Roaring 20s

Seems like everyone is in summer mode right now. My Instagram feed is full of friends traveling. A lot of my colleagues are out of office many days this month.

I spent Saturday partying with some old friends. Many of them had been living elsewhere for the pandemic and have since started coming back to New York.

Yesterday, the Euro Championship final between England and Italy was played. Bars were crowded to the brink and there were viewing parties where people were standing shoulder to shoulder.

It’s been glorious to watch everything start going back to normal.

For myself, I have a wedding this weekend and then head back to San Francisco and my new apartment. I’m excited to be back home but also realize that I won’t be home much of July or August to appreciate the new apartment. I’ll be flying to Chicago, Portland, Amsterdam, Seattle, New York and Ann Arbor in the span of a few weeks for both work, weddings, and leisure.

I’m already a bit anxious thinking about the lack of sleep, but my excitement levels are through the roof.

The end of my west coast hours on east coast experiment

I’ve officially thrown in the towel on trying to work west coast hours on the east coast. At the beginning of my 3-4 month trip to the eastern time zone, I decided that I would try to work west coast hours in order to shift work hours to when I am most productive.

I’ve written quite a bit on the struggles of this experiment over the last few months. Unfortunately the end result was just that my work hours expanded from 9am ET to 9pm ET.

I suspect that working west coast hours on the east coast would work best for individuals at companies where everyone is working on west coast time. At Secfi, we have people on both coasts as well as Europe so this was a challenge.

In addition, the challenging nature of a Series A startup just made it really difficult to contain my work hours. Instead of taking mornings off to work out, I found myself reading emails from the minute I woke up.

Of course a lot of this is on myself for setting up boundaries, but I just couldn’t ever make it work to the point of success. I am excited to get back home to San Francisco and start working normalized hours again.

Back to reality

I’ve had a hectic few weeks starting with my vacation and then leading into the 4th of July weekend where I was in Asheville for a wedding. I candidly haven’t had much time to catch up on life and work and it’s been bothering me for the last week or so. I’m back in New York and decided to skip a beach day to go into the office, workout and have a personal day.

I suppose not many would consider going to the office on a “personal” day but I needed it for my psyche as I feel like I’ve been constantly falling behind these past few weeks. I’ll feel really good after a few hours of cranking out work.

I’m in New York for 2 more weeks and then I’ll be flying back home to San Francisco for good. Sophia and I signed a lease just off of Van Ness and we’re excited to be in one place again. There was a moment that we thought we might have continued our excursion and gone somewhere else for the month of August. We were really tempted and almost pulled the trigger on heading to Baja California or coming back to Quintana Roo.

At the end of the day, we decided that it was time to head back to reality. I missed our life and friends/family back in SF. We are just about to move into a brand new office in SF and I am excited about that as well. I have not even met half our new team members in person so I’m excited to do that.

I will say that we may make it an annual tradition to try to do an extended remote work vacation every year now. Being in Mexico was a great experience and we’re excited to try to do it again in the coming year or so.

Asheville

I’m in Asheville, NC for a wedding this weekend. It’s a quaint little hippie town nestled in the south. I have heard of quite a few people moving out here for a lower cost of living as well as a slower pace of life. I can see why they chose Asheville.

The city is surrounded by mountains and there’s green everywhere. There’s outdoor activities galore and microbreweries everywhere.

Crime is seemingly nonexistent compared to other major cities. The people out here really care about creating a great neighborhood and community to live.

It’s fairly interesting when I compare Asheville to San Francisco. My twitter feed is completely filled with people trashing San Francisco for many reasons including crime, homelessness, and corrupt politicians.

They’re not wrong and SF has it’s problems, but I for one am excited to get back home. I just signed a year lease starting in July and I have no plans to move. For all it’s problems, I still love San Francisco.

A place like Asheville is a great place, but it’s just not for me long-term.

Goodbye Mexico

I’m officially back working after a week and a half on vacation. It wasn’t a perfect vacation as there was a lot of work and many things didn’t go according to plan, but I do feel energized again.

The highest of my vacation was definitely scuba diving and getting to spend time with my sister who visited for the week. Scuba diving is a new hobby that I’m really excited to continue in the future. It’s a great excuse to make the short flight to Baja every few months :)

On another note, I’m headed back to the States tomorrow after spending the month in Playa del Carmen. It was a great month overall, but I’m happy to head back. I’ve learned that while I did enjoy my month in a beach/resort town, I’m definitely not a beachtown type of guy. A month of “island life” is probably my maximum.

Playa overall has been great. It’s a tourist town, but not so completely overrun. There’s still plenty of local vibes that I loved. The people are generally great and I did love the laid back atmosphere (cervezas all day!). While seafood forward is where I like to lean, the food and particularly the diversity of the food leaves a lot to be desired.

I have caught the travel bug again though after about a year with no travel. I already want to start planning my next adventure.

For now, I’m headed to Asheville for a wedding this weekend, then heading back to New York for two weeks before finally getting back to San Francisco towards the end of the month. I can’t wait to get back to Asian food in New York. One week away.

Scuba life

We went diving off of Cozumel yesterday. It was our first dive after getting open water certified and it did not disappoint. The water was crystal clear and as calm as I’ve ever seen an ocean.

Underwater life is absolutely fascinating. There’s so many different kinds of creatures on the ocean floor and it’s incredible to see while scuba diving.

I’m a big fan of seafood and admittedly have not been as environmentally conscious as some of my friends have been, but being out in nature and scuba diving has changed the way I view the ocean for the better.

Today, we went to go snorkeling with whale sharks and had a miserable experience. I am not a fan of tour groups, but you have to go with a tour group to do the whale shark viewing. It was an early morning pickup with a nice but irritating tour guide.

Unfortunately, the weather took a turn for the worst and the family in our group were the only ones that were able to dive in and see the sharks. We never saw another shark afterwards. It of course rained on us the entire 2 hour boat ride back and we were stuck in traffic in the minivan on the way home.

12 hours later, we’re back to our apartment drinking beers to forget the day. Tomorrow will be a cenote dive and I’m hoping that it will be the big grand finale to my vacation. I’ve heard amazing things and we won’t be with a tour group so I’m looking forward to it.

Last weekend of vaca

I’m a bit over a week into my vacation and approaching the last weekend. It’s been a great week that has been both eventful and uneventful which is great. There’s been a lot of golf and equal parts lounging around doing nothing.

I golfed Playa Paraiso on Monday and Playa Paraiso on Wednesday. The courses definitely have not gotten easier and there were a lot of lost balls. My driver started coming back towards the end before one too many beers ended up taking over the round.

This upcoming weekend is going to be busy and amazing. We’ll be diving in Cozumel on Friday. Then snorkeling with whale sharks on Saturday. On Sunday, we’ll be diving in a famous cenote.

I’ve been doing an okay job at keeping the work at bay. I’ve largely been focusing on only a few important leads although that has taken up more time and brain than I would have liked.

The work is definitely piling up a bit and I need to make sure to not get too anxious about returning. I’m planning on going in with a positive mindset to be present for the big weekend and aim to get excited about returning.

In the meantime, I plan to go all out in these next few days. Lots of diving, swimming, beaches, massages, and cervezas.

Vacation mode

The odd start to my vacation has gone a lot better over the weekend. The weather has held up and I’ve been doing a lot of activities that helps me get away from the computer and away from work.

Oddly, I am writing this while listening to a work call, but I told myself that this is one call this week that I have to join so I’m happy with that. Compromise.

Words can’t describe how great it is going to bed and waking up not thinking about work but rather what fun activity I’m going to do today. I haven’t had this feeling in at least over a year. My colleagues have done a great job picking up after me and trying to limit my work time and I’m very appreciative for the chance.

Sophia and I got dive certified on Sunday despite a couple tough dives. This week will be about golfing, beaches, cenotes, and eating. This weekend will be full of diving and snorkeling.

I’ve got a full week ahead and I’m beyond excited to continue the vacation.

Positivity

It’s been a less than ideal start to my vacation. We’re in the middle of a summer storm and it’s been raining hard since Sunday. Unfortunately, given we were in Playa, there’s not that much to do when it’s raining cats and dogs. No beaches, no lagoons, no cenotes, no diving.

This has admittedly been difficult as plans have been derailed and we’re finding ourselves hanging out at home much more than we’d have liked. I even thought about just working these next couple of days while we wait out the rain.

I put that out pretty quickly after talking to Sophia. We decided we were going to make the best of it and stay positive. There’s still many different ways to unwind than going to the beach.

It’ll be a different first few days of vacation than I envisioned, but I’m excited and hoping this leads to some other serendipitous experiences.

Lesson from the wise

We’ve been making some all-star hires lately at Secfi. One of those hires is our new VP of Sales an Client Operations. It became evident to me starting last year that we would need to bring in someone who has experience scaling a sales org. It was a long search but we found the right person in Neha. She is smart, experienced and just a great person to have on this leadership team.

It was a difficult hire to make considering I have led this team from the start and I had to make sure that whoever was taking over was going to treat everyone right and actually be that person that could 10x this team. We instantly hit it off from our first time speaking and it was pretty evident early on that she was the right woman for the job.

Meeting with Neha yesterday, one thing I asked her was how it’s possible to go on vacation when you are in a high profile sales/business development role with many important leads. Your clients’ needs don’t go away and there are deadlines that don’t ever work with any sort of vacation time. It’s been a challenge for me this past year. I asked Neha for advice on this.

She mentioned that she has the same problem and her top staff always have the same problem. The reality is that you really can’t sideline your clients. Rather than trying to fight it, she said to embrace it and be okay with working with those important leads on vacation, but pass every other possible task.

It felt really great hearing that from her. I realized that I’m not the only one with this problem and that’s just part of being a leader at a startup. I’ve planned my entire week and half vacation based on her advice.

Odd start to the vacation

Wrapping up my last day of work before I take a week and half off and I got mixed feelings going into it.

I got the travel bug starting Sunday night and yesterday was absolutely miserable. It happens almost every time I go to a place such as Mexico. I had thought I was in the clear though as I made it nearly 2 full weeks without catching it. Fortunately, you can run down to the pharmacy and pick up cipro over the counter here so I was able to more or less squash it in a day.

It’s been absolutely pissing rain here in Playa for the last few days and probably for the next couple days. Not ideal weather to start my vacation, but that’s life. I’ll make the best of it regardless and perhaps use the time to just relax, get caught up on life and enjoy time with friends.

On top of everything, I’ve just got a mountain of work to do. I got some really important deals and unfortunately the timing of this vacation is just brutal with the month end happening. I’ll need to manage it though and make sure I take some time to unplug and only work on certain select tasks.

Regardless, I think it’s going to be great for me to sit time and take time off. Get away from the day to day hustle and focus solely on the super important items and getting back to creativity.

Unplugging

I played 18 today at Gran Coyote. It was a great first experience doing the resort golf thing. The course was brutally difficult. There wasn’t much forgiveness off the tee… no other fairways to hit into. Once you slice or push right, you’re gone. My irons and putting were on point. Unfortunately I completely forgot how to drive the ball and was fighting an awful slice all day. It was frustrating and I wasn’t able to fix it on the range after.

Of course tomorrow I’m going to pick my driver back up and my irons will be all over the place. That’s golf I guess.

On another note, I’m preparing to take a week and half off starting this upcoming Wednesday. I’m already starting to think about which meetings I can take and which I won’t. I just realized today that I’ve completely forgot how to unplug which is obviously a terrible thing.

I think the combination of the pandemic, lack of vacation time and work demand being through the roof has really changed how I view work-life balance. I suspect a lot of other people are in the same boat. This likely doesn’t bode well for us as a society.

Being in Mexico has really opened my eyes a bit. There’s much more of a work to live type feel here, especially being in Playa. I’ll need to find balance again and it starts with my vacation this upcoming week.

Startup karma

On Tuesday, I wrote about what happens when things seem to never go well in startup world. Admittedly it was a tough start to the week and been a tough month overall.

Of course, this seldom last long and fortunes seemed to turn starting yesterday for us. Good news after good news started piling in for us on seemingly every front yesterday. Maybe there is such thing as start-up karma.

There are so many ups and downs in the startup world, but things move fast, really freakin’ fast. One day you can be down in the dumps and the next will have you jumping for joy.

I’m really excited for the rest of this week and next. I’ll be heading out to take time off on Wednesday, but there’s a lot I want to accomplish in the next coming week until I do.

Tax (or not) the rich?

The news article of the past 24 hours was the leaked taxes of billionaires which showed that they do not pay much in taxes. This is not news to anyone with a background in taxes or finance but of course, it’s an eye popping headline that has gone viral.

As part of this news report, many news outlets and reporters have taken this information and started publishing a “True Tax Rate”.

I want to be clear in that this is misinformation and misleading. What these 4 billionaires have in common is their appreciation in wealth is due to appreciation in stock which is not taxed until you actually sell that stock. Effectively, what people are arguing by reposting this is that we should be taxing people on their unrealized gains in stock. This is a tax policy (aka mark-to-market) that makes no sense.

You don’t realize any cash until the sale. Why should you be taxed on something you haven’t locked in? If we wanted this policy, we’d also have to apply it to homes and real estate. No one should be taxed on appreciation of their home prior to selling it.

Now before people come after me, I’ll address the elephant in the room that I am in favor of taxing the rich. I simply just believe in effective tax policy that encourages behavior rather than adding more patches on the sinking ship that is the tax code.

So what is my solution if I don’t believe in taxing unrealized gains? Surprisingly, I believe in a wealth tax. Albeit, one that makes more sense and encourages good behavior.

I would love to see a wealth tax imposed on the ultra wealthy that allows the ultra wealthy to avoid this tax by deploying their capital into charitable organizations. Let’s say we implement a 1% wealth tax on those 4 billionaires above. Warren/Jeff/Mike/Elon would be able to avoid this 1% wealth tax by donating 1% of their wealth to charitable causes instead.

If they don’t believe in the government allocating their capital correctly, then they can choose to pick who can. Even the staunches supporters of capitalism can get behind this. The idea of capitalism is to deploy capital and well we’re encouraging that with this wealth tax.

When things don't go well...

The last month and some change have been challenging. It’s just been one of those stretches where it feels like not much is going our way.

A mistake here, a missed opportunity there, deals lost, candidates declining your offer, the list goes on. In truth, this stuff happens all the damn time all year long in the startup world. For some months, it just happens more than the wins. This past month has just been one of those months.

I’m frustrated by this. Like many other builders, I set a high standard for myself, the organization and the goals. I too want record breaking month after record breaking month in a graph that just goes to the top right.

Of course, this is not what happens in practice. There are many bumps in the road and often times the most successful startups I’ve seen have had prolonged stretches of this.

It’s been a frustrating 24 hours especially as a few things in particular have been bothering me. At the end of the day, I need to remind myself of the following:

We are growing like crazy and have some amazing projects in the works.

We do have an amazing team that is smart, dedicated and hungry.

We are having a record breaking year. A bad 30 days does not define the year.

And despite a tough last month, we can still be on a graph that goes to the top right.

June in Playa

I’ve been so shitty at writing daily the past few months and I don’t feel great about it. I think I’ll make it my half year resolution to make more time for it and start writing first thing in the morning.

For now, I’m set-up in Playa del Carmen for the month of June with Sophia and my friend Alyssa from high school. It was a crazy decision that we thought was too good to pass up. We’ve got a gorgeous condo with a rooftop pool, deck, bar and 3 bedrooms. My rent isn’t that far off than my San Francisco rent and cost of living is significantly lower.

The food has been fantastic so far. I’ve eaten tacos and seafood pretty much for every meal over the last 5 days or so. A ceviche lunch sits really well within my diet. Delicious protein with no carbs. We’ll see how I feel about the food in a week or two. I’m already starting to crave Asian food and variety.

Work has been pretty good. I’ve got a good set-up on the top floor and alternate between the deck and the air conditioned kitchenette. I haven’t had too many hiccups getting work done despite being in paradise.

I’ve joked that I don’t think I’ll ever want to leave here and I just want to work remotely from here forever. Of course, I’d imagine that by the end of the month I’ll be itching to get back to SF or NY, but we’ll see.

Show me the money

I’m feeling great today. Slept the best I have in over a week and I feel rested headed into my last weekend in New York. Hoping to continue that trend through the weekend and next week in Mexico.

On the public markets - meme stocks are going crazy again and I’m at the point where I don’t think they’re going away anytime soon. Retail investors have money and they are bored at home. Just when we thought the market was headed for a correction….

I won’t be surprised to see crypto activity pick back up again shortly. Money is plentiful right now and putting are looking to put it to work.

In the private markets, I can’t imagine a better time to ever start a business. Angels, VCs, and celebrities are throwing money at companies right now. My daily newsletters highlighting new funding rounds is getting longer and longer by the day. This is across all industries and sectors.

For myself, after making a sizable angel investment and investing in my girlfriend (now fiances), I am a bit cash poor and admittedly have a bit of FOMO from missing out on the dip. This may be fortuitous in the long run. Time will tell.

The fix to my experiment?

Yesterday I wrote a 2 month update on my west coast hours living on the east coast experiment. Last night, I had trouble sleeping (again) after trying to go to bed early and ended up falling asleep after a couple hours of laying in bed. This morning, I woke up at close to 10am and felt the best I have all week. I ended up sleeping over 8 hours still.

It kind of hit me then and there on perhaps why my experiment hasn’t been as successful: I’ve been trying to force things too much. One of the benefits of working west coast hours was to get more sleep and go to bed later — well I’ve realized I’ve been trying to go to bed earlier in order to wake up earlier. It’s a silly realization that for this to be successful, I’ll need to just let things happen a bit more naturally. Let me body decide when to go to bed and wake up.

During my last week in New York and the next month in Playa del Carmen, I’m planning on just going with the flow. If I need to stay up later, I’ll stay up later and go to bed when I want. I’ll wake up when I want (within reason) and try not to force the gym sessions and activities in the morning.

This experiment was about finding my ideal sleep/work/leisure schedule and all I’ve been doing is trying to shift my sleep/work/leisure schedule around rather than letting my body decide.

We’ll see how it goes.

The west coast hours on east coast experiment - 2 month update

For almost two months, I’ve been living in New York City while attempting to work west coast hours. My hope for this experiment was to shift hours to a schedule that what I believe is my natural preferred work hours. I wrote about my experiment last month at my one month check-in. Last month, I wrote that it was a mixed bag of results which some nice things, but some not great aspects. Unfortunately, things maybe have gotten worse since then.

Here’s some of my notes and thoughts on some of the aspects that I was hoping would improve with this experiment.

Sleep - By far my biggest disappointment has been related to sleep. I was hoping that I would be able to sleep better at night, wake up to no alarm clock, and be much more energized throughout the day. It’s almost been the opposite effect despite the fact that I am a night owl. I tend up to stay up later due to work and I don’t get time to wind down before bed. Because of that, I’ve taken much longer to go to bed than usual. I haven’t been able to sleep in as well on the mornings - yes there have been a few mornings where I wake up feeling great, but it’s been so inconsistent that I am typically feeling worse on a day to day basis.

Exercise - Probably the best part of working west coast hours is that I get to go to the gym in the morning. It’s really nice being able to wake up, get a sweat in and go to work uninterrupted but I also feel slightly less energetic in the mornings. While more consistent, my work outs feel less impactful.

Work hours - This is something that I knew was going to be a challenge and it has been a struggle. I’ve been pretty good at blocking off my mornings, but occasionally I’ll have a meeting during my mornings that I was supposed to have off. That of course expands my work day. Furthermore, working through the evenings have been anything but enjoyable. My best hours to get stuff done is typically between 6pm-9pm. What I found is that it’s perhaps not the hours that make it my most productive, but the fact that there’s less distractions during those hours. It’s been tough working until 9-10pm every day.

Given that it’s largely been a negative experience for myself, I’m not ready to throw in the towel just yet. I have a theory that a lot of these issues could just be stemming from the fact that my life has been insanely busy in New York and I’ve just been exhausted overall since I got here two months ago.

I’m excited to continue the experiment in Playa del Carmen where things are hopefully a bit more relaxing than New York. Perhaps that’s when the true productivity is going to come from this experiment.

I proposed and now have a fiance

I proposed to Sophia on Saturday after 3 years of dating. It’s still a bit of a surreal feeling that I’m engaged to the love of my life. She’s an amazing girl and I’m truly lucky to be her fiance.

I had planned on picking up he ring during our two month New York trip but I wasn’t sure when or where I was going to pull the trigger. I ended up deciding that New York was perfect place to propose and set plans in motion.

I was lucky to have a friend bring me to his diamond guy which ended up being a great experience. The diamond district in New York is a trip. I’m not sure if I’d go as far to say I liked going there, but it was an experience I’m glad I had. It took me a couple trips to pick up the diamond I wanted. Ultimately, the first diamond she brought out ended up being the winner - it’s the first one that caught my eye and it was perfect.

My two best friends were in town with their significant others to “celebrate a birthday". We turned her birthday weekend to our engagement weekend.

I decided to get on one knee on my roof of our apartment that we’re staying it. It ended up working perfectly. It had great views and we had the roof to ourselves. I even had two friends hiding in the pool area taking photos. We had some great pictures and a video from the proposal.

Sophia had known that it was likely to happen that day all along. There wasn’t one give away but she put everything happening together and it was just too perfect of a weekend to get it done. We had some funny moments to discuss afterwards.

We ended up partying all day and I booked Pera in Soho for about 20 of us to hang out. COVID restrictions made us sit the entire two hours, but we played a bit of musical chairs to hang out with each other. I ended up surprising Sophia with some of her friends who came to town. It was a blast and I’m glad Sophia got to celebrate with her friends.

I don’t think there’s many good reasons to stay out as late as we did at our age, but I suppose my engagement should be one of them. As I write this on Monday at 9:30pm, I’m halfway asleep and today was a struggle.

I’m looking forward to catching up some sleep and enjoying my last week in New York. I’m even more excited to get to Mexico where I’m hoping to catch up on a lot of rest and relaxation. NY has been great, but I feel like I’m 2 months of sleep behind.