Blogify Logo

Million Dollar Weekend: Building a Business (and a Life) in 48 Wild Hours

I still remember the day I was fired by Facebook. It wasn’t glamorous; it stung—and it almost choked out my dream of building something on my own. But looking back? That was when the real story began. If you’ve ever stared at your bank account, wondering if you’re cut out for this whole 'entrepreneur' thing, trust me: you’re not alone. Million Dollar Weekend is the book I wish I’d had back when I thought success was reserved for 'special' people. Spoiler: it’s not. Real change starts the moment you swap excuses for experiments and test your ideas with sweaty palms—sometimes, literally over coffee. Here’s my honest, boots-on-the-ground breakdown of how anyone can launch (and scale) a business worth bragging about—without waiting for a green light. Scared? Good. Why Fear is the Secret Sauce to Your Million Dollar Weekend If you’re feeling that tightness in your chest or the flutter in your stomach as you think about launching your own business—good. That’s not a warning sign to stop. It’s a signal you’re onto something real. Fear is the secret sauce to your Million Dollar Weekend. Overcoming fear in entrepreneurship isn’t just a hurdle; it’s the very fuel that will drive you forward. Fear: Your Green Light, Not a Red Flag Let’s be honest: the psychological hurdles in entrepreneurship are universal. The “I’m not ready,” “It’s too risky,” or “I don’t have a good idea” excuses? I’ve heard them all—and lived them. You’re not uniquely unprepared or especially unlucky. Every entrepreneur faces these doubts. The difference is what you do next. Lean in, don’t run. Fear means you care. It means you’re about to step outside your comfort zone, and that’s where all the growth happens. The Facebook Firing: My Most Embarrassing (and Useful) Failure Here’s a story I’ve never stopped learning from: getting fired by Facebook. I was employee #30, and I lost out on a fortune in stock. The embarrassment was public and painful. But that moment—standing in the parking lot with my box of stuff—was the push I needed. It forced me to stop hiding behind “safe” jobs and start experimenting. That setback became the launching pad for everything that followed: AppSumo, Sumo, TidyCal, and more. I want you to see that failure isn’t a dead end. It’s fuel. Every rejection, every “no,” is a step closer to your “yes.” Building Your “Ask Muscle” with Ask Goals and the Coffee Challenge Most people never start because they’re afraid of rejection. That’s why I created the “Ask Goals” and the infamous “Coffee Challenge.” These are simple, weird, but wildly effective ways to build your ‘rejection muscle’—the single biggest game-changer for aspiring entrepreneurs. Ask Goals: Set a target number of asks (for discounts, feedback, partnerships) every week. The goal isn’t to get a “yes”—it’s to get comfortable with “no.” Coffee Challenge: Walk into a coffee shop and ask for 10% or 20% off your order. It’s awkward, but it rewires your brain. Suddenly, rejection isn’t scary—it’s just part of the game. “Developing your Ask muscle is the single biggest game-changer for aspiring entrepreneurs.” – Noah Kagan These exercises aren’t about coffee or discounts. They’re about normalizing discomfort and making bold asks a habit. Growth is usually just one awkward question away. Why Your Freedom Number Beats a 7-Figure Goal Forget the vague dream of “making millions.” What you really need is your Freedom Number—the specific monthly income that gives you true independence. For me, it was $3,000 a month. That number was more motivating and actionable than any seven-figure fantasy. When you know your Freedom Number, the path becomes clear. You’re not chasing someone else’s version of success; you’re building a business that gives you the life you want, on your terms. Quirky Challenge: Growth Is One Awkward Ask Away Still nervous? Try this: walk up to a stranger today and ask for a random 20% discount—on coffee, groceries, anything. You’ll feel your heart race. You might get a weird look. But you’ll survive. And you’ll realize that overcoming fear in entrepreneurship is less about talent and more about action. Every time you do this, you’re rewiring your brain to see fear as a green light, not a stop sign. Remember: entrepreneurship psychological hurdles are normal. The “Ask Goals,” “Coffee Challenge,” and knowing your “Freedom Number” are your tools to smash through them. If you can get comfortable with fear and rejection, you’re already ahead of 99% of would-be founders. That’s the real secret behind every Million Dollar Weekend.NOW, Not How: The Oddly Liberating Power of Starting Before You’re ‘Ready’ If you’re like most aspiring founders, you’ve probably spent more time thinking about how to start a business than actually starting one. I get it—there’s a myth out there that you need the perfect plan, the perfect timing, or the perfect idea before you take the leap. But here’s the truth: waiting kills more dreams than failing ever will. The NOW Not How mindset is about flipping that script—choosing action over endless planning, and learning by doing, not just by thinking. The Myth of Perfect Preparation Let’s be real: you will never feel “ready.” I’ve launched eight million-dollar businesses, and not once did I feel like I had everything figured out before I started. The world rewards people who move, not those who wait. Every day you spend researching, tweaking, or second-guessing is a day someone else is out there learning, iterating, and getting closer to their goals. That’s why the “Just Fu**ing Start” motto is at the heart of Million Dollar Weekend. Get moving—details be damned, for now. You can’t steer a parked car. Bias Toward Action: Why Messy Beats Perfect Here’s a secret: you’ll learn more in 24 hours of messy trial than in two years of research. This bias toward action is the single biggest advantage you can give yourself. I once launched a side gig in an airport lounge after overhearing three travelers complain about charging cables. I whipped up a quick offer, pitched it to a few people, and… it totally flopped. But the process worked. I learned more about what people actually wanted (and didn’t want) in those few hours than I ever could have by reading blog posts or watching YouTube videos. Failure, in this context, is just valuable data—not defeat. The One-Minute Business Model: Instant Validation One of the most practical steps in the NOW Not How mindset is using the One-Minute Business Model. Forget 40-page business plans. Here’s the formula: Price - Cost = Profit That’s it. Can you sell your product for more than it costs you to deliver? If yes, you’re in business. If not, tweak something and try again. I use this back-of-the-napkin math for every new idea. It’s a quick, low-risk way to see if your idea could actually work—before you waste weeks or months building something nobody wants. The Weekend Experiment: 48 Hours to Learn, Not Just Win In Million Dollar Weekend, I challenge you to run a 48-hour business validation sprint. The goal isn’t to build the next unicorn overnight—it’s to get out of your head and into the market. Even if your first experiment “fails,” you win. Why? Because you recalibrate, not retreat. Every attempt gives you real-world feedback, sharpens your instincts, and builds your confidence muscle. Pick an idea: Listen for problems in your life or community. Run the One-Minute Business Model: Does the math work? Launch a business experiment: Try to get three paying customers in 48 hours. Iterate fast: Use what you learn to pivot or improve. Remember, the NOW Not How mindset is about progress, not perfection. Every weekend is a new chance to test, learn, and move closer to your dream. As I always say: “Don’t die with your dream still inside you. Start before you’re ready.” – Noah Kagan So, next time you catch yourself waiting for the “right” moment, remember: action beats theory. The tools, the scripts, and the support are all here. Just start—NOW, not how.The Golden Rule of Validation: Get Three Real Customers or Pivot (Fast) Let’s get brutally honest about business validation: if you can’t get three strangers to pay you for your idea in 48 hours, it’s time to pivot—fast. This is the Golden Rule of Validation I live by and the single most important lesson in Million Dollar Weekend. Forget the endless planning, logo tweaking, and “what if” scenarios. The only thing that matters is whether real people will pay real money for what you’re offering. Everything else is noise. Customer-First Approach: Stop Building for Invisible Users Most aspiring entrepreneurs fall into the “Founder-First” trap—building products for themselves, or worse, for imaginary customers. I’ve been there. It’s easy to get lost in your own head, convinced your idea is genius. But here’s the truth: your opinion doesn’t matter—only your customer’s does. The Customer-First Approach means you listen for pain points everywhere: in your own life, in conversations at coffee shops, in online forums, or even in complaints on social media. Every frustration is a potential business idea waiting to be validated. Anecdote: AppSumo’s $50 Launch—Presold Before Building When I started AppSumo, I didn’t have a product. I had an idea, a $50 budget, and a willingness to test fast. Instead of building out a fancy website or hiring developers, I wrote a simple landing page and pitched the concept to real people. I presold software deals before any actual product existed. Within 48 hours, I had paying customers—and only then did I start building. That’s business validation in action. Presales and cash collected are the only proof that matters. Marketplace Platforms: Goldmines for Idea Testing Platforms like Craigslist, Etsy, and Facebook Marketplace aren’t just for shopping—they’re treasure troves for finding unmet needs. I call this “problem mining.” Scroll through listings, read what people are asking for, and notice what’s missing. Post your own offers and see if anyone bites. These platforms let you test your idea with real buyers, not just friends and family. Marketplace validation de-risks the build phase—you’re not guessing, you’re getting direct feedback (and hopefully, cash). Why Three Paying Strangers Beat 50 Likes from Friends Here’s a harsh but necessary truth: feedback from friends and family doesn’t count. They love you, or at least like you enough to spare your feelings. But strangers? They’re honest with their wallets. If you can convince three people who don’t know you to pay for your offer, you’ve got green shoots. If not, don’t waste time—pivot, iterate, and test again. As I say in the book: “If you can find three paying customers in forty-eight hours, you’ve proven the concept. If not, iterate and try again.” – Noah Kagan Failure as Fertilizer: Pivot Without Mercy Think of every failed attempt as fertilizer for your next idea. If your first pitch flops, don’t take it personally—take it as data. Maybe your offer needs tweaking. Maybe your audience isn’t right. The key is to pivot quickly, not to get stuck in analysis paralysis. The faster you can move from “no” to “next,” the sooner you’ll find what works. The Grandma Test: Would She Pay for It? Here’s a wild card I use: imagine pitching your half-baked idea to your grandma. Would she pull out her wallet? If not, why would a stranger? This mental check keeps you honest and focused on real value, not wishful thinking. Golden Rule of Validation: Sell to three strangers before moving on. Customer-First beats Founder-First every time. Marketplace validation de-risks your launch. Harsh but true: Friend feedback doesn’t count. Pivot quickly if validation fails; iterate and test again. Business validation isn’t about perfection—it’s about action, speed, and listening to your customers. The Golden Rule of Validation is your shortcut to building something people actually want. Validate ideas with real customers, collect feedback, and let the market guide your next move. That’s how you turn a scribble into a seven-figure business, one paying customer at a time.From Jerky Snafus to Seven Figures: The Power of Tiny Tweaks and Past Failures Let’s get real: no business—no matter how shiny it looks from the outside—was born fully formed. Every seven-figure story I’ve lived or witnessed started with a mess of pivots, “faceplants,” and rejections. The myth that you need a perfect plan, a fancy website, or a pile of cash to get started? Toss it. The real secret is learning to love the feedback that comes from failure, and using tiny tweaks to transform setbacks into breakthroughs. That’s the heart of Million Dollar Weekend: practical steps, business validation, and minimal investment—over and over again. Case Study: How Sumo Jerky Hit $1,000 Profit in 24 Hours Let’s talk about one of my favorite “snafus-to-success” stories: Sumo Jerky. I started out selling beef jerky subscriptions to individuals, hustling for every single sale. It was slow, frustrating, and honestly, not working. But instead of giving up, I took a step back and asked, “What’s one bold tweak I haven’t tried?” That’s when I flipped the model—targeting offices instead of individuals and offering corporate subscriptions. Here’s the kicker: I didn’t build a new website or invest in fancy tech. I made a simple “Dream Ten” list of companies I wanted as customers, sent out personalized emails, and used PayPal to collect payments. Within 24 hours, Sumo Jerky made $1,000 in profit. That’s the power of minimal investment and validating ideas with real sales, not just hope. “Small pivots can turn failure into gold.” – Noah Kagan Actionable Advice: Use What You Already Have Most aspiring entrepreneurs get stuck thinking they need a custom app, a slick website, or a big advertising budget. The truth? You probably already have everything you need to get started: Email – Reach out to potential customers directly. Phone – Call your “Dream Ten” prospects and pitch your offer. Google Sheets – Track orders, feedback, and revenue. PayPal or Venmo – Collect payments instantly. Forget the tech until you have proven cashflow. The first step is to validate your idea with real customers and real money. Dream Ten: Make a Hit-List, Not a Website One of the most effective business validation tactics I teach in Million Dollar Weekend is the “Dream Ten” prospect list. Instead of spending weeks building a website, make a list of ten ideal customers. Then, reach out to them directly with a simple, actionable script. For Sumo Jerky, this meant emailing office managers and offering a trial subscription. For your side hustle, it could mean DMing local businesses or messaging LinkedIn contacts. Hypothetical: The Gourmet Pencil Experiment Imagine you try to sell “Gourmet Pencils for Chefs.” You reach out to 25 prospects and get 25 rejections. Most people would call it a failure. But here’s the twist: every “no” is a data point. Maybe chefs don’t want pencils—but they’re desperate for custom notepads or recipe journals. That feedback is your goldmine. The next iteration, shaped by real-world feedback, is often the one that takes off. Why Most Entrepreneurs Are One Bold Tweak Away from a Breakthrough The difference between a flop and a seven-figure business is often just one bold tweak. The Sumo Jerky pivot to corporate subscriptions, validated with nothing but PayPal and email, is proof. Minimal investment and relentless iteration are your best friends. Every rejection, every failed experiment, is a step closer to the version of your business that works. So, leverage connections, embrace feedback, and keep your tools simple. The actionable advice in Million Dollar Weekend is clear: validate ideas fast, use what you have, and never be afraid to pivot. Your first $1,000—or $1,000,000—could be just one tweak away.Experiment-Based Marketing: Becoming Your Own Growth Machine If you want to build a business that grows fast—without waiting for the “perfect” plan or a big ad budget—let me introduce you to experiment-based marketing. This is the secret sauce behind every wild success I’ve had, from launching AppSumo to helping Mint.com rocket to 1 million users in just six months. The idea is simple but powerful: treat every marketing move as a mini-experiment. Run them small, run them often, and let real customer results—not your ego—decide what happens next. Why Experiment-Based Marketing Works Most people get stuck in “planning mode,” obsessing over logos, websites, or social media likes (the ultimate vanity metrics). But those things don’t pay the bills. What matters is what your fans actually buy, use, and share. Experiment-based marketing flips the script: you test ideas in the real world, learn fast, and double down on what works. It’s the ultimate growth machine—and anyone can use it. “The key to growth is relentless focus on your actual customers.” – Noah Kagan How to Run Micro-Experiments (And Why Small is Smart) Here’s how I do it: every new marketing idea is a micro-experiment. That means: Start with a simple hypothesis (“If I email 10 personal finance bloggers, will one feature my product?”) Run the test fast—no waiting, no overthinking Measure only what matters (signups, sales, replies—not likes or impressions) Double down on the winners, ditch or tweak the losers This approach is how Mint.com went from zero to 1 million users in six months. We didn’t have a huge ad budget. Instead, we ran dozens of micro-experiments: guest posts, blogger outreach, giveaways, and more. The winning move? Targeting personal finance bloggers with tailored pitches. That single experiment unlocked a tidal wave of users. Case Study: Sumo.com’s Billion-Impression Blitz With Sumo.com, we hit 1 billion impressions in just 12 months. How? By running rapid-fire experiments: testing new content formats, swapping headlines, and always asking, “What’s one thing we can do today to get more people to try us?” We didn’t obsess over getting featured on TechCrunch or hitting #1 on Product Hunt. We focused on what our actual customers cared about—and let the numbers guide us. SendFox: 10,000 Customers in Six Months (Powered by Follow-Up) Here’s a practical step you can steal: relentless follow-up. When we launched SendFox.com, we didn’t have a fancy website—just a Google Doc and a way to collect emails. Our secret weapon? Follow-up emails. Nearly 50% of AppSumo’s sales come from follow-up, not splashy launches. With SendFox, every new lead got a personal email, a quick check-in, and a simple question: “What would make this tool twice as useful for you?” That’s how we hit 10,000 customers in six months—by listening, iterating, and following up like crazy. Practical Steps: Your Growth Machine Playbook Pick one idea (a new email, a landing page, a cold outreach script) Test it small (send to 10 people, not 10,000) Measure real results (did anyone buy, reply, or sign up?) Follow up—half the battle is in the chase, not the first ask Iterate fast—tweak, retest, and repeat You don’t need a big ad spend or a designer. Anyone with a Gmail account and a story can win this game—even if your first landing page is a Google Doc. The Million Dollar Weekend approach is about action, not perfection. Your growth machine is built on experiments, customer-centric thinking, and the courage to follow up. 1000 True Fans and the Secret Sauce of Community If you want to build a business that lasts, forget about chasing millions of followers or viral fame. The real growth machine—the secret sauce behind every cult brand and sustainable business—is the 1000 True Fans principle. This idea, made famous by Kevin Kelly and echoed by Seth Godin’s “smallest viable audience,” is simple: you don’t need everyone. You just need a core group of people who love what you do, buy what you offer, and tell their friends about you. That’s how I built AppSumo, Sumo, and every business I’ve launched since. It’s also the heart of Million Dollar Weekend. Start Small: Obsess Over Your First 10, Then 100 Here’s the truth: building a cult brand starts with deep care for the first 1, 10, or 100 people. Ignore the masses at first. When I launched AppSumo, I personally emailed every early customer, asked for feedback, and made sure they felt like insiders. That’s how you create real engagement—not by blasting ads, but by building relationships. Your first fans are your foundation. Treat them like gold, and they’ll become your best marketers. The 1,000 True Fans Playbook: Give, Give, Give Community building for entrepreneurs isn’t about taking—it’s about giving. The 1,000 True Fans principle is a playbook of relentless generosity: Share your best ideas and resources for free. Answer questions, even if they don’t buy (yet). Feature your fans, celebrate their wins, and make them feel seen. When you give, you build trust. When you build trust, people buy—and shout your name from the rooftops. That’s how you turn casual followers into true fans. Platform Picking 101: Go Where Your Fans Hang Out Don’t waste time on every platform. Pick the one where your audience actually spends time—and where your strengths shine. Whether it’s Twitter threads, YouTube walkthroughs, LinkedIn posts, or TikTok rants, pick your lane and go all-in. That’s how Danny Wang went from small-time designer to 2.3 million TikTok followers. He focused narrowly on design tips, delivered massive value, and built out from there. His story proves that niching down and growing outward is the winning formula for community building. Email List: The Audience You Own (and Monetize) “Your email list is the heart of profits and the only audience you truly own.” – Noah Kagan Here’s a fact: half of AppSumo’s $65 million in revenue came from email, not social algorithms. Social media is great for discovery, but your email list is the one audience you own. Ownership equals cashflow. Algorithms change, platforms die, but your list is yours forever. That’s why building an email list is the most actionable advice I can give any entrepreneur. Use tools like SendFox, Mailchimp, or ConvertKit. Offer a lead magnet, tell your story, and nurture every new subscriber with real value. Segment, personalize, and follow up—this is how you turn subscribers into superfans. Templates, Storytelling, and Community Loops Real community building isn’t about a tall follower count—it’s about relationships. Use templates to save time, but always add your personal touch. Share stories, not just sales pitches. Create community loops: invite feedback, highlight customer stories, and encourage your fans to connect with each other. That’s how you build a growth machine that runs on loyalty, not luck. Nick Huber (The Sweaty Startup) grew by niching down and serving a tight community. Matt Taibbi left Rolling Stone, owned his audience on Substack, and built a thriving business. Danny Wang’s TikTok proves that focus and generosity win, even in crowded markets. True influence—and income—comes from community, not just numbers. Focus on your 1,000 True Fans, own your email list, and build a brand that people love to talk about. That’s the real growth hack behind Million Dollar Weekend.Don’t Just Work—Design Your Life (Colorful Calendars, Accountability, Messy Wins) “Sustaining growth and joy means running your business and life by design, not default.” That’s not just a catchy line—it’s the backbone of the Million Dollar Weekend guide. If you want to build a business that lasts (and a life you actually enjoy living), you have to work smart, stay disciplined, and put intentional systems in place. Your business is only as healthy as your habits. Design beats default every single time. Let me get real for a second: my color-coded calendar isn’t (just) for show. It’s my real-life blueprint. Every block of color—work, health, relationships, travel, even “do nothing” time—reminds me that I’m not just building a business, I’m designing a life. When I first started out, I was all hustle, no structure. I’d grind for hours, burn out, and wonder why I wasn’t making progress. The turning point? Treating my calendar like a living, breathing system. I use bright colors for work sprints, calm blues for workouts, and gold for personal time. It’s simple, but it keeps my priorities visible and actionable every single day. This is practical, actionable advice you can use right now: color-code your calendar and watch your focus (and fun) skyrocket. But systems aren’t just about pretty schedules—they’re about resilience. Enter the Law of 100. Here’s the deal: before you judge whether something is working, commit to trying it 100 times. That’s how I built AppSumo, Sumo Jerky, and every other venture. Most people quit after the first “no,” the first flop, or the first awkward sales call. But if you make 100 asks, send 100 emails, or pitch 100 prospects, you’ll learn more (and win more) than you ever imagined. The Law of 100 is the ultimate work smart hack: commit first, analyze later. It’s messy, it’s humbling, and it’s where real growth happens. Of course, you can’t do it alone. Find your accountability buddy—mine’s Adam. We check in weekly, share our goals, and call each other out when we’re slacking. Don’t try to hustle in a vacuum. Community building isn’t just a buzzword; it’s your secret weapon. Whether it’s a mastermind group, a Slack channel, or a simple text thread, surrounding yourself with people who want to see you win changes everything. They’ll keep you honest, energized, and moving forward when motivation dips. Another game-changer: the Dream Year brainstorm. Every quarter, I map out my goals for work, play, and impact. What do I want to build? Where do I want to travel? Who do I want to help? This isn’t just wishful thinking—it’s a practical step that keeps me weirdly energized and focused. When you write down your goals and share them with your circle, you’re far more likely to make them real. Try it: grab a notebook, sketch out your Dream Year, and watch how your daily decisions start to align with your bigger vision. And here’s a wild card: what if you treated your weekly review like a halftime pep talk instead of a guilt trip? Every Sunday, I look back at my wins, my flops, and my “almosts.” I celebrate the messy victories, learn from the losses, and reset for the week ahead. This simple routine builds durability and fun into entrepreneurship. It’s not about perfection—it’s about progress. Bottom line: designing your life for joy and growth is as vital as designing your offer. The Million Dollar Weekend guide isn’t just about business tactics—it’s about building a system that lets you thrive, not just survive. So color-code your calendar, commit to the Law of 100, find your accountability circle, and dream big. Work smart, stay disciplined, and remember: messy wins beat perfect plans every time. If I can do it, so can you. Let’s design a life—and a business—you’re proud of, starting this weekend.TL;DR: Million Dollar Weekend is a no-BS field guide to starting—and scaling—a business, built on action-first mindset, rapid validation, and real-world community, all in just 48 hours. No magic, just momentum. You’ll learn to silence doubt, embrace failure, and turn coffee chats into cash.

AS

A Sheraz

Nov 29, 2025 23 Minutes Read

Million Dollar Weekend: Building a Business (and a Life) in 48 Wild Hours Cover
Stop Chasing Focus: ADHD Productivity Hacks That Actually Work (From a Former Scatterbrain CEO) Cover

Nov 2, 2025

Stop Chasing Focus: ADHD Productivity Hacks That Actually Work (From a Former Scatterbrain CEO)

I used to be the perpetually distracted guy—the one who’d check email before breakfast, start five projects before lunch, and end up doomscrolling social media when I needed to be working. Not exactly the image of a hyper-focused CEO, right? The turning point: the day I realized the best in the world weren’t muscling through distractions—they were hacking their brains. If you’re sick of losing battles with your own mind (or just want a few unfair focus advantages), you’re in the right place. Here’s what actually worked for me (and no, it’s not just about bullet journaling or lighting candles). 1. The Anti-Todo Revolution: Why Cutting Out Tasks (and Toxic People) Is the Start of Real Focus Let’s flip the script on productivity. If you’re like me—ADHD, easily distracted, and tired of fighting your brain—here’s the truth: the most productive people don’t muscle their way through endless to-do lists. They use ADHD productivity hacks that start with subtraction, not addition. The first and most powerful hack? Creating a Not-To-Do List. Why a Not-To-Do List Beats a To-Do List Focus isn’t a muscle you build by piling on more tasks. Focus is a filter. The more you cut, the clearer your path. Every new “yes” is a “no” to your dreams. I live by this: "You don't do more to win, you do less, but you make the things you say no to, the right yeses." The Plinko Effect: Visualizing Your Energy Picture the game Plinko: you drop a ball, and it bounces off dozens of pins, landing somewhere random. That’s how most people live—scattering energy across distractions. But if you remove those pins (distractions, tasks, toxic people), your energy shoots straight to what matters. Prioritizing tasks becomes effortless when you subtract the noise. What Goes on My Not-To-Do List? Low-value tasks: If I can pay someone else or automate it, it’s gone. Outsourcing and routine elimination are game-changers. Bad habits and vices: For me, late-night gaming was a killer. I’d stay up, then drag through the next day. Cutting it out gave me back hours of focus. Energy vampires: Some people (and activities) drain your creative energy. If someone leaves you feeling depleted, they’re off my calendar. Research backs this up: Subtracting just 3-5 persistent distractions can increase your daily focused time by up to two hours. Eliminating energy vampires and time-wasters isn’t just about productivity—it’s about protecting your mental bandwidth. Saying No Is a Skill Here’s my unpopular opinion: saying no is the real productivity superpower. It’s not easy, but your focus depends on it. Every “no” to a low-value task or toxic person is a “yes” to your biggest goals. Start your own not-to-do list today, and watch your focus sharpen.2. Tricking Your Brain into Flow: Rituals, Environments, and Built-In Triggers Here’s the truth: focus isn’t a muscle you flex—it’s a filter you set. If you’re like me (a former scatterbrain CEO), waiting for inspiration to strike is a recipe for endless distraction. Instead, I learned to create focus triggers—deliberate cues that help me slip into Finding Your Flow on demand. As I always say, "See, flow state isn't random, it's designed." My Unexpected Toolkit for Deep Work Blocks Location: I have a specific chair for reading and brainstorming. When I sit there, my brain knows it’s time for Deep Work Blocks. Even quarterly planning offsites with my wife have become rituals—those locations are triggers for designing our future, not worrying about the day-to-day. Sound: Headphones are my armor. I use playlists with no lyrics or binaural beats (yes, the science-y stuff!) to anchor my attention. The ‘focus playlist’ experiment? For me, binaural beats + headphones = productivity magic. Routine: If it’s not in my calendar, it doesn’t exist. I block 60–120 minute sessions—my prime time for deep work. World-class athletes rehearse routines before every game. Why shouldn’t we? My mornings start with the same sequence: coffee, headphones, and a closed door. That’s my signal to my brain: it’s go time. Visual Cues: A closed door, a ‘do not disturb’ sign, or just visible headphones signal to others (and myself) that I’m in a Building Distraction-Free Environment. Personal Routines for Focus: Why Routine Isn’t Boring People think routine is dull. But you know what’s really boring? Never finishing anything because you’re constantly distracted. Routine is the rhythm of success. Research backs this up: establishing three or more unique focus triggers (location, sound, routine, visual cues) correlates with higher self-reported productivity. Multiple sensory cues—where you sit, what you hear, and what you do—prime your brain for flow. My advice: design your environment so that deep work becomes automatic. Don’t wait for focus to find you. Build your own triggers and watch your productivity soar. 3. Build Your Focus Fortress: How to Be (Strategically) Hard to Reach and Manage Distractions Let me take you back to the most productive week of my life: editing my book in a WiFi-free mountain cabin with my friend Chris. No notifications, no inbox, no distractions—just 16 hours a day of deep work, for five days straight. We finished the book. That experience taught me the power of building a true distraction-free environment and being intentionally hard to reach. Be Accessible Online, But Hard to Interrupt Personally Here’s the truth: most of us make it way too easy for others to interrupt us. The constant ping of notifications, the endless stream of emails—these are productivity killers. I live by this rule: be easy to find online, but hard to reach in real time. My phone only allows notifications from two people: my wife and my assistant. Everyone else can wait. Turn off all notifications. Go into your app settings and swipe them off. Seriously, try it. You’ll be amazed at how much mental space you reclaim. Restrict channels of interruption. The fewer ways people can reach you instantly, the more deep work you’ll get done. Batch Your Communications for Maximum Focus Your inbox? It’s just a “Your inbox is nothing more than a public to-do list of other people's priorities on your time.” Instead of letting it dictate your day, batch your responses. I schedule dedicated 60-minute windows to reply to texts and emails—sometimes while relaxing in the hot tub. This is a powerful time management technique that turns communication from a distraction into a productivity tool. Use Visual Signals and Environmental Cues Headphones = Do Not Disturb. When I put on my headphones, everyone knows not to interrupt unless it’s urgent. Closed door rules. My family knows that a closed office door means “focus mode”—unless it’s an emergency, they wait. Change Your Environment to Suppress Interruptions Sometimes, the best way to manage distractions is to physically remove yourself. Work from a coffee shop or another quiet space. Here’s an advanced move: leave your power cable at home. With only your laptop battery, you’ll be forced to focus and finish before the juice runs out. Managing distractions isn’t about willpower—it’s about building systems and environments that protect your focus. Try these strategies and watch your productivity soar.4. Turn Up the Pressure—But on Your Own Terms: Using Urgency and Gamification to Outwit Your Inner Procrastinator If you have ADHD (or just a wandering mind), you know how easy it is to let tasks stretch out forever. Here’s the truth: Parkinson’s Law Productivity is real. As the saying goes, "There's this thing called Parkinson's law that states the work will expand to the available time given to it." If you give yourself three months to move out, you’ll pack slowly, get distracted, and procrastinate. But if you only have three days? Suddenly, you’re laser-focused and unstoppable. That’s the power of a Sense of Urgency. Shorten the Timeline, Raise the Stakes Artificial deadlines are my secret weapon. When my team says, “I’ll get it to you by the end of the week,” I push back: “Why not by 3 p.m.?” Shorter timelines force creativity and focus. But urgency alone isn’t enough—you need real consequences. I once had a team member, Jen, who wanted to lose weight. She made it public, and we set a non-negotiable: if she didn’t hit her goal by the deadline, her job was on the line. The stakes were real, and her focus followed. Gamifying Work Motivation: Make Progress Visible Here’s another ADHD Productivity Hack: Gamify your work. Video games are addictive because you see your progress—levels, streaks, XP bars. I track my writing sessions like XP points. Every finished draft is a “level up.” When you can see your progress, you’re less likely to get bored or distracted. Immediate Rewards—like checking off a to-do, hitting a streak, or moving a progress bar—keep your dopamine (and motivation) high. Break big tasks into “levels” or milestones Track streaks for daily habits Use visible progress bars or checklists Celebrate small wins—don’t wait for the finish line Research shows time constraints enhance focus and creativity. Gamification increases dopamine and keeps you motivated. If you can’t see your progress, your brain gets bored and wanders. Design visible, trackable wins to keep your attention locked in. Data Point Insight Refocus time after distraction 23 minutes average (per research) Public commitment to team Job at stake for missing goal Gamified work Adding 'levels' increases task completion rates Conclusion: Not-So-Obvious Truths About Focus—And the Real Source of Productivity If you’ve made it this far, you already know this isn’t your typical list of ADHD productivity hacks or generic focus strategies for ADHD. Here’s the not-so-obvious truth: Stop trying to brute force yourself into focus. The real game-changer isn’t more willpower—it’s about hacking your context and environment until they work for you, not against you. For years, I thought my problem was distraction. I’d blame boredom or lack of discipline. But the real reason I drifted off task? I couldn’t see my progress. When you can’t see the finish line (or even the next step), your brain goes hunting for something easier, shinier, or just less frustrating. That’s why managing distractions is less about ironclad self-control and more about making your progress visible and your environment frictionless. Here’s what actually works: Success is a subtractive game. Most of us try to add more—more apps, more routines, more rules. But the magic happens when you start cutting out what doesn’t serve you. For example, I bought a new chair just for my “hard tasks.” Now, it’s the only spot I write from. No emails, no scrolling—just deep work. It’s a tiny shift in context, but it’s changed everything about my workflow. That chair is my productivity hack, and it’s weirdly sacred now. Perfection is a myth, especially with ADHD. The real win is consistently showing up and stacking small victories. Some days, that means writing one paragraph. Other days, it’s just opening the document. What matters is the ritual, not the outcome. Experiment with your rituals—personalize, tinker, and keep what works (and toss the rest). If something feels forced or makes you miserable, ditch it. Your best focus strategies for ADHD are the ones you invent for yourself. And let’s not forget: saying “no” is a radical productivity strategy. Seriously. Every time you cut out a commitment, a distraction, or a tool that doesn’t fit, you’re making space for what matters. That’s the real source of productivity—not more effort, but better choices. So, stop chasing focus and start designing your environment. Your brain (and your to-do list) will thank you.TL;DR: Productivity isn’t about relentless self-discipline—it’s about clever systems that fit your brain. My top hacks: ruthlessly curate your 'not-to-do' list, set up focus triggers, make yourself hard to reach, lean into pressure, and gamify your progress. ADHD or not, use these strategies to get out of your own way and achieve real, meaningful output.

10 Minutes Read

Speak Like a Leader: The Strange Art of Saying Less and Earning More Respect Cover

Nov 2, 2025

Speak Like a Leader: The Strange Art of Saying Less and Earning More Respect

I’ve lost count of the meetings where I watched brilliant people talk themselves in circles, their best ideas buried under a mountain of I think’s and just a thought’s. Early in my career, this was me—the queen of qualifiers. But here’s the twist: the real power in leadership communication isn’t about talking more or louder. It’s about wielding words with precision. Picture this: my first time firing someone, nervously over-explaining until even I wasn’t sure what I meant. (Spoiler: I bumbled it. But I learned fast!) Let’s unravel the unexpected skills that make confident leaders sound, well, like leaders—and not apologetic weather forecasters. 1. Say It Like You Mean It: From Uncertain to Unstoppable Confident Communication is the foundation of effective Leadership Communication. Over the years, working under—and eventually becoming—an executive, I’ve learned that the way you speak shapes how people see you. The most respected leaders in any room aren’t necessarily the ones with the fanciest titles, but those whose words match their ambition. If you want to be seen as powerful, respected, and confident, you have to say it like you mean it. Stop Speaking Just to Be Liked—Speak to Lead Early in my career, I made the classic mistake of trying to please everyone in meetings. I’d soften my input, add qualifiers, and hope to blend in. But I noticed something: the people who got listened to, the ones who influenced decisions, didn’t speak to be liked. They spoke to lead. They owned their opinions, even if they weren’t in charge—yet. “The mindset shift that the people who are successful have is: I am a leader, even if they aren't yet.” In my current company of over 250 team members, I see this play out every day. Those who act like leaders—who communicate with certainty—stand out. Those who hedge, apologize, or shrink their words, unintentionally erode their own credibility. Leadership Style isn’t about waiting for a title; it’s about how you show up and speak up, right now. Ditch the Qualifiers: Speak with Certainty One of the simplest, most powerful Communication Skills I’ve learned is to remove unnecessary qualifiers from my language. Phrases like “I think” or “I feel” may sound polite, but they actually undermine your authority. When you say, “I think we should try this,” you’re signaling uncertainty. Swap it for, “The best path forward is…” and watch how the room responds differently. Instead of: I think we should try this. Say: The best path forward is… Instead of: I feel like this might work. Say: Here’s the strategy that will get us this result. These language tweaks may seem small, but they make a huge difference. When you speak with clarity and certainty, you project authority. Clear Communication is a hallmark of effective leadership. People naturally gravitate toward those who sound sure of themselves. Own Your Perspective—Every Leader’s View Is Valid Top executives and CEOs don’t wait for permission to have a point of view. They use their experience and perspective to frame their communication. Even if you’re not the most senior person in the room, your perspective is valid. You’re there for a reason. When you own your view and share it with confidence, you build credibility and authority. Remember: Confident Communication isn’t about being the loudest voice. It’s about being the clearest, most certain one. Practice these language swaps, adopt a leader’s mindset, and you’ll move from uncertain to unstoppable—no matter your current title.2. Out-Logic Your Emotions (or: The Blade of Grass Principle) Let’s be honest: emotions are powerful, but unchecked, they can sabotage your Leadership Communication. I’ve seen it time and again—when someone lets their emotions take the wheel, their words come out reactive and unsure. Around here, we have a saying: high emotion, low intelligence. It’s blunt, but it’s true. When you’re in emotional overdrive, your logic takes a back seat, and that’s when your message—and your credibility—start to unravel. Think about the people you know who are always venting, dramatizing, or spinning stories about what’s wrong. They rarely have a circle of winners around them. Their business relationships struggle, and their teams don’t thrive. Why? Because when emotion clouds your decisions, you lose the clarity and composure that Effective Leadership demands. Reactivity erodes trust; composure under pressure inspires confidence. “Never let your emotions override your message.” Adaptability: The Blade of Grass Principle Here’s a visual that changed the way I handle tense moments: I imagine myself as a blade of grass. Picture this—a rock falls onto a blade of grass. The grass bends, flexes, and then springs back up. Now, imagine that same rock hitting a toothpick. The toothpick snaps. The difference? Adaptability. In Leadership Communication, you want to be the grass, not the toothpick. When criticism or chaos hits, don’t stiffen up and break. Instead, absorb the pressure, let it pass through, and return to your steady self. Blade of grass: Flexible, absorbs pressure, returns to form—demonstrates adaptability and resilience. Toothpick: Rigid, snaps under stress—symbolizes brittle, reactive leadership. Respond with Data and Grace, Not Outbursts Effective Leadership means letting emotions pass through you, not letting them dictate your response. When someone comes at you with an emotional outburst, don’t match their intensity. Instead, listen, let their words flow past, and respond with logic and empathy. Use data, ask questions, and stay composed. This approach not only keeps your message clear, but it also builds trust. People follow leaders who are steady, not those who are swept away by every emotional wave. Just this week, I witnessed someone lose control in a meeting—an emotional outburst that instantly lowered my confidence in them. Their inability to handle rejection or criticism with grace revealed a pattern: decisions driven by emotion, not logic. Over time, this erodes confidence and undermines leadership. Remember, you can’t be a leader if people don’t trust and follow you. Empathy and Emotional Self-Management Empathy isn’t about absorbing everyone’s emotions and reacting in kind—it’s about understanding, then responding with intention. Emotional self-management is essential. When you let emotions pass through you, you create space for logic and clarity. That’s how you earn respect and maintain authority, especially in high-pressure situations. Emotional overdrive signals uncertainty—leaders channel logic instead. Visualize yourself as a flexible blade of grass, not a brittle toothpick, when criticism or chaos hits. Let emotions pass through you, respond with data and grace, not outbursts. In short, adaptability, empathy, and composure are the hallmarks of Effective Leadership. Out-logic your emotions, and you’ll find your words carry more weight—and your team’s confidence in you will soar.3. Stop Monologuing: The Subtle Power of Question Masters When I first started leading teams, I thought authority meant having all the answers. I quickly learned that the real power in leadership communication comes from asking the right questions—not delivering endless monologues. The best leaders aren’t answer-machines; they’re expert untanglers, using open-ended questions to uncover what truly matters and to draw out the wisdom of their teams. Great leaders speak with weight, not with volume. Every time you enter a conversation, ask yourself: What impact do I want to make here? If there’s no clear reason for you to be in the room, it’s better to leave than to fill the air with empty words. When you do participate, show up with intention. Your time—and your voice—should be spent where it matters most. Why Questions Trump Answers in Leadership Communication It’s a myth that leaders must always know what to do. In fact, “The best leaders think of themselves as professional problem solvers, and the reason they're able to solve these problems better... is simply because they ask more questions.” Open-ended, targeted questions are the secret weapon. They deepen understanding, reveal hidden obstacles, and invite genuine feedback from your team. This is the heart of active listening—not just hearing, but truly understanding. Open-Ended Questions encourage participation and richer feedback. Active Listening builds trust and empathy, strengthening team rapport. Strategic questions guide conversations, helping you identify the real issues. From Awkward to Artful: My ‘Question Game’ Story My earliest lesson in communication skills came from a childhood ritual my parents called the “question game.” At family gatherings, my mom would nudge me toward an adult—let’s call him Mr. Bob—and challenge me to ask him three questions. Terrifying? Absolutely. But it forced me to keep the conversation alive, even when I ran out of things to say. If I stalled after one or two questions, my mom would coach me with new ideas and send me back for another try. This awkward practice taught me something priceless: the art of curiosity. It’s not about dazzling people with knowledge—it’s about drawing them out, making them feel heard, and uncovering what’s really going on beneath the surface. As a leader, this skill is invaluable. The more you practice, the easier it becomes to move beyond timid, yes/no questions and into meaningful dialogue. Ask Better, Lead Better: Practical Questioning Tips Replace “How’s it going?” with “What’s the biggest challenge you’re facing right now?” Swap “Can we fix this?” for “What would it take to ensure this never happens again?” Instead of “What do you think?” try “What data supports this decision?” Remember: the quality of your questions determines the quality of your results. Don’t settle for surface-level answers. Strategic, open-ended questions plant you at the helm of the conversation—and the team. Curiosity, not expertise, is what sets true leaders apart.4. The Silent Mic Drop: Why Saying Less Makes You Sound Like a Boss Let’s talk about one of the most overlooked secrets of leadership communication: the power of saying less. Early in my career, I learned this lesson the hard way. I was 23, sitting across from someone I had to let go. I’d been coached to deliver a clear, direct message—no debate, no drawn-out explanations. But when the moment came, nerves took over. Instead of sticking to the plan, I started oversharing. I told them how wonderful they were, how much I enjoyed working with them, and how difficult this was for me. The more I talked, the more tense and uncomfortable I became. I kept circling, never landing, and instead of a decisive conversation, we just had a painfully awkward chat. I had to try again the next week. It was embarrassing—and it taught me everything I needed to know about clear communication and authority in meetings. Here’s the truth: oversharing reeks of insecurity. When you overexplain, you’re not just filling the silence—you’re signaling to everyone in the room that you’re not confident in your message. As I learned that day, “Overexplaining is an indicator that you are not confident.” The most effective leaders don’t ramble. They don’t soften their feedback with endless qualifiers or seek validation with nervous add-ons. Instead, they replace overexplaining with firm, respectful statements that maintain control, even in tough discussions. This is especially important when the stakes are high. Whether you’re giving feedback, making a tough decision, or leading a meeting, leadership communication is about landing your point and letting it stand. Think of it like an airplane coming in to land: you want to touch down smoothly and decisively. But we’ve all been in meetings where someone keeps circling—repeating themselves, adding new angles, never quite finishing. It’s exhausting for listeners. This kind of verbal “takeoff, circle, never land” routine creates listener fatigue and erodes your authority. Transparency and clarity are vital for effective leadership. When you speak with confidence and brevity, you show respect for your audience’s time and intelligence. You also leave no room for confusion or nervous rambling. The best communicators—think of high-level CEOs—are direct and deliberate. They don’t seek validation from the room; they deliver their message with grace and move on. That’s how you earn respect and establish authority in meetings. In the end, communication skills aren’t just about what you say—they’re about what you choose not to say. The silent mic drop is real. When you know what needs to be said, say it clearly, say it kindly, and then stop. Let your words land. That’s how you speak like a leader—and that’s how you earn more respect by saying less.TL;DR: Cut the fluff, keep your cool, ask sharper questions, and always say less than you’re tempted to—real leadership communication is about substance, not show.

11 Minutes Read