How I pivoted my startup

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Jon: What traction were you looking to achieve once you relaunched the category

you were focused on?

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Raad: We didn’t set a high ambition in terms of the revenue we wanted to hit.

At the time, we just needed to survive. We’d make more money than vending

right now which is predominantly on the payroll for a couple of guys.

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I read all the Superhuman stuff after we ended up doing this pivot and it really

doesn’t make sense. You’re uncertain, and I get it from a founder’s perspective

now, looking back, of who we should go after. You go after everybody. We just

have to blanket every single person because you’re anxious, you don’t really know

who the right person is. You think that they’re too small of a segment. Just how

many general counsels really are there?

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There’s always that anxiety of when you zoom in on your customer segment, is

there a big enough market? I think it just comes from intuition. It comes from data.

You have to talk to your customers. It’s something YC always drills down.

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After we went through this whole experience, I would read and watch all the YC

advice. At the time they didn’t really make much sense. I thought I really took it to

heart. It's only when you really fuck up, royally, that you then turn back to the basics.

You understand what they meant by talking to customers, being ramen profitable,

or not doing things at scale.

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We restarted the product with a spreadsheet and it was such a humbling process.

You get lost in what you think just because you raise a seed round from top-tier VCs,

and you think that you’ve figured it out. I'd say, arguably, that’s the easy part.

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Fundraising is still hard. Clearly, it was for us because of the drama that went down.

Ultimately, it really just is finding that core base of customers and going heads down

and building to solve something for them. You’re constantly tinkering between how

much do I do manually versus how much do I quote out and automate. We’re still at

that phase today.

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