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.

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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


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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.

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  • I failed as an entrepreneur. Being an entrepreneur ruined my life.
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    My whole life its been my dream to start and own a successful business. It wasn’t because I didn’t want to work a 9-5 or because of any external factor. I just fell in love with the being a business owner. It didn’t matter how hard it was, i noticed i always did the work necessary as a business owner nonetheless. For the most part it was harder than a traditional 9-5 but i still did. This how i knew it was something i wanted to do and be. It all started when i first moved to the United States as a young teenage boy from a third world African country. Coming to America inspired me. Seeing the opportunities, I decided to strive for the “American Dream”. Man only if i knew how much of a lie most of the info I’ll come across on this journey was. At first my version of the American dream was work hard, go to school, become a doctor and get a good job earning 6 figures. This what my father has instructed me to do to be successful in this country. So I listened. 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This took me down a rabbit whole of research into what they did etc Realizing i didn’t have to become a doctor to be successful, gave me a breath of fresh air as i was no longer restricted to doing something I didn’t like. So sometime during my 2nd semester of freshman year i decided to do research into how people made it and became successful. Thats when is stumbled upon online business aka ecommerce aka drop shipping, ebay etc. I opened my first ebay account eneded yo seling a few items I owned but i had no clear vision with it, so i did dropshipping. Which this i had to learn alot of things like web design etc. built my first store… pfffft I thought once is in the internet sales will start flooding in. Nope. Store was live and the only store visitors i had were bots. Only for me to realize i had to market. I had limited capital at that time so i decided ill come back to it once I’ve learned what its needed and when i have some more capital on my hand. Back to research. Some people online were preaching about having clients and selling services to people as a marketer, so after learning some social media marketing from a $3000 course online i decided to cold call and email business owners to run and generate leads and sale for them. Pffft tried that for months, that didn’t work out I didn’t essentially like the business model anyways. The only business model that really resonated with me was ecommerce. My second year of college, I decided to use my college refund checks to start a clothing business. Which became my first real business ever. I told my family told my firienfs. To my surprise it wasn’t easy as expected but for some reason i still felt so passionate and inspired regardless of the drawbacks unlike what i ever felt working hard to become a doctor. In my first 2 weeks of starting the business with $700 i sold out on all my inventory giving me a return of $2000. Boy i was so stocked, I started dreaming of the lambo i was going to buy when i sold more. I mean all i have to do is sell more right?! Nope it wasn’t like that. The people online make it sound so simple but it really isn’t. I decided to expand my business and market online but unfortunately, that didn’t pan out after so much spend on online marketing to strangers. I realized that most of my customers i previously had where friends, family and colleagues i knew and it wasn’t really a hit in the real world. Luckily i was able to meet an entrepreneur in my area who had a clothing business doing about $1mill a year at that time. Now he does about $10M annually. This became my first ever real mentor but our conversation was limited although just the connection gave me hope especially seeing someone my color doing it. I went a period not doing my clothing business as it wasn’t moving as expected. I decided to venture into other entrepreneurial opportunities. Thats when my friend introduced me to a lady who had approached him professionally promising a lucrative opportunity as a “network marketer” willing to become our mentor etc. i had to pay $600 to join this group and go for weekly meeting. Sounds like a cult don’t it. But nah overtime i and my friend realized we’ve been hooked into a ponzi scheme. At the time i had no idea and my friend introducing me to it was just me becoming one of his under link that he will make money from when i sell products and recruit people under me. All this he had explained to me ofcos. That i ended up leaving realizing how damaging it could be to my reputation. Now yet another failed venture. I decided to push forward. I was marketed a course that will teach me a skill that will generate me $1000- $10,000 plus a month and all i have to do is pay $3000. Well obviously that was a scam as well as i made not a dime from being i this paid community. At that time getting rich of selling courses was just becoming a thing but so people fell for it. I took my loses and move on. Of course while doing all of these i was still in school trying to become a “doctor”. I read countless books on self development, business as i was told the lesson in books help one to be successful. 4 years down the road and nothing to show for it. “God what am I doing” is this the right path?! Nothing but failed ventures and scams. The bias in this is the people online are the 1% that made it but there are the 99% tried and failed. I was so optimistic i though i could be this 1% not understand how small of a ratio that is. Along the coming years i tried various other things. Stock trading, crypto, social media etc. Made a few bucks from these but nothing significant to call a business or to build off from. Work hard they said, work smart that said, all that i did and nothing. I was engrossed with sad ness and negative self perception , doubt and pity. I mean “i did all they said you should do” “why am i not yet successful?!“ i read the books went for the seminars to initiative and action, was patient and consistent, invested in education… I graduated with a degree in psychology premed. Realising the loans and requirements it will come with to become a doctor after establishing that’s not who i wanted to be, i decide to-end it there. My dad had instructed i go back to school to purse a masters program but i was not motivated in the slightest. My live for having a business was still there. I ended up getting a part time job with the help of a friend based of my degree. Wasn’t earning much but it was something. After a few months i got the energy to start another venture, so i made a deal with my dad. “Give me a year in this venture” “ if i earn up to $100,000, i don’t get to go back to school and if i don’t i’ll do whatever you want me to do” . So i stared on this new venture. It was another online clothing brand but this time i decided to do things different. I sent a message to my mentor at this time he is generating about $2m in sales his was advised at the time was to go back to the drawing board if something isn’t working. We met and talked for an hour or 2. In summary after a year on my clothing store, I generated about $100,000 in sales ironically. Although this was just revenue. Profit was around 20% which was great at that time but i ended up blowing this money and going in depth trying to just reinvest. Its been 6 years since you’ve been on this journey and you have nothing to show for it. Boy did negative self talk eat me alive. I wallowed in depression and had thoughts of suc*ded at this time i was dead broke, with nothing to my name. I prayed, i wished, i cried but nothing. 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  • Starting a $70k/yr agency - lessons on getting the first few clients
    by /u/lilbean1s on May 8, 2024 at 9:45 pm

    Hello! First and foremost, I want to say that I am by no means an expert, I’m just here to share my story and what has worked for me thus far. Hopefully I can provide you guys with some value. So, around a year and a half ago I decided to start freelancing with web development. I was self-taught, and at the time I was a barber. I was fed up with using clunky tools for scheduling/managing my appointments, so I decided to code my own. Around the same time, I started to run ads on google directing traffic to my business, and I had great success with it - between 3-5 new clients per day in the first month. I witnessed firsthand the power that an optimized website and marketing could have on a business, so I figured it would be worth a shot to offer this service to local businesses like mine. After walking into similar businesses and pitching my story, I finally got my first client. By word of mouth and more cold approaches, I slowly got more and more clients that liked my work. A key lesson I learned starting out is obvious, but I wanted to emphasize it here: establish confidence with who you’re talking to. This can be done in so many ways, but in my case, it was twofold: I had results. I quite literally showed them my google ads campaign’s results and the amount of website clicks/bookings/calls I was getting. Being honest and having results is perhaps the most useful thing I did. My offer was unique. Starting out, I wasn’t sure how successful I would be, even if I had my results in front of their faces. So I made them an offer they couldn’t refuse. I chose to go with performance-based pricing, so that if they didn’t get the results we agreed upon, I wouldn’t get paid. This meant I had to back up my talk. Lastly, I decided to incentivize referrals. If my clients landed me a new project, I would give my clients 10% of whatever I ended up charging them. This also was a huge boost I hope you found some of this info useful! In short, solve a problem you have, optimize, and help others do the same. submitted by /u/lilbean1s [link] [comments]

  • Why is everyone a 22 years old millionaire these days ?
    by /u/ecopetroleum on May 8, 2024 at 8:24 pm

    It's becoming hard to get a grasp of what entrepreneurs are actually making. I remember 5 - 10 years ago when making 10k / month online was considered a massive success. Gurus used to talk about how it took them "decades" to get to that level. Nowadays it seems like every youtuber is a 23 years old agency owner making $ 150 000 / month. Google their name, even on reddit, plenty of people can "Attest" that they "are legit and the real deal". Am I missing something ? submitted by /u/ecopetroleum [link] [comments]

  • I launched a trustless ponzi on r/cc 13 days ago and it doesn't show signs of stopping
    by /u/swagamoney on May 8, 2024 at 6:56 pm

    So I soft-launched an Arbitrum app on the crypto sub that lets users host or join trustless ponzi games. You "invest" ETH and earn up to 100% ROI that's being paid by subsequent "investor" deposits. The catch is that your funds are only released when you hit the 1-100% ROI threshold (set by the game host). If the game expires before that - you lose your deposit. What I did differently from similar games in the past is that I made a jackpot function that pools all of these unreleased funds and gives them to the last player to join the game. It incentivizes players to join indefinitely as the jackpot grows exponentially. The catch is that each new deposit resets the 10-hour game timer. And because of that reason this one game is now live ever since launch (over 13 days). It won't me allow to insert an image but it's called "smol profits" on the platform Every time I think it will finally end someone joins and resets the timer. The last player to deposit a min. of 0.003 ETH is looking to cash 0.316 ETH or more than 100x at the moment. Or a 100% return on his deposit if enough people join after him. How do you think this plays out? Can this be a sustainable product? (I'm getting half of the host fees as the platform fee) P.S. the app is called ponzimarket and these are the contracts - https://github.com/swagamoney/ponzi.contracts (app link is there too) submitted by /u/swagamoney [link] [comments]

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