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

Alex MacCaw
114 replies
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 🔥

Replies

Joshua Dance
Summer Bod 2020
What is your favorite app currently?
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@joshdance Visual Studio Code and GitHub CoPilot
Thomas Schranz ⛄️
Rakun Sensory Sanctuary Quiz
Rakun Sensory Sanctuary Quiz
Big fan of your writing on software (Spine!) and thoughts on entrepreneurship. What do you think of executing multiple ("smaller") bets (Pieter Levels, Daniel Vassallo) vs focus on one bigger bet?
Thomas Schranz ⛄️
Rakun Sensory Sanctuary Quiz
Rakun Sensory Sanctuary Quiz
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@__tosh I have mixed feelings on this. There is a similar question around how do you know when to pivot or not. It is hard to know to be honest. I know examples of people who pivoted five times and on the fifth time built a massive business. I also know people who stuck with the same idea idea for years, and only in the fifth year of business did it take off. I guess it depends on the problem you're trying to solve. With Reflect, for instance, it is an extremely hard problem - it requires many years of work to even begin solving.
Vinh
What exactly method you yourself(not your marketing/PR team) use to marketing your own products?
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Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@kureikain I pretty much just use my Twitter account and a newsletter. I have ~30k followers on Twitter, and 20k emails in Reflect's database (using customer.io). Our strategy is very basic - we just launch and launch and launch, blasting those channels each time. The truth is, I'm not that good at marketing yet. This is one of my main areas of improvement for next year. Reflect's product is too cheap to make it profitable to gain customers by advertising, so we need to come up with other ideas.
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Evgeny Kotelevskiy
@kureikain @maccaw How do you feel about Twitter these days? Do you think it still remains the top social network among founders/tech people? Have you ever considered switching from Twitter to LinkedIn or may be even Threads?
@maccaw Love the honesty!
Altryne
Extensionizr
Extensionizr
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
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@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.
James Adam
You've implied (e.g. https://twitter.com/maccaw/statu...) that the specific license terms a developer might make their code available under (e.g. non-MIT licenses) should not restrict the use of that code (e.g. in ML/AI applications like Co-Pilot). Is that accurate? If so, do you believe that non-MIT open-source licenses are worthless? Should an open-source developer have _any_ power to control use of the code they create? And following the second tweet in that thread (https://twitter.com/maccaw/statu...), would you say that it's therefore a moral imperative that _all_ software be open source (including all software in all private companies), since _any_ of it may contribute to ML/AI projects that accelerate The Singularity?
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@lazyatom Yes, I believe training open source code with ML is fair use, and I expect when it's tested (with the GitHub CoPilot case) that the courts will agree with that. Fair-use has long been enshrined under copyright law. I believe an AI consuming source code is equivalent to a human reading it. It comes back to the same arguments as in the Google vs Oracle case [1] I am a singularity maximalist in that I think we have a morale imperative to bring it about as quickly as possible. I would be quite happy if Reflect's source code (private as it is) is used to train CoPilot. [1] - https://en.wikipedia.org/wiki/Go....
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
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@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.
Vedran Rasic
LeadDelta professional relationships CRM
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
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@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.
Anand Sharma
Is it true you still use monospaced fonts to write typescript?
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
moe3615
Huge fan of yours since I saw you on a podcast. You're an inspiration and I've been following and reading your stuff for years. My ama, is a bit more personal. With your incredible success how do you remain so humble? Even when stepping down from Clearbit you take the extra step of giving the new ceo credit of being far more qualified than you. I've seen this same behavior so many times from you and always wanted to ask you. You're an inspiration to tons of silent readers and followers.
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@moe3615 You are very kind! And to anyone reading the above comment, I swear I didn't write it with my alt 😂 To your question: I think, when you've been wrong as much as me, it gives you a degree of humility. We're all pretending we have all the answers, but in reality nobody really knows what's going on.
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Max Stoiber
With the benefit of hindsight, how does it feel to have stepped away from Clearbit after 7 years? Would you make the same decision again? Also, what have you learned about "only" being on the board compared to being an operator and a board member?
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@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.
Ryan Morrison
Hey Alex, it's great to hear about your accomplishments in the tech industry! As someone who is also interested in digital entrepreneurship I'm curious to know what inspired you to start your own companies? Was it a desire for more creative control or a specific problem you wanted to solve? Looking forward to hearing your thoughts on November 9th!
Uladzimir Yankovich
Manganum sidebar for Google Chrome
Manganum sidebar for Google Chrome
1. What is the average conversion rate on the main page of the Reflect website? 2. Do you sell your Motivation browser extension?
Alexander Nevedovsky
After an exodus from the venture-backed startup, what motivates you to keep pushing (with Reflect or not)? What are you driven by?
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@alexander_nevedovsky I believe all humans have to feel creativity in their lives to be happy. Different people feel this feeling in different ways. Some people by writing books, some by acting in musicals, some by managing large teams. I feel it by writing code. At Reflect I write code every-day and I feel happy.
Julie John
What advice you have for a subscription management software platform like SubscriptionFlow?
Bruno Belcastro Pinto
What are some learnings from clearbit that you can share with other product crafting folks? (Anything ranging from Product, Strategy, Eng, Operations, Design,Marketing, etc.)
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@bruno_belcastro_pinto That is a question with lots of answers. I'd going to cheat and point you to the resources I've written - they contain a lot of my learnings: - https://themanagershandbook.com/ - https://www.amazon.com/Great-CEO... - https://open.spotify.com/show/71...
Ayan Dutta
I’ve used clear it extensively, as a sales person. So many companies exist in Clearbits domain (Apollo, 6sense, zoominfo etc). Will data (techo firmographic) still be a moat? What’s the next evolution in sales tech to find quality accounts/leads? Anything that excites you?
Harris Cheng
Hey Alex, thanks for hosting an AMA here. I've got an issue about target audience searching that I'd love to get your feedback. If you're not 100% about the exact target audience despite interviewing a large bunch of them, would you rather: (a) spend more time in researching the right target audience OR (b) open your service to 3 or more user types OR (c) develop on the one whichever gives slightly more confidence first and change it when there is more conviction on other types What makes you convinced about it? Thanks!
Jared Lambert
when did you know you had product market fit, and how long did it take you to get there?
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@jared_lambert1 With both businesses I immediately felt product market fit. It's hard to define but you know it when you know it.
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
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@sasha_mackinnon You were so right about this.
Ryan Hoover
Alex! I've been following Reflect since before your public launch and appreciate the non-VC, community-driven approach to your recent round of funding. Curious to learn more about why you took that approach and any learnings for those considering doing something similar.
Linus Ekenstam
@rrhoover I would also really want to know the answer to this question 🫶
Alex MacCaw
Reflect New Tab for Chrome
Reflect New Tab for Chrome
@rrhoover Hey Ryan 👋. The reason I decided to crowd-fund over taking traditional venture capital is to do with incentives. Reflect's goal is not to be bought or IPO. But venture's incentives are all aligned with these outcomes. A community round, where you set the slow-growth expectation upfront, has much better aligned incentives. We even went a step further and aim to pay our investors a dividend. Now we have perfectly aligned incentives and expectations with our investors.