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…

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.

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

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    To ensure we're building something truly valuable, we're looking to connect with sports fans and people who have participated in sports betting (or want to). If you’re willing to sharing your thoughts and experiences, I’d love to have a quick 10-minute call with you. Your feedback will help shape the future of our product, and I promise to keep it brief and straightforward! If you’re up for it, please drop a comment or DM me, and we can coordinate a time that works best for you. Thanks in advance for considering it – your insights would be incredibly valuable! submitted by /u/Smokey_Stache [link] [comments]

  • Starting a leather goods business?
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    Hello all, I’ve been kicking around the idea of starting a small leather goods business. I just really love solid quality leather products like belts, wallets, journal covers, the usual. I recognize those things aren’t hard to find and the market for that is probably pretty saturated. Does anyone have experience with that market? Even for just a side hustle, I’m curious how viable something like that would be and what the realistic buy in would involve. Open to any thoughts or suggestions that will be helpful as I research. Thanks! submitted by /u/schwack-em [link] [comments]

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    Hello all, I’ve been kicking around the idea of starting a small leather goods business. I just really love solid quality leather products like belts, wallets, journal covers, the usual. I recognize those things aren’t hard to find and the market for that is probably pretty saturated. Does anyone have experience with that market? Even for just a side hustle, I’m curious how viable something like that would be and what the realistic buy in would involve. Open to any thoughts or suggestions that will be helpful as I research. Thanks! submitted by /u/schwack-em [link] [comments]

  • I have no ideas for building!
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  • Rejected from every SWE job to raising $500k to build the anti-Google. Here's my story.
    by /u/notepad--- on September 14, 2024 at 4:02 pm

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  • Advice needed : Transitioning our family run ladies handbags business to build a brand and engage with end consumers
    by /u/hsms117 on September 14, 2024 at 1:38 pm

    Hey Reddit, I'm part of a family-run Ladies Fashion Handbags business that has been in the industry for almost 30 years, primarily operating on a B2B model across the GCC. We source our products from China and distribute them in the UAE. As the third generation in the business, I see that we need a serious shift in how we market ourselves. We’ve noticed a few trends in the market over the past years: Premium Competitors: There are brands out there selling similar handbags to ours, but at significantly higher prices. What’s frustrating is that despite us offering similar quality at a lower price, customers still gravitate toward these premium brands. Low-End Competitors: On the flip side, some brands sell lower-quality handbags at dirt-cheap prices. Unfortunately, many retailers prefer these cheap options despite the clear quality defects. The Gap: So, my idea is to position ourselves in between. We provide high-quality handbags at competitive prices, and I believe there’s an opportunity to carve out a niche by developing our own brand. The Goal: I want to start targeting end consumers directly so that they become aware of our brand and begin asking retailers (our customers) to stock our bags in their stores. Here’s what I’m working on so far: Website Development & SEO: I’ve started building our website with a focus on B2B clients and improving our SEO to capture more leads. Content Creation for B2C: My plan is to create content to engage the end consumers without selling directly to them. I believe that brand awareness is key here, and by generating consumer interest, we can influence retailers indirectly. ERP System Development: We’re also developing an ERP system tailored to our specific business needs to streamline operations and better manage our growing demand. Company Culture Shift: One of the biggest challenges we face is that our company has historically been reactive instead of proactive. I believe it's crucial to move forward by doing—taking action, facing challenges as they come, and iterating quickly, rather than trying to plan for every possible scenario. This mindset shift is essential if we want to stay competitive, as sitting on ideas while competitors continue to gain market share feels like a lost opportunity. The Dilemma: Now, here's where I’m unsure. Should I invest time in making a detailed plan for everything upfront—covering all contingencies—or should I take a more agile approach, tackling challenges as they come and adjusting along the way? What has worked better for those who’ve been through similar situations? TL;DR: We’re a family-run Ladies Fashion Handbags wholesaler targeting a B2B model. I want to build our brand to engage end consumers while maintaining our B2B focus. I’ve started with website development, SEO, and content creation, but there’s still a lot of work ahead. We’re also developing an ERP system and trying to shift from a reactive company culture to a more proactive one. Should I sit and plan everything out or take things as they come? Looking for advice! submitted by /u/hsms117 [link] [comments]

  • What are the biggest personal problems you are facing as a young entrepreneur?
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    Entrepreneurship is very glorified. Working for yourself, having a flexible work schedule, fast cars, ... Well the reality is a little bit different :/ Here are some things I struggle with the most and have also seen other young people/friends struggle with on their road to greatness: loneliness (doing your work in silence, no one to talk to, no one to tell you you're doing a good job, no one to hold you accountable, ...) procrastination (sometimes it's very hard to do what you know you have to do, even standing up from the bed sometimes feels like a struggle) no emotional support (friends don't really know what you are doing and are trying to achieve, parents aren't happy because you're not working at some random company, ...) lack of discipline (I admit that some days I sit in front of the computer for like 14 hours but only get like 5 hours of work and the rest of the time I spend on my phone or some s**t) These are just some of the common personal struggles I have faced in the past and some that I still do on a daily basis. I'd love to hear your opinion and also feel free to share your own struggles 🙂 Cheers submitted by /u/Luka1607 [link] [comments]

  • What's your worst experience with a customer?
    by /u/GoodTimesDaily on September 14, 2024 at 11:39 am

    They say, "The customer is always right (in matters of taste)," but in other areas, let's be real—sometimes they’re really, really not. What’s that one customer story that still makes you cringe or laugh in disbelief? submitted by /u/GoodTimesDaily [link] [comments]

  • Ways I plan to run my 2nd business differently than my 1st
    by /u/datawazo on September 14, 2024 at 11:37 am

    I've run a consultancy for 7 years. Two employees + me, both recent ish (last 2 years). This week I plan on launching business #2. I'm going to a networking event where I won't know many people and will try pitching this new endeavour instead of the current one. Here's everything I hope to change this time around. For context my current business is data analytics consulting and my new business is in the same space, but niched a bit more into a specific horizontal, doing setup and analytics into a specific function that would be done by ~80% of businesses. Client Acquisition... When I started in 2017 I was working FT, didn't know what I was doing, and got most of my first clients from freelance sites. Which was fine - I commanded a good price, paid a commission but still made good money. The hard part is growth. On these sites you pitch yourself, not your business, so I've been the front man for these companies the whole time. Very difficult to get my employees in front of them as they think they've hired Ray, not DataWazo. New business I will be going after it via linkedin and targeted cold emails, as well as in person networking. I already to Linkedin, but the other two will be a bit newer to me. Have a communicable value prop A lot of this comes down to niching, but with Data Analytics consulting it's much harder to voice the benefits. It's like ya you'll have clarity, probably. You'll be able to see the numbers better. But it's a bit fuzzy. New Business will have clear deliverables to help with selling, clear KPIs and benefits that can be "elevator pitched". Will try this out on Tuesday at the conference, excited to see how it goes. Similarly, measurable ROI. I've been fortunate that few of my existing clients have asked me to prove my worth, but it's hard to do as a generalist. Some had clear time savings achieved in their processes but some really just got nice dashboards for decision making and beyond that hard to say what they did. ROI is good for two reasons - 1 is it proves your worth but 2 it facilitates case studies. Hard to say look at this case study on these dashboards I built they're so neat. Not a riveting pitch. With better ROI you can have "We helped company XYZ get metric B up 10% with blah blah blah" much better for the website, socials, investors. Make things scalable. As I got really busy two years ago I thought hey I'll add an employee. And then I added another. And you know what, I'm still really fucking busy. REALLY busy. It hasn't helped, worse I'm the bottle neck for them. It's for a variety of reasons, but one is a lack of consistent processes in the current business. Everything is a new project, nothing is consistent. Zoning in on an Horizontal will (hopefully) allow for scale, and the ability to add people along the way as processes mature. My goal (my wife's goal tbh) is work less than 60hours a week by my 35th birthday - 13 months away. Outsource more, earlier This one isn't fair to my former self, since I didn't have a good bank account when I started DataWazo. It took me a year and a half to hire a bookkeeper as I got on my feet, and I didn't hire anyone else for a while longer. But DataWazo will continue and is making good money still, so I'm hoping to be able to pull some of that in early to kickstart new company. I shouldn't need to be the one doing all the marketing, all the socials, the comms. Heck I won't be able to, not with the old company still being operational. Outsourcing a lot at the start will hopefully also help develop the processes needed for scale, without me. All in all - I'm finally feeling the effects of building business one in a way that scales very poorly. Maybe it's hiring too late, maybe it's positioning myself too much as the anchor man rather than the company, maybe it's a complete lack of processes. Probably all. But I'm hoping I can change that with this new venture. Really rethink how we're delivering as a company and build it so I can be at least a bit more handsoff. Anyway. Thanks for coming to my Reddit post. This was a lot, but mostly to get it off my thoughts in order, and my twitter followers don't really care about it. submitted by /u/datawazo [link] [comments]

  • Question about Start-up finders fee
    by /u/BlueEdenProject on September 14, 2024 at 10:25 am

    I have just received a recommendation to funding my project. The agency would like to charge the investor 30% higher than what I need. The investor will pay to my account with the full amount, then I'll pay the 30% fee to the agency. They would like to keep the secrets between us, and want the finders fee paid in crypto. This thing looks weird. Can somebody advise what could be wrong? Is it a fraud? Thanks a lot! submitted by /u/BlueEdenProject [link] [comments]

  • Education for aspiring entrepreneurs
    by /u/icamejustbywatching on September 14, 2024 at 8:52 am

    When watching YouTube videos I hear a lot of guys (like Alex Hormozi) saying you should invest in yourself and your education to improve and hone your entrepreneurial skills, as opposed to investing in stuff like stocks/crypto/whatever as you generally don’t have a lot of wealth at the start of your journey. My question is, what stuff should I invest in to improve entrepreneurial skills? Do they mean online courses or something completely different? I’ve got some cash saved up, but I’m not sure what the best way is to invest it in myself and my education, in order to set myself up for future success. Any tips/help would be very much appreciated! submitted by /u/icamejustbywatching [link] [comments]

  • How do I deal with increasing number of staff?
    by /u/Financial_Roof_4762 on September 14, 2024 at 8:17 am

    I run a small road construction company that currently handles simple asphalt laying, along with everything related to that process. My main customer is the local municipality. Larger road construction companies typically take on bigger projects, such as building new roads from scratch, which involves underground work like laying cables, pipes, and installing pillars. To grow my company, I’ll eventually need to take on these kinds of projects, but that would require hiring engineers and additional specialized staff. As of now, the company is divided into three departments: operators and mechanics working at the asphalt plant, workers and drivers on the road, and office work, which is entirely handled by me, including documents, invoices, project coordination, and many more. As the owner, I have to manage all three departments while also maintaining supplies, meeting new clients, and keeping track of everything. So far, I’ve managed to handle it, but there’s a major issue: about 95% of my staff (currently around 15 employees) are unproductive unless I’m directly supervising them. If I’m at the asphalt plant, the road workers tend to slack off and do very little, even if I’ve given them specific tasks. They often make excuses like a machine broke down and needed fixing instead of completing the work. The same happens when I’m on the road — the plant workers don’t get much done either. Next year, with more projects coming in, I’ll need to hire around 10 additional employees to keep up and grow the company. But the bigger issue is that I’m in Bulgaria, where unfortunately, most workers tend to be lazy and untrustworthy. Hiring supervisors or managers is difficult because they’re likely to steal or lie. Increasing salaries isn’t an option since everyone is already paid above the market average. I’m really anxious about how I’ll handle more projects without wearing myself out by trying to be in three places at once, while still maintaining quality and standards. How do you manage multiple departments and improve productivity when it feels like it’s close to zero? Is there any technology or system I could implement to help? I would really appreciate any advice. submitted by /u/Financial_Roof_4762 [link] [comments]

  • Where did you find success in getting customers?
    by /u/apsiipilade on September 14, 2024 at 7:44 am

    Fellow founders, I run an early stage b2b startup but I have been struggling to find new customers. What are some marketing channels that has worked for you? Thanks in advance submitted by /u/apsiipilade [link] [comments]

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