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Adding a free SSL certificate to Google Compute Engine

Google provides a one click install option for WordPress on their Google Compute Engine instances. This is a very economical and customisable way to spin up a WordPress blog if you’re comfortable with a Debian shell. Unfortunately it only spins up a HTTP rather than secure HTTPS instance, so here’s how to add a free SSL certificate.

Firstly, log into your Cloud console and open an SSH shell for your instance

Google Cloud VM Instance SSH login

Then in the shell, run the following commands as mentioned here:

sudo apt-get install certbot python-certbot-apache

Accept the downloading and installation of some Python packages, then to request and install a new Let’s Encrypt certificate into Apache the :

sudo certbot --apache

It will ask a number of questions such as the server hostname and whether you want to redirect HTTP to HTTPS (you should), then link to the SSL Labs server test to verify your installation.

Finally you can optionally run a dry run renewal, just to make sure it all works:

sudo certbot renew --dry-run

And that’s it!

Mastering Growth with Pirates

Mastering Growth Certificate

I recently completed the Mastering Growth online course with Harvard. As an avid listener of the Masters of Scale podcast I was aware of the content, but this course really made me take the time to reflect on the themes in the context of my role as CPTO of a startup.

The podcast episode that resonated most with me was featured in one of the lectures – Uber’s How Pirates Become The Navy. The episode is about the band of startup pirates learning the benefits and behaviours of becoming a navy. Coming from Corporate land however, I needed to do the opposite and learn when to be a pirate.

Google teaches you to plan big – if it’s not in the hundreds of millions of users or $ then it’s probably not worth doing. That implies that planning and robust debate is important, and exemplifies an engineering lead culture where scale is thought through.

When shifting to a startup, although you might get hired for scale they will give you credit for speed. The company and founders has lived through a period of survival and built a credit structure around that. If you want to earn enough credits to spend on that big scale investment, you had better show you can jump on a quick dollar today. It doesn’t really matter whether that dollar aligns with the strategy or not, what matters is that you moved quickly and you closed it. You have survival instinct.

The trick is knowing when you need to show this hustle. Anyone from corporate land can tell you that quick wins buy credits, but in corporate land there are very clearly articulated strategies and even words that will help you find wins. One example is a corporate mantra of being a “trusted advisor” – just go and get a customer testimonial that shows how they relied on your advice to make a decision. Pre-meditated decision making.

In startup land, it’s more opportunistic. You need to jump on the opportunity as soon as you see it, and then work out the messaging later. A key customer mentions a tangential opportunity? Launch an MVP and then test if there’s a market for it. Worst case the takeaway message is we moved too fast – there’s no punishment for that. Best case, you made a customer happy and a dollar. Now you can put your scale hat on, market size it, and think about whether it’s something worth planning for.

Is this a good core strategy? No, if you focused on this then your ever increasing team would be in an ever bigger state of fragmentation and disarray. As a rough rule of thumb, 20% of your effort should be launching MVPs and 80% should be landing the proven ones.

My Google Story

Dropping off my Google badge
Dropping off my Google badge

Dear team and friends,

When I was about 11, I created a Lego greenhouse that grew a real plant. That’s when I first believed that I could create technology that makes a difference in the real world. I came to Google as a level 3 just over 9 years ago to work with the best people in the world to achieve that mission. Being part of programs like YouTube Symphony only confirmed this truth. Four promotions later I hit an EQ brick wall, leading to 2 years of hard self reflection both inside (thanks Take the Lead) and outside Google (thanks INSEAD).

At the end of this period I wrote a thesis with a paediatric surgeon in Singapore. She turned up late to our first group meeting… typical university group work right? Except she was late due to performing a liver transplant on a newborn. I reflected that the ads I delivered today didn’t give me that same feeling, she reflected that she only had one pair of hands and YouTube educates the world on health every second.

In the couple of years since this experience I’ve felt a need to more deliberately structure teams to solve real world problems. Full time this was helping my awesome Publisher team find a way to fund journalism again, but at night I was kept awake by failed health startups and raising our 3rd child. My list of requirements for a healthtech role that would be good enough to leave Google for was extensive, but after a lot of sleepless nights and consultation with family and mentors, I think I’ve found one.

There are a huge number of people to thank for this journey – Neeraj, Estee, Alan, Abhay and Scott for being amazing mentors and advocates. My teams and peers across Brand, CSE and Publishers who have pushed me to be a better person and manager, but more importantly shared so many personally meaningful TGIFs, off-sites, coffees and lunches. I’m sorry for pushing so hard on PDPs and career development, but if it helped spark even one new insight into what motivates you then I leave content.

Please stay in touch, it’s a small world even outside the Google bubble.


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