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.

Sammy Abdullah
3 years ago
Payouts to founders at IPO
How much do startup founders make after an IPO? We looked at 2018's major tech IPOs. Paydays aren't what founders took home at the IPO (shares are normally locked up for 6 months), but what they were worth at the IPO price on the day the firm went public. It's not cash, but it's nice. Here's the data.
Several points are noteworthy.
Huge payoffs. Median and average pay were $399m and $918m. Average and median homeownership were 9% and 12%.
Coinbase, Uber, UI Path. Uber, Zoom, Spotify, UI Path, and Coinbase founders raised billions. Zoom's founder owned 19% and Spotify's 28% and 13%. Brian Armstrong controlled 20% of Coinbase at IPO and was worth $15bn. Preserving as much equity as possible by staying cash-efficient or raising at high valuations also helps.
The smallest was Ping. Ping's compensation was the smallest. Andre Duand owned 2% but was worth $20m at IPO. That's less than some billion-dollar paydays, but still good.
IPOs can be lucrative, as you can see. Preserving equity could be the difference between a $20mm and $15bln payday (Coinbase).
Jason Kottke
3 years ago
Lessons on Leadership from the Dancing Guy
This is arguably the best three-minute demonstration I've ever seen of anything. Derek Sivers turns a shaky video of a lone dancing guy at a music festival into a leadership lesson.
A leader must have the courage to stand alone and appear silly. But what he's doing is so straightforward that it's almost instructive. This is critical. You must be simple to follow!
Now comes the first follower, who plays an important role: he publicly demonstrates how to follow. The leader embraces him as an equal, so it's no longer about the leader — it's about them, plural. He's inviting his friends to join him. It takes courage to be the first follower! You stand out and dare to be mocked. Being a first follower is a style of leadership that is underappreciated. The first follower elevates a lone nut to the position of leader. If the first follower is the spark that starts the fire, the leader is the flint.
This link was sent to me by @ottmark, who noted its resemblance to Kurt Vonnegut's three categories of specialists required for revolution.
The rarest of these specialists, he claims, is an actual genius – a person capable generating seemingly wonderful ideas that are not widely known. "A genius working alone is generally dismissed as a crazy," he claims.
The second type of specialist is much easier to find: a highly intellectual person in good standing in his or her community who understands and admires the genius's new ideas and can attest that the genius is not insane. "A person like him working alone can only crave loudly for changes, but fail to say what their shapes should be," Slazinger argues.
Jeff Veen reduced the three personalities to "the inventor, the investor, and the evangelist" on Twitter.
You might also like

Will Leitch
2 years ago
Don't treat Elon Musk like Trump.
He’s not the President. Stop treating him like one.
Elon Musk tweeted from Qatar, where he was watching the World Cup Final with Jared Kushner.
Musk's subsequent Tweets were as normal, basic, and bland as anyone's from a World Cup Final: It's depressing to see the world's richest man looking at his phone during a grand ceremony. Rich guy goes to rich guy event didn't seem important.
Before Musk posted his should-I-step-down-at-Twitter poll, CNN ran a long segment asking if it was hypocritical for him to reveal his real-time location after defending his (very dumb) suspension of several journalists for (supposedly) revealing his assassination coordinates by linking to a site that tracks Musks private jet. It was hard to ignore CNN's hypocrisy: It covered Musk as Twitter CEO like President Trump. EVERY TRUMP STORY WAS BASED ON HIM SAYING X, THEN DOING Y. Trump would do something horrific, lie about it, then pretend it was fine, then condemn a political rival who did the same thing, be called hypocritical, and so on. It lasted four years. Exhausting.
It made sense because Trump was the President of the United States. The press's main purpose is to relentlessly cover and question the president.
It's strange to say this out. Twitter isn't America. Elon Musk isn't a president. He maintains a money-losing social media service to harass and mock people he doesn't like. Treating Musk like Trump, as if he should be held accountable like Trump, shows a startling lack of perspective. Some journalists treat Twitter like a country.
The compulsive, desperate way many journalists utilize the site suggests as much. Twitter isn't the town square, despite popular belief. It's a place for obsessives to meet and converse. Journalists say they're breaking news. Their careers depend on it. They can argue it's a public service. Nope. It's a place lonely people go to speak all day. Twitter. So do journalists, Trump, and Musk. Acting as if it has a greater purpose, as if it's impossible to break news without it, or as if the republic is in peril is ludicrous. Only 23% of Americans are on Twitter, while 25% account for 97% of Tweets. I'd think a large portion of that 25% are journalists (or attention addicts) chatting to other journalists. Their loudness makes Twitter seem more important than it is. Nope. It's another stupid website. They were there before Twitter; they will be there after Twitter. It’s just a website. We can all get off it if we want. Most of us aren’t even on it in the first place.
Musk is a website-owner. No world leader. He's not as accountable as Trump was. Musk is cable news's primary character now that Trump isn't (at least for now). Becoming a TV news anchor isn't as significant as being president. Elon Musk isn't as important as we all pretend, and Twitter isn't even close. Twitter is a dumb website, Elon Musk is a rich guy going through a midlife crisis, and cable news is lazy because its leaders thought the entire world was on Twitter and are now freaking out that their playground is being disturbed.
I’ve said before that you need to leave Twitter, now. But even if you’re still on it, we need to stop pretending it matters more than it does. It’s a site for lonely attention addicts, from the man who runs it to the journalists who can’t let go of it. It’s not a town square. It’s not a country. It’s not even a successful website. Let’s stop pretending any of it’s real. It’s not.

Francesca Furchtgott
3 years ago
Giving customers what they want or betraying the values of the brand?
A J.Crew collaboration for fashion label Eveliina Vintage is not a paradox; it is a solution.
Eveliina Vintage's capsule collection debuted yesterday at J.Crew. This J.Crew partnership stopped me in my tracks.
Eveliina Vintage sells vintage goods. Eeva Musacchia founded the shop in Finland in the 1970s. It's recognized for its one-of-a-kind slip dresses from the 1930s and 1940s.
I wondered why a vintage brand would partner with a mass shop. Fast fashion against vintage shopping? Will Eveliina Vintages customers be turned off?
But Eveliina Vintages customers don't care about sustainability. They want Eveliina's Instagram look. Eveliina Vintage collaborated with J.Crew to give customers what they wanted: more Eveliina at a lower price.
Vintage: A Fashion Option That Is Eco-Conscious
Secondhand shopping is a trendy response to quick fashion. J.Crew releases hundreds of styles annually. Waste and environmental damage have been criticized. A pair of jeans requires 1,800 gallons of water. J.Crew's limited-time deals promote more purchases. J.Crew items are likely among those Americans wear 7 times before discarding.
Consumers and designers have emphasized sustainability in recent years. Stella McCartney and Eileen Fisher are popular eco-friendly brands. They've also flocked to ThredUp and similar sites.
Gap, Levis, and Allbirds have listened to consumer requests. They promote recycling, ethical sourcing, and secondhand shopping.
Secondhand shoppers feel good about reusing and recycling clothing that might have ended up in a landfill.
Eco-conscious fashionistas shop vintage. These shoppers enjoy the thrill of the hunt (that limited-edition Chanel bag!) and showing off a unique piece (nobody will have my look!). They also reduce their environmental impact.
Is Eveliina Vintage capitalizing on an aesthetic or is it a sustainable brand?
Eveliina Vintage emphasizes environmental responsibility. Vogue's Amanda Musacchia emphasized sustainability. Amanda, founder Eeva's daughter, is a company leader.
But Eveliina's press message doesn't address sustainability, unlike Instagram. Scarcity and fame rule.
Eveliina Vintages Instagram has see-through dresses and lace-trimmed slip dresses. Celebrities and influencers are often photographed in Eveliina's apparel, which has 53,000+ followers. Vogue appreciates Eveliina's style. Multiple publications discuss Alexa Chung's Eveliina dress.
Eveliina Vintage markets its one-of-a-kind goods. It teases future content, encouraging visitors to return. Scarcity drives demand and raises clothing prices. One dress is $1,600+, but most are $500-$1,000.
The catch: Eveliina can't monetize its expanding popularity due to exorbitant prices and limited quantity. Why?
Most people struggle to pay for their clothing. But Eveliina Vintage lacks those more affordable entry-level products, in contrast to other luxury labels that sell accessories or perfume.
Many people have trouble fitting into their clothing. The bodies of most women in the past were different from those for which vintage clothing was designed. Each Eveliina dress's specific measurements are mentioned alongside it. Be careful, you can fall in love with an ill-fitting dress.
No matter how many people can afford it and fit into it, there is only one item to sell. To get the item before someone else does, those people must be on the Eveliina Vintage website as soon as it becomes available.
A Way for Eveliina Vintage to Make Money (and Expand) with J.Crew Its following
Eveliina Vintages' cooperation with J.Crew makes commercial sense.
This partnership spreads Eveliina's style. Slightly better pricing The $390 outfits have multicolored slips and gauzy cotton gowns. Sizes range from 00 to 24, which is wider than vintage racks.
Eveliina Vintage customers like the combination. Excited comments flood the brand's Instagram launch post. Nobody is mocking the 50-year-old vintage brand's fast-fashion partnership.
Vintage may be a sustainable fashion trend, but that's not why Eveliina's clients love the brand. They only care about the old look.
And that is a tale as old as fashion.
Blake Montgomery
3 years ago
Explaining Twitter Files
Elon Musk, Matt Taibbi, the 'Twitter Files,' and Hunter Biden's laptop: what gives?
Explaining Twitter Files
Matt Taibbi released "The Twitter Files," a batch of emails sent by Twitter executives discussing the company's decision to stop an October 2020 New York Post story online.
What's on Twitter? New York Post and Fox News call them "bombshell" documents. Or, as a Post columnist admitted, are they "not the smoking gun"? Onward!
What started this?
The New York Post published an exclusive, potentially explosive story in October 2020: Biden's Secret Emails: Ukrainian executive thanks Hunter Biden for'meeting' veep dad. The story purported to report the contents of a laptop brought to the tabloid by a Delaware computer repair shop owner who said it belonged to President Biden's second son, Hunter Biden. Emails and files on the laptop allegedly showed how Hunter peddled influence with Ukranian businessmen and included a "raunchy 12-minute video" of Hunter smoking crack and having sex.
Twitter banned links to the Post story after it was published, calling it "hacked material." The Post's Twitter account was suspended for multiple days.
Why? Yoel Roth, Twitter's former head of trust and safety, said the company couldn't verify the story, implying they didn't trust the Post.
Twitter's stated purpose rarely includes verifying news stories. This seemed like intentional political interference. This story was hard to verify because the people who claimed to have found the laptop wouldn't give it to other newspapers. (Much of the story, including Hunter's business dealings in Ukraine and China, was later confirmed.)
Roth: "It looked like a hack and leak."
So what are the “Twitter Files?”
Twitter's decision to bury the story became a political scandal, and new CEO Elon Musk promised an explanation. The Twitter Files, named after Facebook leaks.
Musk promised exclusive details of "what really happened" with Hunter Biden late Friday afternoon. The tweet was punctuated with a popcorn emoji.
Explaining Twitter Files
Three hours later, journalist Matt Taibbi tweeted more than three dozen tweets based on internal Twitter documents that revealed "a Frankensteinian tale of a human-built mechanism grown out of its designer's control."
Musk sees this release as a way to shape Twitter's public perception and internal culture in his image. We don't know if the CEO gave Taibbi the documents. Musk hyped the document dump before and during publication, but Taibbi cited "internal sources."
Taibbi shares email screenshots showing Twitter execs discussing the Post story and blocking its distribution. Taibbi says the emails show Twitter's "extraordinary steps" to bury the story.
Twitter communications chief Brandon Borrman has the most damning quote in the Files. Can we say this is policy? The story seemed unbelievable. It seemed like a hack... or not? Could Twitter, which ex-CEO Dick Costolo called "the free speech wing of the free speech party," censor a news story?
Many on the right say the Twitter Files prove the company acted at the behest of Democrats. Both parties had these tools, writes Taibbi. In 2020, both the Trump White House and Biden campaign made requests. He says the system for reporting tweets for deletion is unbalanced because Twitter employees' political donations favor Democrats. Perhaps. These donations may have helped Democrats connect with Twitter staff, but it's also possible they didn't. No emails in Taibbi's cache show these alleged illicit relations or any actions Twitter employees took as a result.
Even Musk's supporters were surprised by the drop. Miranda Devine of the New York Post told Tucker Carlson the documents weren't "the smoking gun we'd hoped for." Sebastian Gorka said on Truth Social, "So far, I'm deeply underwhelmed." DC Democrats collude with Palo Alto Democrats. Whoop!” The Washington Free Beacon's Joe Simonson said the Twitter files are "underwhelming." Twitter was staffed by Democrats who did their bidding. (Why?)
If "The Twitter Files" matter, why?
These emails led Twitter to suppress the Hunter Biden laptop story has real news value. It's rare for a large and valuable company like Twitter to address wrongdoing so thoroughly. Emails resemble FOIA documents. They describe internal drama at a company with government-level power. Katie Notopoulos tweeted, "Any news outlet would've loved this scoop!" It's not a'scandal' as teased."
Twitter's new owner calls it "the de facto public town square," implying public accountability. Like a government agency. Though it's exciting to receive once-hidden documents in response to a FOIA, they may be boring and tell you nothing new. Like Twitter files. We learned how Twitter blocked the Post's story, but not why. Before these documents were released, we knew Twitter had suppressed the story and who was involved.
These people were disciplined and left Twitter. Musk fired Vijaya Gadde, the former CLO who reportedly played a "key role" in the decision. Roth quit over Musk's "dictatorship." Musk arrived after Borrman left. Jack Dorsey, then-CEO, has left. Did those who digitally quarantined the Post's story favor Joe Biden and the Democrats? Republican Party opposition and Trump hatred? New York Post distaste? According to our documents, no. Was there political and press interference? True. We knew.
Taibbi interviewed anonymous ex-Twitter employees about the decision; all expressed shock and outrage. One source said, "Everyone knew this was fucked." Since Taibbi doesn't quote that expletive, we can assume the leaked emails contained few or no sensational quotes. These executives said little to support nefarious claims.
Outlets more invested in the Hunter Biden story than Gizmodo seem vexed by the release and muted headlines. The New York Post, which has never shied away from a blaring headline in its 221-year history, owns the story of Hunter Biden's laptop. Two Friday-night Post alerts about Musk's actions were restrained. Elon Musk will drop Twitter files on NY Post-Hunter Biden laptop censorship today. Elon Musk's Twitter dropped Post censorship details from Biden's laptop. Fox News' Apple News push alert read, "Elon Musk drops Twitter censorship documents."
Bombshell, bombshell, bombshell… what, exactly, is the bombshell? Maybe we've heard this story too much and are missing the big picture. Maybe these documents detail a well-documented decision.
The Post explains why on its website. "Hunter Biden laptop bombshell: Twitter invented reason to censor Post's reporting," its headline says.
Twitter's ad hoc decision to moderate a tabloid's content is not surprising. The social network had done this for years as it battled toxic users—violent white nationalists, virulent transphobes, harassers and bullies of all political stripes, etc. No matter how much Musk crows, the company never had content moderation under control. Buzzfeed's 2016 investigation showed how Twitter has struggled with abusive posters since 2006. Jack Dorsey and his executives improvised, like Musk.
Did the US government interfere with the ex-social VP's media company? That's shocking, a bombshell. Musk said Friday, "Twitter suppressing free speech by itself is not a 1st amendment violation, but acting under government orders with no judicial review is." Indeed! Taibbi believed this. August 2022: "The laptop is secondary." Zeynep Tufecki, a Columbia professor and New York Times columnist, says the FBI is cutting true story distribution. Taibbi retracted the claim Friday night: "I've seen no evidence of government involvement in the laptop story."
What’s the bottom line?
I'm still not sure what's at stake in the Hunter Biden scandal after dozens of New York Post articles, hundreds of hours of Fox News airtime, and thousands of tweets. Briefly: Joe Biden's son left his laptop with a questionable repairman. FBI confiscated it? The repairman made a copy and gave it to Rudy Giuliani's lawyer. The Post got it from Steve Bannon. On that laptop were videos of Hunter Biden smoking crack, cavorting with prostitutes, and emails about introducing his father to a Ukrainian businessman for $50,000 a month. Joe Biden urged Ukraine to fire a prosecutor investigating the company. What? The story seems to be about Biden family business dealings, right?
The discussion has moved past that point anyway. Now, the story is the censorship of it. Adrienne Rich wrote in "Diving Into the Wreck" that she came for "the wreck and not the story of the wreck" No matter how far we go, Hunter Biden's laptop is done. Now, the crash's story matters.
I'm dizzy. Katherine Miller of BuzzFeed wrote, "I know who I believe, and you probably do, too. To believe one is to disbelieve the other, which implicates us in the decision; we're stuck." I'm stuck. Hunter Biden's laptop is a political fabrication. You choose. I've decided.
This could change. Twitter Files drama continues. Taibbi said, "Much more to come." I'm dizzy.
