Archive for 2015

The past 30 days

Force Factors

As an entrepreneur, every task you’ve ever undertaken has an invisible boundary layer around it held in balance by the cost of delegation and the desire to do it your way.

Whether you have no money at all or all the money in the world, the forces at play never change, only the direction they are being applied.

Trust Is A Two Way Street

You want to perform due diligence on me to make sure I can do the work, but you don’t want me performing due diligence on you to make sure you have the ability to pay for the work.

*head scratch*

Envision using spell check

If *YOU* are going to introduce *YOURSELF* as “I am a visionary entrepreneur” to a group of people at a networking meeting, I expect you to be able to actually spell both “visionary” and “entrepreneur” correctly on your self-printed, tear along the perforated edge business cards.

The misspellings were not a joke, I know, because I asked.

Your Wozniak to my Jobs. Fight!

“Would you like to be Wozniak to my Jobs?” asked the entrepreneur trying to put a ding in the Universe via his “Uber for weed but also with cookies and pizza!” idea.

“No, I don’t think I am up for that.” I replied politely.

“I guess you’re not as good as you say you are.” responded the entrepreneur.

I nodded, smiled, and separated myself from him within 30 seconds, sure that the future-Jobs had dismissed me from his list of potential “partners” by the time I had sat down with a bowl of cereal.

In other news, Sunday’s entrepreneur brunch, just like Saturday’s breakfast, was a blast.

Intensely Handsome

Ever had really bad toothache? So bad you cannot think straight?

Intense pain takes away the person. Organizations pay handsomely to have pain cured.

A patently ridiculous state to be in


I just had group breakfast with an entrepreneur who has filed a patent on a state machine.

Someone is going to be very disappointed in the near future.

Which isn’t quite as absurd as the one I spoke with last year who had filed for a patent on storing a text string in a variable.

“But it’s encoded!”

Mediocre Talent

Attempting to hire a talented individual to an organization optimized for mediocrity is a fruitless pursuit.

Product Pitching

Build an audience that wants to listen and you will never have to say very much about your product.

There Are 10 Types Of CTO

There are two types of Chief Technology Officer.

There is the “maker” CTO and there is the “executive” CTO.

Unfortunately we use the same acronym to label both types which leads to confusion and expensive mistakes.

Impolite? Me?

Sat in office at co-working space and vague entrepreneurial acquaintance wanders in to say “Hello.”

His phone rings, and he states: “Yeah, could you step outside for a minute? I need to take this.”

I sit there, blink a few times, and say “You do realize this is my office, right?”

And without missing a beat he replies “Yes, but I need to take this call in private so you need to leave.”

Anybody want to guess what my response was?

Are you paying attention?

Happiness is a choice.

You choose what you pay attention to.

If you pay attention to the wrong things, you’ll never be happy.

Simple logic.

Building great products that are successful makes me happy.

So that’s what I pay attention too.

And I am happy.

Now you need to figure out what will make you happy, and pay attention to that.

I feel so pretty and witty and…

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.

Treatment Plant

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!

Failure To Talk

Projects fail due to a lack of communication.

No other reason.

Permission To Speak Freely

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.”

Overly Attached Entrepreneur

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.

What does it take?

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.

More human than human

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.


Bottom line

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

Proudly raised right here in The Valley

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.

Backwards step

Removing the UI removes choice.

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

Multiple channels

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.

Anything but drudge work

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.

Signal corp

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.

Talkative little so-and-so

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.

We need a place to sit as much as we need a place to shit

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.”

Older than 30 days

Pin It on Pinterest