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.

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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.

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.

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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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  • Successful entrepreneurs, how do you manage daily tasks?
    by /u/CaLinOuRS38 on July 12, 2024 at 2:04 pm

    I would call myself a relatively successful entrepreneur, I have ADHD and absolutely gigantic issues with my ability to focus and organize things. It is part of the reason why I'm successful, but it means that all of the non-creative tasks require me roughly 2-5x as much time to carry them out well enough (if I spend twice the time a "normal" person would, I'll give myself a 7/10 - good enough, and 4-5x then I can give myself a 9-10/10 for the quality of the work and the fact that I couldn't have done it any better, which means I can actually take some pride in what I do). At what point do I get a part-time housekeeper? Currently, my schedule is: get up, shower and get dressed, go to work, attend meetings, etc., drive home when all the supermarkets are (almost) closed, get home after they're closed usually, take care of the dogs, order some food, eat with my girlfriend in front of the TV and go to bed. Rinse & repeat 6-7 days/week. I would like to go to the gym with my girlfriend, and spend some quality time with her/my mom/my friends, but we have 2 dogs we need to care for, a house to keep clean, groceries to purchase, clothes to clean and iron, etc., and it's starting to become quite difficult. I have more and more work, and I'm already stretched out way too thin. I'm currently hesitating between keeping my cleaning lady (1 time per week for 5 hours) and ordering high quality pre-made meals from a local company, or getting a part-time housekeeper (2-3 days/week for 8 hours each time) to cook, clean, do the dishes, the laundry, iron the clothes, and so on. Budget isn't an issue, if spending money improves my mental and physical health I'll gladly open my wallet. What is your experience with this? Has anyone had similar struggles? submitted by /u/CaLinOuRS38 [link] [comments]

  • Wanted to gather feedback on a language learning app idea
    by /u/Pleasant_Syllabub591 on July 12, 2024 at 1:33 pm

    Hey Everyone, I've been doing a lot of research on an exciting new application for language learning, drawing from my intensive experience learning Japanese. One of the biggest challenges I faced was finding high-quality listening and reading resources to practice these skills. My professor rarely provided listening or reading drills in my textbooks, and I often found myself seeking interactive exercises. While watching anime or YouTube videos is helpful, I sometimes want to practice more intensively. Interactive exercises that test my comprehension make a significant difference as opposed to only listening or reading a text. Another issue was the comprehension barrier with the texts I encountered. For instance, even simplified Japanese articles required me to open the dictionary multiple times. Here's my vision: I want to build an app with standard language learning features like Anki or a conversation bot, but with a unique twist. The app would create or find texts using vocabulary I'm already familiar with and quiz me on that vocabulary. Additionally, it would generate listening prompts on topics that interest me or select engaging media based on my interests, followed by vocabulary and comprehension questions. Using high-quality TTS, these prompts would feel very natural. What do you think about an application with highly customizable drills like this? Is there an app on the market that already offers this level of customizability? If you could have any feature in a language learning app, what would it be? I'd appreciate any feedback. I believe there's an opportunity here to create a new intermediate/advanced language platform that gives learners complete control over their learning experience. Thank you! submitted by /u/Pleasant_Syllabub591 [link] [comments]

  • “I want to build a mobile/web app” 770K USD over 4 years, MVP developer.
    by /u/Comfortable-Visual-5 on July 12, 2024 at 1:21 pm

    I’ve always found ppl to be curious about building a side hustle project and many times ppl feel afraid in reaching out and seeking guidance. I want you to ask me anything in terms of technicalities involved and I would love to answer queries around it. Over the last 4 years, I’ve built around 57 web apps and 68 mobile apps. The average MVP build ranged from 4-7k USD, some even on a much higher end given the complexity but I’ve shared the average cost. Out of all of them, I’ve seen success stories as well as found products which couldn’t get traction. I do have the whole day free and if you still think that you need explanation in detail, shoot me a dm. I have a loom subscription, I would send you a loom video where I would share in detail on how would it work in your case and what you can expect from it. I’m an idea validator(MVP builder) with no emotions attached. It’s an anonymous platform and I won’t be charging a single penny for anything. It all starts with curiosity, be curious and ask me anything! submitted by /u/Comfortable-Visual-5 [link] [comments]

  • *Please* stop dooming entrepreneurs to failure.
    by /u/UpsidesNetwork on July 12, 2024 at 1:12 pm

    Entreprenuership "culture" promotes that founders need to master every needed skill themselves, then execute solo. But, true skills mastery is often not possible in a reasonable timeframe. So, people end up burning themselves out, only to get "maybe good enough" at a bunch of stuff, then use it to execute in a suboptimal way. So, it's no wonder why the culture also promotes that entrepreneurs will likely fail and need to try again. This is all wrong. It's far smarter to collaborate with people who've already mastered some of the needed skills, get critical advice from people who already have real experience, and form partnerships for cross-promotion, etc. Then, we would be helping entrepreneurs succeed, instead of telling them they need to fail. TLDR; collaboration is the cheat code. submitted by /u/UpsidesNetwork [link] [comments]

  • Seeking Feedback on My New "Website as a Service" Business Idea
    by /u/sixty_sticks on July 12, 2024 at 12:58 pm

    Hi everyone! I'm a web and app developer based in the UK. After several months of searching for new roles, I've decided to channel my skills into starting my own "Website as a Service" business. Would be great if I could get your feedback on the following idea... What is it? Instead of charging a hefty one-time fee for a website, my company offers a complete website solution for an affordable monthly subscription. This makes it easier and more budget-friendly for small businesses to establish their online presence. Pricing: Single Page Website: £30/month (+ £20 one-time set-up fee) Multi-page Website (up to 5 pages): £50/month (+ £40 one-time set-up fee) Features: Design: Choose from 32 stunning templates, and we'll customise your site to match your brand. Hosting: Reliable, secure hosting with 24/7 uptime. Launch: Seamless publishing with your chosen domain name. Maintenance: We'll keep your website updated, secure, and running smoothly so you can focus on your business. Whether you're looking for a single-page site or a multi-page solution, we’ve got you covered. Plus, if you need extra features or additional pages, we offer custom solutions tailored to your unique needs. submitted by /u/sixty_sticks [link] [comments]

  • If you're considering selling your business, which factor is most important to you?
    by /u/nunziopresta on July 12, 2024 at 12:27 pm

    Selling Price: Getting the highest possible return on your investment. Finding the Right Buyer: Ensuring your business goes to someone who will continue its legacy. Timing the Market: Selling when market conditions are optimal. Transition Plan: Making sure the handover to the new owner is smooth and seamless. Moving On to the Next Chapter: Freeing yourself up for new opportunities and adventures. Share your thoughts and experiences! submitted by /u/nunziopresta [link] [comments]

  • I made my first $30 from my microsaas after 20 hours of a soft launch to Twitter.
    by /u/nooby-xviii on July 12, 2024 at 12:20 pm

    This is an extremely exciting moment for me since it's the first time I've ever made money from any of my microsaas projects! GridStats.pro, a website to create graphic visuals for your stats, is currently scheduled to launch on Monday, July 15. Yesterday, I pushed the production version and published a tweet about it and then bam! I made my first sale from the post after 12 hours, and I made another sale while I slept 🙂 I was trying to keep this short and inspirational, hopefully this makes you finish that project of yours as well! submitted by /u/nooby-xviii [link] [comments]

  • I built a free website that gives you quick summaries of the main news. It auto-updates every six hours. Hope you find it useful and helpful
    by /u/HaywardUCuddleme on July 12, 2024 at 12:15 pm

    https://theglobeataglance.com/ submitted by /u/HaywardUCuddleme [link] [comments]

  • We are looking for successful entrepreneurs in Australia ! (For an Interview)
    by /u/Heavy-State1115 on July 12, 2024 at 12:12 pm

    Hey guys, I'm a 26-year-old guy from Sydney, and I've recently started a YouTube channel. My channel films day-in-the-life type interviews, sharing the stories of established / successful entrepreneurs to show young "wannapreneurs" like myself what's truly possible out there. I believe there is a lot of "fake" content out there just to sell courses or promote something, and I want my channel to be different. My goal is to help young people expand their views on the types of businesses out there and encourage them to chase their dreams and build something of their own. We're currently reaching out to some people, but I thought it would be a good idea to post here and see if anyone is interested. If you are running a business and would like to share your story, it would be my absolute pleasure to connect with you. Please comment below with a brief description of your business, and I'd love to DM you to share more about my channel and discuss further. Thanks for your time, and I look forward to hearing from you! Have a good weekend. submitted by /u/Heavy-State1115 [link] [comments]

  • Escaping the rat Race
    by /u/snake_eaterMGS on July 12, 2024 at 11:56 am

    Hello! M, 33 Years Old. Lately, I've been a bit divided about my life goals. For the past few months, I haven't had a "normal corporate job" following a layoff, and I've been working on a business idea - Craft Beer and Craft Kombucha - which already has sales. I never felt very realized in the corporate ladder. My current income is: - €1910/ month (aprox. 1800 dollars) from rented properties, after accounting for loans - From my business, it's variable. I have fixed costs of about €500 ($400) per month, but at certain events I participate to sell the craft beer and Kombucha, I have €1000 in sales or about $600 in profit (example from one of the recent weekends) - $110.000 invested in IWDA (ETF) My question is: I have been thinking on “Am I right in pursuing the entrepreneurial path”? Or should I settle down and live a "normal" life? I've never felt very satisfied in a "normal" corporate life. Are these thought normal in this community? The income from the rented properties already gives me a good cushion, and I feel I can dedicate myself to the business without too much pressure to pay the bills. This is my venting, any idea or suggestion from an outsider would be welcome! submitted by /u/snake_eaterMGS [link] [comments]

  • Have you done manual cold email reach-outs as a founder and gotten better outcomes than with automations?
    by /u/mohanpierce0007 on July 12, 2024 at 11:27 am

    I was wondering how early-stage founders operate in terms of getting their first 10 customers. Does everyone look into Apollo for potential customer leads? Have they tried Apollo sequences and automation, failed, and ended up manually doing 100 emails a day via their Gmail or Superhuman? Have you gotten better results with that? I personally have experienced that automations end up more in spam! submitted by /u/mohanpierce0007 [link] [comments]

  • Cutting Edge Technology Startup
    by /u/blogger786amd on July 12, 2024 at 10:02 am

    Any startups here which has started business in 2024 in Artificial Intelligence or Blockchain and successful. Which type of services and products they are offering. What new services will have high demand in near future? submitted by /u/blogger786amd [link] [comments]

  • What can be taught and cannot be about entrepreneurship?
    by /u/ishwarjha on July 12, 2024 at 10:01 am

    Things that cannot be taught: In my view, you can teach the principles of entrepreneurship but not the passion for execution. You cannot teach what it takes to be successful. You cannot teach someone to have an execution plan and the ability to carry it out when no one is there to hold their hand or guide them day-to-day. You cannot teach how to create values and build a business or how to improve and transform it. Things that can be taught: However, you can teach how to prepare a business plan and present ideas with the right pitch deck. You can teach how to discover and implement the value curve in products or services. You can teach how to identify and execute a product’s unfair advantage. You can teach how to explain a product and uniquely position it with the right perspective. You can teach how to develop an idea into a product that people love and find valuable. You can teach how to research, innovate, and bring together people to build a product, ensuring that you ship the right product, service, or opportunity. Whether you agree or disagree, share your thoughts. submitted by /u/ishwarjha [link] [comments]

  • If you could have dinner with any financial expert (living or dead), who would it be and why?
    by /u/EdGavit on July 12, 2024 at 9:53 am

    I'd grab dinner with Larry Fink, the BlackRock boss - dude's got $4.3 trillion under his watch and probably knows more about the global money game than anyone alive! submitted by /u/EdGavit [link] [comments]

  • How many of you have an idea but haven't gotten started yet?
    by /u/Emotional_Abalone270 on July 12, 2024 at 9:30 am

    I'm at this part of my journey, I know what I want to do but taking that first step is so difficult and I have no idea why. submitted by /u/Emotional_Abalone270 [link] [comments]

  • It's not the tools you use
    by /u/BrandStories on July 12, 2024 at 8:37 am

    Tools can assist, but they don't define your success. A fancy laptop doesn't make you a tech wizard. A project management app won't turn you into an effective leader. A high-end camera doesn't make you a professional photographer. Too often, entrepreneurs rely on gadgets and software, thinking they can bypass the hard work and experience needed to truly excel. On the other hand, startups frequently mistake tools for talent and then wonder why their goals remain unattained. Tools are important, but they're just tools. Without the right mindset and dedication, they hold no power. With the right mindset and dedication, they amplify your abilities. submitted by /u/BrandStories [link] [comments]

  • For organic reach, should I start out giving out everything for free?
    by /u/rdpGuy on July 12, 2024 at 8:06 am

    Hi guys, I have a healthy and efficient eating plan that I developed and been applying to my self for years which I benefited a lot from. I ended up thinking of monetizing it. my plan is to reach organically using IG or YT where I encourage them to visit my landing page to buy my paid contents. but here's the tricky part. I feel like I have to give out almost everything for free to keep posting anything meaningful and might grab attention. is this the right way? will they still buy my paid contents when 90% of it is already shown? I've even heard someone saying that you should only talk about "Wows" than "Hows" but I have no idea how to keep generating meaningful contents that way. submitted by /u/rdpGuy [link] [comments]

  • Impact of Founders' Loan on Future Investment Viability?
    by /u/Designer_Cricket_312 on July 12, 2024 at 7:48 am

    Hi everyone, I'm facing a situation at my startup and would appreciate some advice. One of our cofounders is planning to exit suddenly, and to manage the buyback of their shares, we are considering putting $5000 from remaining cofounders as a loan to company. This step was necessary to maintain operations and stabilize the company cap table, especially given our long sales cycles. We're now planning to raise $300,000 in investment. How might this founders' loan affect our chances of securing the new investment? What concerns might potential investors have, and how can we address them? Is there a specific way to structure or communicate this situation to make it more acceptable to investors? Any insights or experiences shared would be highly valuable. Thanks in advance! submitted by /u/Designer_Cricket_312 [link] [comments]

  • Starting a Buisness
    by /u/Imaginary_Ad_5019 on July 12, 2024 at 5:29 am

    Im trying to reach at least one person that can help me get me set on the right direction. I do attic and crawl space insulation, I’ve been doing it for the last 4 years and made my bosses aloooot of money. I’m tired of getting paid peanuts when a job averages 5k. I feel like I got everything figured out and can easily do a job if I had a customer lined up but that’s where my problem starts. I’m not good at marketing and closing leads. Any advice will help. submitted by /u/Imaginary_Ad_5019 [link] [comments]

  • Making Friends
    by /u/000_PZero on July 12, 2024 at 4:55 am

    Obviously this path is extremely lonely. I'm looking to make some friends with a similar mindset. Maybe hang out over voice call or something together while working on individual projects. Looking to make a small group where we can pitch ideas, thoughts, and collaborate together on our own paths. Let me know what you think! submitted by /u/000_PZero [link] [comments]

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