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.

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  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.

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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.


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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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Storytelling Effect People prefer and better remember stories than facts alone Watching, listening, hearing, or reading a story activates the same regions of the brain as those engaged when actually performing these actions in real life. 🧠 Don't show your product. Tell a story "The most powerful person is the storyteller." - Steve Jobs Research - Rob Walker story: In 2009, Rob Walker bought 200 objects from eBay for a total sum of $129. He then asked 200 authors to create a story for each object. Rob then sold those 200 objects with included stories on eBay again. He sold them for $8000. That's a 6202% increase in value. 5. Pratfall Effect A simple blunder or mistake of a person can improve the attractiveness or likability of that person The same goes for a brand. But here's the catch... Your brand needs to be well-perceived in the first place. 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Inaction Inertia Effect When missing an offer once you are likely to miss an offer twice When people see that you're giving big discounts frivolously every month or week, they tend to ignore them after a while. The perceived value of your product lowers with each discount 🧠Strategize your discounts Short-term gains are cool, but have you ever implemented a long-term pricing strategy? • Every person is different. Create an email sequence that will split your contacts into specific groups. Then customize the discounts for each group 8. Stepping Stones Any task you want your customers to do, needs to be broken down into smaller, attainable steps, otherwise, a person will get discouraged 🧠Viral refferal program When creating a referral program the most important reward is the first one. The first reward has to be both achievable and attractive to motivate people to participate. 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  • I feel like I am wasting my 20s
    by /u/Minimum_Cartoonist42 on May 8, 2024 at 12:51 pm

    I've been hanging around here, soaking up all your awesome success stories, and I've gotta say, you guys are seriously inspiring. But now, I'm itching to get in on the action myself. I'm a 24-year-old woman with loads of time on my hands and a hunger for experience and growth. I don’t want to waste my 20s. I feel like I'm wasting my sharp mind, and I'm desperately looking for something to channel all my energy into. I have been actively searching for full-time Virtual Assistant roles, and I thought of no better place to post than here. I have some experience with social media management and lead generation, and while I may not have a ton of experience yet, I'm eager to learn, highly trainable, and I've got a keen eye for detail. While financial compensation is important due to my obligations to pay my bills and support my family, what I'm really after is the chance to learn from someone more experienced than me while supporting their journey and helping them achieve work-life balance (WLB). So, if you've got any projects that need an extra set of hands, repetitive tasks that keep dragging you down, or tasks you’re itching to delegate, hit me up. I’m your girl! submitted by /u/Minimum_Cartoonist42 [link] [comments]

  • What anchors you?
    by /u/flypinkocean on May 8, 2024 at 11:59 am

    I found love from my life partner (feeling supported that I don’t actually need to succeed in my business but just give my best) and religion (praying, conversation with God and myself helps). What works for you? submitted by /u/flypinkocean [link] [comments]

  • I have nearly £3000/mo of product sat on my desk and I have absolutely no idea how to sell it.
    by /u/vegandtwomeat on May 8, 2024 at 11:15 am

    I'm a fairly competent developer and I've written an entire pet-tag service from scratch, trying to plug some gaps that I've seen with current offerings. I've designed and purchased 1200 physical tags from a supplier on Alibaba, which are now sat on my desk. They're retailing for £2.89/month (or £1/month for extra tags per order) and I've got various offers/discount codes. Once PayPal take their cut, I'll get about £2.45/mo... so on my desk sits potentially £2940/mo (in an ideal world where none ever get cancelled, no extra tags are purchased etc, but still a decent side-income when these cost me about 20p each to get printed and shipped), and that's if I never sold more than those 1200... I'd like this to be an ongoing, growing venture. The tags themselves are stylish, modern, about the size of a £1 and contain a QR code that takes you to the pet profile with things like name, temperament, vet details, owner details (if they choose to share). When scanned, a GPS location of the phone scanning it is sent to the pet owner via text & email, the scanner can also contact the pet owner direct from the tag without ever revealing their info. We inform all vets in a 15 mile radius if your pet is lost, we auto generate lost pet posters for the owner to print or share online, we offer 6 free replacements per year etc... almost ALL of this is handled by automation (which I have a background in) & AI so my interaction with the system is minimal, other than to watch over it, respond to customer emails and physically post orders. I use PayPal to handle the subscriptions so that customers can transparently and easily cancel at any time (just going on our competitor socials shows a huge number of people struggling to cancel and just getting charged every month). Obviously that £2.45 profit on each goes toward web hosting costs, ongoing coding & security audits, text & email services that I use etc first, and then the moment I can afford it I want to start paying a professional web dev agency to co-manage the codebase & security as well as paying accountants, virtual PA companies to help with customer care etc, something else which is super important to me and that a lot of my competitors seem to lack. I know it's tiny numbers, but I've given about 30 away so far which are all being used by local folk; I set up a waiting list for a couple of months and they absolutely flew out and I've had nothing but overwhelmingly positive feedback on them, which shows me the product & service must be at least half decent. I've also sold 16 locally through posting on our local Facebook pages, friend referrals and recommendations etc, which tells me people are happy to pay monthly. So here's where I fall down, and that's sales on any kind of scale... there's 17 million pet owners in the UK, so even just getting in front of a small percentage of those. I haven't got a clue HOW to get them out there in front of potential customers, other than paid ads, and that isn't viable currently. I was selling a similar product (Dementia/ICE tags) using Meta ads and had a decent amount of success (generating about £300/month recurring revenue from those) until around Feb when the whole Meta ads system seems to have taken a total nosedive. Currently ~£500 in the hole on Meta ads and not a single sale on my pet tags. I'm trying to run Google Ads but once I start adding negative keywords of my competitors (Crumb etc) then imps/clicks drop off a cliff and Google is really struggling to spend my budget. Again, so far, no sales from Google Ads either. So I'm interested in what kinds of older-school, organic sales channels I might look into trying? So far I've emailed just under 2000 pet walker/groomer/services companies across the country and had a lot of "good luck" replies but no sales or joint promotion ventures. I've approached pet shops in my area & beyond to stock them, but all of them either currently stock competitors or won't stock subscription based items. Any direction or pointers would be much appreciated. I'm not looking for any quick fixes, if I can shift this initial 1200 within say, a year, that'd be great. Thanks in advance for your time! submitted by /u/vegandtwomeat [link] [comments]

  • What's the most appealing aspect of buying an existing business rather than starting from scratch?
    by /u/nunziopresta on May 8, 2024 at 11:12 am

    Looking forward to reading your comments. submitted by /u/nunziopresta [link] [comments]

  • I will Roast Your Landing page & Provide Page Design, Usability, and UX Report using AI (Free for today)
    by /u/trippy_hustler on May 8, 2024 at 9:57 am

    Hey r/Entrepreneur folks Here's the thing: Today, I'm setting aside some time to roast your landing page and offer a Personalized User Experience & Website Usability Audit report for the website absolutely free of charge. I just need some genuine feedback on the report and any ideas for improvement. Expect detailed reports similar to these: Sample Website Audit 1: Sample Website Audit 2: Just drop the URL of the website you'd like audited, and I'll reply with the audit report. Your support and insights are invaluable. Hoping that this audit report sparks some inspiration for you. And, of course, I'm eager to hear your thoughts and suggestions. Thanks in advance submitted by /u/trippy_hustler [link] [comments]

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