Case of the Mondays

I’m having a bit of a tough Monday. My morning started early with meetings and by the time I was done with my string of meetings in the early afternoon, I felt drained. I’m not sure on the cause of this.

I had a good night of sleep and a good weekend. Perhaps I may just be a bit tired or perhaps this is my body and brain telling me that I’m a bit burnt out and need a break. I’ll need to see how I feel in the next few days and decide that it may be time to take a recharge week off.

In the meantime, I’m going to try to stay positive and take a quick break to go on a run to clear my head.

Celebrating the wins

It’s been a good week of work. We’re finalizing a lot of plans for the year ahead and also have really honed in some of our partnerships. In addition, we hit a big milestone in Secfi Wealth.

Quite often, I get caught up in the haze of work and forget to look back and see just how much we got done as a team. That’s often the hard part about startups. You accomplish a lot, but then it’s onto the next goal or milestone. It’s easy to forget to celebrate the big accomplishments. And we’ve had a lot of big accomplishments in the last quarter.

I couldn’t be prouder of what we accomplished. This last year has been probably the hardest of my career so far. It wasn’t just the hours spent working - I feel like I worked more hours in the past, but rather the outside factors that were outside our control.

Despite all the headwinds, we overcame and we’re in a great position right now in 2023. I’m going to take today to reflect on this and celebrate a bit. Then it’s back to the grind on Monday.

Speed of tech

I can’t believe how fast things are moving in the AI space. Just like the web3 craze in the last few years, things are moving faster than I can keep up. It’s been amazing to watch but at the same time overwhelming.

My list of companies and projects to check out has consistently kept growing. At any given moment, I may have 4-5 tabs on my browser up on different AI projects that I’ve been meaning to set time to play with. I feel fortunate to be living in such a time where we can take leaps, not steps in human progression.

There is a danger to all this however. Just like we saw in web3 where things moved too quickly, we may see that same effect in AI. The speed at which people flocked to web3 to build projects was awesome to watch, but it also lead to lots of scams and horrible failures such as FTX. The government and regulators simply can’t keep up.

I’m not advocating for the regulators to step in and outright ban AI like Italy has. That goes against progress, but I think we need to move quickly here before some unintended consequences come out of this. This is beyond my level of knowledge as to what exactly needs to be done. But I hope there’s a solution which protects the public but facilitates advancement and progress.

No mud, no lotus

I’ve been meditating for almost 10 years now. I started practicing when I was at my first job working for one of the world’s largest firms. I was working long hours, stressed, and just overall in a weird place in life. If I had to single out the most positive habit in my life, meditating is likely first.

There’s a big misconception about meditation in that it makes you calm and not think about things. In reality, meditation just helps you deal and accept those thoughts. It doesn’t make them go away. A good analogy is like laying in a park and watching the clouds go by. The clouds are still there just like your thoughts, but you’re just watching them go by and acknowledging them.

This morning my Calm app had a daily meditation called “no mud, no lotus” which has been one of my favorite ones over the years. In short, the idea is that suffering will always be part of human life and won’t go away. We can learn how to suffer better which makes us suffer much less.

This concept has been one of the biggest benefits of meditation for me. Over the years, I’ve acknowledged that our world is uncontrollable and that suffering is present in everyday life. I’ve learned to embrace the ups and downs in life like watching a cloud pass by. Everything eventually passes, even if it goes slowly.

Learning during the downturns

I’ve been fortunate that my startup experience has exceeded most of my expectations. I left PwC in 2018 to join a startup so I could learn and break into the tech scene. I took a big pay cut and took a chance on myself. I’ve never looked back. Of course, things haven’t always been perfect, but largely it’s been exactly what I’d hope for in terms of my learning and development.

The best part about working in an early stage startup like Secfi is undoubtedly the learning. From 2018-2020, I learned a lot about launching a product and running a business. In 2020, I learned how to deal with a black swan event and how to scale a company. In 2021, I learned on how to really scale a company and launch a complementary product. Of course, those are just the highlights of those years.

Probably the most interesting aspect to all this is how much I’ve learned in the last 1.5 years in the market downturn. I truly think I’ve learned more in the last year and half than I did in my first 3 years combined at Secfi.

Leading a team and company through a period where everything is on fire has been something that I’ve never wanted to do, but an experience that I am grateful for. I grew up a lot in the last year and half during this market reset. There’s been a lot of emotions and stress that have come out of this, but the experience is invaluable.

Recharge day

I had a frustratingly decent weekend. I decided to drive up to Tahoe Thursday afternoon and take Friday off for a recharge day. Everything sounded great in theory as we were going to drive up in off hours on Thursday and ski all day Friday. But the traffic bug caught us on Thursday and the Friday weather did not cooperate as it was cold and windy on the mountain.

In addition, I had signs of a slight cold during the week, but I decided to push through anyhow. Unfortunately the cold caught up with me and really threw me for a loop. I struggled quite a bit with my energy levels on Friday and Saturday.

I still had a good time although it wasn’t the weekend I had envisioned. The sun finally came out here in San Francisco and I’m feeling a lot more optimistic with the nicer weather. With that said, my one day off recharge day made me realize that I am likely due for some extended time off.

It’s been since the holidays since I had beyond a long weekend and it’s been a busy Q1. I’ll likely look for some opportunities to take a proper recharge week off.

FinTech

I decided to take this afternoon and tomorrow off to get up to Tahoe and do some snowboarding. It’s been a busy winter and unfortunately I’ve only got 2 days on my pass this season. I’m excited to finally get up and recharge my batteries a bit.

Today, I listened to a webinar in which Frank Rotman, the Founding GP of QED, spoke about his fund and his views on FinTech. It was fascinating to listen to one of the foremost experts in fintech. It’s my first time hearing him speak and I am just amazed by how much experience and knowledge Frank has.

It was satisfying to hear that Frank shares some of the same views on why he’s bullish on FinTech as me.

First, FinTech is incredibly difficult and not everyone can get in it. I joined Secfi as we were doing something complex and a large part of our moat is the difficulty in doing what we do. Unlike starting a DTC company where someone out of business school can get into and effectively disrupt, you need to have quite a bit of knowledge and experience prior to building in this space.

Second, finance in general is a very profitable business. Unlike other industries being disrupted like ride sharing or grocery delivery, financial services are proven profitable businesses.

We’ve taken a lot of hits in FinTech lately, but the financial services industry is prime for disruption. I remain bullish on the sector and proud to be a small part of it.

Time for change

San Francisco and the tech industry is a bit rocked today as we heard that the former CTO of Square and inventor of the CashApp, Bob Lee was stabbed to death in San Francisco. I didn’t know Bob, but from everything I read, he was a great person and a father.

It’s incredibly sad news as it seems like yet another random act of violence in our streets. I’m angry at the entire situation. From the fact that this happened all the way to the people using this to shit on San Francisco.

My stance on the issues here in San Francisco have been that it’s not nearly as bad as the way some folk love to paint it on Twitter, but at the same time it’s a real and growing problem. No it is not a lawless waste land where you can’t walk down the street during broad daylight, but yes it is common to see gross things all the time.

A lot of the criticism for the city comes from people who probably grew up in nice suburban areas. A city the size of San Francisco will never be their version of “paradise”. I’m very much happy to see those folks leave the city and flock for greener pastures like Miami. But at some point, change needs to happen. The problem is getting worse and it’s hard to ignore a lot of their valid complaints.

This city is wealthier than a lot of countries. If the politicians can pull their heads out of their asses, progress will be made for the better. Yet it seems like everyone is focused on the wrong things like blaming the tech industry for the problems we’re facing.

The man in the arena

There’s a lot of good jokes right now on VC and tech twitter. I’m not going into details as it’s not my M.O. to bash others in this industry so you can scour Twitter on your own. But this said investor was quite loud during the bull market years and unfortunately things are coming back to haunt him. If you’re going to talk shit, you best be ready for it to come back at you.

In the sports world, Caitlin Clark of Iowa exemplified experience beyond her years as she came up short against LSU in the national championship game and was taunted by LSU’s Angel Reese. There’s been a ton of talk about class in basketball, but hey shit talking is part of the game. You just need to be ready for it to come back at you. It’s been awesome to watch Caitlin handle the experience with class and dignity.

A lot of executives and investors could learn from this 20 year old from Iowa. I definitely did.

Q1 in review

We had a busy weekend that left Sophia and I absolutely exhausted yesterday. We had a much needed late afternoon and evening on the couch. This had all the makings for a rough Monday but I’m actually feeling great today. I made a pact with myself to stay positive going into today, and it’s worked wonders.

On another note, I can’t believe how fast time flies but Q1 is officially over. Next thing I know, we’re going to be heading into the holidays again. The quarter was a big mixed bag.

There was a lot of optimism going into the year that we could see things start to improve in the second half. A bank run paired with potential of a credit crises has largely put a damper on that optimism. I’m starting to see bankers and investors start to push back the timeline going into 2024 now.

The public tech markets have rebounded nicely with the $QQQ up 20% YTD. The private markets always lag behind the public markets so there is reason for potential optimism here. With that said, I do feel that there is more pain ahead. Stripe’s down round probably is the first big domino to fall and we’re going to see more down rounds soon. I’m all open for this as the faster we rip the bandaid off, the faster we can move on.

Personally, Q1 was not as exciting as Q4 considering I got married in December. With that said, Sophia and I have had renewed energy lately trying to enjoy our lives as much as possible before we start having the family talk. It’s been a lot of fun.

Admittedly, I’ve had trouble staying positive over the last 12 months. There was a lot of bad news out there and it’s been a struggle to keep up with everything. But I’ve been feeling better than ever before recently and I believe that’s largely due to my changing mindset. It’s been working and I’m very optimistic about the rest of the year.

The Stripe problem

I wrote about Stripe’s unique fundraise in Secfi’s newsletter, Founders and Funders. You can read a bit more here.

I’ve had a lot of good reactions to it from Stripe employees and non-Stripe employees. However, I am a bit shocked to hear some of the stories from the Stripe employees we are working with.

Like most of us, a lot of Stripe equity holders got caught up in the mad rush of 2021 and had thought Stripe would have been public by now. The risk that some people took on to exercise Stripe options is downright scary.

I’m seeing a lot of people who borrowed against their 401ks, borrowed money from family and friends, exercised with no way to pay on the hopes that they would be public, etc. Some even took risky recourse type loans and most of those people have been completely wiped out.

Yes, they’re now in a position where they are getting nothing from the Stripe shares because they took on leverage to exercise. It’s really freakin’ sad. A lot are blaming Stripe for this problem and while I do share the sentiment that they probably should be public already, it’s also on each individual to make the right choice for themselves. Unfortunately a lot of these individuals made the wrong choice.

Clarity in times of crisis

We’re in the process of finalizing our strategy and plans for the coming year ahead. In a normal year, we’d have done this back in November. But given the volatile market and changing landscape, we had pushed things off to see where things stood after Q1. We’ve still got a bit of work to finalize things, but I don’t think the team has ever been so in sync before.

The tech bear market has actually bonded us a bit closer together and forced us all to be crystal clear in our objectives, goals, and plans. Like pretty much all startups, we likely got a bit lost in the craze of the bull market. We didn’t pay as close attention to the details as we were busy growing the team.

Now with tightening budgets and capital at a standstill, we’ve been forced to tighten up for the better. We’re operating at a much higher efficiency and level. It was absolutely fascinating to watch as each team presented their proposed plans for the year ahead and seemingly everyone was already on the same page.

I’m more excited than ever for the year ahead.

$ARB

Given all the AI hype, it seems like people have forgotten about web3. Well.. I suppose not completely as the regulators have crypto squarely in their sights. That’s a story to watch in the coming months.

In other news in crypto world, Arbitrum just ran an airdrop for their token $ARB last week. Arbitrum is the largest Ethereum layer 2 platform. I’m not the foremost expert in crypto, but generally speaking a layer 2 or L2 platform is a network that sits on top of a L1 like Ethereum. L2s are a solution to the scalability problem of Ethereum and allows transactions to go faster and cheaper.

I’ve been playing around with L2s, specifically Arbitrum over the last year and half or so. The first thing I noticed is that the cost of the transaction (gas) is night and day compared to a transaction on Ethereum directly. It made a lot of crypto gaming built on-chain actually possible. I’ve dabbled in a lot of projects on Arbitrum and have had a lot of fun with it.

Arbitrum did an airdrop of $ARB last week in order to give their users governance tokens to vote on the future of Arbitrum. Of course, one (major) side point to all this is that these tokens can also be sold as they can be viewed as ownership tokens of Arbitrum. The market cap currently sits at around $12B fully diluted.

I’m overall bullish on the future of L2s such as Arbitrum. They solve the scalability issues of Ethereum at the moment and I’m part of a lot of interesting projects being built on Arbitrum.

Daffy and DAFs

Today, Secfi announced a partnership with Daffy. We’re excited to partner with such a great organization. In short, Daffy is a donor advised fund and a non-profit. Users can easily create an account at Daffy and donate to their favorite charities in a few clicks.

So how is this different than just plugging in your credit card to your favorite charity’s website? Well, Daffy allows individuals to contribute to what’s called a donor advised fund (DAF). With a DAF, you can contribute highly appreciated stock and crypto, receive a tax deduction at the full market value, AND not pay any capital gains on the appreciation.

This is a win-win scenario. The contributor gets tax benefits for contributing. The charities get the full market value of the shares pre-tax. In addition, individuals can even dictate which charities get allocated funds.

We knew that charitable giving was something that we wanted to implement at Secfi, even from the start of the company. We want to help our clients do good in this world and we want them to achieve that in an easy, tech enabled approach. Daffy provided that.

We’re excited to see this partnership evolve.

Twitter's new "valuation"

I had a great weekend recovering after last week. By the time Friday came around, I could tell that I was running on fumes. It took me until Sunday to start feeling better though as I had that much sleep debt built up. It was a much needed weekend of rest and leisure.

It was a rather slow news weekend which was great. Perhaps the only notable thing to mention is Elon mentioning that Twitter is now worth $20b and employees would be issued stock compensation at below that price.

I don’t really know where Elon got the $20b number from. It could be the 409a valuation of the company, but it could just be what Elon decide was a good number to announce to the public. He tends to say what he wants, when he wants it. And let’s not forget that he paid $54.20 per share for Twitter which is of course a joke on 420.

The original employees who cashed out at $54.20 must be laughing right now. Many of these folks were fired or laid off and they were able to cash out at a much higher valuation. Not an awful parting gift from Elon.

Those employees still at the company likely falls into one of these two viewpoints. Some may think that the $20b is way too high still and they’re getting absolutely screwed with their equity grants. The other group may think that Twitter is still severely undervalued and believe in Elon’s vision.

I don’t know where the majority of employees sit on that spectrum. I’d imagine if they’re still at the company that they believe in Elon still and possibly believe his statement that the company may be worth $250b one day. I’m not sure where I sit on this, but if I had to put a bet on things, it’s hard not to take the under on that.

"The best funds are the ones who did less bad"

The VC industry has taken quite a big beating over the last two years. The media and world has taken their shots on the industry. A lot of the criticism is undoubtedly warranted. A lot of investors acted on hype and overpaid mightily for a lot of companies. Fundamentals were non-existent for a lot of investors.

In defense of VC, it is an industry where you expect to fail more than you succeed. An early stage fund can have over half of the portfolio go to 0 and still be wildly successful. Some funds have caught a lot of flak for investing in certain companies like FTX, but the reality is that missing an opportunity like FTX, if successful, is much more costly than not making the investment.

One constant saying I heard during my trip to Sand Hill last week was that the worst you can do with an investment is lose 1x but the upside on some of these deals are gigantic…1000x even. For a lot of VCs, taking those shots far outweighs the potential downside. Of course, the idea here is to make sure you take the right calculated risk which is harder than it seems.

Perhaps the most interesting thing I heard all week during my trip to some top tier VCs is Samir from Khosla stating that “every fund overpaid for companies in 2021, but the good investors are the ones who did less bad”.

That statement really paints the picture of how the industry works. It’s an industry where you need to take shots and you fail more than you succeed. Yet, many in the media love to focus on the failures and attribute blame to the bad picks they make.

As we eventually come out of the tech reset, we’ll see which funds did less bad. My hunch is that it will be the ones who have been through these cycles before. If there’s one thing I’ve learned during this downturn, it’s that nothing can beat experience.

Sand Hill

I took the last couple days off from writing as I was at an event in Palo Alto called the Innovation Field Trip. It was hosted by a fellow startup and Secfi partner, Allocate. The event was largely a way for people not in the startup/tech ecosystem to meet VCs and learn about what’s getting built here.

Despite living in the area and being part of the ecosystem, I was incredibly impressed by how well the event was run. We met a lot of top tier venture capitalists both who are running solo shops as well as those working for some of the biggest names. Huge shout out to the Allocate team for putting it on.

I seldom make it down to the Menlo/Palo Alto area. Growing up and living in San Francisco, I never really saw the allure of visiting the “legendary” Sand Hill road much. My trips down there are for football games when UW plays Stanford.

This time around felt a bit different for what I believe to be a couple of reasons.

I believe my change of perception comes from the fact that I’ve been working a startup the last 5 years and have come to appreciate the companies being built. Startups are incredibly hard and there is a level of appreciation I now have for those that endured the long journey of building a successful company.

Secondly, I’ve come to terms that all VCs are not built the same. I’ve had somewhere between an irritation and disdain for a lot of VCs out there - both ones that I have met and ones that I haven’t. Some have treated me like shit. Some are just annoying as shit on Twitter. I also blame some for helping cause of the issues we’re facing right now.

After meeting over 10 different managers between the 2 days, I’ve realized that most of these top tier VCs also share that same disdain for a lot of these same VCs. They acknowledge that the industry has gotten out of control and will need to be reeled back. Some had harsh words for those “VC tourists” and even called out quite a few.

I do have a new appreciation for the industry after the trip. Most of these funds are built more like startups than they are actual just investment funds. It was really awesome meeting and learning about each firm and how they differentiate.

Once I get my head above water and get a chance to put my notes together, I’ll write more about some of the key takeaways. For now, back to work getting to inbox zero.

Getting away from the madness

It was incredibly stressful leaving on Thursday as I was absolutely swamped given all the news and happenings of the week. I had even thought about canceling last minute so I could focus on work.

I’m glad I didn’t. It didn’t take me long on Thursday to realize just how much the last few weeks have taken out of me. I felt my anxiety and tension the entire flight and it didn’t really subside until my friends and I met up and started our night. There was an immediate sense of relief as my friends and I hung out at dinner and talked about anything but work.

With a lot of the happenings in our world, it was amazing to just get away from everything for a little bit. Sometimes you just need to escape the craziness of your current world and I’m in a much better headspace after a 3 day break.

No rest for the weary

I booked a trip to Vegas this weekend to golf and watch March Madness with some friends. I booked it a few weeks ago given things were a bit slower and I wanted to take advantage of the times.

Of course, we’ve had a hell of a week with the SVB and bank issue combined with some major announcements like Stripe’s round closing.

I couldn’t help but just laugh. This may be the worst weekend to go on a trip. For some reason, this seems to happen to me quite a bit for some reason. Everytime I go away, a big deal comes through the door or some news hits the wire.

I’ll be running on fumes this weekend, but I also need to pace myself and ensure I’m getting the proper rest. It’ll be a good trip regardless.

Ponzi scheme?

I had a great chat with the CFO of a unicorn today. I hadn’t spoken to him in about year and we were shooting the shit about all the events of the last 12 months or so. We shared a lot of the same cynical takes on the broader tech and VC industry. We couldn’t help but ponder just how much of this mess that we’re in right now is because of greed in the industry.

I was especially intrigued by what he said about VCs of the last 3 years effectively running a ponzi scheme. Many of these funds and investors were just bidding up the prices of their portfolio companies and hoping to get out before the crash. They had known that this was not sustainable but they participated anyways in hopes of building massive gains and dragged the entire industry along with it.

I had never heard someone equate VC to a ponzi scheme before. I thought it was an incredibly interesting take and angle on the situation and it was hard to argue as many of these investors had this idea in mind.

The unfortunate part to all this is that a lot of these companies will suffer greatly from all this. There’s many companies out there that are trading down over 80% of their peak valuations and not many can or will recover from a large crash whether they are private or public.

I do believe there are many great investors out there looking to build companies. I’m personally ready for the market to turnover so we can get back to building.