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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Hey hey! I’m on maternity leave and I’ve been thinking a lot about my next move (and catering to my little one of course). When my mind wonders, I’ve always imagined myself being an entrepreneur/owning a business BUT I just don’t have the ideas or I get overwhelmed with the what ifssss. I’m a great worker, I can get pretty obsessive when I’m into something. When people ask me for advice, I love it and get a rush that I can help them. I’m someone who really enjoys working as a team, and it’s got me thinking, are there any people out there that have the idea 💡 but are looking for a partner to grow their business? Just thinking y’all, any advice/recommendations would be greatly appreciated 🥰. submitted by /u/CharacterCustomer336 [link] [comments]
The advice is always the same, but when you have a business idea the first thing you have to think about is “How am I going to sell this?” This is a question that few people ask but which should ALWAYS appear at the start of a venture. What channels will I use to distribute this product? What message will attract the audience? How do I turn visitors into customers? Focus on these questions before starting anything. Having this defined before you even start creating the product or service can be a game-changer. submitted by /u/Sarvaturi [link] [comments]
I posted stuff that got millions of views and thousands of comments. But I don’t know who those who have seen it, upvoted/downvoted, or commented on my posts. I know Reddit is an anonymous platform, and it's cringe to have a real face and name here. So I go against the wind. Just for one day, let’s break this rule and tell your story? submitted by /u/johnrushx [link] [comments]
The other day I read this story, and honestly blew my mind. I recommend you to spend 5' and read it. One day, a wealthy businessman vacationing in a small Caribbean coastal town saw a local fisherman taking a nap next to his boat after a seemingly fruitful day of fishing. “Why didn't you fish more?” - the businessman asked him. The fisherman replied, “With this small catch I have enough to meet my family's needs." Perplexed, the businessman replied, “Enough to live on? - asked - you should have caught more than that. With more hours of work you could buy a bigger boat to catch more fishes. And with the profits from the sale of the extra fish you could buy a fleet of boats.” “And what would I do next?” - the fisherman asked. "Well... with the rent from the fleet you could build the largest fish processing plant in the area and hire people to work there. You could turn it into an empire." “And then what?” "Then you could go public and become a multi-millionaire." - answer the businessman. "And then what?" The businessman replied, “Then you could live like a king with no worries. Swim in the sea every morning, fish for a while a day and spend the rest of the time with your family.” “What do you think I'm doing right now?” - smiled the fisherman. 🤯 mindblowing, isn't it? 🤯 The moral of this story is that sometimes we miss out on enjoying the little things in life by relentlessly pursuing more wealth, power and material possessions. It reminds us to value what really matters and not to neglect our happiness and free time for the sake of inordinate ambition. Fisherman and Businessman story submitted by /u/polisantiago [link] [comments]
I was really excited to make my first ever "$1K MRR Post" but I've been struggling to get the extra $8 for couples of days so I thought I would do the post nonetheless 😅 My SaaS: Me and my friends have built a direct booking website builder for Airbnb hosts. You paste your already existing Airbnb listing link into our tool and it will build a standalone direct booking website for that property. It syncs with all of your OTA calendars to avoid double bookings Manage your bookings Connects to Stripe to accept direct bookings Want to change something - simple - just drag-and-drop Our Funnel: Facebook content --> About 5% of web visits signup --> 7-day free trial --> About 12% of signups end up buying. What Works: Facebook is a gold mine. Airbnb hosts have their own communities and a lot of them are on Facebook. I'm an Airbnb host myself so I've joined a lot of Facebook groups where I try to particiapt Exceed expectations. The thing here is that... you can control this. We "Prime" our customers with our website by displaying the features they'll get if they pay. And those features are good-enough for them to give up their hard earned dollars since they sign up for our free trail. Once they sign up... we design their website without an extra charge, we design a logo for their business without an extra charge. And we do all this in 3-4 days. Clients don't expect this because that's not on the website, and they LOVE IT. Opinion leaders. In our industry we don't really have "influencers" per se. There are a lot of "experts" with their own Airbnb Youtube channels and masterclasses. They've become authoritative figures within the industry. Other Airbnb hosts listen to their advice. We've worked with one of them and it was a pretty insane boost to our business. He created a 4-5 min Youtube video showcasing our solution. Great communication. Once you have built up trust with your trial customers, personal Loom videos work GREAT! Every email I now send out I film a short Loom just pretty much saying the same thing that I wrote in the email. Clients love that. They feel appreciated, respected and cared for. What Doesn't Work: TikTok is still a mystery for me. I filmed couple of "value" TikToks showing how simple our solution is and what are the benefits of Direct Bookings WITHOUT trying to sell our software. I guess TikTok is hit or miss. For us... it is crickets there. There is a limit with Facebook. I tried to scale my Facebook strategy with multiple accounts but I got banned from some Facebook groups. Have to respect the rules. SEO. There is 0 search volume for our keywords. Although I'm still playing around with blogs and backlinks there is no real value add from that. Our current struggles: Top of the funnel. Distribution is key. I still haven't figured out a way on how to efficiently get to Airbnb hosts at scale in a controlled way/structure. We are getting a lot of requests for new features. Although this is good, it becomes really hard to mange all of those features. We have very limited resources to build those features. Our front-end developer started charging us WAY TOO much money... so we don't have a front-end dev now. Here are some experiments I want to try: Cold calling. I think that cold calling in our industry (software for Short Term Rentals) might be underutilised. I don't think that "Big Boys" such as Hostaway, Lodgify, Ownerrez etc do any cold calling. Plus, short term rental owners are super busy so having someone to talk with makes things happen 3x faster. Cold emailing. I have never tried cold emailing on a large scale with a concrete structure. Cold IG DMs reach out. Our tool is probably the only one that is optimised for social media use. And a lot of Airbnb hosts are on IG. So this strategy has been on my mind. It just a matter of figuring out a scalable and automated way to do that. Long form content. I know that Youtube can do a lot for us. So I really have to put my head down and film a bunch of VALUE Youtube videos for Airbnb hosts. The End 🙂 For other founders out there (if you've read this far)... it all boils down "Experiments" --> how many different things and strategies you can test in a given period. Then it is just a matter of time until you hit something BIG. Once that happens... double down on it and I think 😅 the rest should follow. We've been operating for 9-10 months now but 5 months ago we had a pivot. There is a lot more I could cover... Those who want to check out what we've built, the tool is called "Bookl.ee" submitted by /u/TasAdams [link] [comments]
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]
How is your week going? This is a safe space, feel free to rant & let go. (My rant) No one in my close circle is an entrepreneur and everyone has been telling me to focus on my 9 -5 and or apply for a second job. I'm losing motivation and no one close to me is helping lol, but I'm sticking to my plan and will push through the rutt. What are you feeling? submitted by /u/iwishiwasanonionring [link] [comments]
5 years ago Sam Altman wrote a blog post called “How to be successful”. And looking at where Sam is today, he meets every definition of the word "successful". But beyond his own accomplishments, during his time as President of YC, Sam worked with thousands of ultra successful founders every day. He studied them. Learned from them. Noticed the common traits they all shared. This makes him uniquely qualified to talk about what it takes to become wildly successful. While the post is great, it’s a long read (> 3,000 words long). So, here’s the TLDR version: Compound Yourself: Embrace compounding growth, both in business and in personal development, aiming for an ever-increasing trajectory of success. Have Almost Too Much Self-Belief: Cultivate strong self-belief, even to the point of delusion at times, as it fuels perseverance and conviction in your ideas. Learn to Think Independently: Foster original thinking and a willingness to pursue contrarian ideas, prioritizing truth-seeking and embracing failure. Get Good at "Sales": Develop strong communication skills and conviction in what you're selling, whether it's ideas, products, or yourself. Make It Easy to Take Risks: Create an environment conducive to taking risks, recognizing that most people overestimate risk and underestimate reward. Focus: Prioritize focus over mere effort, ensuring that your efforts are directed towards the most impactful tasks. Work Hard: Acknowledge the importance of hard work, recognizing its compounding effects and the role it plays in long-term success. Be Bold: Pursue ambitious goals and visions, even if they seem far-fetched or contrarian. Be Wilful: Assert your agency in shaping your own future, persisting in the face of challenges and setbacks. Be Hard to Compete With: Build leverage, unique skills, and a strong network to differentiate yourself and become difficult to replicate. Build a Network: Cultivate relationships with talented individuals, collaborate effectively, and identify and empower emerging talent. You Get Rich by Owning Things: Recognize the importance of ownership and equity in wealth creation, whether in businesses, real estate, or intellectual property. Be Internally Driven: Focus on internal motivations and values rather than external validation, pursuing work that aligns with your personal sense of purpose and fulfilment. PS if you’re looking for a business idea to follow step 12, there are loads here. submitted by /u/hell0__w0rld [link] [comments]
Recently I found some advice from famous indie hackers that - to increase the chance of success, build 12 product in 12 months and then focus on those that make money. Alright I get that! To build 12 products in 12 months, you'll need to : think of an idea/problem, talk to relevant folks if they'd pay, build landing page, build product, launch or bring traffic, customer support, email marketing and whatnot. And doing all this for 12 products, can someone really commit enough time to make a product successful? Whats the hack here? Open my eyes. P.S. I'm currently building/managing 2 AI micro-SaaS. Takes shit amount of time. submitted by /u/ankit-saas [link] [comments]
I recently started a new agency called [Awwwly](https://awwwly.webflow.io/) that specializes in creating beautiful websites tailored for small businesses and startups. We offer a suite of services including web design, development, and content creation. Since our focus is on the small business/startup community, I wanted to reach out to fellow entrepreneurs for advice on the most effective ways to market our services: For online/digital marketing, what have you found to be the best channels? Paid ads, SEO, content marketing, communities like this etc.? Any platforms or tactics that provided the best ROI? In terms of traditional/offline marketing, what are some creative ways I could get in front of my target audience of small business owners? Local meetups, networking events, partnerships etc.? Are there any specific pain points, fears or objections I should be prepared to address when engaging with potential small business clients evaluating web services? As a new agency looking to build a solid client base, I'm really open to any tips, suggestions or lessons learned from your experiences with marketing/branding your own businesses and working with web designers/developers. If you'd like an overview of Awwwly, our mission is to be a one-stop solution for businesses to establish an online presence without dealing with the complexities and costs typically associated with launching premium web services. We've streamlined our process to be able to launch fully customized static websites, from concept to go-live, within just 3 weeks of design approval. This allows businesses to get up and running quickly with an affordable, high-quality digital presence... Appreciate all your wisdom! submitted by /u/LorestForest [link] [comments]
Hello, I've partially finished the first MVP of my SaaS. This time, I wanted things to be as serious as possible, so I went ahead and filed for an LTD for it, to stay legal. Until now, I've played all the roles in my project, I've been the designer and the developer. However, I'm feeling a bit lost in marketing. I only have traditional ideas, like linking a blog to it and creating/editing some videos for ads. But I still fear having 0 clients. So, I've had the idea of building it in public, like here and in forums. That way, I can at least ensure there will be a minority waiting for my project. Thoughts? submitted by /u/provengoat [link] [comments]
Hello fellow hustlers I am wondering if there are people here working in content and are willing to share some tips on content production outsourcing and delegation without directly employing a team. Some background, I have grown a social media account to 1.9m followers. Currently still edit the content myself. I use a couple of Ai tools to assist me in the production process. However, I am kind of reaching burn out, and I can definitely improve on quality as editing videos is not my biggest strength. I license/outsource the footage I use. The videos generate ad revenue directly on the host platform. it is my main source of income. Happy to answer any questions. It feels like this step has been long coming. But I am looking to design a more consistent and sustainable pipeline of content. Like from script writing to editing/graphics. Where would I start, and what are the best platforms to outsource? I have used fiverr for my outsourcing needs a few times and it seems pretty good. So do I just hire someone to write the story board, pass it on to an editor/graphic designer and then upload? Are there any good books that explain this sort of thing? submitted by /u/xSnipeZx [link] [comments]
Hello Reddit! I'm in possession of a 2000 square meter (~0.5 acre) plot located in a green belt zone of the capital city, with a stream running alongside. Here’s basic info: Climate: Continental, with distinct cold winters and warm summers. Regulations: It's agricultural land, so building options are limited (small structures like sheds are possible, but no major constructions). Restrictions: Camping and similar activities are off-limits due to its agricultural designation. These trees are wild, and can be removed (there is no value of them). Photo: https://ibb.co/KwCv67B I'm looking for innovative ways to utilize this space that go beyond traditional farming, especially ideas that can generate some side income. Do you have any non-agricultural suggestions or successful examples from similar scenarios? Any advice or ideas are greatly appreciated! submitted by /u/JuanZG [link] [comments]
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I recently started thinking how come as a society we cheer up for people who get a mortgage and will be tied up for 30 years and cannot loose their jobs. But the moment you mention that you might have to get a loan to build or scale your company suddenly everyone panics and see it as super risky. The risks are there for both but the rewards for trying to build something might bring way more than a house. I am super curious what is your opinion on this? submitted by /u/Pure_Wasabi5984 [link] [comments]
Hi All I'm working on a consumer app, and it's almost good to go. I'm thinking of doing a small-scale launch, mainly online. However, I don't have much money for ads. Any ideas on how I can pull this off effectively without spending much? submitted by /u/Miserable-Phrase-614 [link] [comments]
I come from a developing Asian country where Western companies hold a strong influence, affecting our GDP. As a 17-year-old aspiring entrepreneur, I'm curious about the businesses that were vital for your country's economy in the past. Thank you for sharing your wisdom. submitted by /u/FedMates [link] [comments]
I am curious to hear insights on how entrepreneurship has been for a lot of people, your current MRR, how you got there and some of the challenges you have faced , let’s hear your story and learn together submitted by /u/sky-builder [link] [comments]
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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