I'm Alex MacCaw, founder of Clearbit and Reflect, ask me anything. 🔥

@mxstbr I would absolutely make the decision again. Indeed, I would leave even earlier, maybe at around 30 employees, and set the expectation with the team upfront. I have learnt what I love which is a day of coding without meetings. So I should just stick with that. r.e. the board - I can tell you the hardest thing about not being an operator in the company is that you feel quite impotent. You can provide advice (as best you can), and feedback, but ultimately it is the CEOs job to make the decisions.

@catherine_norris Email and Twitter

@jared_lambert1 With both businesses I immediately felt product market fit. It's hard to define but you know it when you know it.

@vedranrasic Going from 0 to 1 M ARR was a combination of us: a) increasing our pricing and b) creating a Salesforce integration and c) hustling. Going from 1 to 10 was quite straightforward after we hired a sales team.

@sasha_mackinnon You were so right about this.

@altryne The hardest times were, in order: 1) Performing a layoff of 20% of Clearbit during COVID 2) Getting my first Green Card application denied and being forced out the US 3) Clearbit getting a frivolous lawsuit 4) Coming to the conclusion that I should no longer be CEO of Clearbit 5) Getting a notice from the city of San Francisco that our office wasn't zone correctly and we needed to vacate (I loved that office) Along the way there's been folks that believed in me, and folks that haven't. I've always had a quiet inner confidence that propelled me regardless. In general, most of the problems above resolved themselves with time. Here's a good mental model when it comes to problems: will I still be worried about this a year from now. If so, it's probably important and worth worrying about. If not, resolve it and move on.

@chirayupatel That is true, but there are seven billion people to sell to. Well, not all of them, but you get my point. It's possible to make a lifestyle biz in many many areas. GTM is definitely the hardest part for me personally. It should all be programmatic and automated. Which is why I love advertising - it's the most efficient way of scaling a business. Unfortunately, due to Apple's policies, it has recently become less efficient.

@stpe After I left I did a lot of writing. About my experience, my learnings, and what I wanted out of life. It was very cathartic. I also did a lot of therapy. I jumped into Reflect quite quickly because it was smack bang in the venn diagram of things I wanted to do. I wanted to build a tool I used every day, that was UI heavy (I love designing), an Electron app, and something around writing. Sometimes I worry about being ambitious enough. But then I think about the leverage in improving people's thinking through note-taking. That is enough for me.

@philipsnyder This is our secret sauce :)

@maccaw Great answer! After learning about Clearbit I started researching ASNs and the Arin Database. Interesting stuff.