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.

Launching versus scaling

I’m officially over 3 years at Secfi and quite a successful one. I’ve learned a whole lot, met some amazing and smart people and have found a niche that fits my interests and background. Naturally, a lot of tech employees tend to move around jobs every 2-3 years but I’m loving my time at Secfi and I decided to double down and take on the next project at Secfi.

The last few weeks have been an interesting change of pace going from a scaling a business to a building/launching a brand new product. It definitely takes a different mindset and admittedly has been a bit of a transitional challenge.

My first year at the company was really centered around building and launching our core financing product. Things were a lot more unknown and open-ended. There was a lot of individual work and brainstorming. Many days would go by when it would just be me and my computer screen as I thought through the product and our best go-to-market strategy.

As things developed and we started selling the product, things shifted to a growth mindset. The building blocks were set and we just needed to scale. That’s largely how I’ve spent my last two years. I built teams and playbooks. We made mistakes and iterated. We focused on process improvements and brainstormed cross-functionality on how to streamline everything.

Now I’m back to building and I’ve loved the new challenge, but it has been a bit of a transition to a new mindset. There is largely no immediate gratification when you’re building something brand new. When we were scaling, we saw numbers come in. Big deals were closed and we were able to quantify success with revenue. When you’re building and launching a product, there are no immediate sale numbers. You have small wins combined with a lot more roadblocks.

The beauty behind launching a product is that these small wins start to get bigger and bigger over time. I’m really excited for that. The first dollar that comes in from this new product will be a monumental milestone. The key here is reminding yourself to get those small wins every day… they’ll add up even though you may not get that immediate gratification.

The metaverse

If you’re sick and tired of hearing about the metaverse, I’ve got bad news for you. It’s coming and it’s here to stay. We may be a lot closer to that online virtual world than most of us probably think - in many ways, it’s already happening. We’re all living in some form of a metaverse whether it’s through video games or working through Zoom. We just don’t realize or call it the metaverse yet as it hasn’t all been tied together.

A lot are probably going to be scared shitless reading the previous paragraph. There is legitimate fear that we’re all going to just move to online lives, ignore each other in person and all end up becoming human hermits programmed by Mark Zuckerberg.

I for one have a lot more of a positive outlook on what the metaverse is and can do for us.

First, I think it’s important to establish what the metaverse is. I don’t believe there will be one dedicated world like Ready Player One portrayed. The metaverse will be a term used to describe specific experiences or services. We may log onto the Fortnite metaverse to play video games in the morning and then go into the Nordstrom metaverse to go online shopping with friends in the afternoon. This may all be capped with a concert at MSG that we would attend virtually.

The hope is that these metaverse experiences will supplement our current lives, not replace. The metaverse has a real chance to enhance our lives while making things much more convenient.

Going back to the concert example above. Let’s pretend the Warriors are playing the Knicks at MSG and I live in San Francisco. I could fly to NY, book a hotel and buy tickets - but it’s going to be a really expensive trip. Would I typically prefer to go in person? 100%. Would I still be able to enjoy myself with a virtual experience through the MSG metaverse? 100%.

I can still attend with friends and have a great time from my living room. Nothing can replace a live experience, but when faced with not going or going virtually, I’d take it.

This all sounds pretty damn good to me and I’m excited to see what the future may bring.

Are we living in a Scenius?

I just finished reading Packy McCormick’s piece titled Sc3nius and it’s fantastic. In summary, Packy describes how we’re living in a Scenius which is the communal form of the concept of genius. The idea behind Scenius is that the periods of greatest human progress have been a product of communal genius fostered by multiple factors.

The Renaissance, the Enlightenment, the emergence of Silicon Valley and now…. web3.0. Packy writes that we may be living in one of the biggest moments of human progress. Our grandkids will be writing about today and how building blocks of web3.0 helped shape the future.

I’ve written quite a bit about the times we’re living in. It’s hard to ignore that tech has hit an inflection point fostered by the blockchain. I don’t doubt that we’re living in extraordinary times right now and that the future may be looking at this time as a Scenius.

Perhaps another and perhaps simpler way to view these times. The last few years have been hard for many of us. We’ve seen political turmoil, civil unrest and of course a devastating pandemic strike. Many have been looking to tech as the future for creating a better society - so far that has been a mixed bag. We need some positivity in this world and web3.0 may be that answer for all of us.

Web3.0 knows no borders or race, at the most core sense, it empowers the individuals and rewards them for banding their collective intelligence together. In essence, Web3.0 may be that tech we’ve been looking for in the last century that can actually unify the world. That’s exciting and something everyone should get behind.

Regulation is coming

I’ve been interviewing for a Head of Compliance at Secfi and it’s been a welcome change to my usual interview cycle. For one, I’m interviewing more on current knowledge so I get to pick the candidates’ brains quite a bit.

I’ve had a lot of interesting conversations over the last few days discussing Gary Gensler, crypto and where the SEC goes from here.

Crypto companies v. Regulators will be an interesting battle to watch in the coming few months and years. Gensler isn’t wrong when he says this is the wild west right now and perhaps some fair regulation is actually needed. Key to that is that it needs to be fair.

I don’t love how the SEC picked a fight with Coinbase by issuing the Wells Notice preventing them from starting crypto lending. It seemed like they wanted to target Coinbase and didn’t provide much background as to why.

I’m not sure how this all plays out, but one thing I am certain of after speaking to some senior compliance folk is that regulation is coming. It’s going to get harder for companies to launch, especially in the crypto and blockchain space. Startups and companies should prepare accordingly.

Money2020

I’m finally getting my head above water after my vacation and Money2020. A week and half away from my “desk” is never fun to catch up on, but it was well worth it.

I had a bunch of thoughts on Money2020 and I’m too brain dead to formulate them into a cohesive blog post so I figured I’d just bullet point them for simplicity sake.

• I forgot how much fun it is to meet people in person. There’s a level of personal connection that you get in face to face meetings.

• I also forgot for 18 months that network = net worth. It’s amazing how many connections and intros I made in 2 days.

• Networking is exhausting. There were definitely times where I hit a wall and had a hard time.

• Holy crypto and blockchain. I couldn’t believe just how many crypto and blockchain companies are out there right now. It’s undeniable that web3.0 has arrived.

• Everyone is an investor. All my Uber drivers wouldn’t stop talking about trading crypto, stocks or FX. I’m not sure if I should be scared or impressed. My driver to the airport told me to buy Shiba Inu coin but warned me that it’s a pump and dump.

• Seems like everyone at the conference has made at least 1 angel investment. It’s pretty impressive with how many are investing in startups.

• $50 minimum at the craps table is a fast way to lose everything. Stay away. $25 on the other hand is manageable.

Overall, I had a great time. Made a lot of new friends and potential work connections. I wish we went all out this year for Secfi, but it was tough with the pandemic. Next year, we’ll definitely have a bigger presence.

Time to go home

It’s usually hard for me on the last day of vacation as we travel home. Often there’s a feeling of dread of going back to work and feeling like you didn’t do enough. I’m happy to report that today feels a lot different.

I feel good about everything we did on this trip. We had a great mix of activities and relaxing. I feel refreshed and rejuvenated and I’m excited to go back to work.

Of course, one side of me wants to just quit my job, free lance and live in Baja for as long as I can, but I know myself and not having something to build would bother me.

We’re going another quick beach session in the morning, grabbing some tacos and then heading home. I’ll be home a grand total of 14 hours though as I have to get up and go to Money2020 in the morning. Busy week ahead but I’m excited.

A great week

They always say you don’t realize you need a vacation until you have a vacation. Well I realized I needed a vacation and I now realize that I need vacations more often.

It’s been largely an amazing week. Work has been minimal to just a few calls/texts here and there. I’ve done 6 dives in Isla Espiritu and Cabo Pulmo. I’ve done a lot of relaxing and have slept a good amount all week. We’ve eaten some great food and hung out with close friends.

The week long trip has been perfect and what I needed to unwind. More importantly, this trip was good for me to realize that a health balance of work-life is sorely needed. After a week, I’ve started to get excited to go back to work.

I’m back to San Francisco tomorrow and then headed to Vegas for Money2020 for a few days. It’ll be a good trip and I look forward to being nice and rested. In the meantime, I’m headed to the beach all day today and tomorrow morning before my flight. Cocktails and Tiger Wood’s book is on my agenda.

Unwinding

Weekend 1 of vacation has started off with a bang. After a drive from San Jose del Cabo to La Paz on Friday, we went diving in Cabo Pulmo on Saturday and Isla Espirito Santos on Sunday.

The highlight was Saturday when we dove a wreck in Cabo Pulmo and saw a goliath grouper as well as a bull shark. I joked with the team and on Twitter that the bull shark said the bull market continues for another year!

On Sunday, we dove with sea lions and then checked out another wreck. Diving has become an amazing hobby that both Sophia and I picked up together and it’s been great for our relationship as well as meeting new friends. We don’t have anymore dives planned, but we’re thinking we may head back to Cabo Pulmo on Thursday or Friday to do another dive.

So far, the vacation and unwinding has been great. I’ve been able to unplug largely and despite doing about an hour of work this morning to clean things up and push things along (as well as buy some stocks and crypto), I’m happy to report that my stress level is at a YTD low.

Today, we’ll be wrapping up work this morning and then just going to have a day to relax, explore and eat. I may look to get a massage and take a nap on the beach. I need to do this more often.

Trust

You have to have a lot of trust when you’re a leader in a startup. Compared to big companies, at a startup, there are often no guardrails. Often times, you’re just going after it with the little to no guidance you have. Most of what we’ve done at Secfi hasn’t really been done before - there’s no way to figure out the best way to do things without actually going out there and doing it.

I think leaders often forget of the mistakes they made while they were learning and getting things up and going. I often have to remind myself how much trial and error there was to get to this point.

I’m entrusting a lot of my team to handle things while I’m out on vacation this next week. Yes, it scares me a bit, but I have full trust that they will execute. They are smart and we’ve armed them with everything we can. Sometimes the best way for people to learn is just to learn by doing. It may not be perfect, but they’ll be even better coming out on the other side of it.

This admittedly has been one of the hardest parts about growing Secfi. I’ve gone from doing pretty much everything to having to hire people who will take over these functions. It’s tough to let go often, but it’s also a beautiful thing to watch when someone takes what you’ve built and makes it even better.

I’m lucky to have an amazing team that’s going to keep things rolling while I’m out. I expect to come back to a lot of wins in just the week I’m gone.

Time to chill the f out

It’s been amazing week from a work perspective.

We held strategy sessions as a management team and planned for the next year.

We had a big win with a partnership opportunity.

We won big from a sales perspective and jumpstarted our aggressive Q4 goals.

After a shitty last week. Things are coming along.

It’s a perfect time for me to check out for a bit and recharge my batteries. I’m headed to Baja on Friday and plan to check out for a week and some change.

I’ve written a lot about burn out and exhaustion on my blog over the last year. I tried to take some time off in June but ended up working a lot. This time I vow to take time off, relax and enjoy life.

The team is in a great spot, and I’m excited to come back recharged and crush Q4. In the meantime, I’ve got big plans to do a lot of diving, eating and relaxing on the beach.

Talent

We’ve been holding strategy meetings as a management team this week and the one thing that continues to come up is talent. We’ve done a good job recruiting lately with over 20 new hires in Q3, but it has taken a village to get to this point.

The world has changed since the pandemic. There are perhaps more open jobs than ever before across all industries and pay classes. Tech employees now have the ability to work from anywhere and can demand maximum flexibility.

Like most startups, we realize that winning the talent war will be the most critical aspect to our success as a company. We’ll need to continue to recruit and retain talent at a high level. In order to do so, we’ll need to adapt to the demands of the modern tech employee.

We’ll need to make some strategic decisions when it comes to the future of our employees and location. The future is remote and we’ll need to find the right balance between fully distributed and in the office.

One trend that will be admittedly difficult to overcome is the rise of the gig economy. Workers are turning towards the gig economy versus full time jobs and we’ve run into employees who have decided to stay free lance versus join us. We’ll need to control what we can and look to foster an environment that allows flexibility and the chance to work on new exciting projects. We’ll continue to build a culture that celebrates team work, camaraderie and mutual goals towards building something great.

There are and will continue to be a lot of challenges as the future of work evolves. At Secfi, we’ll continue to adapt and evolve as a company to stay in front of the talent wars to come.

Mental Health Day

The US team at Secfi had the day off for Indigenous People’s Day/Mental Health Day. Unfortunately only a fraction of workers I know had the day off - I’m hoping to see that change in the future as we prioritize worker health and happiness.

I took full advantage of the day to hang out with my 10 year old half sister. We had a great day going to Scandia which is a small family fun center with go-karts and an arcade which is what my sister loves doing. It was well worth the hour drive to Santa Rosa.

There was a long list of things that I wanted to get done over the weekend which included tasks such as rebalancing my portfolio and catching up some reading. I made a big dent on that list Saturday morning but personal things caught up and I unfortunately didn’t get to where I wanted to be going into this work week. I thought about cutting my day with my sister short to get back to catch up on my list, but then remembered the spirit of this day off.

It was a good reminder that while productivity is generally a good thing, there are often times more important things in life like spending quality time with my young sister. My to-do list can wait another week, but days like today are worth much more than checks on my list.

Pissed

Today was one of those days where seemingly everything is going wrong and we received bad news after bad news. If you do this startup thing long enough, you’re going to have these days and unfortunately they happen more often than you like.

It sucks but it happens. The ups and downs is one of the many really hard things about startups. I’ve had many of them over the last few years and while these days are not nearly as bad as when we were in the early stages, they always suck.

You invest much more than your worklife into your startup. It becomes almost part of your life for better or worse. When things go bad, it’s really tough on your psyche. The beauty behind all this is that when things go well, there may be nothing more satisfying from a work standpoint.

Days like today suck, but the most important thing is to put your head down and get back to work. There are better days ahead.

Worldwide Web3.0

I’ve forced myself to carve out a few hours tonight to dedicate to doing more research on web3.0, crypto and recent projects. I know, I am severely behind on the trends. Work and personal life have been priority recently and I haven’t been keeping up with the latest trends.

There’s only so many hours in the day and I’ve realized tonight that I need to peel some personal/social life hours back for more alone time to do research and learning.

Exploring the wild west that is Web3.0 is fascinating. I honestly feel like a kid discovering the internet for the first time all over again. It’s fun and exciting but confusing at times. There are so many cool projects going on right now and it’s hard to keep track of everything going on.

A lot of these projects will fail. A lot of these projects will gain traction and then fail. And a lot of these projects will be the face of Web3.0. I’m excited as ever to dig in more and be part of the Web3.0 revolution as a consumer and an investor. It’s an amazing time to be alive.

I know I won’t be at the forefront of many of these projects, but just like Web 1.0 and 2.0, we’re just touching the tip of the iceberg and it’s better “late” than never.

NL West Champs

I’ve written a lot about my battle with exhaustion and burnout. Lots of this was due to a crazy summer travel schedule. After a few weeks home, I’m happy to report that I’m feeling a lot better. I’m sleeping more and getting back to a much more consistent schedule. I’ve got a couple of weeks of work before I go on vacation to Cabo. I can’t wait for a much needed vacation.

The Giants clinching the NL West today saved an otherwise terrible sports weekend for my teams. The Giants won 107 games, the most in franchise history, and were picked to finish on the bottom of the division in the preseason.

Winning the NL West is a testament to the Giants organization. We have a group of veteran leaders that are playing some of the best baseball in their careers. We have under the radar stars exceeding their potential. This is a product of the culture of this team and organization. This team believes in each other and does not give up.

It’s been amazing to watch when a team and organization fire on all cylinders. It’s going to be fun to watch them make a run at the world series. I have no idea if they will win it all - there are undoubtedly more “talented” teams out there. One thing I do know though is that everyone in that club house believes they will win it all and when you have a culture like that, anything is possible.