No, I won't sign your NDA

Every now and then, I am asked to sign an NDA before reviewing some of the initial details of a startup that has reached out to me.

Like an angel investor or VC, I do not sign NDAs to discuss your startup.

Here's a quick summary of why I stick to this:

1. Ideas aren't unique; execution is. My focus will be on the 10,000 decisions required for execution, not just the initial idea.

2. Avoids conflicts. I meet with many founders, and I may have already heard similar ideas (or will hear them in the future). Signing an NDA creates unnecessary legal risk that I might be accused of sharing information, even if I haven't.

3. Reduces friction. It eliminates paperwork and administrative friction that slows down initial discovery.

4. Filters for quality. It helps filter for founders who understand that the primary value is in execution and who are coachable.

That said, I do, of course, always act in a professional manner, treat the information I review as strictly confidential, and use it only in the best interests of the company and founders, even without a formal NDA in place. 

Of course, my formal engagement contract includes a confidentiality clause, since we're dealing with very important lower-level details.

Leader code switching

A big part of senior leadership is knowing how to "Code Switch".

Knowing what to say, how to say it, and when to say it is critical to success.

AI has replaced me!

One of the product leaders I work closely with as a Fractional CPO has trained an AI Agent on all my public posts on product, leadership, start-ups, etc.

Now he checks all his work with it before running it by me.

Has he made me redundant, or has he made himself indispensable?

I still have a much better sense of humor (and incisive taste and judgment) that it can't match, though.

I still think I win this round.

How about you? Have you been replaced, or made yourself indispensable?

Did you stumble into a great new business?

If one or more of these things meaningfully change, it's a different business.

• Product

• Business model

• Target customer

• Geography

Don't do it casually or unintentionally. Each business requires a meaningful new investment in sales, marketing, customer support, etc.

This, of course, needs significant new capital/cash flow.

Non-verbal signals that are working (for or) against you

Rightly or wrongly, you can quickly (and detrimentally) communicate your seniority with your personality, word choice, and general confidence in any given room.

People can try to look past it to hear the substance of what you're saying, but the fact is, it's very, very hard and takes enormous intention and cognitive load.

Don't leave it to the other person/people to make up their own mind. Own the signal.

What signal are you sending?

What signals do you look for?

Effective M&A Strategy

What if you had unlimited money to buy companies to accelerate your business? How should you think about M&A?

That’s a "kid in a candy store" style question, right?

First, you would want to map out the entire business architecture and strategy for the next 12 to 24 months.

Then you want to ask the question "which companies might help us accelerate the execution of this strategy?"

But of course, you must factor in the enormous cost and complexity of integrating different tech stacks, cultures, and processes. Successful M&A is hard, costly, and disruptive.

In order to qualify as a candidate to meaningfully accelerate part of the business strategy, the target company would need to have a massive unfair advantage in the particular category of the business you're trying to accelerate.

OR

You should really only be considering companies you can strip for parts without planning to integrate their legacy tech, culture, structure etc.

Which parts?

A "part" might be “the team”. For example, you could buy a small amazing little consumer product startup and turn them into one of your cross-functional product squad to work on a specific product mission/problem.

A “part" might just be something like their customers. Take their database, migrate some percentage over to your core products (assume only a conservative fraction), and kill the rest of the business.

Ruthless? Yes.

Efficient. Also yes.

Everything else quickly becomes a quagmire.

AI supercharges whoever you already are

AI has a wonderful way of supercharging your superpowers and your weaknesses.

If you tend to talk a big game and lack rigor in your thinking, then AI will be a great venue for you to talk/think endlessly and create mountains of AI slop.

That's why AI tools require top 1% people to produce high-quality 100x outcomes.

Measuring KPIs and OKRs when things are fundamentally broken is DUMB.

Measuring KPIs and OKRs when things are fundamentally broken is DUMB.

Why?

Because it's like asking what the score is when the players are in the wrong ballpark.

Get to the right ballpark, start playing the right game, and then you can start to ask what the numbers are.

Alignment is the engine that powers disruption and success.

How do you know if your startup or scale-up is working well?

Everyone is aligned and working on basically the exact same thing for the exact same reason - at the same time.

Alignment is the engine that powers disruption and success.

Agent management and orchestration

Every management job description will soon include “agent management and orchestration” as a core skill

SaaS vs. AI

Running a SaaS company?

Your pitch must be something along the lines of...

"AI lets you ask questions. We give you answers to questions you didn’t even know were worth asking."

You must also have a comparison chart that justifies your existence beyond AI chatbots and AI-generated software.

I've developed extensive thinking on this for my portfolio of startups.

Reach out if you'd like to get access

Stop spinning plates and start landing planes

Value creation may not be where you think it is

You (and your manager) should not be measuring your value creation by how many plates you have spinning in the air, but by how many high-quality, needle-moving deliverables you land FAST.

1 high-quality deliverable that moves the needle for the business is worth 100x 5 plates spinning in the air.

The same is true for your Startup.

If your users/customers don't feel it, chances are high it's worth ZERO.

Deliverable quality: Great teams vs. Mediocre teams

Mediocre teams: Along every link in the chain, the clarity of requirements and the quality of the outcomes degrade.

With teams like this, you can work to define every single little detail - every pixel, every non-functional requirement, every edge case, etc. And even then, the deliverable will come back broken.

Great teams: Along every link in the chain, the clarity of requirements and the quality of the outcomes improve.

With teams like this, you only have to point in the vague direction of where you want to go, and every pixel, every non-functional requirement, every edge case, etc., is handled even better than you could have imagined.

Why?

Partly because of competence.

Partly because of mindset.

In great teams, each person isn't just passing along a message. They don't believe their job is just to "pass the info along."

Instead, each person is a skilled craftsman who believes, "It's my job to polish and refine this using my particular skills and perspective.

This can be the difference between high-quality outcomes, fast. Or low-quality outcomes, slow.

And of course, this is often the difference between success and failure.

AI makes strong product craft more important than ever

AI development is to product development what CGI & CGI Cameras are to directing films.

When you can do "anything," the real question becomes "how do you tastefully make choices that tell a cohesive story?"

In modern cinema, where many shots are entirely CGI, you can place the camera anywhere and move it in any way you like. No limits.

So many mediocre directors misuse this freedom to dramatically move the camera all over the place, failing to give a sense of scale, proportion, motivation, and emotional journey.

Great directors understand that placing and moving the camera takes taste, judgement, and intentionality. They also understand that, often, the best answer is restraint and obeying the laws of physics.

See Pacific Rim 1 vs. Pacific Rim 2.

Great product management is the same.

When engineers can build anything, FAST, the real question (and challenge) becomes WHAT should you build and HOW should it fit into a cohesive product story to drive utility and delight.

In other words: Taste, judgement, and senior product craft become more valuable than ever.

AI can work against shared understanding

The problem with AI-generated analytics that allow anyone to create any insight at any time means that very few people across the business are looking at the same story at the same time.

This is true of AI interfaces and tools across many applications.

Consistency and shared mental models are just as important as AI-powered flexibility in everyone's hands.

Be careful about power undermining shared narratives and mental models.

This is a concern for both operating a business and designing great product experiences.

The Silicon Valley Playbook

This is the Silicon Valley playbook.

1. Sell the dream (Fundraise)​

Raise money on a deck or an early MVP - invest ahead of value, growth, revenue, and profit.

2. Massive Value Creation 

Disrupt the status quo by making something 10-100x cheaper, faster, and/or easier than before. Often, this involves redefining the old rules by using software/internet efficiencies and cutting out incumbent players and processes.

3. Fast-forward to massive scale

Make things standardized and repeatable. Avoid services/high-touch processes. Execute fast and hard to grow really big, really fast. If you have to (and can afford to), subsidize the cost of your product to accelerate adoption.

4. Own the category

Use flywheels (self-reinforcing loops at scale) to build an unbeatable moat with ever-increasing value.

5. Capture a piece of the (massive) newly created value

This is when serious Silicon Valley-style companies seriously start thinking about breakeven (much less profit). Not before.

This is why they win while other players are capital, ambition, and/or execution starved and have small exits or die on the vine.

Tom Hanks knows how to run your startup

I recently watched an interview with Tom Hanks in which he described critical advice he recieved from one of the first directors he ever worked with.

He said actors only need to do three things:

- Show up on time

- Know the material

- Have an idea


It seems to me that this advice applies to high-performance teams and high-performance operators as well.

-- Show up on time

The initial meaning of this may seem obvious: Get to meetings on time, don't keep your colleagues waiting. But it also means having the right discussions at the right time, working on the right things at the right time, and delivering the right features in the right order at the right time. Otherwise, risk trying to boil the ocean and failing to do anything well. Timing is key.

-- Know the material

So many individuals and teams have a culture of showing up to meetings without knowing what the meeting's about, the project's goals, the essential principles, the strategic and tactical arc of the work, etc. It's so common to hear people make suggestions or answer questions that lack many of the essential ingredients of prior discussions and conceptual breakthroughs. Context and clarity of thinking is key.

-- Have an idea

Too many people show up to meetings and sit like wallflowers in the back of the room. Obviously, you don't want everyone clammoring over each other just trying to outdo each other. But you do want people to lean in, be engaged, and contribute their best ideas. Engagement is key.


What do you think? Is Tom Hanks' acting advice exactly what operators need to succeed? Any other key bits of advice for great operators and teams?

Do you really know who your competition is?

More than once, I've spoken to startup founders in second and third-tier markets who tell me that they are hesitant to enter the US market because they don't want to compete with Silicon Valley companies.

I always have to remind them that...

1. They are already competing with Silicon Valley companies - they just don't know it yet. Particularly if they're building a tool that is generalizable globally.

2. While those Silicon Valley companies are raising real money and real valuations and playing in a real market with massive upside potential, they are being resource-starved.

3. In any product/category where localization really matters, the Silicon Valley player is just as likely to come into the local market and eat their lunch when they're ready. Think everything from Coinbase to Airbnb.

The risk of competition in the US is completely misunderstood.

In the US, the market is so big that competition is not to be avoided - it's to be embraced. It is GOOD. It allows you to draft behind market makers and grow very big.

The competitive risk of US players is not that they're hard to compete with IN the US. The competitive risk is that those world-class competitors with massive war chests and market momentum will come and take you on in your home turf at their earliest convenience, crushing you because you were playing it small.

Remember...

Scale is the name of the game.

Many categories are "winner takes all" or "winner takes most".

The world is very, very small.

Flywheels are real.

Capital and courage are very real advantages - yes, even in the AI era.

Play with the big boys or risk being forgotten by history.

User = Idiot

When I was about 12 years old, I went to a "computer event" at the local university.

It was a little weekend meetup that was open to the public.

I felt so big and important going to university to hear a lecture.

A presenter went up to the front of the lecture room and said...

"I'm going to tell you a big secret. But you can't tell anyone!"

I was riveted. I couldn't wait to learn about this adult secret in this university lecture hall!

He wrote on the whiteboard...

"User = Idiot"

Everyone started giggling.

He explained that users don't know anything, and you have to guide them gently through your user experience.

He then tried to wipe it off the board before he "got in trouble."

It was a permanent marker. It wouldn't come off.

Everyone burst into laughter.

It's a core memory I have.

He was right.

You need to assume your users don't know anything. You have to assume they need maximum help. You have to gently guide your user through every screen and flow. You need to spend painstaking hours designing and implementing pixel-level details and animations to help gently and subtly guide the user to moments of success and joy.

As Johny Ive says, people can intuitively feel when the creators of a product truly care about you. It's obvious in every design decision.

This is one of the most essential jobs of product management and product design. To care. To sweat the details. To make things worth using. To make things that are USEFUL.

It can take longer than you ever thought necessary.

It can feel completely unnecessary and excessive.

But it is critical to the success of any great product that hopes to scale.

Nothing is easy. Everything is hard.

Repeat after me:

Nothing is easy. Nothing is easy. Nothing is easy.

"Can't we just..."

No... we can't.

Everything you choose to do takes time and effort to do well.

Everything you choose to do is a tradeoff with something else you're NOT doing.

Nothing is easy. Nothing is easy. Nothing is easy.