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.

  • I'm building a social platform for students, how do I get my first real users?
    by /u/hvi-13 on March 9, 2026 at 4:35 am

    The Backstory: I'm a 17 year old guy who is highly introverted. I quit traditional studying routes because of my mental health and chose homeschooling. Things were going fine but as the exam pressure came on, I started struggling with managing time and connecting with my friends (social media is where I mostly interact with people), which ended up with me ruining a very important olympiad I was preparing from months. After that I decided to create some kind of software which could help me track my studying habits, increase my study time, help me memorise stuff, and create structured data of how my studies are improving or declining. But social media was still something which stole most of my day, so I've spent the last several weeks drafting an idea, building a social platform aimed at students and those who are sitting high-stakes exams (think A-Levels, JEE, GCSE, SAT, IB, etc. around the world). The core idea is that studying is one of the most isolating things a student goes through and there's no platform built around that experience. Every existing study app is just a timer. Every social app pulls attention away from the work. I'm building something that would really help students improve their study quality while being on a social platform which is not designed to make them doom scroll for hours. I have a product direction and I've been actively coding the webapp myself. Here's where I'm stuck: I have zero marketing experience and honestly the social/community side is not my strong suit at all, kind of ironic considering what I'm building. The app is still early stage but before launching I really want to build a small community of people who would genuinely use the app and give real honest feedback, not just sign up and disappear. How would you go about finding those first real users before launch? submitted by /u/hvi-13 [link] [comments]

  • Complete Case Study of Cursor: How an AI Coding Tool Quietly Became One of the Fastest Growing SaaS Products
    by /u/HomeworkHQ on March 9, 2026 at 4:00 am

    Every once in a while a product appears that feels obvious in hindsight but almost nobody saw coming early enough. Cursor is one of those products. On the surface it is simple to describe. Cursor is an AI powered coding environment that helps developers write, edit, and understand code using natural language. You can ask it to refactor functions, generate features, debug logic, or explain unfamiliar codebases. It feels less like a traditional IDE and more like sitting next to an extremely capable engineer who never gets tired. But the real story is not the technology. The real story is the problem it solved. Software development has always been limited by time and cognitive load. Even experienced developers spend huge amounts of time searching documentation, debugging small issues, or navigating large codebases. Cursor did not try to reinvent programming. It simply removed friction from the daily workflow developers already had. And that decision mattered. Instead of targeting a niche or a new category, Cursor inserted itself directly into one of the largest professional markets in the world. Millions of developers already work inside coding environments every day. By improving that environment even slightly, Cursor became instantly valuable. Another reason Cursor grew quickly is distribution. Developers are one of the most networked communities online. When something genuinely useful appears, it spreads through GitHub repos, Discord servers, engineering Slack groups, and technical Twitter within days. Cursor benefited from exactly that effect. Engineers shared it with other engineers because it actually saved time. What makes this story interesting for founders is not just the growth. It is the lesson behind it. Cursor did not win because of marketing tricks or viral gimmicks. It won because it started with the right problem. Once that happens, distribution, adoption, and revenue become much easier to unlock. And this is where most startups fail. Many founders start with a solution first and then try to search for a problem later. Cursor did the opposite. It focused on a pain point that already existed at massive scale and then built something that made developers immediately more productive. Finding that kind of problem is often the hardest part of building a company. Today there are entire communities and platforms built around discovering startup opportunities before they become obvious. One example is StartupIdeasDB which curates startup ideas, emerging trends, and real world problem spaces founders can explore. Platforms like this are becoming increasingly important because they help founders focus on the most critical step in entrepreneurship which is choosing the right problem to solve in the first place. In many ways the biggest advantage a startup can have is not funding, code, or even talent. It is starting with the right idea at the right time. Cursor is a strong reminder of that principle. A product that improves the daily workflow of millions of developers by even a small margin can become an enormous business surprisingly fast. And this is exactly why its story is worth studying. Because sometimes the difference between a small project and a massive company is simply starting with the right problem. We will come back to Cursor again later and break down more details about its growth and product decisions. For now this is just the beginning. Case Study 1 of 25 (2026). submitted by /u/HomeworkHQ [link] [comments]

  • How do I price a client who left me for a larger company?
    by /u/AtlasSEOGuy on March 9, 2026 at 3:18 am

    So this is a pretty classic story. I had a client, now an ex-client, who worked with me when his roofing company was still very small and just getting started. I was actually the first person he ever hired for SEO, and honestly, he was also one of the first clients I had when I started my agency, so I’ve always had a bit of a soft spot for him. I won’t get into every month of the working relationship, but within about a year we had already pretty much dominated his core local area and started looking at expansion. The problem was that expanding into new areas was a lot slower than the initial growth. Some of that came down to proximity, some of it was because the new markets were more competitive, and a big part of it was simply that there was only so much we could realistically do on a small budget. I explained all of that to him and told him that if he wanted to seriously expand, he’d need to increase his budget. Instead of doing that, he decided to leave. Then about a year later, he texted me asking to meet. During that meeting, he told me he had hired another company, they charged him about double what I had originally asked for, and the whole thing turned into a disaster. Not only did they fail to deliver, but he said they even tanked some of the rankings he used to have. Now he wants to come back, and he’s asking for the same original price I quoted back when we first discussed expansion. I don’t dislike the guy, but I’d be lying if I said part of me wasn’t frustrated that he walked away over budget, paid someone else more, and still ended up worse off. So now I’m torn. Do I honor the old price, or do I raise it knowing he was clearly willing to pay more? What would you do? submitted by /u/AtlasSEOGuy [link] [comments]

  • I rebuilt my entire nurture sequence around one psychological principle and conversions tripled in 6 weeks
    by /u/Jumpy_Examination470 on March 8, 2026 at 10:15 pm

    For like 6 months my nurture sequence was basically a glorified newsletter. Decent open rates. Almost zero conversions. Then I rebuilt the whole thing around one psychological principle and everything changed. The principle is anticipated regret. And it's different from what most people think of when they hear "urgency" or "scarcity." Anticipated regret is the feeling a person gets when they imagine a future version of themselves that did not take the action they're currently considering. It's not about missing a deadline or a limited offer. It's about picturing yourself 90 days from now still stuck in the exact same place doing the exact same things. When you show someone an aspirational outcome a lifestyle, a revenue number, a transformation you activate desire. Which is positive and motivating but also easy to defer. People scroll past desire all day long. But when you show someone a vivid specific picture of where they will be in 90 days if they don't take action, you activate something much harder to ignore. The brain is wired to avoid imagined future pain more strongly than it pursues imagined future gain. So I rebuilt the sequence into four phases. Phase one is the regret activation opening. First message goes out within minutes of opting in. Not a welcome email and a free resource. A specific, conversational picture of what staying exactly where they are looks like in 90 days. No hard sell. No link. Just an emotional anchor. Something like: you found this because something about where your business is right now isn't sitting right. The honest version of what happens if nothing changes in the next 90 days is you'll still be posting every day, still getting followers, still closing the occasional sale, and still stuck in the same range because the thing keeping you there isn't effort, it's infrastructure. I send the sms version 5-10 minutes after the email. Two to three sentences. Pattern interrupt. Phase two runs days 2 through 10. Value escalation with anonymized client proof. Real useful content people can apply immediately. Not teaser stuff that withholds the key insight. But every piece connects back to the regret anchor from phase one. The anonymized stories with very specific internal details exact revenue numbers, exact problems, exact mechanisms - actually feel more credible than polished named testimonials because they read like something someone would share privately. The trigger is personalized based on what they engaged with. If someone replied about attribution tracking in phase two, the phase four message references that reply. The AI layer handles the conditional logic. No countdown timers. No fake scarcity. Just a natural transition that feels earned. The most common mistake is selling on day 3 or 4. That's proposing marriage on a first date. The timing isn't wrong because the offer is wrong. It's wrong because the relationship hasn't developed enough to support it. Email is the value delivery channel. SMS is the pattern interrupt channel. Don't use them interchangeably. Phase three is days 10 through 18. Authority positioning and community teasing. The goal is shifting perception from "person who sends useful emails" to "person who built something I want to be part of." I describe specific interactions that happen inside the community. Not a feature list. A story about twelve people jumping in to help someone with a specific objection within two hours. Phase four is the high ticket trigger. Days 18 through 45. And the reason it works is that by this point the reader has had weeks of genuine value, the regret response has been periodically reinforced, and they have a real picture of the community. submitted by /u/Jumpy_Examination470 [link] [comments]

  • How can I train my mind to become more entrepreneurial?
    by /u/Supermacropenis on March 8, 2026 at 9:29 pm

    I’m 26, and I’ve always wanted to be an entrepreneur. Trouble is, I’ve also always known that I’m just not entrepreneur minded. I don’t have those sorts of ideas that successful entrepreneurs do. I’ve got mates who are hustlers and don’t have issues making money through entrepreneurial means, but I just can’t seem to think that way. Are there any books out there that can change my mindset? Is it just the case that not everyone is cut out to be an entrepreneur? submitted by /u/Supermacropenis [link] [comments]

  • Most entrepreneurs are not building businesses. They are building paid features.
    by /u/AdPresent2493 on March 8, 2026 at 9:27 pm

    Hot take: a lot of “business ideas” are not actually businesses. They are useful little features attached to mildly annoying problems. And I think a lot of founders confuse “people like this” with “people will pay for this consistently.” I’ve been thinking a lot about the difference between: a real painful workflow problem a small convenience a feature that only makes sense inside a bigger platform For example, in ecommerce there are a lot of repetitive visual tasks that clearly matter, but each one by itself can feel too small to deserve a standalone subscription. That raises a bigger question: When does a narrow pain point become a real business, and when is it just a nice feature? My current belief is that a standalone product only works when at least one of these is true: it saves meaningful time repeatedly it clearly makes or saves money it removes a frustrating bottleneck it becomes part of someone’s habitual workflow Otherwise, founders may just be packaging convenience and hoping marketing carries the rest. Curious how other people here think about this. Where do you draw the line between: a real business and a polished feature with a billing page? Supporting example: PriceTagGenerator submitted by /u/AdPresent2493 [link] [comments]

  • DFY AI operations for solopreneurs?
    by /u/wasayybuildz on March 8, 2026 at 8:39 pm

    For a months now I've been keeping myself up to date with latest AI orchestration tools and more interested in how they work together. Like there's a difference between traditional chatbot that someone shows off once and then forgets about and an actual system that handles tasks perform actions when you're not around like openclaw. The thing I keep running into is that most people selling "AI" are selling features. What actually helps is when it works like a hire. It needs to have memory make judgments hand off tasks and understand context without resetting every time. That's the area I want to work in and prob achieve this by building on top of openclaw, like creating and giving it access to skills personalized for businessess. There is already a lot of github repos scattered around which I could aggregate for them based on their workflows . The people I think this would work for are already making money but are drowning in repetitive tasks and are non-terchnical. They've hit a ceiling and can't hire anyone don't want to manage an assistant and definitely don't want to learn another tool. if you're this person or have worked closely with someone like this would love to chat! submitted by /u/wasayybuildz [link] [comments]

  • First and only client left because results were too good, looking for encouragement
    by /u/asdfgh7777 on March 8, 2026 at 6:10 pm

    Marketing agency business here with a recurring payments business model. I'm back to 0 revenue. My first client left because they reached full capacity and simply don't wanna hire more employees to grow. Moreover, they even lied in the qualification phase and said they will start hiring once they reach 70% capacity. The fact that they lied even kind of hurt me because I outlined in the very first calls that our collaboration should be based on transparency... I've aleeady asked for referrals but didn't get any. I know I have to keep going with outreach, but morale took a hit. Would appreciate any advice and encouragement! submitted by /u/asdfgh7777 [link] [comments]

  • Are people here also noticing more inauthentic content in startup subreddits?
    by /u/Outrageous_Guess_962 on March 8, 2026 at 5:59 pm

    I’ve been noticing more posts/comments that feel off lately like ist not always obvious spam, not always obvious ads, but content that seems overly polished, agenda-driven, self-promotional, or possibly AI-assisted while pretending to be organic. What makes it harder is that these posts often get normal engagement, so it’s not easy to tell whether something is genuine discussion, stealth marketing, or just low-trust content engineered to blend in. Browser extension that flags signals of inauthenticity on Reddit things like suspicious promo patterns, repetitive recommendation behavior, AI-assisted wording, and other trust signals. Would something like that actually be useful, or would it just create noise? More importantly, what would it need to get right for you to trust it? submitted by /u/Outrageous_Guess_962 [link] [comments]

  • 150+ customer messages and admin tasks handled by AI - the owner didn’t touch a thing
    by /u/amberjletang on March 8, 2026 at 5:11 pm

    150+ customer messages, admin tasks, and content updates handled automatically - all without the owner lifting a finger. One small business owner was losing hours every day to repetitive work, barely noticing the time drain. I built a custom AI workflow that learned their exact tone, process, and preferences in just a few days. By the end of the week, it was replying to messages, handling admin, and updating content exactly how they wanted. The owner reclaimed 10+ hours per week - time they didn’t even realize they were wasting. If you could magically hand over the task silently draining your week to AI, what would it be? submitted by /u/amberjletang [link] [comments]

  • The "Signal vs. Noise" problem: How do you actually quantify what news is worth your time?
    by /u/PosterioXYZ on March 8, 2026 at 5:00 pm

    I’ve been kinda obsessed lately with the idea that "staying informed" is actually a trap for most (at least for me, and extrapolating that in the hopes others feel the same). I spend 60+ minutes a morning scrolling Reuters, Bloomberg, Times or whatever else I can come up with, but if honest, 90% of that info has zero impact on my actual business decisions or make me feel more informed (this fluffy concept) I’ve been working on a framework to "score" news stories to see if they actually matter before I read them. I landed on six specific metrics, and I’m curious if other entrepreneurs think these are the right ones, or if I’m missing something: Capital Implications: Does this move markets or affect the cost of doing business? Durability: Will this story still matter in 6 months, or is it just a 24-hour cycle? Decision Utility: Can an owner actually do something with this info? Global Impact: Is this a localized event or a systemic shift? Career/Industry Relevance: Does it change the landscape for professional growth? Clarity: Is the information actionable or just speculative fluff? I’ve been using this to filter my own intake, but I’m curious, and seeking some feedback, how do you guys filter the noise? Do you have a set criteria for a headline before you click it, or do you just rely on specific trusted sources? Which sources do you find reliable? I'd love to hear how others handle information overload without missing events that actually matter. submitted by /u/PosterioXYZ [link] [comments]

  • How we turned brand guidelines into an actual competitive advantage
    by /u/SimonBuildsStuff on March 8, 2026 at 4:37 pm

    Most brand guidelines are aspirational documents that live in a shared drive and get ignored. Ours are a live system that every piece of content runs through. Took us 6 months to build. Started by auditing our 200 best-performing assets and extracting patterns. Not what we wanted to be. What actually worked. Then encoded those patterns into rules that can be checked programmatically. Voice markers, visual constraints, structural patterns. Any AI tool we use feeds into this system. Any asset gets scored against it. Our team can move fast without senior review on every piece because the system catches drift automatically. We've hired three junior marketers this year who are producing quality work within weeks. Onboarding used to take months. That stability itself was worth the pain of getting here. submitted by /u/SimonBuildsStuff [link] [comments]

  • Do you know someone that is insanely good with marketing?
    by /u/avtges on March 8, 2026 at 4:07 pm

    Basically looking for that one person who just gets marketing/brand strategy. The kind people rave about. **Not an agency**, an actual human who’s really good at this stuff. Don’t want to dox them, would genuinely appreciate it!! A little bit about my company: we’re a service in the menswear space and growing fine organically, but I want to understand my options to start marketing across multiple channels. submitted by /u/avtges [link] [comments]

  • we edited 200+ reels last month with a team of 8, but we’re still around $4k/month. looking for some advice.
    by /u/meNiraj on March 8, 2026 at 7:47 am

    I want to be a bit raw here and ask for some honest advice from people who have been in this position. we run a small video editing agency with a team of 8 editors. last month alone we edited 200+ reels along with some long-form videos, podcasts, and thumbnails. the volume is there, but revenue wise we are still stuck around $4k per month. we haven’t been able to cross the $5k mark yet. I know the industry is quite saturated right now, but even with this kind of volume the numbers don’t move much. another issue is how our workflow looks. we mostly do batch editing. so when work comes in, there’s a lot of work at once. but when it slows down, I struggle to keep the editors occupied. there’s still a lot of unused capacity in the team. most of our projects come through whitelabel work for other agencies, which i think is also why the margins stay low. the work is consistent and we’re grateful for it, but it feels like we’re stuck in the middle of the supply chain. so I’m trying to figure out the direction we should take next. I genuinely need some marketing suggestions. what moves helped you grow past this stage if you run an agency or a service business? one interesting thing is that we recently grew a social media account that gets around 1M+ reach, but the audience there is mostly video editors, not people who actually need editing services. almost every long-term client we’ve had so far came through word of mouth and referrals, not through our content. so I'd really appreciate any advice from people who have gone through something similar. would love to hear your thoughts. submitted by /u/meNiraj [link] [comments]

  • Build vs Buy: Every small business had the same problem
    by /u/for3v3rLearning on March 8, 2026 at 6:20 am

    If your business could grow without you driving every lead, sale, and strategy decision, would it? If your business is comfortably above $1M ARR with a leadership team in place, this probably doesn't apply to you. I've spent 5 years evaluating small businesses for acquisition. Marketing agencies, franchises, software companies, woodworking shops, auto body shops, barbershops, fitness studios, tutoring businesses, and more. All within 3 to 12 years of operation, revenue between $200K and $1M. I haven't pulled the trigger yet. My buy-box is precise, and I won't rush. But something kept coming up across every single one of these businesses that had nothing to do with the financials, and it's making me wonder if I should build instead of buy. The pattern was almost identical across industries. The team handled execution, account management, and client relationships. The owner handled leads, sales, marketing, and strategy, everything that actually grows the business. At the lower end, it was usually one owner and a handful of contractors. For over $500K, you'd typically see the owner plus a part-time project manager, an account manager, and contractors handling the work. Nobody was doing the growth job except the owner. And most of them knew it. Here's what that structure creates over time. You can see problems coming, but can't act early enough. It's not that you get caught off guard. You often see the warning signs: a souring client relationship, a process breaking down, a competitor moving in. But you're so tied up in running the business that by the time you can address it, the problem has already grown. The business keeps pulling you back into operations. You want to work on the business, not just in it. But the day has other plans. Strategy keeps getting pushed to evenings and weekends, if it happens at all. You've quietly decided not to scale. This one surprised me the most. Some owners weren't stuck; they had made a deliberate choice to stay small. Not because they couldn't grow, but because growth meant giving even more of themselves to a business already consuming too much of their time. They were protecting their sanity, not avoiding success. The isolation doesn't show up in the financials, but it does here. Owners didn't bring this up in our conversations directly. Understandably, nobody wants to signal vulnerability to a potential buyer. But I see it constantly in Reddit threads by entrepreneurs. A bad week feels catastrophic. A hard decision feels impossible. A setback feels personal. Without someone who truly gets it, everything is heavier than it needs to be. So here's my honest fork in the road. I can keep looking for the right business to buy. Or I can build something that addresses what I kept seeing, a thinking partner for owners navigating exactly this, so they can see problems earlier, stay strategic more often, and not have to carry it all alone. Before I decide, I want to know if I'm seeing this clearly. If you're a business owner at this stage, does this reflect your reality? What's missing from this picture? What would you push back on? And honestly, is the isolation piece real for you, or am I reading too much into Reddit threads? I'd rather know I'm wrong now than build the wrong thing or buy the wrong business. submitted by /u/for3v3rLearning [link] [comments]

  • 1 Year Into My Business and My Brain Keeps Saying “Quit”
    by /u/Potential-Border-223 on March 8, 2026 at 1:30 am

    How do you handle the moments when you feel like you’re not cut out for this? Hey everyone, first time posting here. I just crossed my first full year in business. I launched a startup subcontracting commercial glass & glazing. It’s been a rollercoaster. I’ve had ups, downs, and a lot of expensive lessons: Losing money from bad project managers, mistakes on my end because I didn’t understand the office side, employees quitting, having to lay people off & the constant pressure of figuring things out alone. I’m not here looking for sympathy. I’m here because right now I’m getting my ass handed to me again. The pressure and stress feel insane, and there’s a part of me that wants to run away even though I know that solves nothing. My mind keeps going to that dark place of: **“Who am I kidding? I’m not built for this. I should’ve stayed at my old job.”** For the business owners and entrepreneurs here: **How do you handle the moments when the weight of everything feels like it’s crushing you?** How do you keep going when your brain is telling you you’re not made for this? I don’t have many other entrepreneurs in my field to talk to. When I reach out to more seasoned people, most don’t want to give advice or aren’t available. So I’m asking here: **How do you personally deal with the fear, the doubt, and the pressure when everything hits at once?** Appreciate any real advice. submitted by /u/Potential-Border-223 [link] [comments]

  • Net worth is so messed up
    by /u/CurveAdvanced on March 7, 2026 at 10:09 pm

    I just find it puzzling that a company like Mercor has a higher valuation than Snapchat, and that the founders have the same net worth as the founder of Instagram. Crazy how the world works. submitted by /u/CurveAdvanced [link] [comments]

  • Which Social Networks Convert Best for Early Paid Users?
    by /u/Patient-Airline-8150 on March 7, 2026 at 6:27 pm

    I'm launching a block of paid web apps and trying to figure out which social networks actually convert into the paying users, not just traffic or signups. Especially interested in real experiences from founders/indies who used social platforms to get their first customers. Questions I’d love insight on: Which social network brought your first paying users? Which platforms gave you traffic but no conversions? Did organic posts work, or did you need paid ads? How long did it take to get the first sale from social media? If you started again, which one platform would you focus on first? For context, I'm considering platforms like Reddit, X, LinkedIn, TikTok, and YouTube. Curious to hear what actually worked in practice rather than theory. submitted by /u/Patient-Airline-8150 [link] [comments]

  • What are the best marketing tools that work for you?
    by /u/builtforoutput on March 7, 2026 at 5:20 pm

    What are the best marketing tools that work for you nowadays? For me, organic short form, and paid ads seem to do the trick. However this is a very nuanced conversation, for me short form content works when you tell a story and resonate with the user. Would be interested in hearing other people’s opinions on this. submitted by /u/builtforoutput [link] [comments]

  • The real AI gold rush isn’t in building. It’s in babysitting.
    by /u/wasayybuildz on March 7, 2026 at 5:15 pm

    Times have changed quickly... I was reading about a developer on Reddit shut down his funded startup last week because Claude can now build what he was selling. That should terrify every SaaS founder. But it reveals something most people are missing. The value has moved. Building an AI tool takes hours now, not months. Anyone with Claude Code or Cursor can spin up a working prototype over a weekend. The barrier to entry is basically zero. So where did the value go? It went to the person who keeps it running. Think about it. You build an AI agent that monitors your inbox, drafts replies, and flags urgent messages. Cool. Takes maybe 2 hours to set up. Now who handles it when Gmail changes their API? When the model hallucinates a response to your biggest client? When the agent misses something because your workflow changed and nobody updated the prompt? That is where the money is. Not in the build. In the babysitting. Every AI agent needs someone watching it. Updating prompts when context shifts. Swapping models when a cheaper or better one drops. Debugging the weird edge cases that only show up at 3 AM on a Tuesday. This is why I stopped selling AI agent setups as one-time projects. The setup is the easy part. $5K, done in a week. But then what? The client calls you a month later because the agent stopped working. Or worse, it kept working but started doing something wrong and nobody noticed. Now I sell the ongoing management for niches with boring workflows. I run the agents. I monitor them. I fix them when they break. I improve them when new capabilities drop. The client gets outcomes. Not a tool they have to learn. Not a dashboard they will never check. Just results. This is the real AI ops business. Not "I will build you an agent." That is a race to the bottom. Claude gets better every week and the build gets cheaper every month. Instead: "I will run your AI operations so you never have to think about it." Managed services always win. In cloud computing it was AWS. In marketing it was agencies. In AI agents, it will be the people who handle the messy, boring, ongoing work of keeping autonomous systems reliable. The builders will compete on price. The operators will compete on trust. I know which side I want to be on. submitted by /u/wasayybuildz [link] [comments]

What are the pros and cons of working as a software engineer for Google or Microsoft versus starting your own startup like Zoom or Uber or Airbnb did when they started out?

Google or Microsoft vs startup
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AI Jobs and Career

I wanted to share an exciting opportunity for those of you looking to advance your careers in the AI space. You know how rapidly the landscape is evolving, and finding the right fit can be a challenge. That's why I'm excited about Mercor – they're a platform specifically designed to connect top-tier AI talent with leading companies. Whether you're a data scientist, machine learning engineer, or something else entirely, Mercor can help you find your next big role. If you're ready to take the next step in your AI career, check them out through my referral link: https://work.mercor.com/?referralCode=82d5f4e3-e1a3-4064-963f-c197bb2c8db1. It's a fantastic resource, and I encourage you to explore the opportunities they have available.

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What are the pros and cons of working as a software engineer for Google or Microsoft versus starting your own startup like Zoom or Uber or Airbnb did when they started out?

Google and Microsoft are both giant tech companies that offer great benefits and salaries to their employees. However, they also have strict work schedules and can be inflexible when it comes to new ideas. In contrast, startups are often much more flexible and allow employees to have a greater sense of ownership over their work. They also typically offer lower salaries and fewer benefits, but the trade-off is that you have the opportunity to be more creative and innovative. If you’re the type of person who likes to take risks and be rewarded for your creativity, then starting your own startup may be a better option for you than working for a large corporation.

What are the pros and cons of working as a software engineer for Google or Microsoft versus starting your own startup like Zoom or Uber or Airbnb did when they started out?
Google Search Engine Tech Stack

Google, Microsoft, and Apple are all giant tech companies that started out as small startups. Google and Microsoft both began in the garage of their founders, while Apple was started in a basement. All three companies are now worth billions of dollars. But which is the better option for a software engineer: working for one of these huge companies, or starting your own startup?

There are pros and cons to both choices. Working for a big company like Google or Microsoft comes with a lot of perks. These companies can offer competitive salaries, great benefits, and the chance to work on cutting-edge projects. However, they can also be inflexible and bureaucratic. Startups, on the other hand, are much more nimble and offer the opportunity to be more creative. But they also come with more risks, as most startups fail within the first few years.

Google/Microsoft

Pros:

  • Top-of-the-market salaries.
  • Equity that is definitely going to be worth something once it vests.
  • Insane perks.
  • No risk. You have a very comfortable job that you can stay in for as long as you want.
  • You get all the tools and help you need.
  • You’re in a large community of like-minded engineers.
  • Having a well-known brand on your CV opens up many career opportunities.

Cons:

  • The work can be a bit mundane.
  • There is bureaucracy and petty office politics.
  • You have to answer to managers.
  • You won’t have a huge impact on the company.
  • It won’t make you rich. Just upper middle class.
  • Large tech companies often have questionable ethics.

Startup

Pros:

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  • You don’t have to answer to anyone (except your customers).
  • It’s a very informal atmosphere.
  • It’s exciting. You never know what’s going to happen to the company in the next few months.
  • You have a huge impact on the success of the company.
  • You pick up many new skills quickly.
  • Building something from scratch is very rewarding.
  • If the company succeeds, you will become filthy rich.

Cons:

  • Lower salary.
  • The company will most likely fail and your equity will be worthless.
  • You’ll experience constant setbacks until you reach product-market fit.
  • Your office perks are most likely limited to a coffee machine.
  • You have to do everything yourself, including tasks that you hate.
  • You’ll probably work longer hours.

To conclude:

Ultimately, it depends on what you want out of your career. If you want stability and the chance to work on some of the most innovative projects in the world, then working for a big tech company is the way to go. But if you’re willing to take on more risk in exchange for the chance to create something truly new and revolutionary, then starting your own startup may be the right path for you.

Some people tried everything from tiny startups to mid-sized companies to large behemoths. Based on experience, They’ve found that They very much enjoy working in startups, creating something new. But They’ve also been lucky to meet founders that value their skillset. It is always good to want to start your own company at some point, but the timing and idea has to be right.

Source: Here

AI Jobs and Career

And before we wrap up today's AI news, I wanted to share an exciting opportunity for those of you looking to advance your careers in the AI space. You know how rapidly the landscape is evolving, and finding the right fit can be a challenge. That's why I'm excited about Mercor – they're a platform specifically designed to connect top-tier AI talent with leading companies. Whether you're a data scientist, machine learning engineer, or something else entirely, Mercor can help you find your next big role. If you're ready to take the next step in your AI career, check them out through my referral link: https://work.mercor.com/?referralCode=82d5f4e3-e1a3-4064-963f-c197bb2c8db1. It's a fantastic resource, and I encourage you to explore the opportunities they have available.

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