The worst shot of my golf career

I played golf on Sunday and might’ve hit the worst golf shot in my short 3 year golf career. On 18 at Presidio, I was about 180 away and in between clubs. I was tired and didn’t want to chunk my shot like I had been on the back 9 so I took the higher club and decided to swing harder. I thought last hole, what the hell.

I overdid things and ended up cranking a high drawing… okay high hooking shot straight onto the cart path. The ball bounced on the pavement and flew up right over a large group of people by the club house taking a photo after some sort of event.

I narrowly missed the group of ~25 as the ball bounced short and flew right over them and the clubhouse. Luckily no one was hurt except my ego and my confidence on the golf course. I was very quick to get to the parking lot and get out of there.

It was a culmination of a terrible weekend of golf. My swing is in complete ruin right now as I tried to make some major changes last week. I rushed things and didn’t get enough practice nor instruction to make things work. Instead of playing some rounds, I should’ve been at the range some more.

In golf as in a lot of things in life, you need to go backwards before you can move forward. I’ve been delaying the inevitable with small patches of fixes here or there, but it’s about time I take a step back and reconstruct my swing the right way. That’s going to require a lot of time.

State of secondaries

We’ve spoken to a bunch of individuals looking for liquidity lately. Almost everyone will ask me for my take on the secondary markets. Here it is:

There are buyers out there right now, but they are largely opportunistic and taking advantage of people desperate for liquidity. And there are a lot of people desperate for liquidity. Despite looking for liquidity, a lot of sellers have held firm and have decided to wait for the market to rebound.

A lot of people are expecting things to get better in the next year. And they will. But what they’re also not realizing is that multiples will not come close to where they once were. Coming that with slowing revenue growth in startup world, and it may take years for companies to get back to previous valuations.

I don’t expect sellers to wait much longer. I expect volume to pick up significantly in the second half of the year as people round out year 2 of the bear market.

Culture and morale

Since the market started turning in 2022, we’ve been focused as a team on team morale. Anyone that works at a startup right now has been feeling the pressure. Rising interest rates have dried up the capital markets. Sales cycles have slowed. Nearly every startup and tech company has gone through at least one RIF over the last 18 months.

It’s easy to be down right now. Bonuses and salary increases have dried up. Equity grants have dropped significantly in value. I’ve personally gone through a lot over the last 18 months and it’s undoubtedly has been the hardest period in my career. Knowing the challenges that we’ve faced and will continue to face in this bear market, we’ve put an extra emphasis on doing the best we can for our people.

First, we want to make sure that growth does not stop. We’re placing extra emphasis on supporting our people in achieving their personal and career growth trajectories. Everyone at the company is still working through career and growth plans.

We are also giving our people the opportunity to expand out of their traditional comfort zones. Bear markets like these are a great time for employees to take on new strategic projects.

On top of all this, we’re placing an extra emphasis in culture and camaraderie. We’re all in this together. Your culture is what happens when shit hits the fan and shit has hit the fan a lot over the last 18 months. We’re doing a lot of work to ensure that our culture and values do not disappear even when times are rough.

False promise of liquidity

I was chatting with some people in my Washington Huskies fan Discord group about recruiting kids in the day and age of NIL. Since a couple years ago, schools/fans can more or less legally pay college athletes to play sports at their school. We had a funny discussion on whether each person would be a halfway decent recruiter, given that pretty much none of us work in sports or have played more than high school level football.

I came to the conclusion that I would be better than average given my day job which consists of building relationships, negotiating, and yes giving money to people. Someone else made a joke about how brutal it would be speaking to a bunch of kids (and their parents) asking for money upfront without actually earning it yet. I had a good laugh and then realized just how similar this is to startups and tech.

We get a lot of inbound and requests from founders and employees looking for liquidity. That should be no surprise, because I also like money. However I’ve noticed that over the last few years, there’s been such a large disconnect with reality when it comes to liquidity. For example, I had a founding employee reach out last month looking for liquidity on his shares after reaching a collective $1M in revenue. Yes, that’s collective.

I don’t blame individuals for looking for cash to better their lives, but I do believe that the last few years of the bull market have unfortunately created an unhealthy promise that you join a startup and you’re guaranteed liquidity at some point in time. The reality is that almost all startups fail and most startup shares end up worthless.

Liquidity comes when your company has hit certain milestones. ZIRP unfortunately moved those milestones earlier and unfortunately we now have a situation where founders and employees expect that to be the norm. That is no longer the case and it won’t be going forward, yet there is still a perception among employees that it is so.

I don’t believe this is healthy for the startup ecosystem in general. The get-rich-quick world is now over and people need to get back to joining startups for the right reasons.

Missed hires

My first hire at Secfi was a terrible miss. I had thought I knew what I was looking for in a candidate, but in actuality, I overindexed on background and relevant experience. And I severely underindexed on hustle, initiative and fit.

Background and relevant experience is important, don’t get me wrong. You can’t completely ignore that and expect to find a good hire. Relevant experience more so than background. In terms of background, I don’t pay too much attention to school, major, etc. Most of the high performers I hired do not come from Harvard, Yale, or Stanford.

Relevant experience is important depending on the role you are hiring for. There are just too many roles where experience is major leverage. I do believe that relevant experience may be a lot less relevant for certain roles such as Business Development. I’ve hired many people for my BD team that have not had direct BD experience and they have been fantastic.

The biggest thing I look for in a hire by a large margin is hustle and initiative. At a startup, you need people who can go off on their own and operate without guidelines or a playbook. In most situations at a startup, there are no playbooks as you’re inventing it as you go. Someone needs to be self-motivated to hustle to get shit done, or you won’t be successful at a startup.

Fit is where the magic happens. In a sense, everything goes into “fit”. But when I look for fit for my team and our company, I simplify things and look for people who have the same goals and mindset. The main goal is to grow this company - individual accolades and achievements come along with that, but we need to be of the mindset that growing the company comes first.

In terms of mindset, I look for people who want to operate in a team environment. Growing up playing sports, I believe that the most successful teams operate with a championship mindset. That is putting the team first and working together. I can write paragraphs on this, but that’s hopefully a future post.

Missed hires unfortunately happen often at startups. It’s easy to like a candidate for the wrong reasons. It’s taken me 5+ years of hiring at Secfi to really hone in on my methodology and it has worked ever since I made that first missed hire. It’ll continue to evolve over time and change as our startup’s needs change as well.

Burnout, time-off, and true rest

It’s Monday morning and I feel as motivated and positive as I have felt in a long while on a Monday. My weeklong staycation aka my “recharge week” has seemed to work. Comparing how I feel today to two weeks ago when I all I felt like I wanted to do was crawl back into bed is night and day.

The last two weeks have thought me a lot about myself and work. I realized just how real burnout can be. I’m not sure where my level of burnout ranks on the spectrum, but I know that I largely had been ignoring the signs for months before I finally did something about it. Now that I have experienced that level of burnout, I know much better to spot it and prevent it from ever getting to that level.

The only remedy to cure burnout or exhaustion is simply just to take time off to rest your body and mind. That’s no secret obviously, but one thing that I’ve come to realize as well is that time-off isn’t made equal. I love to travel and while traveling is great away to get work off your mind, I also realized that it’s not always the best way to recharge and rest.

My travel schedule is often filled with early morning wake-ups, activities, etc., not to mention possible jet lag. That can be great, but can often be exhausting in it’s own way. I’ve heard the saying that “you need a vacation to recover from your vacation” quite often. Quite often after a trip, I come back to work and I’m even more tired.

This is an important insight for myself. When I take time-off, I need to put in proper time to also rest and recharge. If I don’t get that from a trip, then I need to schedule more relaxing weeks to actually get some rest. Taking time-off in itself does not cure your burnout or recharge your batteries - you need to actively rest.

For myself, the staycation was exactly what I needed. I didn’t need a trip to a foreign country, I just simply needed some time to sleep and get my mind away from work. Setting my intention for my time-off did wonders for me.

In the future, I’m hoping that I won’t need too many of these weeklong staycations to curb my burnout. Prevention is the ideal case. But in the occasion that I do run into it again, I know exactly what I’ll need.

Reflections on my recharge week

Overall, I had a great week off. I slept a lot, did more than I expected to, and learned a good deal about myself and my habits. What is yet to be determined is the actual impact on my potential burnout. As I write this on Sunday afternoon, I feel good and rested. While I would be lying if I said that I was 100% stoked to get back to work, I do feel a bit more motivated and excited to get back to it.

I’m still in a bit of vacation mode so I don’t have a burning desire to put my thoughts in a coherent blog post, so I figured I just write down a few observations and thoughts to memorialize my week.

• Overall, this is the most positive I’ve felt in recent memory. Even after a great vacation, I am usually in a sluggish mood the day before going back to work usually due to travel. I need to look into doing a staycation more often. I feel more recharged than I do when I travel by a wide margin.

• On sleep - I was in bed nearly every night for over 9 hours. I had no issues sleeping or sleeping in until past 9am. It was a bit of a unique feeling going to bed at home knowing I didn’t have to be up for anything for so many days in a row. It helped my anxiety and sleeping was a lot easier. I need to do a better job turning my brain off from work before sleeping.. it’s clearly the cause of my sleeplessness.

• It felt amazing to be able to sleep in as much as I wanted, but I found that it wasn’t much easier getting out of bed. I still woke up a bit sluggish and would need to push myself to get up. I could’ve easily stayed in bed until Noon every day. I wonder if this was just me being lazy or yet another sign of burnout.

• My body feels great overall. I didn’t work out once and while I got my steps walking in quite a bit, my body physically feels rested. I need to take more breaks from working out so my body can recover - it’s a net positive overall.

• There are so many fun things to do. I wrote a bit about this on Friday, but I quickly rediscovered how much fun I have even if I am by myself. I need to live more and do more fun activities, even if it interrupts my daily routine. Occasional spontaneity is good.

• I found it difficult to stay away from work completely. I told myself I would only take one work meeting, but I ended up working perhaps 30-60 minutes at least each day. It wasn’t my plan, but I felt that it was still hard to completely disconnected. The good news was that I didn’t feel stressed by the little work that I did.

• On work… I took a week off and everything is fine. My team is amazing and is more than capable of handling everything. My clients understood with some things being a bit delayed. As much as my type A personality has me feeling like I need to get everything done ASAP, I’ve learned that not everything needs to be attacked with the urgency that I have been applying.

• The anxiety from constantly checking my phone and ensuring I respond to everything ASAP is one of the worst habits I have. It got to the point where I was checking my email/Slack on my phone even when I was out for 15 minutes to pick-up lunch. It’s not healthy and not productive. I need to live in the present more.

Getting bored

As I was planning my recharge week, I kept telling my friends that I wanted to spend the week “getting bored”. I had the idea that I was going to take the week off, do next to nothing, and just get bored. I would go to parks to relax and read books, maybe go check out a few restaurants, and sleep in.

As I wrap up my recharge week, I’ve actually had the opposite experience. I found that I had too many fun things that I wanted to do. So far this week, I’ve visited an old friend in Petaluma for the day, explored Golden Gate Park and went to the Giants game. I’ve done a lot of reading in parks as well. I’ve had a fantastic week so far.

I didn’t think I would be so excited to just stay in San Francisco for the week largely by myself, but here I am longing for more time to watch a couple more movies, explore another part of the park, and read two more books.

The funny part about this realization is that I had once mentioned that San Francisco is a rather boring city and I even complained that there weren’t that many activities. Well I realized that the city is not the problem, I was the problem.

I think I’ve been so caught up in work and my daily routines that I’ve kind of lost my sense of adventure and spontaneity. I’ve been programmed to work 10+ hours on weekdays and my only leisure has been to go to the gym and workout. I then get to the weekends barely cognitive and I’m operating at 50% speed the entire weekend and often doing next to nothing.

I’ve planned my life around work. This is the opposite of how things should be and probably a big driver of why I pushed myself so close to burnout. Going forward, I need to live more. Getting to the weekend week in and week out barely functioning is not a sustainable practice going forward.

Glorious day

My recharge week continues with another great day. I woke up a bit early today but just took an easy morning. I told myself that this would be the only morning where I’d allow a work call to happen so I did about an hour worth of work and called it good.

I decided to have lunch with my Dad and stepmom. It was short but it was nice to catch up with them on a weekday while my little sister was at school. We could have more adult conversations about life.

Afterwards, I headed to Golden Gate Park. I had this day earmarked as my big park day. I planned to just be outdoors and hang out. I started my adventure in the Japanese Tea Garden and then headed to the Botanical Gardens.

I had forgotten how much I love the Botanical Gardens. Every section is like a new adventure with plants from a different area of the world. It’s one of my favorite places in the city, but I hadn’t been for perhaps 10 years… go figure.

Right by the entrance, I found a duo doing a soundbath and decided to set a blanket down and join in. It was a perfect hour of relaxing in the sun. The rest of my day was spent exploring the gardens.

Probably the best part of today was just realizing how great doing next to nothing feels. For hours at a time, I could just relax in the park looking at plants or the grass. There were no outside pressures, no phone ringing, no emails… it was simply just living and it was glorious.

Everything's going to be alright

I’ve had an amazing kick start to my recharge week. I really didn’t do much yesterday… I grabbed a nice lunch and went to a few grocery stores which I find therapeutic. Then I read at Dolores Park for a bit, grabbed some ice cream, and then read some more over a cup of tea.

My mornings have been a slower start for me overall. I’m still waking up a bit tired and I find myself wanting to lay in bed for an hour or two just being lazy. I’ve found it oddly difficult to just be okay with staying in bed and doing nothing — my mind has grown to be wired to get up and do something. I’m taking it as a sign that my body is telling me to rest. I’m going to do just that.

One thing that’s surprised me is that it’s been oddly easy to not check my phone or email much. I’ve tried to take an out of sight, out of mind approach to things going on and it’s been working. It helps that I have an amazing team that has been handling everything. Every time I’ve checked in, things have been moving along perfectly fine.

I’ve realized just how much constantly checking my phone and being stressed about things has impacted my day to day life. I’m often going through the week without living in the present. It’s time to get back to living in the moment. Everything’s going to be alright.

LinksDAO fun

It was a gorgeous weekend here in San Francisco. It was very much welcome after an abnormally cold and rainy winter.

I got a round of golf in at Santa Rosa Country Club which was awesome as I was able to book the tee time via one of the perks of being a LinksDAO member. I put out a bat signal to our local Bay Area LinksDAO group chat looking for a 4th and got paired up with a good dude name Lyle.

The LinksDAO project has far exceeded all my expectations. I bought in on New Year’s Day in 2022 with the hopes that it could turn into a fun virtual “country club”. In the year or so since being active, the DAO has already bought a golf course. I didn’t think things would happen that fast candidly.

Beyond the actual purchase of a golf course, I’ve had a ton of fun in the community. I joined the LinksDAO golf event at Harding and had a great time meeting some awesome people. I’ve played a few rounds with some others with the project as well.

I believe that this is what these NFT projects are all about… creating a community around a common goal or belief. When I gave myself an allocation to buy into these projects, this is exactly what I was looking for. I wanted to participate in the web3 craze and see the potential power of crypto. Bear market and valuation of the NFT tokens aside, I’ve gotten way more out of this project than what I put in. That’s all you can ask for.

Wrapping up

I’m excited to wrap up work today and get to my week off. I don’t have a lot of plans by design. I’ve thought about flying out to Hawaii for a few days to relax on the beach and see my sister and friends. Tickets and lodging are cheap right now and being out there in the sun sounds nice.

I’ve also thought it would be real nice to just stay home and do nothing. Maximizing my rest and relaxation is my first priority right now, so I need to figure out where I can do that best.

I know what I won’t be doing though and that’s working. I’m fortunate to have an amazing team and colleagues who were more than happy to pick up while I’m out. I’ll probably also aim to stay off the caffeine and alcohol as well. As much as I like a nice cocktail in the evening, I feel like it would be counter productive to my goal of resting.

I’ll probably get put together a list of outdoor activities and a good reading list. It’s going to be a great week.

Remote flexibility

There’s a never ending debate on office versus remote work. My stance is that there will never be a right answer as everyone likes to work differently. Just like everything, there’s pros and cons to being fully remote or fully in the office. Every company will just need to decide where they fall on the spectrum and decide what is best for them and their company’s culture.

At Secfi, we have taken a hybrid approach. We have an office in San Francisco, New York, and Amsterdam. But we also have remote employees scattered throughout the country. Our Amsterdam office is largely in-person as most people come in nearly everyday. In the U.S., if you live in SF or NY, most people are coming in a few times a week.

The model has largely worked for us. We are technically a remote company as the team was built as split between the U.S. and Amsterdam already so we had some protocols in place to enable that collaboration between the locations.

One major positive of the hybrid model that I’ve seen since the pandemic is that this promotes flexibility. As we are not bound to the office from 9-5, people can take time during the day to take care of personal needs whether that’s picking up kids, going to the gym, etc. I’ve always encouraged this to my team.

For example, I like to take a break during some afternoons to go on a run or go to the gym. Sometimes I have an empty block in my schedule in the late morning or mid-afternoon of the workday to go workout and take a break. It’s been great for my mental health and makes me more productive when I do get back to my desk. I know some have taken the mornings to do a bit of skiing or surfing as well.

I think that this is the future of remote flexibility. We have a level of trust in our employees that they can do this and still get their work done. In my opinion, it creates happier employees. We do not spend time policing people to be online at Slack at certain hours to be instantly responsive - that is counterproductive.

Of course there’s limits to all this. You can’t just decide to take every morning off of the week. We only have limited time in the day to collaborate on everyone’s schedule. Flexibility goes both ways as well. Last night, I had to take a call at 10pm. It was not ideal, but I had to make myself available due to time zones.

Building this in our company and teams culture is really important to me. I’d imagine a lot of other startups and companies will be operating the same way soon if they aren’t already.

Relief

Perhaps the most telling sign that I need a break is the immediate relief that I felt once I decided I was going to take next week off just to do nothing but recharge. I had been excited about vacations in the past before. I’ve had some amazing trips lined up in the past and of course I was stoked for them to finally arrive.

But this time it just felt different. Instead of an excitement for adventure, I just felt instant relief. don’t have a great way to describe it besides that my body just screamed “finally!” I’ve never been more excited for a week to do nothing.

I’m not fully sure what I’m going to do next week. I know that I’ll start off by sleeping in every day and plan as little as possible.

Burnout reflection

I wrote yesterday about how I wasn’t feeling great. I was tired and unmotivated despite having a good night of sleep. I’ve taken a lot of time to read, speak to people, and reflect about the state of things over the last day. Perhaps I had been in denial for sometime, but it’s fairly obvious to me that I’m showing signs of burnout.

I think the most perplexing thing about this situation was that this feeling of burnout felt a lot different than the last couple times. I had some obvious signs of burnout during my previous job when I was working 80+ hour weeks for weeks at a time. Back in 2021, we were so busy that I was working long hours and weekends, and it was clear that I was burnt out and exhausted.

Those times felt different, I was clearly overworked and that was directly attributed to the hours I was putting in. I’ve made great strides since then including forcing myself to take weekends off, setting up boundaries on weekdays, finding more hobbies, working out more, sleeping more, etc. In fact, I’m fairly proud of where I’ve gotten in terms of my hours and my overall health. That’s why this time has been so perplexing.

I may be in the best shape of my life working normal hours, but yet I’m showing clear signs of burnout. I suppose I’ve been in denial for some months now. The pattern has been there a lot of weeks. I wake up Monday exhausted and feel as though the weekend drained me, I slug through the day and start to feel better after some exercise. Tuesday I feel better and my mood improves until I hit a wall around Thursday or Friday. I feel great over the weekend and then it begins again.

For awhile, I had thought that it was perhaps due to me staying up too late on weekends and that caused me some sleep issues. Maybe one drink turn into one too many on Saturday night and I blamed the Monday blues on that. But the more I read of others’ burnout stories, the more I realized that the primary reason for me feeling like crap is that I’m reaching burn out levels.

My body and brain have been telling me for some time that it’s ready for a break. I’ve just been ignoring the signs unfortunately. I’ve been largely able to make do with powering through or short weekend trips, but what I need is a longer break to rest the body and mind. I’m going to take next week off to do just that.

Next week I’ll be on a staycation where I don’t have much of an agenda. I’m going to sleep a lot, relax, read and just be a bit of a blob. I’m not planning on making any plans including any sort of exercise or chores… I’m just simply going to treat it as a sick week of recovery.

In my 10 years of working, I have yet to take a vacation like this and I couldn’t be more excited. I feel like a weight was lifted off my shoulders after I decided on this this morning. The one thing I do hope to do next week is write and reflect a lot. I’m hoping it’ll be an amazing therapeutic week.

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.