More on Leadership

Joe Procopio
3 years ago
Provide a product roadmap that can withstand startup velocities
This is how to build a car while driving.
Building a high-growth startup is compared to building a car while it's speeding down the highway.
How to plan without going crazy? Or, without losing team, board, and investor buy-in?
I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.
It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.
Goals matter.
Although they never change, goals are rarely understood.
This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.
A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.
At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.
Big, wealthy companies can do this. It's suicide for a startup.
The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.
It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.
In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.
In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.
Be vague for growth, but direct for execution.
Here's my plan. The real one has more entries and more content in each.
Let's discuss smaller boxes.
Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.
Why do we put everything in a product roadmap like a project plan?
Yes, I know. We use it when the product roadmap isn't goal-based.
A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.
Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.
Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.
No soothsayers. Predicting the future is pointless; just prepare.
A map is useless if you don't know where you're going.
As we speed down the road, the car and the road will change. Goals define the destination.
This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.
When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.

Greg Satell
3 years ago
Focus: The Deadly Strategic Idea You've Never Heard Of (But Definitely Need To Know!
Steve Jobs' initial mission at Apple in 1997 was to destroy. He killed the Newton PDA and Macintosh clones. Apple stopped trying to please everyone under Jobs.
Afterward, there were few highly targeted moves. First, the pink iMac. Modest success. The iPod, iPhone, and iPad made Apple the world's most valuable firm. Each maneuver changed the company's center of gravity and won.
That's the idea behind Schwerpunkt, a German military term meaning "focus." Jobs didn't need to win everywhere, just where it mattered, so he focused Apple's resources on a few key goods. Finding your Schwerpunkt is more important than charts and analysis for excellent strategy.
Comparison of Relative Strength and Relative Weakness
The iPod, Apple's first major hit after Jobs' return, didn't damage Microsoft and the PC, but instead focused Apple's emphasis on a fledgling, fragmented market that generated "sucky" products. Apple couldn't have taken on the computer titans at this stage, yet it beat them.
The move into music players used Apple's particular capabilities, especially its ability to build simple, easy-to-use interfaces. Jobs' charisma and stature, along his understanding of intellectual property rights from Pixar, helped him build up iTunes store, which was a quagmire at the time.
In Good Strategy | Bad Strategy, management researcher Richard Rumelt argues that good strategy uses relative strength to counter relative weakness. To discover your main point, determine your abilities and where to effectively use them.
Steve Jobs did that at Apple. Microsoft and Dell, who controlled the computer sector at the time, couldn't enter the music player business. Both sought to produce iPod competitors but failed. Apple's iPod was nobody else's focus.
Finding The Center of Attention
In a military engagement, leaders decide where to focus their efforts by assessing commanders intent, the situation on the ground, the topography, and the enemy's posture on that terrain. Officers spend their careers learning about schwerpunkt.
Business executives must assess internal strengths including personnel, technology, and information, market context, competitive environment, and external partner ecosystems. Steve Jobs was a master at analyzing forces when he returned to Apple.
He believed Apple could integrate technology and design for the iPod and that the digital music player industry sucked. By analyzing competitors' products, he was convinced he could produce a smash by putting 1000 tunes in my pocket.
The only difficulty was there wasn't the necessary technology. External ecosystems were needed. On a trip to Japan to meet with suppliers, a Toshiba engineer claimed the company had produced a tiny memory drive approximately the size of a silver dollar.
Jobs knew the memory drive was his focus. He wrote a $10 million cheque and acquired exclusive technical rights. For a time, none of his competitors would be able to recreate his iPod with the 1000 songs in my pocket.
How to Enter the OODA Loop
John Boyd invented the OODA loop as a pilot to better his own decision-making. First OBSERVE your surroundings, then ORIENT that information using previous knowledge and experiences. Then you DECIDE and ACT, which changes the circumstance you must observe, orient, decide, and act on.
Steve Jobs used the OODA loop to decide to give Toshiba $10 million for a technology it had no use for. He compared the new information with earlier observations about the digital music market.
Then something much more interesting happened. The iPod was an instant hit, changing competition. Other computer businesses that competed in laptops, desktops, and servers created digital music players. Microsoft's Zune came out in 2006, Dell's Digital Jukebox in 2004. Both flopped.
By then, Apple was poised to unveil the iPhone, which would cause its competitors to Observe, Orient, Decide, and Act. Boyd named this OODA Loop infiltration. They couldn't gain the initiative by constantly reacting to Apple.
Microsoft and Dell were titans back then, but it's hard to recall. Apple went from near bankruptcy to crushing its competition via Schwerpunkt.
Rather than a destination, it is a journey
Trying to win everywhere is a strategic blunder. Win significant fights, not trivial skirmishes. Identifying a focal point to direct resources and efforts is the essence of Schwerpunkt.
When Steve Jobs returned to Apple, PC firms were competing, but he focused on digital music players, and the iPod made Apple a player. He launched the iPhone when his competitors were still reacting. When Steve Jobs said, "One more thing," at the end of a product presentation, he had a new focus.
Schwerpunkt isn't static; it's dynamic. Jobs' ability to observe, refocus, and modify the competitive backdrop allowed Apple to innovate consistently. His strategy was tailored to Apple's capabilities, customers, and ecosystem. Microsoft or Dell, better suited for the enterprise sector, couldn't succeed with a comparable approach.
There is no optimal strategy, only ones suited to a given environment, when relative strength might be used against relative weakness. Discovering the center of gravity where you can break through is more of a journey than a destination; it will become evident after you reach.

Nir Zicherman
3 years ago
The Great Organizational Conundrum
Only two of the following three options can be achieved: consistency, availability, and partition tolerance
Someone told me that growing from 30 to 60 is the biggest adjustment for a team or business.
I remember thinking, That's random. Each company is unique. I've seen teams of all types confront the same issues during development periods. With new enterprises starting every year, we should be better at navigating growing difficulties.
As a team grows, its processes and systems break down, requiring reorganization or declining results. Why always? Why isn't there a perfect scaling model? Why hasn't that been found?
The Three Things Productive Organizations Must Have
Any company should be efficient and productive. Three items are needed:
First, it must verify that no two team members have conflicting information about the roadmap, strategy, or any input that could affect execution. Teamwork is required.
Second, it must ensure that everyone can receive the information they need from everyone else quickly, especially as teams become more specialized (an inevitability in a developing organization). It requires everyone's accessibility.
Third, it must ensure that the organization can operate efficiently even if a piece is unavailable. It's partition-tolerant.
From my experience with the many teams I've been on, invested in, or advised, achieving all three is nearly impossible. Why a perfect organization model cannot exist is clear after analysis.
The CAP Theorem: What is it?
Eric Brewer of Berkeley discovered the CAP Theorem, which argues that a distributed data storage should have three benefits. One can only have two at once.
The three benefits are consistency, availability, and partition tolerance, which implies that even if part of the system is offline, the remainder continues to work.
This notion is usually applied to computer science, but I've realized it's also true for human organizations. In a post-COVID world, many organizations are hiring non-co-located staff as they grow. CAP Theorem is more important than ever. Growing teams sometimes think they can develop ways to bypass this law, dooming themselves to a less-than-optimal team dynamic. They should adopt CAP to maximize productivity.
Path 1: Consistency and availability equal no tolerance for partitions
Let's imagine you want your team to always be in sync (i.e., for someone to be the source of truth for the latest information) and to be able to share information with each other. Only division into domains will do.
Numerous developing organizations do this, especially after the early stage (say, 30 people) when everyone may wear many hats and be aware of all the moving elements. After a certain point, it's tougher to keep generalists aligned than to divide them into specialized tasks.
In a specialized, segmented team, leaders optimize consistency and availability (i.e. every function is up-to-speed on the latest strategy, no one is out of sync, and everyone is able to unblock and inform everyone else).
Partition tolerance suffers. If any component of the organization breaks down (someone goes on vacation, quits, underperforms, or Gmail or Slack goes down), productivity stops. There's no way to give the team stability, availability, and smooth operation during a hiccup.
Path 2: Partition Tolerance and Availability = No Consistency
Some businesses avoid relying too heavily on any one person or sub-team by maximizing availability and partition tolerance (the organization continues to function as a whole even if particular components fail). Only redundancy can do that. Instead of specializing each member, the team spreads expertise so people can work in parallel. I switched from Path 1 to Path 2 because I realized too much reliance on one person is risky.
What happens after redundancy? Unreliable. The more people may run independently and in parallel, the less anyone can be the truth. Lack of alignment or updated information can lead to people executing slightly different strategies. So, resources are squandered on the wrong work.
Path 3: Partition and Consistency "Tolerance" equates to "absence"
The third, least-used path stresses partition tolerance and consistency (meaning answers are always correct and up-to-date). In this organizational style, it's most critical to maintain the system operating and keep everyone aligned. No one is allowed to read anything without an assurance that it's up-to-date (i.e. there’s no availability).
Always short-lived. In my experience, a business that prioritizes quality and scalability over speedy information transmission can get bogged down in heavy processes that hinder production. Large-scale, this is unsustainable.
Accepting CAP
When two puzzle pieces fit, the third won't. I've watched developing teams try to tackle these difficulties, only to find, as their ancestors did, that they can never be entirely solved. Idealized solutions fail in reality, causing lost effort, confusion, and lower production.
As teams develop and change, they should embrace CAP, acknowledge there is a limit to productivity in a scaling business, and choose the best two-out-of-three path.
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Jared Heyman
3 years ago
The survival and demise of Y Combinator startups
I've written a lot about Y Combinator's success, but as any startup founder or investor knows, many startups fail.
Rebel Fund invests in the top 5-10% of new Y Combinator startups each year, so we focus on identifying and supporting the most promising technology startups in our ecosystem. Given the power law dynamic and asymmetric risk/return profile of venture capital, we worry more about our successes than our failures. Since the latter still counts, this essay will focus on the proportion of YC startups that fail.
Since YC's launch in 2005, the figure below shows the percentage of active, inactive, and public/acquired YC startups by batch.
As more startups finish, the blue bars (active) decrease significantly. By 12 years, 88% of startups have closed or exited. Only 7% of startups reach resolution each year.
YC startups by status after 12 years:
Half the startups have failed, over one-third have exited, and the rest are still operating.
In venture investing, it's said that failed investments show up before successful ones. This is true for YC startups, but only in their early years.
Below, we only present resolved companies from the first chart. Some companies fail soon after establishment, but after a few years, the inactive vs. public/acquired ratio stabilizes around 55:45. After a few years, a YC firm is roughly as likely to quit as fail, which is better than I imagined.
I prepared this post because Rebel investors regularly question me about YC startup failure rates and how long it takes for them to exit or shut down.
Early-stage venture investors can overlook it because 100x investments matter more than 0x investments.
YC founders can ignore it because it shouldn't matter if many of their peers succeed or fail ;)

Sanjay Priyadarshi
3 years ago
Meet a Programmer Who Turned Down Microsoft's $10,000,000,000 Acquisition Offer
Failures inspire young developers
Jason citron created many products.
These products flopped.
Microsoft offered $10 billion for one of these products.
He rejected the offer since he was so confident in his success.
Let’s find out how he built a product that is currently valued at $15 billion.
Early in his youth, Jason began learning to code.
Jason's father taught him programming and IT.
His father wanted to help him earn money when he needed it.
Jason created video games and websites in high school.
Jason realized early on that his IT and programming skills could make him money.
Jason's parents misjudged his aptitude for programming.
Jason frequented online programming communities.
He looked for web developers. He created websites for those people.
His parents suspected Jason sold drugs online. When he said he used programming to make money, they were shocked.
They helped him set up a PayPal account.
Florida higher education to study video game creation
Jason never attended an expensive university.
He studied game design in Florida.
“Higher Education is an interesting part of society… When I work with people, the school they went to never comes up… only thing that matters is what can you do…At the end of the day, the beauty of silicon valley is that if you have a great idea and you can bring it to the life, you can convince a total stranger to give you money and join your project… This notion that you have to go to a great school didn’t end up being a thing for me.”
Jason's life was altered by Steve Jobs' keynote address.
After graduating, Jason joined an incubator.
Jason created a video-dating site first.
Bad idea.
Nobody wanted to use it when it was released, so they shut it down.
He made a multiplayer game.
It was released on Bebo. 10,000 people played it.
When Steve Jobs unveiled the Apple app store, he stopped playing.
The introduction of the app store resembled that of a new gaming console.
Jason's life altered after Steve Jobs' 2008 address.
“Whenever a new video game console is launched, that’s the opportunity for a new video game studio to get started, it’s because there aren’t too many games available…When a new PlayStation comes out, since it’s a new system, there’s only a handful of titles available… If you can be a launch title you can get a lot of distribution.”
Apple's app store provided a chance to start a video game company.
They released an app after 5 months of work.
Aurora Feint is the game.
Jason believed 1000 players in a week would be wonderful. A thousand players joined in the first hour.
Over time, Aurora Feints' game didn't gain traction. They don't make enough money to keep playing.
They could only make enough for one month.
Instead of buying video games, buy technology
Jason saw that they established a leaderboard, chat rooms, and multiplayer capabilities and believed other developers would want to use these.
They opted to sell the prior game's technology.
OpenFeint.
Assisting other game developers
They had no money in the bank to create everything needed to make the technology user-friendly.
Jason and Daniel designed a website saying:
“If you’re making a video game and want to have a drop in multiplayer support, you can use our system”
TechCrunch covered their website launch, and they gained a few hundred mailing list subscribers.
They raised seed funding with the mailing list.
Nearly all iPhone game developers started adopting the Open Feint logo.
“It was pretty wild… It was really like a whole social platform for people to play with their friends.”
What kind of a business model was it?
OpenFeint originally planned to make the software free for all games. As the game gained popularity, they demanded payment.
They later concluded it wasn't a good business concept.
It became free eventually.
Acquired for $104 million
Open Feint's users and employees grew tremendously.
GREE bought OpenFeint for $104 million in April 2011.
GREE initially committed to helping Jason and his team build a fantastic company.
Three or four months after the acquisition, Jason recognized they had a different vision.
He quit.
Jason's Original Vision for the iPad
Jason focused on distribution in 2012 to help businesses stand out.
The iPad market and user base were growing tremendously.
Jason said the iPad may replace mobile gadgets.
iPad gamers behaved differently than mobile gamers.
People sat longer and experienced more using an iPad.
“The idea I had was what if we built a gaming business that was more like traditional video games but played on tablets as opposed to some kind of mobile game that I’ve been doing before.”
Unexpected insight after researching the video game industry
Jason learned from studying the gaming industry that long-standing companies had advantages beyond a single release.
Previously, long-standing video game firms had their own distribution system. This distribution strategy could buffer time between successful titles.
Sony, Microsoft, and Valve all have gaming consoles and online stores.
So he built a distribution system.
He created a group chat app for gamers.
He envisioned a team-based multiplayer game with text and voice interaction.
His objective was to develop a communication network, release more games, and start a game distribution business.
Remaking the video game League of Legends
Jason and his crew reimagined a League of Legends game mode for 12-inch glass.
They adapted the game for tablets.
League of Legends was PC-only.
So they rebuilt it.
They overhauled the game and included native mobile experiences to stand out.
Hammer and Chisel was the company's name.
18 people worked on the game.
The game was funded. The game took 2.5 years to make.
Was the game a success?
July 2014 marked the game's release. The team's hopes were dashed.
Critics initially praised the game.
Initial installation was widespread.
The game failed.
As time passed, the team realized iPad gaming wouldn't increase much and mobile would win.
Jason was given a fresh idea by Stan Vishnevskiy.
Stan Vishnevskiy was a corporate engineer.
He told Jason about his plan to design a communication app without a game.
This concept seeded modern strife.
“The insight that he really had was to put a couple of dots together… we’re seeing our customers communicating around our own game with all these different apps and also ourselves when we’re playing on PC… We should solve that problem directly rather than needing to build a new game…we should start making it on PC.”
So began Discord.
Online socializing with pals was the newest trend.
Jason grew up playing video games with his friends.
He never played outside.
Jason had many great moments playing video games with his closest buddy, wife, and brother.
Discord was about providing a location for you and your group to speak and hang out.
Like a private cafe, bedroom, or living room.
Discord was developed for you and your friends on computers and phones.
You can quickly call your buddies during a game to conduct a conference call. Put the call on speaker and talk while playing.
Discord wanted to give every player a unique experience. Because coordinating across apps was a headache.
The entire team started concentrating on Discord.
Jason decided Hammer and Chisel would focus on their chat app.
Jason didn't want to make a video game.
How Discord attracted the appropriate attention
During the first five months, the entire team worked on the game and got feedback from friends.
This ensures product improvement. As a result, some teammates' buddies started utilizing Discord.
The team knew it would become something, but the result was buggy. App occasionally crashed.
Jason persuaded a gamer friend to write on Reddit about the software.
New people would find Discord. Why not?
Reddit users discovered Discord and 50 started using it frequently.
Discord was launched.
Rejecting the $10 billion acquisition proposal
Discord has increased in recent years.
It sends billions of messages.
Discord's users aren't tracked. They're privacy-focused.
Purchase offer
Covid boosted Discord's user base.
Weekly, billions of messages were transmitted.
Microsoft offered $10 billion for Discord in 2021.
Jason sold Open Feint for $104m in 2011.
This time, he believed in the product so much that he rejected Microsoft's offer.
“I was talking to some people in the team about which way we could go… The good thing was that most of the team wanted to continue building.”
Last time, Discord was valued at $15 billion.
Discord raised money on March 12, 2022.
The $15 billion corporation raised $500 million in 2021.

MartinEdic
3 years ago
Russia Through the Windows: It's Very Bad
And why we must keep arming Ukraine
Russian expatriates write about horrific news from home.
Read this from Nadin Brzezinski. She's not a native English speaker, so there are grammar errors, but her tale smells true.
Terrible truth.
There's much more that reveals Russia's grim reality.
Non-leadership. Millions of missing supplies are presumably sold for profit, leaving untrained troops without food or gear. Missile attacks pause because they run out. Fake schemes to hold talks as a way of stalling while they scramble for solutions.
Street men were mobilized. Millions will be ground up to please a crazed despot. Fear, wrath, and hunger pull apart civilization.
It's the most dystopian story, but Ukraine is worse. Destruction of a society, country, and civilization. Only the invaders' corruption and incompetence save the Ukrainians.
Rochester, NY. My suburb had many Soviet-era Ukrainian refugees. Their kids were my classmates. Fifty years later, many are still my friends. I loved their food and culture. My town has 20,000 Ukrainians.
Grieving but determined. They don't quit. They won't quit. Russians are eternal enemies.
It's the Russian people's willingness to tolerate corruption, abuse, and stupidity by their leaders. They are paying. 65000 dead. Ruined economy. No freedom to speak. Americans do not appreciate that freedom as we should.
It lets me write/publish.
Russian friends are shocked. Many are here because their parents escaped Russian anti-semitism and authoritarian oppression. A Russian cultural legacy says a strongman's methods are admirable.
A legacy of a slavery history disguised as serfdom. Peasants and Princes.
Read Tolstoy. Then Anna Karenina. The main characters are princes and counts, whose leaders are incompetent idiots with wealth and power.
Peasants who die in their wars due to incompetence are nameless ciphers.
Sound familiar?
