Back to basics

I had a nice short weekend trip up to Bodega Bay. I played a round of golf on Saturday and it was ugly, as expected. I took my first lesson in a long time last week and I knew that things are going to have to get worse before they get better.

I had a been in a stagnant position where I just couldn’t get over the hump. I was constantly making swing changes that would help for a bit, and then unravel later on. Which would lead me to my next “fix”. It was a terrible cycle and I was fed up with it.

I’ve had a lot of fun trying to teach myself a golf swing. Learning about swing mechanics and trying to be my own golf coach is definitely going to help down the road. But in the meantime, I needed to call in the pros here.

My first lesson revealed that I had some fundamentals horribly wrong. The last few months, I had diagnosed a lot of my issues correctly but didn’t realize the fixes were simply fixing fundamentals. Instead I was applying more complicated fixes that made things a whole lot worse eventually.

I can’t help but think how many solutions to problems out there are simply just getting back to the basics. I worked in consulting for 3 years and we were often brought in to fix “complicated” problems. While we hated to admit it because we were judged by our billable hours, most fixes were relatively minor when you broke the actual problem down.

Partnering and competition

As startups grow, there’s a lot of partnership opportunities with other startups and companies. These partnerships need to be mutually beneficial in order to work. You need to give as you receive in order for these things to work out correctly.

Unfortunately, one trend I’ve seen over my few years is that a lot of startups are overly protective when it comes to partnering. They view other startups as threats or competition rather than partners. That of course can be true, but more often than not, these things are not a zero sum game.

I think a lot of this has to do with the fact that most startups are inherently neurotic. They’re coming in to disrupt an industry and they view it as a race to the top. Founders often have a winner take all mindset. In reality, very few industries fall in the winner take all category.

I’ve tried to keep an open mind with a lot of our partners, despite the fact that there may be some overlap with potential customers. That has led to some great partnerships where we share the pie, but quite often it’s a bigger pie to start with.

Slowing down and enjoying the ride

When I was first started my career at PwC, I was that stereotypical hungry and young employee who was gunning for promotions and career advancement as fast as possible. I pushed to get promoted to Senior Associate early in 1.5 years where the standard time was 2 or 3 years. And then I tried to gun for promotion to Manager again at the 4 year mark which was about 2 years earlier than average.

I worked hard and lots of hours. I don’t regret it as the more I gave into my job, the more I got out of it. I learned quickly and got the attention of a lot of senior leaders. I was okay with it. I was young and energetic, ready to learn and quickly move up the corporate ladder.

When I was up for early promotion to Manager, I felt that I had deserved it and worked harder and was more productive than other Managers. I still believe that is true to this day. Yet I didn’t get the promotion. The feedback that I got was that I was still a bit immature but largely that they didn’t want to set a precedent that people can get promoted at 4 years. I was devastated and angry.

When I had a chat with my partner about this, one of the things that he said to comfort me was that I needed to slow down a bit and enjoy the ride more. He emphasized that life and success wasn’t all about getting promoted as fast as possible. While acknowledging that he appreciated my effort, he also said that I was missing out on a lot and needed to refocus more on learning and just having fun with life.

He was right. I was so focused on getting promoted and grinding out work as fast as possible. And I wasn’t enjoying it during some of the best years of my prime. I think it’s perfectly okay to be career focused, but nowadays, I also make sure that I’m enjoying the ride as well.

Resilience through the bad times

My freshman high school football class was highly touted. When our group came in as freshmen, we had a lot of promising players and the varsity coaches immediately took notice. I joined with the rest of the group my freshman year and barely played my freshman year. My body was still developing a 5’4” 135 pound skinny kid is seldom going to find playing time.

It was one of the hardest years and my first introduction to hard work. Practice kicked my ass and I didn’t get to play. We had a good year overall on junior varsity, but it was a struggle and I thought about quitting many times and again after the season ended. Was all this worth it? I ended up sticking around and working hard. I finally hit my growth spurt and I was 5’10” and 160 pounds by the time sophomore year started.

I ended up starting the entire year but it was a horribly disappointing year in terms of performance. A lot of my touted classmates got pulled up to varsity as sophomores. The coaches were first year coaches and really had no business coaching a team. I can’t recall exactly, but I think we won a total of 4 games and lost a lot of close ones.

After the season, I had a lot of doubts once again. Varsity was going to be even tougher with tougher competition and coaches. They were going to demand a lot more out of me and the team. I had a lot of teammates who felt the same and a lot of promising players ended up quitting after sophomore year. My resilience was being tested once again.

I ended up sticking around. My junior year we lost in the championship game, the famous Turkey Day game in San Francisco. We exceeded expectations with a lot of players who graduated the previous year. We fell short of our goals, but it was a magical season that taught me a lot of life skills. My senior year we ended up losing in the playoffs after another amazing season. I ended up making first team all San Francisco and it was probably the biggest accomplishment of my life at that point.

That was over 15 years ago now and I’ve had a lot of time to digest things. The biggest lesson I learned from playing football is that you need to go through the tough times in order to reap the benefits of the good times.

In today’s day and age, employees seem to be flocking to greener pastures as soon as they can. It’s something that bothers me. I understand that work is different than high school sports. You have to take care of yourself and your family financial so it’s not a perfect comparison. But quite often, when I feel down in this tough bear market, I think about what would have happened if I quit after my freshman or sophomore year.

I would not be who I am today. And I would not have reaped the benefits of those 2 amazing years on varsity my junior and senior year. I wouldn’t trade those years for anything.

Hopefully most people who decide to stay loyal to their startups in this tough environment will be rewarded on the back end when things come back up.

The future of work from home

I’m starting to become more and more convinced that the future of work will be largely in office again or at best, hybrid. Some companies can pull off the remote work culture, but I think the majority of startups and companies will start to see the benefits of being together is too great to ignore.

I hate to say the fully remote world is a ZIRP phenomenon but there’s definitely some truth in that statement as well. Employers can and need to demand more in this current environment.

The days of asking for fully remote work, demanding San Francisco salaries and equity while working in exotic locations like Tulum may be coming to an end. I’ve spoken to quite a few engineers and friends who are planning those days to end officially by the end of the year.

For now - they’re still enjoying what they can right now. I have a few friends looking to do some bigger trips this summer to take advantage.

Mother's Day

I celebrated Mother’s Day yesterday by visiting my mom’s grave. It’s been over 25 years that my Mom passed away due to breast cancer. It’s been amazing to see the progress in technology and research since my mom was diagnosed. If my mom had been born 15 years later, she likely would have caught the cancer earlier and in all likelihood still be alive today. Although that’s admittedly a sad thought for myself, I’m happy that more people have not had to grow up without a mom.

I was 7 when my mom passed. Growing up with a single parent father definitely had a major impact on my life. I was in a relatively fortunate position to have lots of family, friends, and resources to overcome any major issues. But it was still hard at times. I can reflect back to many moments in my childhood which were difficult.

I know my mom would be happy with the way that I’ve grown up. I’ve lived a blessed life and I know that was the only thing my mom wanted for me and my sister. Last year, I married Sophia whom my cousin said reminds me of my mom. That was a special moment for me during my wedding.

Unfortunately my time with my mom was short. It was even shorter for my younger sister. I hope that the best way to honor her is to live life the way she wanted me to live. It’s something that I’ll always keep in mind as I grow older and perhaps start my own family.

Roam

Our team has been trialing Roam HQ for the last week. The tool is meant to be a virtual HQ where each person has an office that you can knock on to quickly chat. We also have meeting rooms with video as well as a lounge for all of us to hang out in.

We wanted to try out this new tool as a way to stay better connected and enable more collaboration. Being mostly remote, a lot of us missed the ability to just pop into someone’s office or quickly chat about something. Those interactions have largely gone into Slack messaging which could be counterproductive.

So far, things have been great. We’re chatting more and Slack has calmed down significantly which has helped my anxiety personally. We’ve used the tool to connect and have fun with each other as well.

We’ll see how things go in the next few weeks, but I’m optimistic that this is a tool that can really help us work better together.

Generative AI startup losers

It feels like every day, I see a new generative AI startup or project being launched or announced on Twitter. AI startups have single handedly been the reason why VCs have deployed any capital in the last year. The hype is on.

It’s yet to be seen where the winners in the AI stack are going to win, but I have a hunch that the losers are going to fairly easy to spot. My perhaps not so hot take is that most projects that are effectively generative AI wrappers or lenses for consumers probably are shooting themselves in the foot by raising VC money.

Most of these projects raised money when revenue was skyrocket as people were experimenting. Getting an AI interior designer for your living room or gathering legal research are all great things that consumers want. But many of these are features that will be built by larger products that already exist.

Once these features are built into your every day applications such as Photoshop or Notion, many of these startups will unfortunately fail or have to be sold for less than the founders hoped. On the flip side, many of these startups can effectively be run bootstrapped and print money - it’s not a bad gig to just be a profitable small business!

Unfortunately, I think the allure and prestige of being a VC backed founder has been too much for most of these founders to pass up.

VC job preservation

A month ago, I spoke to a friend who works in VC and he mentioned that he’s basically just in job preservation mode.

I also just saw this tweet from Ali Moiz, the founder of Stonks.com:

Ummm...quite a few VCs seem to have lost or changed their jobs. Lots of Associates, Principals, even a few Partners. I sent out a bunch of emails to stonks users today, and seeing dozens of auto-responders specifically from investors that are "no longer with the firm"

It’s a really tough time in the industry. A lot of firms are sitting on a ton of dry powder but have not been deploying for the last year and a half. I know quite a few prominent VCs who have done 0 deals in the last year. This is of course partly strategic as the tech sector goes through a valuation reset and investors are waiting to see where things land.

A lack of deals means a lack of work for a lot of people who work in VC. No one is immune in this down market.

The state of Twitter

It’s been over half a year since Elon took over Twitter. Back when the deal was getting finalized, I was cautiously optimistic about the acquisition. As a user, I thought that the platform could use a lot of new features that would take an energetic new management team. I was also worried that one of the most important platforms would fall into the hands of an erratic billionaire.

Taking Elon out of things, the platform in my opinion has objectively gotten worse. I have never been great with social media but Twitter was my go-to social media platform for the wealth of information and ability to make meaningful connections.

Nowadays, the platform is largely a waste of time for those who don’t pay for Twitter blue. Tweeting as a non-paying user is largely worthless as the tweets are severely nerfed. By forcing people into paying users, Twitter has lost a majority of their best content.

My timeline is now filled with blue check mark tweets… half of which are more or less ads disguised as content. The only thing better so far that I’ve seen is the parody accounts of people buying Twitter blue to impersonate real people. That was been hilarious to watch.

I have no idea where this is headed. Elon has proven a point in that you probably needed only 20% of the headcount to actually run Twitter, but we have yet to see it develop into anything remotely what he has promised. Maybe he’ll actually turn things around or maybe he’ll turn his $44B prized acquisition into nothing.

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.