Monday musings

Sophia and I spent the weekend mostly running errands and starting to prepare the apartment for the newborn. We’ve decided to stay at our current one bedroom apartment for at least a few months past birth as we figure out our next move in San Francisco or New York. It’ll save us a bit of rent and we won’t have to figure out how to get out of our lease.

We’re lucky we have a closet that is large and works well for a nursery. It’s a bit of a weird concept thinking of putting our nursery in a closet, but this appears to be fairly common and it’s as big as some rooms I’ve seen in New York.

Both my football teams are leaving a lot to be desired this season. My Washington Huskies lost to Rutgers in a game that we should have easily won. We seem to be the best 3-2 team in the country but keep shooting ourselves in the foot at the most inopportune times.

The 49ers had a good win, but don’t seem close to the form that we were in last year. With injuries piling up, these next few weeks could be a make or break season. Go on nice win streak and get some players back, and we can be talking Super Bowl. But if we start rattling off some more early season losses, it could be a tough year.

The Giants today fired our President of Operations Farhan Zaidi. I’m not that well-versed in baseball, but Farhan seemed like that very typical Silicon Valley analytics type executive. There were a lot of promising moments and many years ago, it felt that Farhan was going to be that elite executive that was just ahead of the curve by using data and analytics. But things didn’t work out and baseball is still a team sport that data cannot completely account for.

On the work front, our quarter ends today and we have a lot of reasons to celebrate. It was a challenging quarter that started off very uncertain, but we pulled together as a team and have set ourselves up for a great year. I’ve told my team that we should wrap up strong this week and clean-up some things as we finish the quarter. Then we all need to take a bit of a breather.

Q4 is always the busiest time of the year for us and the holiday schedule doesn’t make it easier. It’s important that we take some time to relax and celebrate the big quarter. Fittingly, it’s a heat wave in San Francisco so I’ll be taking some time to work outside and do independent work away from calls.

RIP Om Jenggot

I’m still feeling the side effects of this COVID vaccine almost 2 days later. I got caught up with a few things that needed to get done yesterday and was only able to rest starting at around 2pm. I didn’t take it as easy as I would have liked. Today,

I have some minor aches and just feel a bit tired despite a decent night of sleep. I really miss the days when I didn’t have to have these huge recovery days. It was nice being young.

On a different note, I received the sad news that my uncle in Indonesia died yesterday at age 70. He had an unexpected stroke and passed. We called him Om Jenggot. Om meaning uncle. And Jenggot meaning goatee in Indonesian. He always sported a goatee when I was young.

My Dad was 1 of 11 in his family and he was the one sent to the US to go to school. Given the large family and fact that we’re across the globe, it’s always been hard to see family.

Om Jenggot always took a liking to me as a child. He was a tailor and would send me the best Halloween costumes. I last saw him as a teenager when I went to Indonesia probably close to 20 years ago at this point. I can tell my Dad is definitely upset. He was very close to this brother.

I was able to meet his son, my cousin when he was a kid as well. I know he had another son is young as well. I hope that they’re doing well given the news.

It’s an eye opening moment for me. A lot of my uncles and aunts have passed at this point. I wasn’t close to many of them given the large family but family is family, and I need to visit back home to see family soon. I hope I can bring my son and Sophia to Indonesia sometime soon so they can meet my family.

Taking it easy

I’m feeling like shit this morning after getting my COVID, flu, and TDAP vaccines yesterday. I decided to rip the bandaid off and get them all done as they were doctor recommended for the baby.

I’d imagine the COVID vaccine side effects is probably what is taking a toll on my body right now. I’m achey and have minor chills after having a tough night of sleep. I was dressed, packed up, and just about ready to head out the door to my office when I came to my senses and decided to stay in today and take it easy.

I don’t see a need to torture myself when I have a perfectly good desk at home to get my work done. My workout can wait a day when I’m feeling better. I’m no longer young and I need to treat myself better.

This “power through” mentality definitely came from my Dad who ran his own business. I don’t think I’ve seen him take a proper sick day and stay home from the office. I carried that mentality from my youth and would always power through my colds and go to school/work. Turns out I was probably that gross jerk getting everyone sick.

Vista acquires Smartsheet for $8.4B

The news of the morning is Vista and Blackstone’s acquisition of Smartsheet for $8.4B. I’ve only been able to read tidbits on Twitter, but it appears that the price was a 40% premium over what the stock was trading for which was a big surprise.

It appears that Vista and Blackstone both thought that Smartsheet was very undervalued. Some financial highlights I saw were that the company had a $1B of revenue growing at 20% with 80% gross margins. That’s a pretty healthy topline growth in a tough year for SaaS sales at their level of scale. The margins are in-line with top tier SaaS companies as well.

The big downside to Vista is that they have struggled to generate a profit which is probably why Vista and Blackstone are salivating right now at this acquisition. They probably saw a company that had a good product and good growth which they could improve in the coming years.

Probably more exciting for them is that they saw a very inefficient sales and marketing motion that was burning too much cash. Unfortunately, I’d imagine there will be a lot of people at the company that will have to move on.

On the surface, it seems like this is right up Vista and Blackstone’s alley and they could turn a big profit here in the next few years.

Embracing the chaos

I’ve had a pretty hectic day with a morning doctor’s appointment that led to me having to rush to a lunch event in Palo Alto. After the event, I had to rush back to the city for another meeting after sitting in traffic for over an hour.

It was pretty stressful with me using the time in the car to make calls to clients and having to spend a couple hours in the evening getting caught up with everything.

In the grand scheme of things, it wasn’t all that bad of a day but I had to really take a bit to decompress when I got home as I felt like I was hopping around a lot. Unfortunately for me, I know that this will become more or less my life with kids now. I have a new appreciation for what my Dad had to do as a single father and a business owner.

It’s really up to me at this point to have a better mentality at tackling the hectic schedule. I’m someone who is very organized and likes to be early to things as to not rush. These days when I’m running meeting to meeting really throw for me a loop and it’s something that I need to learn to embrace more.

Two months away

We’re officially under 2 months until the expected due date of the baby. While anything can happen, I expect things to get really crazy starting in a few weeks.

Sophia’s physical struggles have picked up significantly recently and will continue to get more difficult. The thought of having to pack a hospital bag and being on call 24/7 if anything happens is pretty crazy to think about it.

As for my social life, I had earmarked 2 months as really when I really have to slow things down. I have one personal trip to Seattle the weekend after next and then a work trip to New York. Besides that, I plan on being largely a homebody.

It’s not all so bad. I spent a lot of this weekend getting caught up on rest and just relaxing. My body and brain could definitely use a bit of quiet time before the baby gets here. I plan on taking most of the next two months to do just that.

Friday wrap-up

I’m absolutely exhausted from the week and day. I had hoped for a fairly easy Friday to cross off my checklist, but I unfortunately cursed myself and was subject to about 5 different work related things unexpectedly. It wasn’t all so bad as the outcome of today was a positive one as we made progress, but it was stressful to say the least jumping from one fire drill to another.

It wasn’t until about 3pm today that I caught some air. A 15 minute break turned into a 45 minutes nap as I fell asleep while laying down for a bit. I’m now back at it and hoping to wrap up my checklist in the next couple hours so I can spend Friday night with Sophia.

In the craziness of the week, I barely had time to think about the Fed cutting rates by 0.5%. It’s finally nice to see rates come down a bit from the highest level it’s been in 20 years. I’m no way near qualified even to fully discuss the consequences of cutting too fast, but I know as a consumer and investor, I’m glad to see some good news on the macro front.

Perhaps it may be time to start talking about refinancing my car loan. And hopefully this sets us up for a good 2025 IPO window.

Burn out at startups in 2024

I’ve been noticing that a lot of executives and employees at startups have been mentioning that they’re feeling really burnt out lately. It’s all anecdotal of course, but it feels like this year has been the breaking year for many folks.

Burn out is nothing new in the startup world. Startups are really fucking hard. You’re constantly chasing a moving goalpost target and there’s often no one to really help you out on the work. Unlike at large companies, vacations mean you’re often also working because there’s not enough to cover you.

But if we think about 2024, I do think it makes sense that a lot more startup employees are feeling the burn.

For one, the last 3 years have been tough in the tech and startup world. Companies are spending less. Growth rates at startups have gone down and employees have to work harder to generate more revenue.

Startup valuations have also declined and there’s a mental aspect of seeing your hard work lose value. The IPO window is closed and the demands for an exit have gone up so employees aren’t seeing the liquidity that they once had hoped for to justify their work.

In addition, head count at startups have gone down as they aim to get profitable. There’s just simply more work per employee than there was in 2021.

The optimistic view is that the market will improve and companies are much more employee-friendly when it comes to burn out than they were many years ago. There will also be a hard-charging mentality when you’re at a fast growing startup and that won’t go away.

I’m curious how companies will adapt to employee burn out going forward. For myself, it’s yet another reminder that I need to take care of myself and my health first.

Practice, practice, practice

I took the morning off to attend a golf event with one of our partners that we’ve worked with for a few years. At this point, they’re more friends than business partners and it was great catching up with them.

They branched out from their day jobs almost 10 years ago and started their own firm and have been crushing it lately. They’re smart and entrepreneurial folks. They talk about how it wasn’t always easy for them. They tried a whole bunch of things that failed and went through a lot of growing pains. But that’s what starting a company is like.

After 4 years of golfing, my game is finally at a great point. It wasn’t easy and there were a lot of painful months and years. At many points, I thought that I would never get even decent at golf. I stuck with it and practiced as much as I could while also building a startup.

I’m glad I did as my game is finally starting to come around. I feel very comfortable on the course nowadays. I can confidently go up to a tee box and the ball is finally starting to go where I want it to. It’s not perfect and golf is a game of imperfection, but I’m no longer a hack on the course.

It’s good to see my years of practice finally paying off. There’ll be more setbacks in the future. That’s golf. But I have a swing for the first time ever. It feels similar to that point at a startup where you start to feel just a tad bit more comfortable that things will work out. It feels great.

Faith in humanity

I’m reading the popular science fiction novel Three Body Problem and it’s been fantastic so far. It’s a good fiction novel that does an excellent job tying in humanity and our progress with an impending alien invasion.

I’m about 75% of the way through the book and there’s two more in the series afterwards so I’ll keep things high level for now. But the premise of the book is that there’s another civilization in a galaxy far away that is looking for a more stable solar system. They’ve made contact with Earth and will arrive in 450 years.

Meanwhile, earth is preparing for the upcoming “invasion” and a group called the ETO has different views on how we should view this looming visit. About half of the group is lead by Adventists who have lost faith in humanity and believe that this new civilization should eradicate humanity.

Of course, this is a fiction novel, but the potential realism of a scenario like this is probably what’s most fascinating to me. I doubt anyone has taken a NPS of humanity on a global scale, but my guess is that it’s at a fairly low point and has been trending downwards.

As humans, we seem unhappier by the day despite the fact that the world has indeed gotten better. The advent of social media and the internet has made us much more connected, but at the same time, we’re also more privy to all the bad things happening in real-time.

In reality, the world has progressed in many ways over the last 100 years. We’re wealthier than we have been. We’ve had the most sustained peace at a global scale perhaps in human history. We have a long ways to go still as a race, but I wouldn’t bet against us for solving some of the world’s problems.

I have faith in humanity and hope that in a future alien invasion, we’ll be much more optimistic in ourselves.

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.