the world in general right now. I always lean towards optimism and the hope that the humans and the world will figure things out. Unfortunately it looks like we’re heading in the wrong direction the last couple of years.

The optimism in me knows that progress is not linear. The world may need to take a step back or two in order to move forward. Whatever needs to be done in Europe and the Middle East, I hope it’s done as quickly and with as little bloodshed as possible, especially those innocent civilians.

NY Tech Week

A few of us are flying out to New York the week of the 16th to do a lot of in-person meetings and also fine tune our plans for the months ahead. Coincidentally, it’s also NY Tech Week. Despite living in New York for 5 years, I never really participated in much tech related activities out there.

I’m excited to see what the tech scene out there is like. Looking at the list of activities and it’s immediately obvious that FinTech has a much bigger presence there comparatively to SF judging by all the events.

It’s been almost a year since I attended a large event and I’m excited to see what New York tech week is all about.

The EV debate

It’s going to be 85 degrees here in San Francisco for the next few days. While I’m always happy for the nice weather, we’re starting to stray into too hot for me territory.

Sophia and I have been pondering whether we want to buy an EV in the next year or so. Right now, we drive my sister’s 2010 Jetta which is a perfect car to absolutely just destroy in San Francisco. It may be the least cool car I can drive, but having no car payment nor worry about street parking in SF is great.

All that said, we know we will need to upgrade cars in the coming years and I’ve been casually taking a look at the EVs that are out. Tesla was the initial want, but as time has gone on, I’ve realized that perhaps they aren’t the best cars out there.

I still get a bit of charge anxiety living in San Francisco. I will likely always be in SF or NY going forward and it makes things a lot harder not having a house to charge in. I really want to see how the EV charging systems develop over the next years as there should be some big changes.

In addition, I believe we’re at an inflection point of EVs. Most of the biggest car manufacturers have launched their own EVs and I want to see how that develops. There’s some great cars out there and they will only get cheaper in the coming years.

It’s going to be fun to see how the cars develop over the next few years.

Overthinking things

Sophia is gone for the rest of the week and weekend so I’ve rolling solo. I expect a lot of football and golf. It’s supposed to be 80 degrees between now and Sunday so I told Sophia that San Francisco apparently likes it when she leaves.

One thing I’ve really emphasized with my team is to stop overthinking things. At one point, Secfi got so big with so many decision makers that things started moving slower and slower. We’re now past that phase and I’ve really tried to push everyone to get back into that startup thinking.

The majority of discussions or decisions that made day to day have marginal, if any, impact on the outcome. Quite often, that 30 minute discussion on how to word a marketing email just is not worth it.

There’s a lot going on at Secfi and we need to move quicker. Eliminating paralysis by analysis is the first step.

Newsletters

We’ve been writing our Secfi newsletter for about a year now. First, it’s been really fun writing to a large audience. It gets me out of spreadsheets and gets me writing again which is a nice change of pace.

For Secfi, it’s proven to be great for us as a business as it allows us to reach our clients and users in a casual and educational way every other week. We’ve been emphasizing the “air war”, a term I’m borrowing from a16z, which is basically just publishing a lot of content that is helpful. It helps with the company branding and individual branding efforts as our readers get excited to meet us in-person or over Zoom eventually.

So far, we have kept things very educational where our team will either write about a topic that can help our clients or write about a current event topic that is relevant to our user base. We get a lot of positive responses on a weekly basis which is awesome to hear.

Going forward, we will likely look to expand our content base. We’ll look to stray away from just educational to discussing relevant topics around tech or VC. We’ll likely do some interviews with our friends and partners. We’ve also got it on our roadmap to improve things across the board from formatting to getting to a weekly cadence.

Our newsletter has been a huge cheat code for us and we’re excited to continue building it.

Embracing the change and uncertainty

I had a pretty good weekend of rest after a long week of work. It’s been gorgeous here in San Francisco and the forecast has a great weekend in the 80s upcoming. The flooding in New York has me rethinking a possible move there. We’ll see how I feel in the coming weeks.

One of the hardest parts about adjusting to startup life 5 years ago was the unpredictable nature of things. One day you can be the luckiest person and have a huge win at work. The next day the luck can turn and you are faced with a gigantic L which is exactly what has happened to me the last week.

Late last weekend, I had a few things go my way and I was on the verge of some big wins. Things were coming together and we were set-up for a monster October. And by today (Monday), more than half those things that we were working on had fallen through completely for various reasons.

I’ve come to learn over the years that this is just the nature of working at at startup, especially a fintech. It sucks, but you can take one on the chin even when you do everything right. It’s never fun when things go the other way for you, but it’s something we’ve come to learn to embrace.

The psychology of selling

I’m no longer a young buck anymore and I’ve slowly started coming to terms with it. I pushed myself hard these first four days of work putting in some extra hours and I’m proud of what I got done. Unfortunately the end result of pushing myself that hard is that I’m a bit tapped out today. I’m planning on powering through the morning and early afternoon and then starting my weekend/recovery early.

Moving on. One thing that I and others have struggled with in investing is pulling the trigger on selling. Early on in my career, I thought that pulling the trigger and buying stock was going to be the hard part. That’s when the cash leaves you of course.

As I’ve gotten more experience investing, I’ve learned the hard way that selling is much harder. There’s just something psychological about parting with your initial thesis or just taking home a solid win.

If the investment has not worked out, it’s really hard to admit that you were wrong, take your beating, and sell for a loss. What if you were right and it recovers? The FOMO is real.

If the investment is a win, then it becomes hard to just take your win and move on. What if the investment keeps going up and you miss out? The FOMO again is real.

I’ve learned that the best investors change their mind often. It’s a game where you can successful even if you are wrong often. On top of that, the best investors know when it’s time to take your wins. Institutional investors will often hedge their positions. For us retail investors, the best move is often to just sell and take your win.