Doubt

Contactually is currently in the, to quote Jason Lemkin, the Possible, but Painful phase. We’ve long since passed the initial $1M ARR phase, where we became “real.” We’ve nailed enterprise customers. We know how to hire. We have a clear idea of our product roadmap, vision, and strategy. But we’re in the long, slow slog to $10M ARR, where every month is focused not on figuring things out, but making sure we grow the right amount to get out of this phase as soon as possible towards inevitability.

At the end of last year when we not just doubled but tripled our revenue, a new member joined our team: Obvious. It’s Obvious to our team that we built something great. It’s Obvious to our team that we have a Grand Vision. It’s Obvious that what we have works. It’s Obvious to our team that when they get on the phone with a lead, they’re delivering something valuable with clear ROI.

But there has been someone hanging out in the back of our collective minds, that, unless we keep him leashed up in the back of the office, will destroy all of us.

Hello, Doubt.

Doubt looks at what you’re doing, and says we’ll never do any better.

Doubt says we’ll never raise another round of capital.

Doubt says KPIs will never improve.

Doubt says our customers will never be happy and will start leaving us.

Doubt knows that we’ll never be able to solve our systems issues.

Doubt tells your employees to quit or to not work so hard.

Doubt convinces people to point out problems, not solutions.

Doubt whispers into your VP’s ear that it’s not going to get better.

Doubt is talking to your investors and advisors, too.

Doubt says you don’t have enough money in the bank.

Doubt was there the whole time. But early on, Doubt is fine, because Failure is expected.

Doubt will sometimes take an afternoon off, torturing someone else. But you can be sitting in a meeting, pitch, or inbox, and Doubt will walk right in.

“What are you doing?”
“Building a company.”
“It’ll never work.”

I’ve learned that Doubt is one of the hardest things you have to face.