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One can very easily check whether one's target customers are averse to dealing with a one-man shop. Ask them to buy your thing. If they don't ask "Are you a one-man shop?", they are not averse to dealing with one-man shops.

A surprising number of enterprise customers are not averse to dealing with one-man shops. It blows my mind at least once a week.

Supposing that a customer does give you the one-man shop objection, you don't say "Oh rats, well, good luck then." You summon your founder gumption and say "Sure thing, I understand that you want to buy this software but have understandable reservations about dealing with a one-man company. What can we do to fix this? Help me understand this a bit more -- is this coming from you? From other stakeholders? Corporate policy? You had a bad experience once?"

After probing for the nature of the objection, you can offer solutions to it.

You might go out of business: I've answered this before. "I've been in business since 2006 and profitable every year since then. Nobody knows what the future holds, but I'm cautiously optimistic. I'd hate to get a real job."

You might get hit by a bus: "I certainly hope I don't get hit by a bus but I'll be extra careful crossing streets, just for you! pause for laughter No, seriously speaking, I totally understand how you guys need business continuity for core services. What if we had a written business continuity plan? Would that help? I can have lawyers and a well-regarded tech firm get one together for us as soon as you get me a LOI."

We need code escrow: "Who is your preferred vendor for code escrow? Great, we'd be happy to work with them. Tabling that issue for a moment, is there anything else you need from me, or can we proceed to the next step?"

You could break stuff: "We carry an industry-standard Errors and Omissions insurance policy in the amount of $1 million. The insurance company was happy to write this policy because we take steps like X, Y, Z to make sure that we don't break stuff. Does $1 million sound adequate?" -> "Great then, we're covered." or "Interesting. Help me understand how you're arriving at your number for how much is at stake here. I'd be happy to quote you for services commensurate with the value you get out of our system, and we'll only move forward if I can get our insurance underwriter to approve that level of coverage."



I am a one-man shop and sell software in the enterprise space. I also have competitors and while I see my product as very different, a lot of my work goes into educating my market about why.

Most of my customers are household names and they're not averse to dealing with my one-man shop. It doesn't even come up. Their staff wants my software and they work their process to buy it. That's it.

I have not had to answer any of these objections (thankfully). I'd probably pass on the customer if they came up.




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