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

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.

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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  My Thoughts：How to Distinguish Truth from Falsehood in Business?
  by /u/MASTERV10 on January 18, 2026 at 9:04 pm

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  How do i chose a business?
  by /u/Afraid_Scale1986 on January 18, 2026 at 7:51 pm

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  Need strong advice on this
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  How do you effectively sell a startup website?
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  Tips on Tracking Your Numbers from a SaaS/Agency Owner
  by /u/cybersec-sales-dude on January 18, 2026 at 6:23 pm

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  Side hustle success - Luxury Watches
  by /u/allbl4ackeverything on January 18, 2026 at 5:45 pm

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  21 year old college student wants to start a business
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  by /u/AILaunchpad on January 18, 2026 at 5:13 pm

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  What would you do? Help Genuinely needed.
  by /u/Provendio on January 18, 2026 at 5:12 pm

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  The biggest mistake I made when building an AI career related product
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  I assumed the problem was lack of information. It turned out the real problem was lack of confidence in decisions. People already know what skills are in demand. They already know they should improve their profile. What they struggle with is choosing where to focus and trusting that choice. Once I realized this, a lot of my early features felt wrong. Sharing this in case it helps someone else avoid building solutions for the wrong layer of the problem. submitted by /u/aqatei [link] [comments]

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  What are some unspoken hardships of entrepreneurship?
  by /u/Lady_Diana01 on January 18, 2026 at 4:26 pm

  Hi everyone! Just want to know. What are some of your unspoken hardships? Hardships that nobody talks about but you would want to read about written by a fellow founder/entrepreneur? submitted by /u/Lady_Diana01 [link] [comments]

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  Entrepreneurship especially the innovative Entrepreneurship is a privilege
  by /u/PlsStarlinkIneedwifi on January 18, 2026 at 4:23 pm

  After failing so many startups(or even if you can call that) around 10 now or more my stubborn ass finally realized innovative entrepreneurship may not be the right entrepreneurship for me currently. When I started entrepreneurship at 17(19 now) I wanted to make something new that solved a problem and there was no other solutions like mine. Hence, my scope got really small to make something new and realistic it had to be a: digital product, non-expensive infra, and relatively easy to make as a solo dev. So as you can see all my failed startups were digital products mostly apps and websites that solved some kind of problem. However, I didn't really take into account that making something innovative would most likely need a lot of funds that not a single inexperienced individual can make, so each grand idea would ultimately scoped down to nothing that was slightly worse than potential competitors. I honestly learned that anything innovative requires many things such as certain skills, knowledge, and especially funds to actually deliver. Note: I haven't spent more than 500 dollars on all 10 startups as it was digital products most come from apple development program costs as well as small tools to help accelerate building . submitted by /u/PlsStarlinkIneedwifi [link] [comments]

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  Anyone have experience dealing with a slow responding, longer than expected lead time manufacturer?
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  Business owners: how did you build your 2026 plan and financial targets?
  by /u/DelightHornet on January 18, 2026 at 3:11 pm

  Hi everyone, I’m sitting down to map out my strategy for the rest of 2026, and I’m realizing I don’t have my core vision or financial projections fully locked in yet. I run a business in the home services / flooring space, and I want to do this the right way rather than just guessing revenue targets based on last year’s numbers. For those of you who already have a solid roadmap for this year: How did you determine your numbers? Did you simply add a percentage to last year’s revenue, or did you use a more structured formula or model? What tool or system helped you build the plan? LivePlan, a specific Excel/Google Sheets template, Strategyzer, EOS, or just a whiteboard and iteration? I’m looking for a system or framework that helps me pull the vision out of my head and translate it into actual, trackable KPIs. Thanks in advance really appreciate any insight. submitted by /u/DelightHornet [link] [comments]

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  Consolidated 7 daily writing sessions into one 30-min weekly batch
  by /u/aperez13 on January 18, 2026 at 2:59 pm

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  Is it a bad idea to start multiple businesses at once?
  by /u/SubstantialCount3226 on January 18, 2026 at 2:51 pm

  My job laid off a thousand+ people including me. I have my salary until summer without any job to do, and I want to invest that free time into trying to get a business up and running. The problem is that I can't decide on what to do... My three ideas are: 1) A service business in an "unsexy" field where the customers are the government and other businesses. The issue with this though is that it's not really the field I've been in, so I lack contacts, and I would need to do build up a "portfolio" of a lot of free work to be able to win those government contract over the competition. 2) An e-commerce for a product that has a ~6% return rate, good margins, but pretty high competition and it's a "luxury" (non essential) item that cost around ~$75. My issue though, is that I have no experience of making good content for social media (and while I've started learning, I lack confidence). 3) A digital platform where the users come from a specific industry, where the only current platform truly sucks. It has the potential to grow to a much larger customer base and also internationally. So major potential, but, I'm not a good programmer! And I lack experience in hiring and operating a team... I also only have $60 000 that I'm willing to bet on getting a business up and running. And I'd rather not deal with spending a bunch of time trying to find investors until I've verified that the business is a good idea. So my issues are limited funds and time, lack of knowledge and the fact that I can't decide on which one will give me best returns... Is it a bad idea to try and do all if it at the same time? submitted by /u/SubstantialCount3226 [link] [comments]

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  How did you get your 1st client as an analytics consultancy?
  by /u/Elefant7805 on January 18, 2026 at 2:09 pm

  Online, meetup, community... what channel and what approach got you 1st client? submitted by /u/Elefant7805 [link] [comments]

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  One thing I keep noticing about early-stage founders
  by /u/CleanOpsGuide on January 18, 2026 at 1:40 pm

  One thing that surprised me early on wasn’t how hard execution was, but how much mental energy went into deciding what even deserved attention. At the beginning, everything felt important. Pricing, messaging, tools, systems, getting customers, it all competed for focus. Because of that, progress felt slow even when I was “busy.” What shifted things wasn’t learning more tactics. It was changing the question I was asking. Instead of trying to make the right decision, I started asking what I would still learn even if I got it wrong. Once the goal became learning instead of optimizing, momentum showed up in unexpected ways. Decisions got smaller. The pressure dropped. Progress felt lighter, even when outcomes were uncertain. I’m curious if others experienced a similar shift. Was there a moment when things got simpler, not because you had better answers, but because you stopped trying to get it right? submitted by /u/CleanOpsGuide [link] [comments]

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  Tampa Contractor/ slow market + increased material costs
  by /u/JKPRW0221 on January 18, 2026 at 1:34 pm

  Hey everyone, looking for honest opinions from other business owners. I run a small aluminum contracting business out of Tampa, FL (pool enclosures, screen rooms, patios, etc.) and the last six months have been rough. Work is way slower, and material costs are up about 37% this year. A lot of companies around here have laid guys off, and I had to do the same just to stay afloat. At this point I’m trying to figure out the smartest move forward. If you were in my position, would you: Raise prices even if it costs you jobs? Focus only on higher margin work and stop taking smaller jobs? Lean into repairs/rescreens to keep cash moving? Spend more on marketing even though money feels tighter? Cut everything possible and just ride it out? I’m not asking for pity, just trying to make the right decisions and not get buried. Would appreciate any real advice from people who’ve been through a market like this. submitted by /u/JKPRW0221 [link] [comments]