What were your worst mistakes the first time you founded?

Sam Bauer
78 replies
It's not my first time, but I've sometimes the impression that I do the same mistakes again and again without recognizing it.


Sreekanth PM
Approaching the wrong people who don't value your time.
@sreekanth850 That's an interesting point. Did you find a strategy how to avoid this?
Sreekanth PM
@timz_flowers this happened when i approached people to become cofounders. I stopped it an started hiring people and later if they found mingling with our culture and thoughts i will discuss about the possible association. There is no such single solution for this.
@jiebu_li ? is this meant to be a constructive comment?
@sreekanth850 what I heard, it makes sense to distribute the shares equally between the founders in order to create a stable construction, when big investments flow in and to avoid confusion at that point in time. When you want an employee to participate, normally you put some visop/esop options in place, as a founder is supposed to be someone who invests their time and money into the product. It's difficult to pay somebody as an employee, taking all the economic risk yourself, and later give them relevant shares - this would create an imbalance, except of visop, where they participate with investing their time and passion, getting less money, but stock options. then there's the tax problem. if the company created real value (eg by acquiring investments), then you can not hand over shares to the employee (except of visop) without subjecting him to immediate taxation. How will you deal with these issues?
@jiebu_li dear jiebu li, I did not want to be rude, but I count that kind of cynical contribution as part of the derogatory social media culture that we want to overcome in order to become a constructive and positive collective. everybody here is struggling with building an impactful product and helping the world to thrive. I'm happy to see your positive contributions.
Uljan Sharka
I feel your question, and I concluded that if you're innovating and you're not making any mistakes, it means you're not doing anything new. @rrhoover, what are your thoughts?
@rrhoover @deleted-2823528 totally true - for me it feels like I need a 360x360 knowledge as a founder (finance, legals, contracting, human resource, psychology, social media, community building, product building, software development, UX, advertising, marketing, pricing, market research, organisational development...) - much is new, but even if I did it before, time and context have changed, and even I have have changed - and of course the product is a total first move (what else)... so nobody to follow except of in analogies...
Teo Deleanu
My 50 cents on this: 1. Overthinking(as in doing too much research, analysis) 2. Doing things without research - but at least delivering 3. Having co-founders with the same skills means somebody has to do something that is not probably the best at.
@teodeleanu ah, so you mean complementary skill distribution between the co-founders - yes, totally agree here.
Aaron O'Leary
Founding when I already had too much on my hands. Had great intentions but burnt out and the product failed due to that
@aaronoleary How did it come that you had too much on your hands?
Anamika Chaudhary
This is my first time with entrepreneurship so I guess I will know in a few years!! 😅 But thanks for the thread, i can at least learn other people's mistakes
Stefan Wirth
Building behind closed doors for too long. Being scared to launch an incomplete Product / MVP. Always 🚢
@nafetswirth I read from a guy who was doing a successful launch here, that he recommended to have a perfectly working product in place. Would you then recommend to do a prelaunch somewhere else and then come to PH or doing the imperfect launch here?
Stefan Wirth
@timz_flowers It depends on what you want to achieve, plus there is no one size fits all answer, if I have side projects I launch them here early to measure demand and to see how much time I wanna put into fleshing them out. If you have a team working on something bigger or is a space where people are very used to super polished apps then I think you should reconsider. But building out in the open is probably one of the best things you can do, might be just in a specific community or give it to some early adopters and work on it with them etc.
Sreekar Channapragada
@nafetswirth my team and I are fighting this fear daily. We plan to launch a beta next month but the question always remains "How much should the product evolve before existing?"
Splitting a company equally among founders, with no sweat equity structure or conditions. People's priorities change, and most do not have the persistence and determination to persevere on an idea for long periods. Your co-founders begin to work less hours. Promises are made, and broken. Excuses are given. You still believe, but don't want to carry your entire team. You now regret the equal split agreement you made. All these issues could have been avoided by having a simple sweat equity structure.
@andrewc3 can you elaborate a bit on what that means for you?
@timz_flowers I assume you mean the sweat equity structure? I currently use a simple 1 share per hour worked system. Timesheets are submitted and shares rewarded accordingly. Capital investment, purchases and bills are reimbursed with shares at an agreed upon rate. The good thing about a system like this, is that your team is incentivized to work more on the project, or risk being diluted out. It also accommodates for holidays, sick leave, part time contributions and so on.
@andrewc3 are you paying real money in addition?
@timz_flowers Unfortunately I have no real money rolling in yet. Hopefully that will change =D With equity payment for staff, I'll have a separate share pool for staff and pay from there. This prevents founder's equity from being diluted out, while also serving the purpose of attracting and retaining talent.
Melissa Kwan
I didn't start with asking myself "what kind of lifestyle do I want to lead?"...instead, I built a business and tried to live my life around it. I suffered almost every day because I built a company that wasn't authentically myself. This time around, I'm changing that!
@melissa_kwan Thank you Melissa, this is perhaps one of the most fundamental questions of all, that you are pointing to. Nothing to add.
Samantha Merlivat
Taking too long to make decisions. It cost me a lot of time in the first year. I'm quite risk averse so I always wanted to consider all information, options, risks, etc, but on at least one occasion, no (quick) decision cost me more than a bad decision. I'm much better at decision-making now, but still learning to trust my gut. Curious if that's something that comes easily to most people....
@samanthamerlivat Same same here. But this has also an advantage: by investigating your uncertainty, you dive deep into your understanding. When you start a bit later than others from there, you start from solid ground. But important: you must make the decision to make decisions, otherwise you never stop diving. The easy part in this: you only have to make one reliable decision.... and you sound like you did already. Great.
Sean Kane
Building for scale in the initial developments, before fully proving the model. Yes, it would have avoided some refactoring, but ultimately it put the cart before the horse.
@sean_kane1 haha, yes I understand that problem entirely. Thank you, I will ever have this funny pic before my inner eyes: "the cart before the horse". Ok, I'm perhaps also driving with such kind of vehicle at the moment... now we have to learn in the middle of the manoeuvre to make an elegant turn around, without losing track while accelerating speed.
Samuel Dirksz
Partnering with friends without documenting everything.
@samuel_dirksz1 Samuel, I have a question: it sounds to me like a bit of a paradox in your description - if they were real friends, would you still think legal documentation is mandatory? The question behind my question is: Did your understanding of friendship develop since then or did it vanish?
Samuel Dirksz
@timz_flowers the things is with setting up a business, you need a clear goals, agreements on how to get there etc. Saying this to one another is one thing, but when shit hits the fan how will your word stand against another without having this on paper? For any business with friends, family, partners, business associates need to documented for in good times and bad times. Things are clear for everyone, for evaluation and building on. Without it, you risk complications and when things aren't understood they way you intended too. And our friendship ended, shit hit the fan, 'the friend' showed his true face and commitment which lead to disappointments and eventually closing down the business after, in this case I, cleaned up the shit ;)
@samuel_dirksz1 Thank you Samuel, for sharing. I have also some experience in this field. I founded 3 companies by now and all of them with different friends and family. The first one lasted for 2 decades and times were sometimes extremely hard, in the end we separated due to various reasons, like different development of interest, but we managed to stay friends and family and are still in good contact. The newest one I founded with a very close friend and my wife. We have contracts in place, like the legal documentation of the company or a rough loan agreement for our early investments. But nothing more specific, as the future is too uncertain to pack all contingencies in detailed stipulations - so far my understanding. Which kinds of stipulations would you recommend for the company building with a friend or partner?
Samuel Dirksz
@timz_flowers Thanks for sharing, of course there are many exceptions however you hear a lot around success, more than failures. Luckily that attitude is changing of the taboe around it. I would recommend agreeing on a documenting the business plan, even if its an MVP and when changes are made, this is a joint decision. Same goes for the amount time one invests and what this means in return when you start makeing money. What is fair is up to a joint decision again. Also your role and responsibility that comes with it. Not in minor detail but important to have clear understanding your input and output in the company. When it comes to capital/money, this is often a relation killer, how much of your profits will go back in the company, how much will one take out. Your part depends on the agreement. If this is clear then this is no need for arguing when the company is successfull or when shits hits the fan.
@samuel_dirksz1 Ok, Samuel, thanks for sharing your insights and experiences here. We circumvented some of the questions you raised by simply sharing the decision power, so there are literally no decisions to be made without all of the 3 founders agreeing. Taking out money (a future problem hopefully) for example would be something that needs 3 signatures. We will see what happens, when overwhelming success or activity brings pressure into the system, but at the moment I follow the rules to keep it simple and to trust in our rationality and mutual empathy. I will take your recommendations into consideration as we are also planning to branch out side businesses with people from farer circles, so we have to build up a general understanding in this field. Thank you!
Paco vera
Spend to much time designing the product instead of building it
@francisco_chim What is in your understanding the difference between designing and building?
Paco vera
@timz_flowers Well, i spend to much time with trying to make the pixel perfect layout on Figma insted of take the code and start to building the thing.
Paco vera
Hire a freelancer dev that steel al the work and sell to other people
@francisco_chim Oh, that's a really bad experience, sorry to hear that, Paco. What is your takeaway from that event? Could you tell me, what you decided to change in future projects to avoid these kinds of occurrences?
Paco vera
@timz_flowers Hi sam, well that was a very dramatic experience cause i lost all my savings BUT, i learn in the bad way this: Trust in your capabilities and learn the stuff that can save you a lot of money, so, i learn to code, to build my next thing and in this way the things get easier, because i can build a team of devs and communicate with them in a natural way. So that steel of this guy, change my life.
@francisco_chim Great to hear that. So you grew through a bad experience to a person with more skills and capacities to explore your real potentials. I'm sure you will succeed on a much higher level, thanks to your insightful attitude to learn from bad events for the good.
My biggest mistake was never fixing my problems using technology. I was focused on running after potential clients and solving their own problems. I guess I was scared to fix my own problems as they were too complex and seemed impossible. So the safer option was to fix theirs. My latest platform was built to solve my problems. And couple of users, +500 daily active users also have their problems solved.
@rotimi_je_suis Rotimi, could you elaborate a bit on what the difference between their and your problems is? I would love to get a tangible picture of the problems and the typological difference between them.
@timz_flowers I found their problems to be very much basic. For example, "App to schedule posts to Facebook", "Software to perform some automated spreadsheet stuff". Most of the problems I have are linked with real life problems. For example, privacy and security. In the past 3years, I have focused more on solving my problems and it has been rewarding. Even though building the tech platforms have been quite difficult, I feel like I'm doing something worth my time. It'll take a while to succeed, but that's the chance I'm willing to take :)
@rotimi_je_suis now I understand, well done, good decision to focus on problems you want to have solved for yourself in order to have expertise and passion
Salman Younas
For me, it was => not sharing the idea and getting feedback as early as possible.
@salman_younas How long did you wait and what happened during this period? And did you build after sharing anything on that idea or did you lose the determination to implement it somehow eventually?
Salman Younas
@timz_flowers I was about 2 months into the development of that particular product. It was the best idea ever, but only in my imagination. I shared it with my peers but it was too late. They pointed out some universal flaws that I hadn't thought of previously. Eventually, I ended giving up on that product.
@salman_younas Salman, thank you for your honesty. I think the most important aspect in that honesty is the one towards yourself, as you can iterate your imagination to a higher level by honestly analysing it and improving it to deal with more complexity and to come to better conclusions and intuitions. But one question is remaining for me: imagine you would have known the flaws in advance to creating the idea - would you have been able to tweak it and improve it in way that an even better product would have been possible?
Salman Younas
@timz_flowers Sam, it wasn't just possible to continue on the product and I had to give up on it. If I had known those flaws in advance, I wouldn't even had started working on it.
Tim J
We took advice from our investors to heart and it steered us away from building something either of us would use.
@timbjones What is your conclusion based on this experience?
Katie Ames
Being intellectually scatterbrained (lots of things that are fun and interesting and relevant... are not supporting your core business). There's a good chance that spending my time commenting on PH is an example of me not focusing on my core business - whoops!
@katie_ames understand, but is Virtual Community Building and launch preparation not a part of the business?
Katie Ames
@timz_flowers Sure, but also, it can be easy to spend too much time on it - the same way any good thing can become something you're spending too much time on.
@katie_ames so true! at the moment I'm starting our Virtual Community Building and it's so hard for me, so I spend much of my time in doing it. As you are experienced, perhaps you could give me some tips in this discussion: https://www.producthunt.com/make... - would be nice to get your perspective.
Maximilian Torggler
My biggest mistake: Not taking marketing serious. I lived in the "Build-It-And-They-Will-Come Wonderland" for too long.
@scriptify Maximilian, how will you approach the marketing aspect of product building next time, after this experience? Will you improve your own skills on it? Or will you bring in somebody with the skills?
Maximilian Torggler
@timz_flowers I will definitely expand my knowledge on that topic, actually I've already read 2 books, many tutorials and articles regarding marketing and man, that was so eye opening. It was like opening Pandora's box after years of procrastinating on it. The thing is, for most of that knowledge, it felt like it always lied directly in front of me, I was just blind on my marketing eye.
@scriptify Could you give the 3 most important bullets on your insights and share the book?
Maximilian Torggler
@timz_flowers "Traction: how any startup can achieve explosive customer growth" is the title of the book. Main takeaways: - Marketing is not as hard as it seems, you just need to adjust your mindset and always look out for new opportunities. Most importantly, you need to be proactive about it. - Create a clear strategy with clearly defined goals, e.g. 1000 site visitors. Then try out the different channels and methods for your strategy. Stick to the strategy which moves the needle most and try out all of it's variants - Not all marketing has to be strictly online. Also consider uncommon ways of reaching your customers, e.g. paper magazine ads or crazy PR stunts I'm by no means an expert on this topic and just starting out, let's see where this journey takes me
@scriptify wow, cool man, very precious tips and the book sounds promising!! great knowledge transfer
Ahmed Elsamadisi
I read books! I go why would someone do that. I make the mistake and think ... I should write a book and tell people about these mistakes. The biggest mistake is not taking care of yourself. If you are CEO your energy is so important and affects the team so always remember that when you are pushing yourself. Today, we launched on ProductHunt and my team literally told me that I need to make sure I sleep in because when I don't sleep enough I get anxious and that leads to the team being anxious.
@ahmed_elsamadisi Ahmed, what is the product you have launched?