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 – Summary: The journey of building startups for over 20 years has yielded several crucial lessons:
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.
Persistence: The key to overall success often lies in sheer perseverance and the refusal to quit, even in the face of early failures.
The Power of ‘No’: Turning down opportunities, especially during financially tough times, is crucial to avoid burnout and stay true to your goals.
Work Smart and Hard: While enjoying your work is vital, readiness to put in extra effort when needed is equally important.
Start Slowly: For new businesses, especially online, it’s advisable to start small and avoid getting entangled in bureaucracy before proving the business model.
Be Cautious with Growth: Rapid expansion can lead to financial strain. It’s better to grow at a sustainable pace.
Avoid Corporate Pitfalls: As businesses grow, maintaining a customer-centric and enjoyable work culture is essential, avoiding the trap of becoming overly corporate.
Embrace Remote Work: If possible, allowing remote work can save costs and increase employee productivity.
Simplicity in Tools: Using too many apps and tools can be counterproductive. Stick to a few that work best for your team.
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
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.
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.
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.
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.
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.
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.
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.
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?
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.
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
What I’ve learned in 20+ years of building startups – References:
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.
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.
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.
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).
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.
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.
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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Ive been bit in the ass by several projects over my decade long business career. Ive made postmoterm reports before, but its always baffled me how people let their failed undertakings get them down, sometimes they close their businesses altogether. No judgment, we're only humans. But I thought to give a few pointers as to how I make mine such that by the time I'm done I don't feel discouraged by what went wrong and all the money I spent... if anything I feel excited about what I'm going do do next! just a little advice 🙂 First thing (to remove all the depression out of it) is to remind yourself a postmortem report is meant to promote improvement and knowledge accumulation, not outline your failures. Its primary purpose is to direct the path towards increased performance in future works while avoiding risks. They are valuable, but be very careful. It’s tempting to commence a new project immediately after completing the previous one. Failing to run a project post-mortem can lead to a cycle of repeating past mistakes and achieving poor outcomes. Investing time into a postmortem is investing in your work’s future efficiency and effectiveness. Keep a clear and consistent framework. I created a standard template for postmortem reports. I make sure the vital details are included. This promotes consistency, allows trend analysis, and enables improvement over time. Be specific. I quantify the change and specify the affected metrics. I use direct quotations or references from communication logs to provide clarity. Embrace simplicity. The most direct solutions give the most effective results. Share examples that showcase the power of streamlined solutions. An example of this is the development of a script to synchronize databases. If possible, apply the KISS principle. Lastly, and most of all, use blameless language. Be very gentle with yourself. I run a company and I foster an environment of trust and growth by avoiding blame and divisive language. I always assume that my team members act in the project’s best interest. When I do it like this, it helps me stick to the agenda at hand, keep my feelings at bay, and I get to have a progressive meeting(s) with my team. It reminds me that business is business, and even the biggest companies undergo losses too. If that's hard for you, use a checklist and writedown some short pointers from here. I created a project management tool that snaps me back to the matter at hand as well, in fact most of my successful ideas came from these reports. I hope none of you need to write one, but if (and most likely when) you need to, you can pop on back here and hear it from my end 🙂 submitted by /u/MartinBaun [link] [comments]
How do you effectively research and analyze competitors' offerings to refine market positioning and craft a unique value proposition? Share your preferred tools, methods, and any automation used in this process. Additionally, could you provide examples of similar data-driven projects or tasks you've undertaken? submitted by /u/asya_stepko [link] [comments]
How do you effectively research and analyze competitors' offerings to refine market positioning and craft a unique value proposition? Share your preferred tools, methods, and any automation used in this process. Additionally, could you provide examples of similar data-driven projects or tasks you've undertaken? submitted by /u/asya_stepko [link] [comments]
I've started with one business name and have been serving mostly residential customers. I would like to shift to commercial (b2b) work and use a different name. That being said, I will still be doing some residential work. Can my business have two names? I'm thinking about things like my google listing and other customer facing content. An feedback is appreciated. submitted by /u/tacosurfbike [link] [comments]
My team at Pompeii Labs has one simple mission - providing valuable insights into how your business' clients and target market behave, think, and feel. With our tool, Dialog, we can survey thousands of people (in any demographic(s) you would like to see) simultaneously and deliver best in class reports in one day at a cost 96% cheaper than current market standards. If your company has a need for information at a reduced cost - please feel free to DM me or contact me via Email: [delahunt@pompeiilabs.com](mailto:delahunt@pompeiilabs.com) submitted by /u/PlentyNo5498 [link] [comments]
How do you convince your Spouse that working on Side Project or Dream project is no way less than working on 9-6 Job, one needs to wait as it takes time to see the results. My spouse feels had I invested heart and time in my full time job I would have got promoted by now. submitted by /u/pixobe [link] [comments]
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'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]
So recently I’ve heard a lot about, follow your passions and dreams and so on and so forth. Honestly I took some time out to think of what exactly I love and what I’m passionate about. My answer to my own question was weed. I been smoking it on and off for years now and it’s always been a consistent. I’ve always loved weed. It’s an industry that I’d love to get into. I doubt I’d feel as though I’m working if I’m working in this industry. My only issue is, I live in the UK. I am currently a medical cannabis user. I’d love to open up my own clinic. I’m currently 21 though and don’t have a lot of money to just open up a clinic in the first place. What’s the best way to go about following this dream of mine? submitted by /u/zeexwifi [link] [comments]
would to get everyone's opinion considering im in my mid 20's female living in a third world country. my business is mainly related to gifting but i have a feeling its going to be very slow. i dont have friends or family who would spread the word ahead either. submitted by /u/No_Decision1212 [link] [comments]
If you were to start an online business that could potentially lead you to $15k+ a month in profit.. Would you invest $500 to learn the knowledge you needed to succeed and how to set everything up and running? Or is that too much of an investment “into the unknown”? submitted by /u/TheLazyGirlSquad3 [link] [comments]
Hey r/Entrepreneur folks Here's the thing: Today, I'm setting aside some time to roast your landing page and offer a Personalized User Experience & Website Usability Audit report for the website absolutely free of charge. I just need some genuine feedback on the report and any ideas for improvement. Expect detailed reports similar to these: Sample Website Audit 1: Sample Website Audit 2: Just drop the URL of the website you'd like audited, and I'll reply with the audit report. Your support and insights are invaluable. Hoping that this audit report sparks some inspiration for you. And, of course, I'm eager to hear your thoughts and suggestions. Thanks in advance submitted by /u/trippy_hustler [link] [comments]
Hey, I compiled this Database on Notion that showcase places where you can list your startup for free and get first Users and also exposure & backlinks. Predominantly for SaaS but most could work for other startups too. What's Included in the List? 80+ Startup directories 110+ Facebook groups tagged by sector 170+ guest post opportunities 50+ Slack/Discord list 40+ Online communities Wanted to share the list with all! To get a free download just enter 0$ or you can buy me a coffee. https://submityoursaas.com/ Enjoy! submitted by /u/Ok_Cap9063 [link] [comments]
Hello entrepreneurs, I’m excited to share something I’ve been working on, born from years in finance and inspired by the critical need for businesses to weather financial storms: Seasfy. What is Seasfy? Seasfy is a financial resilience tool designed to help small to medium-sized enterprises (SMEs) predict and prepare for financial fluctuations. Think of it as a health check for your business's finances, ensuring you can stay robust, come rain or shine. Why Seasfy? Having seen the effects of financial crises first-hand and the regulations imposed on banks to prevent future collapses, I realized the power of stress testing – traditionally a big bank tool – could benefit all businesses. Seasfy democratizes this capability, offering it free to start, to help your business anticipate and manage financial risks effectively. Try It Out For Free We've launched on Product Hunt today, and I’d love your feedback. If you're curious about how Seasfy can safeguard your business finances, give our free stress test a try. https://www.producthunt.com/posts/seasfy-building-financial-resilience I'm here for any questions about financial health, stress testing, or anything else you're curious about. How do you currently manage financial unpredictability in your business? Looking forward to your thoughts and a great discussion! Thanks for checking it out! Daniel submitted by /u/danonino80 [link] [comments]
Running a business is hard enough, managing social media on top can feel like a whole other job! What are some of the biggest challenges you face when it comes to social media for your business? Scheduling? Analytics? Keeping up with engagement? I'm curious because I'm working on a new social media tool called SocialBu (new version: 2.0), and I'd love to hear your pain points! Maybe I can help! submitted by /u/usamaejazch [link] [comments]
Solo tech founder. SaaS. Bootstraped. Two years for pmf. Got fired from day job. Defaulted on loans. Living off the drips of savings. Family man. Lost a parent. Pile of stress. Got my 2nd PO last week. It's tough. Dark. Mind taxing. Keep moving the needle no matter what. submitted by /u/AC12Ted [link] [comments]
I am Peter, CEO of Unstatic. I have built 7 startups in the past 9 years, and the most successful startup is Habitify (https://www.habitify.me/) - a habit tracker started in 2015 (now 2.6M users, $100k MRR). After the success of Habitify, we believed that we had a strength in mobile app, so we want to dig deeper into this area. This led us to the decision to build Starion - A nocode app builder (https://starion.io/). Starion allows non-tech people to build apps easily and intuitively. How Starion went We finished feature by feature, fixed bug by bug. The product was improved significantly after a relatively short period of time. We released some versions, got some milestones. However, little did we know, all those milestones led us to a dead end. What we did wrong In order to make a project work, we need to consider: Target customers Their pains Our painkillers But we solely started from our ideas and assumptions without planning thoroughly. We thought we built for non-tech people, but we ended up bringing Typescript into the product. We thought our product was simple enough, but some people (including developers) did not know how to start building an app with Starion. We thought our product was the solution to build apps with nocode, but we could not articulate the problem clearly to begin with. Our team spent almost 2 years building into the void, without having any source of revenue. The way out After a period of no success, I decided to rethink the strategy with my team. My philosophy “Just build a good product, it will sell itself.” might need a re-consideration. It’s not wrong, it just needs some changes. Big time. AppAlloy came to life (https://appalloy.net/). "A good product is not determined by the builder, but by the user." With this mindset, we distributed the idea to the market before even building it. We dived into communities, utilized personal networks, asked non-biased questions. And we realized: Users really care about convenience Small wins are important, make it happen fast The product experience should be much more simple So we shorten the flow down to only two steps, based on the core principle of an app: DATA Now, customers just need to insert the data, we do the rest. Apps are created without any initial customization. Users have their fully functional app as a small win, then they can further customize it later on. The UI is clear and direct, guiding people to certain steps. Big lessons learned - One, do not assume. The market is more diverse than what you know. Build a product, bring it to the market. Gather real feedback. - Two, you succeeded once, doesn’t mean you will the next time. We tried so hard and were successful with Habitify. Hard work is crucial, but luck is vital as well. Succeeding with one startup cannot guarantee your next success at all. - Three, you failed once, keep trying, cuz your success might be right around the corner. What we can control is our actions. What we can’t (fully) control is the outcome. You are just one action away from your success. Keep going. To all entrepreneurs out there, we’re all in this together. Don’t lose sight of your dreams. Thanks for reading. What do you think we could do differently? submitted by /u/AppAlloy [link] [comments]
I will admit that ive read this book a few times and feel like it has motivated me to want to better my financial health. Ive done some research on kiyosaki and found he’s a fraud as well as giving bad advice in his book. I have some other books on economics and a book on investing ive been getting into but was wondering if anyone had a book they see as there bible for entrepreneurship or just even “getting rich”. I like reading if its knowledge I can genuinely apply to my life. A couple of books I really like are by an author ryan holiday ego is the enemy and perennial seller. Thanks! submitted by /u/Cool_Syllabub [link] [comments]
My wife and I created an activity book for kids ages 6-10. We’re getting 1,000 copies made and planning on launching on our website and Amazon November 1st. What specific things should we do to build interest from now till then? Our plan is: -blog posts proving value -many social media posts starting 3 months out (wife thinks it’s pointless to start posting now when we don’t have samples) What would/did you do to build an audience that cares? submitted by /u/AngryBowlofPopcorn [link] [comments]
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