In my case, it heavily stemmed from our inability to do sales (at all). We had feedback early about how this was an $XXXXX product (and we were in sales process for that) and it put blinders on us. We should've been okay with $XXX and grabbed 5-10 customers early.
Why we couldn't do sales is something I'm not going to put on the internet because it affects people other than me. (I have no issue talking about my shortcomings.)
I left that company and started another with a proven sales/marketing type within 2 months. The story is much different than my first. It's because he can sell.
Funny enough, I have a license to use my old product w/o selling it, so we do. We've gotten at least 10 customers asking to buy it. And they're fairly emphatic about it.
I can appreciate that but I am wondering if you can share what you think are core skills, habits, or personality traits that are critical in order to make sales happen for a new business/product.
* Don't be afraid to ask for the sale
* Be comfortable "closed lost"-ing a deal instead of having non-productive conversations (SOGOTP)
* Recap all meetings with prospects or customers (email sent to them with information such as about your product, your call with them, their painpoints, next steps, etc.)
* Leave meetings with a tangible next step. Someone not wanting to schedule another meeting is a huge red flag
* You don't need a sales process or methodology, but you might if you're not able to effectively manage your deals.
* Be comfortable living in the present and future, as you want early prospects to help shape the future with you.It really depends on the product/market. I've worked in a startup with a competent founder who was great at sales, and which nevertheless, after 2 years, went bankrupt without making a single sale. Our product was targeting enterprises in a specific niche - there were perhaps 10-20 or so potential customers worldwide. Making even a single sale would've been huge.
Maybe it's a difference between bootstrapped mindset and VC-fueled one.
I think a lot of it is due to the VC playbook. The question of "who am I building my business for?" looks a lot different between VC and bootstrap. Once you start getting into heavy hitter revenue (grain of salt, I've never done this as a founder), the machine starts working largely on its own. It's probably more impactful to spend time on the business systems instead of the product.
But bootstrapped founders seem more likely to stay close to the product for longer. Eventually they may want some sort of out, and you see the playbook execute much much quicker.
Now, I have other theories on why it doesn't play out well. Going from 10M -> 50M ARR is a huge hurdle. You have to really level up a lot of the business itself to do so. It might be that it's just not possible for a lot of companies to bridge the gap. I think it's easier to go 50M -> 100M than 10M -> 50M.
The bootstrap mindset understands that "idea man" isn't an actual job.
Marketing / Sales can be a blocker too.