Unplugging

I played 18 today at Gran Coyote. It was a great first experience doing the resort golf thing. The course was brutally difficult. There wasn’t much forgiveness off the tee… no other fairways to hit into. Once you slice or push right, you’re gone. My irons and putting were on point. Unfortunately I completely forgot how to drive the ball and was fighting an awful slice all day. It was frustrating and I wasn’t able to fix it on the range after.

Of course tomorrow I’m going to pick my driver back up and my irons will be all over the place. That’s golf I guess.

On another note, I’m preparing to take a week and half off starting this upcoming Wednesday. I’m already starting to think about which meetings I can take and which I won’t. I just realized today that I’ve completely forgot how to unplug which is obviously a terrible thing.

I think the combination of the pandemic, lack of vacation time and work demand being through the roof has really changed how I view work-life balance. I suspect a lot of other people are in the same boat. This likely doesn’t bode well for us as a society.

Being in Mexico has really opened my eyes a bit. There’s much more of a work to live type feel here, especially being in Playa. I’ll need to find balance again and it starts with my vacation this upcoming week.

Startup karma

On Tuesday, I wrote about what happens when things seem to never go well in startup world. Admittedly it was a tough start to the week and been a tough month overall.

Of course, this seldom last long and fortunes seemed to turn starting yesterday for us. Good news after good news started piling in for us on seemingly every front yesterday. Maybe there is such thing as start-up karma.

There are so many ups and downs in the startup world, but things move fast, really freakin’ fast. One day you can be down in the dumps and the next will have you jumping for joy.

I’m really excited for the rest of this week and next. I’ll be heading out to take time off on Wednesday, but there’s a lot I want to accomplish in the next coming week until I do.

Tax (or not) the rich?

The news article of the past 24 hours was the leaked taxes of billionaires which showed that they do not pay much in taxes. This is not news to anyone with a background in taxes or finance but of course, it’s an eye popping headline that has gone viral.

As part of this news report, many news outlets and reporters have taken this information and started publishing a “True Tax Rate”.

I want to be clear in that this is misinformation and misleading. What these 4 billionaires have in common is their appreciation in wealth is due to appreciation in stock which is not taxed until you actually sell that stock. Effectively, what people are arguing by reposting this is that we should be taxing people on their unrealized gains in stock. This is a tax policy (aka mark-to-market) that makes no sense.

You don’t realize any cash until the sale. Why should you be taxed on something you haven’t locked in? If we wanted this policy, we’d also have to apply it to homes and real estate. No one should be taxed on appreciation of their home prior to selling it.

Now before people come after me, I’ll address the elephant in the room that I am in favor of taxing the rich. I simply just believe in effective tax policy that encourages behavior rather than adding more patches on the sinking ship that is the tax code.

So what is my solution if I don’t believe in taxing unrealized gains? Surprisingly, I believe in a wealth tax. Albeit, one that makes more sense and encourages good behavior.

I would love to see a wealth tax imposed on the ultra wealthy that allows the ultra wealthy to avoid this tax by deploying their capital into charitable organizations. Let’s say we implement a 1% wealth tax on those 4 billionaires above. Warren/Jeff/Mike/Elon would be able to avoid this 1% wealth tax by donating 1% of their wealth to charitable causes instead.

If they don’t believe in the government allocating their capital correctly, then they can choose to pick who can. Even the staunches supporters of capitalism can get behind this. The idea of capitalism is to deploy capital and well we’re encouraging that with this wealth tax.

When things don't go well...

The last month and some change have been challenging. It’s just been one of those stretches where it feels like not much is going our way.

A mistake here, a missed opportunity there, deals lost, candidates declining your offer, the list goes on. In truth, this stuff happens all the damn time all year long in the startup world. For some months, it just happens more than the wins. This past month has just been one of those months.

I’m frustrated by this. Like many other builders, I set a high standard for myself, the organization and the goals. I too want record breaking month after record breaking month in a graph that just goes to the top right.

Of course, this is not what happens in practice. There are many bumps in the road and often times the most successful startups I’ve seen have had prolonged stretches of this.

It’s been a frustrating 24 hours especially as a few things in particular have been bothering me. At the end of the day, I need to remind myself of the following:

We are growing like crazy and have some amazing projects in the works.

We do have an amazing team that is smart, dedicated and hungry.

We are having a record breaking year. A bad 30 days does not define the year.

And despite a tough last month, we can still be on a graph that goes to the top right.

June in Playa

I’ve been so shitty at writing daily the past few months and I don’t feel great about it. I think I’ll make it my half year resolution to make more time for it and start writing first thing in the morning.

For now, I’m set-up in Playa del Carmen for the month of June with Sophia and my friend Alyssa from high school. It was a crazy decision that we thought was too good to pass up. We’ve got a gorgeous condo with a rooftop pool, deck, bar and 3 bedrooms. My rent isn’t that far off than my San Francisco rent and cost of living is significantly lower.

The food has been fantastic so far. I’ve eaten tacos and seafood pretty much for every meal over the last 5 days or so. A ceviche lunch sits really well within my diet. Delicious protein with no carbs. We’ll see how I feel about the food in a week or two. I’m already starting to crave Asian food and variety.

Work has been pretty good. I’ve got a good set-up on the top floor and alternate between the deck and the air conditioned kitchenette. I haven’t had too many hiccups getting work done despite being in paradise.

I’ve joked that I don’t think I’ll ever want to leave here and I just want to work remotely from here forever. Of course, I’d imagine that by the end of the month I’ll be itching to get back to SF or NY, but we’ll see.

Show me the money

I’m feeling great today. Slept the best I have in over a week and I feel rested headed into my last weekend in New York. Hoping to continue that trend through the weekend and next week in Mexico.

On the public markets - meme stocks are going crazy again and I’m at the point where I don’t think they’re going away anytime soon. Retail investors have money and they are bored at home. Just when we thought the market was headed for a correction….

I won’t be surprised to see crypto activity pick back up again shortly. Money is plentiful right now and putting are looking to put it to work.

In the private markets, I can’t imagine a better time to ever start a business. Angels, VCs, and celebrities are throwing money at companies right now. My daily newsletters highlighting new funding rounds is getting longer and longer by the day. This is across all industries and sectors.

For myself, after making a sizable angel investment and investing in my girlfriend (now fiances), I am a bit cash poor and admittedly have a bit of FOMO from missing out on the dip. This may be fortuitous in the long run. Time will tell.

The fix to my experiment?

Yesterday I wrote a 2 month update on my west coast hours living on the east coast experiment. Last night, I had trouble sleeping (again) after trying to go to bed early and ended up falling asleep after a couple hours of laying in bed. This morning, I woke up at close to 10am and felt the best I have all week. I ended up sleeping over 8 hours still.

It kind of hit me then and there on perhaps why my experiment hasn’t been as successful: I’ve been trying to force things too much. One of the benefits of working west coast hours was to get more sleep and go to bed later — well I’ve realized I’ve been trying to go to bed earlier in order to wake up earlier. It’s a silly realization that for this to be successful, I’ll need to just let things happen a bit more naturally. Let me body decide when to go to bed and wake up.

During my last week in New York and the next month in Playa del Carmen, I’m planning on just going with the flow. If I need to stay up later, I’ll stay up later and go to bed when I want. I’ll wake up when I want (within reason) and try not to force the gym sessions and activities in the morning.

This experiment was about finding my ideal sleep/work/leisure schedule and all I’ve been doing is trying to shift my sleep/work/leisure schedule around rather than letting my body decide.

We’ll see how it goes.

The west coast hours on east coast experiment - 2 month update

For almost two months, I’ve been living in New York City while attempting to work west coast hours. My hope for this experiment was to shift hours to a schedule that what I believe is my natural preferred work hours. I wrote about my experiment last month at my one month check-in. Last month, I wrote that it was a mixed bag of results which some nice things, but some not great aspects. Unfortunately, things maybe have gotten worse since then.

Here’s some of my notes and thoughts on some of the aspects that I was hoping would improve with this experiment.

Sleep - By far my biggest disappointment has been related to sleep. I was hoping that I would be able to sleep better at night, wake up to no alarm clock, and be much more energized throughout the day. It’s almost been the opposite effect despite the fact that I am a night owl. I tend up to stay up later due to work and I don’t get time to wind down before bed. Because of that, I’ve taken much longer to go to bed than usual. I haven’t been able to sleep in as well on the mornings - yes there have been a few mornings where I wake up feeling great, but it’s been so inconsistent that I am typically feeling worse on a day to day basis.

Exercise - Probably the best part of working west coast hours is that I get to go to the gym in the morning. It’s really nice being able to wake up, get a sweat in and go to work uninterrupted but I also feel slightly less energetic in the mornings. While more consistent, my work outs feel less impactful.

Work hours - This is something that I knew was going to be a challenge and it has been a struggle. I’ve been pretty good at blocking off my mornings, but occasionally I’ll have a meeting during my mornings that I was supposed to have off. That of course expands my work day. Furthermore, working through the evenings have been anything but enjoyable. My best hours to get stuff done is typically between 6pm-9pm. What I found is that it’s perhaps not the hours that make it my most productive, but the fact that there’s less distractions during those hours. It’s been tough working until 9-10pm every day.

Given that it’s largely been a negative experience for myself, I’m not ready to throw in the towel just yet. I have a theory that a lot of these issues could just be stemming from the fact that my life has been insanely busy in New York and I’ve just been exhausted overall since I got here two months ago.

I’m excited to continue the experiment in Playa del Carmen where things are hopefully a bit more relaxing than New York. Perhaps that’s when the true productivity is going to come from this experiment.

I proposed and now have a fiance

I proposed to Sophia on Saturday after 3 years of dating. It’s still a bit of a surreal feeling that I’m engaged to the love of my life. She’s an amazing girl and I’m truly lucky to be her fiance.

I had planned on picking up he ring during our two month New York trip but I wasn’t sure when or where I was going to pull the trigger. I ended up deciding that New York was perfect place to propose and set plans in motion.

I was lucky to have a friend bring me to his diamond guy which ended up being a great experience. The diamond district in New York is a trip. I’m not sure if I’d go as far to say I liked going there, but it was an experience I’m glad I had. It took me a couple trips to pick up the diamond I wanted. Ultimately, the first diamond she brought out ended up being the winner - it’s the first one that caught my eye and it was perfect.

My two best friends were in town with their significant others to “celebrate a birthday". We turned her birthday weekend to our engagement weekend.

I decided to get on one knee on my roof of our apartment that we’re staying it. It ended up working perfectly. It had great views and we had the roof to ourselves. I even had two friends hiding in the pool area taking photos. We had some great pictures and a video from the proposal.

Sophia had known that it was likely to happen that day all along. There wasn’t one give away but she put everything happening together and it was just too perfect of a weekend to get it done. We had some funny moments to discuss afterwards.

We ended up partying all day and I booked Pera in Soho for about 20 of us to hang out. COVID restrictions made us sit the entire two hours, but we played a bit of musical chairs to hang out with each other. I ended up surprising Sophia with some of her friends who came to town. It was a blast and I’m glad Sophia got to celebrate with her friends.

I don’t think there’s many good reasons to stay out as late as we did at our age, but I suppose my engagement should be one of them. As I write this on Monday at 9:30pm, I’m halfway asleep and today was a struggle.

I’m looking forward to catching up some sleep and enjoying my last week in New York. I’m even more excited to get to Mexico where I’m hoping to catch up on a lot of rest and relaxation. NY has been great, but I feel like I’m 2 months of sleep behind.

The shit part(s) about New York

I golfed with an old friend of mine and one of his friends this past weekend perhaps for my last time during my short 2 month stint in New York. Both are from California like myself and naturally we talked a lot about living in New York.

I’ve written a lot about how amazing the city can be at times. The people, the energy and drive is unparalleled anywhere in the world. You have to be a pretty boring person to be bored in New York City. I’m convinced of that.

Of course, it’s not always rosey living out here. Everything just feels a lot harder often.

Getting out to a golf course is at least an unrelaxing hour away. Even hitting the driving range at Chelsea Piers becomes a 2 hour chore. Finding nature and getting out the hustle and bustle is a huge pain and perhaps many trains away.

While the abundance of restaurants is amazing and no one can deny NY is the food center of the world, finding a reservation on a Friday or Saturday night becomes a whole ordeal if you didn’t plan weeks in advance.

Perhaps the most tolling part about the city is the exhaustion. Whenever people ask me about my life in SF versus NY, I always mention that my quality of life is way better in SF but my excitement level is much lower. I sleep more, I relax more, I’m out in nature more, but of course there’s much less to do on a day to day basis.

I’ve really enjoyed my time out here for the past 6 weeks and I’m looking forward to enjoying my last 2 weeks here, but I’m also ready for a change of pace. I miss the chill west coast right about now.

Life, death and taxes

It’s a gorgeous day in New York today. These types of days don’t happen too often here. It’s almost always too hot or too cold, but today is absolutely perfect with just under 80 degree weather.

I also filed my taxes today given the IRS extended the filing deadline to May 17th. My plan of taking my tax bill and investing it for another month backfired as the market decided to take a dump over the last couple of weeks. Thanks IRS!

I always find it really funny when people start to make enough money to start owing taxes versus getting a refund. Every year I get texts from my friends wondering why they have to pay taxes this year compared to last year when they got money back. It’s a complete shock to them and they’re always disappointed when they realize that this is the new norm for them.

I remember when I was working at PwC doing taxes for hedge funds and private equity firms, I sat next to a girl who started in my class. I’m pretty sure she got the job solely because her dad was an alumni of the firm and knew the right people. This job was not her calling and she barely understood a thing about taxes. Her dad did her taxes and sent her the return. She immediately started crying as she was wondering why she wasn’t getting a big refund that year.

I had to explain to her that she moved to NYC and taxes were higher and the firm withheld just enough to cover her tax bill which meant she wasn’t getting anything back. She told me that she had gone shopping and ran up a bill on her credit card expecting to pay it off with her refund.

She was “coached out” of the job a month later.

Crypto adoption

The news of the last 24 hours or so has been Elon Musk announcing that Tesla would stop accepting bitcoin as payments for Tesla cars due to environmental reasons.

Just a month or so ago, crypto heads were rejoicing when Elon announced that Tesla would buy $1b worth of bitcoin and allow payment for cars with bitcoin. Many other companies and firms followed suit.

Yes Elon’s word isn’t the bible but this is undoubtedly big news and a major setback for crypto adoption just when everyone seemingly has turned the corner on bitcoin.

Everyone seemed like they were on the crypto train the last few months after a decade of resistance. It was a much slower adoption than even the modest cyrpto heads would have thought during the 2010s.

So far, it seems like the 2021 is going to be crypto’s year. I still believe that to be true despite what Elon or Tesla believes about bitcoin. New technology is always met with skepticism. There’s going to be more bumps in the road and setbacks this year and in the years to come.

I’m not sure bitcoin will completely eliminate fiat currency, but I do know it’s here to stay.

Tech pullback?

I’m writing this on the Amtrak back to New York. There’s something soothing about trains that I miss. It’s not crowded, it’s comfortable and the wifi is pretty darn reliable. I always get a lot of work done on train rides. Perhaps it’s as simple as not having calls - I’ve got too many of those nowadays.

Markets are trending towards a tech pullback as people seem to be shifting towards safer investments such as the S&P 500. We’ll see if this continues over the coming weeks.

Corrections are healthy and create some great buying opportunities. I still have a heavily weighted portfolio towards tech and plan to keep it that way. With all that said, I’ll be playing a bit more defensive over the next coming months. I’ll be looking to trim some of my outsized positions due to gains and look to diversify my portfolio a bit more away from tech.

There’s a lot of names that are tempting out there for me including $RBLX and $CPNG and $PATH among many others. These recent IPO stocks will likely have some better buying opportunities in the future so I’ll wait patiently in this market. I know there’s a lot of nervous folk out there and it’s best to play it safe given the last year’s gains.

Vaxed

I got my second shot of the vaccine yesterday evening. I’ve gotten the Moderna vax and most people I speak to say that the side effects especially on the second dose could be tough for 1-2 days.

I woke up this morning achy, tired, and had slight chills. After sleeping a few more hours, I woke up somewhat okay. I’ve been achey and have a minor headache but so far so good 24 hours in. I’m glad that I didn’t have much of a fever. I know I’m a bit lucky here as I have some friends who were bed-ridden for at least 24 hours due to the second shot.

It’s pretty amazing how fast we got the vaccine up and going. The original predictions for a COVID-19 vaccine were 2-3 years away from some. We got it done in under a year.

I’m really excited to be vaxed and ready to put COVID-19 behind me. It’s going to be interesting for a few months I’d imagine as we open up, but I’m ready to travel and see people again. Let the roaring 20s begin.

Goodbye Alteryx, my first 10x'er

Today I sold off the vast majority of my position in Alteryx. While it’s not the first stock I’ve bought in my life, it’s my first highly success stock. I first got interested in Alteryx when I started using the software in 2015 during my time at PwC. Within 10 minutes, I knew the software could be game changing for many use cases.

The company went public in 2017 and I immediately bought the stock as a heavy user of the software at under $15. I bought and sold many more shares in the the last 4 years. I sold a large chunk last year at $157 to trim my heavily appreciated position. It was my first 10-bagger stock.

The company has gone through some rough times over the last year and half. Slowing growth rates and a reluctance from leadership to shift to the cloud has been the biggest contributors to the stock sitting at under $100 for the last few months.

I still believe in the value prop of the software but I do think the company has a bit of ways to go as it makes a shift to the cloud until I buy back in. There is a big leadership change at the top and the company may be at a pivotal point. For that reason, I decided to sell off most of my position. I held onto a few shares for sentimental reasons and for a reason to keep track of the company’s progress.

Goodbye for now Alteryx. You’ve been great to me.

Secfi New York City

Today I signed a short-term lease in a co-working space in the Flat Iron in NYC. We had been thinking about opening up an “office” in New York for some time and decided to pull the trigger while I am out here. Candidly, I had no idea that we would doing so when I decided to come out here for April and May, but it made too much sense for us.

New York is very much in between San Francisco and Amsterdam where our other two offices are. It’s a great spot in the middle of the two cities to fly to and meet when we need. We have some key partners in New York as well. Last and but not least, there is a lot of great talent out here in New York that would be hesitant to move to San Francisco. It just made sense to get an office out here.

We got a great spot in “Silicon Alley” aka the Flat Iron district. The co-working space is great as it’s catered towards Fintech startups and investors. I feel right at home here and am happy to call set-up shop here until it makes sense to get our own space somewhere else.

NYC Golf Bus

I played 18 at Van Cortland today in the Bronx. It’s not the nicest course, but it’s a fun one and probably one of the easiest courses to get to from Manhattan. Apparently it’s the oldest public course in the country.

I’ve been enjoying my time out in New York but getting out to the golf course is really difficult. Everything is at least an hour away by train. Ubering to a course isn’t an economical option.

I feel like there is a good business opportunity somewhere in this space. There’s a lot of folks who live in Manhattan that love to golf but complain about the inconvenience of it.

I know people like myself would gladly pay a bit of a premium for some sort of service to take me to golf courses within the area. I’d imagine it would be like an airport shuttle.

Biden Tax Plan

I see a lot of people freakin’ out about Biden’s proposed tax plan both on the corporate tax rate proposal as well as the capital gain rate proposal. I think the big thing is that everyone needs to calm down a bit and let things play out.

Proposal does not mean policy. I have a hard time seeing Biden getting his way with increasing the corporate tax rate to 28% and nearly doubling the highest capital gain rates. It’s likely a negotiation chip as he goes to a very divided Congress about these issues.

Furthermore, even if the proposals did go into effect, we will all have time to plan around it.

I have friends who are panic selling to lock in long-term capital gains. This is a severe overreaction at this point and likely will result in worse consequences for the individual.

Everyone needs to relax a bit and let things play out. These things take time and reacting to a proposal that is far from policy is not a great strategy for anyone.

West coast hours on east coast

I got absolutely whacked by work and calls last week and I’m mad at myself for not making the time to write. I started this blog to write daily to improve my writing, keep track of my thoughts and provide a therapeutic outlet. I failed last week, but hoping to learn from it.

I’m almost an entire month in my time in New York. It’s been a jam packed trip and I felt like today was the first Sunday where I wasn’t absolutely floored and exhausted. It feels good.

My experiment of working west coast hours on the east coast has been a mixed bag. Admittedly it has been a lot more difficult than I was anticipating and I don’t believe I have been as productive.

On the positive side, I have been working out on a more regular basis. I have steadily been going to the gym and workout classes 4-5 days a week and it feels great. I feel the healthiest I’ve been in awhile.

Unfortunately, I haven’t been able to get in a great routine of sleep. The thought of waking up with no alarm clock has been difficult as I’ve either needed to sleep in late resulting in me scrambling to get going in the mornings. That’s been the most unfortunate part that I was hoping would be better. I’m hoping to get on a more regular schedule, but I haven’t been able to.

From a work standpoint, it’s been difficult with meetings/calls and a typical east coast schedule. My lunch and dinner hours vary greatly which affects my mood quite a bit. The worst part has been working late until 10pm or later to make up for lost time. Both Sophia and I are struggling a bit with this part.

I’m going to continue the experiment for a couple more weeks and see if it improves with a better schedule. If it doesn’t, I’m just going to shift to working an east coast schedule to start to normalize my schedule.

The Super League

I’m not the biggest soccer fan, but I found the Super League stuff to be really fascinating. If you haven’t heard, the top 12 teams in Europe have decided to branch out and start a Super League. These 12 teams include the household names when you think of club soccer. They are the cream of the crop and the ones who have the most money, the best players, the most fans, etc.

So why would the top 12 teams set out and look to go against tradition and create a Super League? Money.

The clubs have enough power to launch their own league generating far more revenue for themselves as clubs individually. By pitting the best teams against the best teams every week, there will be much more revenue at play to be shared amongst the top teams.

Most fans from what I’ve read are completely against this idea of a Super League. They think that it’s going to ruin football as we know it and as a limited soccer fan, I would tend to agree.

We’re not far from a Super League forming in college football where the teams with the most money and revenue will look to create a Super League. We were close many years ago when the Pac-12 was close to merging with the Big-12 to create a super league.

I know there are a lot of passionate fans out there very upset about this soccer Super League and many who legitimately think this will ruin soccer. I feel similarly when considering a Super League for college football.

Unfortunately, I think that money will ultimately win out here. The rich will get richer and tradition will go out the window when money is on the table.

I hope I’m wrong, but I know how things go when there’s this much money at stake.