Stop looking for magic bullets

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Every founder has obsessed about something.

For me it was a guy named Will.

Will had been VP Sales at a direct competitor that went public. He built the Europe business from $0 to $50mm in ARR and was part of the leadership team when the company went public. He reached out one day because he heard about us. I showed him a demo. He thought we had the Best Thing Ever. Immediately he wanted to sell it.

There's nothing as validating as hearing someone deeply experienced in your market get excited about your product.

After a couple of months of getting to know each other, we hired him. It was a huge step to us as founders–particularly to my cofounder. We had a bona fide VP Sales who was going to get us to millions in ARR–and quickly. It felt like an inflection point–we were about to achieve escape velocity. We had funding for it–but it was a stretch, and more than we were planning to spend on sales at the time.

I'll skip to the end: six months after starting, he had only closed one deal–that I had gotten to the 1 yard line. We had flown all over the world, spending 10x more on T&E than before, meeting with several totally unqualified (but great-sounding) prospects who had no intention of buying. It clearly wasn't working.

Frustrated with the lack of success, when a pilot that seemed to have gone well didn't convert he was incredulous. He threatened to take their data and sell our solution to a direct competitor if they were "too stupid" to buy. That was (obviously) the end of things. I forgave him–the botched pilot wasn't only his fault. But we all felt the pain, no one more so than me. Even after we parted ways, we never got that customer back. Some damage is permanent.

How magic bullets kill companies

Whether it's a key hire, a shiny new agency, a partnership, or a top-tier VC, founders obsess. They buy into the marketing, the branding, the reputation. It's hardwired into being human. But these rarely work out the way founders hope.

In reality, hiring the wrong person can be very damaging. But hiring the right person is just one step on the path. It's not a magic bullet.

Thinking you have the magic bullet can kill companies. One company I worked with hired a CRO, thinking this would solve all of their sales problems. That CRO turned out to be terrible. Good people left, the sales team he hired (for ~$1mm/ year) never sold a single dollar of software; renewals ground to a halt as he broke the part of the sales motion that was working, while what he started never worked. And in the background he spent $500k on a botched migration from Salesforce to Hubspot.

Recently a founder explained why they chose a Tier 1 VC–because of their ability to help with recruiting. After the investment closed, he reached out to their recruiting partner–to learn they had a 9 month backlog.

Another company took a seed investment from Sequoia Capital, the most famous VC firm. They promised the data the startup needed to prove their algorithm worked. Their portfolio companies would happily share it if they asked, just sign the Series A term sheet and LFG.