The Story Behind My Investment In Ironclad

Sometimes, picking a company to invest in is just easy. The hard part is getting in.

About two years ago now, I met Jason Boehmig of Ironclad during YC’s Summer 2015 batch (before Demo Day). One of my founders who was in YC singled out Jason as outstanding. Jason’s pitch was exactly what I love to hear, paraphrased: “I was an attorney (at a prestigious Valley fund). I taught myself to code. I quit my job. I founded this company to bring systems intelligence to the legal department of enterprise companies and beyond.”

I had to pitch Jason to let me in and also to make a gracious consideration for me.

I started to help Jason with his round immediately and got working some customers. Jason put me to work right up front but he was easy to work with. In fact, I would say he’s one of the most organized founders I’ve seen — his emails are clear, instructive, and written as if a lawyer, programmer, and BD rock star were mashed into one person. At the time when he was raising, I was just starting my current Haystack Fund #3, and my wife was nearly 9-months pregnant – with twins. I needed to close my fund, tend to my family, and wire money I didn’t have. I explained the situation to Jason over email. Like a true gentleman, he listened and made the accommodation for me. It was a small gesture and not much money at the end of the day, but in the moment, it was stressful for me and Jason assured me it was all good.

It’s those kind of interactions which keep my interest focused on being an early┬áinvestor and building early relationships with founders. In the months and years that followed, Jason would skillfully pump my network for customers. He sent the best email updates every month, and absorbed tough feedback like a pro. He always wants to get better and to learn, and that ethos is embodied in the Ironclad product and the Ironclad founders and team. And, it is that ethos and relentless drive which attracted the former head of Salesforce’s AI efforts, Steve Loughlin, to lead the company’s Series A from his new role at Accel Partners.

Jason’s true colors showed again during the Series A process. I had a front row seat. No surprise, Jason and team referenced incredibly well. He handled each interaction like a professional and I am sure he’s already on the Series B radar of other firms. I was fortunate to get to invest again in the A, and I know Jason will be calling on me for even more introductions. And, customers will be lining up. The legal department of enterprise companies remain one of the last open space in SaaS, and the Ironclad team will now barrel ahead with even more ammunition.

Haystack is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2017 Semil Shah.

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