The Curious Engineer

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A Smart Bear

longform.asmartbear.com

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

Essays / personalGeneral

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214 from 1 Jan 2000 to 11 Oct 2026
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monthly (11 in the last year)
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personal blog
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2026 9

  1. "You didn't do it right"
  2. What is the value of one hour of a startup founder's time?
  3. Lost confidence
  4. Worrying is self-fulfilling; what to do instead
  5. How to hire people who are better than you
  6. Maybe not so much with the "optimization"
  7. Strategic choices: When both options are good
  8. A compass is not a map
  9. Creating space

2025 31

  1. Scaling by "delegation" isn't good enough
  2. Mission, Vision, poTAYto, poTAHto
  3. When being an "expert" is harmful
  4. Your target market isn't demographic
  5. Yes, but who said they'd actually BUY the damn thing?
  6. Max MRR: Your growth ceiling
  7. Specificity: A weapon of mass effectiveness
  8. Ruthless prioritization while the dog pees on the floor
  9. Bootstrapped CPC rule of thumb: ARPU/25
  10. More or less
  11. Rude Q&A: The constructive devil's advocate
  12. When customers buy your competitor's product… and then buy yours
  13. Invention is Drudgery
  14. Product Purgatory: When they love it but still don't buy
  15. How to get customers who love you even when you screw up
  16. SSEBITDA⁠--A steady-state profit metric for SaaS companies
  17. Startup Exercise: What can't be solved with money?
  18. Sometimes never compete on price
  19. How to simplify complex decisions by cleaving the facts
  20. All pretty models are wrong, but some ugly models are useful
  21. Reframing "Freemium" by charging the marketing department
  22. The wrongness of relativism
  23. "I scratched my own itch" isn't good enough
  24. Why it's nice to compete against a large, profitable company
  25. How to select your first marketing channel
  26. Our unhealthy fixation with emulating #1
  27. The Startup Drake Equation
  28. On the (un?)importance of design
  29. "Stealth mode" and other f'ing brilliant strategies
  30. The Important Thing⁠--powerful enough to override all your deficiencies
  31. Explore vs Execute

2024 52

  1. A butterfly flaps its wings and you make a sale
  2. When you have nothing: How to find potential customers to interview
  3. Solving the Low-Budget Online Marketing Dilemma
  4. Brittle Points: How to make companies robust
  5. Scars
  6. Intense Asymmetry and Self-Flagellation
  7. p-Hacking your A/B tests
  8. A life-changing challenge guided by Pascal's Wager
  9. No wait, of course THAT is the single most important SaaS metric
  10. Tech Support is sales
  11. The Serengeti Plain: Fallacies that aren't fallacies
  12. You're a little company, now act like one
  13. Why startup biz dev deals almost never get done
  14. Pivot Points
  15. The Code is your Enemy
  16. Ignoring the Wisdom of Crowds
  17. Legacy
  18. Human + Fallible = Love; Corporate + Sterile = Refund
  19. Profitable on day one!
  20. The mid-market briar patch
  21. Individual efficiency vs administrative efficiency
  22. Double your productivity without more work or stress
  23. "Authentic" is dead. And so is "is dead."
  24. How much of success is luck?
  25. How annual pre-pay creates an infinite marketing budget
  26. Procrastinate for Success!
  27. Not disruptive, and proud of it
  28. "It's a Balance" isn't always the answer
  29. Being who you are, while becoming better
  30. The Lindy Effect on startup potential
  31. When being "first" is not a competitive advantage
  32. Disentangling the three languages: Customers, Product, Business
  33. Rare things become common at scale
  34. Hello, I'm 1074018628
  35. Adjacency Matrix: How to expand after PMF
  36. Capturing luck with "or" instead of "and"
  37. It's a torturous chaos until it isn't
  38. Learn by Copy
  39. The "Convergent" theory of finding truth in darkness
  40. Avoid blundering: 80% of a winning strategy
  41. Color Wheels are wrong? How color vision actually works
  42. Stubborn Visionaries & Pigheaded Fools
  43. The Pattern-Seeking Fallacy
  44. AI startups require new strategies: This time it's actually different
  45. How startups beat incumbents
  46. Easy statistics for A/B testing and hamsters
  47. Easy to criticize, hard to create
  48. Deciding whether an investment is worthwhile
  49. Pick one and own it
  50. The "errors" that mean you're doing it right
  51. How to measure the accuracy of forecasts
  52. Selling to Carol: Why targeting an ICP brings 10x more customers than you expected

2023 42

  1. "ROI" is the wrong way to sell your product
  2. The roadmap to Product/Market Fit (PMF)… maybe
  3. The unfortunate math behind consulting companies
  4. How many things should there be? (Hint: Not 10)
  5. Change: Damned if you do, damned more if you don't
  6. Quarterly strategic planning using the fairytale structure
  7. Reputation isn't as powerful as you imagine
  8. You're a real company when…
  9. Product/Market Fit (PMF): Experience & Data
  10. Rich vs. King in the Real World: Why I sold my company
  11. Metrics that cannot even be measured in retrospect
  12. Building in public forces true competitive advantage
  13. Your non-linear problem of 90% utilization
  14. Never say "no," but rarely say "yes."
  15. The fundamental forces of scale
  16. The only way to guarantee startup success
  17. Stop saying "fail"
  18. Your customers hate MVPs. Make a SLC instead.
  19. Worse, but unique
  20. Impostor Syndrome: Why I felt like a fraud, and how I overcame it
  21. What makes a strategy great
  22. Startup identity & the sadness of a successful exit
  23. In command
  24. Distinguishing constructive criticism from bad business advice
  25. Selecting the right product metrics (KPIs)
  26. Business Advice Plagued by Survivor Bias
  27. For probabilities, use Fermi numbers, not words
  28. Discount gambit
  29. The three kinds of leverage that anchor effective strategies
  30. Satisficing vs Maximizing
  31. Using the Needs Stack for competitive strategy
  32. In its emptiness, there is the function of a startup
  33. Willingness-to-pay: Creating permanent competitive advantage for the right reasons
  34. You can have two Big Things, but not three
  35. More money if you do, more money if you don't
  36. What a startup does to you. Or: A celebration of new life
  37. How repositioning a product allows you to 8x its price
  38. When you want to quit because it's just not worth it
  39. Excuse me, is there a problem?
  40. When should a decision be fast, or slow?
  41. Pricing determines your business model
  42. Navigating the unpredictability of everything

2022 14

  1. Finding Fulfillment
  2. The Iterative-Hypothesis customer development method
  3. JIT selection from independent streams: An alternative to the "big backlog" of work
  4. Rocks, Pebbles, Sand: How to implement in practice
  5. Binstack: Making a maximal multi-dimensional decision
  6. Fermi ROI: Fixing the ROI rubric
  7. The "Talk vs Walk" workshop
  8. Productive meeting activities: Leverage the team, empower the individual
  9. Moats: Durable competitive advantage
  10. The "Great" Product Manager, a.k.a. the Impossible Product Manager
  11. Failure to face the truth
  12. Extreme brainstorming questions to trigger new, better ideas
  13. The Elephant in the room: The myth of exponential hypergrowth
  14. Who's lying?

2019 1

  1. Distributed Logical Time

2017 1

  1. 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.

2016 3

  1. 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.
  2. What if there isn't another 10x?
  3. 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.

2015 4

  1. Refutation: An acquisition is always a failure
  2. Balance is weak. Tension is strong. Balance is fragile. Tension is strong —September 2015 | 300 words.
  3. 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.
  4. 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.

2014 2

  1. 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.
  2. 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.

2013 8

  1. 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.
  2. Ho Rudolph
  3. 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.
  4. Why I don't like the LTV metric (LifeTime Value)
  5. Sandy Visions It’s all almost magic. —August 2013 | 700 words.
  6. COC: A new metric for measuring cancellations in SaaS business models
  7. “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.
  8. 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.

2012 5

  1. 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.
  2. The rise of the “successful” unsustainable company We’re funding too many unsustainable companies. —October 2012 | 1,300 words.
  3. 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.
  4. 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.
  5. Which is better: Many customers at low price-point or few at high price?

2011 6

  1. Hiring Employee #1
  2. 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.
  3. Ballad of The Lean Startup
  4. 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.
  5. 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.
  6. 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.

2010 10

  1. 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.
  2. If you build it, they won't come, unless…
  3. Real Unfair Advantages
  4. 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.
  5. Telling the 800-lb Gorilla to Shove it up his Ass
  6. The true meaning of common idioms Struggling to understand American business vernacular? Here’s a convenient reference. —March 2010 | 600 words.
  7. 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.
  8. Enough with the "expert" guilt
  9. Sunk Costs: An invisible, pervasive peril From blown budgets to failed features, sunk costs result in irrational choices. —February 2010 | 1,300 words.
  10. A Tradeshow Checklist, born of experience My tips from running booths at dozens of tradeshows. —January 2010 | 2,600 words.

2009 9

  1. 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.
  2. Put down the compiler until you learn why they're not buying
  3. 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.
  4. 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.
  5. 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.
  6. Letters to Joel Spolsky
  7. 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.
  8. Communicating Values: Show, don’t Tell Authentic values shine through actions, not marketing buzzwords. —May 2009 | 700 words.
  9. 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.

2008 12

  1. Your idea sucks, now go do it anyway
  2. Breaking the Rules
  3. Standing out from the noise Ensure your pitch works even in our noisy, distracting, multi-tasking world. —December 2008 | 500 words.
  4. Bed, Bath, Linens, Things, Beyond, and More! “And more!” is lazy marketing. Be specific, be passionate, and make people care. —November 2008 | 600 words.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. 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.
  10. Limiting Options
  11. The "Opposite Test"
  12. 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.

2007 4

  1. Outside-In Actions speak louder than slogans: Great support, quality, service, is best sold through demonstration. —December 2007 | 500 words.
  2. 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.
  3. 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.
  4. Idiot! Buying SmartBear.com How my hesitation on SmartBear.com led to a $2000 expense. A lesson in acting fast. —January 2007 | 500 words.

2000 1

  1. 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.