Welcome to A Smart Bear: Longform

Articles from building two unicorns over two decades; one bootstrapped, one funded.

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  The roadmap to Product/Market Fit (PMF)… maybe

  This eight-step process brought WP Engine from an idea to a Unicorn. While there are other roads to Product/Market Fit, consider copying some of these ideas. —December 2023 | 6,500 words.
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  Rich vs. King in the Real World: Why I sold my company

  Reflecting on selling Smart Bear in 2007, offering insights for entrepreneurs facing similar decisions. —October 2009 | 1,600 words.
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  Extreme brainstorming questions to trigger new, better ideas

  We know, “no idea is a bad idea,” but brainstorming is often unsuccessful. These prompts actually work. They could even lead to a unique business model. —March 2022 | 3,700 words.
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  Excuse me, is there a problem?

  Many startups fail despite identifying a real problem and building a product that solves that problem. This explains why, so you can avoid their fate. —April 2023 | 6,800 words.
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  Your customers hate MVPs. Make a SLC instead.

  “MVP” implies a selfish process, abusing customers so you can “learn”. Instead, make the first version SLC: Simple, Lovable, and Complete". —August 2017 | 2,200 words.
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  The Elephant in the room: The myth of exponential hypergrowth

  Even Facebook and Slack did not grow “exponentially,” as frequently described. Here is the correct model that you can use to understand and affect growth. —March 2022 | 5,600 words.
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  Stubborn Visionaries & Pigheaded Fools

  How do you know when to stop, versus when to push through? You don’t, not even in hindsight. But these guiding questions can help. —March 2024 | 1,200 words.
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  How repositioning a product allows you to 8x its price

  You can charge much more than you think, if you reposition your value-proposition. Here’s how. —June 2018 | 700 words.
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  Fermi ROI: Fixing the ROI rubric

  Traditional rubrics fail to reveal the best answers, or how to explain those answers to others. After explaining why, the following system solves both failures. —June 2022 | 4,700 words.
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  Navigating the unpredictability of everything

  We dramatically, repeatedly fail to predict the future. Does that mean “strategy” is senseless? No, it means you need these techniques to navigate a volatile world. —March 2023 | 4,900 words.
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  Rocks, Pebbles, Sand: How to implement in practice

  This complete work-prioritization framework builds on the simplistic “Rocks, Pebbles, Sand” analogy, adding the details you need in the real world. —July 2022 | 4,000 words.
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  The Iterative-Hypothesis customer development method

  A simple but effective system, used to vet what is now a Unicorn, for generating insights about how your potential customers think, what they need, and what they’ll buy. —September 2022 | 4,200 words.
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  Using the Needs Stack for competitive strategy

  This simple method positions your product to be more valuable, especially against competitors who aim to disrupt you, or you them. —June 2023 | 3,800 words.
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  Willingness-to-pay: Creating permanent competitive advantage for the right reasons

  This fresh take on “Willingness-to-Pay” analyzes three types of customer motivation, leading to superior strategies for growth that also better the world. —May 2023 | 4,000 words.
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  How startups beat incumbents

  A startup can beat a large, successful incumbent, if it does things the incumbent can not or will not do. Here are those things. —February 2024 | 4,800 words.
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  Selling to Carol: Why targeting an ICP brings 10x more customers than you expected

  Targeting your “Ideal Customer Profile” (ICP) is the best way to differentiate and win sales, but does it limit your target market? —January 2024 | 2,800 words.
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  Product/Market Fit (PMF): Experience & Data

  Companies that achieve Product/Market Fit – both self-funded and VC-funded – exhibit the same prototypical metrics curves and subjective experiences. —November 2023 | 2,400 words.
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  How annual pre-pay creates an infinite marketing budget

  Dozens of founders have used this technique to transform the cash-flow of their businesses. Now it’s your turn. —July 2024 | 2,500 words.
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  Profitable on day one!

  You’re not profitable if you couldn’t afford someone else to do your job. $1000/mo isn’t profitable. Fix your definition of “profitable,” and build a truly profitable business. —August 2024 | 900 words.
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  Avoid blundering: 80% of a winning strategy

  Why do startups typically fail? It turns out that “avoiding those things” is already a plan for success. —March 2024 | 4,000 words.
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  Finding Fulfillment

  What creates a fulfilling existence? Exploration leads to a framework I’ve used for years for myself and the people around me. I hope it helps you too. —December 2022 | 2,800 words.
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  In command

  Being “in control” is impossible, perhaps not even desirable. Being “in command” is ideal: honest, introspective, agile, aware, and proactive. —July 2023 | 1,100 words.
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  AI startups require new strategies: This time it’s actually different

  The typical dynamics between startups and incumbents do not apply in AI as they did in previous technology revolutions like mobile and the Internet. Ignore this at your peril. —March 2024 | 1,900 words.
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  It's a torturous chaos until it isn’t

  Even at wildly successful startups, the first few years are gut-wrenching, uncertain, on the brink of collapse, where pessimism is realism, and yet optimism is required. —April 2024 | 1,200 words.
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  Sometimes never compete on price

  The difference between “low prices” as a race to the bottom or as a success story (like Amazon, Costco, IKEA, Vanguard) is in leveraging intentional weaknesses. —April 2025 | 2,600 words.
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  Business Advice Plagued by Survivor Bias

  Advice from “successful entrepreneurs” might be unreliable due to Survivor Bias. What’s real, and what’s random? —August 2009 | 1,600 words.
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  Impostor Syndrome: Why I felt like a fraud, and how I overcame it

  Most high-performing people experience Impostor Syndrome. I did too. When you understand the cause, you can defeat it. —January 2010 | 1,800 words.
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  All pretty models are wrong, but some ugly models are useful

  Identifying useful frameworks for companies, strategy, markets, and organizations, instead of those that just look pretty in PowerPoint. —March 2025 | 1,900 words.
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  Product Purgatory: When they love it but still don’t buy

  When even “free” is too expensive. —May 2025 | 2,000 words.
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  What makes a strategy great

  Most so-called “strategies” are vague, wishful thinking, written once and never seen again. Don’t do that. These are the characteristics of great strategy. —August 2023 | 5,900 words.
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  Pricing determines your business model

  Pricing is inextricably linked to brand, product, and purchasing decisions. It cannot be “figured out later,” because it determines your business model today. —November 2014 | 1,200 words.
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  Explore vs Execute

  The two main business modalities are more different than you expect. When you hit PMF, it’s a culture-shift to switch from one to the other. —January 2025 | 2,600 words.
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  “I scratched my own itch” isn’t good enough

  This isn’t the humble-brag you think it is; The most common origin story is also common to startups that fail. But it’s a start. —March 2025 | 1,800 words.
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  The three kinds of leverage that anchor effective strategies

  Leveraging strengths – not “fixing weaknesses” – is how to win. Better when differentiated. Best when durable. Here’s how to create leverage. —June 2023 | 3,300 words.
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  Legacy

  Humans have always tried to live forever. Maybe you can, but not in the way you imagine. —September 2024 | 1,300 words.
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  Pivot Points

  Not “enabling constraints”, not “weaknesses”, not even “strengths”. The concept of a “Pivot Point” grapples with the same reality, but more constructive and useful. —September 2024 | 4,400 words.
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  “It's a Balance” isn't always the answer

  Resolve decision-making conflicts by selecting the right approach: Make a bold choice, synthesize a new solution, or find the balance. —June 2024 | 2,700 words.
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  Binstack: Making a maximal multi-dimensional decision

  Binstack is a technique for selecting the “single most impactful” solution when there are multiple, incomparable dimensions to evaluate. —July 2022 | 3,400 words.
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  Never say “no,” but rarely say “yes.”

  “Focus” requires saying “no” to most things, but there’s a way to do it that allows you to say “yes” exactly when it matters most. —April 2011 | 1,500 words.
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  “Authentic” is dead. And so is “is dead.”

  It’s lazy writing. It’s boring and undifferentiated. Say something meaningful, specific, evocative, so your website wins, and you can be proud of it. —July 2024 | 1,200 words.
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  The Code is your Enemy

  A short pep talk I delivered to kick off a Three-Day Startup challenge event. And overwhelming confirmation that the lesson is correct. —November 2013 | 1,100 words.
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  Selecting the right product metrics (KPIs)

  A novel system for selecting and presenting product KPIs, satisfying not only the product team, but also stakeholders, executives, and customers. —July 2023 | 2,600 words.
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  Failure to face the truth

  This admonition recurs in myriad books, frameworks, and topics, across decades of time. When something is so consistent, it must be wisdom. —April 2022 | 1,900 words.
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  The Startup Drake Equation

  Why do smart, driven founders fail, despite having great ideas and execution? This model offers an answer, and a path to increase the chance of success. —February 2025 | 2,800 words.
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  When you have nothing: How to find potential customers to interview

  How to find potential customers to interview before you have a product, a website, or even a name. —December 2024 | 3,700 words.
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  The unfortunate math behind consulting companies

  Hiring even one person creates a lot less profit than you’d think, and launching a product rarely works out. Here are some tips for consulting companies. —February 2011 | 2,000 words.
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  JIT selection from independent streams: An alternative to the “big backlog” of work

  The vaunted “single-threaded, ordered list” confuses “prioritization” with “work-planning,” and forces comparisons of the un-comparable. Here’s the solution. —August 2022 | 2,500 words.
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  When you want to quit because it’s just not worth it

  Are you crying in the shower because you can’t handle it anymore? Beyond Impostor Syndrome: Complete melt-down? Well, at least you’re in good company. —February 2011 | 1,700 words.
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  When should a decision be fast, or slow?

  Decisions should usually be made quickly, to accelerate action and learning. But sometimes it really is smarter to take your time. Here’s how to decide. —September 2018 | 1,300 words.
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  Distinguishing constructive criticism from bad business advice

  Beware of advice that tries to change who you are. True wisdom guides you to a better version of yourself. —December 2008 | 2,100 words.
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  Moats: Durable competitive advantage

  Industries commoditize over time, delivering similar products at similar prices resulting in low profit. Moats are the antidote; your strategy must create some. —May 2022 | 1,800 words.
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  The fundamental forces of scale

  These forces make larger companies slower and more difficult to execute, but also more effective when harnessed and leveraged. —September 2023 | 4,200 words.
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  Adjacency Matrix: How to expand after PMF

  A simple workshop that evaluates new business ideas relative to your existing strengths – the key to expanding without overreaching. —May 2024 | 2,400 words.
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  Individual efficiency vs administrative efficiency

  When to prioritize individual autonomy, and when to standardize for global optimization. —August 2024 | 2,200 words.
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  The “Great” Product Manager, a.k.a. the Impossible Product Manager

  According to the Internet, being a Product Manager is impossible. Can you ever measure up? No. But don’t worry, there’s a better answer. —April 2022 | 2,200 words.
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  In its emptiness, there is the function of a startup

  Everything about a startup changes over time. The few things that don’t, are its essence. The voyage is meaningless, unless you decide what those things are. —August 2014 | 1,000 words.
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  No wait, of course THAT is the single most important SaaS metric

  Is it LTV? Retention? NRR? Magic Number? Rule of 40? Or: Do you need to un-ask the question. —November 2024 | 1,000 words.
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  The Lindy Effect on startup potential

  On average, you’re halfway to your final destination. How, then, do we not only double from here, but 10x? —November 2014 | 1,100 words.
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  The “Convergent” theory of finding truth in darkness

  How to tell the difference between a truly great startup idea, and people saying “Sure, sounds good” when they really mean “No, I’m not buying.” —June 2012 | 1,500 words.
• 
  On the (un?)importance of design

  You redesign your entire website, customers and employees say it’s better, but none of the metrics change… Does design even matter? —June 2011 | 1,300 words.
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  The only way to guarantee startup success

  What is it like to reach the pinnacle of success? Is that where you attain happiness and fulfillment? Or are those found right here, right now. —July 2014 | 1,000 words.
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  Deciding whether an investment is worthwhile

  Why “expected value” doesn’t work; here’s a better framework for making long-term investments in your career, startup, and life. —February 2024 | 2,700 words.
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  “Stealth mode” and other f’ing brilliant strategies

  Oh you secretive devil! The last thing you need is anyone finding out about your startup. Like competitors. Or customers. —January 2025 | 1,300 words.
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  Satisficing vs Maximizing

  Fast, or Best? Choose your decision-making goal wisely, especially if you’re a natural perfectionist. —May 2017 | 500 words.
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  Worse, but unique

  An objectively “worse” strategy can win, if it leverages something unique or unexpected. Startups can use this concept to beat incumbents. —August 2023 | 1,000 words.
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  Discount gambit

  Discounting is the typical sales technique, but refusing to discount can lead to a much better business, even in the Enterprise. —March 2008 | 1,100 words.
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  You can have two Big Things, but not three

  No you can’t “have it all.” You can have two things, but not three. —January 2014 | 500 words.
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  Brittle Points: How to make companies robust

  Brittleness is when the company fails because just one component breaks. Learn some strategies for fixing Brittle Points. —December 2024 | 1,700 words.
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  p-Hacking your A/B tests

  Half of your “successful” A/B tests are false-positives. This is why, and how to fix it. —November 2024 | 2,000 words.
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  Double your productivity without more work or stress

  People love to say that getting “1% better per day” makes you 37x better after a year, but this obviously makes no sense. But 2x better is possible. —March 2009 | 1,100 words.
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  Ignoring the Wisdom of Crowds

  Discover how to leverage the wisdom of the crowds, but also when to avoid it, as it can easily lead you astray. —January 2009 | 1,100 words.
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  Human + Fallible = Love; Corporate + Sterile = Refund

  People love and forgive humans, not corporations. Expose your humanity to earn loyal, happy customers, even when you mess up. —June 2010 | 1,100 words.
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  Your non-linear problem of 90% utilization

  Is everyone working very hard, all the time, and yet accomplishing 1/10th of what it seems they should? Maybe this is why. —December 2015 | 900 words.
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  The "Talk vs Walk" workshop

  We invented this strategic exercise at WP Engine – engaging both Marketing and Product, generating actions for both sides that make products more desirable and competitive. —June 2022 | 3,200 words.
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  The Serengeti Plain: Fallacies that aren’t fallacies

  A contrarian look at logical “fallacies” that maybe aren’t so illogical after all. —October 2024 | 2,100 words.
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  Learn by Copy

  In America we’re trained that all copying is bad; of course plagiarism is, but perhaps we’re throwing the baby out with the bathwater. —February 2012 | 900 words.
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  Scaling by “delegation” isn’t good enough

  Delegation won’t scale your business. It’s more poisonous than you know. Here’s what to do instead. —February 2015 | 1,100 words.
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  Disentangling the three languages: Customers, Product, Business

  Stop talking past each other. Translate between the three “languages” of customer desires, product features, and business goals. —May 2024 | 1,500 words.
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  For probabilities, use Fermi numbers, not words

  Don’t use phrases like “unlikely” or “almost certainly.” Here’s real-world data showing why not, and what to do instead. —July 2023 | 1,000 words.
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  Startup identity & the sadness of a successful exit

  Many founders experience a profound and prolonged sadness after selling their company. But “not selling” might be worse. Maybe my story will help you. —February 2013 | 2,400 words.
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  Productive meeting activities: Leverage the team, empower the individual

  Meetings are most productive when we create something that none of us could have created alone. Here are several ways to use meeting time wisely. —May 2022 | 1,200 words.
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  Our unhealthy fixation with emulating #1

  Being “undefeated” or “number 1” might be more luck than you know. —April 2011 | 800 words.
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  How to select your first marketing channel

  When you’re brand new, how do you select your first marketing channel? —February 2025 | 1,200 words.
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  How much of success is luck?

  “You’re so lucky.” That’s true. There’s also decades of sacrifice, emotional turmoil, long hours, perseverance. So… is it lucky? —March 2009 | 1,100 words.
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  Invention is Drudgery

  Having skipped to the last page of other people’s books, we forget the rest of the journey. And, that we have to take that journey, too. —April 2016 | 500 words.
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  The “errors” that mean you’re doing it right

  Some things appear to be mistakes, but in fact should be celebrated as the expected outcomes of great decisions. —January 2024 | 1,600 words.
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  Scars

  Our emotional baggage and experience make us unique, but also serve as blinders. —January 2012 | 1,000 words.
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  Why it’s nice to compete against a large, profitable company

  Competing against big firms? Their revenue streams are their Achilles heel. Learn how smaller startups have a shot. —August 2015 | 800 words.
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  Quarterly strategic planning using the fairytale structure

  Traditional fairytale structure fits naturally in our brains, and thus can guide strategic problem-analysis, and a plan that everyone understands. —November 2023 | 4,100 words.
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  SSEBITDA – A steady-state profit metric for SaaS companies

  How can a business that is “spending to grow” determine whether it’s truly profitable underneath all that “revenue acceleration?” Here’s a way. —April 2025 | 1,800 words.
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  Color Wheels are wrong? How color vision actually works

  Artists say all colors are a mixture of red, yellow, and blue. But physics and TV screens and printers disagree. How does color really work? —January 2011 | 1,900 words.
• 
  You’re a real company when…

  What marks the moment when you become a “real” company? —April 2007 | 700 words.
• 
  How many things should there be? (Hint: Not 10)

  If we happened to evolve with nine fingers, we would have “Top 9” lists. So, a “Top 10” list probably doesn’t have the correct number of things. —December 2023 | 400 words.
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  Metrics that cannot even be measured in retrospect

  Some of the most enticing, important metrics are impossible to measure, even after the fact. Here’s how to identify and avoid this trap. —October 2023 | 1,800 words.
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  Stop saying “fail”

  Language shapes our perception of setbacks. Use words other than “failure” to describe situations and to suggest the next step. —September 2023 | 800 words.
• 
  Who's lying?

  A lesson all pilots know: How you must use multiple dials, employing different sources of energy, to report identical data, because some of it is always lying. —February 2022 | 800 words.
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  The Important Thing — powerful enough to override all your deficiencies

  This is the reason that startups succeed despite their many weaknesses. And it’s a reason to build a startup in the first place. —November 2019 | 1,200 words.
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  Capturing luck with “or” instead of “and”

  Luck always plays a role in startups, but there are ways to better capture upside and mitigate downside. —October 2019 | 800 words.
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  Distributed Logical Time

  A simple, decentralized, scalable, constant-memory mechanism for independent replicas to record events in time, preserving the “happened-before” relation in almost all cases. —February 2019 | 3,100 words.
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  Change: Damned if you do, damned more if you don't

  Everyone wants change, but doesn’t want to change. Though inevitable, change is uncomfortable and exhausting. Manage it with kindness. —August 2017 | 700 words.
• 
  Look what we did

  “How does it feel to have created two unicorns?” I don’t know; I only know what it feels like to start them, and then work with amazing people who collectively create the result. —January 2017 | 600 words.
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  Building in public forces true competitive advantage

  “Building in public” is popular: How fun when strangers cheer you on! But isn’t competitive advantage ruined when competitors know your growth rate and steal your source code? —December 2016 | 700 words.
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  Laws of 10x found everywhere

  We’re often told that some things are 10x better than others. Is that really how things work? If so, we’d better act like it. —December 2016 | 500 words.
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  Worrying is self-fulfilling; what to do instead

  Worrying makes things worse. Replace worry with preparation and strategic planning. —December 2016 | 500 words.
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  How to simplify complex decisions by cleaving the facts

  Simplify complex decisions by separating upsides from downsides, investing in upsides, vetoing with downsides, and using an appropriate decision framework. —November 2016 | 2,100 words.
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  What if there isn’t another 10x?

  What if your tech company has peaked? Is relentless growth the only path, or is it time to redefine your true impact on the world? —October 2016 | 600 words.
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  How to measure the accuracy of forecasts

  How do you assess forecasts, when the forecast is only a probability? It’s not just about accuracy. Let’s dive into the math. —June 2016 | 2,200 words.
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  Darwin doesn’t automatically select the best companies

  “Survival of the fittest” is not the same thing as “survival of the best.” Founders have the responsibility to solve both for growth and the betterment of the world. —February 2016 | 1,200 words.
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  Refutation: An acquisition is always a failure

  Independent or acquired, companies always evolve, and not always for the better. Smart exits can create opportunities for everyone involved. —September 2015 | 700 words.
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  Balance is weak. Tension is strong.

  Balance is fragile. Tension is strong —September 2015 | 300 words.
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  Zero-sum marketing channels: Good or bad for a startup to pursue?

  Paying a premium for zero-sum marketing channels? Invest in scalable, non-zero-sum channels instead. —August 2015 | 400 words.
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  On the value of Judgement

  We’re told not to judge, lest we be judged. But we are constantly judged by customers, employees, family, media, and investors. —June 2015 | 300 words.
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  New Year’s Questions (neé Resolutions)

  Do New Year’s resolutions work? Studies say “no.” Instead, Ask good questions of yourself, and follow your own advice. —December 2014 | 700 words.
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  The wrongness of relativism

  Comparing yourself to other startups? Focus on yourself instead. —December 2014 | 700 words.
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  Marketing at early startups: Deep, not wide

  Go deep on one marketing strategy that you already know well; spreading thin won’t be successful. —December 2014 | 400 words.
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  Why startup biz dev deals almost never get done

  Startups fail at biz dev because their proposals don’t make sense to bigger companies. Here’s how to adjust your approach. —April 2014 | 900 words.
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  Rare things become common at scale

  Software doesn’t scale through architecture and automation alone. New, more difficult problems appear that didn’t exist before, causing new downstream consequences. —January 2014 | 1,100 words.
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  More money if you do, more money if you don’t

  A business always takes more money than you expect, even when you take this fact into account. Here’s why. —January 2014 | 500 words.
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  Stop chopping yourself to pieces

  Achieve more by doing less: one task at a time, ample rest, and deliberate focus lead to greater fulfillment. —December 2013 | 300 words.
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  Ho Rudolph

  Rudolph claps back. —December 2013 | 300 words.
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  Imbalanced People

  A top contributor isn’t just better than ten average ones—they’re infinitely superior, driving creativity and innovation that countless others can’t match. —October 2013 | 500 words.
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  Why I don’t like the LTV metric (LifeTime Value)

  The LTV metric overcomplicates and misleads. Learn why you should use other SaaS metrics instead. —October 2013 | 1,100 words.
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  Sandy Visions

  It’s all almost magic. —August 2013 | 700 words.
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  COC: A new metric for measuring cancellations in SaaS business models

  Introducing COC: The true cost of cancellations in a scaling SaaS business. —August 2013 | 1,700 words.
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  Solving the Low-Budget Online Marketing Dilemma

  Low on cash but need marketing results? Here are four specific things you can do to grow on a budget. —May 2013 | 1,500 words.
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  Bootstrapped CPC rule of thumb: ARPU/25

  Bootstrapped and unsure about CPC? Use the rule of ARPU/25. —April 2013 | 1,300 words.
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  Reframing “Freemium” by charging the marketing department

  Freemium means high costs, low conversion, and customer feedback dominated by the non-ideal customer. Treat it as a marketing expense to ensure ROI. —April 2013 | 1,700 words.
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  “Because that’s the way it’s done” — should a founder listen?

  “They” say you can’t, but maybe you can. Embrace risk, creativity, and prove them wrong. —February 2013 | 400 words.
• 
  Better for whom?

  “Better” is always in the eye of the beholder. That’s why the question is always: Better for whom? —February 2013 | 700 words.
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  A compass is not a map

  A compass tells you which way is north, not whether you should be heading north. So what is the map to startup success? —January 2013 | 400 words.
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  But I know that he knows that I know

  Even better than trying to outwit the competition, is to not react to them at all, and just do your best, directly for your customers. —November 2012 | 800 words.
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  The rise of the “successful” unsustainable company

  We’re funding too many unsustainable companies. —October 2012 | 1,300 words.
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  “ROI” is the wrong way to sell your product

  Customers ask for ROI calculations to justify purchasing your software, but it still doesn’t convince them. Here’s what to do instead. —October 2012 | 600 words.
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  A life-changing challenge guided by Pascal’s Wager

  Applying Pascal’s Wager: Humility wins, arrogance loses. —July 2012 | 900 words.
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  What a startup does to you. Or: A celebration of new life

  A startup is a crucible – a fiery place that tests your limits, not by probing them but by violently exceeding them, all of the time. It’s worth it. —July 2012 | 1,000 words.
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  How do I know where to advertise?

  Ready to advertise but unsure where? Measure outcomes fast, start affordably, and choose platforms you understand. —June 2012 | 600 words.
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  The mid-market briar patch

  Mid-sized companies: Small enough to have small budgets, big enough for bureaucratic nightmares. —May 2012 | 1,000 words.
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  How do I stop “analyzing” and pick between two good choices?

  What if there’s no wrong answer? What’s the tiebreaker in major business decisions. —May 2012 | 600 words.
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  Which is better: Many customers at low price-point or few at high price?

  Which is better: Two companies have the same revenue, one from a few large customers and the other from many little customers —May 2012 | 1,800 words.
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  Intense Asymmetry and Self-Flagellation

  Erica Douglass sold her company for $1M, yet still struggles with self-worth; why driven people can’t escape Impostor Syndrome. —March 2012 | 1,400 words.
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  What is the value of one hour of a startup founder’s time?

  Startup founders undervalue their time. Here’s why you should act like it’s $1000/hr, and how it changes the decisions you make. —January 2012 | 700 words.
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  When being “first” is not a competitive advantage

  Is it good to be “first?” It seems so – what’s the point of being a copycat? While “first” sounds impressive, in reality it’s often not an advantage. —December 2011 | 1,000 words.
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  Hiring Employee #1

  If you want another pair of hands to screw things up, how do you acquire resumes, pair them down, and identify someone who is going to work well in your company? —December 2011 | 2,000 words.
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  Easy to criticize, hard to create

  It’s easy to explain why any given business will fail. So what? But neither is it wise to totally ignore the critics. —December 2011 | 800 words.
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  The full story of “the one important thing” for startups

  Forget small tweaks; startups should focus on one, most-critical metric, seeking only large effects. —October 2011 | 1,400 words.
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  Ballad of The Lean Startup

  An ode to validated learning. —September 2011 | 200 words.
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  When being an “expert” is harmful

  Expertise hinders learning. Learn from these examples, so that you leverage your expertise, but aren’t blinded by it. Insights come from curiosity, not certainty. —August 2011 | 1,300 words.
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  Being who you are, while becoming better

  We’re told “be yourself” to seek happiness and success. But what if “being yourself” also means striving to become better? What is “yourself?” —August 2011 | 1,600 words.
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  10 things I’ve never heard a successful startup founder say

  Please stop repeating these ideas! This isn’t how successful companies work. —August 2011 | 300 words.
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  Startup Weekend pep talk: It ain’t the code

  At Startup Weekend, it’s not the code that wins, but identifying needs and crafting a clear pitch. Build a company, not just a website. —July 2011 | 1,100 words.
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  Do I dare call bullshit aloud? Do you?

  A side-effect of my moderate, only-in-bubble fame is a barrage of “special” offers, guest-post requests, pleas for attention, and modest, tasteful bribery. —May 2011 | 900 words.
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  Specificity: A weapon of mass effectiveness

  Want to write better? Swap generic words for specifics to make your text clear, powerful, engaging, and even funny. —March 2011 | 1,000 words.
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  Startup Exercise: What can’t be solved with money?

  What can’t be solved with money, are the most valuable things. —March 2011 | 1,000 words.
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  Marketing Platform Independence

  Basing your startup on a volatile platform is risky. Choose platforms with this in mind, or diversify. —November 2010 | 1,100 words.
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  Reputation isn’t as powerful as you imagine

  Blogger with tens of thousands of subscribers launches a new venture… and gets only 2 signups. Not the advantage you thought it was. —October 2010 | 1,200 words.
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  If you build it, they won’t come, unless…

  A/B tests and accumulating Twitter followers is not a marketing strategy, just as “we’ll use salt and cheese” isn’t a recipe. —October 2010 | 1,800 words.
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  Yes, but who said they’d actually BUY the damn thing?

  Have a great idea? Prove it by finding ten customers ready to hand over cash. Everything else is avoiding the truth. —August 2010 | 1,400 words.
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  Real Unfair Advantages

  It’s not a question of if someone copies your business idea, it’s when. —July 2010 | 2,800 words.
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  Out of the cesspool and into the sewer: A/B testing trap

  Don’t get caught in a cycle of incremental A/B testing. Sometimes you need to try something radically different. —June 2010 | 600 words.
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  The Pattern-Seeking Fallacy

  We humans are terrible at discerning patterns from randomness, and in marketing data we unwittingly find “insights” that are actually noise. Here’s how to fix that. —June 2010 | 1,500 words.
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  Telling the 800-lb Gorilla to Shove it up his Ass

  You worry about competition from the big, brand-name, deep-pocketed company. But there are better things to worry about and ways to avoid running into gorillas in the first place. —May 2010 | 1,300 words.
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  Tech Support is sales

  Tech support isn’t just troubleshooting; it’s the face of your company. Which means it’s your brand, your positioning, and when it’s excellent, it is sales. —May 2010 | 1,300 words.
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  Not disruptive, and proud of it

  I remember “disruptive” when it was called a “paradigm shift.” You should be worrying more about making something people want to buy, and less about disrupting everything. —April 2010 | 1,600 words.
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  Maybe not so much with the “optimization”

  In the quest for optimization, A/B tests, metrics, and funnels, we’re in danger of losing the fun and value of creative work. —April 2010 | 900 words.
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  A butterfly flaps its wings and you make a sale

  It is true that small changes can have enormous effects? Or is this just what optimization consultants want us to believe? —March 2010 | 1,000 words.
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  The true meaning of common idioms

  Struggling to understand American business vernacular? Here’s a convenient reference. —March 2010 | 600 words.
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  Employed with a side of startup

  Starting a side gig during your 9-to-5: Avoid legal issues and maximize success. —March 2010 | 1,700 words.
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  Pick one and own it

  What if your company could have only one single advantage over the competition? This exercise will make your positioning and strategy stronger. —March 2010 | 1,900 words.
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  Enough with the “expert” guilt

  Tired of being told you need “10,000 hours” before you can call yourself an “expert,” and maybe become a “success?” Maybe you don’t. —February 2010 | 700 words.
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  Sunk Costs: An invisible, pervasive peril

  From blown budgets to failed features, sunk costs result in irrational choices. —February 2010 | 1,300 words.
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  Rude Q&A: The constructive devil’s advocate

  Nothing clarifies things quite like a hyperactive, all-knowing, all-seeing, real asshole of a devil’s advocate beating the living crap out of you. —February 2010 | 1,300 words.
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  A Tradeshow Checklist, born of experience

  My tips from running booths at dozens of tradeshows. —January 2010 | 2,600 words.
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  Discover what’s blocking sales with less than a day of work

  Uncover sales blockers in 24 hours with these 11 strategies. —September 2009 | 2,200 words.
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  Put down the compiler until you learn why they’re not buying

  Technical founders, step away from the code. Gather insights from non-buyers, rather than just adding more features. —September 2009 | 1,100 words.
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  If Kindergarten were like Social Media Marketing

  What if we ran kindergarten classes with the same rules as social media marketing? —September 2009 | 400 words.
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  You’re a little company, now act like one

  You’re afraid that looking like being a small company means you’ll lose sales. It’s actually the opposite – you’re alienating your best customers. —August 2009 | 1,000 words.
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  Darwinian advice for “Going Viral”

  Some of my articles have “gone viral.” While you can’t force it to happen, this is my Darwinian Theory of how to “go viral.” —August 2009 | 1,200 words.
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  Sacrifice your health for your startup

  Maximizing your chance for success means sacrificing health and family. This sounds controversial, but it’s not just me. —June 2009 | 1,100 words.
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  Letters to Joel Spolsky

  I regret to inform you… —June 2009 | 1,100 words.
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  Too small to fail: How startups can grow in recessions

  These two little startups are exploding in sales, even in recession. Here’s how they’re doing it, and how you can too. —June 2009 | 800 words.
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  Communicating Values: Show, don’t Tell

  Authentic values shine through actions, not marketing buzzwords. —May 2009 | 700 words.
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  How to get customers who love you even when you screw up

  Customers love you when you’re honest, even about your foibles. We forgive honest mistakes from earnest people, not stolid, cold, inhuman corporations. —April 2009 | 1,200 words.
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  Easy statistics for A/B testing and hamsters

  A/B testing tools often lie about whether something is “statistically significant.” Here’s an extremely simple, mathematically sound formula to compute it for yourself. —April 2009 | 1,500 words.
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  High-concept pitches are not your friend

  High-concept pitches are too brief, and too ambiguous. Opt instead for clarity, and define yourself on your own terms. —February 2009 | 600 words.
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  Your idea sucks, now go do it anyway

  Your idea probably sucks, and it doesn’t matter because your business will probably turn out to be something completely different. —December 2008 | 800 words.
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  Breaking the Rules

  When you know the rules, then you can break the rules. —December 2008 | 700 words.
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  Standing out from the noise

  Ensure your pitch works even in our noisy, distracting, multi-tasking world. —December 2008 | 500 words.
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  Bed, Bath, Linens, Things, Beyond, and More!

  “And more!” is lazy marketing. Be specific, be passionate, and make people care. —November 2008 | 600 words.
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  Strong opinions, somewhat weakly held

  A strategy that changes all the time cannot be executed, but a strategy that never changes is definitely incorrect. —November 2008 | 600 words.
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  The leading provider of meaningless marketing solutions

  Marketing buzzwords and generic phrases hurts your brand. Use clear messaging instead of meaningless jargon. —November 2008 | 600 words.
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  Love the messenger

  Being obsessively and genuinely excited about something is contagious. And good sales. In any industry, with any product. —November 2008 | 700 words.
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  Is it OK to Sucks?

  Using humor or edgy language works. It’s risky, and may alienate some potential customers, but it wins you more customers and shows differentiated personality. —October 2008 | 300 words.
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  Procrastinate for Success!

  Procrastination can be a useful tool. You can’t do everything. So don’t. —October 2008 | 600 words.
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  Software Quality Mortgage

  Quick software releases have long-term costs. Stakeholders and engineers alike must be prepared to repay the mortgage known as “tech debt.” —September 2008 | 800 words.
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  Hello, I’m 1074018628

  Is “customer service” a genuine service? Or is it a shield so that most people at your company never have to speak to one of those pesky customers? —August 2008 | 200 words.
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  Limiting Options

  The winning strategy in Othello is to minimize your opponent’s options, rather than maximizing your own. The same principle applies to competitive strategy. —April 2008 | 800 words.
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  The “Opposite Test”

  Elevate your product marketing: Use the Opposite Test to avoid generic bullet points and craft compelling, unique features. —April 2008 | 1,000 words.
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  Tell me a story

  Why do we love Malcolm Gladwell even if his theories are debunked? We love a great story. —February 2008 | 900 words.
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  Outside-In

  Actions speak louder than slogans: Great support, quality, service, is best sold through demonstration. —December 2007 | 500 words.
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  Guy in a bear suit

  Tradeshow booths need something to help them stand out. A guy in a bear suit is one way to do it. —April 2007 | 600 words.
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  Selling to the Bottom

  More than a decade before “Product-Led Growth” became a thing, I was selling non-recurring-revenue-software to Fortune 500 companies from the bottom up. —January 2007 | 700 words.
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  Idiot! Buying SmartBear.com

  How my hesitation on SmartBear.com led to a $2000 expense. A lesson in acting fast. —January 2007 | 500 words.
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  Jason Cohen: About the author

  I built a few companies, two of which are now unicorns, both bootstrapped and VC-funded, bought and sold a few, invested in dozens, and wrote about everything I know.