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28 Comments

Should you work at a startup before founding your own?

I recently posted on IHs about how I have too many ideas and can't stick at one long enough to make it a business. I had some great feedback and advice - thanks everyone!

Since then, I've been thinking that my main problem is that I'm not disciplined enough in business because I haven't actually seen a startup in action. This leads me to think I should go and get a job at a startup and that will help me (in all areas) with my own.

Now I think about it, it seems obvious but doesn't seem to be advice that I've ever seen recommended.

Is it because as IHs we're so against working for others? Or is there something else I'm missing?

on September 17, 2022
  1. 6

    If your struggle is discipline, I don't see how working at a startup will fix that. If your struggle was experience/knowledge, then working at a startup first would make more sense to me.

    Is discipline really what you're struggling with or is it something deeper?

    1. 3

      I totally agree with this. You start by just doing, not waiting, planning and thinking when you’d start.

      From what I read I feel you might struggle with a mild imposter syndrome. Ever thought about that?

  2. 5

    I believe it's a matter of working in bigger teams to learn how they operate and how the business processes are planned and executed and how the teams are working together to make the goals happen. So for this purpose it doesn't matter if it's an enterprise or a growth-stage startup. The bigger the team, the more you'll learn about business processes.

    But, for learning how startups scale, I believe working in a startup that has just raised Series A gives you the most learning opportunities. You'll learn scale, team work, goal setting, and a lotttttt more.

    1. 3

      So for this purpose it doesn't matter if it's an enterprise or a growth-stage startup

      I have to disagree with this. The pace in a big and settled enterprise is much much slower than in a startup and I think if you want to get your own business, it is much much more interesting to go to a startup. You can see the pace everything goes, skipping some processes to make some deliveries that in a big company you would never skip.

      Also, if you are an IH, probably working at a big company is not for you. Of course your goal is to become one of these big companies, but I think the startup experience is much more worth it. Also, it is easier to create good relationships and get valuable contacts.

      1. 1

        I see your point. By bigger teams, I meant either in a startup or an enterprise and teams of like 3-5+ people, instead of 2-3.

        Let me re-phrase it this way: I believe working in a more mature team with about 5 people can teach you lots more than working in a young startup team that's figuring out how to go on. Even at an enterprise, you'll learn how you could improve the situation if you were the manager of that team.

        I don't believe working at enterprise is for specific type of people and isn't for IHs. It's not ideal but is full of valuable lessons & experience you won't learn anywhere else.

        Of course, both situations have valuable lessons for anyone. But for a first (and probably only)-time job, I believe working in a more mature team can take you to the point much faster. It doesn't matter how

  3. 3

    As someone who's worked almost exclusively at startups I would say do it. You'll learn so much in a relatively small amount of time.

    The trick is to keep your eyes and ears open and absorb as much as you can. Learn from the pitfalls and also from the wins so that you can apply it to what you're doing.

    It also teaches you a lot about leadership. Many of the startups I worked at failed and ended up closing down, meaning I ended up losing my job. But what I learned is that in most cases, it's due to bad leadership and management skills.

    So learn from all of that.

    If your problem is discipline, then working at a startup can also help with that, at least it did for me. Because you're on the clock. Startups are high risk, and if you don't perform you'll potentially lose your job. So I think maybe working under pressure can give you that push.

  4. 3

    It would be good but certainly not a pre-requisite. I am a living example of the opposite.

    IMO, it is the team or co-founders around you who can make this issue (if issue at all) non-existent

  5. 3

    I did. Sort of.

    Technically, I started my first business in college, but it never went anywhere beyond a small win in a local business competition.

    After that, reality set in and I had to get a job, so I spent 10 years at small startups. I was the first employee twice and it was a blast as well as an amazing learning experience.

    While working at other companies, I tried to start at least 10 of my own businesses during that period, but nothing really got going. Again, learned a ton and met a lot of good people though, so it was well worth it.

    Finally, when I did find something that took off, it took off fast. We did $1mm in revenue in year two and are about to hit $3mm in year three. It was wild how much all that early startup experience helped me when it came to hiring, selling, operating, and marketing my business.

    Obviously, there are a lot of paths to entrepreneurship, but I'm a big believer in learning from others by taking a job or two along the way.

  6. 2

    Identify how close you can be to the source, or the founders or CEO. If you're not working directly for them then it's going to be hard to figure out how to build a startup from 0.

    I was lucky that I got into a startup-sorta-business between the 7th and 30th employees. I was able to actually talk to CEO and Founders and learn what it took to build from zero.
    But it was in the entertainment industry so lots of existing relationships were used. That didn't help me with product. That didn't help me with marketing. What it did help me with was spirit, grit. Understanding the need to talk to users. Which that company didn't do at all.

    Instead of learning directly from the founders, I sorta looked at the gaps and wondered where I, a solo founder, could fill in those gaps. And this was repeated in what I was reading at the time: Patio11 writing on how a solo founder can both talk to a user and push code, sometimes in the same day. And that speed makes for great customers.

    I was high on the Patio11 ideas, and depressed that the company I worked for wasn't doing so great. Those combined and fermented and frothed into me doing my own side projects, learning to code, and ultimately going off on my own.

  7. 2

    I think it depends a lot. Your problem doesn't sound like something you can solve with working somewhere else. It seems to be more of a mindset issue (i have it too, and I've worked at multiple startups).

    You will definitely learn a lot working at other startups. But you might also learn the wrong things, depending on the founders, the company stage and other factors.

    As one example, you might work at a startup that is growing consistently but is actually being mismanaged. But you might not realize that because growth often masks bad management.

    I also dont think that you should always do the same as others (and yes, you can see what they do wrong and do it differently, but that could also just be another type of wrong).

    If your problem is that you cant stick to one project, that's really something only you can change. Try to decide based on a mix of data + passion.

    Test your ideas and stick to the one that is promising and that youre passionate about.

  8. 2

    It may work but there are 3 factors to take into account: the stage/type of a startup, the quality of the team, and your role.

    1. Typically, startups go onto a hiring spree after raising Series A, sometimes after Seed. Therefore, you are much less likely to get a job at a very early-stage startup, while that is exactly what you need if you want to observe the process of getting to product-market fit. Doesn't mean it's impossible – but the terms are going to be different from a typical "job". In particular, a big chunk of your pay will come in equity instead of salary, so you need to have low expenses or sufficient savings. Also, early-stage startups (at least good ones) are very conservative in hiring, so you need to be able to bring solid skills to the table.

    Working in a later-stage company is also useful: you can absorb the culture and speak to early employees. But if you want to minimize "time-to-market", this isn't your way.

    1. Many startups are bad, and they die because of bad practices you don't want to learn. This includes an insufficient focus on customers, low speed, bad culture, etc. You need to be very selective regarding the team you join, and this may be hard to evaluate without experience. One factor to look at is the character of a CEO: is she humble (underappreciated!), energetic, intelligent? My first job was at a startup, and it was mainly useful for getting to understand how I should never do:)

    2. You want to be in a product-related role, preferably a product manager. Starting and growing a product is the essence of product management, so you want to learn this profession. If I have to choose between going into early-stage company or getting a PM role, I would choose the latter. Marketing is also useful because startups die more often because of bad marketing, not bad tech.

    Overall, if you have time and some spare money, I would start working on a side hustle right now. This should be something super complex – it can be a newsletter or another simple subscription service. Other jobs can give some useful skills, but not to the degree that own project does. However, if you have very low experience and low savings, going full-time on building a startup may be unwise. In such a case, I hope the advice above will help to choose the right place to grow.

    Last words: if you end up at a bad startup, just drop it and move on. Life is too short to waste your time on healing wounds and unlearning bad patterns.

    All the luck!

  9. 2

    I think you're just going through the natural process of becoming an entrepreneur or startup employee, neither of which is better than the other. Working for a startup helps you prepare for your own startup the most in a way that you will experience the first-hand what to do and what not do to, as well as expanding your network in the startup community. Many people make the jump to become a founder without working for a startup. There's no single formula for success. It's kind of interesting that so many people ponder about founding startups for a long time but, oftentimes, they already made up their mind and know the decision. One thing you can do is that you can time-box your decision period, let's say for the next 2 months. If you still can't make a decision by then, you really shouldn't found your own startup. On the other hand, if you have enough conviction and faith, you won't even need 2 months. You probably already know the answer :)

  10. 2

    I think working at a startup like any other job, you gain insight into their knowledge and experience. You end up seeing mistakes they have made and the solutions to those mistakes, so you bypass those mistakes in your own endeavors. By avoiding those mistakes you end up gaining confidence and with confidence, you gain discipline.

  11. 2

    I think you have to join really early to learn what you need in the starting phase of your own project. I currently work for a startup but joined as the team was close to 20 people and the company already had a few major clients. I still learn a lot each day but it's similar to the saying learn from people which are a few steps further than you, not ten. In my experience its easy to join "too late" because this is when hiring starts.

  12. 2

    This article by Lawrence Jones tries to answer this exact question.

    The bottom line is, oh wonder, gaining experience. Having seen a startup go through different phases, you'll get things right in less time and even have an idea about what "right" looks like.

  13. 2

    I'd say there would be two ways ahead of you for getting enough experience and discipline, one is working on startups, especially in the early stages when the team is small, and you'll have the chance to work closely with the founders and should handle tasks in various subjects.

    The second way could be you starting multiple micro-saas ideas, trying to get the ideas off the ground in a way that you're sure some of these may or will fail. In this trial and error way, you'll learn a lot. and the most important lesson I'd say would be "embracing the failure" beside of all the important lessons learned being a founder/cofounder.

  14. 2

    If your ideas are not yet fully formed or if you have no idea where to start.
    Working at a startup will definitely speed up the process for you.

  15. 2

    Absolutely, you learn a lot fast and you understand how to operate.
    Don't join the first startup you find, aim for something where the founders have run another company before successfully ideally they've exited in a way or another.

    That guarantees that they have an ounce of success-rate and know what they're doing

  16. 2

    I mean it definitely would help, but I wouldn't go out of my way activly looking for a startup before starting my own.

    All start ups are unique.

  17. 2

    I used to think the same. But then I realised that the best way to learn is to make mistakes and If you are making mistakes then why not do it while building your own thing

  18. 2

    In my opinion, one must have the skillset and experience to run a startup. That experience could be earned from the first startup where you learnt a lot after making numerous mistakes and probably your startup was either semi successful or a complete failure or it could be from the job in some startup to understand how startup works.

  19. 2

    I would say it definitely helps to work in a startup before.

    I am not sure this is your problem though.

  20. 2

    Yeah, I'd say it will teach you discipline in terms of sticking at something until it's done because you can't just walk away from what you're working on when you're an employee - unless you quit. haha. It may also show you how hard it is and you could decide that you're better suited to being an employee than a founder. Anyway, hope it works out if you do go for it.

  21. 2

    Glad someone said this. It seems obvious to me too that you'd get some experience at a small startup first as it's very different from working at a big company. After graduating I worked for a bit then tried launching my own startup and failed. Didn't really see where I went wrong. Eventually, I worked at a startup with just a team of 4 and learnt so much. Most importantly that you have to wear a lot of hats. My job wasn't specific, just 'pitch-in' where needed kind of thing. After a year, I launched my second startup and it's still going strong 3 years later. I say work at a startup, it will really open your eyes.

  22. 2

    Hi Zach,

    During my student days, I worked for the companies for about two years. In my last year of university, I started my first own project. I have never worked for anyone since I graduated.

    All the time, I follow my own needs and passion. It might be a good choice if you think this work might be interesting and give me new experience. Trying to follow some recommendations if you don't want to work for someone won't work.

    There are many ways for being interpreter. Just do what you want to do and enjoy your way.

  23. 1

    🚀🙌🏻🏄🏻‍♂️

  24. 1

    It depends. I have been working in a startup from past 5 Years and learnt lot of things from scratch.

    So if the startup belongs to the same domain which you are interested in building something in future then it would definitely help you to increase the success rate by reducing mistakes which you have already done while working past.

  25. -1

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