What I’ve learned in 20+ years of building startups

What I've learned in 20+ years of building startups.
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What I’ve learned in 20+ years of building startups…

In the fast-paced world of startups, two decades of experience can teach you invaluable lessons. From the trenches of entrepreneurial ventures, here are the distilled wisdom and key takeaways from a seasoned startup veteran’s 20-plus-year journey.

What I've learned in 20+ years of building startups
What I’ve learned in 20+ years of building startups

What I’ve learned in 20+ years of building startups – Summary: The journey of building startups for over 20 years has yielded several crucial lessons:

  1. Fail Well: Failure is a common part of the startup process, with success in only a fraction of attempts. It’s important to accept failure as a stepping stone.
  2. Persistence: The key to overall success often lies in sheer perseverance and the refusal to quit, even in the face of early failures.
  3. The Power of ‘No’: Turning down opportunities, especially during financially tough times, is crucial to avoid burnout and stay true to your goals.
  4. Work Smart and Hard: While enjoying your work is vital, readiness to put in extra effort when needed is equally important.
  5. Start Slowly: For new businesses, especially online, it’s advisable to start small and avoid getting entangled in bureaucracy before proving the business model.
  6. Be Cautious with Growth: Rapid expansion can lead to financial strain. It’s better to grow at a sustainable pace.
  7. Avoid Corporate Pitfalls: As businesses grow, maintaining a customer-centric and enjoyable work culture is essential, avoiding the trap of becoming overly corporate.
  8. Embrace Remote Work: If possible, allowing remote work can save costs and increase employee productivity.
  9. Simplicity in Tools: Using too many apps and tools can be counterproductive. Stick to a few that work best for your team.
  10. Maintain Relationships: Keeping doors open with past collaborators is crucial, as business landscapes and relationships are ever-changing.

What I’ve learned in 20+ years of building startups – Lessons Learned in Detail

  1. Fail Well. You’ve heard it a million times before: ideas are easy; execution is hard. Execution is incredibly hard. And even if something works well for a while, it might not work sustainably forever. I fail a lot. I’d say my ideas are successful maybe 2/10 times, and that’s probably going easy on myself.

  2. Keep Going. The difference between overall success and failure, is usually as simple as not quitting. Most people don’t have the stomach for point #1 and give up way too quickly.

  3. Saying No. Especially if you didn’t have a particularly good month and it’s coming up on the 1st (bill time), it’s hard to say “No” to new income, but if you know it’s something you’ll hate doing, it could be better in the long-run to not take it or else face getting burnt out.

  4. Work Smart (and sometimes hard). I would hazard to guess that most of us do this because we hate the limitations and grind of the traditional 9-5? Most of us are more likely to be accused of being workaholics rather than being allergic to hard work, but it certainly helps if you enjoy what you do. That said, it can’t be cushy all the time. Sometimes you gotta put in a little elbow grease.

  5. Start Slow. I’ve helped many clients start their own businesses and I always try to urge them to pace themselves. They want instant results and they put the cart before the horse. Especially for online businesses, you don’t need a business license, LLC, trademark, lawyer, and an accountant before you’ve even made your first dollar! Prove that the thing actually works and is making enough money before worrying about all the red tape.

  6. Slow Down Again (when things start to go well). Most company owners get overly excited when things start to go well, start hiring more people, doing whatever they can to pour fuel on the fire, but usually end up suffocating the fire instead. Wait, just wait. Things might plateau or take a dip and suddenly you’re hemorrhaging money.

  7. Fancy Titles. At a certain stage of growth, egos shift, money changes people. What was once a customer-centric company that was fun to work at becomes more corporate by the day. Just because “that’s the way they’ve always done it” in terms of the structure of dino corps of old, that’s never a good reason to keep doing it that way.

  8. Stay Home. If your employee’s work can be done remotely, why are you wasting all that money on office space just to stress your workers out with commute and being somewhere they resent being, which studies have shown only make them less productive anyway?

  9. Keep it Simple. Don’t follow trends and sign you or your team up for every new tool or app that comes along just because they’re popular. Basecamp, Slack, Signal, HubSpot, Hootsuite, Google Workspace, Zoom (I despise Zoom), etc. More apps doesn’t mean more organization. Pick one or two options and use them to their full potential.

  10. Keep Doors Open. While you’ll inevitably become too busy to say “Yes” to everything, try to keep doors open for everyone you’ve already established a beneficial working relationship with. Nothing lasts forever, and that might be the lesson I learned the harshest way of all. More on that below…


What I’ve learned in 20+ years of building startups: A personal note that might be helpful to anyone who’s struggling

Some years back (around 2015), we sold the company my partner and I built that was paying our salaries. During those years, I closed a lot of doors, especially with clients because I was cushy with my salary, and didn’t want to spend time on other relationships and hustles I previously built up over the years.

I had a really rough few years after we sold and the money ran out where I almost threw in the towel and went back to a traditional 9-5 job. I could barely scrape rent together and went without groceries for longer than I’m comfortable admitting.

There’s no shame in doing what you’ve gotta do to keep food on the table, but the thought of “going back” was deeply depressing for me. Luckily, I managed to struggle my way through, building up clients again.

What I’ve learned in 20+ years of building startups – Conclusion:

Navigating the world of startups requires a balance of resilience, strategic decision-making, and adaptability. The lessons learned over two decades in the startup ecosystem are not just strategies but guiding principles for sustainable success and growth in the dynamic world of entrepreneurship.


If you’re curious about how I make money, most of it has been made building custom products for WordPress.

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Source: r/Entrepreneur

What I’ve learned in 20+ years of building startups – References:

  1. Entrepreneurship Blogs and Websites: Look for blogs from successful entrepreneurs or business coaches. Sites like Entrepreneur (entrepreneur.com), Forbes Entrepreneurs Section (https://forbes.com/entrepreneurs), and Harvard Business Review (hbr.org) often have valuable articles on startup strategies and entrepreneurial journeys.
  2. Startup Case Studies: Websites like Inc. Magazine (inc.com) and Fast Company (fastcompany.com) frequently publish case studies and stories about startups and entrepreneurial experiences.
  3. Business and Tech News Websites: Platforms like TechCrunch (techcrunch.com), Business Insider (businessinsider.com), and The Wall Street Journal’s Business section (https://wsj.com/news/business) are good for staying updated on the latest in startup trends and business strategies.
  4. Remote Work and Productivity Tools Blogs: For insights on remote work and productivity tools, check out blogs from companies like Basecamp (basecamp.com), Slack (https://slack.com/blog), and Zoom (blog.zoom.us).
  5. Online Business Forums and Communities: Websites like Reddit’s Entrepreneur subreddit (https://reddit.com/r/Entrepreneur) or startup-focused forums on sites like Quora (quora.com) can provide real-world advice and experiences from various business owners.
  6. LinkedIn Articles and Thought Leaders: Following successful entrepreneurs and business thought leaders on LinkedIn can provide you with a plethora of insights and firsthand accounts of business experiences.
  7. Business and Entrepreneurship Books: Websites of authors who have written extensively on startups and entrepreneurship, such as Guy Kawasaki or Seth Godin, often have blogs and articles that are invaluable to entrepreneurs.

Examining the Fragmented Data on Black Entrepreneurship in North America

Entrepreneur Our community brings together individuals driven by a shared commitment to problem-solving, professional networking, and collaborative innovation, all with the goal of making a positive impact. We welcome a diverse range of pursuits, from side projects and small businesses to venture-backed startups and solo ventures. However, this is a space for genuine connection and exchange of ideas, not self-promotion. Please refrain from promoting personal blogs, consulting services, books, MLMs, opinions.

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When people search "Adobe alternative" or "lightweight PDF editor" - they find these directories first, not my website. Result: Steady stream of 50-100 downloads per day just from directories. Lesson: SEO isn't just Google. Be discoverable where your users are searching. REDDIT (Organic Comments) (~2,200 downloads) Not posting "Check out my product!" Just being helpful in r/productivity, r/software threads where people ask "What PDF editor do you use?" I'd share my experience, mention alternatives including mine, and let them decide. Result: People checked it out because I was helpful first, promotional never. Lesson: Distribution = being present where your users have problems. Not announcing where you want attention. WORD OF MOUTH (~1,000 downloads) The unsexy one that compounds: - Students sharing in college WhatsApp groups - People recommending in forums - Reviews mentioning it Takes time but becomes self-sustaining. --- THE PATTERN I'M SEEING Distribution channels I can't control (others' tweets, blogs finding me, directories, word of mouth) >>> channels I can control (my tweets, paid ads, official launches). You can't force organic growth. But solve a real problem well, and people will talk about it. --- CURRENT METRICS (Full Transparency) Revenue: ~$500/month (~50 paid users at $10 one-time purchase) Downloads: 10,000+ total (across all platforms) Time to build: ~10 months (nights/weekends while working day job) Marketing spend: $0 Team: Just me Funding: $0 (bootstrapped) Geographic breakdown: - 40% Germany/Austria/Switzerland (DACH region) - 35% India - 15% USA - 10% Rest of world Platform breakdown: - 60% Desktop (Windows/Mac/Linux) - completely free - 40% Mobile (iOS/Android) - freemium --- WHAT I'M LEARNING PRODUCT-MARKET FIT > MARKETING Users market products that solve real problems. You don't need to. GEOGRAPHIC ARBITRAGE IS REAL Biggest market: Germany My location: Not Germany My German language skills: Zero Built for global market with strong principles (privacy, offline-first). Germans loved it. Now I'm learning German and translating the app. Sometimes your product finds its market before you do. 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  • Happy that I survived the darkest place in life.
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  • "Build in Public" is the biggest lie indie hackers tell themselves. Here's what nobody wants to admit.
    by /u/Obvious_Cheetah240 on February 15, 2026 at 4:08 pm

    I need to get something off my chest because I keep seeing the same pattern over and over again and it's painful to watch. Every single day in this sub someone posts something like "I've been building in public for 6 months and I have zero customers. What am I doing wrong?" And every single time the comments say the same thing. Be more consistent. Post more often. Share more updates. Be more vulnerable. That advice is wrong. Not because consistency doesn't matter but because it completely misses the actual problem. Here it is and it's going to sting a little. Building in public is not a growth strategy. It never was. It's a trust mechanism that most people are using as their ENTIRE go to market plan. And that's why it's not working. Let me explain what I mean. When you post "just hit $2K MRR" on Twitter you know who cares about that? Other indie hackers. Not your customers. Your customers are not scrolling Twitter looking for someone's revenue milestone to decide which tool to buy. They're googling their problem. They're asking in Slack communities. They're reading comparison posts on Reddit. They're clicking ads. They're finding you through a friend who told them about you. That's distribution. And it's a completely different game from building in public. I started paying attention to which founders in these communities were actually growing versus which ones were just getting likes. And the difference was dead simple. The ones who were growing had something running underneath the public content. Always. One had built 40 programmatic SEO pages targeting long tail keywords. Another had partnered with three complementary tools and they were sending each other users. Another was active in five niche communities where her target customers actually hung out and she was helping people genuinely without ever pitching. Another had a simple referral program where existing users got a free month for inviting someone. The public building part made all of that work better. When someone googled them they found a real human with a real story. When they landed on the site they already felt like they knew the founder. When they got a cold email it didn't feel cold because they had seen this person's journey somewhere before. That's what building in public actually does. It's the trust layer. It's the warmth. It's the thing that makes every other channel convert higher. But it is not the channel itself. Here's the framework I keep coming back to. Step one. Share the problem you solve not what you shipped. Nobody cares about your new feature. They care about the pain it fixes. Talk about the pain. Step two. Document your decisions not just your results. "We chose to go freemium and here's why" is a hundred times more valuable than "we launched a free plan." One teaches. The other is just an announcement. Step three. Make content that helps people who have never heard of you. This is the big one. If your content only makes sense to people who already follow your journey it cannot spread. It has no legs. But if you write "I tested four pricing strategies in 30 days and here's what happened to conversion rates" that's useful to literally every founder on earth. That gets shared in places you'll never even see. Step four. Pick one real distribution channel and go deep. SEO. Partnerships. Communities. Cold outreach. Affiliates. Pick one. Get good at it. Build in public makes it work better but it cannot replace it. Step five. Send every single piece of attention to one place. One landing page. One email list. One waitlist. If you have followers but no funnel you're collecting applause not customers. I know this might sound harsh but I genuinely think this reframe could save some of you months of frustration. I was stuck in the same loop for a long time. Posting updates. Getting likes. Watching the signup page stay flat. The moment I started treating BIP as the amplifier instead of the strategy everything changed. One more thing for anyone building AI products right now. You have a window that won't stay open forever. People are insanely curious about AI tools and how they work. The content almost writes itself. But that window will close as the market matures and the novelty fades. If you're building AI and you're not stacking a real distribution channel underneath your public content right now you're going to look back and wish you had. Alright that's my rant. I'm curious what you all think. Am I wrong? What's actually working for you right now in terms of real distribution not just visibility? And for those of you who are in the middle of building something I genuinely want to hear what you're working on and what your biggest distribution challenge is. Happy to think through it with you. submitted by /u/Obvious_Cheetah240 [link] [comments]

  • What is the most valuable skill you learned in business?
    by /u/victorious02 on February 15, 2026 at 4:03 pm

    I've been wondering what is the #1 thing you need in business in your opinion. I know it's complex question and you need so many things , but let's see if you have to pick one. submitted by /u/victorious02 [link] [comments]

  • How do I not lose motivation?
    by /u/rmx2501999 on February 15, 2026 at 3:41 pm

    I come here now pretty frequently, I don’t really have anyone else to turn to business wise. I kinda already know the answer, that should focus on small wins and such but I can feel pretty big mood swings thru out the day and it’s a emotional rollercoaster. Is this only me or have other people learnt to deal with it better? submitted by /u/rmx2501999 [link] [comments]

  • Technician Developer in Sales. How to start search B2B client on my product ?
    by /u/bgdn21 on February 15, 2026 at 3:39 pm

    Hello to everyone who works for themselves and has gone through the valley of death of projects every single day. I am a developer who has worked for a long time in various software development companies. Of course, I was in constant contact with software customers, but only in the form of receiving feedback and adding new features. Recently, a friend of mine approached me, who in fact became my first customer and ideological inspirer in this direction. The development of program that allowed him to generate hundreds of B2B leads according to keywords. That is, he was able to quickly obtain a number, email, and name in a specific locality. Yes it use compilation in several social media, map and website. Yes it cold leads, but they have a calling managers and startegy how to convert into sale. So I started thinking about where to find other people who might be interested in this software or generating leads for themselves. I had never sold anything before, never approached it from a sales perspective, and never thought about it. There is Upwork and Fiverr, but now they are literally flooded with people who are ready to sell junk, and the reputation of the work there is quite low. What would you recommend, perhaps a platform, interaction with an agency, or something else? submitted by /u/bgdn21 [link] [comments]

  • Can you be an entrepreneur without getting rich?
    by /u/pleasedontjudgeme13 on February 15, 2026 at 2:14 pm

    I’m taking an entrepreneur course and he keeps pushing this idea of you need to appeal as many people as possible, you need to expand and commercialize and you to make as much money as possible. I’d much rather run an honest business that’s focused on providing a service I know does good for people. I don’t need to hire anyone. I teach people how to regain agency. Every student becomes their own teacher. It benefits myself when I teach. I have no interest in persuading, triggering emotions, becoming an influencer, having authority over others. Those things are contrary to what I teach. I could easily lie to my students. Promise things I don’t deliver. Appeal to emotion rather than reason. I’m not interested in that anymore (easier said than done). So I’m curious, does this approach still makes me an entrepreneur? submitted by /u/pleasedontjudgeme13 [link] [comments]

  • Building the product was the easy part. Finding the first 10 customers is breaking me.
    by /u/augusto-chirico on February 15, 2026 at 2:09 pm

    I shipped a working product in a few weeks. Between Claude, Cursor, and everything else out there, the technical part almost felt too easy. Features that would've taken me months a year ago just... happened. And then I hit the wall that no AI tool can solve. I've been sitting on a product that works, that people told me they'd pay for, and I still can't seem to get those first real customers through the door. Not friends who "check it out" as a favor. Actual strangers who find it, try it, and decide it's worth their money. The weird part is I know more about marketing strategies than I've ever known. I've read every thread on here, every twitter thread from founders who "cracked distribution," every indie hackers post about cold outreach and SEO and building in public. I probably know more about customer acquisition theory than most marketing graduates at this point. And yet I'm paralyzed. Because every strategy contradicts the last one. One person swears by cold email, the next says it's dead. Someone built their whole business on SEO, someone else says it takes too long in 2026. Build in public works until you realize your audience is just other founders building in public. I think the real problem is that I keep reading instead of doing. It's comfortable to research because it feels productive without the risk of putting yourself out there and getting ignored. Building was safe because I'm good at it. Distribution means being bad at something again, and after 20+ years of coding that's a hard place to be. Curious if other technical founders went through this same loop. Not looking for strategy recommendations honestly - more wondering how you actually broke out of the overthinking and just started doing something, even if it was wrong. submitted by /u/augusto-chirico [link] [comments]

  • Founders, what's one thing you do all day that feels productive but probably isn't?
    by /u/Vanie429 on February 15, 2026 at 1:50 pm

    I'll go first. I spend way too much time "organizing." Rearranging my task list. Cleaning up my notes. Making things tidy. It feels like progress because I'm moving things around. But nothing actually moves forward. I'm trying to catch myself when I do this now. If I can't draw a line from the task to something that matters in a week, it's probably just expensive busywork. What's your version of this? submitted by /u/Vanie429 [link] [comments]

  • Anyone else feel like managing employees takes more time than actually running the business?
    by /u/ElDiegod on February 15, 2026 at 1:50 pm

    I spend more time on scheduling, time off requests, and shift swaps than I do on anything that actually grows the business. Some weeks it feels like I'm a full-time HR department that occasionally does revenue-generating work on the side. I have 22 employees across two locations. Between figuring out who can work when, dealing with last-minute changes, and making sure I'm not accidentally scheduling someone into overtime, it eats hours every week. Is this just what it is at this size or am I doing something wrong? submitted by /u/ElDiegod [link] [comments]

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