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.

Joseph Mavericks
3 years ago
5 books my CEO read to make $30M
Offices without books are like bodies without souls.

After 10 years, my CEO sold his company for $30 million. I've shared many of his lessons on medium. You could ask him anything at his always-open office. He also said we could use his office for meetings while he was away. When I used his office for work, I was always struck by how many books he had.
Books are useful in almost every aspect of learning. Building a business, improving family relationships, learning a new language, a new skill... Books teach, guide, and structure. Whether fiction or nonfiction, books inspire, give ideas, and develop critical thinking skills.
My CEO prefers non-fiction and attends a Friday book club. This article discusses 5 books I found in his office that impacted my life/business. My CEO sold his company for $30 million, but I've built a steady business through blogging and video making.
I recall events and lessons I learned from my CEO and how they relate to each book, and I explain how I applied the book's lessons to my business and life.
Note: This post has no affiliate links.
1. The One Thing — Gary Keller

Gary Keller, a real estate agent, wanted more customers. So he and his team brainstormed ways to get more customers. They decided to write a bestseller about work and productivity. The more people who saw the book, the more customers they'd get.
Gary Keller focused on writing the best book on productivity, work, and efficiency for months. His business experience. Keller's business grew after the book's release.
The author summarizes the book in one question.
"What's the one thing that will make everything else easier or unnecessary?"
When I started my blog and business alongside my 9–5, I quickly identified my one thing: writing. My business relied on it, so it had to be great. Without writing, there was no content, traffic, or business.
My CEO focused on funding when he started his business. Even in his final years, he spent a lot of time on the phone with investors, either to get more money or to explain what he was doing with it. My CEO's top concern was money, and the other super important factors were handled by separate teams.
Product tech and design
Incredible customer support team
Excellent promotion team
Profitable sales team
My CEO didn't always focus on one thing and ignore the rest. He was on all of those teams when I started my job. He'd start his day in tech, have lunch with marketing, and then work in sales. He was in his office on the phone at night.
He eventually realized his errors. Investors told him he couldn't do everything for the company. If needed, he had to change internally. He learned to let go, mind his own business, and focus for the next four years. Then he sold for $30 million.
The bigger your project/company/idea, the more you'll need to delegate to stay laser-focused. I started something new every few months for 10 years before realizing this. So much to do makes it easy to avoid progress. Once you identify the most important aspect of your project and enlist others' help, you'll be successful.
2. Eat That Frog — Brian Tracy

The author quote sums up book's essence:
Mark Twain said that if you eat a live frog in the morning, it's probably the worst thing that will happen to you all day. Your "frog" is the biggest, most important task you're most likely to procrastinate on.
"Frog" and "One Thing" are both about focusing on what's most important. Eat That Frog recommends doing the most important task first thing in the morning.
I shared my CEO's calendar in an article 10 months ago. Like this:

CEO's average week (some information crossed out for confidentiality)
Notice anything about 8am-8:45am? Almost every day is the same (except Friday). My CEO started his day with a management check-in for 2 reasons:
Checking in with all managers is cognitively demanding, and my CEO is a morning person.
In a young startup where everyone is busy, the morning management check-in was crucial. After 10 am, you couldn't gather all managers.
When I started my blog, writing was my passion. I'm a morning person, so I woke up at 6 am and started writing by 6:30 am every day for a year. This allowed me to publish 3 articles a week for 52 weeks to build my blog and audience. After 2 years, I'm not stopping.
3. Deep Work — Cal Newport

Deep work is focusing on a cognitively demanding task without distractions (like a morning management meeting). It helps you master complex information quickly and produce better results faster. In a competitive world 10 or 20 years ago, focus wasn't a huge advantage. Smartphones, emails, and social media made focus a rare, valuable skill.
Most people can't focus anymore. Screens light up, notifications buzz, emails arrive, Instagram feeds... Many people don't realize they're interrupted because it's become part of their normal workflow.
Cal Newport mentions Bill Gates' "Think Weeks" in Deep Work.
Microsoft CEO Bill Gates would isolate himself (often in a lakeside cottage) twice a year to read and think big thoughts.
Inside Bill's Brain on Netflix shows Newport's lakeside cottage. I've always wanted a lakeside cabin to work in. My CEO bought a lakehouse after selling his company, but now he's retired.
As a company grows, you can focus less on it. In a previous section, I said investors told my CEO to get back to basics and stop micromanaging. My CEO's commitment and ability to get work done helped save the company. His deep work and new frameworks helped us survive the corona crisis (more on this later).
The ability to deep work will be a huge competitive advantage in the next century. Those who learn to work deeply will likely be successful while everyone else is glued to their screens, Bluetooth-synced to their watches, and playing Candy Crush on their tablets.
4. The 7 Habits of Highly Effective People — Stephen R. Covey

It took me a while to start reading this book because it seemed like another shallow self-help bible. I kept finding this book when researching self-improvement. I tried it because it was everywhere.
Stephen Covey taught me 2 years ago to have a personal mission statement.
A 7 Habits mission statement describes the life you want to lead, the character traits you want to embody, and the impact you want to have on others. shortform.com
I've had many lunches with my CEO and talked about Vipassana meditation and Sunday forest runs, but I've never seen his mission statement. I'm sure his family is important, though. In the above calendar screenshot, you can see he always included family events (in green) so we could all see those time slots. We couldn't book him then. Although he never spent as much time with his family as he wanted, he always made sure to be on time for his kid's birthday rather than a conference call.
My CEO emphasized his company's mission. Your mission statement should answer 3 questions.
What does your company do?
How does it do it?
Why does your company do it?
As a graphic designer, I had to create mission-statement posters. My CEO hung posters in each office.
5. Measure What Matters — John Doerr

This book is about Andrew Grove's OKR strategy, developed in 1968. When he joined Google's early investors board, he introduced it to Larry Page and Sergey Brin. Google still uses OKR.
Objective Key Results
Objective: It explains your goals and desired outcome. When one goal is reached, another replaces it. OKR objectives aren't technical, measured, or numerical. They must be clear.
Key Result should be precise, technical, and measurable, unlike the Objective. It shows if the Goal is being worked on. Time-bound results are quarterly or yearly.
Our company almost sank several times. Sales goals were missed, management failed, and bad decisions were made. On a Monday, our CEO announced we'd implement OKR to revamp our processes.
This was a year before the pandemic, and I'm certain we wouldn't have sold millions or survived without this change. This book impacted the company the most, not just management but all levels. Organization and transparency improved. We reached realistic goals. Happy investors. We used the online tool Gtmhub to implement OKR across the organization.

My CEO's company went from near bankruptcy to being acquired for $30 million in 2 years after implementing OKR.
I hope you enjoyed this booklist. Here's a recap of the 5 books and the lessons I learned from each.
The 7 Habits of Highly Effective People — Stephen R. Covey
Have a mission statement that outlines your goals, character traits, and impact on others.
Deep Work — Cal Newport
Focus is a rare skill; master it. Deep workers will succeed in our hyper-connected, distracted world.
The One Thing — Gary Keller
What can you do that will make everything else easier or unnecessary? Once you've identified it, focus on it.
Eat That Frog — Brian Tracy
Identify your most important task the night before and do it first thing in the morning. You'll have a lighter day.
Measure What Matters — John Doerr
On a timeline, divide each long-term goal into chunks. Divide those slices into daily tasks (your goals). Time-bound results are quarterly or yearly. Objectives aren't measured or numbered.
Thanks for reading. Enjoy the ride!

Greg Satell
2 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.
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Suzie Glassman
3 years ago
How I Stay Fit Despite Eating Fast Food and Drinking Alcohol
Here's me. Perfectionism is unnecessary.
This post isn't for people who gag at the prospect of eating french fries. I've been ridiculed for stating you can lose weight eating carbs and six-pack abs aren't good.
My family eats frozen processed meals and quick food most weeks (sometimes more). Clean eaters may think I'm unqualified to give fitness advice. I get it.
Hear me out, though. I’m a 44-year-old raising two busy kids with a weekly-traveling husband. Tutoring, dance, and guitar classes fill weeknights. I'm also juggling my job and freelancing.
I'm as worried and tired as my clients. I wish I ate only kale smoothies and salads. I can’t. Despite my mistakes, I'm fit. I won't promise you something just because it worked for me. But here’s a look at how I manage.
What I largely get right about eating
I have a flexible diet and track my daily intake. I count protein, fat, and carbs. Only on vacation or exceptional occasions do I not track.
My protein goal is 1 g per lb. I consume a lot of chicken breasts, eggs, turkey, and lean ground beef. I also occasionally drink protein shakes.
I eat 220–240 grams of carbs daily. My carb count depends on training volume and goals. I'm trying to lose weight slowly. If I want to lose weight faster, I cut carbs to 150-180.
My carbs include white rice, Daves Killer Bread, fruit, pasta, and veggies. I don't eat enough vegetables, so I take Athletic Greens. Also, V8.
Fat grams over 50 help me control my hormones. Recently, I've reached 70-80 grams. Cooking with olive oil. I eat daily dark chocolate. Eggs, butter, milk, and cheese contribute to the rest.
Those frozen meals? What can I say? Stouffer’s lasagna is sometimes needed. I order the healthiest fast food I can find (although I can never bring myself to order the salad). That's a chicken sandwich or a kid's hamburger. I rarely order fries. I eat slowly and savor each bite to feel full.
Potato chips and sugary cereals are in the pantry, but I'm not tempted. My kids eat them because I'd rather teach them moderation than total avoidance. If I eat them, I only eat one portion.
If you're not hungry and eating enough protein and fat, you won't want to eat everything in sight.
I drink once or twice a week. As a result, I rarely overdo it.
Food tracking is tedious and frustrating for many. Taking breaks and using estimates when eating out help. Not perfect, but realistic.
I practice a prolonged fast to enhance metabolic adaptability
Metabolic flexibility is the ability to switch between fuel sources (fat and carbs) based on activity intensity and time since eating. At rest or during low to moderate exertion, your body burns fat. Your body burns carbs after eating and during intense exercise.
Our metabolic flexibility can be hampered by lack of exercise, overeating, and stress. Our bodies become lousy fat burners, making weight loss difficult.
Once a week, I skip dinner (usually around 24 hours). Long-term fasting teaches my body to burn fat. It provides me one low-calorie day a week (I break the fast with a normal-sized dinner).
Fasting day helps me maintain my weight on weekends, when I typically overeat and drink.
Try an extended fast slowly. Delay breakfast by two hours. Next week, add two hours, etc. It takes practice to go that long without biting off your arm. I also suggest consulting your doctor.
I stay active.
I've always been active. As a child, I danced many nights a week, was on the high school dance team, and ran marathons in my 20s.
Often, I feel driven by an internal engine. Working from home makes it easy to exercise. If that’s not you, I get it. Everyone can benefit from raising their baseline.
After taking the kids to school, I walk two miles around the neighborhood. When I need to think, I switch off podcasts. First thing in the morning, I go for a walk.
I lift weights Monday, Wednesday, and Friday. 45 minutes is typical. I run 45-90 minutes on Tuesday and Thursday. I'm slow but reliable. On Saturdays and Sundays, I walk and add a short spin class if I'm not too tired.
I almost never forgo sleep.
I rarely stay up past 10 p.m., much to my night-owl husband's dismay. My 7-8-hour nights help me recover from workouts and handle stress. Without it, I'm grumpy.
I suppose sleep duration matters more than bedtime. Some people just can't fall asleep early. Internal clock and genetics determine sleep and wake hours.
Prioritize sleep.
Last thoughts
Fitness and diet advice is often useless. Some of the advice is inaccurate, dangerous, or difficult to follow if you have a life. I want to throw a shoe at my screen when I see headlines promising to speed up my metabolism or help me lose fat.
I studied exercise physiology for years. No shortcuts exist. No medications or cleanses reset metabolism. I play the hand I'm dealt. I realize that just because something works for me, it won't for you.
If I wanted 15% body fat and ripped abs, I'd have to be stricter. I occasionally think I’d like to get there. But then I remember I’m happy with my life. I like fast food and beer. Pizza and margaritas are favorites (not every day).
You can get it mostly right and live a healthy life.

DC Palter
3 years ago
How Will You Generate $100 Million in Revenue? The Startup Business Plan
A top-down company plan facilitates decision-making and impresses investors.
A startup business plan starts with the product, the target customers, how to reach them, and how to grow the business.
Bottom-up is terrific unless venture investors fund it.
If it can prove how it can exceed $100M in sales, investors will invest. If not, the business may be wonderful, but it's not venture capital-investable.
As a rule, venture investors only fund firms that expect to reach $100M within 5 years.
Investors get nothing until an acquisition or IPO. To make up for 90% of failed investments and still generate 20% annual returns, portfolio successes must exit with a 25x return. A $20M-valued company must be acquired for $500M or more.
This requires $100M in sales (or being on a nearly vertical trajectory to get there). The company has 5 years to attain that milestone and create the requisite ROI.
This motivates venture investors (venture funds and angel investors) to hunt for $100M firms within 5 years. When you pitch investors, you outline how you'll achieve that aim.
I'm wary of pitches after seeing a million hockey sticks predicting $5M to $100M in year 5 that never materialized. Doubtful.
Startups fail because they don't have enough clients, not because they don't produce a great product. That jump from $5M to $100M never happens. The company reaches $5M or $10M, growing at 10% or 20% per year. That's great, but not enough for a $500 million deal.
Once it becomes clear the company won’t reach orbit, investors write it off as a loss. When a corporation runs out of money, it's shut down or sold in a fire sale. The company can survive if expenses are trimmed to match revenues, but investors lose everything.
When I hear a pitch, I'm not looking for bright income projections but a viable plan to achieve them. Answer these questions in your pitch.
Is the market size sufficient to generate $100 million in revenue?
Will the initial beachhead market serve as a springboard to the larger market or as quicksand that hinders progress?
What marketing plan will bring in $100 million in revenue? Is the market diffuse and will cost millions of dollars in advertising, or is it one, focused market that can be tackled with a team of salespeople?
Will the business be able to bridge the gap from a small but fervent set of early adopters to a larger user base and avoid lock-in with their current solution?
Will the team be able to manage a $100 million company with hundreds of people, or will hypergrowth force the organization to collapse into chaos?
Once the company starts stealing market share from the industry giants, how will it deter copycats?
The requirement to reach $100M may be onerous, but it provides a context for difficult decisions: What should the product be? Where should we concentrate? who should we hire? Every strategic choice must consider how to reach $100M in 5 years.
Focusing on $100M streamlines investor pitches. Instead of explaining everything, focus on how you'll attain $100M.
As an investor, I know I'll lose my money if the startup doesn't reach this milestone, so the revenue prediction is the first thing I look at in a pitch deck.
Reaching the $100M goal needs to be the first thing the entrepreneur thinks about when putting together the business plan, the central story of the pitch, and the criteria for every important decision the company makes.

B Kean
3 years ago
Russia's greatest fear is that no one will ever fear it again.
When everyone laughs at him, he's powerless.
1-2-3: Fold your hands and chuckle heartily. Repeat until you're really laughing.
We're laughing at Russia's modern-day shortcomings, if you hadn't guessed.
Watch Good Fellas' laughing scene on YouTube. Ray Liotta, Joe Pesci, and others laugh hysterically in a movie. Laugh at that scene, then think of Putin's macho guy statement on February 24 when he invaded Ukraine. It's cathartic to laugh at his expense.
Right? It makes me feel great that he was convinced the military action will be over in a week. I love reading about Putin's morning speech. Many stupid people on Earth supported him. Many loons hailed his speech historic.
Russia preys on the weak. Strong Ukraine overcame Russia. Ukraine's right. As usual, Russia is in the wrong.
A so-called thought leader recently complained on Russian TV that the West no longer fears Russia, which is why Ukraine is kicking Russia's ass.
Let's simplify for this Russian intellectual. Except for nuclear missiles, the West has nothing to fear from Russia. Russia is a weak, morally-empty country whose DNA has degraded to the point that evolution is already working to flush it out.
The West doesn't fear Russia since he heads a prominent Russian institution. Russian universities are intellectually barren. I taught at St. Petersburg University till June (since February I was virtually teaching) and was astounded by the lack of expertise.
Russians excel in science, math, engineering, IT, and anything that doesn't demand critical thinking or personal ideas.
Reflecting on many of the high-ranking individuals from around the West, Satanovsky said: “They are not interested in us. We only think we’re ‘big politics’ for them but for those guys we’re small politics. “We’re small politics, even though we think of ourselves as the descendants of the Russian Empire, of the USSR. We are not the Soviet Union, we don’t have enough weirdos and lunatics, we practically don’t have any (U.S. Has Stopped Fearing Us).”
Professor Dmitry Evstafiev, president of the Institute of the Middle East, praised Nikita Khrushchev's fiery nature because he made the world fear him, which made the Soviet Union great. If the world believes Putin is crazy, then Russia will be great, says this man. This is crazy.
Evstafiev covered his cowardice by saluting Putin. He praised his culture and Ukraine patience. This weakling professor ingratiates himself to Putin instead of calling him a cowardly, demonic shithead.
This is why we don't fear Russia, professor. Because you're all sycophantic weaklings who sold your souls to a Leningrad narcissist. Putin's nothing. He lacks intelligence. You've tied your country's fate and youth's future to this terrible monster. Disgraceful!
How can you loathe your country's youth so much to doom them to decades or centuries of ignominy? My son is half Russian and must now live with this portion of him.
We don't fear Russia because you don't realize that it should be appreciated, not frightened. That would need lobotomizing tens of millions of people like you.
Sadman. You let a Leningrad weakling castrate you and display your testicles. He shakes the container, saying, "Your balls are mine."
Why is Russia not feared?
Your self-inflicted national catastrophe is hilarious. Sadly, it's laugh-through-tears.