Team, Investors, Marketing, Risk Management, Technology - whatever it is. What have you learned from it? What could you have done to prevent making the mistake in the first place?
Ask HN: What was your biggest business mistake?
1–10 of 23 posts
Re: Ask HN: What was your biggest business mistake?
#2Didn't seek product/market fit quickly. A couple years ago, a friend and I started a real-time social shopping tool that we'd hoped to pitch to online retailers.
We spent months and months just building and building. We had a small team of developers working with us as well. It took us about 10 months to get our first prototype out only to find that no one wanted it -- not consumers nor retailers. By that point, morale had already started to drop, because everyone on the team thought we were just spinning our wheels and couldn't see any traction. Instead of spending another few months building in the dark, at that point, I mocked up something quickly in Photoshop and started pitching different ideas to retailers to see what people were interested in. I was amazed that retailers could understand what kind of product I was talking about just by seeing a mock and without actually having a demo or a prototype. After going back and forth on different design iterations, (I'm not a designer, so it was even more remarkable that potential customers could understand my mocks) we finally hit upon one that was of interest to many retailers.
Although we piloted and signed with retailers, unfortunately, it was already too late. The sales cycle with retailers is quite slow, and many of the larger firms plan for their website a year in advance. So we would not have even gotten the data needed to prove out the success of our idea for at least another year.
Speed to find product/market fit was something I completely did not understand then. I should have started circulating mocks on day 1.
Re: Ask HN: What was your biggest business mistake?
#3Thinking if you build it they will come. It doesn't. You have to go out and sell, you have to push harder than the other guy, who may be bigger, stronger and cheaper than you. You still have to do it. You have to get rejected and have your skin make a Rhino's hide look sensitive.
Re: Ask HN: What was your biggest business mistake?
#4Trying to run a service-based dev business to support creation of products. That consulting grew to consume 100% of our usable time and resulted in a period of pretty intense burnout, personally.
Re: Ask HN: What was your biggest business mistake?
#5Communication is vital. If communication breaks down then everything else turns to shit.
Also, handshakes don't cut it as much as we may want them to. I'd love to be able to trust people, but in matters where money is involved no one can be trusted.
I learned this the hard way. Please, use my mistakes to your advantage.
Re: Ask HN: What was your biggest business mistake?
#6Trying to run a service-based dev business to support creation of products. That consulting grew to consume 100% of our usable time and resulted in a period of pretty intense burnout, personally.
If you're in this situation, you might try honing your focus - if you can zero in on the most lucrative/time segments of your consulting practice, you may be able to make this work.
This does depends greatly on your client mix and financial situation.
Re: Ask HN: What was your biggest business mistake?
#7Communication is vital. If communication breaks down then everything else turns to shit. Also, handshakes don't cut it as much as we may want them to. I'd love to be able to trust people, but in matters where money is involved no one can be trusted. I learned this the hard way. Please, use my mistakes to your advantage.
Seconded. It's not a done deal until the money is in your bank account. If someone offers something, you write a Memorandum of Understanding at least to clarify the details.
Also, never trust anyone who asks for a little bit of work at a discounted rate in return for the promise of more work later. Even if they're a government department. They may mean well, but they're almost certainly not in a position to back that promise up.
Re: Ask HN: What was your biggest business mistake?
#8Thinking if you build it they will come. It doesn't. You have to go out and sell, you have to push harder than the other guy, who may be bigger, stronger and cheaper than you. You still have to do it. You have to get rejected and have your skin make a Rhino's hide look sensitive.
When do you know you should keep pushing and when should you pivot/move on to something else?
I always seem to be battling with this question.
Re: Ask HN: What was your biggest business mistake?
#9Trying to run a service-based dev business to support creation of products. That consulting grew to consume 100% of our usable time and resulted in a period of pretty intense burnout, personally.
If you're in this situation, you might try honing your focus - if you can zero in on the most lucrative/time segments of your consulting practice, you may be able to make this work. This does depends greatly on your client mix and financial situation.
We'd almost done that - had a brilliant marketing plan drawn up and everything; then burnout hit myself and my business partner (hard). The coup de grace was delivered by the GFC
(Even here in Australia, small businesses were hit - and all our clients were small businesses or primary industry and simply stopped paying invoices or returning calls.)
Re: Ask HN: What was your biggest business mistake?
#10Thinking if you build it they will come. It doesn't. You have to go out and sell, you have to push harder than the other guy, who may be bigger, stronger and cheaper than you. You still have to do it. You have to get rejected and have your skin make a Rhino's hide look sensitive.
When do you know you should keep pushing and when should you pivot/move on to something else? I always seem to be battling with this question.
On the sales side I don't stop till I'm told we've lost the deal. Even then I still ask for feedback and try to see if there's anything that can be done to recover it, but direct B2B is a bit different to what most people do here.
For other stuff, to be honest I'm just as guilty of holding on too long or overinvesting time in something that won't work at the expense of something that does as much as anyone.
I just try to recognise my mistakes, learn from them, how to spot them happening again and how to avoid/evade them. I think that's all I can really do. I try to suck a little less each day, with varying degrees of success/failure :)