Culture at work

I saw this video last night and thought it was a fantastic display of culture at work.

I believe that there’s a lot to learn from sports in the world of business and vice versa of course. Some may see a student athlete picking up a trash can that’s been knocked over, but I see a leader standing up during a time of adversity and leading by example.

Your culture as a team or company shows up during times of adversity. Following a tough loss, this student athlete made a statement that this is inexcusable and he was going to fix it. That’s culture at work. It’s no surprise that Houston has been a fantastic team over the last few years and has made runs at a national championship.

There are of course examples like this that happen in the workplace on a day to day basis that does not come close to receiving the same fanfare. These little things all matter in the grand scheme of setting your company’s culture.

We’ve seen simple things in the office. Cleaning up after yourself in the kitchen or conference room. Picking up the trash you knocked over. Putting things away where they belong.

Now that we’ve gone remote, there are still many ways that highlight a working company culture. Adhering to best practices with files and tools so your teammates know where to find things. Taking notes for those that couldn’t make the meeting. Sticking to your company’s communication protocols.

Of course, every company culture is going to be different. Some companies prioritize things that others won’t and that’s okay. You know you see a good working culture when something is important to the company and people are assuming that is the standard without giving it much thought.

My 3 year plan?

I minted my first two NFTs yesterday and officially joined the Illuminati project. I will say that it’s a completely new experience joining at the beginning of the project versus hopping in later on down the road. It’s much easier to embed yourself in the project and relate to others in the group. Also, you start to realize that no one really actually knows what’s going on and you’re just one of them as well.

On another note, it’s officially time for performance reviews. This year has been a bit easier as I’ve handed my team off to my replacement while I move onto the next project at Secfi. It’s been a nice relief to go from thinking about a bunch of my staff to thinking about myself for a bit.

For the first time in 3 years, I really started to sit down a bit and figure out what my next 3-5 years may look like. I know that I’m enjoying my time at Secfi and don’t have plans to leave, but I haven’t really given my career progression much thought. It’s not to say that I haven’t thought about my career or care about it, but rather that I’ve just been heads down looking to build Secfi and progression has come naturally versus setting a target in 3-5 years.

I thought it was a good exercise for me this past week to start thinking about what I wanted and the steps I needed to get there. I spent the week thinking about this in depth and at the end of it, I ultimately came to the conclusion that I truly don’t know what I want yet.

I felt that setting an arbitrary target like “be CEO or COO” was a silly target as titles just don’t mean that much to me.

I also felt that things are changing so rapidly in the world of fintech, startups and investing in general and I am interested in a whole slew of different things right now.

I also thought that my priorities and life will likely be a whole lot different in 3 years as Sophia and I look to start a family.

So ultimately this came down to the fact that I am interested in a whole bunch of things in the future and my career can go in so many different directions that creating a 3-5 year plan just isn’t the right way to go about it. In other words, things are fluid and I’m fully embracing it.

I know that I am working on some amazing things at Secfi for the next 6-12 months and I want to continue to work on it. I know I’m happy but have a lot of things to work on personally to grow. And I know the future can be really good to me when it comes to my career, but I just need to live in the present for right now and embrace the fluidity of things.

NFT World

I’ve spent the last two hours researching different NFT projects. The projects happening right now are absolutely fascinating and I’ll admit that it’s been hard to hold myself back from buying a whole bunch of NFTs.

I’m hoping to participate in my first minting tonight with the Illuminati NFT project. Fingers crossed that I’ll be able to snag a couple. I told Sophia that I was planning on spending 0.5 ETH (~$2,000) on these two NFTs and she almost flipped out. She joked that this better be a good investment and we better get rich off of it.

The reality is that most of these NFT projects will likely fail in the long run. Buying a NFT with hopes that it’ll 10x is the wrong reason to do so.

I view these projects as a way to get involved in the web3 community first and foremost. I am admittedly playing with house money on gains from my ETH and I am more than willing to pay to play with that cash.

Beyond the learning, the ability to be part of a great project and community is worth the price of entrance to me. I have met some amazing people on the internet and I hope to continue to meet great people as part of these web3 communities.

Of course, the possibility for gains on your NFTs is something that is undoubtedly on most people’s minds. I view that as an added bonus to everything that comes along with it.

Fingers cross that I get to mint my first NFT today.

Team get togethers and corrections

I’ve written a lot about our team get-togethers and how much of a difference that makes in team morale. We had an amazing week together as a U.S. team. Lots of great meetings and brainstorming to set the foundation to close out the year strong and spring us into 2022. The grand finale was our Christmas party on Thursday. We started out with drinks at the office and went out to a fantastic dinner at Corks. I can’t wait until we have the entire team from Europe and the U.S. together again.

On another note, growth stocks particularly in tech have had a rough few weeks and year overall. My tech heavy portfolio has taken a large hit. $DOCU has taken a 40%+ tumble after earnings. $PTON is down 66% over the last 3 months. Many tech IPOs in 2021 have taken a large drop.

The pullback might be a sign that fundamentals may actually matter after all. It sure didn’t seem like that in late 2021 where it seemed like every tech stock was headed for the moon.

I’ve had to reevaluate my portfolio quite over the last few weeks, but changes will be largely minor. My long-term outlook on these companies are still largely intact. I buy stocks that I want to hold onto for 10 years and despite these painful drops, I need to stick to my guns here.

Time will tell the winners and losers in my portfolio, but corrections should not force any rash decisions.

Put your head down and get shit done

There’s a ton happening right now at Secfi. For starters, we’ve got the whole US team in San Francisco for meetings and our holiday party tomorrow. It’s a fun and festive atmosphere. Given that, the work doesn’t stop.

We need a few good weeks ahead of us to close out the year strong and on top of that, we’ve got some really exciting initiatives that are in the works as I write this. There’s no time to rest and I’ve come to realize today that this won’t be an easy 3 weeks.

Startups are a grind and everyone knows it. There’s times when you just need to put your head down and get shit done. The next few weeks are one of those times. There may need to be some sacrifices made given the holidays, but the grind will be worth it as we accomplish our goals heading into 2022. I’m pumped to close out the year strong.

Playing with fire

I was responding to a Twitter thread in which a former CFO mentioned that he was burned by his company’s stock despite being a promising startup coming out of Y-Combinator. He had used a non-recourse loan to exercise his stock options through an existing investor on his company’s cap table.

Unfortunately, things didn’t work out and the loan ended up being underwater. Not only did he not make a penny off his stock options, but he was also stuck with a tax bill on the forgiveness of debt from his loan.

It was an unfortunate situation that happens more than we’d like to admit. Most companies actually fail despite what this market is portraying.

I had a few takeaways from reading this thread.

First, don’t risk what you can’t lose. Avoid financial ruin at all costs. The positive note for this individual was that at least the loan was non-recourse meaning that he didn’t come out of his savings to pay for the stock. In the last couple of years, I’ve seen individuals do some insanely risky loans and plays in order to exercise their stock options. Some take a second mortgage on their home. Some get as much recourse debt as possible.

This is playing with fire. Things may work out and you’ll forget this advice. On the flip side, this could result in you losing your home and potentially financial ruin. None of the upside is worth that downside. If you’re taking recourse loans or using your savings, make sure to not bite off more than you can handle.

Second, structure absolutely matters. Not all financing is made the same. If this individual had worked with a provider that structured the contract in a much more favorable way, he may not have a tax bill at all. In all likelihood, his taxable gain would’ve been washed out by his losses on his stock. He’d still be at a net 0 position, but that’s better than losing money on the stock.

I know I am biased here as I work for Secfi, but everyone needs to understand what they’re getting into and the potential downsides.

Freedom

I woke up this morning in Estonia and I’m now back at my desk in San Francisco at 4pm PST. I’m tired but in a manageable way. I was lucky to sleep about 4 hours on the flight and woke up at 8am PST. I tried to get work done on the plane but the wifi wasn’t being compliant so here I am back at the office. World travel is pretty amazing isn’t it?

Speaking of world travel, I had a great tour of the KGB museum which is in the Viru Hotel in Tallinn yesterday on my bonus day. Our tour guide was someone who grew up and lived through the occupation by the Soviet Union. She had some amazing stories to tell. The Viru Hotel was built by the Soviets as a way to attract western tourist and money. As you can imagine, the entire hotel was bugged by the KGB which was a surprise to no one.

Everyone was effectively monitored coming in and out of the hotel. Staff and guests were always being tracked. Non-compliance to their archaic rules could mean heavy jail time. The tour was a small glimpse into life during the Soviet occupation. It was well… brutal.

Our guide told many stories of what life was like. She and her parents would collect colored plastic bags as something for a special occasion. Apparently, black plastic bags were commonplace, but colored ones only came from western countries so the locals would save those for special days.

Perhaps the most bizarre thing I heard was that bananas were banned as they had come from western countries and the Soviets were trying to limit as much western influence as possible. Yes, bananas.

This was all just about 35 years ago. I’m glad I had the extra day to check out the museum as it made me realize just how precious freedom can be. Let’s not take it for granted.

Making the best of everything

I was all ready to head back to SF today after being gone 3 weeks. Got to the airport and the lady told me I needed a negative COVID test to fly despite being vaccinated. I argued with her that the website(s) that I looked at said you didn’t need a test until starting tomorrow, but in the end I was apparently wrong. The CDC website was misleading in that it failed to mention that the change going into effect tomorrow was reducing the testing window from 3 to 1 days rather than actually implementing a testing rule.

I tried to rebook to another flight later today, but the next flight back to SF was tomorrow morning. As most can imagine, I was freakin’ pissed. I was going to have to spend another day in Estonia. I had been sleeping 4 hours a night over the last week and I was already exhausted and wanted to be home. Woe is I.

I took 10 minutes to digest everything and start planning how I was going to “survive” another day when it all came and hit me at once. I get to spend another day in Tallinn, Estonia. I had just tweeted that it was one of the coolest towns I’ve been to and now I upset that I was forced to spend another day here. Man, I felt like an idiot.

Perhaps I was just a bit cranky and it took me awhile to realize that my vacation just got extended unintentionally. I quickly got some new life. Booked a COVID test back in town. Booked a nice hotel with a spa. Booked the KGB museum tour that I didn’t get to yesterday. I now have another full day of exploring Tallinn.

Yes, I’m still tired. Yes, the work is still there. But I can sleep and work any day… but traveling Tallinn is something that can’t happen all the time.

It was a good life lesson in positive thinking for me. I’m glad I was able to catch myself and turn my mindset around. Not everything will go according to plan and I need to make of everything in life no matter how frustrating or whose fault it is.

Monday will be a busy day and I’ll be recovering in sleep all week, but for now, let’s have a freakin’ great day.

Slush 2021

I spent Wednesday and Thursday at Slush 2021 which is Europe’s premier startup and VC event. I had a good time and learned a lot. Despite the gap closing, there is definitely a wide difference between the US and European markets and that was something I was paying close attention to.

The biggest difference I saw was that everything was largely VC driven and Europe seems to be much more VC friendly. In the current US market, VCs seem to almost be the ones doing the pitching trying to get allocations in hot startups. It has become undoubtedly a founder friendly market. In Europe, I still saw that VCs control most of the power still. I spoke to a few European VCs that said 2x liquidation preferences are still somewhat common. Founders are actively seeking out VCs, not the other way around. It’ll be interesting to see if this turns around at all in the future.

One other big difference in the markets is equity compensation just isn’t a big deal in Europe. Unlike in the US where companies are minting thousands of millionaires at every exit, Europe is still far behind in equity. Klarna celebrated making 75 employees millionaires at a $40b+ market cap. That number in the US is often in the thousands.

Most people we spoke to just aren’t that interested in their equity. They have some stock but none of them are overly excited about it even for those at unicorns. I believe that a lot of this is cultural and pay related. Europeans do not get paid as much as in the US, and that means much lower equity. In addition, owning a piece of a company is not something that is commonplace in Europe. I spoke to a CFO of a Series A startup and they had just started thinking about giving employees equity. A company without an equity plan would be at a serious disadvantage here in the US.

Lastly, it was hard not to notice how much smaller the European market is compared to the US. Compared to Money2020 which was solely a fintech conference, Slush 2021 which was for all European startups was much smaller. Yes, COVID has something to do with that, but I think that’s just the reality. The startup and VC market is just much smaller overall across the EU than it is in the US. Finland is rightfully proud of their 4-5 unicorns that have made it over the years. Today, there’s nearly a unicorn a day being minted in the US.

None of this is a knock on the EU startup scene as it’s still growing widely. There’s some amazing founders, operators and investors in Europe and it was good to see the thriving market. While they may be a bit behind the US in a few areas, I expect Europe to quickly start closing that gap over the next few years. It’ll be fun to watch and I look forward to comparing notes from Slush 2021 to Slush 2022.

Estonia

I’ve had a heck of a week. On Tuesday, I flew to Helsinki to attend Slush 2021 on Wednesday and Thursday. It was a pretty good conference that was geared towards European startups and VCs. I’ll probably write a lot more about it tomorrow when I’ve got a bit more brain capacity.

For now, I’m absolutely beat and going to keep this short. The jet lag and conference events caught up to me quickly. I slept quite a bit on my 2 hour ferry ride over to Tallinn and then again when I got back to my hotel.

Tallinn is a very cool city minus the freezing cold temperatures in the winter. It’s an old medieval town with lots of modern buildings surrounding it. I had a blast walking around today and I plan on doing a walking tour later today.

In terms of Estonia as a country, I have heard that it’s a big tech hub with lots of young engineers. The country has prioritized technology and the country is growing rapidly because of that. Someone even told me that the fastest internet in the world is in Estonia.

I’m excited to go out tonight and meet some of the locals and see what the country is all about.

#KGMI

Hello jet lag, my old friend. I ended up sleeping soundly from 9:30 until 12:30 last night. Then maybe snuck in a couple one hour naps throughout the rest of the morning. I’ve been in better shape, but I’ve been in worse also. I’ll need to stay positive and grind through 5 hours before my flight.

I bought into my first NFT community on Saturday. I do a bit of NBA Top Shot collecting and I had been looking to buy a few NFTs over the last couple of months. Part of this was fueled by speculation and another part was just genuine interest in web3.

Luckily, I was able to stay disciplined and didn’t chase for the speculative nature of NFTs. I know a lot of folk have made a lot of money on NFTs, but I believe the crazy appreciation days are largely over. I personally am much more interested in the general applicability and community building that comes from NFTs.

I have been lurking on a few Discord channels over the last few months and unfortunately I just couldn’t relate to many. There were too many topics I was uninterested in and I didn’t feel like I wanted to join any of them except for the fact that I could potentially make money off these NFTs. I felt those were the wrong reasons to join.

Enter Knights of Degen. The community built for sports and entertainment fans with an emphasis on betting, hence the degenerate gambler reference. This was more my speed. After spending a shit ton of money on gas fees, I finally found a knight I wanted and bought it for 0.2 ETH.

I’m still learning a lot and getting ingrained into the Discord. I’ve been having fun so far and will look to get more involved. I do encourage as many people to explore communities. It’s clear that NFTs will be a large part of web3 and I’m stoked to be participating at the next frontier of the internet. #KGMI

Europe for the week

And just like that I’m on the last leg of my 3 week trip. I landed in Amsterdam this morning, slept for 2 hours at my hotel and went into the office. Tomorrow I leave for Finland for the Slush conference until Friday and then I’ll take the ferry over to Estonia where I’ll spend a couple days for leisure before flying home finally.

This will be my first time attending Slush and I’ve heard great things. It seems to be Europe’s premiere startup conference and I’m giving a presentation on Wednesday for a group of 50 founders and investors. Like most conferences, it’s going to be equal parts exhausting and fun. I’m excited to meet operators and investors from this side of the world and get out of the SV bubble a bit.

I’m tired as Thanksgiving week at the future in-laws was not as relaxing as I would have liked. I’m sure by the end of Slush, I’m going to be happy to be by myself in Estonia so I have that to look forward to. In the meantime, I’ll be living off caffeine and adrenaline. No rest for the weary.

Grateful

I’ve been doing my best to practice gratitude everyday. It’s something I’ve developed as I started meditating daily years ago. There was a point where I kept a gratitude journal to write down 3 things I’m grateful for per day. I stopped that habit after a year or so, but I still do my best to wake up and think about everything I’m grateful for.

I do love Thanksgiving as it’s an annual reminder to be happy for everything that I have. I’ve got good health, great friends and family. I show up to work every day to build a company I am passionate about with supporting and awesome teammates.

I am truly blessed and I’m grateful for that.

The Happiness Project

Someone from our engineering team shared Shawn Anchor: The secret to better work on Slack today. It spurred a lot of positive discussion in the channel. I haven’t watched the video yet, but I read Shawn’s booked titled “The Happiness Project”.

To this day, I don’t believe there is one single book that has had a more impact on my life. I thank Shawn for a lot of my success and helping me realize my potential.

The theory behind the book is really simple. Doing good work does not make you happy, but rather being happy allows you to produce good work.

It’s simple but really changed the way I thought about life. I was 24 when I first read the book and working 80 hour weeks thinking that if I just worked a bit harder and move up the chain, I’d be happy. In truth, life and happiness doesn’t work that way. Since then, I’ve prioritized my happiness and wellbeing first and foremost and my work product has greatly improved.

I highly recommend everyone read his book or at least watch the Ted Talk above. Hopefully it has an impact on your life as it did for me.

The markets are humbling

As I write this, my portfolio has been down 8% this past week with the $SPY hovering only 1% down over the same period. Perhaps it shouldn’t be a surprise for my tech-focused portfolio that’s naturally going to have a lot more volatility than the $SPY. Regardless, the markets can be humbling at times.

Earlier this year, there were many who believe stocks could only go up. My portfolio certainly looked like that at times as it felt like every stock was hitting all time highs. Fast forward to November and most of my portfolio has retreated significantly.

The markets are humbling.

Cathy Wood’s $ARKK ETF which was the talk of the town last year has been down 15.84% YTD.

Chamath aka the King of SPACs who was perhaps the most popular investor earlier this year has taken his lumps as his investments such as $OPEN and $MILE have been in a downward trend since debuting on the public markets.

My point is to neither compare myself to Cathy or Chamath, nor talk down upon them. Quite frankly, I look up to both of them and they have done much more in their careers than I’ve accomplished. My point is that even the best and brightest investors can find the stock market humbling. Stocks don’t always go up.

No one wants their portfolios to be down, but it’s a good point for me to reevaluate my strategy and adjust. I’ll be focused on that as I rebalance my portfolio in the next few weeks leading up to year-end.

In-person meetings

I’ve been awful at writing over the last two weeks and I’m not happy about it. Last week simply just got away from me as I was in New York catching up what felt like a years and half worth of meetings in one week.

Speaking about New York - that city is fully back. Nearly all my friends who left in the pandemic have moved back and besides some masks here and there, you can hardly tell that the pandemic happened. It’s every bit as fun and exciting as pre-pandemic.

I had a whole weeks worth of in-person meetings. I missed meeting people in person and it was good to see nearly everyone back in office again. With that said, I felt like I was bouncing around the city all week and not getting much done. It was every bit exhausting and inefficient as it was fun. Of course, the inefficiencies you get from the commute and travel is the price you pay for that in-person camaraderie and social aspect.

Going forward, a lot of these meetings will likely shift back to Zoom. I’ll probably reserve a lot of my in-person meetings for first time meets or special occasions. I just don’t think spending a week in New York cramming as many meetings as possible in a week is an efficient use of my time and energy anymore.

I’ll look to spend this week catching up on sleep and work. I’m in Baltimore with Sophia’s family for Thanksgiving and it’s been nice being in a much quieter place. On Sunday, I’m off to Amsterdam then Helsinki then Estonia. It’ll be another busy week next week so I’m doing my best to rest up this week.

Trusting your instincts

I’m back in New York for the week before spending a week in Baltimore for Thanksgiving. Afterwards, I’ll be off to Europe for a week. Three weeks away from home is going to be tough. I’ve gone into this trip making sure I pace myself, rest and not overdo things.

New York is amazing as always. The energy is next level and I’m always happy to be here. We’re meeting with partners, recruiting and onboarding new hires this week. Our New York office is starting to take shape and I’m excited to spend more time out here.

This morning, I read that a company that I was targeting to do a personal deal in 2+ years ago is raising at a $10b+ valuation. I won’t divulge into details or mention the company name due to confidentiality but I love the space and the founders.

I wrote a two page memo in August of 2019 to share with some potential partners on this deal. Things were lined up and candidly we just got too busy to deal with getting the money together so I decided to pass on it. The valuation was under $500m at that time.

I knew back then I was onto something. In investing, you’re often wrong more than you’re right but this is one that I nailed. Unfortunately, timing and perhaps a bit of laziness prevented me from capitalizing on it. I should’ve trusted myself.

I’m kicking myself for this one, but it’s a good learning experience for next time.

Missing the boat

I try to avoid going to the Equinox on Union Street in the Marina as much as possible despite being the closest gym to my apartment. Unfortunately, my dentist appointment forced me away from my normal gym and into the bro-lair in order to get a quick workout before my night of work. I walked into the steam room and a few bros were talking about angel investing, web3 and crypto. Welcome to 2021.

I haven’t been shy about writing about web3 and crypto on this blog. I’ve been doing a lot of reading and trying to learn as much as I can to get caught up, but I constantly feel like I’m in an endless battle. Last night, I was slacking with a coworker and complaining about how many freakin’ crypto projects there are. It’s become nearly impossible to keep up.

Admittedly, there are many times where I have FOMO and feel like I’m completely missing the boat on the next big project. It’s almost like I’m constantly missing out on that next big token or NFT drop. It’s a common problem I’d imagine that others are currently facing as well.

In times like these, I believe it’s vitally important to remind yourself that we’re at the early stages of web3. The fact that we’re learning, reading and even participating means that we’re far ahead of the curve. Unfortunately a lot of these projects will likely end up not working out. The big thing in web3 is likely going to be something that not many are currently working on right now.

There’ll be plenty of opportunities as the future of the decentralized internet develops. Don’t get caught chasing something because of FOMO.

A weird year of investing

Like many, my portfolio over the last year has done remarkably well. This should be no surprise as the markets (both stocks and crypto) continue to hit all time highs. Most who have largely stayed long on their positions should have sizable gains over the last year.

As I close out the year-end and start to rethink my allocation and aim to rebalance, I can’t help but think what a weird freakin’ year it is for my portfolio.

My stock portfolio continues to beat the market but not by much. This is largely buoyed by some large outsized gains from a few stocks offset by a few big misses. I failed to trim my $PTON position after being up 100% and I paid the price dearly for that one. I took a heavy loss in $SKLZ and perhaps got caught chasing that one at too high of a price. On the flipside, I’ve made some good calls in doubling down on $SE and $RH.

The star of my portfolio largely is crypto driven. My outsized crypto position continues to grow rapidly and has started to approach the 50% of my liquid portfolio mark. I’m not sure how I feel about this yet. The safe bet is of course to diversify away, but the upside with crypto is there. This position has largely been created on gains and there’s an aspect of house money, but oversized is oversized.

The end of the year is a good time as ever to pay a bit closer attention to your portfolio and ensure that you’re confident in your allocation. I’ll be doing a lot more monitoring as I close out the year and perhaps make some tweaks.

We're so corporate now!

I had drinks and dinner with some early employees at Secfi last night. Since handing off my team, I feel like I had been a bit disconnected from them. It honestly felt like weeks since I last even spoke to them which is a big departure from speaking nearly everyday for the last year prior to me taking on a new role.

We had a great time. Not that I had any doubt to begin with, but I’m more convinced that the team is in good hands than ever before. I’m happy to see them happy and the transition go so well.

One of the things that came up was just how much things have changed over the last week. One of the teammates exclaimed at one point that “we’re so corporate now!” We all had a good laugh as we know we’re a long ways from being a big corporation, but of course know that things are somewhat headed that way.

It’s a natural part of growth as a company and we spent a lot of time talking about the “good ole days” which in fact was probably just a year ago. Things move really fast at a startup, but we’re doing a lot to keep our old ways of moving fast.

For now, I’ve got to put my corporate hat on and write some performance reviews. It sucks but it’s part of the gig.