December 31, 2019

Tough love for 2020: five mistakes holding IHers back

Rob Fitzpatrick @robfitz

A bit of tough love for 2020, based on some of the problems and challenges I've seen raised here. And all of which I've fallen for myself, at various times:

  1. Trying to bootstrap an idea which isn't easily bootstrappable
  2. Searching for magic bullet marketing before the product is right
  3. Chasing a customer segment you don't understand or have access to
  4. Trying to be "efficient" too soon
  5. Not allowing the mistakes required for soft skill growth


1 // Not all ideas are equally easy to bootstrap or make a living from. Some unavoidably require eventual funding, so "bootstrapping" is really just cross-subsidizing it with your savings/job until you can get a bit of funding and go a more traditional startup route. Others can't be monetized early (or enough), and are really just a multi-year hobby which might someday evolve. If you want quick, profitable bootstrapping, then rigorous idea selection is your single most powerful tool. Beware committing to the first idea you happen to fall in love with. No idea is good or bad in a vacuum -- it can only good or bad for you and your goals, right now.

(I'm not saying either of these are strictly doomed — and you can certainly find successful examples of both — but they're definitely going to require a longer, harder, and more expensive journey than the typical IndieHackers success story.)

2 // If you're spending all your time and energy worrying about tactical marketing while you still have less-than-stellar retention, zero evangelical recommendations from users, and no deeply engaged users, then you are probably worrying about the wrong thing. It's unlikely that clever marketing can pull you out of the mud, whereas a better product or a more important problem certainly might. Note that this only applies to tactical pursuits (e.g. affiliate, SEO, influencers, social media, partnerships, cold emails, etc etc). Stuff like good copywriting, on the other hand, is essential for new users to understand what's happening and needs to be done early.

(A notable exception to the above guideline includes any marketing activity which builds a long-term asset like a mailing list, blog subscribers, active community, or deep personal network, since that's a lifelong asset which will help all future projects.)


3 // If you personally know zero of your potential customers or need to ask how to find a single conversation or user, you're in big trouble and probably need to find a way to get in contact with real customers (in real life) in order to build the baseline understanding and empathy to start making reasonable product and copy decisions. If you can't find a single friend or have a single coffee with someone similar to your customers, how in the world are you going to build a product they adore and find a way to reach them at scale? It's straightforward to resolve though: either go meet some people or switch customer segments to someone you actually enjoy hanging out with.

(An exception to the above is when you already do know them but are either unaware of how to use an extended personal network or are too shy to reach out to folks. Fortunately, both of these problems are quick fixes once you identify them.)


4 // The previous problem (not knowing any customers) leads folks to send out cold emails to strangers. And those emails don't work very well, since they never do, and then the person goes on IH and asks completely the wrong question. They should be asking how to fix either their (1) idea selection or (2) connectedness to customers. But instead, they ask how to write better cold emails. This is incredibly backwards, and is an example of the common problem of trying to be "efficient" too early. We know that customers come from sales, so we are hugely tempted to skip ahead to just giving the sales pitch via cold emails. But this sort of outreach doesn't work and acts as a subtle sort of busywork which consumes all their time without allowing for actual progress. A similar thing thing happens when folks want to go through the motions of learning from customers without actually having to do the uncomfortable work of talking to a human. So they send out a big survey, wasting a bunch of time to learn superficialities at scale. In my experience, I'd always rather have two actual conversations over two thousand survey results. These sorts of false grabs at "efficiency" are like building your house on a foundation of sand.

(This issue is tougher to identify and debug since it manifests in so many forms. In general though, I'd follow Steven Pressfield's advice that whenever something makes you so nervous that you're finding every excuse and workaround to avoid it, you should recognize that discomfort as your soul's way of telling you that you really need to just go ahead and get it done the hard way.)


5 // Lastly, when you start attempting some of these new soft skills (and stuff like idea selection which lacks immediate feedback), you're going to screw them up. That's fine. Would you expect to learn a new language without hitting any compiler errors? Could you learn to skateboard without falling on your ass? If you flee forever when it first goes wrong, then you'll permanently have that gap in your skillset, making your indie career far harder than it needs to be.


In any case, good luck and best wishes.

  1. 6

    I’m soooo on board with #3! To me this is the biggest “mistake” I’m seeing (on IH and elsewhere) with lots of products being built today.

    “I made a thing, where do I find users?” sets you up big time for wasting lots of time trying to find a segment where your product sticks (or not) - this can also drain your personal motivation and funds.

    1. 3

      There is a major exception to #3:

      If you are expert in the field, you need much less input from users. Effectively, because of your past experience, you've already done years or decades of ethnographic study (observed your users in their natural habitat, i.e. at work).

      You don't need to ask a tiny sample of users what they want, because you have already seen what a much larger sample needs.

      1. 1

        Still, you have to determine what your product will look like, how it works, what the value prop is, how to talk to potential users, where to find them etc.

        1. 1

          Yep, absolutely you need to do those things, but the difference is that you don't necessarily need to do them by talking to a tiny sample over coffee. E.g. if you are an expect then building the product based mainly on your own cohesive vision and measuring messaging mainly by AB testing with a large sample is a realistic alternative.

  2. 3

    Refreshing read to start the year, Rob!

    If we made a bingo out of this post I'd have bingoed long ago!

    My key takeaway is: do the painful things.

    I know this list didn't try to be complete but I think another major mistake IHers make is giving up too early. Which takes me to a more philosophical but still real pitfall, we do need to care about what the project is about to be able to keep working on it when the initial motivation fades. Money is an incentive but it should be a byproduct of our work and not the goal. I've come across way too many people not giving a damn about their projects (that's why the sideproject component of IHers is a strength), many times they aren't even aware of how little they care about what their product actually does. When you do care, #3 becomes less of a problem, which I think it's the most common of the ones you listed.

  3. 3

    Man, this post is a living example of content marketing.

    I instantly bought your book "Mom test" after reading all those amazing pieces of advice here :-)

    1. 2

      Ten dollars an hour, here I come :P.

      (Hope it proves useful though. Shout if you have questions.)

      1. 2

        Thanks! I just had a quick glance on the introduction and this piece

        They are, in one way or another, forcing people to say something nice about their business. They use heavy-handed questions like “do you think it’s a good idea” and shatter their prize.

        it's an indie hacker mindset in nutshell. I truly hope this book will as good as it starts.

  4. 2

    If you’re nervous or uncomfortable about doing something to help your business you should probably be doing that thing.

    This is my guide.

  5. 2

    I have done the cold emails thing once. I can say for me it was just an escape from actually having to talk to actual people.

  6. 2

    This is a fantastic post! I'm sure all five points will help a lot of people with their businesses and I hope numbers 2 and 4 can even help make this corner of the internet a bit nicer of a place, too.

  7. 2

    This is a fantastic list and I've definitely made all of these mistakes myself over the past few years! I don't know whether it's just me but I am starting to wonder whether some of these are mistakes that are actually really difficult to properly understand until you've learnt them the hard way (which is why #5 is so important)?

    1. 2

      That's something I've wondered about plenty over the years. Speaking personally, the advice has never prevented me from making the mistake, but it has helped me recognize my mistake sooner, sometimes with time to correct it, and sometimes with a chance to do better next time. Whereas if I'm trying to figure it all out myself, I would sometimes fail to even be aware of what I was doing wrong, and would repeat the same blunder ad nauseum. Hopefully it's fully preventative in at least some cases though :P

      1. 3

        That's a really interesting point around it not necessarily preventing the mistake but giving you the awareness to catch it earlier when it does happen. Now you've said it that definitely matches up with my experience and I'm glad I'm not the only one that does this as well :)

        I think part of it is also that it's really really hard to convey the true cost of some of these mistakes until you've felt the pain yourself and that's often the thing that then helps to embed it as part of your thought process going forward. I wish there was a shortcut to this part but I haven't managed to find it myself yet!

  8. 1

    This one might be just me, but I've noticed lately:

    1. Not taking time to understand the existing competitive and cooperative landscape (i.e. market(s)) up front (or as part of idea validation / mom testing)
  9. 1

    Great tips! Thanks rob!

  10. 1

    Great advice, thanks Rob!

  11. 1

    Thank you for the guide!

  12. 4

    This comment was deleted 8 months ago.

    1. 2


      You may have misunderstood the title of Patrick's book, "The Mom Test" :)

    2. 2

      Hah, wish I had you as the hype man for everything I write ;)

      1. 0

        This comment was deleted 8 months ago.

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