Alex MacCaw

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

Hey, I'm Alex and I like writing English and TypeScript. I have founded a few companies (most recently Clearbit and Reflect), was an early engineer at Stripe, and I've also written a few O'Reilly books. I'll be answering questions on November 9th 🔥
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Catherine Norris
What have you found to be your most successful growth channel?
Alex MacCaw
@catherine_norris Email and Twitter
Radz M
What’s your take on Grafana? Who are some of the best sales reps you’ve ever worked with?
Murali Gottumukkala
@radz_m I am intrested in hearing this answer
Alex MacCaw
@radz_m Grafana is a gold mine :) Hmm, best sales reps - I've worked with a lot of them. But Cliff Marg comes to mind.
Jared Lambert
when did you know you had product market fit, and how long did it take you to get there?
Alex MacCaw
@jared_lambert1 With both businesses I immediately felt product market fit. It's hard to define but you know it when you know it.
Vedran Rasic
When you reflect on Clearbit... what are the three things/events that helped you go from 0 to 1M ARR, and what are the three things/events that moved the needle from 1M to 10M ARR? Thx a lot! Rooting for Reflect!
Alex MacCaw
@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
At what point did you throw in the towel and realize that strict typing was the way to go? And who told you so in 2011?
Alex MacCaw
@sasha_mackinnon You were so right about this.
Altryne
Hey Alex, been following you for a long time, since Spine days! Incredible to have seen your journey, via books, working at Twitter (am I remembering this correctly) and then Stripe, Clearbit, and now Reflect (of which I'm a dedicated user, it's incredible) Could you reflect (sorry for the pun) on some tough times? Times when folks didn't believe in you / what you're doing? Would love to hear about them and how you managed/figured out a way forward.
Alex MacCaw
@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.
Chirayu Patel
Thanks to great infra (cloud, open source, copilot) small teams can easily build and ship software. This has increased competition with most niches occupied by multiple products. The challenge, it seems, is not product, but GTM and managing third party integrations. How will these trends of decreasing build complexity and increasing competition impact B2B SaaS?
Alex MacCaw
@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.
Stefan Pettersson
After exiting Clearbit, what emotional phases did you go through and how long did it take you to settle with what you are doing now? Do you set different boundaries/prioritization with current ventures compared to pre-exit? (e.g. not compromising on life quality vs grinding, etc)
Alex MacCaw
@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.
Philip Snyder
Clearbit is very interesting. Can you dive into specifics about how the IP-DeAnonymization works? I understand how big orgs have their own IP ranges but you guys claim to be able to detect even smaller companies? Would love to hear about the process.
Alex MacCaw
@philipsnyder This is our secret sauce :)
Philip Snyder
@maccaw Great answer! After learning about Clearbit I started researching ASNs and the Arin Database. Interesting stuff.
MaheshVarma Kanumuri
Hi Alex, It's nice to interact with a person like you. What is your favourite book (Written by you) ? and Why?