🌱 5-Bit Fridays: Developing finesse, fixing product debt, avoiding roadmap failures, writing-building, and more

#63

👋 Hey, I’m Jaryd and welcome to another edition of 5-Bit Fridays—your weekly roundup of 5 actionable insights, bringing you brief advice before the weekend on how to build and grow a product.

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Haaappy Friday, everyone! 👋

Big welcome to the 278 people who’ve joined us this week, including Serene, Amir, Ivan, and Ben! You’re now part of a 20,563 strong bunch of folks who like to make things.

Today is an all-star edition, featuring some of the best writers and operators in tech. If I was playing fantasy startup, these folks would absolutely be my first few picks on the dream team.

Before getting to it though, a quick personal update.

I know my main deep dives have been a bit fewer of late. Outside of life being a bit more demanding recently with work, moving, and family visiting, (excuses excuses…) honestly the biggest reason I’ve taken my foot off the gas a bit is to help manage burnout.

I care about this newsletter, and all of you, a tremendous amount. I never want to stop this thing because it’s one of the best decisions I’ve made. Like a founder and their startup, I’m always thinking about it even when I’m not directly working on it. As a result, it takes up a lot of mindshare.

I have all the intention of ramping up to full pace again, but I read a great post by writing expert

Russell Nohelty

on managing burnout, and decided to slow down and take a bit longer to write each deep dive for a little just to manage it.

Burnout is cyclical. It doesn’t come because you lose interest, but rather, it comes because you care and put so much in to something that it can become all-consuming. I never plan on stopping this newsletter, I love it. I love this community, and I am so grateful you click my emails and hear me out every week.

And to keep the fire going, sometimes it doesn’t need more logs, it needs to breath a bit.

Actually, I don’t think that’s how to keep a fire going. But the analogy somewhat makes sense here.

Anyway, I’m actively working on the next deep dive and it’s on a super cool company. Stay tuned.

Onto today’s post…

— Jaryd

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ICYMI this week 🗞️

• beehiiv–Substack’s top competitor–just raised $33mm in Series B. I wrote about beehiiv here and made a case for their superiority in a lot of areas as a newsletter platform, and with this funding, they’re going to double down on, among other things, building out their ad network. They were already shipping ridiculously fast, so I expect this fuel to supercharge this. (Take a look ↗️)

• Women don’t have to send the first message anymore on Bumble. Another company we’ve covered here, Bumble has shipped a pretty major redesign which now allows men to make the opening move. That was a pretty big differentiator for them, so time will tell if it was the right move. (Take a look ↗️)

• Shopify’s stock has surged 200% in the 18 months after October 2022. Also a company we’ve covered, Shopify’s stock rebound can be credited to several well-timed decisions. This is something I actually plan to write about in a Shopify Part 2, so stay tuned. (Take a look ↗️)

• Biden has plans to raise taxes. Yes, he’s right that the US needs to raise taxes, BUT—and this is a big but—he’s just wrong/insane in some approaches. The biggest one being taxing unrealized capital gains. That would crush the US startup economy and honestly stifle so much innovation. I doubt this will get close to passing, but just saying. Rather focus on simplifying a ridiculously complicated tax code my guy, and stop quizzing me on my income when you know exactly how much I made. (Take a look ↗️)

• Anthropic, one of OpenAI’s biggest rivals, launched an iPhone app for its chatbot, Claude. I’ve been using the paid Claude Opus model, and I actually prefer the quality of responses to ChatGPT. (Take a look ↗️)

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Today’s 5-Bits ☔

1. Startup Canvas: Product Strategy and a Business Model for a New Product

2. Writer-Builders

3. 3 types of debt product teams need to tackle

4. 7 fails of roadmap-making

5. The unspoken skill of finesse

+ Quote, tools, chart, and rabbit holes of the week

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1️⃣ Startup Canvas: Product Strategy and a Business Model for a New Product

I really enjoyed

Paweł Huryn

‘s take on why common frameworks like the The Business Model Canvas and The Lean Canvas miss the mark around startup product development.

I totally agree with his sentiment—they are great tools that should not be disregarded, but with a few modifications like mixing strategy and business model together, can become much more relevant to startup founders.

Being the ultra-helpful guy Pawel is, he didn’t just write about his thoughts, he created a handy visual and template.

Note, I think Pawel is missing one or two things in his model. I’ve added to it below too.

Key quote

Not quite a quote, but straight to the good stuff…here’s Pawel’s Startup Canvas model. (Double click to expand and read)

Insight & Action 🛠️

What I love about Pawel’s updated model here is how he focuses on a holistic view of strategy and business model, and how they need to work together.

Compared to the other popular canvas frameworks, Pawel has a few key inclusions:

• Vision is front and center. For startups, this is key. It’s the North Star for the team and founders, and the reason why people show up and work for lower wages :)

• There’s a clear “can’t/won’t copy”. Basically, it’s your defensibility. What makes you think your competitors can’t or won’t copy your strategy? Is this unique value proposition, counter positioning, activities, knowledge, culture, partners, IP?

• Trade-offs. As I wrote about last week, a strategy is a way to say no. Just as much as it tells you what you need to do, it helps you stay away from distractions.

• Relative costs. This forces you to think about what you want to optimize for. Do you want to optimize for low cost, like Southwest Airlines, or for unique value, like Starbucks?

All great additions. Personally, I’d add the following to the list of things think about as you build a canvas:

• Inflection & Insight. This is your product’s why now? What inflections/changes are happening from a technical perspective, or a behavioral/demand/societal standpoint. And from here, what is your unique insight? This is key to your strategy.

• Headwinds. These are large risks or obstacles that could be existential. Say you are a startup building within the social landscape; does the TikTok ban expose you? If a headwind is substantial, how will you navigate it? Another big input to strategy.

• Startup timebox. If you’re a founder, you need to ask yourself the tricky question—how long can/will you work on this idea before stopping, or before making a decision to keep at it. Timeboxing is an important tool to make sure you don’t just chip away at a losing bet and burn your most precious resource…your time. For example, “I’ll work at this all out for 10 months. If we have more than 10 paying customers by then, we know we have something and I will continue.”

Of course, every situation is different. I’ve said it before, just copying and pasting a template can be problematic, as the only thing that matters is doing what works best for you and your product/market/team/culture context.

But, Pawel’s Startup Canvas is a great forcing function to sit down and think about hard questions. And at the end of the day, asking the right questions is what will get you building the right product.

What question/theme would you add to the canvas?

Read the full post by Pawel from

The Product Compass

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2️⃣ Writer-Builders

Much like

Anu

, I’ve always enjoyed and gravitated towards writing. When I was in school, the subjects I chose (and did the best in + enjoyed the most) where the ones that leaned essay heavy. History, art, biology, and English. And in University, economics.

Clearly, I’m still at it.

Writing has been one of the best habits I’ve kept up, because quite simply, it’s just made me better at life and work. Why? Because it’s one of the best vessels for learning.

And now, applied to the domain of product/startups/tech that I work everyday in, writing has been a huge advantage. An advantage to both me personally, and an advantage to you (I hope?) as the reader since I bring real-world operational experience to the conversation.

In a recent post, Anu shares a new archetype that really resonated with me, the writer-builder—someone who both writes and builds in a given domain.

These are the Substackers (and friends) like

CJ Gustafson

,

Reid DeRamus

, and

Aakash Gupta

. The writer-builder is in a position to create some of the most insightful content, as well as crush their day job. The examples above prove that.

So, what should you do about it?

Key quote

Writing increases your rate of revelation. This is true irrespective of the subject because writing is a process of reflection, assertion, and iteration. Writing clarifies your own ideas. Writing begets new ideas too. Writing lets you explore ideas in depth even if you won’t have time to act on them all. Writing shows people how you think and lets them decide if they agree, if they respect you, and if maybe you’re the kind of person they’d want to ask out for coffee or spend years working with.

You don’t write something in one shot and hit publish. And you don’t build one version of something and call it done. Doing either well calls for copious amounts of reflection and revision too. So while not everyone has the interest or aptitude to embody the writer-builder archetype, those who do have a distinctive advantage — they can unlock a virtuous cycle of revelation that levels up both.

— Anu, via

Working Theorys

Insight & Action 🛠️

The simplest way to think about being a writer-builder is to build and learn in public.

As you know, the concept of putting your work out into the public is becoming far more encouraged. The companies that operationalizing this (e.g beehiiv, The Browser Company) do a great job at attracting talent, investors, and customers.

You can do the same thing individually, and you should, because building any kind of audience is building distribution—and you always want distribution.

But distribution via writing vs say on Twitter/YouTube etc is extra powerful, because it’s a direct line of communication with people. Also, putting words to “paper” is the best way to figure out what you actually think about something.

As an operator, here’s your next step: Go build something. Write about what you learnt. Apply what you learnt after thinking about it. Go build something better. Repeat.

Your writing doesn’t have to be long either, or particularly consistent. Just write some, share, and write some more.

Platforms like Substack and beehivv are excellent ways to get started.

Here’s one parting nugget of wisdom from Anu’s post.

Building first and then writing is like lighting a match from a lit candle. Writing before you’ve built much can be like trying to start a fire by rubbing two sticks together. Building doesn’t have to come first, but it’s easier if it does.

Write about what you build. Build what you write about. But the quality bar is high. Each needs to stand on its own. Because in this increasingly noisy world, only the best will break through.

Read the full post by Anu

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3️⃣ 3 types of debt product teams need to tackle

We all know about tech debt.

We want to build something, but in pursuit of getting it done either fast or more affordably, we make some tradeoffs for short-term gains with how we build that thing. Like sub-optimal architecture, for example. The outcome usually is less-than-favorable code and infrastructure in the long-term that creates accelerating development friction that eventually compounds and needs to be fixed.

At some point, just like any debt, it must be paid (and with interest). If you don’t, well…big problems.

Anyway, there are other types of less obvious debt that founders and PMs should think about.

Aatir Abdul Rauf

points them out (product and marketing debt), and highlights some neat solutions.

Key quote

When a product starts to accumulate complexity that comes in the way of increased adoption, feature discovery, or understanding of the product, this is usually a sign of product debt.

Some common symptoms:

• confusing information architecture (e.g. cluttered navigation bar)

• outdated product copy

• conflicting features that overlap each other

• data hygiene issues due to a data model update

• edge cases with increasing frequency of occurrence

It’s important to tackle product debt to prevent users from churning due to friction in usage or a reduction in customer satisfaction as the product footprint grows.

— Aatir Abdul Rauf, via

Behind Product Lines

Insight & Action 🛠️

• Tech debt is often seen as an engineering problem. “Engineering made that decision”, or “Engineering needs to get around to fixing it”. But, let’s not play hot potato. Often, tech debt accrues because of poor product management. For example, overlooked edge cases, confusing PRDs, low context communication, and failure to give engineers visibility on the future plans can equally contribute to tech debt as well.

  • What you can do about it: The simplest thing to do is communicate product vision and potential roadmap items to the engineering team. If they understand where a product is going, they can make better decisions today about what will make that possible. Really try understand the tradeoff between getting something released faster, vs better.

• Product debt is the homework assignment you get for being successful. When your product works and you acquire users, you’ll inevitably build more stuff for them. Overtime, certain features will get neglected (even core loops of your product) in pursuit of building the next thing, and eventually, your UI/UX will become more confusing. This is amplified by the fact that most teams struggle to take things away.

  • What you can do about it: Outside of regularly investing in IA (information architecture) updates and UI/UX deep dives, make it a practice to unship. I wrote about that here, but in short—post-release make sure to audit the numbers and create a culture of sunsetting features that are not landing. Related, here’s what I said a few weeks ago:

  Don’t get distracted by shiny new features and lose sight of your core—the most important stuff you already have. Lenny Rachitsky had an 11/10 post on this earlier this week, but simply, as your product matures it becomes increasingly important to not neglect the main JTBD and loop of your product. Your quality bar is high when you’re always thinking about making that loop fast, efficient, and delightful.

Read the full post and learn about Marketing Debt by Aatir

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4️⃣ 7 fails of roadmap-making

In a recent post, PLG G.O.A.T

Leah Tharin

shares common potholes to avoid when creating long term plans.

Key quote

When it comes to roadmaps, the process itself is often more valuable than the end result.

Just going through the ordeal of gathering the relevant stakeholders will reveal misalignment and help everyone to sync up. For instance, if you’re talking through timelines and someone says ‘That will take a year’ and someone else says ‘3 months’… well, you may not know who’s right, but clearly there are some conflicting expectations about how difficult this is to build.

This is a great opportunity to identify the source of the misalignment and get on the same page. Every time you disagree and find a compromise, you learn something. This whole process will make your team and your whole organization better at working together.

— Leah Tharin, via

Leah’s ProducTea

Insight & Action 🛠️

Here are the 7 mistakes Leah reminds us to avoid:

• Too much detail on effort estimations. 99% of the time, project estimates are wrong 100% of the time. When I started as a PM, I over-indexed on this and tried to create these visual gantt roadmaps showing a lovely happy path. One that relied on estimates. These were never right, and I adjusted course to using mostly Now/Next/Later roadmaps. It’s much easier, because getting agreement on ranked priorities is easier than getting folks to agree on time/effort estimates.

• Too much focus on today. It’s easy to get lost in the sauce of what’s happening around you today, thus, having your roadmap too zoomed in on your current operations. A key part of a roadmap isn’t just to show people what they are working on next, but to paint a broader picture of where things are going and how everything comes together in the future.

• Too much focus on the competition. Be wary of roadmaps that are too reactionary. If things are constantly in flux and your plans change regularly because of what other people are doing, again, you risk getting caught up too much in the today. As Leah says, copying competitors is like “the blind leading the blind.” Spot on analogy.

• Too much focus on outputs. The further out that a roadmap looks, the more the work needs to be outcome focused. Outputs are very prescriptive, and they can be built against easily because what to do is super clear. But as you look beyond the horizon, you can’t know what the outputs you want will be. This means long-term projects must be outcomes…like expand into a new vertical, improve retention in a specific market, or unlock some group of on-the-fence customers.

• Too public. As Leah notes, “If you promise to ship something to customers, you can’t choose not to ship it anymore, therefore taking away the possibility of saying, “After looking at the data, maybe this wasn’t a good idea.”. Her advice—just avoid any public facing roadmap that may set unattainable expectations with customers.

• Not actionable enough. In the short-term when outputs are more in focus, a roadmap will fail if it’s too abstract.

• Not properly communicated. What’s the saying? Something like “If a tree falls in the forest and nobody hears or sees it, did the tree even fall?” Well, that is the truth of roadmaps and strategy memos. You can do all the right stuff, but if nobody hears its and gets it, it’s useless. As a founder or PM, the roadmap is you one big thing to evangelize and drill home.

Another two problem I’ve seen on roadmaps worth noting here

1. They are idea lists. A roadmap should not be a laundry list of things people on the team want to do (think a HiPPO’s ideas). Projects must be tied to customer discovery.

2. They are too fixed. A roadmap can’t just be created and then left until the plan is done. Stakeholders need to meet regularly enough in cycles to align on priorities and move things around if needed. Nothing is set in stone, and good roadmaps reflect that.

What’s one mistake you’ve seen around roadmap? Drop any thoughts in the comments.

Read the full post by Leah

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5️⃣ The unspoken skill of finesse

When I hear the word finesse, I’m instantly transported back to 2013. I’m sitting on my couch playing FIFA while I should be studying for my accounting exam tomorrow. My friend Luke has just taught me how to shoot the perfect shot on goals. Hold R1 and press O— shoot towards the far corner.

I’ve just learnt the finesse shot.

Well, as a tradeoff for that lesson, I failed accounting.

So worth it. Who wants to be an accountant anyway. Legal Zoom can do by books for me, but nobody can score banging goals on my behalf, can they?

Finesse is polish, and beyond the screen of FIFA, the more polished you are at work and in your interactions, the higher the likelihood is you’ll: close more deals, get a seat at the table, hire better talent, get buy in, build trust, and get promoted.

In a tactical post,

Wes Kao

unpacks what finesse looks like, why it matters, and how to develop it for yourself and your team.

Key quote

Every leader should actively look for opportunities to teach their team judgment. If you’re not doing this, you’re barely scratching the surface on what “learning on the job” means for your team.

You need to teach them to “see” how you see, and notice what you notice. Explain the “why” behind what you said or did, or the “why” behind your feedback. When someone on the team displays finesse, point it out. Let everyone learn from it.

Over time, your team will improve their ability to pick up on what you pick up on, and eventually, to make the judgment calls you would have made.

I believe doing this, regularly and with gusto, is how you create a culture of high standards and dramatically improve your team’s chances of winning.

— Wes Kao, via

Wes Kao's Newsletter

Insight & Action 🛠️

Finesse is good judgment and succinct sharing of ideas/thoughts, applied to delicate scenarios, usually in the context of communicating with other people.

Sure, some people are naturals and are generally more attuned to picking up cues, nuance, and micro-expressions. That’s a skill that absolutely helps with reading situations and being on-the-fly adaptive.

And I do think there’s a strong correlation between experience in a domain and finesse. The more you get the market and customers, of course you’ll be in a better position to know what to do and say, and what not to.

But like most skills, we can train our finesse muscle.

How?

The next time you’re in a real-world scenario, before speaking or sending some message, pause, and think a bit deeper about the layers of the situation/question. Simple in communication is great, but sometimes, simple oversimplifies something that is more complex.

One tactical thing that can hone your finesse is to apply conditions to what you say. For example, instead of just saying some fact or opinion, follow the arc of:

• If this, then than.

• Or if this, then that.

• I believe it’s Y because of X, therefore, we should do this thing.

A simple tool that forces you to find the layers in any situation. And the more you practice this, the more you’ll shoot bangers in the top right corner.

R1 + O…what a combo

Read the full post with more advice on sharpening your finesse by Wes

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Quote of the week 💡

“Think of the life you have lived until now as over and, as a dead person, see what’s left as a bonus and live it accordingly.”

— Marcus Aurelius

Tools of the week 🛠️

Every week, I highlight 3 products I actually use. Today, I’m highlighting:

• Typeform: If you send surveys and care about the UI/UX respondents see, then Typeform is a no brainer. Beautiful, on-brand, surveys for anything.

• Waking Up: Meditating is a key part of my morning, and I couldn’t suggest doing it in some form enough. I recently switched from Headspace back to Waking Up for more philosophical content. You can get 30 days free to try it out.

• Anthropic AI: I’ve been testing out Anthropic’s version of ChatGPT recently, and while it’s missing some features vs OpenAI, I’ve found the quality of responses better tbh.

👉 View all my recommendations.

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Chart of the week 📈

Good news for folks in the travel industry. With all the extra money floating around the US system, a record number of people are planning international vacation in the next 6 months.

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Byte on one of these posts 🧠

Other favorite reads from the week…

• In a Job Interview, This Is How to Acknowledge Your Weaknesses, by

  Adam Grant

• Why I Don’t Invest in Real Estate, by

  Tomas Pueyo

• The Great Social Media Reset - We Scroll More Than We Post., by

  Uttam Dey
  and
  Amrita Roy

• Tesla In Turmoil: The EV Meltdown In 10 Charts, by

  Robert Bryce

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Whenever you are ready 🤝

Here are 2 ways I can help you:

1. Are you looking to grow your team? If so, I’ve invested in a company (Athyna) that can help you find incredible talent and build out your global team. Their product, service, and talent pool is just amazing. Just reply to this email if curious, or learn more here ↗

2. Are you looking to grow your product by reaching my audience of founders, PMs, and product builders? If so, maybe we can partner up. You can reply to this email to get the convo started, or learn more here ↗

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And that’s everything for this week’s edition.

As always, thanks so much for reading and being part of this growing community. It means a lot. If you enjoyed today’s post, don’t be shy to hit the heart button or forward this email to a friend.

Until next time.
— Jaryd ✌️

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