I can't give details over why I learned these lessons without dox'ing myself, even speaking in broadstrokes is hard and the actors are litigious.
- Don't make your product hard to buy.
- Don't take investments from a potential customer.
Long story short, the key innovation was fiscal (looking to draw revenue from the real meat of the industry and not where it was traditionally placed in the supply chain), the tech was compelling enough to get investment from a large player, we built the product, then tried to sell the product to the investor, they dragged their feet, and eventually offered to buy the company instead of license the technology. But only after we ran out of runway and everyone lost their jobs.
The founder said "no" and the company is gone.
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When I say "don't make it hard to buy," in B2B sales think about how much money you want to make off a single customer, given that number, what level of the organization is there someone that has that purchasing power, how hard is it to get them in a room, and can you walk out with a sales contract finalized or do they need to kick it back to their team for a final approval. And if that timeline exceeds your runway and you need the sale to close you're fucked.
In less crass terms, as an early stage startup you want your enterprise sales to scale horizontally through an organization. If your ideal user is at that company, you can only make so much money by selling it to them, because they have a limited budget. So you can instead sell to their manager, by getting the user to convince them to get more money to buy your product. But if you get greedy and then try to sell to that manager's manager, all of the sudden your advocate is two levels removed from the person making the decision and that's much more difficult to close. What you want is lots of deals closed fast, and that manager to tell another manager at the same level their team is using your product, or people to talk about you at the water cooler and get their managers to buy.
And once you scale up, then you can offer discounts for expanding to all teams under an org instead of each team buying individually, and now you have an enterprise contract that's a signal to get another enterprise contract with a competitor.