I go to hackathons and they ask “role?” and I respond “Pretty girl all the MBAs want to date.”

I am a ninja rockstar unicorn with a side order of jaded hipster.

Some days I face palm when helping a start-up grow their diversity.

“We want to hire more women but we cannot treat women in our organization the same way we treat the men.”

Can’t we just treat everyone as “people” and be done with it?

I cannot decide if the start-up is saying that women need special treatment or that the start-up treats the men like shit.

Client looking to hire an experienced CTO as a guiding hand: “We can’t hire you! You’ve done too much!”

I’m sorry, I thought that was the fucking point!

Part of my job description is calling you on your B.S.

Projects fail due to a lack of communication.

No other reason.

In a conversation long, long ago…

Co-founder: “You cannot just decide to talk to the engineers or call a meeting with them. You should run it by me first.”

Me: “I’m the CTO, I don’t need your permission to talk to the engineers.”

It is good to be in demand, I just wish I knew what was being demanded of me.

Received a snotty email from someone I’ve only met once, a year ago, demanding to know why I wasn’t on a conference call at 8AM EST – I’m in PST.

Apparently, without my consent or input, someone decided that I should participate in a two hour advisory meeting without actually asking me first.

We really need a meme for overly attached entrepreneur.

You will ask your technical co-founder “Is this possible?” and the answer will be “Yes” and you will think “well that was easy” when it really isn’t.

And that’s okay, because you need to learn how to ask “What will it take?” instead.

What a lot of investors chasing Machine Learning start-ups building virtual assistants and agents don’t realise is, there is a lot more “human” in that algorithm than there is “machine” in most cases.

I’ve worked with a number of start-ups over the past three years where they are “fudging it” by outsourcing the complex “Machine Learning” part to Amazon Mechanical Turk and other micro-service-provider services.

Too many entrepreneurs focus on revenues rather than profits, much to their quarterly balance sheet’s chagrin.

I’ve met way too many entrepreneurs that were so proud they raised X dollar money from a VC.

I’ve met far too few entrepreneurs that were proud they sold X dollar money of product or services.

Removing the UI removes choice.

Chat bots are not about expanding your user’s choices but about reducing them.

No single marketing strategy will make your start-up a success.

Every marketing strategy you have tried, are trying, and will try, are what makes your start-up a success.

Your technical co-founder’s motivation, if they are willing to work for free, comes from learning new things.

Don’t ever take that away from them whilst you aren’t paying them.

If they wanted drudge work, they can take a high paying software development job at a bank.

There’s a strong signalling mechanism at work if you are an entrepreneur-in-residence and the VC fund  decides to fund or not fund your start-up.

Please stop building chat interfaces as the sole way of interacting with your service.

Even the most well-developed chat interface should provide a friendlier dashboard of options that are discoverable.

Chat interfaces should be used as a supplement to, rather than a complete replacement of, the user interaction model.

You will insist that your technical co-founder stops working on the bathroom and work on the living room for a few days.

And that’s okay, because technical co-founders sometimes need a break from working on that.

And sometimes the developer needs to understand you’re an arsehole who “doesn’t get it.”

If you envision yourself as an entrepreneur, but you need validation from other people, I guarantee that you you’ll never make your start-up successful.

People don’t validate other people until after they are a success.

Your technical co-founder will become frustrated because you ask for a feature you cannot explain why you need.

And that’s okay, because you need to rationally think and be able to describe every single feature you want.

Otherwise, you’re just wasting everyone’s time.

Especially your end users’ time.

Before you adopt the strategy of building a product without any kind of user interface, realise that you have made how to use your product completely opaque.

We have spent the last 30+ years educating users on how to interact with computers through easily discoverable user interfaces.

I see a lot of start-ups now proposing we get rid of that paradigm.

I applaud you for trying new things, but “no user interface” is still a “user interface.”

And user interfaces are like jokes. If you have to explain it, it’s probably not very good.

You ain’t shit if you can’t ship.

You will be dazzled by someone with an opinion on the best way to implement this.

We need to be exposed to lots of snake oil salesmen to be on guard for the next salesman selling a shiny bullet.

A business that’s building a web application needs to realise it requires two separate websites.

There’s the website for the app, and then there’s the website for the marketing.

Keep them separated and you won’t go crazy.

Combine them, and you’ll make your customers crazy.

This is why I don’t like software that auto-updates by default and cannot be easily disabled.

Today I had to explain to a client why the product launch is going to be delayed from today until tomorrow.

The development environment on the software developers’ computers updated at 2AM last night and everybody is dead in the water until we figure out what the breaking changes were.

If you make decisions about what you want from life based purely on money or what other people think of you, you won’t ever achieve anything and you won’t ever be happy.

This is applicable to you personally.

To your start-up.

To the products you develop.

To the funding you raise.

To ultimately, how you exit.

Entrepreneur-in-residence (EIR) has its upside.

You just shouldn’t go in to it blind.

Understand why you are accepting the EIR position.

Before you get to the point where you no longer need money:

20% of your time spent on raising money.

20% of your time spent on hiring people.

60% of your time spent on product development.

The interesting thing about VR is not what we are starting to do with it by creating experiences we’ve never had before but what we will do with it once we can do virtual porn and create experiences most software developers will never get to experience.

Sex.

Having sex with another person.

I’m talking about sex.

The one thing most entrepreneurs forget when they rush off to create a chatbot interface is that they didn’t take in to account my elderly mother-in-law who just spent twenty minutes “chatting to that nice man at the bank.”

Your technical co-founder will attempt to take pride in their work.

And you will at every step, unconsciously, attempt to make them produce work they cannot be proud of.

And that’s okay, because you needed a new developer anyway.

The old one had become too slow.

P.S. This is sarcasm.