🌱 5-Bit Fridays: The time-boxed startup, the #1 skill execs need, compelling business cases, why reason fails, and how Google compromised their product
🌱 5-Bit Fridays: The time-boxed startup, the #1 skill execs need, compelling business cases, why reason fails, and how Google compromised their product
#58
👋 Welcome to this week’s edition of 5-Bit Fridays. Your weekly roundup of 5 snackable—and actionable—summaries from the best operators and experts, bringing you concrete advice on how to build and grow a product.
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Happy Friday, everyone!
In case you missed it this week:
TikTok is on the chopping block again. Lawmakers once again are pushing to ban the app—and the White House has signaled it thinks it’s a good idea. TikTok has responded by sending messages to some users that urge them to help it stop a shutdown.
Bitcoin is replacing gold in investor portfolios.
Ray Dalio went to a Taylor Swift concert, took a selfie, and endorsed her for president. Here here! If I could vote in the US, she’d have mine.
X launches Articles, allowing for long-form text-based content (100K character posts). In short, when considering their recent push into video, their strategy is clear: become the platform for all types of creators.
Adobe has revealed an experimental new AI audio tool that can create music and other audio from text prompts.
Today at a glance:
The Time-Boxed Startup
The #1 question every business case should answer
The #1 skill every executive should have
How Google Blew Up Its Open Culture and Compromised Its Product
Why Reason Fails
+ Quote, chart, recommendation, and extra reads of the week
If you enjoy this weeks curation, consider forwarding it to a friend. ❤️
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(#1) The Time-Boxed Startup
How long should you work on a startup?
has an answer.Key quote
How long is the “time” in “time-boxed?” The short answer is 2 years.
Here's the fine print: Time-box your startup to 2 years in the market. Put your product in customers' hands and try to crack product-market fit. If you add in pre-launch and wind-down time, the total time could be closer to 2.5 or 3 years.
It’s reasonable for duration to vary in particular based on sector and product type. Consider a software-first startup in a mature, low-regulation industry. This versus a hardware startup in a nascent, highly-regulated industry. The 2-year duration leans toward the former: software-first startups with a semi-known playbook.
Since there’s no source of truth here, I asked Twitter what it thought too. How long should founders work on a startup before it’s ok to shut it down?
I got close to 100 replies from a group of mostly builders and a few investors. Most of their answers fell into one of the 8 categories below.
It’s ok to quit …
when you lose your energy or conviction
when you’ve tested your hypotheses
when you’re about 18-36 months in
when the market tells you to
when the money runs out
when you’re at peace
when life calls
never.
In reality, most decisions to shut down involve more than one of these reasons.
— Anu, via
Insight
Timeboxing is a great technique—also just for general productivity—to make sure you don’t spend too much (or too little) time on a startup idea.
Basically, before you start you set and agree to a start and end date. This gives you, say, 6 months of time runway. And within those 6 months, you do everything you can to reach a certain minimum criteria for success.
Therefore you must know what it will take for you to keep going beyond the first off ramp.
At the end, if you feel enough of a pull from the market, your energy is still high, and you’ve made enough forward progress, then you invest more time. If not, you stop.
Note: In the end, it's a judgment call for you and the team to make. It's a philosophy, not a contract.
And why the suggested 2 years?
In most cases, that’s enough time to reach PMF
2 years is enough time to build and test your hypotheses (more than once)
It’s enough time to breath, but not too much that you reduce the urgency to move fast
Your energy as a founder will be the highest in the beginning
One thing you can do with this 🛠️
In startups and life in general, it might be a good idea to quit things a lot sooner that people tend to think.
Working hard and giving something everything is important, but not forever and without limits.
So, go forth and normalize time-boxing startups, while still giving it your all when you’re in it.
Read the full post by Anu
(#2) The #1 question every business case should answer
When you frame your recommendation or idea in a way that gets heard, you increase the chances it gets adopted.
has some advice for how.Key quote
While your circumstances may be unique, the underlying question driving all business cases is the same: How will this save money or make money?
Businesses exist to make money by creating value for customers. The closer you are to generating revenue for your organization, the more leverage you have. Addressing this can be the difference between your idea being labeled as tactical vs strategic.
If you play out the logic behind your recommendation, it’s very likely that your idea already makes or saves the company money. That’s great news. But you have to make this connection explicit. Ideally, you can quantify the impact, but even if you can’t, try to make the connection as concrete as possible.
—Wes Kao, via
Insight
We’re constantly pitching ideas at work to some degree. It could over a call, in a 1-pager, a strategy memo, or just a quick Slack.
The bigger the project, the more you may need to make a strong business case. But the underlying premise is the same: explain why the problem matters, and position why it matters in the form of making or saving money.
This goes without saying, but that’s not the only thing your pitch should cover. It’s just a key kernel that you need to get buying from the top.
One thing you can do with this 🛠️
The next time you’re pitching some recommendation at work, consider hitting one or more of these notes: 🫰
How does this make our customer’s life better? (This usually translates to $ in the end)
How will this drive the business? AKA, make that money.
How much is this costing the business? (See 24 examples)
What’s the frequency and magnitude of this problem?
What bad things happen if we don’t do this? What good things happen if we do?
Why now?
Here are 2 examples by Wes:
Flagging a problem you believe is worth addressing:
🚫 Lazy thinking: “Hey boss, x is a problem. [silence]”
✅ Rigorous thinking: "Hey boss, x is a problem because [why this is a problem and what it’s costing the company]. I’m not 100% sure what to do yet, but my initial hunch is we should do ____ because [your logic and rationale].”
Proposing an idea you believe is worth pursuing:
🚫 Lazy thinking: “Hey boss, can we do [random idea]?”
✅ Rigorous thinking: "Hey boss, given our goal of ___, I recommend we do [this idea] because [insight about the market, customers, category]. It's likely to work and is worth the time/budget because ___. The potential risks and reasons not to do this are ___. But we can minimize the risk with a small experiment by doing ___.”
Read the full post by Wes
(#3) The #1 skill every executive should have
In short, working “high” gets you promoted, and working “low” keeps you from getting laid off. The combination is your new superpower.
What does that even mean though?
unpack it for us.Key quote
I’ve promoted a lot of executives, worked with a lot of executives, and – yes – fired a lot of executives. I always appreciate executives that can get the job done from quarter to quarter, but I love executives that can work high-low. These are the people that I want to work with again and again – because they can find leverage in their work that pays off for the business a year or more later.
Working high-low means you’re able to think and produce across multiple time horizons. You’re balancing initiatives to grow the business over 2 years, hit your plan in six months, and deliver on the most important tasks of the week.
Most near-VPs envision a role where they can just work “high” (think big, set strategy, tell others what to do, etc.). It doesn’t work like that. Without going high, you’ll never get to the leadership team – but without staying low, you’ll be the first laid off because you cost too much.
—
Insight
To work high, you need to:
Have a POV about the future (of your product, team, market, company)
Get high leverage work started that won’t pay off for a year or more
Ask “why?” a lot
Make big bets around long term growth levers, and be okay with the risk
To work low, you need to:
Know your progress against key metrics (monthly revenue, NPS, etc.) and adapt quickly to meet them
Know enough about your team’s work that you can, and do, jump in to help
Kickstart projects yourself when needed (write the brief, scope out V1, etc.)
Know what good (and bad) work is when you see it
The sweet spot is doing both types of work at the same time.
One thing you can do with this 🛠️
As an executive, you don’t want to just be a big thinker that has no output and day to day focus. And you also don’t want to be doer who can’t think about and prioritize bigger bets.
The big skill is fluctuating between high and low work. This means context switching, and often on the fly in the exact same conversation.
If you think you are spending too much time doing low work, for example, one thing you can do is this:
Set aside 30 min each week and write down the challenges you see at your team, company, and industry levels
Then, in a 1:1 with your manager, carve out time to chat about one of these longer-term challenges.
It’s just about making the space to do each type of work and putting in the practice. Once you do that, eventually sliding between high and low work will become natural.
Read the full post by Greg and Taylor
(#4) How Google Blew Up Its Open Culture and Compromised Its Product
David Kiferbaum held various roles within Google from 2015 to 2023. In a recent post with
, he shared an inside look at Google’s open culture’s demise, and the impact it’s had on the product.Key quote
Google used to be a place to ask questions. “You must make it safe to ask the tough questions and to tell the truth at all times, even when the truth hurts,” wrote Eric Schmidt and Jonathan Rosenberg in their 2014 book How Google Works. “When you learn of something going off the rails, and the news is delivered in a timely, forthright fashion, this means — in its own, screwed-up way — that the process is working.”
Inside Google today, the process is not working. Previously accessible Google executives have disappeared, once acceptable questions can’t be asked, and a dispassionate arrogance has taken hold. Unsurprisingly, the company’s deficient culture is showing up in the product, most vividly in its recent Gemini debacle. As a user and shareholder, I’m concerned.
….[The] shift began in 2017 when Google engineer James Damore circulated a memo titled “Google’s Ideological Echo Chamber.” His controversial memo questioning Google's diversity practices noted that "Google’s political bias has equated the freedom from offense with psychological safety, but shaming into silence is the antithesis of psychological safety.” Damore zeroed in on “psychological safety,” a concept that Google had validated through research, and made sacrosanct to management, as critical to the effectiveness of teams.
—
Insight
The shift in the openness culture at Google is underpinned by this premise: the freedom to speak up about anything and everything is gone.
The open town halls where real questions could be asked, and high quality answers were given, has fallen way to often shallow and evasive “corp speak” responses.
Simply, a lot is now not being said. And this can, as as David says, IS, leading to derailment and less accountability at Google.
And the mass layoffs of last year have just perpetuated this culture of more silence.
The closing of Google’s open culture harmed the product. Perhaps a more empowered and vocal Google employee base would have pushed for its nascent large language models to be incorporated within the languishing Google Assistant, or have stood up and flagged the uncomfortable flaws in Gemini’s image generation. Instead, Google’s AI strategy looks unmoored.
— David
One thing you can do with this 🛠️
People on a team must feel empowered to ask hard questions, and feel the psychological safety to do so. If you know that pointing something out will put you on the chopping block, then either you’re going to leave the company or just shut up and collect a paycheck.
Both of those are terrible outcomes for the person who feel they can’t speak up, which has deep implications on the product and company.
Just look at Boeing. (p.s John Oliver’s segment on Boeing this week was excellent)
So what’s one thing you can do to improve the psychological safety net on your team?
Well, toxicity usually starts to breed when managers stop having quality conversations with their team members. So if you are a manager, the next time you’re chatting to someone reporting to you, consider how you can make them feel more seen, heard, appreciated, and invested in.
Psychological safety also erodes when people feel like the culture fixates on “perfect.” And research shows that perfectionist leaders tend to immediately react to mistakes, distrust employees who don’t display their perceived standard of excellence, and often micromanage. To build trust, let go of your perfectionism and let your team learn and grow on their own.
Read the full post by David
(#5) Why Reason Fails
Why do so many people not believe in climate change, the Big Bang, evolution, a round Earth, and vaccine effectiveness? These are 100% true, backed by copious scientific evidence. It’s 2024, and baffling there are folks out there who deny it.
Well, because reason can fail us. In an interesting essay,
gets into what our understanding of reason is, why it's wrong, and why reason really exists.Key quote
Reason, the power to think, understand, and form judgements logically is seen as typically human. It has led to incredible progress in knowledge in sciences that have allowed the human race to achieve control and mastery over the earth and its local surroundings.
However, this notion of humans as beings primarily characterised by access to reason is somewhat at odds with several realities. Beliefs that starkly conflict with the best available evidence are common. Even in affluent countries, teeming with technologies born from scientific understanding, faith in science is not invariably strong.
This discrepancy stems from a misconception. We are inclined to believe that reason emerged as a way to find what is right, to find the truth. From this perspective, there appears to be a direct link from discovering tool use to ultimately unravelling the laws of the universe and venturing into space. Yet, in actuality, reason likely did not evolve to help us be right, but to convince others that we are.
— Lionel Page, via
Insight
We know that reason often leads us to make epistemic distortions and poor decisions. AKA, reason often fails us.
But if we reframe reason from being a tool to help navigate the truth and get around, to a tool that helps us persuade others to follow us around, then the criteria for reason failure changes.
Simply, reason may not exist to help us to have the right beliefs, but instead, to help us play the the game of social communication.
Our ancestors were not selected for their ability to understand the laws of Nature behind the motion of planets, but to convince others to cooperate with them, to trust them, and to be trustworthy themselves. This persuasive skill was crucial for our predecessors' success. Conversely, the ability to critically evaluate others' persuasions—spotting inconsistencies or flawed evidence—is also a vital skill that Mercier and Sperber term epistemic vigilance.
— Lionel
And because we know that those that come out on top in the real world are not the folks who have the most accurate belief, but the people who have less knowledge and better social skills, then evolution is likely selecting us to not think as scientists, but to think as lawyers. Scientists may be more rigorous, but lawyers are those best at convincing others.
That’s what reason now is: our ability to socialize.
One thing you can do with this 🛠️
There will be a time when you have an idea at work that you know is the right move. You have the data to back it up, and you’ve rationalized it as a money maker or saver. But, you’re hitting a wall to get approval.
So far, reason in the traditional sense is failing you.
But when you flip the script and consider it as a social tool, consider why that person (probably your manager) has resistance. For example, imagine you’re suggesting redoing a key feature to your boss, but they keep saying no and perhaps getting defensive and pushing you for undue evidence. Maybe, they built that feature, are emotionally attached to it, and whether they know it or not feel like your proposal is undermining their work.
It can happen, we’re all human.
So, consider how you can use “reason” to persuade them. Maybe that means acknowledging all the strengths of the feature, and telling a story of how that feature did it’s job so well, that it’s now outgrown itself.
Find the social friction—not the truth friction—and you’ll almost always come out on top.
Read the full post by Lionel
And with our main 5 bits for the week done...
1. Quote of the week 💡
Simplicity is not the absence of clutter, that's a consequence of simplicity. Simplicity is somehow essentially describing the purpose and place of an object and product. The absence of clutter is just a clutter-free product. That's not simple.
— Jonathan Ive (Chief Design Officer, Apple)
2. Chart of the week 📈
Netflix is winning the streaming churn wars. Despite roughly doubling its churn rate over the past 5 years, it's proven remarkably resilient with churn rates of 2%, well below the industry average of ~5%. How long will its competitors realistically survive?
- via
3. My recommendation of the week ❤️
Hands down the newsletter I learn the most about the world from from each week.
4. Question for you of the week 🤔
What’s one company/startup you’d absolutely love to see a deep dive on? Could be a success story, or a failure. Let me know in the comments, or just by replying to this email.
5. And now, byte on one of these posts 🧠
Can You Solve Loneliness? These Startups Are Betting On It. via WSJ
The Best Way to Drive Demand in Marketplaces is Hiding in Plain Sight, by
andNo, you don't owe me a favor, by
Everyone's Writing Sounds the Same Now, by
Why Smart People Believe Stupid Things, by
And that’s everything for this week, folks!
If you learned anything new, the best way to support me and this newsletter is to give this post a like and share to help more folks discover HTG. Or, if you really want to go the extra mile, I’d be incredibly grateful if you considered upgrading to paid.
Until next time.
— Jaryd ✌️
...finally found an article imploring me to work high...i feel vindicated and seen (and ready to get low low low)...great compendium as always Jaryd...i worked at a tech company with an open culture that laid off a team of local engineers and then immediately went closed...culture was trashed and the company was never the same but it did succeed many folds in spite of itself (never to the scale of a google)...it takes leadership bravery to be open to a company of people and sadly I feel most who lead in tech/ai.i spaces are incapable of being open...one can dream though...
Thanks for the link Jaryd!