Sand Hill

I took the last couple days off from writing as I was at an event in Palo Alto called the Innovation Field Trip. It was hosted by a fellow startup and Secfi partner, Allocate. The event was largely a way for people not in the startup/tech ecosystem to meet VCs and learn about what’s getting built here.

Despite living in the area and being part of the ecosystem, I was incredibly impressed by how well the event was run. We met a lot of top tier venture capitalists both who are running solo shops as well as those working for some of the biggest names. Huge shout out to the Allocate team for putting it on.

I seldom make it down to the Menlo/Palo Alto area. Growing up and living in San Francisco, I never really saw the allure of visiting the “legendary” Sand Hill road much. My trips down there are for football games when UW plays Stanford.

This time around felt a bit different for what I believe to be a couple of reasons.

I believe my change of perception comes from the fact that I’ve been working a startup the last 5 years and have come to appreciate the companies being built. Startups are incredibly hard and there is a level of appreciation I now have for those that endured the long journey of building a successful company.

Secondly, I’ve come to terms that all VCs are not built the same. I’ve had somewhere between an irritation and disdain for a lot of VCs out there - both ones that I have met and ones that I haven’t. Some have treated me like shit. Some are just annoying as shit on Twitter. I also blame some for helping cause of the issues we’re facing right now.

After meeting over 10 different managers between the 2 days, I’ve realized that most of these top tier VCs also share that same disdain for a lot of these same VCs. They acknowledge that the industry has gotten out of control and will need to be reeled back. Some had harsh words for those “VC tourists” and even called out quite a few.

I do have a new appreciation for the industry after the trip. Most of these funds are built more like startups than they are actual just investment funds. It was really awesome meeting and learning about each firm and how they differentiate.

Once I get my head above water and get a chance to put my notes together, I’ll write more about some of the key takeaways. For now, back to work getting to inbox zero.

Getting away from the madness

It was incredibly stressful leaving on Thursday as I was absolutely swamped given all the news and happenings of the week. I had even thought about canceling last minute so I could focus on work.

I’m glad I didn’t. It didn’t take me long on Thursday to realize just how much the last few weeks have taken out of me. I felt my anxiety and tension the entire flight and it didn’t really subside until my friends and I met up and started our night. There was an immediate sense of relief as my friends and I hung out at dinner and talked about anything but work.

With a lot of the happenings in our world, it was amazing to just get away from everything for a little bit. Sometimes you just need to escape the craziness of your current world and I’m in a much better headspace after a 3 day break.

No rest for the weary

I booked a trip to Vegas this weekend to golf and watch March Madness with some friends. I booked it a few weeks ago given things were a bit slower and I wanted to take advantage of the times.

Of course, we’ve had a hell of a week with the SVB and bank issue combined with some major announcements like Stripe’s round closing.

I couldn’t help but just laugh. This may be the worst weekend to go on a trip. For some reason, this seems to happen to me quite a bit for some reason. Everytime I go away, a big deal comes through the door or some news hits the wire.

I’ll be running on fumes this weekend, but I also need to pace myself and ensure I’m getting the proper rest. It’ll be a good trip regardless.

Ponzi scheme?

I had a great chat with the CFO of a unicorn today. I hadn’t spoken to him in about year and we were shooting the shit about all the events of the last 12 months or so. We shared a lot of the same cynical takes on the broader tech and VC industry. We couldn’t help but ponder just how much of this mess that we’re in right now is because of greed in the industry.

I was especially intrigued by what he said about VCs of the last 3 years effectively running a ponzi scheme. Many of these funds and investors were just bidding up the prices of their portfolio companies and hoping to get out before the crash. They had known that this was not sustainable but they participated anyways in hopes of building massive gains and dragged the entire industry along with it.

I had never heard someone equate VC to a ponzi scheme before. I thought it was an incredibly interesting take and angle on the situation and it was hard to argue as many of these investors had this idea in mind.

The unfortunate part to all this is that a lot of these companies will suffer greatly from all this. There’s many companies out there that are trading down over 80% of their peak valuations and not many can or will recover from a large crash whether they are private or public.

I do believe there are many great investors out there looking to build companies. I’m personally ready for the market to turnover so we can get back to building.

Rooting against tech

One thing I’ve come to fully realize amidst all this SVB fallout is just how much of the country has a negative view on tech, VC, and Silicon Valley in general. Sure, part of it is all political and you can expect that, especially in 2023. But you can’t really ignore the fact that it seems like the vast majority of the country is rooting against the broader industry. Some of it is warranted of course.

There’s a lot of load individuals in the industry that can give us a bad look. They are loud and vocal. We’ve received a lot of flak for living cushy lives funded by VCs in a near 0 interest rate environment for almost all of the 2010s. Many “businesses” never should have been funded in the first place. When they fail, it’s easier for people to laugh.

I can’t fault people for making tech, VC, and Silicon Valley the butt of a lot of jokes. We bring it upon ourselves. Hell there’s a hilarious HBO show called Silicon Valley that makes fun of us and is embarrassingly accurate. All that is fine and I have a thick skin. I’ve been in this industry for 5 years and I’ve seen a lot of this first hand. We could use a bit of a reset and we’re going through that now.

But at the same time, it is disheartening to see just how many people are rooting for us to fail. They ignore the innovation, jobs created, and life improvements that have been created in Silicon Valley. They don’t understand the repercussions of watching Silicon Valley Bank fail. When tech/SV wins, the country wins… yet we are rooting against our own.

All this does start with us. We need to do a better job getting rid of the bad apples… the grifters, the startup and VC tourists, etc. They unfortunately exist and a small number of people and companies are outweighing a lot of the positive momentum in tech right now. We can’t fully control what people think of us - there will be haters one way or another, but we can start by taking a deep hard look at ourselves and do better as an industry.

Grateful on another Monday

This was probably one of the weirdest weekends I’ve had in recent memory. The SVB explosion kicked off the weekend with a lot of fear and panic. That was not great for my anxiety levels. I had gone into the weekend thinking that something would be done by the Fed and luckily that was the outcome. I tried as hard as possible to keep calm all weekend, but admittedly it was difficult at times to get it out my head. I was nervously clutching my phone pretty much for the entire 48 hours.

What made it also weirder was that this was the weekend that I was celebrating my birthday so my brain was a bit conflicted. Sophia and I had dinner plans at Ken Sushi on Friday followed by a short celebration at Top Golf + dinner with friends. In a way, having all these distractions over the weekend helped keep my sanity by not focusing on the bad news. It was an incredible weekend and I do feel very fortunate.

At the same time, I do feel quite a bit of anxiety today given everything. Call it a case of the Mondays, anxiety from the bad news, and/or being tired from the day light savings time change. In light of not feeling my best, I figured I’d take the time to practice some gratitude and write down some things I’m grateful for today. It always does wonders in helping making me feel better.

So today, I am grateful for:

• An amazing wife that planned an incredibly birthday celebration for myself. Dinner was something that I’m going to be dreaming about for awhile and Saturday’s festivities was exactly what I wanted to do for my birthday. I’m incredibly lucky.

• Intelligent and talented coworkers who care about the company and our customers. Despite everything going on last week, our team stayed calm and acted quickly to get our employees and clients comfortable with what was happening.

• Living and working in the U.S. Our gov’t and country isn’t perfect by any means and I have my fair share of complaints, but we are lucky to live in a country that can and has protected individuals and consumers. We could be in a much worse position if the Fed hadn’t stepped in. Many unfortunately do not have that privilege.

Life comes at your fast

Just a little over 24 hours ago I was writing about how I was hoping the SVB situation would work out and that I was hoping it was an overblown overreaction.

Turns out that overreaction turned into more panic and the whole situation became a death spiral. It’s a sad day for tech and the entire startup ecosystem. SVB has been supporting startups, tech, and investors for almost 40 years. To see this happen is a sad realization of the day and age we’re living in.

Don’t get me wrong here though. SVB made a lot of critical mistakes starting with mismanaging their risk profile of their assets. They got greedy during 2021 like so many in this industry, and sought out higher yields for bigger profits.

Largely though, I can’t help but think that this situation could have all been avoided if everyone stayed calm. Instead, we had a lot of people inciting panic in the situation and caused a bank run that sent SVB spiraling.

This could have been avoided at multiple points including SVB properly managing their risk. I don’t know how this will all shake out. I’m hoping that it gets settled quickly and we had a bigger institution saving SVB and the depositors. The rippling effects otherwise are going to be ugly and beyond things we’ve seen since the GFC.

For now, I’m going to take my mind off everything and try to tune out as much as I can over the weekend. I can use a hug, a break, and many drinks.

SVB

I just got off 7 hours of calls so I’m severely behind on work and haven’t had much time to digest or dig into the SVB news much. I’ve only seen headlines at this point.

My initial thoughts are that there seems to be quite a bit of worry and overreaction to the earnings release. SVB is raising money as they are expecting continued higher interest rates in the future so hopefully this is just a precautionary measure to shore up their balance sheet.

I’ve heard the term “bank run” thrown out a lot today in Twitter. At this point, it seems like there isn’t a liquidity crisis the bank. For the good of everyone in the tech and VC ecosystem, we can only hope that this is all an overreaction.

Startup tourists

I’ve been seeing the term VC tourist thrown out a lot recently. I thought it was a pretty good way to describe the recent situation with lots of people looking to get in on the action when times are good in VC, but have been flocking for greener pastures during the down times.

I’ve started to borrow this term and start labeling some folks as startup tourists as well. I think in the late 2010s, we started to see quite of the workforce look to join startups. They were promised high salaries, work-life balance, and perks all funded by the incredible amount of venture capital money.

Many of these startup tourists never joined a startup to build something or believe in their company’s mission. They just wanted the perks and the clout that came along with the job. As we enter the 2nd year of this down market for startups, we’re going to see a lot of these tourists flock back to greener pastures, i.e. large companies.

Finding talent will be harder for us startup folks, but at the same time, it’s a palate cleanser for the industry. We’ll be left with the builders and those passionate about building great products and companies.

Changing expectatons

I had a good birthday yesterday. Except for a couple morning calls, I largely took the day off to just to treat myself which mainly involved eating. I wish the weather had cooperated a bit more and allowed me to spend most of the day outside, but that is life.

On another note - I have been preaching for the last year that startup employees need to be lowering their expectations in the post free money world. The days of early stage funding rounds with absurd valuations accompanied by a secondary are over.

There’s a lot of holdover from the last few years. I get inbounds all the time with unrealistic expectations on due diligence timelines, valuations, pricing, etc. There’s founders and operators out there that are still brainwashed from 2021 and hoping that will come back soon. I’m hoping that will finally be over soon.

As for myself, I too have to lower my expectations in this new day and age. I had a good chat today with a lot of teammates about that today. During our pow wow, I’ve realized that I also still have to adjust some of my expectations on things like metrics and timelines.

As much as I want things to move like they did back in 2021, I know that’s not coming back and everything has changed. Apparently, I too have a bit of 2021 stilled ingrained in me that I need to shake out.

33 and blessed

I turned 33 today. It’s a bit surreal as I’m officially venturing into my mid-thirties. In my late teens and early 20s, I was always a bit terrified of getting older. Growing responsibilities and adulting just didn’t seem that fun to me. Like most people do, I guess I just grew up a bit and I’m now enjoying the process of getting older and wiser.

I feel like every year of growing older feels like exponential knowledge and growth. You know more and mature, and then life somehow gets a bit easier because you do. Suddenly, a lot of life’s problems aren’t as big of a deal as they were when I was in my 20s. I love that feeling.

Of course, not all is rosy. I’m tired all the time. My body is constantly stiff or sore. I feel like I have future (minor) health issues starting to pick up. I miss the limitless energy of my 20s. I do occasionally miss the 4am nights out with friends. All that said, growing older is definitely much better than I thought it would be in my 20s.

While I occasionally joke about wishing I was in my 20s at times, I am incredibly blessed. I’m surrounded by amazing family and friends that care about me. I am in good health. I have a job that brings fulfillment into my life. I am happily married to someone who I want to start a family with.

I don’t take any of these things for granted. I know how lucky I am to have the life that I do. I’ll spend my day relaxing, eating good food, and practicing some gratitude. As my friend Erica’s dad used to say, “we are so lucky to be here today”.

Down rounds?

I had thought there would be a lot more down rounds announced by now. Perhaps there are a lot happening but companies are just simply not announcing them or keeping it hush in order to avoid the potential backlash.

Other companies may just be raising convertible notes instead in order of doing a priced round.

I still think there’s more down rounds coming in the months ahead. Startups need capital and many are still very much fundable albeit at lower valuations than they raised in 2020-2021.

I suppose the scary thought behind all this is that perhaps VCs are simply just not funding a lot of these companies that need capital. Some companies with high valuations, even unicorns, may not be able to raise and may be against the ropes.

I obviously hope there’s much less of that and more that companies are either preparing to announce these new rounds in Q2 or keeping things hush.

Brainstorming business ideas

The last few years I’ve been so heads down with Secfi that I haven’t had much of a chance to do my usual brainstorming for business ideas. That’s not to say I haven’t learned much about business - I’m fortunate to spend most of my day looking at or working with innovative companies.

I’ve had the chance to see how successful companies operate and what can kill startups. It’s a great first hand look into seeing how the best companies are built.

On the other hand, almost all my day is spent working with venture backed companies. Not every successful company needs to be venture backed. In fact, the majority are not and nearly all business ideas are better off without taking VC money.

The last few months I’ve been doing a lot of outside the VC world brainstorming in terms of business ideas. I’ve always loved learning about unsexy businesses like car dealerships, gas stations, soil, etc. A lot of these companies exist because they simply print money.

While I may spend the rest of my career at venture backed companies, that’s not to say that my learning should stay within this bubble. There’s a lot of great opportunities out there and I want to stay educated on all kinds of companies. There could be potential side business or a future endevour that I get interested in. It’s a big world out there and it would be a shame if I only stayed in my tech bubble.

Getting my mind right

Things are fairly quiet right now at work. There’s still news and stories out there in the VC and startup world, but the capital markets are slow right now. We obviously wish things were different, but that is the way things go when you’re in a business that’s tied to the markets.

As a type A person who has lived my first 32 years trying to find ways to be busy, it’s pretty hard for me to accept the fact that I’m not absolutely swamped all day. I get the thrill out of getting things done and/or beating the competition.

It’s funny to think about but when I’m absolutely swamped at work, all I want to do is do nothing or go on vacation. But when we’re in a slow period at work, we just want to feel busy.

I know things will get pretty hectic in the next few months as well so I’m doing my best to enjoy my time right now. It’s good to recharge the batteries and get my personal life.

There’s a lot of work projects that require my attention so I’m focusing on those tasks that normally wouldn’t get the time of the day. But I also know that I need to be my best self when things get hectic later this year.

That means taking this time to recharge rather than spinning my wheels on low value tasks. I’ve come to realize this from working at a startup in the last 5 years. There’s times to absolutely grind, but you can’t do it indefinitely. And grinding on low value projects or tasks just to stay in the grind doesn’t do you or your startup any good either.

So for now, I’m enjoying the relatively lighter work load while focusing on high value projects and getting my mind right for the upcoming year ahead.

Low morale and hard times

I had someone cold email me today asking to shares of his “startup” valued at $7m for $170k today. That may have been the steepest discount of any company I’ve seen so far in the private markets although to be fair I’ve never really heard of his company.

The cold email is symbolic of the times right now. Post pandemic we were promised the Roaring 20s. We got the roaring 20s for just a little over a year before the fun was all over. Lucky for us, we’re not in Great Depression times but things are far from good in startup and tech land.

I know quite a few people who are searching for jobs after going through layoffs. They’re in a brutal market right now. Those that are fortunate enough to be left are dealing with reduced workforces and slowing business. Couple a tough work environment with lowered valuations of their equity, and many employees are in a morale trough right now.

A large part of my day is spent speaking to other current and former startup employees and I’ve never seen morale this low across the board. A lot of individuals are just plain disgruntled and/or burnt out. They went from dealing with COVID to being busier than ever in the post-pandemic phase to everything coming crashing down again.

It’s been a hell of a 3 years since COVID started. Every year has been unique and challenging in different ways.

There’s not a magic fix for all this. Nearly every company is dealing with it right now and we’re no exception at Secfi. To remedy this, we’re going to go back to the COVID playbook a little bit. We’ll start small with more team events to enable camaraderie (and venting). We’ll of course encourage more vacation time, but also look to do company-wide days off as well.

Grateful

It’s an ugly day out here in San Francisco. It’s been cold and rainy for the last week, but today feels especially dark and depressing. I saw a bit of hail this morning and it looks like it’s 6pm out my office window right now. Couple the bad weather with the fact that it’s Monday, and it’s not an ideal scenario.

On Mondays like today, I try my best to stay positive. I’ve realized that in my past, it’s been easy to fall into a down Monday just by focusing on the negativity.

One of the tricks to staying in a positive mindset over the years is to write down things that I’m grateful for. I used to keep a journal and write 3 things I’m grateful for everyday, but I’ve since switched to blogging everyday instead. So I figured that today I get back to that to start my day off on a positive note.

Today I am grateful for:

1. A warm apartment where I was able to get some much needed rest

2. A great weekend to myself where I was able to recharge and get caught up in life

3. Cats. I was cat sitting for my friends who were out of town and I had a great time bonding with a very cute kitten.

Maybe I’ll get back to doing it every Monday.

Marathons not sprints

My wife tells me that I need to listen to my body a bit more. Like always, she’s right. I was absolutely just dead most of yesterday and almost fell asleep in the gym in the afternoon. I went to bed at 10:30 last night exhausted from the week.

I typically don’t set alarms unless I have morning calls and I pretty much wake up everyday by 7am at the latest regardless. Well this morning I woke up right at 9am in a bit of a daze. This never really happens to me and it threw me for a bit of a loop.

I was a bit surprised, but at the same time I’ve realized that I’ve run my body into the ground this week with a lack of sleep and overdoing it on the work.

I’ve unfortunately have a ton of work to do still, but I figured I need to take the weekend to rest and recover. There’s more days and this startup thing is a marathon, not a sprint. Or at least I can’t sprint the entire marathon.

High cost experiments

I’m beat this week. I’m normally at my desk at 8am for my morning slate of calls, but this week has started earlier and my routine has been completely thrown off. I’m excited to get to the weekend and get some rest.

This week, my team and I have been working on a few projects that we’re thinking about launching. I’m huge on trying new things and seeing if they work. We’ve had a lot of great success running these experiments in the past, although nearly all of them fail. One way or another, you learn something.

With that said, one question I always ask is what is the cost of this experiment. That cost may not necessarily mean just pure dollars. Time is probably the most expensive cost we have at a startup.

For a simple example, if we go and chase a theory that sending a calendly link directly to our calendars instead of having them set-up accounts will generate more leads. I can likely tell you with good certainty that theory will likely be true if we run the experiment. On the surface, most may think that “more leads are great, let’s do it!”

But then if you start breaking down the cost of running this experiment, then things start becoming much murkier. You will likely introduce many more unqualified leads. Let’s say you expect 100 new leads and your normal unqualified lead % is around 50%. With the new method, you may think this will go up to 80%. So you have 30 more unqualified leads.

At an estimated 30 minutes per unqualified lead call, then you have 900 minutes of employee time of cost to get 20 more qualified leads. That’s 15 hours of additional work to get those 20 qualified leads. Depending on the business or project, that may not be worth the time now that you’ve dug into the numbers.

On the verge of bankruptcy

One of the more surprising things I’ve learned about successful late stage startups is just how many of them were on the verge of dying at one or multiple points in their journey.

There’s the famous stories about Lyft being 6 weeks away from missing payroll and AirBnb’s founders selling cereal to try to keep the company alive, but I was a bit shocked to see that this was quite often the norm.

I’ve met and worked with a lot of successful companies in the last few years who were months, if not, weeks away from declaring bankruptcy. Some of the most successful $1b+ tech companies that we know of today were in that boat as recently as a few years ago.

It’s one of these things that’s incredibly stressful but inspiring at the same time. No one wants to be that position to be close to a dying business, but at the same time, it’s part of the gig of being a VC-backed startup. If you are in that position, then there’s not much you can do but put your head down and get to work. It can and often does work out.

Unfortunately, I imagine there’s a lot of startups out there that are in that position today. I’m hoping most of them are able to make it out of this down market and are able to continue building.

Learning Chinese

I’m excited for tonight as I have my first in-person Mandarin class. After I got back from my honeymoon in January, I had a desire to learn Mandarin after visiting Singapore. I figured it would be fun to start on Duolingo and see where things went after a few weeks.

Things started out slow and I was doing a lesson or two a day. But then I started to get addicted. Duolingo does an amazing job gamifying the language learning experience. Within a couple of weeks, I was pretty darn addicted. So much that I would take a break during dinner with friends to do a lesson to ensure that I kept my daily streak up.

While the gamification is part of why I like Duolingo, I also realized that I just miss the learning experience. I’m fortunate to be in a job where I do learn a lot on the job, but learning a new language is something completely different than learning job skills or knowledge.

I wanted to speed up my learning so I decided to enroll in an in-person Mandarin class that meets weekly. I can’t remember the last time I was so excited to go sit in a classroom with a teacher. The in-person learning experience is also something I’m really looking forward to. It’s been awhile since I’ve been in a setting like this meeting new people.

I’m not sure how long it’ll take me to get to a conversational stage of Mandarin, but I’m excited for the journey ahead to say the least.