Cash rules everything around me

The big news of yesterday and the foreseeable future will be the talks of the PGA Tour selling out and taking the Saudi PIF money. There will be a lot more details released over the next coming weeks, but from the surface it appears that this deal was brokered among just a select few individuals. Players and executives on both sides were not aware that anything was happening until it was announced publicly.

Going forward, it will likely be good for the overall game of golf. The PGA Tour gets the cash injection it needs while getting rid of their rival competitor, LIV. Of course, there’s many other implications involved including taking money from the Saudi PIF. I have no desire to write more about the politics of taking money from them so I’m going to move on.

Perhaps a bigger gut punch is to the players of the PGA Tour. Those who stuck around and did the “morally right” thing to not take the money are undoubtedly the ones who are impacted the most by this. The top players turned down huge paydays from LIV to stick with the PGA Tour. They went on stage and did what the PGA Tour told them to do.

Then the PGA Tour went behind their backs to broker the deal. I’d be pissed off too. I don’t really know how this will end up. The players are probably a bit conflicted in many ways. Those that are not top players will welcome the increased pay. Those that are top players will also get a big bump, but at same time, not as much as they would have if they had left earlier.

Just another instance where at the end of the day, money talks. We’ve seen what has happened with college sports since the NIL became a thing. The development of the NBA and NFL into money generating machines has been ongoing for years. For better or worse, sports make a shit ton of money, and the leagues will continue to chase that money.

Cash rules everything around me, dolla dolla bills ya’ll.

AI in everything?

I’ve been reading a lot of pitch decks and watching a lot of pitches from companies in the generative AI space. A big part of this is obviously looking for some great investment opportunities, but perhaps even more important is myself learning and keeping up with the latest AI trends.

There’s a lot of great projects out there, but I can’t help but feel that this feels like the blockchain overhype all over again. Just like when startups were putting stuff on the blockchain just to put stuff on the blockchain, a lot of startups today are adding “AI” to their startup just to say it’s there.

Of course, I am a believer that AI will be in every company in some way shape of form. But I fear that a lot of companies are losing sight of their main product in order just to call themselves an AI company. Everything does not need to be on the blockchain. Nor does everything need to be an AI company.

Weekend wrap-up and ChatGPT in video games

I’m feeling great today after a good weekend. On Friday, Sophia and I had a nice date night at one of our favorite restaurants in the city, Rich Table. Saturday was a full but chill day. I had the best driving range session in recent memory to kick things off, and then a few of us went to the Union Street Fair.

I played golf on Sunday and had the best round in a long time. It wasn’t perfect, but my two swing lessons have gone a long way. I’m back to feeling confident sitting over the ball and my swing is feeling smooth. It’s a great feeling and golf yesterday was a lot more fun compare to the last few times when I felt like I was at rock bottom. I finally feel like I have something to build off of.

This weekend, I also bought the pre-release of Diablo IV. Diablo II had been my favorite game as a kid. I’ve been off the video games for awhile and missed Diablo III, but I figured that I take full advantage of this time and hop right in. My friend Chris and I decided to stay in Saturday night to kick things off.

The game definitely delivers. Like many other RPGs, the world is massive and there are no shortage of fun things to do outside the main story line. The one downside to games like this is that you can spend a lot of time traveling and grinding while traveling from point A to point B. It can be a time suck and when you have limited playing hours before the wife and life starts calling, you want to maximize your time.

At one point I thought to myself that someone needed to make a ChatGPT for Diablo IV players so they can figure out the best routes and angles to play the game. Of course, it sort of defies the point of the game which is to learn and explore things as you go. So maybe this is one area where Generative AI should be stopped.

Slack, Zooms, and Meetings

Prior to the remote vs office debate, probably the most exhausting workplace debate was around meetings, calls, and Slack messages.

I am old enough that the beginning of my career meant that you were at your desk with a phone. And we’d gasp call each other when we needed something. Occasionally we’d send instant messages via our internal system, but phone was usually primary form of communication.

With the Slack era, more and more people started using messaging versus phone calls. It was a welcome change for most people… until unread Slack messages drove people’s anxiety through the roof. We now live in a world of abundance of workplace tools. We have slack for messaging. Slack meetups for quick calls. And Zoom/Meets for longer team meetings. It can be overwhelming.

At Secfi, we recently implemented Roam which is a virtual HQ where you can knock on people’s doors and see if people are “in the office”. It’s largely been a great tool, but the negative feedback we have gotten is almost always centered around the fact that they don’t want another tool for people to contact them.

I used to feel the same way. In my earlier career, I never wanted to be bothered. I wanted to be heads down and just grinding out work or client calls. Messages + internal calls always felt like a chore that interrupted my work.

Then I started managing people and everything changed. What I always tell people who give me this feedback is that unfortunately these communication tools aren’t always for you. They are mostly for your manager(s) and colleague(s) to get stuff from you that they need to do their jobs.

A successful startup cannot run with just individual contributors sitting in silos not talking to each other. There’s other implications that people need to realize beyond their bubble or silo. That is why these tools are very important, despite perhaps being annoyed that people are bothering you.

One of the things that we’re implementing is more guidelines on how we communicate and talk to each other in this ever-growing remote working world. That will help with the anxiety, but the most important thing is having everyone realize that communication is vital, maybe not for them but for everyone else.

The Lasso Way

Sophia and I watched the series finale of Ted Lasso last night. It was bittersweet as it has been one of our favorite shows post-pandemic, but it ended at the right time, in the right way. The show has been a brain cleanse and a reminder that there is a lot of good in the world.

We live in a tough world and society. It doesn’t take much to feel a bit jaded about your life or circumstances. A 5 minute scroll through Instagram can take a huge mental toll on your psyche. It can be really easy to compare yourself to others by money, looks, goods, etc. The bad news cycle perpetuates negative thoughts in our brains.

I know it’s just a silly and albeit corny TV show at times, but there’s a lot to learn from Ted Lasso. I’m not sure if the writers intended this to act as therapy for some folks, but it certainly played part therapist for me.

If anything, I’ll remember that there’s a right way to do things and a wrong way, no matter the outcome. Thanks Ted.

Running on anabolic energy

I started executive coaching with a former colleague a few weeks ago. One of the first exercises we went through was something called an energy audit. During the debrief, we discussed something called anabolic energy. Basically, this is the energy you draw upon in a fight or flight situation.

It’s a great energy to use in certain moments, but it’s also something that cannot be sustained in the long-term. You can’t keep drawing on anabolic energy indefinitely or you will drain the tank.

Today, I put my coaching sessions to work perhaps for the first time.

I didn’t have a great night of sleep last night and went into 5+ hours of calls to start my day. By the time my last call ended at 2pm, I was zapped and my first instinct was to grab a coffee and power through. In other words, I was going to try to activate my anabolic energy to get through the rest of my work day.

Instead, I came to the realization that I was basically running on fumes. Instead of trying to power through, I ended up just laying down on my office couch and took a 15 minute power nap. I woke up feeling energized and as I sit here right now, I’m feeling optimistic and ready to crush some work.

I wonder how many of my problems today can be fixed simply by just taking a nap.

Party weekend

Hope everyone had a good Memorial Day weekend. I had a bit of a party weekend mixed in with a lot of resting. We went out on Friday night with an old friend from college. While we ended up leaving at around 11pm, the next day was not fun as we were all nursing huge hangovers. Sophia and I ended up pretty much staying home all day only stepping out for a couple hours for dinner.

On Sunday, we celebrated our good friend’s birthday at Dolores Park. A day time event turned into night. It was a good ole fashioned all day party. Surprisingly, I wasn’t in that bad of shape on Monday, but I spent most of the day just recovering anyways.

Sophia and I are in a bit of a party phase right now. We’ve been going out a lot more trying to milk the last of this stage of our lives. We’ve both been of the mindset that we should try to go out as much as possible before the whole starting a family thing. On the flip side, nursing hangovers at age 33 is not the most fun nor productive thing.

I’m going to try to enjoy things for now. We’ll snap out of it soon enough.

The hard thing about hard times

I’ve fielded a lot of calls from startup employees and executives this week. The common theme this week and the previous year is a lot of regret. People wish they sold shares into strength during the height of the bull market. People wished they planned better. People wished they diversified more. You get the idea.

There’s a lot of shoulda woulda coulda. You can’t control what happens in the past, but you can control the future. Unfortunately, what I’m seeing is that a lot of people are compounding their mistakes right now.

Someone who was not properly diversified got whacked by the tech markets crashing so they sell everything to get out. Now that individual is sitting on a whole bunch of cash and will miss the run back up.

Someone who didn’t sell in the bull run will hold onto to shares hoping for 2021 pricing to come back and may be left waiting a long time, or perhaps forever.

Of course, not everyone’s situation is the same. You can get lucky in this world. It may be a smart move to do one of the two examples I mentioned above. But for most, holding onto the past is going to come back to haunt them once again.

That’s the hard thing about hard times. As in when times are good, you can still act irrationally when times are bad. Many made a bad bet in 2021, and then will look to double down on that bet. On the flip side, many will learn from their mistakes and correct course. History has shown us that more times than not, the latter will end up in a better position.

The early stage remote vs in-person debate

I had lunch with a founder who just launched his company about a year ago today. It was great to meet in person and just interact. I’ve been starving for more in-person interactions lately. I’ve made a much bigger effort in the last month to meet people in-person and I’m loving it. Something with the pandemic has made me almost dread doing in-person meetings at times, but after I’m done, I’ve always been glad that I made the initiative.

On the topic of in-person, one thing he said to me that was interesting as that he regrets that he hired remotely right now. It has come with a lot of challenges getting the initial company off the ground.

I can completely understand why. When Secfi first started, we were spread out between Amsterdam and San Francisco. But we had our founders and others fly to San Francisco quite often. I’m not sure if we would have been successful if we hadn’t been in-person in the early days. There was just too much going on and too many changes happening too quickly.

Things are a lot different now and we’re able to functional well remote, but we’ve got much more defined processes in place.

The Tiger problem

The secondary market news of the last week is that Tiger Global is looking to run a strip sale a large chunk of their startup portfolio. Their LPs seem to not be happy with the future prospects of the fund and are likely demanding the fund to return as much capital as possible.

The prospect of hundreds of millions (if not Billions) of dollars of startup equity up for sale in a depressed market is not generally a positive thing for the ecosystem. Most of the shares will undoubtedly be sold at severe discounts.

The effects of this have been felt immediately. I spoke to a few partners and unfortunately buyers have been pulling out their bids once the news broke.

I don’t know how this will all end. It’s hard for me to see a lot of buyers for a lot of Tiger’s positions in the short-term, even at a big discount.

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.