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.


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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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  • What’s your Product, Service, Offering, Goal, or Reason to be here?
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  • PLEASE READ: This story blew my mind
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  • $8 short for $1000 MRR - Here's what worked for my SaaS
    by /u/TasAdams on May 9, 2024 at 12:26 pm

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  • I will be in a place where there will be a lot of tourists, give advice on how this can be monetized
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    . submitted by /u/berlin_633 [link] [comments]

  • 17M , looking for some work
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    I hope this is not taken down . I am a 17 year old teen , my summer vacation starts in a week . I will have around 14+ hours a day . I can say im pretty fluent in english , a fast learner and have previously made money online through commission based outreach . If you have any repititive online tasks, I can do them for you . I have experience in text based outreach but willing to learn too . Would prefer anything that pays task / per hr based submitted by /u/generativex [link] [comments]

  • This shit is tough lol
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  • Sam Altman has 13 tenets for becoming wildly successful. Here they are.
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  • How do I launch properly?
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  • Thank you Thursday! - May 09, 2024
    by /u/AutoModerator on May 9, 2024 at 9:00 am

    Your opportunity to thank the /r/Entrepreneur community by offering free stuff, contests, discounts, electronic courses, ebooks and the best deals you know of. Please consolidate such offers here! Since this thread can fill up quickly, consider sorting the comments by "new" (instead of "best" or "top") to see the newest posts. submitted by /u/AutoModerator [link] [comments]

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  • How can I promote my app online without spending much?
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  • What is that one Business which helped a Country from going from a Developing country to a Developed Country?
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  • People who make $10k+ Per month working for themselves? What do you do
    by /u/sky-builder on May 9, 2024 at 5:42 am

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  • Need some advice.
    by /u/MisterQuote1997 on May 9, 2024 at 3:44 am

    For some context I’m 26. I’m not married, and I don’t have any kids, although I do want those things. After a battle with cancer I’m returning to the workplace. I currently work a customer service job right now being paid $14 an hour. However my real passion and dream is to have my own financial services firm. I currently hold an active life insurance life and a series 6 investment license. I’m also working on my series 26 principle license and will get my series 63 after that. I’ve worked in the financial services industry on and off for almost a decade now. I started when I was 18, and I know that I can be massively successful at if I just put in the work. I just never fully committed to it because I struggled to believe in myself and it took me a while to build consistency in the right habits. During the time when I was sick, I have worked on my mindset, I become very disciplined and consistent, and I fully believe i can have success in this field. I also have a mentor who is very successful in this industry and can help me. I took this job for security because I know it will take time to build my business from scratch. But there’s a part of me that just wants to go full time in my business even if I may struggle to get momentum in the beginning. Every minute at my job I am thinking of what I could be doing in my business instead. Should I stay at a job I really don’t like for stability or take the risk with my business? What would your advice to me be? I want to be smart and make the best decision I can, but at same time I understand fully how limited my time is and I’d rather not waste it being at a job when I could be doing more. submitted by /u/MisterQuote1997 [link] [comments]

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Exploring the Pros and Cons of Visiting All Provinces and Territories in Canada.
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Exploring the Advantages and Disadvantages of Visiting All 50 States in the USA
Exploring the Advantages and Disadvantages of Visiting All 50 States in the USA


Health Health, a science-based community to discuss health news and the coronavirus (COVID-19) pandemic

Today I Learned (TIL) You learn something new every day; what did you learn today? Submit interesting and specific facts about something that you just found out here.

Reddit Science This community is a place to share and discuss new scientific research. Read about the latest advances in astronomy, biology, medicine, physics, social science, and more. Find and submit new publications and popular science coverage of current research.

Reddit Sports Sports News and Highlights from the NFL, NBA, NHL, MLB, MLS, and leagues around the world.

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