What I’ve learned in 20+ years of building startups

What I've learned in 20+ years of building startups.

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What I’ve learned in 20+ years of building startups…

In the fast-paced world of startups, two decades of experience can teach you invaluable lessons. From the trenches of entrepreneurial ventures, here are the distilled wisdom and key takeaways from a seasoned startup veteran’s 20-plus-year journey.

What I've learned in 20+ years of building startups
What I’ve learned in 20+ years of building startups

What I’ve learned in 20+ years of building startups – Summary: The journey of building startups for over 20 years has yielded several crucial lessons:

  1. Fail Well: Failure is a common part of the startup process, with success in only a fraction of attempts. It’s important to accept failure as a stepping stone.
  2. Persistence: The key to overall success often lies in sheer perseverance and the refusal to quit, even in the face of early failures.
  3. The Power of ‘No’: Turning down opportunities, especially during financially tough times, is crucial to avoid burnout and stay true to your goals.
  4. Work Smart and Hard: While enjoying your work is vital, readiness to put in extra effort when needed is equally important.
  5. Start Slowly: For new businesses, especially online, it’s advisable to start small and avoid getting entangled in bureaucracy before proving the business model.
  6. Be Cautious with Growth: Rapid expansion can lead to financial strain. It’s better to grow at a sustainable pace.
  7. Avoid Corporate Pitfalls: As businesses grow, maintaining a customer-centric and enjoyable work culture is essential, avoiding the trap of becoming overly corporate.
  8. Embrace Remote Work: If possible, allowing remote work can save costs and increase employee productivity.
  9. Simplicity in Tools: Using too many apps and tools can be counterproductive. Stick to a few that work best for your team.
  10. Maintain Relationships: Keeping doors open with past collaborators is crucial, as business landscapes and relationships are ever-changing.

What I’ve learned in 20+ years of building startups – Lessons Learned in Detail

  1. Fail Well. You’ve heard it a million times before: ideas are easy; execution is hard. Execution is incredibly hard. And even if something works well for a while, it might not work sustainably forever. I fail a lot. I’d say my ideas are successful maybe 2/10 times, and that’s probably going easy on myself.

  2. Keep Going. The difference between overall success and failure, is usually as simple as not quitting. Most people don’t have the stomach for point #1 and give up way too quickly.

  3. Saying No. Especially if you didn’t have a particularly good month and it’s coming up on the 1st (bill time), it’s hard to say “No” to new income, but if you know it’s something you’ll hate doing, it could be better in the long-run to not take it or else face getting burnt out.

  4. Work Smart (and sometimes hard). I would hazard to guess that most of us do this because we hate the limitations and grind of the traditional 9-5? Most of us are more likely to be accused of being workaholics rather than being allergic to hard work, but it certainly helps if you enjoy what you do. That said, it can’t be cushy all the time. Sometimes you gotta put in a little elbow grease.

  5. Start Slow. I’ve helped many clients start their own businesses and I always try to urge them to pace themselves. They want instant results and they put the cart before the horse. Especially for online businesses, you don’t need a business license, LLC, trademark, lawyer, and an accountant before you’ve even made your first dollar! Prove that the thing actually works and is making enough money before worrying about all the red tape.

  6. Slow Down Again (when things start to go well). Most company owners get overly excited when things start to go well, start hiring more people, doing whatever they can to pour fuel on the fire, but usually end up suffocating the fire instead. Wait, just wait. Things might plateau or take a dip and suddenly you’re hemorrhaging money.

  7. Fancy Titles. At a certain stage of growth, egos shift, money changes people. What was once a customer-centric company that was fun to work at becomes more corporate by the day. Just because “that’s the way they’ve always done it” in terms of the structure of dino corps of old, that’s never a good reason to keep doing it that way.

  8. Stay Home. If your employee’s work can be done remotely, why are you wasting all that money on office space just to stress your workers out with commute and being somewhere they resent being, which studies have shown only make them less productive anyway?

  9. Keep it Simple. Don’t follow trends and sign you or your team up for every new tool or app that comes along just because they’re popular. Basecamp, Slack, Signal, HubSpot, Hootsuite, Google Workspace, Zoom (I despise Zoom), etc. More apps doesn’t mean more organization. Pick one or two options and use them to their full potential.

  10. Keep Doors Open. While you’ll inevitably become too busy to say “Yes” to everything, try to keep doors open for everyone you’ve already established a beneficial working relationship with. Nothing lasts forever, and that might be the lesson I learned the harshest way of all. More on that below…


What I’ve learned in 20+ years of building startups: A personal note that might be helpful to anyone who’s struggling

Some years back (around 2015), we sold the company my partner and I built that was paying our salaries. During those years, I closed a lot of doors, especially with clients because I was cushy with my salary, and didn’t want to spend time on other relationships and hustles I previously built up over the years.

I had a really rough few years after we sold and the money ran out where I almost threw in the towel and went back to a traditional 9-5 job. I could barely scrape rent together and went without groceries for longer than I’m comfortable admitting.

There’s no shame in doing what you’ve gotta do to keep food on the table, but the thought of “going back” was deeply depressing for me. Luckily, I managed to struggle my way through, building up clients again.

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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.


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Source: r/Entrepreneur


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What I’ve learned in 20+ years of building startups – References:

  1. Entrepreneurship Blogs and Websites: Look for blogs from successful entrepreneurs or business coaches. Sites like Entrepreneur (entrepreneur.com), Forbes Entrepreneurs Section (https://forbes.com/entrepreneurs), and Harvard Business Review (hbr.org) often have valuable articles on startup strategies and entrepreneurial journeys.
  2. Startup Case Studies: Websites like Inc. Magazine (inc.com) and Fast Company (fastcompany.com) frequently publish case studies and stories about startups and entrepreneurial experiences.
  3. Business and Tech News Websites: Platforms like TechCrunch (techcrunch.com), Business Insider (businessinsider.com), and The Wall Street Journal’s Business section (https://wsj.com/news/business) are good for staying updated on the latest in startup trends and business strategies.
  4. Remote Work and Productivity Tools Blogs: For insights on remote work and productivity tools, check out blogs from companies like Basecamp (basecamp.com), Slack (https://slack.com/blog), and Zoom (blog.zoom.us).
  5. Online Business Forums and Communities: Websites like Reddit’s Entrepreneur subreddit (https://reddit.com/r/Entrepreneur) or startup-focused forums on sites like Quora (quora.com) can provide real-world advice and experiences from various business owners.
  6. LinkedIn Articles and Thought Leaders: Following successful entrepreneurs and business thought leaders on LinkedIn can provide you with a plethora of insights and firsthand accounts of business experiences.
  7. Business and Entrepreneurship Books: Websites of authors who have written extensively on startups and entrepreneurship, such as Guy Kawasaki or Seth Godin, often have blogs and articles that are invaluable to entrepreneurs.

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  • I am a 21 year old entrepreneur and I’m gonna lay out my experience and all the advice I can give. Please read I wish I had this when I started.
    by /u/Flat-Cherry-6761 on April 19, 2024 at 6:22 pm

    Hey everyone, I’m 21 from Canada. So you are interested in embarking on this journey, I was also. But wow I wish I read this first. I’m currently on a vacation I decided to take after finishing my last exam and took last night to think about me when I was 18 and what I’d wanna know and I couldn’t think of anywhere better then here to write it cause I remember reading these helplessly looking for answers. To start I’ll explain me a bit. At 18 was lost to go to university or start my own thing. Ended up doing both. Studying Finance and running 2 businesses in the same industry now that help one another. Currently doing around 65k a month net profit from the 2 of them. Feels amazing and I’m lucky to have been able to do this in the period of time I did but these results only came after doing 1 at first and doing it for 9 months with little to 0 results took me 9 months to hit 10k per month net profit. Still studying in school funny enough, almost done and just do still see value in it. As much as people say it’s not needed, you go to someone and say you’re running a business and studying the older people respect it a lot and opens the floor to them most times questioning you. Anyway I want to get into the biggest lessons and things I’ve learnt by doing this. To start, it’s not easy this isn’t the way to get quick cash and if you think it is you are highly mistaken. If you feel lost now be ready to feel 10x more lost when you start. There is 0 certainty that’s why it’s so good to start when young. If you’re 26+ it’s probably time to start figuring out life getting a job and providing in some way shape or form. Not saying it’s impossible cause I know lots of people older than me who have but there is just more risk that comes with it. If you are young it’s the perfect time to fail. If your young you can still fail 20x and nothing will change, don’t get me wrong these 2 businesses I have now I failed 3 others before the first one working. Will get more into failure soon and the main conclusion I have of why it happens. This part will mainly be the starting of the business. Don’t start a business and the next day go ok I need for form a corporation, I need to hire 5 people I need to do this that and that. Work at it for a while alone first understand what you are even doing and the different parts of the business how are you gonna run a business if you yourself don’t even know the parts of the business. Make cash then worry about the setting it up fully and the hiring of people. Another really important thing you need to keep in mind as soon as u hire someone you are now providing for them, they are counting on you to pay there bills. You have to take this seriously. You are never really gonna feel 100% I’m making more money then I ever thought I would but every single day I wake up stressed and unknowing Of what the future hold. This feeling of uncertainty will never leave my favourite person in the world Alex hormozi talks about this saying you never really know if what you are doing is going to pay of. It’s the most true thing in the world. Only thing you can do is work as hard as you can to make sure it does. Failure was mainly due to this one reason, lack of effort and discipline. Nothing happens over night, you aren’t gonna see results the first month maybe even the 5-6-7-8 month for me it took me till month 9 to feel like I had something. By saying this I’m mainly saying if you don’t try long enough you will never really know if what u are doing works or not. Most people find an idea, think wow this is an amazing idea, try, realize how hard it is and quit. Onto the next, famous quote if you chase 2 rabbits your aren’t gonna catch 1. If you keep going after that point on being down when you realize it’s hard a little while down the line you will feel the same way about the idea just with a lot more knowledge. Grass is always greener (Ties into failure) This is like the 1 thing if you take anything from this to really drive into your head. The grass is always greener. You always are gonna think there is something better, always gonna hear of new ideas don’t stick to what you are doing and continue to grow or else you are gonna jump around and never find success. This is going back to the point on chasing 2 rabbits. You aren’t gonna catch any if you do this. If you have one thing stick to it, like me eventually a year into it working I’ve just started a second thing. Only reason why was it was the biggest issue I was facing I could not find a good person to do this service for my business so I solved the problem by making my own. These 2 work hand and hand. Sacrifice Be ready to have your life change, when I started I was the guy who went out every weekend, loved to party see friends ect… I’m not saying that disappears, but it’ll diminish and it’s something you really gotta consider if you are looking to do this. Will you be find missing that big time party cause you have a meeting the next day? Are you find waking up at 6am and working till 2 am some days? Cause that’s almost every day of my life. You are gonna have times you are so stressed out and lost but trust me we all do and eventually you will be able to understand why you did it.My friends get mad at me saying why won’t you come out and I’ve lost about 5 friends since doing this and now have 2 guys who both also do similar things and we all understand one another I’ll get more into this in the networking section tho, just be ready and know you are gonna be giving up more then you think you need to trade off the small things for the big things and be ready to know you might miss out on some different memories with friends. Spending money, this is really important when starting and u make for example 10k a month. This doesn’t mean go on a trip, buy some cool clothes. It means the thing you are doing is working and figure out how you can take that 10k know what you need to live and re invest the rest into growing yourself and the business. This does not mean try to scale too fast take it at the same speed you were before just adding in pieces to the puzzle that are gonna help you. Don’t over hire, like I said before you hire someone, they are now counting on you. couple guys I started the same time as started spending going on trips now they are restarting because they didn’t live the same way they were before. Yea it’s hard not to go do those things but if you compound what you are doing into more more more then eventually it won’t even matter. Funding your business when I started, I was doing the business for 6 months, working at a bar bartending. I did this to be able to hold the business afloat. unless you have money from family or other sources this is something also to note, work somewhere, fund the business until the business can keep itself afloat don’t just dive in not knowing. Get results then try doing it alone and scaling. This is also why it’s important to know what you need and don’t need; at the start it was just me for 6-7 months doing it all until I physically couldn’t do it alone. Till then go on fiver Upwork hire cheap people for small tedious jobs. Don’t hire a full-time employee. Find a mentor I was lucky enough to meet my mentor while I was starting, working at the bar bartending, Sure enough one day a guy sat at the bar top, I just lost my best client I had at the time that day and we started talking. I explained to him what happened, and he just gave me his business card said email me and come into my office tomorrow let’s sit down. Sure, enough he owned one of the biggest VC companies in my city. He gave me his advice and I owe a lot to him till today. Any time I need help I reach out and he’s there. Relationships Treat clients, employees and mentors and even competitors as good as you would treat your mom. I can’t stress this enough, if you have a meeting be there 5 minutes early. If you have a service due for someone finish it before you were supposed to and do things they didn’t even pay for. Give a service so good that they go to there friend and say how good you did. This is how you build a name in the industry. When I say competitors I mean don’t look at them like this. No matter what the industry is there is room for the both of you, get in contact, talk share things of value and they will as well. Who you are Don’t become the guy who thinks he’s better then others just because your doing well. You will fail. Be honest don’t lie to people your working with, if you can’t do something don’t do it. If your behind try your absolute best to catch up. Don’t change who you are as a person just because now your making money or you will loose it I’ve seen countless people I know do this and eventually loose it all. Networking, networking is what I owe it all to, if it’s being in a discord, reaching out to people on Instagram or twitter. Likeminded people find one another and the random meetings you have, and calls and chats will lead to more then you can imagine. This comes with you friends a lot of the time your old buddies might not be there 6 months down the line because you might be on a different path some will understand some will be jealous some will be happy just all depends on the type of person they are. Take risks. , by taking risks I don’t mean buy 5000 more items then your last sale but go to that event you don’t know you will get anything from. Reach out to that person you think you have no chance of signing. Post in that blog u don’t think anyone will read it. Little things like this for me always led to something of value most times it’s not noticed the day of but 3 months down the line one guys number you got at this event you catch up sure enough you guys can help one another. Overall all I want you to know if your reading this feeling lost or confused. Stick to it, that feeling for me hasn’t gone away. Don’t think 10-20-30k a month is gonna make you feel different, if you aren’t already happy money isn’t gonna change anything. Build something that makes you happier then the money it brings. If you read this and still want to do it then do it, but don’t do it for 3 weeks and quit. Commit for the next 6 months to one thing network. Provide value and work hard and undoubtedly you will see some form of success from it. Realize your gonna have to give up a lot when doing this and it’s in no way shape or form easy and shit I don’t even know if it’s still worth, I see people I know having fun together but right now I’m in a villa laying in the sun drinking a pina collada at 1pm. So it feels kinda worth it. Other then that please dont try to get in touch with me I unfortunately won’t do it. I need to still learn a lot before mentoring anyone just thought this might help someone. I’ll respond to a couple questions just want to have this so a couple people can hopefully shed some light on what they are getting into and how to make the most out of it. I let it all out here, if you want to have more stuff like this go on YouTube listen to business YouTubers and podcasts you will learn tons. Read books and just stick to the plan. You got this and best of luck to all of you! I’m routing for you! submitted by /u/Flat-Cherry-6761 [link] [comments]

  • How do you build partnerships, the right way?
    by /u/marius_mixsave on April 19, 2024 at 5:12 pm

    About two weeks ago we hit the 500 customers milestone. And I think it's time to try a new distribution channel. Affiliates. - How do you guys build partnerships with other companies? - Learnings along the way? Mistakes you've made? - Any resources to read, before making the first step? - Ideas that would work for our business? (The business is offering discounts to popular software, in exchange for a membership) Thanks in advance! submitted by /u/marius_mixsave [link] [comments]

  • The One Platform that 3x’ed My Income as a Creator
    by /u/Big_Win844 on April 19, 2024 at 4:56 pm

    "I need more traffic to my offers" "I need to go viral on TikTok" "I need more money as a creator" Only one of those statements are true: You need more money as a creator. But you don't need to go viral or generate a "ton" more traffic in order to make more money in your creator business. The truth? Making more money does not mean that you need to make more content. In fact, I've decreased my content output by 60% and have made three times more money by doing so. The change? I stopped optimizing my business to build a "brand" and started optimizing my business for "cash." Here's the difference, instead of: - Creating TikTok Videos -> Writing Daily-ish Emails - Growing my social media following -> Growing my email subscribers - Driving traffic direct to offer -> Driving traffic direct to funnel Are you catching my clue? If your goal is to build a brand, focus on social media. If your goal is to make money, double down on email marketing. More importantly, optimize your business for cash. The simple way I do this? Content (Cash - Content Revenue Share Platforms) -> Email List -> Newsletter Referral (Cash) -> Limited Time Offer (More Cash) Stop focusing on your traffic stats, start focusing on the dollars that will actually make a difference in your life. submitted by /u/Big_Win844 [link] [comments]

  • Why are so many people comfortable creating scam/unethical companies?
    by /u/archive_spirit on April 19, 2024 at 12:49 pm

    To preface this, I work in the supplement industry so the scam companies I'm describing are mainly from there. But that being said, these types of companies seem to exist in most fields (e.g., gambling apps, predatory microtransaction games, etc. etc.) The more time I spend in entrepreneurship, the more I feel like I'm losing faith in humanity. Every day I see a new company emerge peddling products that the founders obviously know don't work, or worse, that are actively bad for their customers. The latest example I've seen is the emerging trend of electrolyte companies (I know I'm a little late to this and they've been around for a while). Well, suffice to say, the business model around these products is sound: the margins are super solid, the target demo seems to be growing as exercise is getting bigger and bigger. There's only one problem: supplementing with electrolytes does NOTHING to performance. In other words, many of these large companies with revenues in excess of $50 million are selling products that do not work. And yet these companies seem to be run by intelligent people who should obviously know better. Indeed, in many cases the founders of these companies actively dispute the scientific evidence as it emerges, even though its plain they are wrong. Are we as a society just getting to a "post-truth" era that, combined with capitalism, results in an environment where everyone tacitly agrees that we can sell whatever we want, even if it is complete BS? I'm a capitalist as much as the next person, but even I admit that I'm not comfortable knowingly ripping people off just to make a buck. And yes, I know this is a naive post as huge companies have been doing terrible things for ever. It just seems that the threshold has gotten lower and lower and I'm very sad to see it. Rant over. ​ submitted by /u/archive_spirit [link] [comments]

  • It's been 8 months now since I left my job. and it's been amazing
    by /u/manojahi77 on April 19, 2024 at 12:08 pm

    It's been 8 months now since I left my job and went all in into my things. and it's been amazing I wake up when I want. Earlier I had to wake up at 8 AM just because I needed to go to the office at 9 AM. I sleep whenever I want. take a nap in the afternoon. I don't have unnecessary meetings now. earlier there was a meeting for everything. I travel to wherever I want to go. I just need my laptop. earlier I had to ask for permission for leaves and for a certain number of days only. If I don't want to work any day, I just don't work. I feel free. In 8 months I have worked with 10 awesome founders. Talked with numerous awesome founders and people. Been to Singapore, Malaysia, UAE, India Last month I was in mountainous areas for a couple of weeks. Once you go all in into whatever you are doing, you will not ever want to go back. Edit: What happened in those 8 months income wise? Sold 2 products Started a Development company in Singapore which is crossing $70K in revenue soon. I also launched multiple products earlier as well but those were B2C, but now my focus is on B2B SaaS products. My old journey So far launched 40+ products. Shut down some of them because they were not getting traction, got some initial users but not more than that. In 2020, I started a fintech product, able to reach to 5K users and tried to raise funds but failed. but now my focus is on bootstrapping as much as I can. Background I am CS graduate from 2017. But building products since 2015. Always wanted to do something on my own but never had a chance because of situations in life like everybody does. But last year I thought to F it, you only live once. And went on to do what I always wanted to do. Journey is long, and We keep pushing submitted by /u/manojahi77 [link] [comments]

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