👋 Welcome to this week’s edition of 5-Bit Fridays. Your weekly roundup of 5 snackable—and actionable—insights from the best-in-tech, bringing you concrete advice on how to build and grow a product.

Happy Friday, friends 🍻

Instead of starting today off with some silly jokes and banter, I’m opting for a serious recommendation.

I recently finished ‘s book, Hidden Genius, and it’s just full of wisdom. Polina writes , which in many ways is similar to our How They Grow deep dives, except focused on people, like the big cheese, Dwayne “The Rock” Johnson. Polina practices what she dubs people-based learning, and after speaking with hundreds of experts across all sorts of domains, she’s distilled the biggest lessons down into a super practical book. And it was a hard book to read, simply, because I kept turning away to write stuff down. My personal favorite quote is this one: “Stop looking at the scoreboard; play the next play.” 

I loved it, and if you read this newsletter, there’s a good shot you will too. Check it out on Amazon below (I have no affiliation or kickback at all).

Okay, let’s get to it.

Here’s what we’ve got this week:

• How to optimize your pricing page

• How to scale a magical experience: Lessons from Airbnb’s Brian Chesky

• When to dig a moat

• Don’t just blindly run after promotions

• How to value your startup equity offer (free startup equity calculator included)

(#1) How to optimize your pricing page

According to Kyle Poyar, the expert on product-led growth and SaaS—your pricing page is the 2nd most important page on your website.

Many people considering your product use it as a go-to resource for learning about a product and deciding whether to try it. If your pricing page is optimized—from the presentation layer to the communication layer, as well as how you actually package your different tiers—this will drive signups and move more people through your top-of-funnel, even if you raise prices.

It’s easy to see why it’s such an important page, because how much does it cost? is always one of the last-touch questions people have while they’re in the consideration phase. So, after they’ve figured out the product solves their problem and they want what you’re selling, pricing becomes an incredibly important surface area responsible for closing the deal.

And on that note, what does Kyle suggest about optimizing it?

• Reinforce your value prop, over and over again: “Prospects are still learning about your product. Help them understand how it solves their pain.”

• Stop worrying about “pricing hacks”: “There are thousands of articles about $9 vs $9.99 or putting the most expensive package on the left vs right. You should focus on the foundation before you get into growth hacking.”

• Don’t overwhelm prospects: “You want to get folks into the product (or on a call with a rep) as quickly as possible and not spending their time reading through 8pt font on the page.”

• Emphasize benefits, not features: “Your product team probably built a detailed matrix on what features go in what tier. Don’t dump that on the pricing page. Tell a story about what the customer can do with the feature.”

• Each plan needs a clear purpose: “Everyone should know who each plan is for, what it does, and how it helps you make money.”

• Put lingering fears to rest: “In their early days — before the brand became what it is today — Slack smartly put buyers’ fears to rest with their “Wall of Love,” a rotating compilation of tweets from their users emphasizing how much they love the product, which shows up right under their pricing. And below that they showcase that they have thousands of happy customers, including world-leading consumer and B2B brands.”

• Nudge users with behavioral psych: Consider things like anchoring (AKA having a more expensive package to make your cheaper “Popular” one look better). For more, read 7 RESEARCH-BACKED STRATEGIES THAT CONVERT.

And as a rule of thumb, Kyle advises keeping the pricing page helpful, rather than sales-y, and keeping things simple while providing prospects with all the necessary information in a value-first way.

To go deeper, read Kyle’s other essay on Your guide to PLG pricing 201

(#2) How to scale a magical experience: Lessons from Airbnb’s Brian Chesky

In an Oldie but a Goldie episode of Reid Hoffman’s podcast, Masters of Scale, Reid chats with Airbnb founder, Brian Chesky, about how he grew Airbnb. Or, more specifically, about how Brian and his team did a bunch of exceptionally user-centric, and hands-on, work to get them to product-market fit in the early days.

Today, with over 150M users and valued at $93B, Brian still attributes a ton of Airbnb’s colossal success to the cliche—doing things that didn’t scale.

So, to save you from listening to the full thing, here are 3 lessons and a standout quote from Brian from each: 💡

Pay passionate attention to your user

Takeaway: You’re unlikely to be sleeping on your user's couch, but the principle holds: get as close as possible to their problem and experience in order to create empathy around pain points, motivations, and areas of friction.

Design an 11-star experience

As you might know, Brian and the team actually worked with Disney to storyboard Airbnb’s magical guest experience. 🪄

Takeaway: It’s worth going through the exercise to brainstorm what the most incredible (yet unrealistic) experience would look like. Then pull yourself back. AKA, shoot for the stars, and you might reach the moon.

Take advantage of the time before you scale

To go deeper into this concept of building a magical product and user experience, continue pulling the thread by reading this post from Airbnb’s design blog: Measuring Magic: How we turned an elusive vision into a functional product

(#3) When to dig a moat

Aah, moats.

We’ve covered these in some flavor at least once per deep dive because every successful company we’ve analyzed has them. If they didn’t, they’d struggle to protect all the value they’ve created for themselves and have venture-backed raiders looting their castles and stealing users away from them.

Moats are their layer of defense.

But, just like actual moats that surround real castles…they don’t just go around digging themselves.

And while we’ve spoken a lot about what they are in a startup context and how they work to protect a business's wealth, we’ve never really asked the question…when should you start digging one?

Luckily for us, from Not Boring recently did in his aptly titled essay, When to Dig a Moat:

I love how Packy hits the nail on the head here: moats won’t get you product-market fit, but as soon as you have PMF and have proven you’re doing something that (1) works and (2) is valuable, you should be able to protect it from the erosive forces of competition. This moat digging could start at the point where eventual success is obvious to you but to very few others. As he says: “The ultimate goal of a venture-backed startup is to go public or get acquired for roughly $1 billion or more, not to get marked up by other VCs. That can take a long time, typically seven to ten years. Even if the startup lights a fire before competitors realize what it’s doing, it needs to protect and fan that fire for many years before a successful exit. For companies at which everything is going right, moats can be the difference between IPO and cautionary tale.”

To leave you with a parting thought—because increased uncertainty provides more time to build defensibility, there’s a handy inverse to remember here: the easier it is for you to raise money, the more immediately you need moats.

To dig deeper here, here’s some further reading: 🤓

• Productive Uncertainty

• Product > Strategy > Business Model

Thank you for reading How They Grow. This post is public so feel free to share it.

(#4) Don’t just blindly run after promotions

This was my favorite post on LinkedIn this week. Short and sweet, but top-shelf career advice by from .

And if you are considering (now, or in the future) joining another company over a potential promotion, you’ll definitely want to read this last one 👇

(#5) How to value your startup equity offer (free startup equity calculator included)

Understanding your base salary in an offer is easy. You know exactly what it’s worth.

Startup equity is a different beast though. Many folks see something like 5,000 units, sign their offers, and just move along. But, do you know how much it’s worth now, what it could be worth, or in what scenarios you’d actually see money in your bank from it?

Many people at startups don’t, despite that often being the biggest asset they have. And often, that’s because offer letters don’t give you all the information you need to calculate how much your shares could be worth.

Just like you wouldn’t invest in artwork or real estate without (hopefully) at least a basic understanding of how those assets work, you really want to make sure you understand the basics of equity (like what vesting, cliffs, and strike price mean) so you can evaluate your equity offer.

As Jenna Lee for Carta (the authority on startup equity) advises, before taking the job, make sure you ask these three important equity questions so you can do some key calculations:

1. What percentage of the company’s equity am I getting? Make sure the company includes all outstanding shares (including preferred stock, restricted stock, etc.) when calculating this percentage—not just what’s left in the option pool

2. How do you decide how many options each employee gets? Make sure the company has an established method for figuring out how many options to offer instead of coming up with a number willy-nilly. Bonus points if they continually reevaluate their process to make sure it’s fair

3. Do you offer employee liquidity and/or refresh grants? In other words, will you be able to sell shares before an exit like an IPO? If the company intends to remain private for a while, ask if they will hold tender offers (opportunities for shareholders to sell shares of equity). Note: approach this topic delicately. You don’t want to come across as money-hungry, but it’s fair to want to know whether your shares will actually amount to anything.

Use this free startup equity calculator 🧮

If you have equity already and are unsure what it’s worth-or for the next time you get an offer—open up this free calculator Carta put together to understand the offer better.

Note: To use it, you’ll need to know:

• Last preferred price (the last price per share for preferred stock)

• The strike price (the price per share to exercise your options)

• Post-money valuation (the company’s valuation after the last round of funding)

• Hypothetical exit value (the value the company could exit at). You can just play around with different scenarios.

• Number of options in your grant (the total number of options offered to you)

Whatever’s not in your offer letter, just ask the company (besides hypothetical exit value).

🌱 And now, byte on this if you have time 🧠

Back in the day, the grandfather of AI, Alan Turing, invented The Turing Test to help us establish if an AI could match the wits of a human. But you don’t need me to tell you how much has changed since then. We have new types of AIs capable of very different things.

And for that reason, it seems obvious that we need different types of tests. But, I’d never really thought about it much before I read this post. 👇

Read: Beyond the Turing and Into a New Age of AI Assessment

And that’s a wrap, folks. 🫡

If you learned something new, or just enjoyed the read, the best way to support this newsletter is to give this post a like, share, or a restack. It helps other folks on Substack discover my writing.

Or, if you’re a writer on Substack, enjoy my work, and think your own audience would find value in my various series (How They Grow, Why They Died, 5-Bit Fridays, The HTG Show), I’d love it if you would consider adding HTG to your recommendations. 

I hope you all have a wonderful weekend, and I’ll see you on Wednesday for our next deep dive…👀

Until then.— Jaryd✌️

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