Episode #6

Software Craftspersonship


These are not the opinions of my employer, AWS, and the only purpose of this newsletter is to share, learn through sharing, and foster some honest discourse in the community at large.

skill in the particular craft of building things…

Was using Hey.com this morning and was thinking back to this article :: https://craigmod.com/essays/software_slump/ - I have to agree for the most part. Hardware keeps getting amazingly better but seems for years that software feels mostly the same. I know it is not completely true since my phone 5 years ago was nothing like what it is today. However software does feel a little stagnant or just not as delightful as it used to be.

Personally I think that it is not always treated like the craft that it is and the years of craftspersonship that goes into making something new that delights people is not appreciated. Every once in a while something comes a lot that offers such delights but usually the first thing out of the mouth's of the greater audience is that it costs too much. Seems everyone wants the good stuff but they don't want to pay for it.

I was using Superhuman during my last gig as a VC. It was amazing and worth every penny. I left that job though and I stopped my subscription. Side note - why isn't Superhuman getting hassled by Apple - they also don't enable IAP in their iOS app? For me, in that use case, Superhuman saved me time, fixed my workflow and was delightful to use. For the record I hardly used it on iOS - it was the app on the MacOS that coupled with a nice screen, keyboard shortcuts and the overall speed on a real keyboard was incredible. I miss using it. Although, I did discontinue it right after I left since it was overkill for my personal email. BTW - you can email them to say you left your job and can't afford it and they will promptly discount it. I hope Superhuman gets into calendars next since that space is a mess.

Another service I started using is Kubera, helps you track your net worth plus the documents, passwords and information your surviving family would need to figure it all out. I have used some will writing services before and some online money tracking apps but was always thinking someone should combine the tracking with the information to help the people who survive you figure things out. Having lost a brother, I know first-hand what it takes to try and figure this out. It's not fun. Oh yeah Kubera charges money for their service. Imagine that.

I read this book quite a few years ago :: The Craftsmen, I loved every page. Discusses in detail the art of being a Craftsperson and relates it to the many types of work that you may not think, but actually are a craft. I feel that being a Product Manager is a craft and it helped me to slow my thoughts down a bit and focus on my long-term product thinking.

All this brings me to Hey.com. Email re-thought. I think it is funny that the pitchforks come out right away. Email isn't broken. I think it is. It doesn't import my 10 years of emails. Maybe it doesn't need to. It isn't using standard protocols. Well - I send and receive emails from anyone with an email address so does it really matter? It's from those guys. Ahhh yes - probably this is what bugs people the most. Since those guys take to twitter to bash VC's, bash founders and call everyone's bluff on how software is made and sold. Well - maybe it is mostly jealousy? They build good shit, they charge premium pricing, their employees like working there and they challenge the common thinking around mass-market free software that sells you out all over the place. I won't use this article to bash stuff I personally used to like that now sucks, makes it hard to cancel and drops interfaces on you that completely spoil their original use case.

Also , I am not condoning Jason and DHH since I disagree with them on some stuff and agree with them on other stuff. That's normal IMHO. Regardless, I respect their craftspersonship. If product companies approached old use cases with fresh thinking - we would probably see more of this. I applaud them for basically doing whatever they want in that process sometimes landing on something that hits a home run. Pretty sure Hey will be seen as a grand slam.

I signed up for Hey as soon as I heard about it. Guess that was early since I got an invite by the 2nd day. I finally got my addy I always wanted - smitty@hey.com. Was slightly tempted to buy yo@hey.com but 999 per year is a bit ostentatious by any stretch. Of course, some folks are complaining that 99 per year is a bit much but it's my main email now. I use email daily and if email is now better (love opt-in only), my life is not being tracked (they cut all pixel tracking, and my inbox is only what I care to see (the rest is in my feed or paper trail now). All that is worth 99 bucks to me. Email feels new and it works how I think. I wonder if they will turn contacts into my personal CRM of sorts. I know they loathe calendar development but that would be cool if they fixed the calendar. Or maybe they just stop at Hey doing email in a new way really, really well. I am okay with that.

I forwarded all my old accounts to it. I never liked gmail anyway. All of the current email clients suck or the good ones get bought or go out of business. I trust this group to stick around. Do the math on 99 per year with 25K users already trying it and they announced 70k more are in the backlog list.

What startup wouldn't be digging that annual revenue?

So love them or hate them - Hey works, is worth the money and will do fine.

Oh - on the Apple thing. Apple should just do the right thing. I have experience with this having built a few OTT startups and dealing with them first-hand. Let me tell you one silly experience so you get a sense of how Apple sees the world. We had an app update banned once or not approved let's say cause the reviewer upon checking out the app saw that in our jumbotron carousel at the top of the app that we used an images that showed something running on an iPhone, iPad, TV, and god forbid - an Android phone. We were asked to fix the image. All we did is took it out of the jumbotron during review time. We all know there are a ton of apps that are doing tricks to get around Apple. Apple has a chance to do something better with payments and in the long-run make even more money but for the moment they are just being petty. Plenty of Apple fanboys and famous iOS developers are taking to the airwaves so this is not an isolated feeling.

Puts the quite the damper on upcoming WWDC.

That's it. That email link is the real one. I am all ears.

Circuit Breaker #6

Not much to say


These are NOT the opinions of my employer, AWS, and the only purpose of this newsletter is to share, learn through sharing, and foster some honest discourse in the community at large.

Obviously it has been weeks since I said anything.

In general since taking my new gig, I am less vocal than before. Such is life. I have a large team to manage, lots of new things to learn, COVID life is making work hard and I am just focusing on my craft.

In most of my previous roles I needed to have a voice. I was raising money, or hiring, or trying to get my product noticed or trying to get Startups to come to me when they wanted to raise funds. I worked hard to get my voice heard - I wanted to build up a persona and felt I always had to say something.

Needless to say in my new role the work I have to do is not about being vocal. Yes - I am hiring so I tweet about that some. I am just not writing as much or more to the point, my writing now is not for public consumption.

I am writing more than ever to be honest, Amazon has a way with words.


In general I am busy with my craft, very busy, but my craft isn’t very public facing at the moment. It might change - I have some tests to pass first.

All that being said I am also quiet because I don’t have much to say. I am tired from the lockdown. Every day is the same. I work too much. I want my kids to go out for a day and give me and them some space. I am tired of cooking. I am tired of working out in the same spot, on the same mat, in the same corner of my bedroom I am sick of looking at.

All first world problems as they saying goes.

I am employed, my family is with me, my family is healthy and I don’t really have anything to complain about.

I have a close friend who got COVID and was cut off from his family for more weeks than I thought was needed but that was how it worked.

I have friends out of work.

I have friends and family with businesses getting crushed.

I have a friend who lost his Dad during this and couldn’t visit. Couldn’t attend the funeral.

Lots of suffering going on and yet I am complaining just due to hating lockdown.

Meaning - I really have nothing to complain about.

My solution - just keep my mouth shut.

New coping method: Vermouth Rosso and ginger ale early evening spritzer.

Stay healthy!

Circuit Breaker #5

Lessons Learned


These are not the opinions of my employer, AWS, and the only purpose of this newsletter is to share, learn through sharing, and foster some honest discourse in the community at large.

I will admit. I am sick of the lock-down. Want to get out, want to get my kids out, want to eat at a restaurant, want to stop cooking, and I want some space. Okay.

Had to be said.

I am a fortunate person. I will admit it. I have a good job, everyone in my family is healthy and we are all eating well. My finances are in good shape and so far this COVID thing won’t affect my long-term financial plans.

My kids are aware of some families that are hurting and question how do people make it through all of this. I don’t know to be honest. I have no idea what one would do to be in Singapore, have a family and no income. That would be as scary as hell.

I had my own scary phase in life.

It is my rock bottom of sorts. I vowed to never be there again in my life.

  • I was running a monthly deficit in the 1000’s - USD.

  • I had blown through that invisible line I had drawn for the amount of my savings I would spend on my second coming.

  • I had even sold my Savings Bonds - ouch. I bought a ton of i-Bonds back when they were cheap and paid a lot of interest.

  • For 5 years I had not accumulated any wealth or saved for retirement during my peak earnings years.

  • I was depressed.

I finally got out of it all. Was able to sell the F&B places - one quickly and one over time. Recouped barely anything which if you pull back on the numbers it made me even more depressed. Burnt through savings (yes - I was fortunate to have some), sold everything I had, dipped into long-term (not tax sheltered retirement stuff) and essentially stopped any accumulation in retirement money.

I bounced back. I got a gig at Yahoo and was back on the earnings trail.

I was also bruised and battered.

With all this I started to build my own framework for decision making and finances. Nothing novel but important to me.

Also the stuff I tell my kids to think about.


  • Experiment early and often in life. At some point you need to be on your way to making money and saving some. My dad always said I could do what I wanted if I made money. So I did. I also didn’t finish school. Not sure if that was a good trade.

  • Do the math at some point on real earnings. How much will you put in your pocket over say 3 years and be honest about the options since most are not in the money or liquid. Which means that if you are taking a hit on the salary and you never make it up on the options then you are losing.

  • If you want to do a Startup you are better off being the founder.

  • If you want to be in VC - you are better of doing your own fund.

  • If you want to work at a big company - then be purposeful about it. Earn and learn.


  • Start saving early. I was in mutual funds when I was 20. I still have a few of them. Compounding returns really are astonishing.

  • Don’t get hooked on debt. I have credit cards - and I pay them every month as I use them to manage cash and easily auto pay bills. I have a loan because I needed to manage the carry I owed the funds.

  • Don’t be house poor - it’s not worth it to have a place if you don’t have money. Pretty much all my real estate I made money on or hold free and clear now. I will admit Singapore is challenging but I am currently trying to pile up cash and CPF savings to buy an HDB since the math says owning an HDB is better than rent over time. Plus renting in Singapore really sucks.

  • Have a budget. I am currently hooked on Tiller and spreadsheets but their support of Asia accounts sucks.

  • Save for a rainy day or implement a proper emergency fund. 3-6 months of expenditures in cash. I hate Singapore banks so for this I use Stashaway’s Simple and have it throw some extra into funds just to keep investing. I also like that Simple isn’t instantly liquid this way I am less apt to play with my emergency money.

  • In Singapore you are dumb if you don’t use your SRS account to reduce your tax hit.

  • Nothing wrong with taking money off the table. My first Startup experience so far was my best but I blew the option wealth by holding too much and losing a ton of it during the .Com bust. I still came out ahead but the difference now is a pad in Phuket for a weekend excursion versus staying in a hotel. In hindsight, once I got all the stock - I should have instructed the broker to sell some every month to reduce the holdings. Now I am militant about selling down holdings that are too big regardless of how I got them.

I am middle aged for sure. Life actually does feel kind of short.

But I am thankful I learned about money early on and stayed on top of it.

You can too.

Circuit Breaker #4

The After


These are not the opinions of my employer, AWS, and the only purpose of this newsletter is to share, learn through sharing, and foster some honest discourse in the community at large.

I have been wondering what happens when the lockdowns expire, travel comes back and we all get back to the new, new. Notice I didn’t say back to normal because maybe this is a new normal - not the old normal.

Here are some of my predictions for things:

  • There will be a surge of working in the office since unless you are already remote or took a remote job - most people crave the office setting. It allows good separation of work and home life and due to proximity it actually means less meetings. WAH is surging the number of meetings for many.

  • Food delivery will have a big drop as most prefer to go eat out - it is not only about the food but about hanging out, being served and not having to clean up. It’s an escape.

  • Online delivery might be here to stay at new levels but the current landscape may shift and less big players find a home with people cause they can’t get their orders in from their normal source due to how busy. This is happening to everyone. I also order online for the basics and then take a walk to my wet market or store in between. At this point only the niche ecommerce is working since no one has a delivery slot.

  • Kids tolerate but essentially hate home based learning. No friends, no lunch at the canteen and no chance to chat with the teacher. Just like adults, kids love to get out and have a routine - for my kids even transiting to school is part of it. Sure home based learning for certain things is doable and maybe a great way to augment learning but the classroom is more fun. I did home study for High School, I wish I hadn’t looking back but I had no choice.

  • For higher education I think it will look like Big Tech, the big brands will grow and be able to keep charging a pretty penny but the middle of the road schools will be seen for what they are and will experience a decline. Generally higher education costs too much, is creating too much debt and deserves to be undone. This event might have kicked that off.

  • Already wrote about the Startup scene which is getting remade as we speak.

  • Gyms will get super busy cause working out at home is fine in a pinch but unless you have a proper gym at home then the real gym with all the equipment and classes is better. It’s also similar to the office issue - I don’t do well with all of the work, gym and home life mixed into one venue.

  • There will be lots of breakups when lockdown is over - people will decide that the one they thought is the one turned out under pressure to not be the one. The breakup can’t occur till the lockdown is over.

Everyone is different but this is my take.

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