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If you're under revenue pressure and want to grow, this space is for you.

From doubling a $250M Microsoft segment to founding Blacfox, I've learned through wins and stumbles that sales and marketing mastery creates true economic freedom.

25/08/2026

This is Orlando Ayala.

Years ago, at a lodge deep in the Oregon woods, he stood in front of Microsoft's top eighty executives, Bill Gates and Steve Ballmer among them, and told them the company had stopped listening to its market. He walked in believing it would end his career. It did the opposite. That meeting set Microsoft on a long walk back to its market, with executives sent out for a full year to do one thing only: listen.

Orlando is the reason the word "Listening" sits on the cover of my new book. My whole thesis is one chain: income comes from value, value comes from understanding, understanding comes from listening. Orlando lived that chain at the highest level, and he paid for the lesson with the biggest risk of his career.

Machines are brilliant at handing you back what you already believe, dressed up as "feedback." But a market, a customer, must be heard, person to person. Nobody understands this better than the man who once had to force a giant to listen.

So when the time came to decide who would write the foreword for the new book, there was no shortlist. There was one name.

Thank you, my friend. For the word, for the example, and for the friendship behind both.

24/08/2026

We built an entire campaign on market research that turned out to be fiction.

Nobody lied to us. We did that part ourselves.

We were under time pressure. A member of my team asked an AI to review the market’s feedback for us. It swept up every analyst report, every vendor whitepaper, every review site, and handed back a summary so clean you would happily have paid a research firm a small fortune for it.

We built the campaign messaging on it.

The campaign failed. Completely and undeniably.

So we did what we should have done at the start. We picked up the phone and called actual buyers.

What they told us sounded almost nothing like what the machine had told us.

Working out exactly what it had missed changed how I run Blacfox.

Here's why I am telling that story this month. In August, researchers at Harvard and MIT published 8.3 billion AI personas. Roughly one for every person alive. The idea is that you can now test your product, your app or your agent on a synthetic population instead of on real people.

I did not want to argue with that from an armchair. So I've been field testing this aggressively, across a sample of 500 humans in the United States - more on that to come.

Some of the brightest minds in the world are pointing AI at the wrong job.

This week’s essay makes the case, and shows you the one thing a copy of your buyer can never hand you.

Link in the first comment.

21/08/2026

This lunch took months to earn.

A few months ago I came home from Microsoft in Redmond with one thing stuck in my head: the energy of a winning sales team. Blacfox is a B2B go-to-market agency. We live so close to the sale of our clients' products that a winning sales culture is not optional for us. It is the job.

So I sat down and wrote out every trait of a winning salesperson and a winning team. The traits that, if you truly possessed them, would make it near impossible to lose in a revenue role. That list became the Blacfox Sales Charter: twenty principles, one north star.

Our Head of HR, Rachel, decided that a published charter is not enough. She wanted to make it our culture.

She turned the charter into a game. One hour, every Friday, teams randomly assigned, each one showing how well they understood and lived the principles. Blacfox is a competitive bunch, so there were some heated moments, to say the least. We contested to the death.

This team pictured here emerged victorious. Which meant I got to honour principle 19 in person: when someone does something great, we celebrate. Lunch at one of our favourite spots in Century City.

Congratulations, team. Richly deserved.

The full charter is in the first comment. Take it, edit it until it sounds like your own, then tell me what you changed.

20/08/2026

The room went quiet the moment she started to speak.

Earlier this year, Sanyu Dillon was inducted into the AMA New York Marketing Hall of Fame. As part of the team that hosts the event each year, I get to meet some of the greatest marketing minds alive. Being wowed comes with the territory.

This was something else. No fireworks. No volume. Sanyu spoke in a calm, almost hushed tone about her love of books and the connection between a book and its reader. We hung on every word. She had the room mesmerised.

But the moment I will never forget came after the award.

She stayed. She moved through the front of the room, connecting with the people in it. I was one of them. As an author, I tried to tell her what her words meant to me. I made a mess of it. She listened intently anyway.

At the time, I was negotiating a book deal with Wiley, my publisher of choice, and I asked for her advice. She gave me her contact details and offered to help. Remember, this is the President of Penguin Random House, the largest trade book publisher in the world.

When I called, she answered. No gatekeepers. New authors know how hard it is to learn the rules of the book game. Within days, she had given me some of the best guidance I received in the world of publishing, and a top literary agent was personally advising me, at her request.

I cannot put a price on any of it.

That is leadership. The rare variety of care that extends a hand to a stranger, and creates opportunities for others to ascend.

And the ending writes itself: I am now signed with Wiley. The new book is on its way, on the precise way humans and AI must work together to win revenue. Every opportunity it creates for someone else will be my chance to pay this forward.

Thank you, Sanyu.

19/08/2026

Yes, that is a drip in my arm.

A stretch of heavy travel finally took its toll. A few weeks ago I found myself at an IV bar: vitamin C in one arm, compression boots on both legs, blanket, the works.

In this week's article I set some homework. Write down your last three purchases, then name the want behind each one.

Fair is fair. Here is one of mine, done in public.

The purchase: one IV drip. The want: to feel energised again. Nobody prescribed it. Nobody assigned it. I wanted my energy back, and I paid to have that want appeased. You'd have to read the article for the context (makeitrAIn dot media).

Now notice the room I am sitting in. Not long ago, this type of business did not even exist. Nobody ever needed a vitamin lounge. Then enough tired humans wanted one, and commerce grew a new limb. It always does. All commerce is underwritten by human desire.

A machine will never sit in this chair. Not because it has no veins. Because it never wants anything enough to run itself empty chasing it. And if this does not make complete sense, check out makeitrAIn dot media.

Your turn. Last purchase, the want behind it. Drop it in the comments.

18/08/2026

24 years separate these two photos.

The first is my graduation. Look at that boy. He has no idea what is coming. The companies, the books, the grey hair.
But he has the only thing that matters. He wants. He wants a better life. He wants to break out the trap.

Nobody assigned him that want. No brief, no prompt, no instruction. He crossed that stage on a desire he felt deep inside. And that same desire, refuelled a thousand times since, is what put me in the second photo, at the Blacfox offices, surrounded by a team, still building. Still wanting.

Here is why I share this. In 24 years the technology around me has changed beyond recognition. The wanting has not.

Machines calculate, generate, optimise and execute. Brilliantly. But no machine has ever wanted to walk a graduation stage. Not one has dreamt of starting a company. No machine looks forward to a family outing.

Desire is the one thing we have never built in a machine. Desire it is the thing that holds up the entire system of commerce. Don't believe me? Ask anyone the last time they deliberately bought something they didn't want want.

Every graduation stage is a runway of desire. Every business, every job, every purchase is someone's desire, manifest.

The machines will never replace your wanting. They cannot. They are coming to serve it.

If desire underwrites commerce, the only skill that matters has not changed in 24 years: Listening. This is why I am throwing everything behind Power Listening (more on that to come).

Read my full article for the detail. Link in the first comment.

17/08/2026

To cake pop or not to cake pop.

That is a question no machine will ever ask itself. The reason why is the most reassuring thing I have learnt about AI all year.

It started with a stranger’s post about machines becoming “the new customers.” It ended with me stress-testing my entire life’s work against the most extreme AI future I could imagine: agents doing absolutely everything, humans with nothing left to do but consume.

What survived at the bottom of that scenario is the subject of this week’s essay. Link in the first comment.

15/08/2026

Saw this in Cape Town this morning. Immediately thought of Sahil Bloom's message about recovery time. Didn’t realise the big guy had a quote about this too. If we minimise recovery time each time we hit a low, the accumulated impact over years is profound. Just focus on getting back up.

28/07/2026

A hummingbird flaps its wings up to eighty times a second.
It does that to stay exactly where it is.
To pay for it, the bird drinks eight times its own body weight in nectar a day, feeds every ten to fifteen minutes through daylight, and at night shuts its own metabolism down by more than ninety per cent, because an ordinary night's sleep would kill it.
All of that, to hold a static position over a flower.
Hovering is one of the most energetically expensive things any animal does. Staying in the same place is the most expensive flying there is.
I keep meeting revenue leaders flying "static." Long hours, real skill, no shortage of effort, but feeling stuck.
The conclusion they reach is always the same. Flap harder.
It is the wrong conclusion, and the animal kingdom has already worked out why.
There is a bird that solves this problem. It is not the eagle.
Full piece in the comments.

15/07/2026

The same month: $1.2 billion of agent revenue, and a third round of human layoffs. Salesforce's agents crossed $1.2 billion in ARR in May, up 205%. In June, the same company cut people for the third time in nine months.

Every founder I talk to now has both slides in the deck. The agent slide and the layoff slide.

Both are real. Neither is the question.

While the market argues agents versus humans, the question that decides your next quarter goes unasked. Where does the truth about your market come from?

Yesterday I published the full argument, along with the AI policy we run at Blacfox after learning this the expensive way.

Link below.

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