pre-financing thoughts

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“Back me or back the fuck off.” – Dolly Parton, Drunk History
I’ve been reading recently about the significant contraction in financing available for new startups, and I completely and utterly believe it’s true. This isn’t a story about how I don’t believe the hype. I’ve spoken with a few investors over the past six weeks or so about what I’m working on with Cathy Labs, and several of my questions for them have been gathering information so I can decide how I want to structure the company finances. Do I want to raise a small convertible round? A priced round? How much money do I want to get started? How much am I willing to give up in the company in exchange for that investment? All the important questions that I need to work through before I start talking in earnest about money with possible investors.

But then I read things like this amazing post from Mark Suster today, and I wonder to myself (and now aloud, here, to whoever may read this at some point): “Why am I not more afraid? If capital is drying up… if it’s getting harder and harder to raise money… Why am I not more intimidated by the process of raising money and the future fundraising cycles that will come as Cathy Labs progresses?”

And truly, I have no simple answer as to why I am not completely freaked out about that. I suppose some of it comes from having been through this a bit once before, but I would expect that would make me more freaked out, more worried about the seriousness of all of this. I remember how stresssful it was to realize that the ability of my colleagues’s families to pay their mortgages was in no small part relying on me to make good decisions and come through with good plans. That part was stressful, especially when we hit the “fatal pinch” and I knew that things were getting too close to the edge to feel safe. It was so stressful my hair thinned, I couldn’t eat, I was a wreck… and yet I’m not afraid of facing it down again. Even with the deck stacked more against me re: ability to raise and the climate tolerating fewer and less risky investments.

Maybe this comes down to a few things:

  • I love this problem space. I know that this is what I want to work on for the next ten years. I’m not building Cathy Labs to flip it for an acquisition; I’m building it to make a great company that works well and solves important problems.
  • I’m worth taking a chance on as a founder. I was super stressed during the fundraising and acquisition stages of MailRank, but looking back… damn, the team did a great job during that time and I was key to making that happen. I was key to holding us together, key to the acquisition closing… I followed what I thought was right and looking back, I was right. It is good to have that to look back on and say, “Okay, this will be a new company with new situations and new problems to solve – but you’ve already proven that you can make amazing, hard decisions when the situation calls for it.” It’s nice to have that past success to look back on.
  • I’m worth taking a chance on as a leader. A big part of the success of Cathy Labs will be attracting and retaining the team that will build the product and make it amazing. I’ve had lots of experiences working with hundreds of great people in the past decade-ish, and I know that I can count on my network of former colleagues to help me build a team (maybe including a few of them!).
  • And finally… I’m just stubborn. When I put my mind to something, it’s very rare for me to back away from the challenge of making it happen. This is how I managed to pull through some of the most arduous, long-term, coordination/collaboration-heavy projects in my time at Facebook. One guy told me, “This has been tried before, and you’ll never pull it off.” Wrong answer, dude. Now that I’m reading articles about all of the ways that the fundraising climate will lead to longer cycles, fewer offers, less FOMO (so less excitement on a “hot company” on the parts of the investors), lower raises… all that shit just makes me more determined. More fired up.
  • I know that starting a new company is an incredibly risky decision. I know that it’s very likely that any new company will fail. I know that this is why there is risk associated with investment, that most investments lose their money, that most of the returns in VC funds come from the few successful investments in a portfolio. And yet… I’m just completely determined to bring Cathy Labs to life.

Funny how all that other shit gets de-prioritized when you’re sufficiently fired up and ready to make something amazing happen.

articles that have made me think more about this: