The quiet

I slept like shit last night waking up often and thinking about some work things that I knew were not that important and were going to be fine. Of course everything worked out perfectly fine today and I knew that it would be. But anxiety is anxiety and it seems to get me good in the worst possible times. I could really use those extra couple hours of sleep.

Things are oddly quiet right now. It’s May so I suppose it’s the start of vacation time and it does seem like a good number of people are out of the office.

I would’ve thought that there would be at least a few more S1s filed by now. We’ve had Rubrik, Reddit, and Ibotta go public this year and all have been deemed successful. If you told me a few weeks ago that would happen, I would’ve guessed at least a few more companies would at least file.

We have been hearing that a lot of people are pushing plans out to 2025 altogether. Perhaps with the uncertainty of the election year, the geopolitical events happening domestically and abroad, and inflation, it may be enough good reason to sit tight and wait until 2025. Perhaps investors are looking to “sell in May and go away” already.

Overwork

I had a great weekend up in Napa celebrating our close friends Sam and Leili getting married. We had a ton of fun in the sun on Friday doing a bit of wine tasting and relaxing. The wedding on Saturday was absolutely gorgeous and I had a great time.

Sophia made sure we got some naps in on both Friday and Saturday, and that was sorely needed. As someone who doesn’t nap often, falling asleep for 1.5+ hours on both days was a sign as any that I’ve been putting my body through a lot and I need more rest.

I was reading about the sad news about the Bank of America junior investment banker who passed away from exhaustion after working multiple 120+ hour weeks. While he was a junior banker, he was also a former Green Beret or special forces operator in the army. This is someone who has gone through grueling training in their lifetime, not someone who is fresh out of college.

I know investment banking is a grueling and brutal job that most know what they’re getting into, but losing your life over work is just not it. We all go through busy weeks of work, but working that many hours in a week back to back is just not sustainable. I’ve never worked in banking, but I have gone through weeks of 80+ hour weeks and your brain and body can only go through so much.

I can only imagine what that individual’s family is going through and I hope this brings some changes to the industry. No one should ever be put in a position that their lives are ruined because of work, yet alone losing their lives because of it.

For myself, I’m lucky to be working at a company where we acknowledge the realities and challenges of startup life, but also put a premium on work-life balance. It’s a reminder for myself to always look out for folks on the team who may be overworked and provide my support.

Giving up control

I’m off to Napa today for a wedding. Working hard to clear my inbox and get some things done in the next 45 minutes and taking a few calls this morning in the car.

I’d like to get my work to a point where I can actually take some days off without ever checking my inbox or doing things. I know it’s a bit of a pipe dream while at a startup, but I know it’s possible.

It’s something I’ll need to work towards. I have an awesome team and it’ll be on me to train them properly so they can step in for me on most matters when I’m out of office. It’s a great opportunity for the people on my team to step up and it’s great for me to be able to recharge properly. I need to work towards that.

Recruiting and hiring

I’m off tomorrow for my good friend’s wedding in Napa. I’m really excited to get away, even for just a few days. Hanging out with friends in the sun and celebrating is always a great way to unwind a bit.

Recruiting and hiring is top of mind for me right now at work. Since we met as a management team at an offsite a couple months ago, it was evident that we needed to make some key hires this spring and summer to strengthen our team.

We’re in the heat of that right now and as always, it’s taken up more time that we initially expected. That’s okay and it’s time well spent.

Recruiting great hires takes time. You don’t meet someone and convince them to join the company with just one quick conversation. It takes time to nurture individuals and get them excited about your mission.

On the interviews, we go through many candidates resumes and that takes hours every week for each position. Then we have to go speak to the candidates that we feel fit within what we’re looking for. As frustrating as it is when we speak to a candidate that doesn’t fit especially after spending hours, it’s the right decision to wait until we find the right fit.

We are constantly reminding ourselves that we need to raise the bar and not to settle. There are amazing candidates out there, but we want only the best fits for Secfi. The time and effort spent is worth it.

IPO interest

After an exhausting couple of days, I finally feel like I’m back in control and things are not spiraling anymore. It took a few extra hours of work on Tuesday and a good night sleep, but I’m starting to feel normal again. Regardless, I’m due for at least a few days off to just relax though and I’m going to look to do that next week.

On the IPO market, it seems to be that Reddit, Rubrik, and Ibotta stock are all holding up despite the market dropping. All 3 have successful IPOs and were able to debut with an IPO pop. That’s a good sign as investors show interest in IPO names once again.

We’ll have to see where the stock trades in the coming months as we get to the IPO lockup expiration. But for now, so far so good. All 3 shares are down below the initial opening price, but they have held up for the most part and I’d imagine employees will be generally happy to finally getting a piece of liquidity.

The shitty part about startups

I wish I could go out and tell everyone how awesome my work life is always. But unfortunately that’s just not always true. Anyone that’s worked a demanding job will tell you that there is no perfect job.

This is especially true at a startup where you are forced to take on many roles and wear different hats. Now I know that in general, that is a positive thing. You want to have an impact on the business and have important responsibilities. It’s why we join a startup to begin with but it’s always a double edged sword.

Put simply, you’re forced to take care of everything that falls under your umbrella. At bigger companies, you may have help from staff or other departments such as legal, HR, etc. However, at a small startup, you’re often a team of one and don’t have the luxury of having specified help.

Right now I’m dealing with separate regulatory, HR, legal, and accounting matters on top of dealing with my “day job” of closing deals. Not exactly my definition of fun.

To keep myself going, I keep telling myself that nothing easy is every worth doing. That makes me feel slightly better about the mountain of work I have in front of me.

Feeling the burn

The unfortunate but familiar feeling of burn out is starting to come back. I’ve been battling bouts of burnout for the last few years and for better or worse have gotten familiar with the signs.

For me, it’s an obvious sign when it’s difficult to get out of bed and get going on a work day. It’s beyond just feeling tired though. We are all tired, but I can usually power through tiredness especially if I’m excited about work. But when I’m starting to feel burnout, the excitement is muted or just not there.

Whenever I get the feeling, I try to reflect back and figure out the root cause. This time around, I believe it’s simply just not taking enough time to rest and recover. I’ve taken a day or two off for long weekends the last couple of months, but that is usually due to travel for a weekend event.

I took a few days off to go to Hawaii in February and that was nice, but it’s been over 2 months and perhaps it wasn’t enough. Last year I took a week staycation to just recover and recharge. I think a few days to a week off to recharge is exactly what I need right now and I’m going to try to find sometime in the next couple of weeks to do just that.

Prioritizing

Work has been incredibly busy the last few weeks. With the IPO market back, we’re seeing a lot of activity and renewed interest from employees looking to exercise their options or obtain liquidity. It’s great for business after a couple down years.

We get to see a lot of great companies which is awesome. Learning about different businesses and their drivers is one of my favorite aspects of the job. The downside to having a great pipeline is that we can’t fund everyone’s deal and we need to prioritize the ones that fit our structure the best.

One of the hardest parts is having to tell someone or a company that we couldn’t get there. All these years and it’s still a difficult part of the job for me. There’s some great companies out there that are definitely difficult decisions to say no to. But at the end of the day, it’s our job to make sure our capital is allocated in the best deals possible and that means picking the best of the best, not just great.

Being a good person

I’m fortunate to have some friends and acquaintances in life where I would confidently say that is an amazingly great person. They are the kindest and caring people and anyone would be fortunate to have them in their lives.

For myself, I know I that my friends are not saying that about me. I know I’m not in the top tier of kindness or caring relative to these friends. I’d like to consider myself a good person, but that’s a judgement for other people to make, not me.

All that said, I do try to live my life as a net positive to society. I like to think that one of the reasons I’m on this planet is to help others. Working in financial services, I always try to operate in a position of helping others. One of my top principles in life which has translated to my work life at Secfi is to always make sure we’re doing the right thing for people, even if that jeopardizes business.

Unfortunately, we do run into a lot of bad actors from time to time. I’ve had a lot of stressful situations in the past where you stick your neck out for someone to help them and they take advantage of you. This happened a couple times these past couple of months. I try not to lose any sleep over these situations, but they do eat at you a little bit.

These situations will continue to come up so I try to remind myself that the vast majority of people that we work with are awesome people. A few bad apples shouldn’t ruin the batch. Above all, I shouldn’t change who I am because of these select few people.

Tik-Tok

I just read that Biden signed a bill that forces ByteDance to sell Tik-Tok in 270 days or face a ban. ByteDance now has until January 19, 2025 to sell Tik-Tok.

I personally support the ban on Tik-Tok. It’s naive to think that China has no influence on Tik-Tok. They have influence in every major company in China. It’s simply too good of a tool to influence Americans and I don’t see a world in which China is not using that to their advantage.

These next 8 months will be very interesting. We’ll have a lot to discuss including First Amendment, China vs US, censorship, Gen Z, etc. It will be one of the most heated discussions in 2024.

My prediction right now is that we’ll have some cop-out middle of road agreement. Perhaps Tik-Tok spins out a US entity where ByteDance may still have control over the broader Tik-Tok and have an investment in the Tik-Tok US. But this may satisfy lawmakers at least. Or there will be agreement to put things in pause prior to the election to gain votes.

The new operating reality

I just read that Google search boss Prabhakar Raghavan told employees at an all-hands meeting that “things are not like they were 15-20 years ago.” He was speaking specifically about the increasing competition and regulatory risk that Google is planning on facing in the coming years.

I would have loved to get a full vide of the presentation. Google has been in a position of power for the last 20 years dominating the search and a lot of the tech world. Employees enjoyed cushy pay and appreciation stock coupled with amazing workplace perks. I like many have been envious of some of the things I’ve heard.

None of this is a surprise to me of course. The tech world has rapidly changed over the last two years post-ZIRP. In addition, we have tech advancements like AI which creates a new dynamic. While Prabhakar was referring to Google, I do believe that this is likely the new operating reality in almost all of tech in general.

Employers focused on employee happiness and flexibility over the last 10 years. The next 10 will be about employee productivity. Things got too cushy for most of us in the tech world, especially in the ZIRP years and we all needed a dose of reality.

Living life

I’m riding a bit of a natural high this morning. That’s a bit rare on a weekday yet alone a Monday morning. But the combination of a nice long weekend along with very pleasant weather has me in good feels.

I took off Thursday late afternoon for Lake Tahoe and took off Friday to get a couple days of spring snowboarding in. It was nice to be up in nature and get on the mountain. I unfortunately got only 3 days total this past season as my life starts to get busier and I need more time to recharge over the weekends.

Being up in nature and outdoors always puts me in a good mood. I don’t take Lake Tahoe for granted, but every time I drive up there, I just admire how gorgeous it is and how beautiful life is. It’s cliche, but getting out of the city and away from my computer from time to time is exactly what I need.

On Sunday, we had a gorgeous day in San Francisco and Sophia and I took full advantage to hang out in a park nearly all day. We ended with a great dinner and a good night of sleep. It was the perfect weekend and what I needed.

It’s a great reminder that although I work an often stressful job, there is a lot of life to enjoy. I’m back in the office now and ready to grind again.

Staying present

I’m headed to Tahoe today to get a couple days of snowboarding in before the season ends. It was a bit of a spontaneous trip, but given that I’d only been up once this year, I’m excited for it. I’m not sure how much time I’ll have next winter to go the Tahoe.

It’s a sad realization that these spontaneous trips to Tahoe with friends may be coming to an end, but that’s life and part of growing up. There’s only so much time in life so I’m trying to enjoy every moment of the present that I have.

It’s easy to start thinking about tomorrow, or next month, or the next year often. Afterall, we do a lot of planning in our work and personal lives. But one thing that has helped me enjoy life more is staying in the present as much as I can.

I grew up as a worrier and a planner to combat that worry. The planning is still there, but the worry has mostly disappeared. I credit a lot of that to my meditation practice and my maturity. I stay in the present much more and try to enjoy the people around me in this moment that won’t happen again. Still a long ways to go, but it’s trending the right way.

Open day

I’m excited for today as I wrapped up all my calls by 8:30am. For some reason no one decided to schedule time with me today despite my Tuesday and Thursday being packed. I wonder if the 75 degree day in San Francisco has something to do with it or if it’s purely coincidence.

I don’t get these days very often so I fully plan on taking advantage. I have a long checklist of things to do and I plan to knocking them out one by one. It’s nice being able to actually get stuff done during normal business hours as I’m usually on calls all day and then have to log on after dinner to knock out the remaining items.

Perhaps more importantly, these days are great for brainstorming. Some of my best ideas come when I’ve got a clear calendar and I have time to just sit down and grind with my thoughts. It gives me time to plan and think about the future more rather than be reactive to what’s currently happening.

Searching for business opportunities

I’ve been looking around a bit for some small businesses on the side to potentially invest in for additional sources of income. It’s more opportunistic than out of a position of need. I’ve always had that entrepreneurial spirit which is why I’m at a startup.

The startup itch is real and I’ve loved my time building Secfi into what it is. However, I know there’s a lot of ways to make money outside the tech and finance world. And one of our goals this year was to explore that in more detail to see if there’s anything I want to pursue.

Part of this is making sure I keep an open and creative mind at all times. As pretty much everyone, we always fall into a doom scrolling trap from time to time whether it’s on social media or on a website like Reddit.

I find these platforms amazing for generating ideas. People love to post complaints on the internet about problems they are facing in the real world. Most see this as a source of entertainment and most of it is, but at the same time it’s always a great source of inspiration for business ideas.

The /r/SanFrancisco subreddit has been particularly a great source for me. People often use the subreddit as a place to complain about people or the happenings in the city. And I’ve been able to generate some decent business ideas from this. I’m not sure if any of the ones I have right now are going to materialize yet, but I try to keep an open mind to exploring things.

Random Monday musings

I had a busy start to my weekend but ended it with a whole lot of sitting on the couch watching the Masters on Saturday and Sunday. My Friday was a bit longer than anticipated with some golf that went into dinner to a housewarming party. Luckily I had the Masters as an excuse to sit on my couch and recover the rest of the weekend and I’m feeling rested today on Monday.

On the Masters… Scottie Sheffler is just dominant. It’s not often that the favorite in a golf tournament actually wins it. It’s not like other sports as statistically the favorite likely won’t win. But yet again, Scottie just continues to go on a run. He seems like a big family man and with his first kid on the way, I wonder how much this run will continue. Everyone thinks these golf runs will continue for longer than they do, but they usually end earlier than expected.

On golf… I played a par 3 course on Friday. I know, it’s just a par 3 course but I shot 4 over and hit 8 out of 9 greens. My putting leaves a lot to be desired, but my ball striking is very much improved. It feels like things are finally starting to click for me on the golf course.

Things are not fun geopolitically right now. With Iran attacking Israel, we have yet another large war scare on our hands. Hopefully people will come to their senses and we find a war to peace sooner than later. My heart hurts for all the innocent people involved in these conflicts.

The tech scene

Being a local here, I’ve always been a bit conflicted on the tech scene. Of course, I am in the industry and I do believe that tech makes the world a better place. On the flip side, there’s a lot of stereotypes that are unfortunately just true and some people whose entire identities are based on their work and tech. As much as it’s creeped up, I try not to spend too much time with people who can only talk about their work.

Last night, I had one of those really cool SF moments. My friend organized a dinner for a celebration. Sophia and I attended along with a lot much more accomplished VCs and techies. Everyone was absolutely awesome and it was amazing being able to talk to some of the pioneers in the industry.

From people who helped pave the path to self-driving cars to VCs who have been in the game before I even started work, there were some heavy hitters here. I was most impressed by the fact that most of these people were just normal people who have families and have other interests in life outside of work.

There was no pretentiousness or bragging. I suppose the people who perpetuate the stereotypes are probably the loudest and only a small group of the tech bros here in SF. I was fortunate to be able to spend a few hours with them.

Raising the bar

We’re back in full interview mode at Secfi and looking to hire for multiple roles. It’s a fun and exciting time, but it comes with it’s stresses.

It’s always exciting meeting hungry candidates who want to work at Secfi and help take the company to the next level. There’s a ton of entrepreneurial minded candidates out there that are excited to join a small startup like Secfi and I learn from them every time I have an interview.

At the same time, hiring is easily the hardest part about running a startup. A bad decision can be costly on not just the balance sheet, but everyone’s time as well. Like everyone, I’ve made bad hires in the past and it was not been fun dealing with the result.

There’s a fairly simple mantra when it comes to hiring at startups and that’s to hire someone that “raises the bar”. You want to look for people that raise the average bar of the company in terms of drive and skillset. That doesn’t mean necessarily that person needs to have more experience in areas. Someone with little experience but intense drive and commitment can raise the bar.

It’s no surprise that the bad hires we’ve made were people that we weren’t convinced raised the bar of the company. Whereas the good hires all brought something unique or were so driven that they raised the bar.

Death dreams

I’ve been thinking about death a lot recently. It’s been a weird but kind of therapeutic journey. I’d imagine a lot of this was driven by my father in-law having a stroke and a potentially near death experience last fall. That experience combined with the fact that I’m now 34 and “not young” anymore has me thinking more and more about life and death in general.

I don’t think it’s something I worry about - I hope to live a long life, but thinking about death has also made me reprioritize my life a bit which has been a net positive.

I listened to a podcast by the The Daily’s Sunday read about death bed dreams and I found it fascinating. In short, people who are nearing the end of their lives often have very happy dreams about their lives and potential after lives. This all starts weeks but goes all the way up to the day of death.

People who studied these dreams report them as very therapeutic. The dreams are often about loved ones, pets, or happy moments in their lives. The dreams can often create a sense of fulfillment about one’s life. It sounded as if one’s brain and soul was recapping the happiest moments of life.

On top of that, people reported having a lot of dreams about seeing loved ones in the future. People who are close to dying were no longer afraid to die because of these dreams. Despite growing up Catholic, I haven’t been a very religious person and I’m not sure I believe in an after life. But this gave me a lot of to think about.

I couldn’t help but think if these dreams were similar to psychedelic induced trips that have been the rage recently.

Having enough

I stumbled upon a very clickbait-y Twitter thread this morning. Some passive entrepreneur grifter was selling his book, but had a viral thread where he posted videos of this one guy (not himself) going around and asking 70-100 year old folks what matters in life. It was one of the few times I’m glad I watched a grifter’s thread.

I had been feeling a bit uneasy about money recently. I haven’t been struggling by any means as Sophia and I have everything we need and live a good life. But after two bad market years combined with the potential that we’re starting a family soon had me perhaps nervous about money for the first time since right out of college.

Of course, this was all in my head. Sophia and I make more than enough to live comfortably. We’re not rich by any means (and probably not close in the spectrum in SF), but we both work good jobs and bring in enough that we have everything we need and then some.

This thread of videos really brought me some positive thoughts and energy back to my brain when it comes to money. Nearly every one of the people interviewed mentioned that in their older age, the thing that felt like it mattered more in the early years was money. At their age, they’ve realized that there’s a lot of things money can’t buy such as love, relationships, and time. You can’t buy more time with someone.

While money will be important in the aspect of being able to provide for my family, the most important thing in life is love and relationships. At the end of the day, this thread was an amazing reminder that enough is all we really need.