What I’d tell myself about startups if I could go back 5 years.

What I’d tell myself about startups if I could go back 5 years.

What I’d Tell My Startup-Early Self (If I Could Go Back Five Years)

From /r/entrepreneur, with no endorsement of the author

This piece captures, in no particular order, the lessons I’d share with my younger self about starting and growing startups. It’s not a how-to or formal advice; it’s a reflection directed at me, with the understanding that I’ve learned much along the way. Grammar is hard.

Key lessons and observations

  • You’ll likely build too much and ship too late. Make it a top priority to prevent that.
  • Competition isn’t a barrier; someone else working on the same idea isn’t a problem.
  • Don’t sign NDAs before hearing an idea.
  • Networking in London (and many places) often centers around social drinking. Find a way to engage without the recurring hangover.
  • The most productive people aren’t the ones who are always out for drinks.
  • Linear growth can be worse than no growth.
  • Many who preach “fail fast” aren’t truly practicing it.
  • It’s easy to mistake customer development for bending feedback to fit your preconceptions.
  • People hide a lot of unused domain names; recognize this in conversations about branding.
  • It’s easy to be hyper-critical and dismissive. Don’t be lazy about evaluating ideas.
  • When engaging with newcomers, call out unhelpful dismissiveness and stay constructive.
  • It’s tough to stay focused on difference-making insights when you’ve seen similar pitches fail before.
  • A technically competent developer doesn’t automatically know how to ship. Prioritize shipping capability.
  • Language and framework debates are fine for conversation, but often don’t translate to real-world value.
  • A good developer can learn a new language or platform quickly.
  • Investor experience is still largely a gap for me.
  • Exaggerated early success is exhausting and makes genuine wins harder to celebrate publicly.
  • Deep personal investment in the problem is a strong predictor of product viability.
  • Falling in love with a product rather than the problem is dangerous.
  • You can skip knowing every technical detail (like hash tables); learning them can be satisfying later.
  • The same goes for Big O notation.
  • Overnight success is a rarity; even iconic stories like The Social Network are exceptions.
  • PR remains perplexing to me.
  • Most technical solutions are easier than getting the product into users’ hands.
  • Make something people want is a useful heuristic, but not universal. Sometimes, making what you want matters too.
  • Your personal appeal doesn’t guarantee broad market demand.
  • If you lack firsthand experience in an industry, you’re likely to be wrong about how it works and what problems to solve. Talk to real people.
  • Advertising is a fragile business model; it often signals trouble for monetization.
  • “We’ll monetize the data” is the new “Ads.”
  • The people you want to collaborate with are those who consistently look for ways to help you.
  • Be proactive about asking for things. Most people will offer discounts or introductions if you ask.
  • Learn to say no—to discounts, to time-wasting projects, to opportunities that don’t align with your focus.
  • Consider pivots that make solid business sense, even if they lead to a product you care less about.
  • Writing—whether blogs, books, or journaling—has many positive effects.
  • Don’t obsess over internet feedback about every sentence you publish; trolls exist.
  • A single troll can overshadow many positive interactions. Protect your communities from them.
  • If you’re pitching over coffee, request to hear the other person’s pitch after you’ve shared yours.
  • Only promise introductions or deliverables you will actually follow through on.
  • Demonstrate rather than tell: a tangible, imperfect product that works beats grand promises.
  • Building things is exciting; don’t let an obsession with “Lean Startup” or landing pages overshadow actual creation.
  • Lean Startup offers useful ideas, but treat it as a pamphlet rather than a complete guide; consider more robust reads.
  • Much startup advice is variable; trust your gut, but be willing to question it.
  • When it comes to customer needs, though, listen to them—don’t rely solely on your own intuition.
  • Bitcoin ATMs are rarely used for practical purposes.
  • Sketch out back-of-the-napkin financial forecasts for each business model to sanity-check potential viability.
  • Be cautious about dismissing conversations that begin with “I’m looking for a technical co-founder.” You may miss valuable connections; clarify your role early.
  • Fundraising and accelerators demand significant time. Often, you must choose between building and fundraising—lean toward building when in doubt.
  • Not all problems require technical solutions; apps aren’t a universal answer.
  • “Facebook is the Facebook for X” is a common framing; many categories exist in parallel.
  • An idea dismissed at a hackathon may outlive the venture you ultimately pursue.
  • Genuine failures aren’t celebrated by those who embrace them; there aren’t people who truly enjoy failing.
  • Your claim to “your idea” only exists once you’ve shipped something; otherwise, the credit goes to broader innovations.
  • People don’t steal ideas; share broadly. Avoid NDAs when presenting ideas to preserve credibility.
  • Friendship is not automatically equivalent to effective collaboration.
  • Small teams can move quickly; be careful about adding people when speed and agility matter.
  • Multitasking isn’t effective; focus on one task at a time and minimize interruptions.
  • Read Paul Graham’s essays for perspective and guidance.
  • General tech news offers limited return on time; prioritize books and meaningful conversations.
  • Explore founder stories, Fool’s by Randomness, and The Four Steps to the Epiphany for deeper insight.
  • A simple, text-based logo can be sufficient early on; don’t overemphasize branding initially.
  • Open source and share side projects when possible; you’ll encounter valuable connections.
  • Sustained 12-hour days are rarely productive; seek ways to optimize your workflow.
  • Engage with a broad audience; talk to everyone.

Source: originally posted at talkingquickly.co.uk

Note: This rephrased article preserves the core insights from the original post while presenting them in a professional blog format suitable for a WordPress publication.

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