Alex MacCaw

JavaScript programmer, O'Reilly author.

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CEO Coaches

Every world-class athlete has a coach: every tennis player at Wimbledon, every golfer in the PGA, and every hitter in the MLB. An athlete without a coach is incomplete.

So, why don’t we think the same way about coaches for CEOs? Perhaps it’s because of the idealized notion that strong leaders should be stoic and invulnerable. Perhaps it’s because it’s harder to quantify the impact of coaching on the health of a company and the bottom line. Perhaps it’s because we don’t value mental health the same way we do physical? I’m not sure, but it is my experience that coaches are absolutely crucial for growth in all areas of life.

At the start of this year, I was squarely in the ‘no-coach’ camp. So, when our COO Luke broached the subject of me getting a coach, my initial reaction was negative. Things were going well, the business was growing, and people were happy. What could I learn that I...

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My life is random

All the best parts of my life are due to pure chance. From life-changing relationships to the closest friends, it’s all completely random.

Sometimes I think back to some of the single actions that ended up changing my life forever.

That time I danced on a specific side of a room and met a cute girl that I ended up dating for four years. Or that time I pushed myself to attend a dinner I wasn’t looking forward to and met a mentor that changed my entire perspective on how companies should be run.

I even met a good friend through whois when I was trying to buy a domain-name he owned. That friend would later introduce me to my co-founder and many of the key people in my life. What if I’d bought a different domain? Or hadn’t offered him brunch as payment? My life would be substantially different that’s for sure.

It can be scary prospect, the idea that one’s life is random and that you...

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I’ve been experimenting with building a few ‘life-hacking’ tools that help motivate me and optimize for perspective in my life. One of these tools is a Chrome extension called Motivation.

Motivation replaces your new tab screen with a counter showing your age incrementing in real time. It seems to have a struck a chord–22,000 people use it weekly. It’s a simple tool, but it helps me think about perspective a bit more, which in turn helps me optimize my time.


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I’ve always believed that improving tooling and basic infrastructure is an incredibly valuable way to spend time. Some of the companies I admire most – GitHub, Stripe and Twilio – are founded on these principles. By improving basic building blocks, you can enable a whole new generation of companies to innovate.

To take one example, combine three APIs - Google Maps, Twilio and Braintree - and you enable a company like Uber. Clearly there’s a lot more to Uber but I think it’s safe to say they would have struggled building out all three APIs at the same time as bootstrapping a driver marketplace. Infrastructure is crucial for innovation.

Which brings me neatly onto what I’ve been working on for the last year - Clearbit. For most businesses getting quality and accurate data is incredibly painful. Often it means relying on APIs designed before the modern web was even conceived, or...

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An Engineer’s Guide to US Visas

I’ve written a post on US visas on’s blog.

Gather a group of foreigners together in San Francisco, and the topic of conversation invariably turns to visas and immigration. For many of us just getting to America is a feat in itself. Overcoming the regulation, hurdles and bureaucracy that encompasses the US visa system is a shared and painful experience we can all relate to.

Five years ago, when I was working back in England, I wanted nothing more than to emigrate and join a tech startup in San Francisco. The trouble was I had no qualifications, no degrees and no connections. It’s only through a great degree of persistence, determination, and the support of some wonderful people that I’m living out in SF.

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Structuring Sinatra Applications

I’ve written a post on Sourcing’s blog about structuring Sinatra apps.

I love Sinatra. I use it for practically everything. For me, Sinatra has the perfect blend of simplicity and abstraction. I can understand the full stack, dip into the source when I need to, and extend the framework how I see fit.

However the bare-bones nature of Sinatra can come at a cost. Sinatra leaves much more of the decision making around your application’s structure, layout and libraries up to you. This can be a bit daunting if you’re just getting into Ruby web app development, which I think is one of the reasons why Sinatra is mainly the realm of more experienced developers looking for a bloat-free alternative to Rails.

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A Startup’s Guide to Hiring

I’ve written a post on Sourcing’s blog on how to find and hire software engineers.

As a founder and CEO, your role will increasingly turn to two major areas: hiring the right people, and ensuring they stay. We’re going to tackle the former area in this article and discuss a good framework for hiring engineers.

Every company’s hiring process is slightly different, and yours will likely evolve as your company grows. However, it’s important to set the right foundations in place since hiring the right people is crucial; it will make or break your company.

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A programmer’s legacy

One of my favorite things to do is looking round churches. I’m not a religious man, but whenever I visit a new city invariably the first thing I explore are the local churches or cathedral. To me, they represent timelessness and stability. They also represent a legacy. Somewhere there’s an architect whose life work was poured into that building. And here it is, standing hundreds of years after its designer has long gone, for all to see.

Legacy is something we programmers struggle with. It’s rarely discussed, and when it is it carries a negative connotation. Legacy code is a term that runs shivers down our spines. We rarely think of legacy in terms of making a mark.

I think we all have an urge to mark our stamp on this world, to graffiti ‘I was here–don’t forget me’. Yet, as a programmer, where is my legacy? Practically every program I’ve ever written has either been re-written by...

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For as long as I can remember I’ve wanted to run my own business in San Francisco. A few years after I moved to the city, after a lot of jumping through visa hoops, I finally have the opportunity. After four months of development and iteration, I’m excited to release, a tool to help you find and hire talented software engineers.

The idea stems from a problem that I had at both Twitter and Stripe: finding software engineers is a really hard and time consuming problem. There’s a shortage of good talent and the demand is incredibly high. It’s an incredibly inefficient process that can take months and cost you tens of thousands.

To find engineers, I resorted to the process of manually going through my Twitter followers and reaching out to them one by one. Out of about a hundred people I contacted, we hired three. While I was happy with the conversion rate, I couldn’t help...

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An Engineer’s guide to Stock Options

There’s a lot of fear, uncertainty and doubt when it comes to stock options, and I’d like to try and clear some of that up today. As an engineer, you may be more interested in getting on with your job than compensation. However, if you’re working at a fast growing startup, with a little luck and the right planning you can walk away from a liquidity event with a significant amount of money.

On the other hand I have friends who have literally lost out on millions of dollars because the process of exercising stock options was so complicated, opaque and expensive. Believe me, you’ll be kicking yourself if this happens to you, so why not arm yourself with some knowledge and make informed decisions.

This guide is an attempt to correct some of the imbalance in information between companies and employees, and explain in plain English the whole stock option process.

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