Tips for Achieving Speed and Flexibility in Startups

My startup pivoted 6 times before we landed on an idea that got us to PMF (signal-based sales platform for Demand Gen). In the beginning, here are 6 lessons I wish I knew: 1 - On Pivoting: alternate between open and closed periods Most founder say say, 'We're going to try this new idea, but we're not going to get rid of the old idea'... Instead do an open period of exploration for 30 days. Any idea works. Then pick one. Then do a closed period. Start with 30 days. You're ONLY allowed to work on that one idea. If a new idea comes in? write it down on a doc titled "ideas to return to during open period" After 30 days you can decide: do we continue in a closed period or return to an open period. Then repeat but make the closed periods longer and longer (60 days, 100 days, 1 year). Dedicate specific periods to exploration, then commit entirely to execution for increasingly longer intervals. 2 - On Co-Founders: talk to your co-founders daily If I'm not going back and forth, seven days a week, 365 days a year, with my co-founders, we're not moving the chains in the business. This level of communication is non-negotiable for alignment and rapid progress. 3 - On Decisions: choose whatever makes you $$ the fastest Whenever a team member proposes an idea to me I say "Tell me a story that starts with your idea and ends with us making more money, and make that story as short as possible." The fewer steps between idea and revenue, the better. 4 - On Focus: cut what doesn't fit I made the tough decision to fire 11% of our customers last year when we moved up market and they weren't ICP. This freed resources and focus to better serve our ideal customers. You can cut lots of projects/focuses in your startup without missing out much. 5 - On Personal Speed: embrace necessary discomfort When things aren't going well, resist the urge to focus only on what you're good at, and instead address the fundamental issues. If things suck and you're an engineer - you will code because you're good at it If things suck and you're a seller - you will sell because you're good at it But if things suck you can't get out of it by doing what you do best. Don't do the things that make you comfortable, because you'll fail if you do. Engineers go sell. Sellers go to product/customer discovery. 6 - On Company Speed: build learning into your culture One of our core values at Warmly is "slope > Y-intercept" – we prefer team members who learn quickly over those who start with more knowledge but grow more slowly. It's kind of a math nerd thing but slope is your rate of change. Y-intercept is where you start. Whoever has the highest rate of change (aka learning) will always win over time no matter who has the higher start. I've seen new grads run laps around enterprise sellers in 18 months because they were savages. Put speed of learning into your company. #founder #startup

Chasing 'Perfect' Decisions Ever watch a brilliant founder flatline their startup? I have. More times than I can count. And it always starts the same way: paralysis by analysis. Here's the uncomfortable truth most "thought leaders" won't tell you: Being right is crushing your business. Think I'm crazy? Let's do some math: A "perfect" decision after 3 weeks = 70% success rate A "good enough" decision today = 60% success rate Seems obvious which is better, right? Wrong. While you're polishing that one decision, your competitors made three "good enough" moves and learned from each one. That's why Amazon's Jeff Bezos splits decisions into two types: • Type 1: Big, irreversible choices. Take your time. • Type 2: Everything else. Move fast. Here's the kicker: 90% of your decisions are Type 2. But we treat them all like Type 1. Real Story: Three years ago, I watched a founder delay launch for 2 months to fix "critical" issues. Those issues? Users never noticed them. What they did notice? The competitor who launched first. Your Quick-Decision Playbook: 1. Set decision timeboxes ("We decide by Friday") 2. Use the 80/20 rule (80% right now beats 100% too late) 3. Run 2-week experiments 4. Create pivot-safety ("We can always adjust") 5. Ask: "What's truly irreversible here?" The Hidden Multiplier: When you start deciding faster, your entire team follows. They stop waiting for perfect information. They start moving forward. They take ownership. Because here's what 20 years of scaling tech teams taught me: The founder who made 100 good decisions will always outperform the one who made 20 perfect ones. Your move: What decision are you overthinking right now? Make the call. Your future self will thank you. #TechLeadership #StartupStrategy #Innovation

Ever wonder why some startups scale rapidly while others keep struggling, even when they have great ideas and funding? It’s not always about competition or market conditions. It’s often the founder’s hesitation to make decisions. I’ve seen brilliant entrepreneurs delay crucial choices—vision, hiring, pricing, fundraising, or pivoting—only to realize later that indecision cost them more than a wrong decision ever could. Why Do Entrepreneurs Procrastinate on Decisions? 1) Fear of failure – What if it’s the wrong choice? 2) Avoid discomfort – Difficult conversations and hard choices are postponed. 3) Overthinking (Analysis Paralysis) – Too much data, too many options. 4) Perfectionism – Waiting for the “perfect” answer that doesn’t exist. 5) Lack of prioritization – Everything feels urgent, but nothing moves forward. I’ve worked with countless entrepreneurs, and here’s what I’ve learned: Successful founders aren’t those who always make the "right" decisions. They are the ones who make decisions quickly, learn fast, and adapt. How to Break Free from Decision Paralysis 1) Use the 80/20 Rule: Focus on the few high-impact decisions that drive most results. 2) Set Decision Deadlines: Don’t keep options open forever—commit to a time frame. 3) Apply ‘Fail Fast, Learn Faster’ Thinking: Action beats hesitation. A bad decision can be corrected; no decision keeps you stuck. 4) Use Simple Frameworks: Eisenhower Matrix, RICE Scoring, or the One-Way vs. Two-Way Door Method. 5) Outsource or Delegate: Not all decisions need the founder’s involvement. Empower your team. 6) Done is Better Than Perfect: Perfectionism kills momentum. Execution is everything. Every delayed decision is an opportunity lost. Startups grow when founders move fast, test, iterate, and refine. What’s the one decision you’ve been procrastinating on? Make it today. #Entrepreneurship #DecisionMaking #StartupGrowth #Leadership

Fast thinking gets a bad rap. ‘Think like a startup’ sounds glib. ‘Move fast and break things’ sounds like an excuse for people who like to break things. So how do you do strategy at speed without the drama and the damage? I’ve been working with strategy projects with a fintech and a ventures lab - two organizations that instinctively run on speed - and we’ve found ways to be both fast and thoughtful. Genuine sprints. We get together for an hour to talk intensively about a specific slice of the problem and then write it up. We give ourselves 24 hours to work on something. We speak with an expert or a person working at the coal-face of the problem, who can make us smarter within a day. Having only a day to solve something builds intellectual openness into a project. I’ve covered a lot of ground - literally - with a client who enjoys a high-intensity discussion while speed-walking at a treadmill desk. Solve big strategic problems as product problems. Strategy is big and exploratory. Addressing it like a product problem can simplify it. Pin down a vague idea into a plan for a customer-facing product. Can we simplify this down to the problem we solve, and the people we solve it for? The Business Model Canvas helps here. It was created for startup businesses but it has clarifying powers for strategy projects in general. (Credit to Saneel Radia who sparked the idea of using the canvas as a strategy tool, and Sean Lyons who used to clarify airy 'what-if' business proposals at R/GA by asking how you could make them into a useful service for a client.) Reduce the homework. A deep 4Cs analysis is a beautiful thing. If you don’t have time for that depth, reduce the ask to what’s the most important thing to explore about the customer, the category or the culture? You need judgement or a theory of victory here, and it liberates the team when they are tasked to do less.  Be prepared to pivot. Sprints throw up discoveries, and a big discovery can send a project in a different direction. This is a good thing. The short lead time requires you to have breakthroughs and to act on them.  Be 80% right. Many strategists run on being right. Most businesses and business leaders run on momentum. (Felicia Zhang has written some great posts on this.) So the goal isn’t completeness or perfection, it’s having enough conviction to move forward. Be open about this trade-off, and be comfortable to be 80% right in 50% of the time. Fast strategy doesn't have to be sleeping-bags-in-the-office hardcore. It starts with honesty and openness, because you are consciously working with less. It takes collaboration between the client and the consultant because you both have to do the work. And it creates respect for others' time and energy, because sprint-paced work makes everyone’s time more precious. If you are a leader who needs to figure out a bigger future for their brand or business, we should be talking. Let’s do a quick Zoom or a philosopher’s walk.

The most important thing I’ve learned in the past three years of building startups is creating an unforgiving sense of urgency. Here’s what worked for me: 1. Force External Deadlines 🕰️ Self-imposed deadlines are easy to ignore. External deadlines aren’t. Example: If I promise a customer a feature by an upcoming date, we have to deliver—we’re not going to upset a customer. As Parkinson's Law goes, work will fill the time allotted for its completion—allot less time. 2. Exhaust Your Resources🪫 Do it now. I used to convince myself to “save” certain leads or delay a launch until the product was “better.” That was a mistake. If you do everything now, you can force yourself to scramble desperately in the future. Doing things now creates new opportunities in the future. Example: When acquiring our first customers, I hesitated on reaching out to people I had an edge with (alumni, friends, or warm intros) thinking I should wait for a perfect moment. No such thing existed, waiting just delayed progress. 3. Highlight a Lack of Progress ⚠️ In Y Combinator’s W25 batch, we have an extremely short window to launch one of the fastest-growing businesses in the world. Example: Ishan Sheth and I have a large TV constantly displaying our live-updating KPIs and metrics. If our growth is stagnant, it’s obvious, and the red target growth line almost gamifies hitting our goals. These are things that have worked so far, but we aren’t perfect. Would love to hear what has helped you stay productive? 👇

I used to be obsessed with staying organized. It was something I learned at my first job. I'd write detailed notes on everything, thinking I'd refer back to them later. This habit carried over into my work with startups. I've noticed something counterintuitive: the most organized founders aren't usually the ones making the most progress. It's often the ones who look unorganized but impatient who make real progress - those more concerned with doing than documenting. This approach can seem chaotic at first, like a drunk stumbling home. But patterns in startups emerge only in hindsight. Startups don't fit neatly into frameworks or pre-written plans. Investors might be able to work in small, intense periods to hunt and relax later like lions, but founders are more like sharks. Stop moving, and you die. In the uncertain world of startups, constant motion is key. This is especially true for those before product-market fit. Be wary of the person who takes too many notes (even if that person is you). It often signals a desire for certainty in an inherently uncertain process. Instead, cultivate urgency. When you think of something that needs doing, do it immediately. Don't write it down for later. My thinking has shifted so much that I now get concerned when I meet overly diligent note-takers. Others might praise their thoroughness, but now I see a red flag. Does this mean all documentation is bad? Of course not. Some level of organization is necessary. The key is finding the right balance - enough structure to keep you on track, but not so much that it becomes a crutch or a distraction from actual progress. Think of it this way: in a startup, action creates information. The more you do, the more you learn. Excessive planning or note-taking can become a form of procrastination, a way to feel productive without taking real risks. The best founders I've worked with have a bias towards action. They're comfortable with ambiguity and willing to course-correct on the fly. They document just enough to communicate effectively with their team and stakeholders, but no more. This approach requires a certain comfort with chaos. It means accepting that you'll make mistakes and have to backtrack sometimes. But it also allows for the speed and flexibility that startups need to survive and thrive. So if you find yourself spending more time organizing your thoughts than acting on them, it might be time to reassess. Put down the notebook, step away from the productivity apps, and go do something - anything - to move your startup forward. The insights you gain from action will be far more valuable than any notes you could write. Would that leave you more worked up ? Yes. But startups before product-market fit are that way.

Want to 10x your productivity at work? Here's what I learned from scaling 7-figure startups (that most employees miss): -- After years of growing bootstrapped brands... I've noticed something fascinating: The same principles that keep scrappy startups alive can transform your corporate performance. Here are 3 unconventional efficiency plays that startups use daily: -- 1. The "MVP Meeting" Startups can't afford endless meetings. Instead of hour-long sessions with 12 people, they do 15-minute standups with only decision-makers. Try this: Before accepting a meeting, ask: → "Could this be an email?" → "Do I need to stay the whole time?" → "Who actually needs to be there with us?" -- 2. The "Death to Perfect" Rule In startups, speed beats perfection. Rather than spend weeks polishing a presentation, they ship a "good enough" version and iterate based on feedback. Translation for corporate: Set a time limit for tasks. When it hits, ship what you have. Perfect is the enemy of done. -- 3. The "Zero Inbox" Myth Successful startups ignore 80% of their inputs to focus on the vital 20%. They know most "urgent" emails aren't actually urgent. Try this: Check your email 2x/day. Everything else? It can wait. Corporate life doesn't have to mean corporate speed. Sometimes the best way to climb the ladder is to act like there isn't one. -- Want more unconventional strategies to accelerate your career? Follow me → Ian Sells