Technological overabundance

I take off for my two week trip to Japan on Thursday. I had previously been to Japan 7 years ago, but only to Tokyo and Sapporo. This time around, we’re headed to Tokyo, Osaka, Kyoto and Hakone. Now in my 30s and traveling with my wife, it’s going to be a much different trip than when I was 26 and single.

Sophia and I were already discussing which movies and shows we wanted to download and watch on the flight. I also started googling how good the WiFi is on this United flight to Japan just to test whether I would be able to stream my video game. And of course, this is already on top of the in-flight entertainment system.

When I was a kid, I used to love airplanes. I loved being on a long flight. I would take long flights to Indonesia either with family members or solo often. 14 hour flight to Hong Kong? No problem. I had the tiny television screen and Super Mario on the in-flight entertainment system. That one game along was enough to keep me entertained for nearly the entirety of the flight.

I sometimes wonder to myself whether we live in a period of overabundance. One in which we have nearly everything we want or need at our fingertips, but at the same time, we’re never satisfied. There’s no doubt that technology has contributed positively to our lives. We live longer. We can connect more easily with friends and family. The world is more open and global generally.

Nowadays, I’ve got a running Excel list of restaurant recommendations from Tik-Tok, Instagram, and Reddit posts alone of 70+ places. Back in the day, you had to read books or talk to friends to find out the best places to eat. There was a whole lot more serendipity about finding some great places to eat.

Maybe a world where you’re stuck with only Super Mario 2 and 3 movies for a 14 hour flight is one in which we’d prefer to not go back to. Of course, more options and entertainment the better. But I guess there is something great about the simplicity of things back in the day.

Another golf trip in the books

I spent the early weekend in Tahoe golfing with the guys. I love Tahoe at all times, but there’s something different about the summer time. I am just always happy whenever I’m up there. We got a tee time at the famous Edgewood golf course on Friday and drove out to Carson City to play at Toiyabe on Saturday.

My golf game is getting a lot better, but I still make a lot of critical mistakes that prevent me from scoring well. For the first time in awhile, I’m back to swinging the club with confidence. But consistency is a major issue for me and I find myself putting up big numbers on the score card far too often.

On both our Friday and Saturday rounds, I headed on 18 down on my head-to-head and pretty much even on the team cumulative score. I ended up going full clutch and won both days on the last hole of the day. My Saturday round included maybe one of my best shots ever as I had a very difficult chip off the side of a hill to get up and down.

I may not be good at golf, but I feel like I play my best when it matters the most.

Are we back?

Activity in the VC world has started to pick up again. I myself personally lost out on an angel deal as I wanted to slept it on last night and came back this morning to see that they hit their cap.

I had an email forwarded seeing that an AI company raised over $100M in their seed as well although that may be isolated to the AI world.

We’ll see where this goes. It could very well be a false bull run. But I know a lot of VCs are sitting on a lot of capital right now and it will need to get deployed at some point.

Early stage deal flow

I’ve been seeing some great deals in the early stage lately. Nearly every company I’ve come across is raising on a SAFE still and postponing their Series A and Series B until the markets settle a bit. With that said, the valuation caps are much more aligned to investors like me who write smaller checks.

I’ve largely kept my wallet closed over the last 6 months except for a couple opportunities. I wanted to see where valuations would settle and how the latest trends in AI would shake out.

I still don’t have an amazing grasp on the AI trend, but I suspect that it’s overhyped and the biggest benefactors will be the incumbents. For that reason, I’m holding off on any major AI investments right now. Part of that is that I just don’t have access to the great AI investments out there.

Beyond AI, there seems to be some amazing founders building some interesting products. I’m pretty excited to start writing checks again in this bear market. There will be some great companies built during this time that have much better fundamentals and plans than what we saw in 2020-2021.

For me, I need to make sure to temper my excitement. There’s going to be a lot of good companies to invest in, but I’m in search of the great ones. I never want to be in a position where I can’t write a check to one of these can’t miss opportunities because I overextended too early.

SoftBank and WeWork

This week, I’ll be moving down the hallway in my WeWork from a 7 person office down to a 3 person office. It just didn’t make sense to keep paying for a large office that has at best 3 of us in at a given time during the week. I have to give it up to WeWork though - the product has been pretty damn good. The flexibility for us to move around is great. The weekly happy hours have allowed me to get some social interaction.

It seems like WeWork, as a company, is in a bit of trouble as their CEO has stepped down amidst a lot of pressure from SoftBank. I don’t know what the future of WeWork will be. I hope they are able to stay alive and make it through. While far from perfect, I’ve enjoyed being a WeWork member over the last 6 months.

On the topic of SoftBank, they themselves seem to be having major issues with reported layoffs coming for a 1/3rd of the company with a focus on the Vison Fund staff. At this point in time, I’m ready to hang it up on the capital as moat strategy that SoftBank pioneered and others like Tiger followed.

It’s largely been a net negative on the startup ecosystem. We have a ton of otherwise great companies that raised at insanely valuations that may now be dead in the water. I met with some CFO who equated what these crossovers funds were doing as a ponzi scheme and it’s hard to argue with that point. They invested and hoped to get out before it came all crashing down.

Technology and kids

I’m a bit afraid of raising kids in this era because of social media. Maybe it’s because I’m just in that last generation where social media wasn’t part of our childhood. But I see kids today like my younger sister who is 12 that’s just glued to YouTube or Tik-tok all day and it worries me.

When I was a kid, I was definitely glued to a computer screen and it worried my Dad quite a bit. I loved surfing the internet and playing computer games. I guess this is part of me just getting a bit old and out of touch with the kids of these days. But I feel like social media is a completely different animal than playing Starcraft with your friends.

There’s a lot of scary studies on the negative effects of social media on our kids these days. It seems that people are generally unhappier and are suffering from lower than ever self-esteem. Of course, this all could just be overblown by the media narratives and I need to chill out a bit.

All that said, I’d be lying if I wasn’t worried that my kid(s) won’t want to play catch with me or attend a ball game together. It seems that we’re closer that the norm will be attending a football game via a VR headset than stadiums becoming completely full again.

For now, I’m just operating under the principle that change is inevitable. Our kids will have much different childhoods than Sophia or mine. Despite all the potentially scary stuff, the optimistic in me does believe that our kid(s) will have a better childhood than mine.

Routines and feeling good

This week was the best I’ve felt in a long time. I had a lot of energy and felt optimistic the entire week. I don’t really know for sure why this was the case. My routine didn’t change much, but I felt a lot better waking up this week.

I didn’t sleep a whole lot, but my sleep quality was high. I slept consistently and woke up at 6:30am everyday. I ate decently healthy, but wasn’t a saint. I worked out hard and 4 times this week. None of that has been much different than before.

The one thing I can maybe point to was having a great last weekend. I didn’t really drink much and therefore my sleep was better than normal. On top of that, I woke up more consistently to my weekday sleep schedule. Lastly, I had a long and full weekend of activities I enjoy.

At this point, it’s very likely a sign that I need to use my weekends more to recharge more. Staying out later and upending my sleep schedule is likely a big culprit of how I feel during the week.

My management philosophy

My management philosophy is fairly simple. I hire smart people and empower them to make the right decisions.

The way I view managing people is the opposite of micro-managing. I believe micro-managing is possibly the worst way you can treat your employees as well as the worst thing you can do for your time. I view micromanaging someone as an insult to their intelligence and their abilities.

I’ve heard some people say that I am a hands-off manager. There’s probably a bit of truth to that, but I’d like to say that I lead with trust. I empower my team to make decisions and move the ball forward. If there’s something that I need to decide on, I’ll let them know.

The power to make a decision doesn’t mean that they will always make the right decision all the time, but if I hired right for the role and provide the proper framework, they should make the right decision more often than not. Mistakes are a crucial learning tool.

Of course, where things always go wrong is when you hire the wrong type of people for your management style. I’ve made that mistake before. Some people do not handle the freedom well and prefer a manager that’s a bit more hands-on and puts more guardrails up. That’s okay, but they’re just not a fit for my team. There’s plenty of other companies and teams that have that.

Lastly, once you have the hire, it’s also my job to make sure that there is a proper framework for working. The captain still needs to steer the ship in the right direction. The framework needs to be non-restrictive and still allow the team member creative freedom. Employees need to be given the chance to thrive and prove themselves through their work.

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.