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.

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.

Examining the Fragmented Data on Black Entrepreneurship in North America

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    I don't know how to transition from my current client base who only need once- off projects done to clients who want monthly work done and turn this into a solid business Its so easy to get monthly retainer clients when you're in the IT industry or some other industry but graphic design? I feel stuck with once-off projects. I've met people in my industry who has monthly retainer clients I don't seem to know how to transition into that Any advice please? submitted by /u/ProgramExpress2918 [link] [comments]

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    I have about 125K to invest from a job that ended with a lumpsum parachute. I have always been interested in childcare business as it is a deep interest and hobby for me (teaching) and it is an industry that seems evergreen. There are a few daycares in my area up for sale - starting from 20kids all the way upto 150 kids capacity. The one I am interested in got hit pretty hard during COVID and current owner branched out into other industries. Anyway, I am interested in learning more about the money aspects and specific business valuation for childcare so any resources would be great. Should I hire a business trader expert (like from bizbuysell) or a childcare business group (if there is on that exists), or a CPA would be able to help? Want to make sure I consider all the factors before I even start considering myself as a potential childcare business owner. TIA submitted by /u/zaphodX [link] [comments]

  • Has anyone ever dealt with a YouTuber who sent their viewers to spam bad reviews on your page?
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  • Looking back on my last year's rock bottom moment
    by /u/magheru_san on June 17, 2024 at 5:30 am

    Last year around this time I was in a tough situation. I had just left AWS 8 months before with big dreams to build something on my own around my AutoSpotting AWS cost optimization project. Spent all that time focusing on improving and growing AutoSpotting. The software was better than ever before, (and I kept improving it even more since), but Spot prices temporarily increased close to the on-demand price levels around May last year. Two of my largest customers at the time, most of whom I had for years, suddenly switched to savings plans, which is another way to lower costs. Half of my revenue vanished overnight. I was burning through my savings alarmingly fast, and my unemployment benefits were going to end in a couple of months only to further double my burn rate. One thing I knew was I didn't want to return to a 9/5 job ever again. I thought about what to do next, and decided to switch to services, helping companies reduce their AWS costs. After all I've been doing this for many years and I'm pretty good at it. I soon got a new customer, and was very excited to give them my very best. Besides some low hanging fruits on waste removal and rightsizing, the main thing I suggested and strongly believed would be great for them (resulting in many nice side effects besides cost, in security, observability and IaC), was to consolidate their individual EC2 instances running Docker Compose to a shared ECS Spot cluster. But they had a complex microservice arhitecture and the conversion turned out to be much harder than we expected. We did 80-90% of the work and then suddenly the customer gave up after they saw it took too long and then we decided to instead just put everything on a single instance running Docker compose, getting to roughly the same cost savings but without any of the other benefits. Even though I had spent a month working for them and still helped them a lot to reduce their bill about 100k yearly, from $12k to under $4k, I decided not to charge them anything for my work because I thought I mislead them on a wrong path. It was so painful to give up all that money I so desperately needed, but I still think it was the right thing to do. I try to deliver my customers at least 10x more value than their investment, and if I fail to that I'd rather not get paid for my work instead of making a quick buck off them. Even though I worked for free, I learned a lot from that first services engagement and started to build tooling to automate what I did, which I used and kept evolving in my next engagements. Working with a few more customers since, I gradually improved my services and tooling and started to succeed at getting paid for my work. It's been a year, but now I have a productized services offering with a track record of delivering great results, over a dozen tools that I use to deliver savings better and faster for many AWS services, and a much more reliable way to find new customers. The other week I also started to sell the tools and IaC building blocks I started to build after working for free for that customer a year ago. It's still not perfect and I still struggle occasionally with certain things, but I'm in a much better place than last year, improving every single day and loving every second of it. One thing I know is I'll never give up on my dreams! submitted by /u/magheru_san [link] [comments]

  • What book have you read that has completely transformed your business?
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    Been toying with the idea of a monthly service to help small business owners and executives who want to get better results in their personal productivity. Finding similar offerings currently in the market is vital so I can know where I can specifically add more value So far, the only way I can think of to find competitors is to search Google for people who are running ads addressed to my target audience. Wondering if there are better ways to go about this Please what do you recommend? Would greatly appreciate your help. Thanks! submitted by /u/ceeczar [link] [comments]

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  • Countdown to Launch
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    Case Study Scenario: You’re launching your business, it’s in the healthcare space giving uninsured individuals access to low cost care pathways (cash rate MRI, ultrasound, etc) in 36 states through a very user friendly HIPPA compliant website. You have all the legal agreements, LLC, and even a mentor in place who helped you build the model off of their own business. Your profit model is only a few $ off of each order to stay competitive, so you’re shooting for volume. Go live date is in mid July, and you’ve had some causal conversations on it with people in your target buyer market and gathered interest but nothing formal is in place as the site is still finishing final testing. What is your first step to start a successful launch? You’re not wanting to be Instagram famous, just quietly solving a problem and fulfilling your passion of growing something new. You would however, like some initial clients to beta the site for the first 90 days. Your 30 day goal is 1,000 orders out of the 25.9 million underinsured or uninsured population in said states. Do you make an email list? Invest in paid ads? Set up social media campaigns on the business page? Word of mouth? Mimic GoodRX with their attractive discount cards? Drop your thoughts below! submitted by /u/ViewSouthern7692 [link] [comments]

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    *Crossposted due to lack of interest/response in other subs. I am a small business owner, and specialise in building custom operational software (not pretty websites) for business clients. A few years ago, I was looking for a system that could help me manage the work I was doing on multiple projects and found most existing productivity tools were either too focussed on theoretical concepts and not enough on practical usability, had steep learning curves, or did not have the combination of features I needed. It became clear that I would have to build one for myself, so I cobbled a quick fix for myself in less time that it would have taken me to learn how to use the fancy ones I found that made no sense to me. Over the years, I added more and more features and functionality to it, and it has become an absolutely critical part of my business that I use every single day, and would be completely lost without. Then someone suggested I should make it available to others and maybe put it out there as a SaaS. So I did, and it is now live. I am not after signups from this post, because I am happy to just let it sit there and accumulate users organically over time. What I am interested in though, is getting some honest feedback from those people who are most likely to get some use out of it, about the first impressions it makes when you look at it. Now, I need to make a couple of things clear. First, I am not a website designer, so have no clue about the latest design concepts or conventions, as this is not something I keep up to date with. Second, my work and expertise is focussed strictly on building back-end operational solutions to business problems for which the aesthetic aspect is only marginally important most of the time. This is one of the only times that I've had to create something that is pleasing to the eye, but I'm not sure if it is or not lol Would you be willing to please take a look and tell me what your impressions are? Any feedback will be highly appreciated, and I will be happy to DM the link to anyone who is willing to help me out. submitted by /u/Sofistikat [link] [comments]

  • Worth A Listen
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Google Workspace provides a platform, a common ground, for all our internal teams and operations to collaboratively support our primary business goal, which is to deliver quality information to our readers quickly.
Get 20% off Google Workspace (Google Meet) Business Plan (AMERICAS): M9HNXHX3WC9H7YE
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Even if you’re small, you want people to see you as a professional business. If you’re still growing, you need the building blocks to get you where you want to be. I’ve learned so much about business through Google Workspace—I can’t imagine working without it.
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