Watch Objective Signals to Spot Strategy Mistakes Early
OK, you’re confident in strategy S and tactic T and feature F and target market M. Good; don’t constantly second-guess yourself. But… if you 𝘸𝘦𝘳𝘦 wrong, what objective signal would tell you that? You’d better know, and be watching.
Startups Thrive in Niche Pockets of Large Markets
Small markets are good if you can be #1. Large markets contain niches that are too small for incumbents to target but perfect for startups; there's budget and people are searching for it. So, that's often better. https://t.co/8TZHTobLGs
Don’t Chase Enterprise Just because some Teams Buy
So many startups erroneously think they should “go upmarket to the Enterprise” just because some teams at large companies bought their software. 50% of people work at big companies, and they’re already buying. Here’s more blunders to avoid: https://t.co/cE9pImYPyy
Scaling People Beats Scaling Tech—Hire First
As difficult as it is to scale infrastructure… …the hardest thing is to scale people. Yet technical founders spend most of their time on tech, because it’s interesting. Exactly wrong. That’s what you’re good at hiring for. Go solve the more important, harder problem.
Failure Pinpoints One Dead End, Not the Whole Path
Failure means you’ve identified one very specific way that doesn’t work. Sadly, that leaves almost everything else. That’s why Edison took 1000+ tries. Each failure didn’t confer enough “learning.”
Fit Requires Displacing a Top Customer Priority
Another harsh truth about product-market fit: It's not enough that customers see value. They need to see enough value to displace one of their current top-3 priorities. Which is isn’t, which means you need to already be one of those priorities. Here’s how. https://t.co/ZunSUrdwOP
Prioritize the Vital Few, Sleep Well, Ignore Endless List
The to-do list will always be infinite. Therefore, exactly how far you get down the list isn't critical, but what IS critical is that the few things you actually do, are the most important ones, and done really well. Which requires: 1. Prioritization 2....
Luck's Role: Balance Acknowledgment and Personal Agency
Successful people don’t want to admit how much of it was luck. People who aren’t where they want to be in life overemphasize luck. It’s easier to blame the universe than take responsibility or agency. Both are right, and wrong. And you can...
SaaS 1% Conversion Means CPC ≤ 1% of CAC
Most SaaS companies report about a 1% conversion rate - you need 100 visitors to make 1 sale. This means your maximum CPC should be 1% of your maximum CAC. Here’s how to calculate all these things: https://t.co/LXBj3k7vLd
Creativity and Execution: Both Needed for Success
Creativity, invention, ideation. • vs - Consistent execution, planning, good decisions. Are they two different modes, or do you have to learn to do both? Or is one actually not that useful?
Mixed Customer Feedback: Opportunity or Unclear Idea?
You’re talking with customers. Of course they tell you different things. Is that a sign of over-abundance of opportunity? Or a sign that the idea is unclear, unfocused, unvalidated? Here’s how I evaluate it: https://t.co/0urIu6dbG4
Understanding Startup Failure: A Risk‑Focused Path to Success
Most startups still fail, despite all the advice, insightful ideas, and crazy hard work. Here is a risk-oriented theory of “why,” and how to improve your chances of success: https://t.co/xKPhWzGrMK
Both Failures and Successes Hide Many Broken Pieces
When a startup fails… Typically 10-20 things were very broken. Which one(s) “caused" the failure? In successes, 10-20 things are 𝘢𝘭𝘴𝘰 broken, but it didn't matter. So, what do we learn from the 10-20 things? Anything?
Hire Reliable Talent: The Rare Asset Founders Need
Being extremely reliable is a trait that others notice even if they don’t say so out loud. Highly prized, both because it is rare and because it is valuable. It’s something founders rarely are, but hiring people like that can help make...
Separate Trade‑offs: Speed vs Quality, Deadline vs Scope
Rather than “speed, quality, cost: pick 2”… My sense is: • speed vs quality -and separately- • deadline vs scope -and separately- • turning speed vs scale Thoughts?
Deliver Double Value, Charge Half, Watch Profits Soar
The best businesses deliver $4 of value, charges $2, and costs them $1 to do it. This is what Figma did, and therefore why it was worth 50x ARR. And why their customers aren’t upset that they’re so profitable. You can too: https://t.co/HFQMWgThom
High Cancellation Rates OK Only With Supporting Business Model
Any metric can be out of whack if the rest of the business model supports it. For example Shopify is objectively a phenomenal business, but their cancellation rate is 7%/mo. That's fatally high… normally. But they have such great NRR for...
Most Launches Fail; Focus on Daily Customer Acquisition
Launches sometimes work. It’s often news when they do, so you think they’re a good idea. It's just: (a) usually they don't work and (b) you need customers every day after and (c) it's a lot of time and energy. Which makes...
CEOs Must Delegate to Avoid Micromanaging Trivial Decisions
As the CEO, if you’re constantly answering trivial questions, making little decisions, you have a problem of your own making. Is it because you're not allowing others to decide? They think they're not empowered? It's a bad sign and you have to...
Iterate Goals and Systems: Adapt While Executing
Vacillate between goals and systems. Start with a directional goal. What systems could do that? But you learn while you execute, so the goal might change, as might the system. Etc..
Take a Small Step Today, but Still Plan Ahead
When faced with a monumental project, often people say: What’s one thing you can do today that moves this forward at all? Do that. Good: It gets you unstuck and starts momentum. Bad: It’s not a plan for how to actually accomplish...
Write for Real Customers, Not Giant Corporate Fantasies
Your next sale won't be a 1000-seat order from Google. But is your homepage written as if this is the target? Formal, obtuse, corporate-speak, pretending to be a mature, stable company. You’re alienating your actual best customers. https://t.co/2jsBd6Z3Ap
Customers Prefer Familiar Solutions Over Disruptive Products
Most people don't want their lives turned upside down by a “disruptive” product. They want solutions for their current problems, with tools and metaphors they already understand. “Disruption” is rarely a good strategy. https://t.co/qb8ekeCEDM
Use Expertise Wisely, Avoid Its Blind Spots
Leveraging your expertise is wise, of course. You’ll be more efficient and make better decisions. Well, sometimes? Or “expertise” can be blinders. Knowing that, you can avoid the trap, and indeed leverage your expertise. https://t.co/19xHUGd9lC
Premature Optimization Costs Time Across All Teams
Engineers know the phrase: "no premature optimization." And then they go and do it anyway. Not just in code performance, but in design, and in the entire rest of the company. And yet, the principle applies everywhere. You’re wasting time you can’t afford to...
Charge More for Quality: Best Profit and Pride
Three strategies: 1. More for more (i.e. pay more for the best) 2. More for less (i.e. cheaper, but we still have features, mostly) 3. Less for less (i.e. doesn’t do much, but affordable) All valid, but the first is best for both profit...
Raise Money Only When You Have a 10x Plan
If you want to raise money because “This would be a lot easier with a little more money,” you are not ready to raise money. If you want to raise money because “I know how to use $X to 10x the...
Separate User and Buyer Personas: Tailor Message, Timing, Channel
If the user and the buyer are different people, what are you trying to convince each of? When? (Trials vs discovery) Where? (In-product vs sales material) Etc. Treat as specific, separate personas.
Software's UX Makes It Anything But a Commodity
Software is not a commodity, although some are closer or farther. To see why, imagine me forcing you to swap out your email client, or your IDE, or your spreadsheet or docs app, and tell me you won't care at all. UX...
Avoid Single-Metric Focus: It Creates Blind Spots
Staying too focused on one metric creates blind spots. While it’s not necessarily a “balance” -- because they’re not equally important -- there isn’t “one metric to rule them all.” https://t.co/IwJzk6iCpu
Try Sharing Honestly; Few See, some Love.
Are you 𝘴𝘤𝘢𝘳𝘦𝘥 to put yourself out there? To be honest on social media, or build in public including failures? Totally fair. You don’t 𝘩𝘢𝘷𝘦 to be public, you know. But, you could just try. Probably, no one will see anyway. And some will love...
True Strategy Demands Choosing, Not Embracing Contradictory “Both”
ICYMI: Fresh new article dropped: The Opposite Test: "Good design" isn't strategic because "bad design" was never smart. But “all-in-one” vs “small core + ecosystem” is real because both result in beloved, successful products. If both sides work, "both" is incoherent. “Strategy” means making...
Uncover Hidden Customer Concerns to Optimize Pricing
We went into this sales call and found all sorts of weird things that had nothing to do with our product. We asked about it, and learned a 𝘵𝘰𝘯 that allowed us to price and sell our product better. Here’s what we...
Target High‑value Buyers, Not Discount‑driven Churners
Discounts get you customers who can’t afford the product. And so they churn when the discount wears off. Wasting everyone’s time, and unprofitable. Redirect your efforts towards getting customers who want your product so much, they think it’s too cheap.
Strategic Choices, Not Platitudes, Uniquely Align Your Company
ICYMI: Fresh new article dropped: Strategy is an integrated set of choices that uniquely positions your company. But what kinds of choices? Not the crappy platitudes like “We put customers first.” The kind that actually aligns everyone in the company to win,...
Targeted Advantage: Explain Why You Win for Segment S
I know you want to say you’re “better” than competitor G. Probably, though, it 𝘪𝘴 better for customer segment S but not for T. Why specifically is it better for S? And worse for T? Put 𝘵𝘩𝘢𝘵 in your sales material. Rather than...
Focus on Strengths, Mute Blocking Weaknesses
Almost always: Double-down on your strengths rather than blunt weakness. Exception: When a weakness is directly blocking your goals or an obstacle to the most important next steps for the company. Even then, just mute it, don’t try to “turn it into...
You Can only Juggle Two of Three Priorities
Can you have a full-time job, and devote the time necessary to build a startup, and spend quality time with family every day? At least one of those things will suffer. You can have two Big Things but not three. https://t.co/uCnzbXtN3G
Create Boss‑focused Reports During Trial to Close Deals
You make software for person P. They have a boss Q. Or better, their C_O. If Q wants your product, P gets to buy it. So, can you make a report or daily/weekly email or etc. that Q wants? Do it during the trial,...
Ship Fast to Keep Iteration Speed High
A reason to ship in 1 month instead of 6 is to incorporate feedback. Another is that a 6-month codebase will be a lot hard to to change than a 1-month. You could even still start from scratch. At the beginning, anything...
Bootstrappers Must Charge $30‑$80 for Sustainable Growth
Bootstrappers need to have prices like $30/mo-$80/mo, not like $10/mo. It’s not harder to get customers (see how many times someone raises prices and # cust/day doesn’t change), but you have no money for anything - no marketing, no engineering, no...
Context Determines Whether Solo or Co‑Founding Wins
It is better to be single or attached? Well, do you mean in a toxic relationship or a loving supportive one? Context always matters. Now do this one: Is it better to be a single founder or a co-founder?
Authenticity Wins: People Prefer Doing Business With Those They Like
Many (most?) people pick up on insincerity. Many (most?) people like to do business with people they like. So…
Ads Work; Doubting Them Reveals a Skill Gap
So many people say “ads don’t work; write content.” All of my companies for 22 years grew with ads 𝘧𝘪𝘳𝘴𝘵 and forever. Ads won't be effective for 𝘢𝘭𝘭 companies, but "I've never seen it work" is an admission of lack of...
Prioritize Marketing and Sales Over Endless Feature Tweaking
You will naturally spend more time making features and tweaking design rather than marketing, sales, and facing the difficult truths about why customers are cancelling. That’s why you need special effort on those areas. The full roadmap: https://t.co/slGN2Hmjwb
Ask Yourself Hard Questions, Then Answer Them Confidently
I left those meetings angry at first, but then embarrassed that I didn’t have better answers, and then motivated to get the right answers. So I started writing my own rude Q&A: • Why do I even exist when the market already...
Anticipate Investor Attacks with a Rude Q&A
When I started WP Engine, I thought I was pretty good at pitching. I had sold millions of dollars of software at Smart Bear, and I’d helped other companies with their pitches and fundraising. But of course it’s different when someone...
Prioritize Bold, Visible Marketing Levers Over Subtle Nudges
Instead of chasing subtle subliminal effects that get wiped away by ambient noise, we should focus on big, non-subliminal impacts in marketing. Like the home page, pricing, positioning, promises, competitive dynamics, and customer segmentation. https://t.co/KUXMFIswTZ
When CEOs Outshine Teams, Hiring Is Failing
Early on, the CEO is “the best person at the company” at some things. Often sales (passion + knowledge) or product vision. But by 100 people, if the CEO is “better than everyone” at 𝘢𝘯𝘺𝘵𝘩𝘪𝘯𝘨, the CEO has hired poorly, and...
Adjust ROI: Account for Estimation Errors in Task Prioritization
ROI is a good way to prioritize mid-sized tasks, but estimation errors (both in duration and in impact) can change the ROI by 2x-5x, so you need a system that understands that and causes you to select the right tasks...