#46 — Blank Canvas Moment

On Tuesday, I left my job at Drift.

The backstory:

  • In 2016, I joined Siftrock as co-founder & CEO.

  • With $0 in funding, we build a nice cash positive business (>$1m ARR, 150+ customers, growing 100%+ y/y). I was most proud of the customer love and great team.

  • Drift acquired Siftrock in August 2018.

  • During 3 years at Drift, I had a range of roles from GM to strategy to product marketing and product leadership. It was exciting and often humbling. The Drift CEO David Cancel is a positioning & category creation master, the leadership team was impressive in many dimensions, and the company grew to a scale I hadn’t seen before. I learned a ton.

So now…

I’ve got a blank canvas.

I hope to co-found another SaaS company in the not-too-distant future. I don't know exactly what/how/when. I’m exceptionally lucky because I’m not in a rush.

Biggest challenge so far…

Resisting the urge to solve for ambiguity.

There is a voice in my head yelling “so… what’s the plan?!?" 😬😬😬

Logically I know that there is a lot to be gained from widening my aperture before narrowing down. I know that solving for ambiguity is the wrong thing. It takes time to build conviction. And it’s a futile effort to try and game out all the angles.

But it takes some reminding. 🤷‍♂️

How do you get comfortable with ambiguity?


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