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Alex MacCaw
I'm Alex MacCaw, founder of Clearbit and Reflect, ask me anything. 🔥
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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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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
@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.
Thomas Schranz ⛄️
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?
Alex MacCaw
@__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.
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.
Cristina Bunea
Hey Alex! Two questions from me: 1. Top things you've learned from raising a community round with Reflect? (Congrats!) 2. Saw the recent Whisper integration with Reflect. Super cool. Related to AI, what are your thoughts on Generative AI — is it an investable trend or just a cool tool we'll continue to see integrated into pre-existing products? In some ways it seems to have replaced the crypto hype we've seen in recent years, but do you see hyper-growth start-ups resulting from it? Thanks!
Alex MacCaw
@cristinaibunea 1) I will do a write up of all of this once the round has finished. Too many learnings to put here. 2) It is definitely an investable trend and I wish I knew this last year when I passed on many of the AI copy generating companies, dismissing them as GTP3 wrappers. Today they are some of the fastest growing companies in history. There is huge potential in productizing complex ideas as simple ones.
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
@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.
Manab Boruah
How much time did it take for you to build Clearbit? How many customers does Clearbit has? Did you start with free pricing?
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
@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.
Uladzimir Yankovich
1. What is the average conversion rate on the main page of the Reflect website? 2. Do you sell your Motivation browser extension?
Elizabeth Obee
Clearbit is a genius product. Curious to know how you got growth going in the early stages? And did you rely on Product Hunt at all to drive that awareness?
Alex MacCaw
@liz_obee ProductHunt was definitely a big driver early on. And so was Twitter DMing people.
Elizabeth Obee
@maccaw Awesome, thanks for the insight. Hadn't thought of Twitter DMs. We're live on Product Hunt today with the goal of awareness (https://www.producthunt.com/post...) - hoping it will be a driver for us too!
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?
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!
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.
Simon Rohrbach
Hey Alex! Love what you're building with Reflect. What have you found are some of the main differences in building a VC-backed vs. bootstrapped company, especially when it comes to building product?
Alex MacCaw
@simonrohrbach They are very different types of hard. VC backed is hard because you're moving fast with a lot of expectations and often doing things you don't enjoy (like managing). Bootstrapped is hard because you're moving slow with very limited resources. In my experience it is easier to build a world-class product when you're bootstrapping though because the product is created from one mind (yours). You can always tell when a product has been designed by a committee.
Pauline Rossi
Hi Alex! I would like to start learning developing, coding languages... But I don't know where to start. Would you have any advice for a beginner? What languages would you recommend most? Is it better to start with frontend or backend development? Thank you for taking the time to answer!
Alex MacCaw
@pauline_rossi Yes, learn TypeScript and Next.js. You will be well prepared for the future with those technologies under your belt. And you can use TypeScript on both the frontend and backend. There are lots of free online courses and resources (YouTube).
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.
Angel Gutiérrez Pizarro
Hi! What, do you think about the creative and content economy? Is there something missing there tech-wise?
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
@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.
Karan Soni
What things should I keep in mind while developing a product for my company? Like many things comes to mind while building a product such as the selecting tech stack make it scalable for future also having proper code structure and many different things. And I feel that having these many things in mind is hampering my speed to finish the product So as a developer of a early stage product what would you suggest to keep in mind while I am in process of developing my product? Also what is your favourite tech stack that you would prefer now if you are making a product from scratch? Thank you.
Karan Soni
How do you plan things (Both technical and business aspects) when you are making a new tool and want to launch it in around 2 to 3 months?