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🌱 5-Bit Fridays: AI is doubting itself, finding a breakthrough idea, reaching your first $1M in ARR, strategy mistakes to avoid, and how to build with velocity.
👋 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.
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Happy Friday, friends 🍻
You might have noticed that this weeks deep dive didn’t come out on Wednesday. If you’re wondering, this is because I’ve teamed up with another epic writer and we’ve aligned our publishing for this Sunday. Keep your eyes peeled, because it’s probably one of the most actionable deep dives I’ve worked on. 💎
Also, on Tuesday I launched How We Flow! I’ve teamed up with my favorite productivity app—Sukha (or, formerly Centered)—to create an online community where we can work together to kill distraction and procrastination, and have a happier and productive work day. Sukha is like Calm/Headspace for productivity. If you missed my post, definitely check it out.
It’s been awesome seeming some of you already join. Here’s this weeks leaderboard!
Otherwise, onto today’s post!
Here’s what we’ve got this week:
A hot take: Customer support should report to product
10 product strategy mistakes to avoid
How Google taught AI to doubt itself
A growth framework for reaching $1M ARR
Building a breakthrough…the secret of Backcasting
Small ask: 👉 If you enjoy reading this post, feel free to share it with friends! Or feel free to click the ❤️ button on this post so more people can discover it on Substack 🙏
(#1) A hot take: Customer support should report to product
Let’s kick today’s 5-Bit off with a hot take from an episode of Lenny’s Podcast: Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product)
One of my favorite takeaways was how Ramp has their customer support team reporting directly to product. Unheard of right?
At it’s core, for Ramp (the fastest growing SaaS startup of all time) that decision is rooted in three things:
The need for insane velocity;
But, ensuring that high velocity does not compromise the products quality;
And, that every support ticket is a failure of their product.
With customer support being the front liners who hear about customer issues and bugs, Ramp has them reporting straight to the people who are responsible. As Geoff Charles (VP of Product) said in the show:
If the product works perfectly, no one should ever have to contact our support team. And what better way of holding the product team accountable for support other than having support report into product.
Now, not every team will (nor should) run and implement this. But, the way Ramp is thinking about this is super interesting. So, here’s a rundown of how to increase your product velocity without compromising the integrity of the product.
1. Implement Feedback Systems
Voice of Customer Processes: Every negative review should be channeled back to the tech lead, product manager (PM), and designer monthly.
Operational Overhead Reporting: Monitor the percentage of tickets from a product area, normalized by its user count. This metric serves as a contract, ensuring teams maintain a low operational burden and are not shipping net new features if things are too broken.
Direct Bug Assignments: Assign bugs and issues directly to the on-call engineer, ensuring immediate attention and resolution. Ramp tackle bugs as soon as they come in. 👇
2. No Bug Backlog Policy
Address and fix bugs as they surface. This proactive approach makes sure that issues don't pile up and become unmanageable.
For nuanced areas like user experience improvements, track support tickets resulting from customer confusion. If this metric rises, pause new feature releases and address the underlying issues. 👇
3. Support as a Product Metric
View every support ticket as a product failure. As Geoff puts it: If a product functions flawlessly, there should be no need for support.
Hold the product team accountable by integrating support metrics into product evaluations.
4. Rethinking Support
Consider having support report directly to product to champion this culture
Instead of merely resolving tickets, incentivize support teams to reduce ticket numbers over time.
This approach requires hiring a different caliber of support personnel, who can later transition into organizational leaders.
By starting from first principles rather than industry benchmarks, it’s possible to hit impressive metrics. As in Ramp’s case, managing over 400,000 users with a support team of fewer than 30 agents.
To listen to the full show (it’s great), go here.
Join 9K+ people learning about product, growth, strategy, and startups.
(#2) 10 product strategy mistakes to avoid
We talk about strategy a lot here. And we should—strategy is the plan that allows startups to win. It’s the foundation of product management, and where true PM and managerial leverage comes from.
As Gagan Biyani (founder of Maven, Udemy, and Sprig) wrote earlier this week:
Being a 3rd time founder has reduced execution risk, but strategy risk remains the same. This means less stress, but roughly equal risk (since strategy is pretty much everything in the startup game).
Today, let’s talk about 10 mistakes people make when it comes to strategy, as per Roman Pichler:
No Strategy: Operating without a clear product strategy often leads to decisions based on the loudest requests form users or stakeholders with big opinions. This reactive approach can lead you to a "Frankenstein product"— one that lacks coherence, offers a disjointed user experience, and fails to deliver genuine value to customers and the business.
Wrong Level: A common pitfall is focusing the strategy either too broadly (portfolio level) or too narrowly (feature level). For instance, a suite like Microsoft Office benefits from an overarching strategy for the entire suite and distinct strategies for individual tools like PowerPoint. Avoid getting bogged down in feature-specific strategies which can create unnecessary overhead.
Incomplete: An effective strategy paints a clear picture of the product's direction. It should articulate who the users are, their problems, the product's unique value proposition, the tangible benefits for both users and the business, and the standout features that differentiate it from competitors.
Unspecific: Ambiguous strategies (be careful of fluff and buzz words) can lead to misalignment and confusion. For instance, a strategy that targets too broad an audience with many unspecific needs lacks focus. Refining the strategy ensures everyone is on the same page and moving in the right direction. As Roman says, “Carry out just enough research work so you can clearly state the target users and customers, the specific problem the product should solve, the business impact it should achieve, and the three to five features that will give it an advantage over competitor offerings”
Not Evidence-based: Relying solely on intuition, past experiences, or the views of a few stakeholders is super risky. Strategies should be grounded in empirical evidence and validated through iterative, hypothesis-driven approaches. This ensures it's rooted in reality and increases the likelihood of product success.
Disconnected: A strategy in isolation is just a document picking up dust on the proverbial shelf. It should be the guiding force behind product delivery, influencing the product roadmap and backlog. A holistic approach makes sure that strategic decisions are translated into actionable tasks and that insights feed back into strategy evolution.
Fixed: Strategy is fluid—things are always changing. Market dynamics shift. New technologies come out and gain adoption. Your product strategy should be agile and adaptive to the changing landscape. A good practice is having regular reviews, keeping a pulse on the strategy making sure it’s still relevant and effective.
Lack of Buy-in: A strategy is only as good as its execution. Without the buy-in of key stakeholders and the development team, you have again have a dust-gathering document. Don’t work on strategy is isolation—loop the right people into the process, as it builds commitment and ownership.
Lack of Effective Ownership: Temporary ownership by a head of product can work. But long-term success requires the product team to take collective ownership. The product manager, empowered to make final decisions, should ensure the strategy is sound, actionable, and aligned with the company's goals.
Strategy Cult: There's no one-size-fits-all in product strategy, and Roman reminds us that copying templates is risky business. There are common themes and best practices, but at the end of the day it's about choosing the right approach tailored to the product and the company’s unique needs.
To add to Roman’s list, here are 4 others I can think of: ♟️
Over-reliance on Trends: Definitely be aware of market trends, but over indexing on them or just blindly chasing the next big thing an be detrimental. A product strategy should not be built solely on what's trending but should be rooted in genuine user needs and the company's core competencies.
Ignoring the Ecosystem: Products don't exist in isolation. They are part of a broader ecosystem that includes complementary products, services, and platforms. Don’t neglect the competitive landscape—both from a threat and opportunity perspective.
Not Telling A Story: A good strategy should be simple, cohesive, and have a clear narrative around what the plan is and why. Stories make it memorable and help win buy-in.
Overestimating Market Size: Stating the opportunity is a big part of strategy—it’s the reason you’re saying this is the direction you want to go. That being said, it's easy to fall into the trap of assuming that everyone is a potential customer. But, overestimating the market size can lead to unrealistic expectations and wasted resources. It's crucial to have a clear understanding of the actual total and serviceable addressable market and the segment that your product specifically targets.
Question: What other mistakes can you think of? 🤔
(#3) How Google taught AI to doubt itself
We all know one of the biggest problems with ChatGPT: it’s ability to be “confidently wrong”.
Ask it a question, and it could well make up facts from thin air.
In all it’s glory, this makes ChatGPT/chatbots a risky research companion. You have to check things, unless you want to end up like this lawyer who submitted citations generated by ChatGPT — not realizing that every single case was just made up.
This state of affairs explains why I find chatbots mostly useless as research assistants. They’ll tell you anything you want, often within seconds, but in most cases without citing their work. As a result, you wind up spending a lot of time researching their answers to see whether they’re true — often defeating the purpose of using them at all.
Well, Google has just made some epic strides to make chatbots a more trustworthy research co-pilot. Of course, this is just with their Bard.
Since Tuesday (9/19), after Bard answers one of your questions, hitting the Google button will “double check” the information Bard is giving you. Here’s how Google explains it:
When you click on the “G” icon, Bard will read the response and evaluate whether there is content across the web to substantiate it. When a statement can be evaluated, you can click the highlighted phrases and learn more about supporting or contradicting information found by Search.
Double-checking a query will turn sentences within the response either green or brown.
✅ Green-highlighted responses are linked to cited web pages. If you hover over one, Bard will show you the source of the information. Green is good.
💩 Brown-highlighted responses indicate that Bard doesn’t know where the information came from, highlighting a likely mistake. Brown is…
This is big stuff. Hopefully, the beginning of the end of AI hallucinations. 🙏
For more top-shelf tech news and reporting, followfrom .
(#4) A growth framework for reaching $1M ARR
Reaching $1,000,000 in revenue is a big deal.
With anything, there is never a silver bullet that will get you there. However, startup scaling veteran Jonathan Martinez does have a tried-and-true growth framework to help get you there.
TL;DR: The main ingredients he shared in this TechCrunch article are:
Finding product market fit (PMF)
Identifying your ideal customer profiles (ICP)
Nailing down messaging for that ICP
Pushing those users to their “aha moment”
Optimizing down funnel metrics (and not getting caught up funnel for too long)
Here’s a rundown of Jonathan’s playbook:
Finding Product-Market Fit (PMF)
PMF = a product has clear pull from the market, signaling organic and sustainable demand.
One way to test this is through paid acquisition channels like Meta or Google. The goal: get people you believe need your product discovering your value proposition ASAP.
Monitor your initial cost per leads (CPL) to gauge interest and potential PMF.
Are folks looking to learn more?
Are they expressing excitement?
From here, get genuine feedback, avoiding biased opinions from close acquaintances. Your goal isn’t to sell people, it’s to learn from them.
Identifying Your Ideal Customer Profile (ICP)
Recognizing your ICP early reduces acquisition costs and churn because you’re going after the right people who need what you’re putting down.
How do you do that? You:
Understand your customers through targeted questions.
Focus on top-performing customers (based on retention and purchases)
Tailor acquisition strategies based on these high-performing customer criteria.
Once you have your ICP identified, next you nail down the messaging that will be used across all of your marketing collateral.
Crafting Effective Messaging
Messaging is the core of every growth medium.
To find your message, identify they key pain points your product addresses and what customers love about your offerings.
Use AB testing tools for rapid messaging tests.
Discovering Your "Aha Moment"
This moment represents when users see the real value in your product.
How do you find it? You analyze user data to identify features or attributes leading to retention. Ask:
Which users are retaining and why?
Which users are churning and why?
What are the common denominators for both groups?
Optimizing Down-Funnel Metrics
Everything toward scaling to your first million leads to optimizing to acquire more, such as your most valuable set of customers
You want to shift focus from upper-funnel metrics like CPL to more substantial metrics like lifetime value (LTV). Focusing too much up funnel leaves you open to churn.
Continuously refine the attributes of your ICP as you learn more to attract higher LTV clients.
There’s no specific time when a startup should begin monitoring more down-funnel metrics, but a great gauge is if you have high churn.
Again, there’s no magic glove here, but at minimum following this framework will help you learn quicker while helping you avoiding common startup pitfalls.
(#5) Building a breakthrough…the secret of Backcasting
How do you build a breakthrough? Or at least, shoot for an idea in that direction? 🌝
Mike Maples, Jr. suggests leveraging what he calls Backcasting.
The idea is simple: The future doesn’t just happen. Builders make the future. We don’t hope for it or stumble upon it—it’s a series of decisions. Steve Jobs didn’t “discover” a market need for smartphones: Being the marketing and creative genius he was, he designed the category and taught us how to think about it.
The premise of Backcasting is getting us out of the present. Mike puts is beautifully: “Breakthrough builders are visitors from the future, telling us what’s coming.”
Folks like this seem crazy in the present but they are often right about the future. That’s why they get called crazy. Maybe the contrarians are just the ones looking way ahead.
Legendary builders, therefore, must stand in the future and pull the present from the current reality to the future of their design. People living in the present usually dislike breakthrough ideas when they first hear about them. They have no context for what will be radically different in the future. So an important additional job of the builder is to persuade early like-minded people to join a new movement.
— Mike Maples, Jr.
Okay, so getting out of the present and projecting yourself into the future is the first step to finding a breakthrough. A great example of a leader who does this over and over again is Jensen from Nvidia (read How Nvidia Grows).
The key with this mental model is not to forecast.
Forecasters typically consider incremental changes to existing products and markets. Forecasting also takes present problems into the future with us. Perhaps most importantly, forecasting assumes the world is mostly the same in the future and that we should operate within the rules rather than think of ways to change the rules.
Backcasting works the other way. Instead of incrementally different, you get exponentially different. With this framework, you may well find that current assumptions about products and markets won’t be true in the future. Your goal is to find insights about the future that are non-consensus and right.
Sounds all well and good. But how do you action that and join the crazy club? 🔮
1. Identify Inflection Points 📈
Inflection points are significant shifts or changes that can lead to exponential growth or breakthroughs.
There are 4 big types:
Technology Inflections: Improvements in tech, like the increased accuracy of GPS, or the development of LLMs.
Adoption Inflections: Rapid changes in the adoption rate of a particular technology, like AI.
Regulatory Inflections: Changes in regulations that create new opportunities.
Belief Inflections: Shifts in long-held beliefs that open up new possibilities.
Key Takeaway: ✨ Start by identifying inflections rather than analyzing current markets. Finding inflections is how a builder finds opportunities that can have an exponential impact.
2. Backcast from Potential Futures 👀 🔙
Backcasting involves envisioning a range of potential futures (from the crazy to the likely) and working backwards to determine the steps needed to achieve them. AKA, if you think this will be the state of 2050, what needs to take place for that to be true?
Types of Futures:
Plausible Futures: Unexpected yet logical scenarios. E.g., the need for unified identity across cloud products.
Possible Futures: Scenarios that stem from personal obsessions or hobbies that lead to unexpected breakthroughs. E.g., the creation of the Mosaic browser by Marc Andreessen.
Preposterous Futures: Seemingly impossible scenarios that challenge conventional thinking. E.g., Elon Musk's vision for electric cars and space exploration.
Key Takeaway: ✨ Expand your thinking to consider a broader range of potential futures, moving beyond traditional forecasting. Backcasting from potential futures widens the range of possible futures you can consider.
3. Gather Breakthrough Insights 💎
Armed with your inflections and a range of potential futures, the next step is to gather insights— the deep understandings or realizations that can lead to innovative solutions.
Finding breakthrough insights requires asking the right questions to the right people.
Go and speak with "Seers," the folks who have a forward-thinking perspective on a given inflection.
Differentiate between insights and analysis. Insights are surprising and exponential, while analysis is based on existing facts.
Ask thought-provoking questions to uncover potential insights, such as challenging assumptions about the future or exploring both best and worst outcomes. E.g
What assumptions about the future might be wrong?
What could happen with this inflection that is more likely than most believe?
What is less likely to happen than many believe?
What is a preposterous potential future that might not be so crazy after all?
What would be the best outcomes from this inflection that could realistically happen?
What would be the worst outcome?
Key Takeaway: ✨ Collect multiple insights and evaluate them in relation to your passion, risk tolerance, and capabilities. Consider the type of team needed to bring each insight to fruition.
I’ll leave you with this quote from Mike:
Ultimately, an Insight is like a “bet.”
You are betting on your insight and you are betting on yourself to be the creator of a future you want. An insight about the future that is non-consensus and right, powered by inflections, and driven by someone “crazy enough” to make it happen….this is the Archimedes lever for building a breakthrough product that moves the world.
🌱 And now, byte on this 🧠
Earlier this weekfrom sat down with Airbnb CEO Brian Chesky.
In their conversation, Brian talks about the role of a leader inside a successful company, and how engaged they should be with customers and day to day decisions.
He also talks about how Airbnb reimagined their product management role and how he’s decided to go way deeper into the details than your typical big company CEO.
Today, Brian sits at the center of the company’s product decisions.
It’s an hour, but it’s a great listen.
And that’s everything for this week guys.
Thanks a lot for reading, and I hope you all have a wonderful weekend!
If you learned anything new, the best way to support this newsletter is to give this post a like or share. It helps other folks on Substack discover my writing, and gives me 🔋.
Until next time.