Gambling

I was reading this morning that it may be a matter of time before casinos open up in New York City. The revenue that would come in is just too big to ignore and it seems like New York may be up next to legalize gambling.

It was a bit fitting as I’m in Lake Tahoe for the weekend and we will undoubtedly head to the casino on Friday and Saturday at the stateline. I understand the downsides of gambling, but as a reasonably responsible adult, my friends and I love the casinos.

Gambling led by sports betting has hit the point of no return. Despite gambling still being illegal in San Francisco, you don’t have to go far to find a bookie where you can place sports bets. I know a lot of friends who have accounts in different states as well.

At this point, states need to come to the realization that this is happening and gambling is an opportunity. San Francisco may want to take note of what’s happening. Perhaps legalized gambling may be that jolt to bring energy back to the city.

Tahoe (+1 for SF)

It’s almost everyday that someone is trashing San Francisco on Twitter. For all the problems that San Francisco has, I don’t know too many major metropolitan cities that provides you access to a vacation area like Lake Tahoe.

It’s truly one of my favorite places during all 4 seasons and it’s a blessing that you can get up here from San Francisco in under 4 hours.

I made it up to Tahoe today for the first time this winter. I needed a change of scenery for a couple days of work as I’ve had a tough week and a half.

On top of all this, I’ll be able to hop on the slopes over the weekend nice and early. When Austin or Miami gets a Lake Tahoe, I’ll start considering moving.

Working from paradise

I spent the morning looking at flights to French Polynesia aka Tahiti. Someone on my Twitter TL had a post saying that it’s cheaper to go to paradise than it is to go to Disneyland and that got my interest.

After coming back from my honeymoon, I’ve definitely have the travel bug a bit and I’ve been doing a bit of dreaming at nights thinking about some of the trips Sophia and I can take this year.

One interesting part about Tahiti is that it’s only a 2 hour time difference from San Francisco. I can theoretically still work on San Francisco time. Of course there’s many other factors to consider… like the fact that you need to actually work rather than just lounge on the beach.

Sophia and I spent some time in 2021 working from New York and Mexico. It was an amazing experience and I’ve had the itch to do it again soon. I’m fortunate to be working at a startup that will allow me to do that, but I do wonder what the impact is on overall productivity.

I feel like I’m disciplined enough to get my work done, but I know not all companies will trust their employees to do the same. It’s a huge employee benefit perk, but I do see how productivity can suffer. I wonder if the remote first companies will allow employees to work from anywhere and if that will continue to become a trend post-pandemic years.

It will be interesting to watch and see how this trend develops.

The misconception with tax strategies

Every week I take a call with a startup employee or founder who is looking for “creative ways to minimize tax”. There are of course, many ways to plan around your taxes and ultimately come out ahead, but these individuals specifically are almost always looking for a silver bullet solution.

In order words, they are looking for a simple win-win solution that will help shield them from taxes. They want to stay in California and not pay California taxes. Or they want to take advantage of the ISO tax benefits without exercising. That unfortunately does not exist. Nearly every legal tax strategy comes with a “but”.

Some simplified examples:

• Eduardo Saverin (one of the Facebook founders) was likely able to avoid paying US taxes on the Facebook IPO. He just had to renounce his US citizenship and no longer can come back to the US.

• You can use various trust structures to avoid gift and estate tax in the future, but each trust has strict requirements such as you gift the shares completely to charity in the future or the shares are permanently in the beneficiary’s name. You may avoid taxes on the transfer of shares in the future, but you’re quite literally giving them away.

• You can take advantage of tax breaks on stock options if you exercise earlier. You may even qualify for QSBS which is the biggest tax break for early stage founders and employees. However, it requires that you buy the shares today and risk that cash if your company does not make it.

Of course, things are a bit more complicated than the above. This was meant to be a simple view to prove my point that there’s no perfect and easy tax strategy. There is a cost to all proactive tax plans… quite often that cost is worth taking.

But for those that are looking for an easy answer to avoid paying taxes as an American citizen, you may need to lower your expectations.

Tough times and tough decisions

I haven’t felt like writing much about work for the last month or so. A large part of that is due to the fact that there’s just not that much great news coming out of tech recently. It’s hard to live this day in and day out. And I didn’t want to add the pessimism by writing about it.

It is the reality of the times right now though. Like many other startups and tech companies, we’ve had to make a lot of tough decisions over the last year.

I’m not sure when things really bottom out. No one really does. But I do know that things are going to be hard this year for all of us in startup land. I took a lot of the last few weeks to get myself and my team mentally prepared for what’s coming.

The good news is that once we get through these times, we’ll be battle hardened and a better company afterwards.

Honeymoon recap part 5: Singapura, Singapura

After 5 nights on an island, Sophia and I were ready to get back to a city. If I’m being honest, I could’ve probably stayed an entire month and been okay with it, but knowing that your vacation has to end at some point, we were glad to get to Singapore and wrap things up.

We decided to end in Singapore so we can meet up with our friend Alyssa who moved there and I always feel like it’s good to end in a city. There’s something really depressing about going straight from the beach/island back to a city. I hadn’t been to Singapore in almost 20 years since I was a kid so it was pretty awesome coming back.

The first thing I noticed when I landed was just how many more skyscrapers there were and how many more are going up right now. The amount of construction was crazy. After the hectic atmosphere of Vietnam and Thailand, it was nice being in a place like Singapore where everything just works quickly and efficiently.

I suppose there’s not a whole lot to see in Singapore. It’s an amazing city to hang out, eat great food, and drink. We did the typical tourist things like have a drink at the top of the Marina Bay Sands and check out the light show. But really we were just there to hang out with Alyssa and eat some amazing food.

We stayed near Chinatown which was perfect as there were some amazing hawker centers within walking distance. As expected, the cocktail bars were absolutely amazing as well. The bar and party scene in Singapore is fantastic. On Friday night, we went out in Hajji Lane which was a cool area that was a bit more rugged but just a great place to start the night drinking outside.

Of course, some of the food highlights were in the hawker centers. We had some amazing chicken rice and char siew at Tiang Baruh hawker center. Having a friend who has lived there for half a year paid off when it came to food. Perhaps one of the best things we ate all trip was the black pepper crab at Long Beach Seafood. On our last night, we went to KEK Seafood for white pepper crab and chili crab. All crabs were absolutely amazing, but I’ll be dreaming about that black pepper crab for awhile.

Our last night was great as we got to hang out with all of Alyssa’s friends for a birthday party. It was hosted a cool bar on the water that overlooks MBS. It was really fun pretending like we were locals. We had a very early flight, so we had to call the night pretty early at 9am.

As always with any good trip, I was definitely a bit sad to leave. Singapore turned out to be the perfect place to end a honeymoon and we had a great time there with old and new friends. We did have one more amazing meal as we went to a sushi bar in the Tokyo airport during our transit.

Perhaps it was fitting that we had some sushi on our way back as we’re planning our next trip to Japan and Korea. Sophia and I agreed that we should start planning that next trip so we have something to look forward to.

This trip was great in many ways for me personally. First I was just feeling really burnt out and needed to recharge my batteries. This trip did that. Secondly, the honeymoon went well and we mixed quite a bit of spending time together with exploring and socializing.

Although my only honeymoon may be over, I know that Sophia and I will have many more “honeymoons” in the future. We’ll continue to travel and explore the world. I don’t think the honeymoon phase will be over for us anytime soon.

Honeymoon recap part 4: finally the White Lotus portion

Sophia and I left Bangkok after 3 nights with mixed feelings. I love Bangkok but admittedly it lost a lot of it’s luster since the last time I visited. Sophia was just overwhelmed with such a crazy and hectic city. We were both really excited to start the cliche beach honeymoon portion of the trip.

Sophia had found Koh Lipe with some searching a few months ago. It was lauded as the Maldives of Thailand and everything I read confirmed that statement. Furthermore, it was a much smaller island that was less developed and the backpackers largely had not shown up yet. And lastly, there were some good dive sites so it seemed like the perfect location for us.

We were late to the game with booking hotels so options were slim unfortunately. Luckily, I had stumbled upon this new resort opening up with 0 reviews and only fake pictures of what the resort would look like. The resort would open December 15th so we would literally be there within 2 weeks of opening. It was a huge gamble, but they offered 50% off so Sophia and I said, fuck it let’s do it.

That ended up being possibly one of the best decisions we’ve made as a couple. After a flight from Bangkok to Hat Yai, then a 2 hour van ride to the pier, and another 1.5 hour boat ride to Koh Lipe, we made it to the island and the resort. I was riding a bit of a high as my Huskies just beat Texas in the Alamo Bowl so not much could ruin my excitement that day.

We got to the resort and Sophia and I both looked at each other and joked that this was giving us some serious White Lotus vibes. The staff had waited for our arrival and then sat us down with some drinks while they checked us in. After an orange juice and some coconut ice cream, we were escorted to our room which opened directly to the beach.

It was absolutely perfect. The resort and rooms looked exactly as the fake photos. We were both a bit surprised to see all this happening… it is Southeast Asia after all. Of course for a 2 week old resort, they still had a lot of things to work out such as the restaurant and the service, but for 50% off, we hit a gold mine.

Our 5 nights on the island was a magical time. We spent a lot of it doing well… not much. The island takes about 20 minutes to walk from the northern tip to the southern tip. And then there’s the western side which you can walk in 30 minutes, but there’s not much there besides some resorts. There was an amazing “walking street” that housed many restaurants and bars.

We spent a lot of the mornings sleeping in and enjoying our beachfront villa. At some point, we would take the 10 minute “stroll” into town to get massages and/or grab lunch. In the early evening, Sophia and I would start our nights at the local watering hole for a few cocktails, then grab dinner and more drinks. Rinse and repeat.

Notably on the food front, we had some amazing Thai style hot pot at Huamai Somtum along with some fire Esan style dishes. We found a favorite seafood joint at Ranee Thai which was a local spot next to the only “club” on the island. I also forced Sophia to come with me to find this lady named Mali who would go pick up some local fresh fish and serve it up sashimi style.

Mali was hilarious and it was a bit of a unique and rugged experience. Sophia dubbed it her first “Bourdain situation”. We sat in Mali’s “barber and beer” shop while Mali prepared some local fish sashimi style and fried one of the fishes. She sat with us for about 45 minutes entertaining us and cracking jokes. The food was amazing, especially the raw fish. It felt like this could be served a Michelin starred omakase restaurant. It was truly and experience I’ll never forget and I can’t wait to come back and find Mali again.

Our other notable activity was diving on the 2nd. Of course we had chosen to go diving on a very windy and choppy day. Sophia got seasick and I got close to joining her in throwing up off the side of the boat. It was less than ideal, but we got to dive and had a good time overall. We also got to partake in an engagement ceremony underwater. This Dutch couple in our group got engaged and it was a cool experience being able to watch it happen live. I had my GoPro and was able to play videographer for them.

We ended up becoming friends with Sebastian and Caroline and spent that night grabbing drinks with them. And then hung out with them again on our last night on the island. On our last night, we also met a Finnish couple at dinner who also joined us for drinks. It was an amazing way to cap off the island portion of our trip.

I was a bit sad to leave but after 5.5 full days on the beach, both Sophia and I were ready to get off the island. Overall, Koh Lipe was probably the best part of the entire honeymoon. We had a lot of alone time, but mixed it in with some good hangouts with others on the island as well. Sophia and I will always view Koh Lipe as a special place and we can’t wait to go back.

Tomorrow, I’ll write about the last leg of our trip in Singapore.

Honeymoon recap part 3: Bangkok dangerous

After my solo weekend in Hanoi, Sophia finally made it to Vietnam and my vacation high was in full swing. Obviously I was happy to see her and officially begin the honeymoon, but I was officially in vacation mode. I had no desire to check emails or do much work. I just wanted to explore with Sophia and focus on spending time together. It was a great feeling.

We landed in Bangkok on Tuesday afternoon and the lady at the hotel upgraded our rooms for us. Sophia and I decided to kickoff our time in Bangkok at a cocktail bar called Above Eleven. The bar was a multi-storied gorgeous rooftop and after Vietnam, we were ready for some decent cocktails.

After getting a bit loose at Above Eleven, we took a tuk-tuk to Khao Sanh Road. I hadn’t been to Khao Sanh since 2016 and was surprised to see how much it had changed. It seemed like the entire area got a facelift during the pandemic and I’m not sure if that’s a good thing as it lost it’s flavor as a backpackers’ paradise.

Perhaps it’s the fact that I’m 32 and past my backpacking phase, but we ended up going for a quick walk through and deciding to get out quickly. We ended up going to Yaowarat Road in Chinatown for some delicious street food and Sophia fell asleep on the tuk-tuk back home so we knew it was time to get out of there.

We spent basically the rest of our time in Bangkok doing typical tourist sites and eating. The next day, we hilarious got caught up in one of the tourist site “scams” where some locals try to trick you to go to another temple where a man conveniently is located to tell you about this amazing sale. I realized what was happening midway and stopped things before they sent us to the store. We weren’t happy, but it became a good joke for us the rest of the trip, so no harm no foul.

On our last day in Bangkok, we ended up visiting and exploring Talat Noi which was an awesome area that I had no previously been. It was rugged and meant to be a good area to visit to see what Bangkok was like before the skyscrapers.

We are great in Bangkok although Thai food isn’t Sophia’s favorite kind of cuisine. We ate some huge crabs at Ministry of Crab, went to a tasting menu at Samrub Thai, and slurped down 50 year old beef broth at a hole in the wall spot. Although the night market culture may be dying a bit, we had some awesome food at Jodd Fairs on our last night as well.

Overall, I would say that Bangkok was much less exciting for me the 3rd time around than it was the first and second. I suppose this makes sense, but I also believe it’s because I regularly eat a lot of amazing Thai dishes in San Francisco and New York already. It wasn’t like the first time I’ve eaten a spicy papaya salad before like 10 years prior.

Also, Sophia had a bit of a hard time in Bangkok. It was her first time in a major Asian city and I think the craziness was a lot to handle. It’s unlike New York where we lived where it’s largely a grid. Everything in Bangkok is 20-40 minutes away despite being seemingly close on a map and well there is a lot of unique things in Bangkok that was funny in your 20s, but just a bit sad now. I can see why she didn’t enjoy Bangkok as much.

I will say Bangkok probably is my 2nd favorite food city in the world right now behind New York. There’s such a variety of unique cuisines at all different kinds of price levels. For that reason alone, I’ll likely make a stop to Bangkok every time I’m in the area.

After 3 nights and 2.5 days exploring in Bangkok, we got up at 4am to start our journey to Koh Lipe which is a small island in the south of Thailand. More on that tomorrow.

Honeymoon recap part 2: 36 hours in Hanoi

After a day in a half in Hanoi, I had started to feel settled in. I had a good night hanging out with some folks I met at a bar, and my mind was shifted to vacation mode. I woke up on Christmas Day well rested after going to bed early. I took the morning to pack up and upgrade hotels.

Once again, I got Vietnam’d as the first hotel I booked ended up pulling a bait and switch and putting me in a sister hotel. The hotel wasn’t awful by any means, but it wasn’t what we paid for and it left a sour taste in my mouth. I ended up switching to the Oriental Suites where I was taken care of by Mike and Bella. This was probably the 6th hotel I’ve stayed at in Hanoi and was by far the best, especially considering the price. I was stoked.

Mike ended up booking me a private car to Ninh Binh and also recommended me an awesome Bun Ca joint while I waited. Sophia and I had originally booked two nights in Ninh Binh, but I canceled as her trip would be delayed. I ended up spending my Christmas Day riding around Ninh Binh on a motorbike and exploring the area. It was amazing day all around - I hiked up to the top of the famous “cave” and had some amazing sights over the mountains and valleys.

I got back to Hanoi in the evening and met up with Timmy for some drinks. I felt bad as he was waiting for me at our local pub for a couple hours as my driver fought through Christmas Day traffic everywhere in Hanoi. Later that night, Sophia finally arrived in Hanoi and my guy Mike at the Oriental Suites set-up a corny but sweet flower bed in the room for her arrival. Both Sophia and I were relieved that she had finally made it - after almost about 30 hours of traveling.

On our only full day in Hanoi together, we ended up exploring all the sights that Hanoi had to offer and ate everything along the way. The highlight of the afternoon may have been our meal at the Bun Cha restaurant that Obama and Bourdan ate at. I had gone the last time I was in Hanoi and it was just as good.

We had a great night on the rooftop bar for cocktails and got a bowl of Bun Bo Hue for dinner. After a couple drinks on beer street, Sophia’s jet lagged caught up and we called it an early night.

The next morning we got perhaps one of the highlight meals of the trip in a bowl of Pho Bo in the Old Quarter. It was my first time there and Sophia had found the spot on Tik-tok. I’ve always maintained that the Pho in San Francisco is as good or better than the pho in Vietnam unfortunately, but this bowl of Pho was amazing and made me rethink my statement.

After getting some Banh Mi’s for the road, we wrapped up our 36 hours together in Hanoi and headed for Bangkok for the 2nd leg of our trip. It was a short, but good time together. Overall, I love Vietnam and I enjoyed my 2nd time in Hanoi. I may not be too enthusiastic to make a 3rd trip anytime soon as there’s other parts of the country I have yet to explore such as Hoi An and Hue.

Perhaps next time around, we’ll start in the south and make our way north.

Wrapping up 2022 and my honeymoon

2022 was both an amazing and horrible one. I celebrated some amazing personal things in my life which included my wedding. But I also went through the most difficult year of work in my professional career. I don’t really have much else to say or write about 2022 but that we’ll call it a wash year and I’m ready for 2023.

After a great couple of weeks in Asia, I made it back home yesterday and went back to the office for the first time in a month. I had thought I wanted to write more during my trip, but I quickly realized that I just wanted to be as far away from my laptop as possible. It was a much needed detox from work. Instead I’ve decided to take the next few posts to recap my trip and write down things that happened. I’ll start today with the first leg of my trip.

My trip to Asia got off to a rocky start as Sophia had to meet me in Hanoi a few days late. I ended up spending the weekend in Hanoi by myself and made the best of the situation. It wasn’t ideal but it was this weekend when I rediscovered the beauty solo travel.

I spent Christmas Eve in Hanoi exploring the city, relaxing and reading at multiple cafes, and stopping at every restaurant that looked good. I’ve seen most of Hanoi so I wanted to spend some time in West Lake where the expats hang out and seeing parts of the city I had yet to explore.

I walked from the Old Quarter all the way to Westlake and then rented an awful kids bike to bike around Westlake. The immediate lake area was filled with various cafes and restaurant. I stopped at a few at various points for a coffee or beer break. Overall it was a good activity, but I got bored a bit quickly as a small coffee shop on a lake only gets so special.

After a long morning and early afternoon, I ended up at a sports bar by my hotel where I met an English guy named Timmy who was also traveling in Hanoi solo. We shared a love for sprots and got a long quickly. It was a serendipitous situation as I think we both came back to the bar to hopefully meet others. We ended up drinking together for the next 5 hours and then met the next day for drinks again.

Meeting Timmy reminded me of the good ole days of backpacking SE Asia. Some of my best memories from traveling was meeting strangers from all over the world. Candidly, it was a bit of a relief that I was able to meet friends traveling solo. I had thought that part of my life was potentially over once I gave up backpacking and staying in hostels.

It was a great feeling that I found the magic of travel on day 2 of my trip.

Vacation mode enabled

Hello from Hanoi, Vietnam. I’m on my 3rd day here and I’m happy to say I’m finally settling into vacation mode. It always takes me a couple days to try to switch my brain off from the hustle and bustle of work.

For me, it’s a big mindset shift… going from moving and trying to get as much stuff done as fast as possible to relaxing and just enjoying doing nothing. For that reason, I’m glad I’m taking a much longer vacation where I’m able to take some days to adjust.

The current book I’m reading is “The Order of Time” by Carlo Rovelli. The book gained a bit of popularity on FinTwit and I heard about it when a few people tweeted out about how much their minds were blown after reading it.

I’m about a quarter of the way through and I am starting to have my mind blown. It’s one of those books where you just have to read it to truly understand it. The beginning of the book talks a lot about how time isn’t linear or as we think of it.

Most notably, it’s been proven that time moves faster in the mountains or when you’re in movement. Someone who is sitting still notices that time moves slower and someone who is moving notices that time moves faster.

My big take away after reading those chapters yesterday is that my life is moving a big too fast. I am constantly on the move - looking for the next thing to do. My life (or perception) of life is moving faster than others. That’s not always a good thing.

Making the best out of a shit situation

I wrote yesterday that I felt like I couldn’t catch a break in 2022. With Sophia attending a funeral in Baltimore at the beginning of our planned honeymoon, 2022 had one more surprise for me.

Sophia is headed off to Baltimore tomorrow morning to attend her friend’s father’s funeral. I decided to keep my flight and fly out to Vietnam by myself. I had thought about pushing things back, but it was going to cost me quite a bit of money and I had some nonrefundable hotels booked already. Sophia will end up getting in Sunday night so that leaves me 3 days alone in Hanoi.

Obviously this is not an ideal scenario. The timing was really poor for our trip and I was really excited to travel with Sophia for her first trip back to Asia since she came here after she was born. While this isn’t the ideal start to my honeymoon, I also realize that things could have been a lot worse.

We’re still headed to Southeast Asia and we’re going to have an amazing time there. We’ll still get to go to all the major sites we have planned.

For myself, I’ve traveled solo quite a bit before and this is another opportunity to get out of my comfort zone and make the best out of my time solo in Vietnam. I’m not exactly sure what I’ll do, but it’ll probably be a lot of eating amazing food and exploring. There may be no better place to be traveling solo than Vietnam so I am excited.

I couldn’t help but think about how this may be the story of 2022. It’s been a tough year... one where most of us wouldn’t have wanted at the beginning of the year. But at the end of the day, we may look back on 2022 as a period of growth and resilience. Who knows? We may look back at 2022 and realize that it was a great year after all.

Can't catch a break in 2022

I feel like the story of my year is that I can’t catch a break. I know that’s not completely true of course - I had an amazing wedding and celebrated some great things in my life.

But unfortunately, 2022 has been rough especially when it comes to my trips. We were supposed to leave tomorrow night for my honeymoon and Sophia unfortunately got some bad news when she found out today that her best friend’s father passed away. It was tragic news and very unexpected.

Between catching COVID during my trip to Spain, to Sophia catching COVID before our Hawaii trip, and now this terrible situation… I can say that I’m ready for 2022 to end.

Unfortunately these things happen in life. I’m hoping 2023 brings better days for us.

Year-end financial review

I took a bit of time over the weekend to finish up my year-end financial review. I’ll usually do at minimum a complete personal financial review every quarter, but the year-end one takes a bit more time given the tax planning opportunities.

This year, I have a financial advisor who takes care of my portfolio and rebalancing for me so that saves me a bit of time on most of my portfolio. There is still more work to be done though as I have other accounts including crypto that I’ll need to review.

I think most people miss out quite a bit on a lot of opportunities due to a lack of planning. Financial planning takes discipline and effort. I admittedly hate doing it every quarter, but I know the impact it can have on my financial life. My tax loss harvesting this year will alone save me a few thousand dollars in additional taxes.

For those that are not in the know well enough to manage your own finances, I highly recommend finding quality financial and tax advisors that are proactive planners. Unfortunately there’s a lot of low quality advisors out there, but the good ones are worth their weight in gold.

Weekend work

I just got my eyes dilated and I’m just starting to be able to see within a yard again. Not sure why I agreed to do this during the workday, but looks like I’m going to be doing a lot of weekend work to catch up for the time missed today.

I saw a tweet today where a founder was looking to recruit for his startup. One of the requirements was that his company works 6 days a week in office in San Francisco. It was a pretty interesting tweet thread as half the responses was basically telling him he’s a joke and the other half was applauding him for wanting to build something special.

My thoughts are that while this company isn’t for everyone, I think it’s pretty cool and can be a great company. He’s recruiting a specific type of person which most won’t qualify for and that’s okay. With that said, I do wonder how sustainable a model like this is. You can only work so much in life and burnout is a real possibility.

Regardless, anyone that’s worked in a high growth startup will eventually have to work weekends at least sometimes. It sucks but it’s part of the gig. You can’t really just shut it off for an entire 2 days and sometimes you just have to get caught up.

Better days ahead?

As we wrap up 2022, people’s attentions have naturally start turning to 2023 predictions. A new year brings new hope and after 2022, we all could use a fresh start. I’ve heard everything from 2023 will be a soft landing and rebound year to that we’re in for a recession worse than 2009.

No one knows for sure what will happen. My personal take on the situation is that we’ll likely be in a recession and economic slowdown in 2023. Companies will greatly retract spending due to the downturn and we’ll see a ripple effect throughout the entire economy.

The market will not rebound like we hope, but it’ll settle down and volatility will lower. We’ll start to see glimmers of hope in 2023 and comparable/multiples will likely start working their way back to the median ranges.

It’ll likely be another challenging year for startups, especially in the first half. Downrounds and bankruptcies will dominate headlines in Q1 and Q2. But I also expect VC funding and secondary market to open up more in 2023 compared to 2022.

While I may sound pessimistic, I actually believe there’s going to be a lot of opportunity in 2023. I’m excited for that and a downmarket won’t deter me from chasing those opportunities.

Reflections

I had a big reflection and realization yesterday. I was reviewing my H2 2022 plans as we close out the year to try to find areas where I missed, and I had realized that I wasn’t exactly eating what I was cooking for most of the last quarter.

One of my big initiatives in H2 2022 was to ignore the market noise and focus on what we can control. The plan was spot on as we can’t control the macroeconomic environment. But the problem was my execution of the plan.

I had come to realize that I was often speaking about the market and talking about “when things settle” all the time. I would start our team meetings with an update on the situation and plan for the weeks ahead based on the market vibe.

So one day I was saying, focus on our goals and initiatives and ignore the market, then the next I’d start the meeting talking about the market!

It seems so silly, but it definitely impacted my personal mentally and my team’s as well as we would succumb to the market volatility and let that dictate our moods. Our focus ultimately should be on grinding towards our goals regardless of what happens on the outside.

It wasn’t a healthy mindset and I plan on changing that going into next year.

The more important things in life

There was awful news this morning as the sports world has learned of Mike Leach passing this morning after a heart attack. Mike Leach was one of the most interesting and genuine figures in college football. I’ll always remember his silly but honest post-game interviews - his life advice during halftime was something I’ll miss. At only 61, he left the world too soon.

Most of the world, including myself, has never met Mike Leach personally. Yet, his sudden death still resonates with most of the sports world today. His impact was far reaching even beyond the the players and coaches that he worked with during his career.

Coach Leach’s death is another great reminder of what’s important in life. No one is going to remember the job you had or the investment that you made. Rather, they’re going to remember how you impacted their lives. It’s good to remind ourselves of this from time to time.

Dire times for early stage

Startups are always going to be risky. The majority of early stage startups never find product-market fit and end up shutting down before they ever get the chance to get started. The statistical risk of bankruptcy goes down with each successive funding round.

Of course during a down market like right now, the companies at the biggest risk of not making it out will be the earlier stage companies. I’ve been speaking to a lot of investors lately to get a pulse on the market and they say the situation is dire.

They’re busy in all the wrong ways right now. Many of the VCs I spoke to said that many of their portfolio companies are months and sometimes weeks away from going bankrupt. Many are looking for emergency debt right now to stay afloat. One investor I mentioned said that he was called twice on Sunday from two different startups desperate for some capital to stay afloat.

We’re probably not going to hear about a lot of these companies in the mainstream tech media. Early stage startups that have yet to make a major dent typically do not get a lot of media coverage.

Regardless, this is yet another domino that will fall in this down market. Unfortunately I think there’s going to be a lot of these startups who do not make it out of this “recession”. I expect things to be pretty brutal in 2023. All of us working in tech should brace ourselves.

The best offense is defense?

I’m free! That is my flu symptoms are officially gone and I can start being a normal human being again. It was rough to get sick immediately after my wedding, but I suppose at least it happened after.

I watched the Brazil vs Croatia game this morning while going through my morning inbox. It was fascinating to watch as it was clearly Brazil’s game to lose the entire way through. Croatia knew they had no chance of keeping up with Brazil if they played into their hands, so Croatia decided to basically hole up on the defensive side and do everything possible to get to penalty kicks.

The strategy was working as they went into extra time and it seemed like this would be headed for penalties. Neymar for Brazil eventually broke through and scored a gorgeous goal which seemed like this would doom Croatia. Pretty much everyone including myself thought the game was over until somehow Croatia got a goal. That was their only 1 shot on target the entire match.

The match went to penalty kicks and Croatia was able to pull it off. Their strategy had worked beautifully to beat a much more talented and better Brazilian team. It was a fascinating game to watch as someone who doesn’t watch much soccer. I suppose it would be the equivalent of a bad football team trying to control the clock the entire game.

I love drawing sports parallels to business and I couldn’t help but think how Croatia’s strategy could be translated to today’s business world. As much as I’d like to be aggressive all the time, perhaps the market is signaling that we all need to pull a Croatia and play defense for now. Let’s bend, not break and live long enough to get us to our opportunities that lie ahead. Anything can happen if we make it to penalty kicks.