Life is a good

Sophia and I had a mind-blown moment when we realized that it’s been still less than a year since we had to head to Croatia for a month due to my father in-laws stoke while on a cruise. We went to Croatia in October of last year and stayed for a month until right around Thanksgiving.

So many things have happened since that time, we felt that situation was years ago. Despite incredibly low odds, my father in-law made it through and we did our best to enjoy our time in Croatia. Since then, there have been a lot of stressful situations dealing with the recovery and everything that comes with that.

Life came at us fast during that moment. The realization that our parents are getting older and life is fragile. Sophia has been stressed with a lot of coast to coast trips this year. I’ve personally had to deal with a lot of growing pains as I get older myself.

It hasn’t all been bad though. Sophia and I are beyond excited to welcome our first child this year which will undoubtedly bring a lot of joy to both our families. We’ve had some great trips this summer.

As I sit here on a gloomy Monday, I’m feeling grateful for everything. It hasn’t been a perfect year by any means, but that’s life. My reset week this past week went well. I’m feeling great today and excited to get to the grind.

Overall, I live a great life. I have amazing family and friends. I have an amazing wife. I am grateful for everything I have and I’m excited to have a great week.

The new iPhone

I was reading a bit about the new iPhone 16 and deciding if now was the time to upgrade. It’s been 3 years with my iPhone 13 and besides slightly declining battery life, everything is still working fine. I don’t take many pictures or care much about the ever improving camera or those features.

I am interested in seeing how AI is built into this iPhone. There seem to be quite a number of features that could make things interesting, but I am yet to be convinced that the upgrade will be a game changer for me.

Everything seems to be around a better Siri and having a generative AI copilot built in. The copilot could be interesting and make things more fun, but with the ChatGPT app on my home screen, is it really that much better?

For now, I’ve decided to wait and see for the user reviews when they come out. Maybe there’s a ton of features that I’m missing at this point. Otherwise, I plan on waiting until next year to see what other AI features make it into the phone.

Starting a business

I was chatting with a close friend who just launched her own business recently. She’s really going through the challenges right now as the “excitement period” has subsided. When you first start out, you get to do a lot of fun things like naming the company and thinking of all the fun future ideas that you’re going to execute on.

Once that period ends, the real hard work begins like getting that first dollar in the door and dealing with all the challenges including regulatory and compliance. You get your first few bills and start to realize how much all this costs. Most times you don’t have a salary to rely on either.

The reality of starting a business is that you’re going to be heads down doing a lot of not fun things. Working with lawyers. Administrative tasks. Accounting tasks. The fun stuff like building the product is only a small part of the journey.

You also take a lot of L’s early on in the journey. You think you have something in the bag and then you get sucker punched. That happens over and over again.

The journey to becoming a successful entrepreneur is glorified often, but behind that success is a lot of mental strength. I have tons of friends who love talking about ideas and some of them are good ideas, but when push comes to shove, not many of them would be able to make it very far in the journey.

Small businesses

I’ve been casually eyeing a lot of small businesses in the past year or so. I’m still having fun at Secfi and I have no plans on leaving, but at the same time I think it’s natural human instinct to think… what’s next?

For me, that answer is likely going to be running a cash flowing business of some sort. The VC backed tech startup world has it’s perks, but the more I think about it, I do believe that my next gig will be running a smaller bootstrapped business of some sort.

I can control my destiny and hours much more. I can pay myself a salary that’s tied directly to the success of my company. Perhaps most importantly, it will allow me to work on something I’m passionate about at my own pace. I may even be able to start something on the side while I’m still at Secfi in the future.

There’s a ton of great businesses out there that make get profits. I’ve looked at everything from garbage disposal to nail salons to accounting firms. However, when it comes down to it, the most important thing for me is being passionate about something.

If I’m going to be grinding all these hours on a businesses, I want to be passionate about what we do. Of course, that’s easier said than done often. The most fun and sexy businesses don’t always make money. A restaurant sounds great in theory, but it’s a hard business to make money in especially for someone who has no experience there.

For now, I’m keeping my eye out and continuing to brainstorm. I’m in no urgent rush as I’m busy enough here at Secfi to keep me occupied for the foreseeable future.

Reset week

I wrote yesterday about how I plan on getting my body right this week by taking a week off to rest. I’m also adding getting my sleep right this week after yet another bad Monday of rest and sleep. This will be my reset week.

I’ve written a lot about my issues on rest and sleep over the years. I’ve struggled a lot these last couple years. I believe a lot of this is just getting older and my changing body doesn’t allow me to do what I used to do in my 20s, and I haven’t done a good job adjusting.

To be fair, I’ve made a lot of adjustments the past few years. But it feels like a bit of whack a mole. As I fix or attempt to fix one thing, I get older and that problem gets worse or another problem pops up. Isn’t getting older fun?

I know sleep issues are very common, especially in my friend group at this age. But at this point, I’ve got way too many bad habits to ignore and I’d be silly to continue to ignore them and slog through life feeling like crap.

So this will be my reset week. My intentions are to:

• Rest my body. I plan on doing a few active recovery activities like yoga, stretching, walking, etc. But this week is making sure my body can recover and heal.

• Get to a consistent bed and wake time. This has been one of the drivers for me not being able to feel rested.

  • I plan on being in bed by 10pm PST and lights off by 10:30pm PST. On weekends, I will allow this to push back 30 minutes with lights off by 11pm.

  • I will wake up everyday at 6:30am PST. Given the day and need, I may stretch this an extra 30-60 minutes but my goal is to be up by 7:30am PST everyday.

• Limit my social schedule on the weekends to ensure that my sleep is actually good sleep. I have been sleeping a lot in terms of hours on the weekends, but a lot of that isn’t great sleep as I throw alcohol into the mix. I can live a little bit, but limiting my intake or at least making sure I get one night of good sleep can go a long way.

My hope is that this reset week can be the building block for better habits. If I feel good next week, then I’ll want to repeat that and this will hopefully snowball into just overall better habits. I’m looking forward to a big reset this week.

Listening to my body

I feel like my body has been screaming at me for the last couple weeks. I’ve had a lot of muscle and joint aches and pains. I always feel a bit sore, but it’s been exceptionally noticeable the last couple of weeks.

I felt muscle tightness in my shoulders a couple weeks ago. Last week, my lower back felt tense and cause issued. My legs and knees feel like they’re laboring much more than normal.

The combination of feeling just generally sore and tight all the around has also accompanied declining performance in my workouts. My usual 5 mile run on Mondays has been a lot harder. It’s been harder to get through my interval running class on Wednesdays.

Besides an injury, I’m not sure there’s much else my body can do to tell me to chill the hell out. I know it’s time for me to take a week off to rest the body and I plan on doing just that.

Despite knowing this, it’s not something that is really easy for me right now. I’ve programmed myself to have a lot of guilt for missing workouts. Going on a run or going to the gym is something I look forward to break up my workday and take a break. It’s been a great mental hack for me.

I’ve been telling myself that next week at this point, I’m going to be happy that I took the week off.

Therapy and meditation

Mental health issues seem to be on the rise in the U.S. for many reasons. I’m happy to see that there are so many startups out there tackling the problem right now. I’ve seen a huge number of startups trying to make therapy and coaching accessible to the masses. These companies can help you find a therapist that fits what you’re looking for and navigate the messy insurance process on your behalf.

I’m of the mindset that anyone can benefit from therapy/coaching and that the stigma around therapy needs to be eradicated. It shouldn’t be just for people that have certain problems they want to work on.

I have been debating if I wanted to try to see a therapist just for overall better mental and physical health. I do think I would benefit from it, but I know it is a commitment that I need to make and I’m not yet sure I want make the leap yet. But I can see myself working with one of these startups to find a therapist at some point.

For now, meditation has served as my therapy. I view meditation as a way to become my own therapist at times. It may not work for everyone, but it works well for me. Meditation has helped me understand my thoughts and feelings more.

I meditate for 10 minutes every weekday morning to help prepare for my workday and that’s enough for me. I start my day a lot better when I meditate in the mornings and I have been doing for almost 10 years now. It’s become part of my routine and has helped me on my journey of life.

Making it

Earlier in my career, I used to envy the higher ups who seemingly didn’t have to do any of the dirty work. My first job at PwC consisted of me working 80+ hour weeks at a time grinding through spreadsheets and doing a lot of brute work. I’d get in the office at 9:30am and often work through the evenings and sometimes nights going through my checklist of to-dos.

I’d put my headphones in and grind through for hours at a time. I’d take short breaks to eat dinner at my desk or catch-up with coworkers. We’d have meetings and calls, but those were often limited to maybe 1-2 hours a day. I would often welcome those periods as time to get away from my computer screens.

Watching the partners and directors sitting in their office talking on the phone or in meetings all day seemed like easy work. They would be in and out of the office often. I had the thought that once you make it there, life is great! You can craft your schedule around your meetings and your work doesn’t force you to sit in a spreadsheet for 12+ hours.

Almost all jobs are like this. When you’re at the low levels, you do all the “dirty work” and the grinding. Then you move up and get to do a lot more of the business development and managing eventually when you’ve made it!

Now that I’ve “made it”, I realize that this is far from the truth. And there are times I do miss the grind of just doing the day to day work. My hours working nowadays are miniscule in comparison to 10 years ago, but I definitely feel more exhausted and drained. A day of 6 hours of calls and meetings often feels like I’ve just worked 12+ hours.

There’s just a lot more brain power that goes into this kind of work and it’s much more mentally draining that being able to work on a spreadsheet at your own pace.

Despite having more flexibility in my schedule, my workday is also dictated by others that I’m meeting with. I can’t just decide to take a break in the middle of a meeting and waste others’ time.

Of course, this is life and what we sign up for in this line of work. I feel lucky to be in this position and I don’t take it for granted. The grass is always greener on the other side, and being a decision maker has its perks.

I do need to remind myself to block my schedule off to allow time to myself to take a break and get some brainstorming in.

Mercenaries vs missionaries

I’ve always loved the concept of mercenaries vs missionaries in hiring. I’m not sure who to credit with coming up with it, but it’s become a staple in the startup world.

Put simply, mercenaries are employees who join a company as a job and a way to make a living. Whereas missionaries are employees who join a company because they believe in the company’s mission and want to be part of that.

Of course, a job is a job so there is some overlap and it’s also worth noting that there’s nothing wrong with being a mercenary. Some people just want to work to live, earn a paycheck, and go home.

However, when you’re building a startup where things are incredibly difficult on a day to day basis and the pay is lower, you really need to focus on finding missionaries. It’s incredibly hard to launch a business with mercenaries leading the charge.

I meet a ton of candidates who say they want to be part of a startup, but in reality, they just like the idea of being at a startup. They don’t understand that it takes a shit ton of work building that company. They are always looking out for themselves first and they are the first ones to jump off the ship when things aren’t going well.

Deciphering between someone who is a mercenary and missionary is of course a difficult task. It’s something I’m very focused on with our current batch of hires and something I’ll continue to hone in on when we make hires in the future.

Bring on the Fall

It’s Tuesday after Labor Day and summer is unofficially over. I’m excited for the fall and the events of the months ahead, but also sad that it’s over. Sophia and I had billed this summer as kind of our last hoorah or rather the last summer without kids.

We had a great summer overall. I kicked things off with our US team offsite in early June. Then Sophia and I spent a week in Maine for a family reunion followed by a week in Spain. We spent a long weekend in New Mexico in July with the in-laws. I ended the summer with back to back weekend trips to Seattle for a wedding, Scottsdale for a guys golf trip, and then Baltimore for time with the in-laws.

It was a fun summer with a lot of travel. I was able to hang out with old friends and family, and also got some quality alone time with Sophia. As par for the course at the end of summer, I’m longing for more travel and have already started thinking about the trips I want to take next year.

For now, I’m happy to be home again and getting back to my routine while preparing for the arrival of our first kid in a few months. I do feel rested and refreshed, but I know I have only a few more months of good sleep left, so I’m hoping to focus on my mental and physical health a lot this fall.

I want to make sure to be as physically and mentally prepared for the challenges of a newborn. I know it won’t be easy anyway, but at least I can go into it feeling as best as I can.

Picking stocks

After a good and tiring weekend, I felt that I recovered well and have been feeling great especially the last couple of days. I’m feeling well rested, healthy, and productive. It’s amazing what simple good habits like going to bed at the same early time and waking up at the same time can do for your health. It all starts with sleep and everything else like my health seems to fall right in line with some good rest.

On another note, the big news of the day was Nvidia’s earnings. The company reported earnings that once again beat expectations. Demand for chips continue to rise and it does not appear to be stopping anytime soon.

Of course, the stock fell 3% in after hours trading as the beat was “already priced in”. Somewhere a degenerate who has a leveraged bet on $NVDA is screaming in anger as the stock drops while the company releases great earnings.

Nowadays, I don’t follow the markets or play the single stock game as much as I used to. For one, I don’t have as much time to do research into these companies. I used to love following companies and researching it, but my day job requires me to do the same in the private markets and the appeal has mostly disappeared.

Probably more importantly though, I now have a family to take care of and I need to be more responsible with my money versus gambling in the stock market. Most of our money is being sent into broad indexes. I still have a small side pot of dry powder that I’ll gladly play with from time to time though. I’m always looking for some opportunities, just not as often as I used to.

I take off the rest of the week as I head to Baltimore to see Sophia’s parents for the last time before we’re locked down for birth. It’ll be a nice and casual end of summer trip for us. I hope to get some good rest and eat quite a bit of crab out there.

Personal financial check-up

I spent an hour yesterday doing a personal balance sheet check and analysis. I call it my personal financial check-up. I try to do this at minimum every quarter, but sometimes will do more often. This helps me accomplish a few things.

It allows me to get a snapshot of where things sit right now and evaluate performance over the last month(s). I review how much I saved and how much the market moved in some of my assets.

The first thing I check for is my savings rate compared to the last period. I knew this going in, but the last few months were expensive months for Sophia and I. We’ve had trips to Maine, Europe, New Mexico, Seattle, and Arizona so far this summer. Despite that, we were still able to invest in our liquid accounts on schedule so I’m fairly pleased.

After checking my savings rate, I decided to put in for the sale of some stocks in my liquid portfolio to rebalance a bit. Fortunately, some of my stocks have grown quite a bit this year, and it was a good time to start trimming the positions. I also needed to get some liquidity to pay off some of the summer expenses.

Last, I set-up a new savings goal and stretch goal for myself and Sophia for the rest of the year. My lifestyle creep is something I’m constantly trying to get in check. It’s been especially hard with the last few months with us trying to sneak in as much travel before the baby, and of course some baby expenses. But I find that if I set hard but attainable goals, I pay much more attention to my spending.

For next time, I’m carefully watching my crypto positions as they are starting to get outsized in my portfolio. I also may want to start shifting some of my individual stocks back to my managed funds account as I find myself with less and less time to review my portfolio.

We-Ko-Pah guys weekend

I’m feeling grateful after a fun guys golf weekend to Scottsdale. We took Friday off and flew down to Arizona on Thursday night for a short 3 day trip. We stayed at We-Ko-Pah Casino and golf resort which is just 25 minutes away from Phoenix airport.

We were able to squeeze 3 rounds of golf in at some great courses. I played okay but unfortunately left a lot of strokes out there. My swing is feeling the best it has in a long time and I feel very close to taking that next step, but it always feels like every round something else comes up. That’s golf of course.

After our early morning tee times, we spent most of the day hanging out at the casino between the restaurants, pool, and blackjack tables. We would finish our tee times around 11:30 and after lunch, we would be showered and ready to hang out by 1. We were all in bed by 9:30 every night so we had some really full and fun days.

It was great getting some good sleep on a guys trip for once. We’re finally growing up and learning.

Unfortunately, we all came out of the casino losers this weekend. I never expect to win when I go to the casino, but it makes the trip a whole lot more fun when you come out a winner. That was the only downside to the trip.

It’s not lost on me that this is likely my last guys trip before my child is born. There will be more trips like this in the future, but they will undoubtedly be different. This trip was especially special for me for that reason.

I’m feeling grateful going into the work week. It’s the last unofficial week of summer. I’m heading to Baltimore to hang out with Sophia’s parents for a few days. Then Sophia and I will spend Sunday and Labor Day back home in San Francisco.

Craziness of life

Prior to this past year, my life has been relatively calm by all standards. I’ve been incredibly fortunate that it hasn’t been crazier.

The last year things started to get crazy with my father in-law having a stroke abroad. We’ve been dealing with my in-laws and their aging and health related issues a lot unfortunately. It hasn’t all been bad though as we’re of course now expecting a newborn in November.

Our calm lives are about to get even crazier with everything going on. I had a glimpse of it last night as Sophia’s flight got canceled. I picked her up from the airport and we went to dinner. After being seated, we were hit with a pregnancy scare which ended up being perfectly at the end. But we had to leave dinner and rush back to San Francisco.

After staying up with Sophia until her early morning flight, I couldn’t get much sleep and woke up feeling just dead. I’ve been running around all morning trying to power through with coffee. I suppose this is good training as to what I can expect when this baby comes.

Life is definitely not going to get easier for us anytime soon. I’m doing my best to embrace it and power through the hecticness. Life is going to get crazy, but it’ll be rewarding.

The decline of department stores

I joke that I was raised in a Nordstrom and Macy’s by my mom when I was young. She would pick me up from school, bribe me with Burger King, and then go shopping. I hated it, but I loved Burger King so I put up with it and would find places to try to nap in the store.

When I went shopping as a kid, my parents would take me to Nordstrom or Macy’s to pick out some new clothes. I still don’t like shopping, but I do always have fond memories of these large department stores holding big events for celebrities or decked out for the holidays. It was part of my childhood.

It was a bit sad to hear that both Nordstrom and Macy’s were closing in San Francisco. I didn’t visit them much as an adult, but I had good memories there growing up and didn’t want to see them gone.

Big department stores have seemed to continue to struggle as shoppers turn online. I suspect most of the new generation that’s hitting the workforce today grew up shopping differently than I did as a kid. It’s a trend that’s been happening and will continue to happen.

I don’t expect many of these big stores to stick around for too much longer. People find it more convenient to shop online with the larger inventories and easy returns nowadays. Along with shopping malls, I’d probably guess that department stores will go largely extinct in the next 10 years.

I’m interested to see what the new trends in shopping will be.

So far, I haven’t seen virtual try-ons take hold yet despite that being a big hype in the startup world a few years ago. I’m wondering if that will eventually become a normal thing soon as technology improves.

I wonder if custom made clothing starts to take a foothold in the market. Imagine a world where you can take a picture of yourself and then have an app build you a custom set of jeans that fit you perfectly in which you can customize.

I can also see a world where department stores like Nordstrom have many more, albeit smaller outposts meant for trying on clothes by appointment and providing that bespoke shopping experience that people still love.

Perhaps I’ll start to like shopping more in the few years ahead.

The last 4 years

I’ve been chatting with a bunch of folks leaving their jobs because they are just simply burnt out from the last few years. It’s been an eventful 4 years for us in the startup world.

We had COVID in 2020 which impacted everyone, but by nature being smaller companies with a burn rate, many startups went through a brutal time. And of course, dealing with COVID was not fun either.

Then we went into 2021 which was a boom year in startup world. The free money effectively made things incredibly good… unfortunately too good. We were having fun. We were growing. But that comes at a cost of working your ass off. I know I was personally exhausted.

Then we went into 2022 when the wheels started coming off the ZIRP train. Startups were bloated and growth came to a screeching halt. The layoffs came hard.

2023 was another tough year with companies adapting to the new reality and VC funding largely dried up. More companies went through layoffs and it was a stressful period for startup builders.

In 2024, things have started to stabilize but it’s been yet another tough year. There’s lots of optimism and glimmers of hope, but most companies are forecasting a much slower growth year.

While these things are cyclical and we can expect more tough years in the future, I’d imagine the last 4 were exceptionally difficult especially those are that are earlier in their careers and have never gone through a downturn like this.

I know I’ve been impacted personally. I feel much more negative at times and I have to catch myself when my mind starts to spiral through negative and worse case scenarios. I often have to remind myself of what I’ve accomplished and learned personally over the years. These tough years will be a blip in the radar in our careers once all said and done.

I’ve done a lot more work on my mental mindset recently. I know that I’m lucky and have things good at the end of the day. I also need to remind myself to celebrate the wins and take breaks to enjoy life.

Today, I did just that. With a stressful morning of 4+ hours of calls, I had a big window in my afternoon and I decided to take a few hours off to relax and enjoy the sunny day here in San Francisco. I’m making up for the lost time now, but those hours in the sun were well worth it.

Epic weekend in Seattle

I took Thursday and Friday off to fly up to Seattle and attend the wedding of one of my good friends from college. It was an awesome weekend filled with exploring, good food, and catching up with old friends.

I spent the afternoons re-exploring parts of Seattle that I haven’t seen in a few years like the U-District and Pike Place. I got some good food at some of my old stomping grounds. One special moment was seeing the owner of Little Thai who has been running the place for 30 years. I first went there about 15 years ago and while I haven’t been back for a few years, she recognized me and we caught up.

The nights were reserved for celebrating my friends. Like always, it was amazing catching up with old friends and seeing what everyone is up to. Now in our mid-30s, we have all gone down different paths in life, but when we get back and see each other again, it’s like we are sitting in our fraternity back in 2009 again.

One thing that is different than in 2009… the recovery time needed after a long weekend like this. With Sophia pregnant, we had early exits both nights and did our best to sleep in as much as possible to get our rest. While I indulged a bit in the drinks, I had kept things under control. We had also flown back Saturday night to recover on Sunday.

Despite all this, I still woke up exhausted this morning. Even with a big rest day on Sunday and a night of good sleep, my body is still telling me that I overdid it this weekend. Getting older can suck in many ways. I’m getting more sleep and drinking less, but it’s apparently not enough still.

Of course there are times where weekends like this are worth it. I have no regret as I was simply celebrating my good friend’s wedding and if the price to pay is a day or two of being tired, then so be it.

But I also see this as yet another sign. My body is calling out to me and telling me that I need even more rest and even less drinks.

Overreactions and overthinking

We kicked off last week with a market stock decline and panic in the air. All of a sudden people had fears of a recession hitting and started selling. A week and a half later, the S&P 500 is up almost 4%.

Don’t get me wrong. There is still a possibility of a recession and more sell-offs in the future. This is the market after all. If there’s one thing I know, stocks will go down again in the future at some point.

However the overreactions to these events usually do not end well. If you had panic-sold last Monday, you would’ve missed the rally back up and left yourself in a bigger hole.

In the private markets, we often see a lot of retail investors overreact and overthink their strategies. People try to predict the future and time the market perfectly on both bullish and bearish sentiments.

The private markets do present more of an opportunity for planning based on external factors so in my opinion, it’s important to pay attention to the trends. But I often see people going all-in when things are going well, or folding completely when things aren’t going well. When you do that, you’re gambling much more than you’re planning.

Belief in equity

Since I started at Secfi in 2018, the overall employee belief in equity may be at an all-time low. If you think about the dynamics of this tough time in tech, you can start to see why.

Employees joined these promising startups in 2019-2021 when companies were growing like crazy and booming. They raised significant capital at high valuations and their equity had been significantly appreciated.

Now with the market correcting itself, their equity has significantly gone down in value. And to make matters worse, many of these companies do not have a liquidity event in near sight. The secondary markets exist for a handful of companies right now, but that’s only for a select few companies out there.

It’s hard to stay the course for many folks given the circumstances. A lot of people have just outright given up on their equity as they may not ever realize value from them, and unfortunately many of them are right.

However, everything is circumstantial depending on the company. And we know that the markets are cyclical. There will be more liquidity events in the future for a lot of companies including IPOs and acquisitions. But to get there, we’re going to need to see things start resetting which hasn’t fully happened yet.

Companies will unfortunately shut down at worst and raise down rounds. Some will emerge from this stronger. However, these things take time and we’ve still yet to see everything unfold.

Preparing for this baby

Last week my friend joked about how I would prepare for the lack of sleep with the baby. He asked if I was going to do some sort of like 2 week sleep period prior to Sophia going into labor. I think he was joking, but it honestly sounded pretty amazing. Although I’m not sure how long my built up energy would last once the sleepless nights come in.

We’re still about 3 months away from the due date, but we’ve started getting all the necessary things for Colin’s arrival like a car seat, crib, etc. Even with only a fraction of the things purchased, the space in our apartment is starting to become more and more cramped.

Everyone says that nothing can prepare you for becoming a parent and that’s kind of how I’m operating. I don’t know if there’s really anything I can do to prepare for the lack of sleep. It sounds like something I’ll just need to suck up and power through when it happens.

I’ve also been doing some reading about kids. I know every kid is different, but I like to be as prepared as possible when he comes. Perhaps that will make me sleep just a bit easier.