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.

This is 31

I often need to be reminded that I’m no longer in my 20s. Yesterday and this morning was one of those reminders.

I went to the Giants game last night with a few of my old high school friends. It was a relatively tame night because well it’s a baseball game, but we had a few drinks before and during the game and ended up getting home around 11:30.

I woke up this morning feeling like I slept 2 hours and went to a rave all night. It’s a bit embarrassing to admit that I feel hungover after a few beers and sleeping only 7 hours, but that’s your 30s for you I suppose.

While I was still productive today at work and got a lot done, days like today are a good reminder to be conscious of rest and drinks when out and about.

The best ideas

I’m always amazed by how nearly all my best ideas come from when I’m in the shower, at the gym, eating, etc. My best ideas pretty much come to me anywhere besides when I’m actually trying to think about it in front of my desk.

Today, I was hitting a bit of a lull at my desk. I decided to take a long gym break and eat lunch out by myself. Sitting down at lunch today, it all started to come to me. By the time I got home, I had pretty much everything mapped out in my mind.

This isn’t a brand new discovery by any means, but it’s a good reminder that work doesn’t always need to be in front of a computer.

Shifting mindsets

As I move onto to my next project at Secfi, I’ve had to start to adjust my work style quite a bit. When I first joined Secfi and we were first going to market with our financing product, there was a lot more strategizing, planning and research involved. I had to be a lot more creative and a lot of what I was doing was strategic planning.

After awhile when we got up and running, my work started to shift to more of an execution role. Our playbook started to become more and more defined and we focused a lot more on just executing that playbook. Think lots of calls, meetings, emails, etc. with clients. Of course, there was still a lot of strategy and planning involved but it was different than the early days.

Now things have come full circle as I’m back to a brand new project at Secfi. While I’m still involved in our financing product, my day to day is a lot more free. There’s a lot more research and brainstorming on a day to day basis. I no longer have 8-9 hour days of client calls.

It’s a welcome change, but definitely a big shift back. It requires much more discipline and deep work which is something I’m still getting used to again. There’s not a lot of immediate results or gratification like closing a deal so it’s much more of a slow grind. It may be months until I start to see the fruits of my labor on this new project.

There’s a lot of perks however - my days are much more free and I can work from nearly anywhere since I’m not on calls. It’s going to be real nice to take advantage of not being on Zoom all day.

Web3.0

I may be the last person to write about web3.0 on their blogs on the internet. It’s of course been the talk of the town in the tech world for the last few weeks.

Web3.0 is the overarching term that covers nearly everything popular in the tech world including cryptocurrency, blockchain, NFTs, creator economies, work from anywhere, etc. It combines all these things under a simple umbrella that the future of the internet (and world) will be decentralized in which the people have the power.

Power out of the hands of institutions and back in the hands of people. That’s a powerful statement that should get pretty much everyone excited… unless you’re the CCP.

We’re at an amazing time of the world. Fresh out of a once a century pandemic, we a plethora hungry individuals with more resources than ever before out in the world building. The promise of tech building a better world may never be more true than today.

We’ve got a long ways to come until we achieve the future we want, but I don’t think I’ve been this optimistic about the world since I was a child. What a time to be alive and building.

The cycle of life within a startup

We had a blast last week with nearly the entire US Secfi team in the office. It was evident that everyone sorely misses colleagues and work events like these. We’re hoping to do this once a quarter and hopefully do a larger trip with the broader European team once a year.

I caught up on a lot of rest over the weekend finally. I got two rounds of golf in with my Saturday round being some of the best all around I’ve played and Sunday being one of the worst outings I’ve had. Golf will do that to you. One day everything seems to be working and you’re thinking you're going low the next day, and of course it all comes apart.

I’ve written a lot about how much we’ve grown over the last few months. One thing that is inevitable with startup growth is that people will start to have their roles narrowed. The earliest employees of a startup will need to be like Swiss Army Knives in which they can do a little bit of everything. As we grow, we start hiring more and more steak knives. Roles and responsibilities get spread out amongst other employees and early employees will have to give up a lot of tasks.

This can be a sensitive subject as early employees have taken a lot of pride in building their team/product. It’s not easy giving up the thing you’ve spent so many hours building. Seeing your successor run it her or his way as well can also be tough. But this is part of the growth path and it’s necessary for the company to continue to grow. There comes a time for everyone to move on and we need to put aside our own egos and let our new hires bring in their own thoughts and ideas to help grow the company.

You build, you grow and then you move on to the next task. That’s the startup cycle of life.

As for myself, I’ve been experiencing this a lot as I look to transition my team and role to someone we hired to take over. It hasn’t been easy, but I know it’s what best for the company. The beauty behind these transitions is that it opens up the door for new opportunities within the company as well. My new found time post transition will be spent working on new strategic projects that I am excited about.

It’ll be a new era for me starting Q4, but I am just as excited as I was since I joined.

Celebrating the wins

We’re in celebration mode at Secfi right now. Our Amsterdam team went on a boat cruise and our San Francisco team is preparing to go out to dinner shortly.

It’s been a big quarter for us and we wanted to reward the team accordingly. I’m a big fan of celebrating wins as a team. Startups are hard and we all work our asses off to make sure our company succeeds.

It’s really important to take a step back often and acknowledge our accomplishments as team. Goals at startups are constantly being raised every month/quarter/year and when we achieve these goals, it needs to be celebrated as such.

We’ll celebrate big tonight, rest up tomorrow and then start all over again on Monday.

Secfi HQ

We’ve got nearly the entire Secfi U.S. team here in new San Francisco office this week.

The office is huge but still a work in progress as we work to get settled in. It’ll be an amazing headquarters for us. I’m excited to host clients, investors and more to our office as we grow.

While I’ve never been a stranger to remote work, it has been a weird year and half during the pandemic. We weren’t able to meet any new hires in person or host any team events obviously. There’s a level of camaraderie that you just get from meeting in person and I’m glad that we now have the opportunity to do just that.

While most companies have given up their offices and gone fully remote, we decided to go with a hybrid approach. We felt that having a home base where people can come visit and people can collaborate would be the best for a team like ours.

Of course, there’s still plenty of flexibility available as people are not required to come into the office at any point. From what we’ve seen and heard, people like coming in from time to time when we have events or special meetings.

It’s been great to collaborate and brainstorm. Having teammates just walk up to my desk and ask a quick question is much better than the dreaded Slack message. I’m looking forward to doing much more in-person work in the coming months. It’s about time.

The electric scooter revolution

Electric scooter companies like Bird and Lime got dragged through the mud when they first launched. People complained that they were a public nuisance and ruined city sidewalks. Bystanders loved to throw the scooters into lakes or the ocean.

Then there was the whole fact that the margins didn’t really make sense for a company like this to exist. They were the blunt end of a lot of jokes in the media. Yet, more scooter companies were launching and there were even startups that provide infrastructure to start your own scooter company.

Electric scooter companies quickly became the poster child of reckless VC funded growth. Then of course the pandemic happened and these companies went to $0 in revenue overnight.

I’m not here to say any of the above is untrue. They are valid concerns and I do share the sentiment that this may not be a sustainable long-term business model. With all that said, these electric scooters have been a net positive for San Francisco (and other cities) as whole. We have additional forms of transportation throughout the city that is environmentally friendly and fun for the passenger.

I have personally been riding these scooters into work almost every day at the fraction of the cost of a Lyft. They make my life and commute much easier and enjoyable. Today, I signed up for a Lime monthly pass.

Many VCs like to say that they are investing in companies to build a better future and I believe companies like Lime are doing just that.

These companies have a long way to go to be a sustainable long-term business, but before we drag these companies through the mud some more, we should all acknowledge that these scooters have been positive as a whole for residents and society.

The lifeblood of this country

I got a little emotional on my commute home today. I took a running class at my gym in downtown San Francisco and was too tired to Lyte bike or e-scooter home so I decided to try to find a bus. Google maps took me to Yerba Buena for a 70 “blue” bus. I had no idea what the heck this bus was. I grew up in San Francisco and rode MUNI buses and trains almost every day but this was a foreign service to me.

After some Googling, I figured out that this was something called Golden Gate Transit which connects SF and the North Bay. I had no idea this existed. Well, I tried to figure out how to pay for this said bus and it took me to multiple web pages and eventually found out that I needed a Clipper card. I didn’t have mine on me so I had to download an app.

The bus arrived and I got on while still trying to figure out how to load my credit card to my Clipper app. The bus driver was great about it and still let me on. After 5 more minutes, I was able to figure it out. This all took me about 15 minutes and I grew up here.

This is not why I got emotional of course. I wrote this long and uninteresting story because as I got on a bus, this guy next to me who barely spoke any English was also trying to figure out how to ride the bus to San Rafael. He was young, clearly didn’t grow up here and was struggling to figure out the app with his little English. Lucky for him, I was going through the same and was able to help out.

I got a bit emotional as I realized just how difficult life can be for a young immigrant. I don’t know much about this guy or his story, but I instantly thought of my Dad who was sent to San Francisco when he was 19 with minimal English skills. Unlike myself who grew up in a comfortable situation in San Francisco, my Dad was forced to leave his home and had to make it a brand new place pretty much on the other side of the planet.

Immigration is what makes this country special. It pains me to see the anti-immigration sentiment that’s been vocal in recent years. As if life isn’t hard enough for an immigrant who just wants a better life, they have to deal with people in this country who don’t want them here. That kills me inside.

That point where it no longer feels like a startup

Today I got a tour of our office that we’re currently renovating. Our SF and Amsterdam headquarters have been out of co-working spaces since we started Secfi. This office will be the official first office we have complete with Secfi decorations, branding and our own personal touch.

It was surreal getting a tour of the office today. It feels like a culmination of our hard work is starting to pay off. I joked earlier today with our CEO and co-founder that the company is starting to feel like a real legitimate company finally.

Next week, we’re going to have close to 30 of our U.S. based employees in the office together. Combined with our product/engineering team in Amsterdam, we’re starting to get close to the 100 employee mark. I suspect that we will hit that mark before the year ends quite easily.

All this is pretty crazy to see. I started as one of the first employees (I believe I’m officially 7) and the first US employee. At one point, it was myself in a co-working space in SOMA. Now we may very well be in a position where we’ll be onboarding someone new in the office perhaps multiple times a week.

By the definition of the term, we are very much still a startup, but it sure doesn’t feel like a startup anymore. That’s obviously a product of our success and growth is something that every company should aim for, but it definitely feels a bit weird. I think it’ll continue to feel weird for awhile. Perhaps by the time it feels normal, we’ll be at 300 employees.

Home

This past weekend I was in Michigan watching my Washington Huskies take on Michigan. It was yet a second pathetic performance by my Huskies in a row. It’s clear that our head coach Jimmy Lake is in over his head. Since taking over about two years ago, he’s been arrogant and preached championship football.

Since then, we’ve had recruiting mishaps, weird assistance coaching hires, multiple coaching gaffes, a loss to a FCS school and an embarrassing blowout on the national stage. It’s been frustrating and I don’t really see a fix anytime soon given the large contracts we have in place.

With that last trip, my crazy summer travel schedule is officially over. The “Roaring 20s” have been filled with travel and celebrations. It’s been a blast, but I’m exhausted and excited to be home for the foreseeable future.

We’ve got a big agenda for the next 3 months and I’m really excited. Over the last few months, we’ve been on hiring craze. Next week, we open our headquarters in San Francisco and have the entire US team in town. I wish we could have the Amsterdam team in town as well, but it’ll be amazing just having a big work gathering again.

It’s time to focus on work and end the year strong. I can’t wait to shift my focus.

Alts everywhere

I was back at work today after the long weekend and taking Tuesday off to just relax. Long story short, I felt amazing and it was the most energetic and productive I’ve felt in a long while. Like they always say, you don’t really know you need a vacation until you have a vacation.

One area that I’m tracking quite a bit is alternative investing platforms. No I’m not talking about just NFTs although that is part of it. I keep seeing new platforms pop up left and right offering investments in fine wine, trading cards, cars, designer bags and of course, art. Hell even Pokemon cards are making a roaring comeback.

I started watching some of these alternative investing platforms starting back in 2018 when there seemed to only be a few. Now I feel like I get fed ads for one on every podcast or newsletter I subscribe to.

Of course a lot of these platforms exist because of the times we live in today. There’s too much money in the system right now and people are finding pretty much anything to put their money into (see NFTs).

All that said, I do believe in the future of alternative asset investing primarily due to the trend of fractional investing. While the average American may not have (or should) spend $100k on a fine bottle of wine that appreciates over time, 100 Americans may invest $1k to partially own that bottle of wine.

The rise of fractional investing has allowed Americans to rethink their portfolios as they now have access to these investments that were previously only available to the ultra wealthy. On top of all this, it’s just fun to own a piece of a collectible.

I’ve got a few (small) investments in various assets and have had a lot of fun on some of these apps lately.

Sleep debt and being okay with doing nothing

I’ve slept in late the past two mornings. Today, I got up went to lunch and then came back and took a nap. This is the most I’ve slept on a weekend in recent memory… maybe since my college days. It’s yet another sign that my body is absolutely beat.

The sleep debt has definitely caught up to me. While I’m not happy that it’s gotten to this point, I’m glad that I recognized it and have been actively trying to address it.

On a normal weekend day in New York, I would’ve probably got up and spent the day out in the city. Today, I spent most of the day relaxing and watching golf in my hotel room. I’ve got a wedding tonight, and I wanted to rest up for it so I’m not running on fumes tonight.

It’s been a challenge for me. Over the last few years, I’ve programmed myself into thinking that I always need to be doing something. Whether it’s working, sightseeing, working out, or attending events, I’ve always felt the need to be up and about.

This is the outcome of years of bad habits. I now need to learn how to rest and recharge. As silly as it sounds, I’ve had to tell myself multiple times today that it’s perfectly okay to be doing nothing. It may seem small, but for me it’ll be a big win going into this wedding well rested.

Inflections

I slept about 12 hours last night. An absolute crash from my red eye flight and my body telling me it needs more rest. I’m feeling pretty darn good today after a week of feeling meh.

I’m currently listening to Mike Maples Jr on Invest Like the Best with Patrick O’Shaughnessy. I’m only through the first bit but it’s a fantastic listen so far. The podcast starts out with Mike discussing inflections and why founders should be looking for inflections not startup ideas.

Mike’s idea behind inflections is that rather than building for the gaps in the world we see today, you want to be looking for inflections which will allow you to build towards the future. Certain inflections such as the rise of smartphones and GPS in smartphones allowed Lyft to change the ride sharing world.

This idea is a big reason why I joined Secfi in 2018. We saw the current world of startup stock options which was broken, and we saw a future where companies were trending to become more employee and equity friendly. We saw an opportunity to shape the future of stock option exercises and liquidity because of this inflection.