Progress is slow, but steady if you keep at it.

Most people overestimate what they can do in one year and underestimate what they can do in ten years.

My favorite quote by Bill Gates.

Today is the biggest day of the year for Apple software. It’s called #WWDC and they are about to lay out all the updates. I have some thoughts on how they handle the AI story.

Apple had a great brand for “Intelligence” that they’ve let flounder a bit. GENIUS.

Remember “Genius Playlists”? They were an early version of machine learning and was described this way:

“You can use Genius to have iTunes play songs from your library that sound great together. “

I wouldn’t be surprise if they just use Siri for the brand, but I could also see them using “Genius” to inject into different areas of the products.

I have a lot of thoughts on exactly HOW they’ll integrate LLMs practically for helping a user navigate their day faster. But I wonder that you think? What are we going to hear?


Change in the world of AI

Hey there. I want to share some thoughts I’ve had this week on change. These are based on things I’m seeing in the market and how quickly the world is changing due to AI.

You can view the video below.

I actually used a tool to help me summarize the thoughts I share in this video for your notes as well below.

Recent Events

OpenAI Event

  • OpenAI had an event showcasing their updated ChatGPT model.
  • They demonstrated live demos and took questions from the audience.
  • The event was not highly produced but felt very tangible and immediate.
  • Some features are not yet live to the public but were demoed live.

Google I/O

  • Google discussed future updates to their AI and large language models.
  • The keynote was more about forecasting and imagining future possibilities.
  • The contrast between the two events was stark; OpenAI felt more immediate and actionable.

Key Takeaways

Tangibility of OpenAI vs. Google’s Forecasting

  • OpenAI’s event felt more tangible and actionable.
  • Google’s keynote was more about future possibilities and less about immediate changes.

Implications for Business Models

  • Google’s upcoming changes to search results will impact business models significantly.
  • AI-generated content will be more prominent at the top of search results.
  • This shift will affect businesses that rely on Google for traffic.

Need for Change

  • Businesses will need to adapt to the new search dynamics.
  • Building direct relationships with the audience will become crucial.
  • It’s not just about collecting emails but delivering real value and building a positive brand image.

Challenges Ahead

  • Websites that rely on traffic from Google will face challenges.
  • Direct relationships with the audience will be more important than ever.
  • Traditional channels like Google Ads and SEO will still be relevant but will require new strategies.

Personal Reflection

  • These changes have me thinking about how I need to adapt my work, products, and personal projects.
  • It’s important to stay ahead of these changes and think about new approaches.

Final Thoughts

  • Change is coming, and it’s essential to be prepared.
  • I’m curious about what others think will change with these new updates and changes to large language models and search results.

I’ve been using this guide on how to make oven bacon for many years. Thank you to Dan Benjamin.


Read more: Bacon Method ➚

We’ve been running some tests to optimize this checkout flow and when we switched to one of them, results tanked. It led to a late night working to switch it back so we could try another revision.

Seemingly small changes have a HUGE effect on a person’s likelihood to convert. But it’s more about their ability to quickly understand things.

So here’s my prompt for you product marketers and copywriters out there is…. One of these screens in the Law Insider checkout flow gets 3x the number of signups compared to the other. Which do you think it is and why?

I saw a debate on LinkedIn over whether or not it’s “dated” for the sales rep dress up for sales calls. Most people who chimed in are sales reps that choose to not dress up and tend to wear hoodies and hats on calls.

I personally keep a collared shirt on a hanger and a hairbrush right by my desk so I can get ready for a customer facing call in 10 seconds if needed.

On days where I have a lot of calls, I stay dressed up with proper shoes. Why shoes? No one will see them in Zoom call, right? Sometimes it’s about feeling the part as much as it is displaying the part.

If you have terrible sound, or a feedback echo, even a three piece suit won’t save you. The experience for the other side is just too painful.

If you aren’t going to dress up, good lighting can still make you look 10x better and more prepared.

In order of importance:

  1. Sound
  2. Lighting
  3. Wardrobe

There’s a real difference in mindset and results between those folks who see Closed Won as the destination vs. those that see it for what it is. A point in time.

Product-led Pipeline?

Incentives matter… and there’s an “incentive paradox” at play when product-led meets sales-led.

When you are doing a great job with product education, have transparent pricing, and make it easy for anyone to get started, you will have inherently less meetings as a percentage of traffic.

If you are measured on short term performance on meeting volume, it can be tempting to start to add friction back into the process.

This is often a mistake. Product-led companies with a sales-led component will often do far better in the long run; as an eays to use, helpful, easy to learn product often attracts more champions, awareness, and funnily enough… demo meetings.

You have to work transparently with other teams and to align on the goals and have the tough conversations with the stakeholders ahad of time so you don’t find yourself scambling and making rash decisions.

When asked for a discount…

The first instinct for some sales reps is to reduce prices to close deals. People aren’t always asking because they can’t afford it.

  • Prospect: Discount?

  • Me: Hey there. Are you looking for a discount on our product? We do offer a team plan with a lower cost per seat.

  • Prospect: Is there a discount code?

  • Me: is the current pricing outside your budget? We think it’s a pretty fair deal.

  • Customer: No just bought it.

Sometimes I step into a sales role to stay close to the customer and what they really want. Which isn’t always as it seems. Asking follow up questions is the only way to get cut through the noise.

In-app Product Nudges Based on Actual Usage

Most feature launches land with a thud… … even the truly valuable ones… and it’s no mystery why. 👇

They are often left to wither without ever being mentioned again. This is due to a lack of commitment from the business as a whole in seeing it through.

But YOU, as a PMM or PM can bake in a higher likelihood of success from the start by making a plan to properly surface the feature in your app to users who are a great fit for.

You can even use this strategy from Google Analytics for retention or feature winback campaigns.

Thinking of adding a passive aggressive “Do Nothing” plan to the pricing page. 🤣 WDYT?

Do Nothing Free Forever. Cancel Anytime.

Perfect for those who would rather do things the old fashioned way and don’t want to accelerate their workflow.

✔️ No productivity or quality gains for your contracts. ✔️ No recurring subscription costs.  ✔️ No passwords to remember. ✔️ No time savings.

Button: [Do Nothing]

What if companies put an equal amount of effort into the 30 days after the sale…

as they do the 30 days before the sale?

Build products and features that get better the more you use them them.

If you have an update or a new feature that people are going to want, sometimes all you have to do is tell them about it.

B2B sometimes gets too wrapped up in launch methodologies and approvals and they forget to do the simple things.

tfw the feature starts to get some legs with customers.


IKEA's Three Customers and Why You Should Care

Anyone in product needs to consider this and how these segments apply to their own customers. B2B, B2C, B2C2B or any other acronym.

“As a 31-year veteran of IKEA%2C Tony Giacona describes three typical Ikea shoppers this way:

“The planned customer”: The people who know what they want and come in with a list.

“The experience couple”: The people who are coming in and want to “be amazed” and touch%2C feel and explore to get inspiration.

“The online customer”: They’ve done their homework but “now they want to spend some time interacting%2C to have some meatballs%2C make sure they want to validate their decision online%2C” where they’ll likely complete the purchase and get things delivered. “

Now apply this to your own business. Is it really that different? Really?

Read more: IKEA opening new small-format stores across U.S. ➚

I bought a domain. Again.

Product Marketing and Sales Enablement at their finest.

The HELP Method for creating product marketing content.

I used to struggle every time I sat down to create a product marketing asset. I needed HELP. Now I use The HELP Method for creating product marketing content.

HELP = Hook, Emotion, Logic, Proof


“Not just anybody.”

Get their attention. Speak to a specific audience here. You have just one shot to get this right, but this is where you can experiment the most.


“Help me if you can, I’m feeling down.”

Show you understand their problems and why they should care. If you’ve been in sales or marketing for any length of time, you know that people choose emotionally and justify their decisions with logic.


“Help me get my feet back on the ground.”

Show how it can solve their problem. Show them how it works in practice with their workflow, systems, and daily habits. Is it easy to use? Automatic? How much work is it?


“I feel so insecure.”

Has this worked for anyone before? People fear a road less travelled. Their jobs are on the line after all. Show that others have seen results.


Use this lens to evaluate and enhance all your product marketing assets.

See something a colleague should read? Tag them in the comments.


I’m no expert, but I do have some product marketing experience and I’ve never seen the “shame customers into buying a product they don’t want” strategy work out so well.