Welcome to A Smart Bear: Longform

Articles from building two unicorns over two decades, both bootstrapped and VC-funded.

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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 | 5,500 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 | 6,700 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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  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 | 3,600 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 | 4,800 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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  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 | 5,800 words.
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  Fermi ROI: Fixing the ROI rubric

  Traditional rubrics fail to reveal the best answers, or how explain those answers to others. After explaining why, the following system solves both failures. —June 2022 | 4,800 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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  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 | 4,100 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 | 3,600 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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  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 | 3,900 words.
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  When customers are “willing” to pay

  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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  Pricing determines your business model

  Pricing is inextricably linked to brand, product, and purchasing decisions. It cannot be “figured out later,” because determines your business model today. —November 2014 | 1,200 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 | 1,500 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 | 3,500 words.
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  Selecting the right product metrics

  A novel system for selecting and presenting product KPIs, satisfying not only the product team, but also stakeholders, executives, and customers. —July 2023 | 2,500 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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  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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  The unfortunate math behind consulting companies

  Hiring even one person creates a lot less profit than you’d think, and launching a product is almost impossible. 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 | 2,600 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 | 1,000 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 antedote; your strategy must create some. —May 2022 | 1,800 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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  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 | 4,300 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.
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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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  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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  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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  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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  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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  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 | 3,000 words.
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  Your customers hate MVPs. Make a SLC instead.

  “MVP” is a selfish process, abusing customers so you can “learn.” SLC is an alternate philosophy that results in fast, validated learning, that customers love. —August 2017 | 1,400 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.
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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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  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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  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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  Your non-linear problem of 90% utilization

  Is everyone is working very hard, all the time, and yet accomplishing 1/10th of what it seems they should? Maybe this is why. —December 2015 | 800 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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  Scale makes rare things common: Why scaling software is harder than it looks

  Software cannot scale through architecture and automation alone. New, more difficult problems appear that didn’t exist before, also bringing 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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  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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  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 | 1,800 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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  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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  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 doesn’t predict who will win. —December 2011 | 1,000 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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  Reputation isn’t as powerful as you imagine

  Blogger with thousands of followers gets 2 signups for a new venture… not the advantage you thought? —October 2010 | 1,100 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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  Why I feel like a fraud (Impostor Syndrome)

  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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  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 | 1,000 words.
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  You’re a real company when…

  What marks the moment when you become a “real” company? —April 2007 | 700 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.