How to make leadership decisions based on gut-feeling

There comes a time when a company faces big issues that really reflect the way they want to speak to their audience. For example, are you a company that says, “Hey, guys,” or should ‘guys’ be considered a sexist term and that’s the company stance.

How does the team know? It might be in a style guide somewhere but it’s not used. That’s the problem today’s guest recognized and she created a company to solve it.

May Habib is the co-founder of Qordoba, an AI that helps everyone at a company write with the same style, terminology, and brand voice.

May Habib

May Habib


May Habib is the co-founder of Qordoba, an AI that helps everyone at a company write with the same style, terminology, and brand voice.


Full Interview Transcript

Andrew: Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of Mixergy, where I interview entrepreneurs about how they build their businesses for an audience of entrepreneurs. I have to tell you, when I research guests, one of the things that I try to look for is the way that they write their company name. May, you might have noticed this, like, is HostGator, for example, one word or two words? Is it uppercase H and lowercase G for Gator, or is it uppercase H, uppercase G? Like, all that stuff. And if I’m writing to a founder to invite them to do an interview with me, I want to get that right because that stuff matters.

The thing that I noticed though, is they don’t get it right. I go to their website and the logo has it one way, then you go to their privacy policy and it has it a different way, then you go to their blog and it has it a different way. And no exaggeration, within two different blog posts, I could see it written two different ways. Now, the way that it’s written is often in a style guide somewhere, but nobody goes to check a style guide. And we’re talking about, like . . . even if it’s a two-page Google doc, people aren’t going there. Sometimes style guides go on for pages, and pages, and pages and nobody checks for it.

Now, this is one little issue. How about bigger issues that really reflect the way that you want to speak to your audience? Like, are you a company that says, “Hey, guys,” or is guys considered in your company a sexist term and maybe you’ve gone on the record saying, “Guys is a sexist term. We’re going to use y’all,” or are you a company that never uses y’all because y’all is not proper language for your audience? Who knows? It might be in a style guide somewhere but it’s not used. Anyway, that’s the problem.

May Habib created a company to solve that. She says people aren’t . . . first of all, companies don’t write style guides. We’re going to make it easier for them to write those style guides. Number two, people don’t, within a company, go and use the style guide. It’s too clunky. It’s too much work. This one, right? What if we create software that automatically creates a style guide for companies but more importantly automatically checks everybody’s writing against the style guide so that everybody, the legal team, the person writing an email if you want to use it, the person writing the blog post, even a brand new person who starts off can write the way that you as a company want to communicate. That’s what she did, eventually. She started off doing something else. The company that she created is called Qordoba. It builds software that helps companies write content.

And when I say eventually, I mean, it’s because she had a different idea. She was doing well with that idea, and then she gave up serious revenue because she said, “No. No. We have to switch.” And I’m curious about how she came up with this idea, how she came up with the previous idea, and what made her . . . even though she finally had revenue, even though she finally had customers, what made her say, “No. We’re not going to do it. We’re going to give up this revenue. We’re going to give up these customers. We’re going to give up this new thing that we created that people like.”

All right, and we’re going to do it all thanks to two phenomenal sponsors. The first is HostGator for hosting websites. The second is Toptal for hiring developers. And I should say that, May, I discovered you because someone on your team bought ads from us months and months ago, and I said, “Wait, I want to get to know the company. This seems like a really impressive company.” And so we set up this interview, and I’m glad that you’re here. Thanks for being here.

May: Thank you so much. Thanks for having me, Andrew.

Andrew: What’s the revenue right now?

May: So we are approaching a mil in ARR, and we did that in about six months, which is the fastest I’ve gotten to a mil. It took us about 18 months in the previous business to get there, and we are going to do that much in a quarter. So it’s accelerating really quickly, which is fantastic for validating the really tough kind of end of 2018, early 2019 that we had where we were doing a lot of very interest soul-searching based on the market data that was coming back to us.

Andrew: Can you repeat that? How much money did you make before you decided, “No, we’re giving this whole thing up and starting again”?

May: We are at almost $4 million ARR.

Andrew: Four million dollars, and you gave up all of it?

May: We are turning that, and I’ve given up most of it. Yes.

Andrew: Before this, you were working at Lehman Brothers. Can you give me an example of what you did there?

May: I started my career as an investment banking analyst. My big dream was to go and be a professor, and I had applied to a bunch of Ph.D. programs. And then I didn’t have any money to pay for it, so I was counting on a scholarship, and I was a Rhodes finalist and didn’t get it and kind of sick of the whole process and really last minute actually took this job at Lehman Brothers and loved it. I really loved it. I met . . .

Andrew: What were you doing there?

May: I was an investment banking analyst and M&A for technology.

Andrew: Analyzing what . . .

May: In New York.

Andrew: . . . tech companies? In New York analyzing tech companies for?

May: I mean for S1s, for big debt raises, helping take companies public.

Andrew: Got it.

May: So Verifone was kind of a big client that I worked on, helped them do a big equity raise after they had gone public and confidentially looked at . . . well, no editing here so I won’t tell you anything that we did that was confidential, but looked at some pretty interesting, very strategic M&A deals on behalf of our clients, you know, stuff in the kind of billions of dollar range in the financial services.

Andrew: You told our producer, at one point you’re wiring how much money to shareholders in Singapore?

May: That was the next job. So I went from Lehman Brothers to Barclays. So I was there through the financial crisis. And then one of our clients throughout this whole ordeal was the sovereign wealth fund of Abu Dhabi. So I speak Arabic, I’m Lebanese, I was also the top-ranked analyst in my group, and the fund needed somebody. And so I packed up and moved to Abu Dhabi also on a whim. I do a lot of things on whims, Andrew, start companies, leave jobs, leave the country, but it ended up being an incredible opportunity. And, yeah, one of the kind of crazy things I did was help the team buy a company in Singapore, and I ended up being the person actually in charge of wiring the money and the instructions to wire the money from, like, our treasury to their treasury.

Andrew: How much money are we talking about?

May: It was $4 billion in local currency.

Andrew: Billion. Wowee. You say on a whim, but you’re an analytical person. I’m kind of curious about how entrepreneurs make decisions that seem quick and haphazard but in reality, there’s gut instinct informed by analysis, by experienced analysis. How do you do that?

May: So I have to make sure to be very conscious of the fact . . . and it’s a fact, I do believe this, that my gut is more powerful than my intellect. And accessing, you can call it gut, you can call it voice, you can call it intuition, having the kind of mind-gut connection as an entrepreneur, having that pathway clean, being able to hear yourself think is just the most powerful tool and . . .

Andrew: Give me an example of something? Is it too much putting you on the spot to say do you remember a time when you made a decision on gut instinct but it was informed?

May: I mean, your whole mental model is informed by everything that you take in, and your gut is able to help you make decisions based on that information that you may not even be able to consciously process. And so the way that the gut tells you what to do is by making you feel bad when it’s not the right thing to do and, you know, paying attention to when you feel anxiety, where you feel it in your body. I’ve read so much about kind of just the somatic understanding of what’s happening to you and just being able to place emotions in your body and being conscious and in tune with that can really help you make better decisions, or understand where you’re not making decisions where you should be.

Andrew: So the first version of Qordoba was about localization. You’ve got an example of where you saw the importance of that? Was that at Lehman Brothers?

May: So I was in my Dubai-based gig, traveling the world and seeing Asia specifically, but also Europe and doing stuff in California then as well and was based in the Middle East, and, you know, this was 2010, 2011, 2012, and everyone was using different types of apps daily. I mean, at that point, WhatsApp hadn’t really kind of taken over everywhere, and, you know, the kind of the famous chatting apps in in Asia. And I just felt like it was too hard for both content and software to be in other languages once I, you know, started talking to people about why things weren’t in other languages, why it was . . .

Andrew: Because you were talking to software developers and . . . No?

May: I was just talking to individuals who were at companies?

Andrew: And their apps weren’t working well? They were at companies, and then what’s the problem that they had?

May: So it was hard to take a product that was in Chinese and get it to be in English well.

Andrew: For their companies, like when they were going into the office, it was hard for them to take their product and move it to a different country?

May: Yeah. Software localization is kind of a thorny problem.

Andrew: Why is that such a hard problem? Wasn’t there a period there when Facebook said, “We’re going to allow all of our users to translate our site to whatever language they want. If you’re interested in participating, hit this link and translate . . . ?” If a bunch of strangers who don’t know Facebook that well can go in and translate it, why is it such a hard problem for app makers?

May: You know, kind of crowd-based localization was a fad, and it’s been largely abandoned, just about nobody does it anymore. There are some real interesting peculiarities of that market, but what I concluded was it was going to be hard to build a multi-hundred million revenue pure play software product in that industry without a really large services arm. And so our first kind of micro . . .

Andrew: Before we get into that, I want to understand the problem that the software makers, the people who are working in software companies had, why wasn’t it as easy as saying, “All right, if crowdsourcing . . . ” I think for a lot of things we imagine at a period there that crowdsourcing was going to solve everything. I know podcasters used to say, “Here’s an empty box, just everyone writes one sentence from the interview, we’ll end up with the transcript . . . ” it never worked ever.

May: It never works. Yeah.

Andrew: What I discovered was behind the scenes, the people who made it work paid for translation services. They put it on the site, and then they let people edit it to improve it, and even that we had to all get rid of because people were just writing random stuff in there and promoting stuff. So couldn’t these companies just hire a translator? How much does a translator even cost? If they’re writing software, couldn’t they pay to hire a translator?

May: So the services piece, it’s about the continuity. A one-time, one and done thing is really not that difficult, but integrating continuous localization into a continuous software product, you get all sorts of timing and QA issues. And so what’s difficult is the fact that engineers basically have this tax, this localization tax and then the organization to keep apps, you know, and keep releases fresh in every language that they’re in, that’s actually a really tough problem.

And so the first iteration of the product was to solve it, and we actually solved that pretty well. But it was hard to do that without the services piece because people don’t know translators and, you know, need help getting connected to the services.

Andrew: So you saw this over, and over, and over again, especially somebody who was working internationally and you said, “I think I could create a company that’s going to address this.” You quit, you went out and raised money. Is that the first step you took?

May: No. The first step was finding a co-founder.

Andrew: How’d you find your co-founder?

May: I was asking for intros from people that I trusted. I wasn’t in tech at all, so, you know, I kind of went out there. And this is, like, back in the day when Google Reader existed . . . I love that product, that basically subscribed to, like, every RSS feed that was anywhere remotely related to tech and starting a company, and NLP, and localization and found what seemed through a referral and then kind of looked him up on GitHub, looked him up on Twitter. And I liked what he was working on and kind of what his own side projects were, ML and NLP-related, and these were still early days. And so I reached out to him coldly on Twitter because I knew his name but we hadn’t been, like, email introduced. And we met for breakfast kind of like three days later. And what I didn’t know is, like, he got things like that all the time, people wanting to be as, you know, “You’d be CTO, I’d be CEO.”

Andrew: I bet . . .

May: Pardon?

Andrew: I bet. Yeah. Developers get this all the time.

May: Yes. Exactly.

Andrew: “I have a great idea. You do all the work.”

May: Yeah. Totally. And then I showed up and talked to him a little bit about it, but not too much, and then I sent him an NDA, which I actually don’t remember doing that, but he did send me the email evidence that I had done that. You know, you do like a bazillion steps after the first one to decide to start a company and you kind of forget some of the early crazy shit you did. But we ended up working together, you know . . .

Andrew: How did you convince him? How did you convince him to say, “Yes. I’m going to do this with you?”

May: So it wasn’t a one-and-done, that’s for sure. You know, it took me even a couple years from that . . . I mean, this was 2012, to actually kind of leave my job and really kind of commit to doing this full-time. And it really wasn’t until we said, “We have to move to America,” this was . . . we were in Dubai still, that things really took off.

Andrew: Got it. And so the two of you were just talking to each other, “I’ve got this idea. Would you be interested?” “Yeah, maybe, but I’ve got other people who keep asking about this. I don’t know if you’re weird or not . . . ”

May: And we built stuff on the side.

Andrew: And you both had stuff on the side.

May: Yeah. I mean, we were working together on the side.

Andrew: On what?

May: We would meet up after work, after kind of our day jobs and look at wireframes, work on wireframes.

Andrew: Got it. I’m just kind of imagining what these things can be.

May: Prototyping, yeah.

Andrew: And then you raised money or then you started building the first version?

May: Then I used some of my savings for the first development and my co-founder coded a little bit, but we actually paid somebody that he supervised to do kind of the first bit. And, yeah, and that was my own money. And then I had a friend who offered to basically invest. I was kind of meeting him two or three times to get advice. And, you know, kind of the last meeting he said, “Well, I want to invest, and I will also price an angel round for you.” So that helps because then I had a term sheet for an angel round and then I could go and kind of talk to other people about it. So that was our first money in.

Andrew: How much money was that first seeding?

May: I think that first seed was like a 550K.

Andrew: And by then had you created the first version or did you do that . . . ?

May: By then, we had the first version and I had an alpha customer.

Andrew: So what did the first version do?

May: Oh my god, you’re taking me way back, Andrew.

Andrew: That’s what this is about.

May: So the first version allowed you to easily get a group of translators to translate your stuff, so exactly as kind of what you talked about, you know, “You take this sentence. I take this sentence,” it’s kind of like an [inaudible 00:16:59].

Andrew: So I would upload something into your service, you would break it up and send it to translators, each one of them would handle, what, one sentence at a time?

May: Whatever you wanted.

Andrew: Whatever the amount is, and then I would have to find my own translators.

May: Yeah.

Andrew: Got it. And then you found an alpha customer, how?

May: So it was somebody who I had met through kind of, like, exploring whether to start a company. And he had a news site, where they were writing articles in English, and one of them translated it into a bunch of different languages. Arabic’s the first one.

Andrew: All right, let me take a moment to talk about my first sponsor. First sponsor is a company called HostGator for hosting websites. Let me ask you this, you’ve gotten away from the translations business. Do you think this would make sense for somebody to go to HostGator, create a simple WordPress account that says, “I will translate your blog posts into one other language,” they pick one language, and then they find a translator online, and they start looking for customers, and they see if that idea works, “Personalized, I’ll translate your blog posts, or I’ll translate your articles of any kind.” What do you think of that, May?

May: I think that would work.

Andrew: All right, whether you’ve got that idea or any other idea, really guys, I urge you to go to because not only is it dependable, not only has it been around forever, but it’s inexpensive because hosting, especially at WordPress, it’s a solved problem. Don’t spend a lot of time, don’t spend a lot of money, just go and get it going, and then if you don’t like it, delete it, move on. They have a 45-day money-back guarantee. So if everything I’ve been telling you up until now about how great HostGator is not true, you can cancel.

But I’ll tell you, I’m always opening myself up to my audience to tell me what they think of my sponsors. If they don’t like them, I cancel them. If they do, we keep on re-upping them. And every time I tell you my email address, my personal email address, my wife uses this email address, it’s So if you don’t love HostGator, don’t just cancel, tell me about it. And when you do, like so many other people who’ve signed up, tell me about that too. Go to I literally guarantee you’re going to love it. HostGator, thank you for sponsoring.

How did it go with the first alpha sponsor? With the first alpha sponsor. How’d it go with the first alpha customer?

May: It went great. So, you know, we spent kind of a couple of years doing that. then we moved to the Valley. And what we realized was without actually connecting people to the translators, it was hard to get the software-only business. And so kind of the first micro pivot was in taking what we had built. So after kind of that first alpha, the product developed a lot. And what we got really good at is kind of the solving the engineering piece of the problem, which was helping connect to code and actually make localization continuous. So kind of the first shift in the business came from when we moved away from localization and tried to . . . and this was already . . . I mean, some of our customers in the U.S. were using Qordoba to write English, and what we realized . . .

Andrew: What do you mean? It was American English speakers using Qordoba to write English because?

May: Because Qordoba was the only place where, for software, all of the content of the repository sat in one place. So, like, if you look at a software screen, you can get an error message and a bunch of UI and maybe an onboarding kind of tutorial, and all of that content sits in different places. And so you actually don’t necessarily know which engineer is responsible for which part of the service except that those strings actually live in Qordoba because that’s what you are using to localize.

Andrew: So you created something that was so good that people were just using it as their main writing platform. And by people, I mean, engineers were doing that.

May: So the product folks who needed to interface with engineers.

Andrew: Got it.

May: The first insight was, “Oh, wow, we don’t have a content management system for software products, for product UX,” and so we kind of raised the big money and kind of went out and built a big business that we called strings management. Now, if we hadn’t started in localization, we wouldn’t have gotten those insights at all. And the traction then, that’s when we got up to the 4 mil ARR number that the traction there was really around the value prop of, “I shouldn’t need to file a Jira ticket to add a comma or change how I spell my name.” And there is a fundamental disconnect between a PM, a product manager or a marketer who cares about the words and cares about the on-brandness of the copy that’s in the app. And then, the engineer, who actually has to write it up and they’re writing it up from, like, copying the mock, or looking at a sketch file, it’s a pretty disjointed process [inaudible 00:22:06].

Andrew: So let me ask you this, let me come up with a with a real world example that maybe you could help me explain what happened before your software and then after. Right now, you and I are connecting via Zoom. If I were to hit this end meeting button that’s on the bottom right corner of my Zoom screen, I get an error message. I think it says, “Really leave this meeting, yes or no?” If somebody looked at it, a product person and said, “Wait, why are we saying, ‘Really? Leave this meeting?’ that’s just too distracting, can we just get rid of the middle question mark?” before you came along, a situation like that would have been handled how by the product person?

May: And that person would have filed a ticket, needed to figure out, you know, what backend engineer was responsible for the error service on the Mac desktop client, I’m assuming you’re working on Mac, assign it to that person, that person’s looking at a copy change relative to all these other cool things in the sprint, and it’s kind of trying to fit it in somewhere. And then that person needs to go and, like, chase down the file of where that might be. And so, you know, Ctrl F if everything is in a single application file, but the reality is we’re all micro-services based. And so they’re actually looking at a number of [inaudible 00:23:23].

Andrew: So it’s like the person who caught that whose responsibility is to make things read better would have to create a task for somebody else who goes, “I’ve got all these other tasks, and I don’t even know where this is,” and hunt it down. After your previous version, what would that look like?

May: So that person would go into Qordoba where all of their strings sat, and they would literally just start typing the words that they saw on the error message and that row would show up in Qordoba because it basically indexed all of the content, they would make a change, complete it, and then at the next integration point, so it could be real-time if they connected Qordoba via API, it could be a pull request into GitHub if they’ve connected via GitHub, however it is that they’ve decided to integrate with Qordoba they’d be able to push that change and the engineer didn’t have to do anything.

Andrew: So all the language that was on the screen, visible to users would be in one place sucked into Qordoba, and that product person would not have to know how to figure out . . . the product person wouldn’t have to do anything except just go actually write it themselves.

May: Yep. Exactly.

Andrew: Got it. And that was a thing. And so, right along, the, “Really leave meeting,” might be a button that says, I don’t know, “Invited,” and they might say, “Well, invited is past. We want them to use this button to invite. I want to get rid of the D from that,” they just go back into Qordoba, make that change. Got it. That’s what you’d created even though what you wanted to do was use that as a basis for translation to other languages. It made sense for product people to use it just to interact with the software that their users got. And, at that point, how big was the company?

May: So at that point, we’re maybe, you know, a couple mil in revenue on the localization piece. And the realities of kind of that go-to-market . . . you know, we’ve learned a ton of lessons on go-to-market. It’s funny. It’s sort of, like, you need a syllabus of failure, like you get your articles of incorporation and then with it, like, stapled on top is like, “Here are all the mistakes you are absolutely going to make no matter how much you read about all the things you need to do when building a business.” And so, you know, one of the mistakes we made was probably not talking to enough people before deciding to make that our go-to-market.

And, you know, you could be good at sales, you could get good at sales and sell anything. I mean, we had incredible customers on that product too. But what was happening as we, like, really went to market with that value proposition of strings management, deal cycles weren’t getting shorter. There still was a fundamental mismatch between the champion, which is the content people, and then the gatekeepers, which are the engineers. Even if the value proposition is to remove the engineers, you still got to get on the roadmap for that initial integration.

Andrew: So you would get the person who’s writing the words to say, “Yes, I want this,” they would need to get the . . . first of all, it would take you a while to get them to buy, and then they would need to get the developers to say, “Put this, integrate this in for us,” and the developers had a bunch of other stuff.

May: It was even another stuff, like, yeah, that’s exactly it.

Andrew: What’s that?

May: UX writers would want to use it, then they have to convince the product people who got the budget because UX writer don’t have budget, and then they would have to convince the engineers. And so there’s a lot of convincing.

Andrew: Got it. And so you’ve got one of them to say, “Yes, finally,” and you thought you were on track, but all those other things that had to happen after a purchase was a struggle.

May: Once people got to it, yes, the product was pretty easy to roll out. But, you know, I’ve learned that there’s a big difference between folks who are stakeholders and folks from whom buy-in is nice. And a stakeholder can block your deal, can block all the things that they’ve got going on. And I know . . . I mean, we run a product organization. You got to do the few things that are really going to move the needle. And invite versus invited, like, make a huge difference in the success of Zoom versus latency, versus all the other shit that these engineers got to work on. And so it was nice to have. Like, the burning need wasn’t there. And I think, you know, we could have built a good business there. It would have been an outstanding business. And, you know, I felt like we had the team around the table, from engineering, to product, to the execs to really build an outstanding business.

The other thing that we saw happen was, you know, the product people and the UX writers, like, you know, they know nothing about localization and what they wanted to do was about kind of the core product. Engineering leadership knew that, kind of down the road, they needed to do integrations like the one we were proposing once they needed to localize. And so they kind of kicked the can down the road. And so we had stuff getting blocked or, like, come back next year type of conversations. And so, yeah, for a lot of reasons, great product, market not ready.

Andrew: How did you get so many sales? What was working for you?

May: So we were good at getting people to talk about their problems. And the problem . . .

Andrew: You were good, like, you personally, or did you hire someone who was especially good at it?

May: We had a couple of reps throughout this period, one really outstanding one. And, you know, we had a very commercial co-founder. So my CTO is our, like, secret sales weapon because customers love him. And, you know, we built a lot of shit for people, and we were good at it. We were fast.

Andrew: If they would ask for something and Waseem would make sure that they would get it.

May: Yup.

Andrew: And that goes a long way with customers because they see constant improvement, they see that their needs are taken into account, and then you also said something that I wrote down, you’re good at getting people to talk about their problems. So you get in a conversation with a potential customer and you say, “Tell me about this problem,” they’d feel it in a significant way, and they would be the ones who would eventually get the yes, but it was still painful for the other people in the organization.

May: I think it’s hard for entrepreneurs to know when your early adopters are really just early adopters. You know, when you think about the technology adoption curve, is this going to be for everybody, and how long will it be before it will be for everybody? And I felt like it was going to be a long time before early adopters became more mainstream.

Andrew: I want to get to then the decision to pivot, but before we do, you’re somebody who didn’t come from enormous wealth and to have this much revenue and give it up, it’s a tough decision. I wanted to get to know your background a little bit and then we’re going to go back into what happened after the pivot. How do you feel this interview is going so far for you?

May: Oh, it’s fun. You know, I’m feeling like anxious thinking about some of the things that we went through, but . . .

May: Re-living some of this made you feel anxious. So far as we’re talking, I feel like you’re one of the most composed people I’ve ever met and talked to even before we got started, you said, “I’m concerned about doing this interview right,” but I’m looking at you and you seem super composed. Like, when was the point where you felt so anxious that you weren’t this composed? I don’t see it in you.

May: I mean, you know, being a startup founder, I think it’s a career for a lot of people and staying composed and keeping your head in the game is one of the things that you just learn how to do.

Andrew: And when it wasn’t working for you, what were you like? I know, for me, what I’m like is . . . I said this before, I wake up in the middle of the night and go, “How did I say that thing? How did I allow it?” The other place where it hurts me is on my runs where I’m going for 6, 12, 15 miles, there’s nothing to do. Yes, you can listen to podcasts, but eventually you’re listening to your head. And if I regret something that I said or did, that goes over and over in my head. Like my Fred Wilson interview, the VC, I, for years, lived it saying, “I could have done so much better. Why did I do that?” And that’s the way that I express my pain. For you, where does that come out?

May: So I learned a few years ago to try not to recycle emotion. So when I am feeling anxiety, or feeling regret, or feeling fear, and I really just try to sit with it and, like, literally just try to feel, like, where in your body it hurts and really let it pass through you. When we try to stop the emotion before it’s really passed through, the body keeps the score. And, you know, so many entrepreneurs have back pain. I’ve got like the tightest shoulders any masseuse has ever seen. Like, this comes from us not allowing things to really pass through. And when you are replaying things, it means you haven’t . . . for me, anyway, it means I haven’t allowed myself to really sit and absorb the emotion and because of that, I’m recycling it because I’m happy to sort of stay on the surface.

Andrew: Can you give an example of that, or do you want . . . why don’t you take a moment, think about it. I’d love to hear an example of it. I want to tell you about my second sponsor, while you’re thinking about the time where you are in deep pain. My second sponsor is a company called Toptal for hiring developers. I’ve said this before, as I was walking here at Regus to get coffee, there was a guy who was sitting in a Toptal t-shirt, and I said, “Hey, do you work for Toptal?’ He said, “No.” He said, “I got a company called Quantum Collective. What we do is we do artificial intelligence.” I said, “What does that mean? Everyone’s throwing that term around.” He said, “You notice that there’s some scooters here that sometimes they’re just left, like, in random places?” Like, “Oh, yeah.” Are you in San Francisco, May?

May: Yeah.

Andrew: You are. I don’t know if you remember, there was one scooter company, I won’t put them down here, it was . . . I forget actually, it was either Skip or Scoot, I will put them down apparently, they had all the scooters on the Embarcadero all the time. Now meanwhile, in the Embarcadero at 9:00 in the morning, at 8:00 in the morning, nobody’s going for a scooter ride. There’s nobody up over there. That’s where tourists come later in the day and on the weekends. Where you want the scooter is in Noe Valley, in the Mission where people live and then they want to ride the scooters. Anyway, they were terrible at predicting and as a result, they suffered for it. He goes, “We have scooter companies, for example, working for us and what we do is we use artificial intelligence to predict where people are going to need the scooter so they could put the scooters in their van, move it over where it needs to go,” and so on.

I go, “Okay, great. Why are you using Toptal?” “Because you know how hard it is to find engineers, you know how hard it is to find people who know artificial intelligence, not just because it’s a cute thing to say but because it really matters, data analysts, scientists. We’ve searched ten different places to find people who can do this well. We’re getting hired . . . ” He’s a bootstrap company. He’s getting hired to do this for companies. He doesn’t have enough people on staff. He goes, “I went to Toptal, they not only found people for me,” he says, “Now, when a client of ours needs us to transition the work over to them so they have artificial intelligence capabilities, we hire from Toptal, we transition over to them.” And that’s what this guy Michael does. So many other people here in San Francisco use Toptal.

I urge you, if you’re listening to me and you’re hiring, you need to go check out The companies that you know well use Toptal. Sometimes they’re not as open about it because they want you to think that they have internal capabilities that are just magnificent because Toptal people are just, like, every other person in your company. But I’m telling you, companies you know and admire have used Toptal and continue to. You should at least check them out.

If you go to top, they’ll give you 80 hours of Toptal developer credit when you pay for your first 80 hours, in addition, to really get this no-risk trial period. So all you have to do is go to top as in top of your head, tal as in talent, When you do, the first thing you’ll do is schedule a call with a matcher, just have a conversation. If it’s a good fit, go for it. If it’s not, no problem, no harm,

Do you have a moment when you had to let that feeling go through you?

May: So I was listening to what you’re saying about Toptal. That was really compelling. But, yeah, absolutely. Striking the balance of holding people accountable and really making sure people are bringing, you know, their best efforts to a problem and trying to make sure that, you know, you’re doing this in a super respectful way that allows them to feel trusted and respected, making sure that you’re creating an environment where people can take risks and absolutely can fail and get it wrong, where people feel empowered to challenge you, like, these are all things that are running through your moment in your head when you’re trying to figure out what to actually say to somebody in a one-on-one or in a team meeting.

And so, you know, I am frequently angry, and anger is the way that your body says, “You know, shit is just not going right.” And how do you respond but not react to that, and that is really around just allowing yourself to be okay, feeling angry. You don’t have to make the other person angry. You can’t and should not be transferring your anger to them. You react within yourself, and then should be able to respond in a way that gets you the outcome that you actually want without you needing them to feel your anger.

Andrew: So if someone’s done something to let you down at the company, instead of saying, “Just stop it, let it go, let it go,” you won’t let it go. You’ll allow yourself to be angry, not angry at them, not screaming at them, but you’ll say, “I am kind of pissed that this person didn’t adjust the way that I wanted them to. I hired them to be better than me at this, and now I have to keep telling them what to do.” And you’ll allow that feeling to go over you and then to wash out so you can experience it and then come back to being yourself.

May: And I don’t not say that. I don’t not say it to them. But when I can speak without the emotion, it’s so much more powerful. Especially in the early days, I think it was hard for people to hear what you’re saying when all they hear is the emotion. We’re wired to hear emotion versus the content of what you’re saying. So if you can kind of feel the emotion separately from communicating what you need to get communicated, that’s, like, arsenal, like, CEO things you got to learn.

Andrew: I find that the best way for me to do that is through journaling. If I say, “I’m angry at this person,” and I journal it out, I feel so much better because now I’ve forced myself to think through what I’m angry about. And sometimes, it turns out I was wrong. I was just, like, in my head making it bigger than it really was. Your background, where did you grow up?

May: So I was born in a village in Lebanon. My family moved to Canada when I was little. And we move to Windsor, Ontario . . .

Andrew: Wait, before we go to Windsor, what was it like to grow up in Lebanon?

May: So this was the ’80s to late ’80s . . .

Andrew: What was Lebanon like back then?

May: I mean, I was born at home, we didn’t have electricity, there wasn’t a phone. I think our village got phones in, like, ’96 or ’97. It was beautiful. I had two brothers. I’m Irish twins with my next brother. So my mom had three kids in three years basically. So we’re all just really, really close. And it really did take a village and, you know, I just remember being outside all day for years, house to house, you know. I mean, there are maybe 20 houses in our village and just surrounded by farmland. So it was a beautiful place to have my first memories.

Andrew: What did your dad do?

May: So my dad drove a truck. When we were there, that’s what he was doing. So my family were farmers, and so he would drive kind of produce into the big city to sell it. And then when the war happened, his him and his brothers were smuggling appliances into Syria because we were on the border and there really wasn’t anyone paying attention, so. I probably shouldn’t be saying that, but dad was a smuggler for a little while.

Andrew: And then you got to Canada.

May: Then we got to Canada and then . . .

Andrew: And . . . Go ahead, what was that like?

May: And then we had my sister. That was good. I’m the oldest of eight now so we have . . .

Andrew: Eight.

May: Yep.

Andrew: Wow. By the way, you know, last night, because I knew that I was coming to do this interview with you, I looked up Lebanon on the map just to get a sense of . . . it’s much smaller than I imagined. For some reason. I thought Lebanon was huge.

May: Oh, thank you. Yes, because you’ve probably met so many Lebanese people.

Andrew: What has so many Lebanese people?

May: I said maybe you’ve met so many Lebanese people.

Andrew: I have. Yeah, absolutely. I want to engage them in conversation about what’s going on. Like, there was a friend who just went back to Lebanon a couple of years ago. And, for some reason, they feel like they’re not invited to talk about it, and I’d like for them to talk about it more. What was it like for the transition into Canada?

May: I loved it. You know, school had water table, like, it was, like, going to heaven.

Andrew: What’s a water table?

May: You know, like when you . . . do you have kids?

Andrew: I do. You mean like a table where there’s water and the kids can splash . . . ?

May: Yeah. That’s first memory of being, like, “Holy shit.”

Andrew: You know what, that is kind of a thing, holy shit. We’ve given our kids a table so that they could splash around instead of a puddle.

May: Yeah. It’s amazing.

Andrew: And so you notice that your parents ended up doing what here in Canada, anyway?

May: So my mom worked at a bakery, she made pita bread, and it was a Lebanese-owned bakery that she could walk to. It’s called Francis’ Bakery. All of, like, my mom, my aunts, everybody, it was sort of, like, the rite of passage when you immigrated to go work . . .

Andrew: At this bakery?

May: At this bakery. Actually, it’s a really nice story. So that man, his son ended up being mayor of our city, and our city is, like, 400,000 people now. So he like ran for . . . he was not that much older than me, maybe 10 years older than me, Eddie Francis, and, yeah, he ran for city council in his 20s. He’s, like, the youngest city councilman in Windsor, Ontario, ever. I think in Ontario history even. Anyway, he ended up being mayor, really lovely man. But his dad, you know, helped my mom and my aunts kind of make a bunch of money when they first moved.

Andrew: And your dad was in a die shop. Is that right?

May: Yeah. So he started in . . . so he works at a tool and die shop and . . .

Andrew: The reason that I’m bringing it up is one of the surprising things that you said to our producer when you had that conversation was it was chaotic, and it influenced you somehow that it was so chaotic. What do you mean?

May: Yeah. It’s interesting. You know, I think on the one hand, it made me calm when things were chaotic. So that’s kind of a skill that I have today. You know, a bunch of kids in the house with my aunt and uncle. You know, everybody had two or three jobs and was trying to learn English. Like, it was chaotic from a kind of home sense. And then, work, my dad ended up starting his own business and, you know, cash flow was always a struggle. And I went to work with him on the weekends and after school. So I kind of watched him build his own business. But, yeah, I mean, I didn’t feel like he had good controls. And, you know, I’m kind of, OKR driven now, and I’ve got this like crazy spreadsheet and literally watched every dollar row by row move, you know, very detailed, daily updated 13-week rolling cash flow. And I think, you know, that is a reaction to kind of watching how he ran his business.

Andrew: You don’t want that kind of chaos in your world.

May: Yeah.

Andrew: So now that I get a sense of your background, it’s just even more impressive that you were able to give up $4 million in recurring revenue, in annual recurring revenue to transition to this new thing. How did you discover this new thing?

May: So, remember, I mean, we like we’re elbow greasing our way there and that never feels good. Not that I expected anything to come easy. Nothing does come easy, and the challenges actually are perpetual, just the problems are changing. You know, when I looked at kind of our big vision, like literally from years ago, the big vision is optimize the way people write. Writing is our best technology. It was our first technology. It was how we went one to one, to one to many. And it still hasn’t changed. It is your brain and a blank cursor on the screen, and kind of the big hairy audacious goal for years has been, “Let’s make writing better.”

And I felt like what I had been doing for the past few years was rather than going to climb the mountain, I was sort of, like, finding this hill and going to the hill and, like, taking a deep breath, take my backpack off, making sure nobody was chasing me and then, like, setting my eyes on the next hill. And I was like, “Look, I mean, let’s not forget why we’re in product UX. We’re in product UX because we think helping optimize and make this content good allows us to then help do it in marketing and help doing it in customer success, etc. So let’s just go fucking do that.” And that’s what we did.

Andrew: So did you go back and talk to customers to make sure that you were right about the problem, that you were . . . ?

May: Yes.

Andrew: How did you do it differently this time?

May: Really good question. So this time, it was about . . . first of all, I didn’t do it myself because I’m biased, and I’m good at selling, and we hired our first head of product. And really being able to actually have somebody else direct to the line of questioning helped a lot because sometimes you create your own . . . I mean, you’re a CEO or you’re a founder of your company because you are really good at a reality distortion field, and it’s very easy to believe your own stuff. I’m not saying that, like, I discount my own product intuition or any of that, but I thought at that point, you know, I had let the market take me on this journey. And I really wanted somebody to talk to customers about the pain that we had this instinct about, and we did that.

And you know, we hired somebody from the B2C world . . . actually, not the B2B world because in the Qordoba of today, our customer, you know, the champion is the champion, and the budget holder is the budget holder, but our user is that writer. So the end user of Qordoba is the person who needs to want to interact with the suggestions, who is the person who needs to be excited every time they get a little red squiggly because they know that’s going to improve their writing and make it more on brand, make it more compliant with what the company wants.

Andrew: You hired somebody to go and talk to, not just the people who are buying, but the people who are going to be using your software.

May: Yeah. Absolutely.

Andrew: And what did you learn from those conversations?

May: I mean, they’re absolutely ongoing. I mean, what we did was kind of customer research became a practice, as part of our product in a way that it wasn’t. I mean, my customers are on WhatsApp, like, it’s not that we are far away from customers, and actually it was too close, like, the commercial relationship and then how that translates into roadmap and vision, like, sometimes that can actually hinder you, not help you.

Andrew: What do you mean? So you’re saying that when you’re too close to your customer, it can make it harder to understand them?

May: Yes. I guess that’s what I said. But what I’m really saying is just because someone will pay you for something doesn’t mean there is a big business there. Those are actually two different questions.

Andrew: So then, what’s the question that leads you to know that there is a big business there?

May: Are there use cases that are broadly applicable to other segments, and is it validated by people who don’t know you and don’t know the product?

Andrew: And so you would go to the end-user, who doesn’t know you, who has no . . . like you hadn’t persuaded them to buy so they’re not bought into your magnetism, into your sales process. And you go to them and you ask them, “Here’s what I think I’m creating, would you use it?”

May: Yeah. And even more specific, like, you know, “Here’s what we’ve got. I’m going to give it to you for free, and I’m actually going to watch you use it. And you don’t actually use it as much as I thought, what prevented you from doing that?” We gave away the product for the first time. I had never done that before.

Andrew: So you created first a minimum viable product, which did what?

May: So it was a really clean content editor online. And when you put content in there, whether you’re pasting it in or writing it from scratch, it gave you suggestions on how to make it better, so clarity, conciseness, readability, grammar, spelling, and then tied to what was very basic, really just a terminology manager, and now since we built out a whole writing style guide.

Andrew: What was the terminology editor?

May: Literally, like, you know, things like, “We say customer. We don’t say client.”

Andrew: Got it. So you look for the word customer and you tell them, “Actually here we don’t use that. We use client.”

May: Yes. We just replace them.

Andrew: I never understood that that was an issue. It was an issue. I don’t know why, but it does make a difference for people. And I remember my first real job, my boss said to the person who’s closest to, he said, “We never call our people customer. We call them clients.” There’s a sense of, I don’t know . . .

May: Prestige.

Andrew: . . . concierge and prestige in the relationship. And so you did nothing but that and then you said, “Would they even use it? We’re giving it to your people. Go in and use it?”

May: Yeah. Absolutely.

Andrew: What did you learn about that, beyond the fact that they would use it?

May: I mean, and we’re absolutely still learning. Our go-to-market is still in its early days. We are just hitting kind of our first benchmark here. What we learned is professional writers are our constituents, people who write all day. And those power users have different sorts of needs than the people who are buying the product. The people who are buying the product want the end-users to be super happy. They also want to know that everything that is being published is being reviewed for all of these things.

I’ll give you an example. We’ve got an insurance company, a Fortune 500 insurance company, who’s a great customer. And for them, promissory intent is this big thing that they used to have lawyers review content for. Like, they can’t mislead consciously or subconsciously through their language, a user to think, a potential customer to think that they’re going to get stuff for free, or that, you know, certain conditions are definitely going to be covered. And so, certainly, if you use the word free, Qordoba’s going to underline it for you, but there is more subtle phraseology that they turn into patterns in Qordoba.

Andrew: And that’s the person who’s buying it.

May: A person who’s buying it.

Andrew: They as a business can’t be seen promising something that they can’t deliver or promising anything for any reason. The end-user though, the person who’s sitting and writing needs what?

May: That person needs an unobtrusive writing assistant. It’s as if, let’s say, Andrew, you were the person who was kind of the copy Nazi in the company, you’re kind of standing over their shoulder saying, “Okay, five minutes before you are finished, I want you to change this, this, and that,” and then they’re done. They don’t have to send it to anybody. And so they want to know that they’ve checked off all of the boxes, but they want to do it at the end, not while they’re writing, and they want to do it in the least obtrusive way as possible.

Andrew: I wouldn’t have thought that after the writing. I would have thought that they’d want it while they’re writing. But it makes sense. When I’m writing, I often will even turn off spell check and grammar check. I don’t want the distraction. I need to get the words out. Got it. And so they want an easy way to produce something that the person who needs it is going to pat him on the back and say, “This is great.”

May: Yeah. It’s not going to be this like constant back and forth that’s so annoying.

Andrew: I get that. So then, now that you found the product, you found customers, why turn your back on other revenue? Tell me if this is right, did you say to your team, “Even if you bring me a customer who pays us a million dollars for our old product, I don’t want them. I’m going to say no”?

May: Yeah. I did say that. Yeah.

Andrew: You did. You said it?

May: I did. I said it I think, like, a week after giving birth, so, like, there’s nothing like having a baby to make you not give a shit. So there was, you know, a lot of resolve and a lot of clarity of thinking that if we’re going to go where we’re going, we just can’t do anything else. And the reason I had that clarity, not I was some genius, because I did it the other way and it didn’t work. Like, we had a couple of quarters we were sort of trying to do both and we didn’t have any customers. The product didn’t get good enough. You have to bet the farm.

Andrew: Because you were too dependent on the last stuff, people weren’t invested enough in building the new thing.

May: You know, we know that we need this feature, we need distraction free writing, for example, to give you an idea of a feature, but your engineering team, like, got some, like, little request from a customer on the old thing, and the person who’s going to work on this new thing is now dependent, is now busy and needs to do that. I mean, like, your classic engineering team needs to really be focused on one direction because the switching costs are so much more painful than you think. And it’s not just about building this little thing here or a little thing there, it really adds up and you have to be so clear, and so convincing, and so repetitive so that the team really believes you.

Andrew: That makes sense. And now I understand why you also told our producer, “Look, you can read a million blog posts, maybe . . . ” I’m paraphrasing, but it’s something like you could read infinite blog posts about how you need to focus, need to focus until you’re an entrepreneur actually suffering from lack of focus, you don’t fully get it, and that’s where you were. Even though, you’re fully focused, it makes sense, more . . . ?

May: And I was trying to be even more focused.

Andrew: What do you mean?

May: We’ve got a really wide ACV distribution, we’ve got customers who pay us 18K a year, and we’ve got customers who pay us 120K a year. Those are two really different types of customers, two really different types of sales motions. So we’re narrowing even further. We’ve got customers in health care, in financial services, in professional services, and tech. We’re narrowing even further. So it was fantastic for us to get all of this learning in the market the past couple of quarters. That’s what allowed us to get, you know, to where we are in the last six months. But we scale and we go from initial traction to initial scale by focusing even further from a go-to-market perspective.

Andrew: And so you’re going to focus on who now?

May: Well, I’m going to keep that my little secret for now, Andrew, in case I have competitors listening.

Andrew: All right. Let’s close it out with pet peeves. One of my pet peeves from writers is I hate “click the link.” You see me, the whole time I’ve been taking notes as well writing on an iPad, there’s no click a link on an iPad. There’s no mouse on it. There probably will be. There isn’t? On my phone is where I check email. If you’re writing an email, we’re all checking on the phone. What’s click? It feels so antiquated. But honestly, in the grand scheme of things, not that big a deal but it bothers me. What’s one of yours?

May: Oh, I hate lack of parallelism in bullets or lists.

Andrew: Oh yeah.

May: I just want to die when I don’t see, like, parallel constructions.

Andrew: So you mean it would be something like, “Here five things that I love. I love rainy days and sunny days.” Like it’s not . . .

May: You know, in, like, a value prop and I’m thinking like B2B world, where you’re reading people’s websites and it’s like, “Okay, the first thing you can do with the product, get everyone on your team to be on the same page. Second thing you can do with your product, like, beautiful interface.” What?

Andrew: You started with get everything. Got it. I’m with you on that. One of the things that I liked about Qordoba was the AP style guide. You can actually have all these things that you’re supposed to learn in school that people learn, but yet forget to use, or you remember five things and you think you’ve mastered it, the whole thing could be in the software if the company decides, “We write using AP style guide.”

May: Yeah. Absolutely. And, you know, things like date formats, things like currency formats, you know, do we use decimals, do we not use decimals, like, especially for teams of multiple writers, especially at larger companies, this stuff is a lot of copy editors spending a lot of time on it that really, their time could be used elsewhere because there’s a level of professionalism that content conveys when it’s internally consistent like that. And those are just the tiny things, like, we can turn a 400-page style guide from AWS into the super easy to understand and to consume interface. And we did that because we read thousands of these style guides and kind of took the best of those elements and organized them. And so it’s nice. It’s taking chaos and turning it into organization, and the best products turned chaos into order. You know, that’s what we can do.

Andrew: I feel like the young May watching her dad’s chaotic work environment would be very proud that you’re doing this. And I’m also feeling, like, the person who I talked to the other day who is hiring writers and has an Excel spreadsheet with all the things that he wants, he’s hiring him through agencies, and he wants all of them to write in a similar way so that he can publish on his site. I feel like he’s someone who’s going to especially get excited about what you built here.

May: Awesome. Thanks.

Andrew: All right, the website is . . . Here’s my big problem with it, Qordoba is hard to spell. I’m going to say Qordoba, people are going to spell it with random letters. It’s Q-O, which already is an issue, Q-O-R-D-O-B-A, what’s the name mean?

May: So it’s named after the city in Spain, Cordoba, [inaudible 01:00:24] and Q because that’s kind of webby. And in college, I read a lot of poetry from kind of pre-Medieval Ages, [Andalucía 01:00:33], and just really loved it and loved how multicultural it was. I love poetry even today. I mean, there’s a poet named David Whyte who gets me through some really hard days at work. If you are an entrepreneur and haven’t read David Whyte’s work, please read it.

Andrew: David Whyte. What’s a poem or a book of his that we should [inaudible 01:01:01]?

May: W-H-Y-T-E, just the latest stuff. I mean, he’s on a lot of “The On Being” podcasts on Spotify. Just look up David Whyte on Spotify.

Andrew: David Whyte on your favorite podcast app.

May: Perfect.

Andrew: All right, and everyone else, go check out Qordoba, or everyone also check out Qordoba, and I want to thank my two sponsors who made this interview happen. The first, if you’re building a website of any kind, translation site or anything else, go to People who’ve signed up with different hosting companies have been switching and telling me that they like it. By the way, they don’t say, “I love it. It’s amazing. You changed my life.” It’s not supposed to change your life. It’s just supposed to let you run your business without focusing on hosting and be proud that you’re saving money, And the place where people do get enthusiastically in love with me for recommending that they sign up for, it’s Toptal. Toptal is where people are like, “I didn’t even know this thing existed,” I’m grateful to them for sponsoring and to you, May, for being here.

May: Thanks, Andrew.

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