The story behind Boomerang

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Today I’m talking to the founder of one of the OG email marketing tools, Boomerang.

I remember they even created the email game to make getting down to inbox zero fun. They were playing around with this stuff and it was clever. It was ahead of its time and I feel like in many ways they were neglected because they weren’t part of Silicon Valley the way others were.


Aye Moah

Aye Moah


Aye Moah is the founder of Boomerang, which allows users to schedule an email to be sent later and create easy email reminders.


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 built their businesses often in a tough competitive environment. Like today’s guest, AMO is the founder of Boomerang. They are like the OG of email marketing tools. Back before anyone believed that you could create an add-on for Gmail, and I don’t even know if Gmail like knew that you could create an add-on for Gmail, they created an add-on for Gmail that would allow someone to send out a message and then get a boomerang response back to.

To make sure that the person they were emailing responded, or was followed up with. That was one of many tools. I remember they even created the email game to make getting down to inbox zero fun. They were playing around with this stuff and. It was clever. It was ahead of its time, and I feel like in many ways they were neglected because they weren’t part of Silicon Valley the way others were.

And then one day, and I, I was a user of there, so I, I followed them and then one day, I read this article somewhere about how they needed funding and they were so clever about the way they got it that they were willing to offer an investor, a taxi ride, I think, to the airport. And through that ride they raised money and I thought, these people are pretty ho good hustlers. then I started wondering over the years, what happened to them. What happened to them as a lot of their features, like this bounce back feature was copied by everyone from, I think Gmail has it. I know Outlook copied it. What happens when there are all these new players who come in who are charging what happens to Boomerang?

And while I’m at it, why is it not called Boomerang? Why they have that other funky name that you know that I don’t even see used anymore, and why did they even use it back then? There’s so many questions that I’ve got for her, but the big thing, How did you start? How did you get here? In the face of so much difficulty, and we could do this thanks to two phenomenal sponsors.

The first, if you’re working on a great idea and need phenomenal developers, you already know, you should be going to And the second to do email marketing, right? Meaning with all the features and the right price, you should go to send in But I’ll talk about those later.

Mo what’s the revenue now? Give me like a sense of where,

Aye: between eight to 9 million arr.

Andrew: Impressive. How much funding did you take on overall?

Aye: in 2011. That’s it.

Andrew: That’s it. That’s it. Okay. All right. And today the features are, I, I can go through the features, like yes, there’s still the bounce back. Uh, the Boomerang feature, the scheduling feature, which means while you’re in your inbox, you can make it easy for somebody to schedule with you. Right. Give me some of the

Aye: have, uh, real time. AI assistant to help you write better emails. So when you’re writing an email, you wanna make sure that your tone is on point, your politeness is, you know, to the right level and making sure that your email is as responsible as possible. So if you’re doing outbound and cold outreach, you know the first impression you make is really important.

So for those emails, we have respondable.

Andrew: like, like Grammarly, but for results, you’re not checking to see if my grammar’s right. You’re checking to see will I get the response I want. Based on your experience, having

Aye: Exactly. We also have this unique position. We’ve been tracking whether, which of these emails have gotten a response or not from the response tracking feature that you mentioned earlier. Right? So we have millions of data points to track. If you read 10, uh, email this way, did you get a response? And that data set was the training ground for us to build a responsible. And then we also have things like in BPAs, which is, you know, we believe that people are getting too frazzle, people are getting too interrupted, and there is no time for you to kind of make space for your mind to be focused on what matters. Major initiative, right? When you need to sit down and write this strategy document, you need to pause your inbox and be able to go without interruption.

Um, so that’s, we also have things like you can actually get,

Andrew: That’s like the vacation autoresponder, but it works for minutes or hours

Aye: uh, it’s more. The vacation responder in the sense that it just doesn’t send back out. Hey, I’m not checking. Email is actually stop the email from coming into your inbox in all devices. So you don’t, you know, you’re outweigh of kids or you’re having your family time. The email notifications are not paying you all the time.

Andrew: Okay, let’s go back to where this started. Why is the company

Aye: uh, Burmese word. So I’m originally from Burer. It’s a Burmese word for, uh, for telling the future through magic. We wanted everything we build to feel like magic to the user where it just Fs and we kind of anticipate almost your need on what you need to do and make it fless.

Andrew: Okay. Because you weren’t, Is it because you weren’t sure where you were going with the business? Or you just said, We wanna find a way to make things magical, effortless, and email was

Aye: Yes. Um, it goes even farther back. . Do you really wanted to get into this? We have. We had a product called, it’s called Unsear, in the sense that you don’t have to search when you’re writing an email. We wanted to expose. What are the other pieces of information in your corporate network? I think we were thinking about like basically indexing SharePoint and giving you the information that you need for the email that you are writing and maybe also give you like, here are the peoples from your, you know, company that you need to, uh, contact with for the project that you’re working on.

So that was the original idea of where we wanted to start, and that’s why it.

Andrew: Well, it was it, because y you said this will be our first point, but we are going to create magical experiences and we have an ambition to go. It was, Oh, I thought you were maybe hunting for the right thing. No, you wanted to create a portfolio of, of software all doing different things with one common, uh, co with one common.

Concept, simplify the thing that people do a lot. And then how did you end? Email was just one of them. How’d you end up doing email

Aye: The main thing was, um, we were getting our own, you know, follow ups and everything else that’s related to the modern inbox management taking up most of our days. Right. So both Alex and I were working, you know, we were four or five years outta college and we were working at big companies. We weren’t doing our job as much as we were doing inbox management, and I try everything.

I try 43 folders, right? G T D, hacking it into my own inbox. We were trying out with tiny little script that we find, and there was nothing that was quite like on top of what I need to follow up on and what I need to remember, which email. So I try everything from like putting things into the calendar.

right? Then your calendar is full up. All the reminders, like nothing was quite there. So we started hacking around to see we can solve that problem for ourself. And it did. And then we started showing it to our friends and they’re like, Yes, I need this. Give it to me. So it started square from there.

Andrew: What was in that

Aye: Uh, mostly just the snooze ability to bring it back to your inbox, and we didn’t even have the response tracking yet.

It was just like, I don’t need this now. I’ll need it in three weeks.

Andrew: Got it. It’s in my inbox right now. I usually would save it as unread, but then it clutters up my inbox. If you could just take it away and send it back. How did you do it back then? I don’t think Gmail had

Aye: had it around,

Andrew: it?

Aye: uh,

Andrew: What did you

Aye: we did a Grease Monkey script on the browser side to get the front end integration. And then on the back end we just, uh, did the IMAP integration into Gmail, and then we basically,

Andrew: So in Grease Monkey, I don’t think it even exists anymore. I don’t know if it does. It’s a plugin that basically let other plugins do some magical work, usually by hiding things or making

Aye: You are adding injecting JavaScript onto the Gmail page with Grease Monkey.

Andrew: Okay, so you did that and then because Gmail did have imap, I think from the very beginning you were able to, To do what? With the mail? You would

Aye: we actually move it out of your inbox by applying a label called Boomerang to it. And then for a certain amount of time, and then we set a timer with Crown, and then when the timer comes up, we move it back to inbox.

Andrew: Got it. Okay. All right. This fairly basic and easy to do, it just shows a sense of, I don’t, I don’t know of scrappiness of duct tape type creation and also how big the need was that people would install Grease Monkey. And I know at the time people were more curious about what else could they get their computer to do and they were willing to do it.

But also there’s like a privacy

Aye: was kind of

Andrew: were willing to do it.

Aye: install this in their inboxes from, you know, some randoms, right? We were just, some kids on the internet, they don’t, they didn’t know anything about us. We want a trusted company, but

Andrew: Where were you living at the time because you were outside of, You were outside of Silicon Valley. One of the things that I know was eventually Heat and Shaw, who is one of like the main people within that community cuz he helped everyone. He installed your software on Dave McClure’s computer. That’s like gutsy for him to do that on someone’s computer.

But he would, You got an entry through people who are in, Where were

Aye: We were in Boston, Heaton was also in Boston, and we were part of the Boston started community. Yeah, we came outta mit. So we have connections to just, you know, Boston Tech from there.

Andrew: Okay. How’d you

Aye: one of this like Boston Mess in No Night, one of those litter startup events and we were basically going, showing up and showing what we built to people. I remember like taking buses to get to, you know, some suburb.

Andrew: Ooh.

Aye: Suburb of Boston with our own little laptops and like, we didn’t have any like, you know, money to be like sponsoring the event or anything.

We just show up as, uh, attendees and then we bring up our laptop and like, Hey, can I show you something I’m building? And that’s Mm-hmm.

Andrew: to host events like that and I loved it. You’d get some random people who, who were completely clueless and going nowhere, but you’d also get some random people who had a clue into some insight in the future or how things should be, and they ended up going to spectacular heights. Okay, so you did this.

People were interested. At what point did

Aye: So that was a little bit later, about 11 months after we launch that, we started thinking about just monetization in a. . So as even farther back, it’s kind of interesting. We released as a free product, right? We just won it. It was, it went viral, right? And we had like friend page of dig at the time that matter.

Right? Right Now nobody goes to dig. But it was friend page of dig. Um, we got on, so

Andrew: Reddit, uh, site. Yeah. Where people get to vote and it’s all one group of people vote. It’s everyone voting on the same

Aye: So we got probably hundreds of thousands of install and people started using it and we started, started getting requests from customers asking for a PayPal button to donate money to us. and we were like, Wow. Like this is, uh, you know, all real value at the time. We just build it, we get users, we will see where it goes, and now we are starting to see that there is real, you know, monetary value that people are willing to contribute to keep the project running.

Right. And we call it a voluntary subscription instead of donation. Cuz we didn’t want, we are like, okay, this is a business, we don’t want you to just think of us a few kids, you know, hacking around. We wanna be taken seriously. So let’s call it voluntary subscription. We put a PayPal button where they can type in whatever they want, amount that they want to pay, and we call it, It’s a voluntary subscription when we start charging for it.

Whatever you pay here will get you one year of subscription and because we maybe. Primed it as subscription people started giving us in multiples of 12. So some people pay $12, some people pay 24 36. The highest was one 20, right? So this, these are people who have no reason to pay us. It’s free product.

It’s out there. We’re just building it. And they decided that. , this is worth 120 to me. So that’s where we started to get the confidence to start charging. I call up everybody, um, all the heavier users. I call up people who wear. You know, paying as voluntarily. Do you just kind of talk through what’s the value you’re getting?

How, like if we start charging for it, how much would you pay? Would it be on your company card? Would it be on your personal card? Right. All kinds of interesting, uh, pricing questions. And half the people are like, Oh, if you start charging, I’m not gonna. and you know, your, your company will die if you start charging.

I was like, Well, if you, if we don’t charge, our company will die too. Right. So that’s after about, I think, I think I made between 50 to a hundred calls and we kind of started to set up the subscription levels and we show it to one of our investors and he asked me this. And I still remember the moment where he’s like, Mo, are you comfortable paying these prices?

I was like, Yes. You know, this is what I would pay if I, Because we were using it too, right? And we build a product because we wanted to use it. And as users, I was comfortable paying these prices. And he’s like, Then you’re not charging enough. He’s like, Founders tend to make the mistake. and they’re charging for their products, especially founders who use their own products.

So he’s like triple it. So we actually did, we went from like, not quite triple, but he’s like, What would you be willing to pay, but not that comfortable and kind of grumble about it. . So we set the price to the $5 and 15 a month, 15 a month for software at the time was a lot and. I was like, Yeah, I would pay 15.

It would, you know, it would be like doable, but not happy about it. And he’s like, That’s the right price. Uh, Manu

Andrew: is this

Aye: with Canine Ventures, so he’s in Lyft and a few other Trilio, a bunch of awesome places.

Andrew: Let’s talk about your investment. In fact, I should first say my sponsor is Lemon. Anyone out there who needs to hire phenomenal developers, you should know that the founder of Lemon started out by, by finding Ukrainian developers for his friends who all said, Oh, you’re Ukrainian. Can you introduce me to Ukrainians?

They knew Ukrainians are phenomenal developers and we’ve actually discovered that now, uh, because of the war. Um, how many people in our space are from Ukraine and are now dislocated or out fighting. Anyway, he discovered that and he said, Sure, I’ll make matches. He started making matches as a favor and as a friend, and then he said, You know, there’s a business in here.

There’s so many people asking for matches. I will do it. I will vet the people for them. I will be the intermediary and I will make sure that they could hire phenomenal developers. Unfortunately, because of the war. A lot of those developers are either outside of the country or had to go in and to battle.

And so he said, I need to stretch my company beyond this in order to survive, in order to take care of the Ukrainians who work for me, which he decided that he would continue to pay for them, whether or not they could continue to work. So he said, I’m gonna expand. And it forced him to expand beyond Ukraine to other countries where developers are phenomenal, where people have a hard time accessing those developers.

And by the. The prices are reasonable and because of the way that he works it, he’s not saying, Here’s a message board, go and find them. Or, Here’s a job board. Go and find them. He’s saying, I, my team and I will help you find the right match, the right developer. We’ll make sure the price is good. We’ll make sure the developer’s fantastic.

And if you use my url, mine, Andrew Warners url, you’re going to yes, help me show him that I’m a good friend who can help him get more, more customers, but also you’ll get a better discount than other people. All you have to do is go to g. Do I have to spell lemon? No, i x e r g y.

All right, thanks, Lemon. All right. Let’s talk about develop, uh, fi financing. At what point did you decide we need to raise

Aye: Um, we were raising money right before we started charging, even before we started charging, cuz we were, you know, towards the end of the, our credit card and . We didn’t come from money.

Andrew: How much debt did you have on your card?

Aye: how, if we got into too much, I think about 4,000. Because what happened is

Andrew: Oh, that’s not too bad. Yeah.

Aye: Alex and I, were outta mit.

We were working at big companies. I am international student with student loans at, you know, astronomical rates because I didn’t have a federal, you know, loans or co-sponsors or anything like that. Right? So basically I had. International students and secure loans and we have to pay off those, um, and basically set ourself up as you know, adult, pro, young adult professionals.

So we work for about five, six years outta college. And from those savings we were able to pay off the student loans right. And build up enough cushion to be able to, uh, start this without a full time job. And original plan was Alex was, um, gonna go do a full time and I’m gonna stay at my full time job so that we have somebody paying the rent

And we did. And we move out to like, you know, way out into the boonies. Uh, Boston so that our rent was cut in half. All kinds of things that we did to basically make sure that we can go a little bit longer without salaries. And then we were trying to raise funding in Boston. We were striking out mainly because.

What we were trying to build was, as you said, nobody knew you could make money from, you know, email productivity and especially built on top of, uh, somebody’s platform like Gmail. So we pitched probably like 30, 40 investors, strike out on every single one of them. And then we, by happenstance, we were in Silicon Valley for about a few days between two weddings and.

We got a, we saw a tweet from Dave McClure asking for a ride because his car was in the shop and we went from the Silicon Valley. So he just said, Bucks. He’s like, If somebody comes pick me up at Bucks, I will, you know, let you pitch me on the W uh, his car dealership. So it wasn’t to the airport. It was actually to the dealership, and he.

When he tweeted it, I was like, Okay, we’ll do it. We were, you know, staying in this terrible motel in Sunnyvale or Santa Clara called Sun Downer Inn. Even the name was kind of depressing and we were supposed to go see a VC that. Uh, Alex knew from his fraternity and that VC cancel canceled the meeting. So we were just like depressed in a depressing hotel room.

Saw the tweet. We were like, Nothing to lose. Let’s do this. And he, I asked Dave McClure, Hey, like, What’s Bucks ? So apparently there’s a place in, um, where’s the town?

Andrew: forget

Aye: Isn’t near Melo Park. Yeah. And where all the dcs hang out apparently. So he is like, Oh no, no bucks in this town. And we are like, Okay, well look it up. And I was like, and we didn’t really have, you know, great GPS in the cars and stuff. So I was like, Okay, you drive, I’ll stay in the hotel room and tell you where to go and give you the direction. Yes,

Andrew: really?

Aye: So

Andrew: Okay.

Aye: he drove up even without knowing exactly where he just started driving up 1 0 1. And then I gave him directions and I was coordinating Dave. And the main thing that stories that people didn’t really know the layers of is Dave has this thesis about he needs three signal points before he makes a yes position.

And we. We’re already talking to him through. Connection that was, we got from Boston and we were supposed to schedule a meeting with him and he’s, you know, very hard to schedule. So we all, Oh yeah, so and so already introduce us. So I was just kind of, you know, making sure that he knows well who we are.

And then his assistant, his personal assistant, was using Boomerang and the Heaton also. and he’s like, Oh, oh, you know, somebody else is doing this. And we are like, Yes. And he’s like, Hitton told me about this company that’s doing this. And we are like, Yes, that’s us. So that’s the three signals that he needed.

So it didn’t sound, it sounded a lot more random if you just tell a stranger, pick him up on the right and he wrote a hundred k check. But it is kind of funny that way.

Andrew: And the idea is you pitch him on the ride. He, and he wasn’t necessarily thinking of closing the deal. I thought, I guess because of the way that it ki it came out, it was pitch me and then maybe by the end you get a hundred thousand, which I always wondered about. And now I understand. It’s more like, yes, you pitch me, but I’m

Aye: Just because you did it. Yeah. It’s not, He will, he will listen to the pitch.

Andrew: But if there are more signals,

Aye: Yeah.

Andrew: Okay. And so now I’m seeing the different signals as they come about. I see how that worked out. Where did the other money come from?

Aye: He was the first

Andrew: He was the first.

Aye: he was the first check in. And then because he was in, he introduced us to more people. And then also we got introduction from Boston Techstar crew, because we were part of Techstar Boston. So yeah, so that’s partly. That’s where all the money come from is different. Uh, and almost all of them are angel investors.

Aside from um, Dave and Manu Kuma, who is Seed Fund. So Manu was,

Andrew: Did Dave do it out of his own money or Out of 500

Aye: 500 startup

Andrew: uh, investment firm.

Aye: Yeah. We were like one of the very, very earlier stages of five hundred’s startup.

Andrew: All right. You still own the domain Baden? That was the original name. It redirects though to boomerang At what point did you say we are going all in on email?

Aye: exactly remember. It was probably some marketing director that we hires. Like, we need to consolidate the brands. And figured out how, how to tell the story. So,

Andrew: Was, Was it also the investors who said, Stop doing everything else. Get your eyes off of the other products. You hit it with email. It’s a big enough market. Every single person, literally everyone online is gonna have email. Just

Aye: No, they, they’ve been telling us to focus forever and

Andrew: So then why’d you finally

Aye: because GMO started copying some of our stuff in 2018 and we started to kind of like think about. What are we going to do as a company? Are we going to become this and pay research love for big companies forever and trying out all the things and you know, when things work they copy and things that didn’t work just kind of float around.

So 2018 when Gmail started copying, we kind of have this come to Jesus moment. What do we want for our company? How do we want to move forward? And that’s when we decided, okay, we gotta kill off things like the email game and a few other, you know, smaller things that are out there that’s, they don’t generate revenue, they create distraction, they create it a lot of, you know, basically maintenance and support headache for everybody.

So we killed. Four products I believe, and some of them are not killed of. They actually got folded into the mainline Boomerang product,

Andrew: What was, I forget what email game was. Um, I remember it was just like, can you do something within a certain amount of time? But I

Aye: The concept was mostly, um, you see one email at a time and you have to make a decision on whether you want to archive it in the sense that like, I’ll need it later, delete it, I don’t need it. Uh, bring it back when I need it or respond. So each of these actions get some points, and if you skip it, Negative points because you’re not making a decision and you’re not clearing out the inbox.

So it’s the clearing your inbox game and we have timers to kind of keep you moving and, you know, not get too bogged down and trying to like craft the perfect response, which we tend to get. Um, so that’s, that was the original idea. Um, and I. Some of these ideas live in, you know, currently popular other products like Superhuman where they show you one email at a time and auto events, do the next email and you know, you have all these options to how to handle it.

But I think the timer and like the gamification of, we turn the screen red if you’re taking too long. I think those were a little bit too much and people, people reported, Oh, you’re, you know, creating anxiety for me. So we have to tone down some of it. And I wish we had more

Andrew: It was one of those things. Sorry, what? You wish you had more? What?

Aye: keep. More develop and you know, invest more in it. We just didn’t have the team to do it.

Andrew: Um, I’m looking at a mug that you’ve made to try to make money off of the email game. It was like in the frequently asked questions, Do you like the email game? If you do buy a mug, and the mug was email like a. A designed picture of a sad looking, angry looking email with a pitchfork, and the words underneath would say, Who’s afraid of a big bad inbox?

And on the back it’s email game, the domain that’s on there. So you, you really were just kind of all over the place trying a bunch of different things, seeing what worked and what ding. You even had something called like revive inbox, which was basically a 21 day email drip campaign, I think,

Aye: We still have it and it’s still alive.

Andrew: just wanna learn how to

Aye: we just need to update the content a little bit. And it is, it’s kind of like changing your inbox philosophy. Like it’s like, you know, going on this like journey from, you kind of deal with your inbox in a way that’s not very, Structure, philosophy or structure, methodology on how to deal with it to like, when you come out of that program, you’ll have, This is how I deal with email and you have a sustainable practice.

That’s what we were trying to do, but mostly as a content marketing. We were trying to do . Yeah.

Andrew: Right, it was, There are people who don’t wanna sign up for new software. They just wanna learn a methodology. We’re gonna teach them a methodology via email drip campaign. And by the way, this was created this whole drip campaign

Aye: And then there are like parts of the content where we show them like, Hey, you can snooze email and if you’re in Gmail Outlook you can use ours. If you’re somewhere else, then you can, you know, kind of hack around this way. So it’s mostly a marketing tool at the beginning. And then the content we got really into it and like the content was pretty incredible.

Andrew: Let’s talk about some of the, some of the marketing that worked for you in the beginning though, if, uh, if I remember right, first of all, we talked about this content marketing revive your inbox with a whole standalone site, and it worked. It’s what we used to call microsite. The email game would feed people into Boomerang, which was your paid program.

You did some marketing with things like the life hacking bloggers that helped you. You also, if I remember right, would have on the emails that would go out, a message that said, Sent with Boomerang or something like that, right? So you had the original form of viral marketing, the one that was created back in the old Hotmail days, incorporated

Aye: did it for the, our, um, mobile apps. Mobile apps. One you’re sending from Boomerang apps. We say send with, I think we said type with. Type with thumbs and send with love from Boomerang or something? Yeah. We’re just being cheeky and

Andrew: Ah, okay,

Aye: not from the web. We never did it. We never did it. Um, for some, I think mainly because we wouldn’t like it ourself and we try to like kind of have very high empathy for the users and what we would like, what we don’t like.

So same thing with rere. Receive when you want to track somebody, whether they open your email or not, we make sure that there’s a way for you to opt out as a recipient. So that’s one of the major philosophy,

Andrew: Okay. So then what did work for you in the early days? I wanna go back to like when things were easier to see what worked and then go into what

Aye: uh, things that really work was, um, content. That comes from data analysis. So that’s one major thing that we had as a free million free trial too, is we have a lot of data people, you know, we are probably about,

Andrew: Hmm.

Aye: don’t know how many, half a billion messages scheduled by now, right? Like so. We have a lot of data on when people schedule emails, When people, uh, want to bring back email, what kind of emails do they track?

Uh, out of the emails that they track, what percentage of them get a response? That kind of data is nobody else has it. So we had a data science, um, Guy who basically is writing out blog posts from looking at dataset and some of the dataset weren’t even our own dataset. We would look up like email dataset that’s publicly accessible like Aron and crunch data on it to be like, Hey, what’s the best kind of.

Email greetings, right? Do you start with hi or hello and how does that impact your response rate? So that really work. We got on like Good Morning America, bbc, right? Cnn, because this is a evergreen content. Everybody wants to know about how to write better emails, how to, how to optimize your email. For better.

It’s just people general interest, right? It’s not so eso. And anybody who has email, kind of like, Oh, this is interesting. So that generated a lot of boat traffic and interest for the product.

Andrew: This was because Enron’s email was public and you decided we’re going to analyze it while people are talking about it and help understand which of their email was open and which one wasn’t, and like which one was open, which one wasn’t. How did the higher ups respond, send messages, That kind of

Aye: Well, it was way after Aron’s scandal broke out. Mainly because they were public and it was easy to get data on for the email body. Cause our privacy policy, we try to not use our customer’s data for their email body unless they like it’s completely anonymized and we were just ma Sure. That. There’s no self selection going on.

Um, and if you use like public data sets, you just kind of get a little bit more of everything. So we were just kinda like, Hey, what can we crunch from all these data sets that are out there and tell a story? So is storytelling, data analysis, finding insight that nobody has before, and a little bit of researchy bent to it, right?

We wanna know what. What, what are the things that change? Email’s. Effectiveness.

Andrew: Okay, so now that I see that, let’s. About some of the things that were copied. You told me about the first feature that Google

Aye: Uh, they started copying Snoop first and then they copied Send later.

Andrew: And then when that happened, those were two of the key parts of your software. What happened to your customers when they created this

Aye: uh, the main thing that happened is, uh, it affected our growth. Uh, basically kind of, you know, make it so that when people are looking for those things before we own that SEO and everything else, and just by boat, you know, wore the mouse slash. SEO of everybody who’s looking for these solutions found us now when they needed, they either don’t even go look for it because Google already has it in there.

Or when they go look for it, Google send them to their own things because they own also Google search engine. So it mainly impacted our, um, Growth from the casual users. So the professional users, people who are super power users are still paying us and still finding us because even for those things, we do it much better because we didn’t build it just for, you know, general public.

We build it for people who needed it as in a a little bit more focused direction.

Andrew: What did they need that wasn’t available through Google’s system?

Aye: right now, Um, the main thing is the response tracking. So if I send you an email and if I don’t get a response, I wanna be reminded that part is still, you know, we did it from, I don’t know, 20 11, 20 12. So it’s still the major part of what you need.

Andrew: Got it. So heavy users are not looking for every message to be snooze. They just want the ones that don’t get a response back to come back in their inbox. So they notice A, Did you get a chance to look at this? Or, This is urgent,

Aye: exactly. And then we also, if you’re like snoozing a lot of emails, you want the menu to be customized to exactly how you use it. So like I have a Monday morning at 9:00 AM as this customized thing. I also have things that I need in the weekend for Saturday. You know, 3:00 PM So like the menu customization.

If you’re a super power user, there are things that you want. And like we can actually, you can actually type in Monday at 3:00 PM Eastern Time and it will just figure out what time it is and make it, you know, go to the right time. So that kind of extra like lit bit of professionalism that you don’t get from the main Gmail menu.

Andrew: Okay. And so at that point you said we have to start focusing because there’s competition coming into this space and. We have to see what makes us better And what makes us better is we have much more power users, uh, features for power users. That’s the thing that makes us better. Um, and then when the number of customers who are coming in slow down, what did you do to combat that?

Aye: so 2019, I actually took a year off from Boomerang. We were just burned out and you know, we’ve been working on this for eight, nine years by then. Um, so I took the whole year off just to kind of figure out what we wanted to do next. Uh, I travel a lot. I went and. Became a VC advisor for about two months.

I did productivity consulting and I helped people figure out their workflow, just tinkering around to see what we were gonna do. And because I was doing like, you know, angel investing, so I was meeting founders and because I was meeting so many people, I was scheduling a lot of meetings and I was trying out call Lee and a few other tools.

And nothing was quite right. I was like, Why can’t we fix this problem? Like this is a problem that you know, remains to be solved even with like popular tools that are out there. And I think the push comes from the fact that I’m kind of like, , slightly lazy in the sense that like, I don’t want to do all the work to schedule a meeting and like, and also have a very high standard of user experience.

So I was like, You know what? We could fix this because we have this technology that we have patented that is a live image generation within your email for a long time. Why don’t we use that to bring this life image? Of your schedule that consulted from your Google calendar and put it in your email and the other person can see the time.

I don’t have to click through to find what time you’re available. Scrolling through different calendars and then typing in your names and emails. All of this is like general inconvenience for both parties. Why don’t I just put it right there in the email where you don’t ever have to. And make this flawless.

So I kind of started to,

Andrew: And make it, make it more customized to the individual you’re sending it to, because I might have a need to talk to you tomorrow and sending you my calendarly link with all five days worth of like e, every weekday worth of availability. It’s a mistake because you might pick next week, but I wanna talk to you tomorrow and just show you that.

Or I might want you to have more options than other people and I’m not gonna create another Count Lee link just for you so that you have it right. And then Outlook was enabling that. The problem with Outlooks version of that was if a meeting was booked by someone else at the time, you just sent a person.

That person would still be able to book that meeting. It wasn’t aware of who else booked, right? Who was on the

Aye: Yeah, so we wanna make sure that there’s no double booking. There is a lot of, you know, customization and personalization features that we want, where time zones, we actually are able to show the times in two time zone, three time, two time zone that are across from each other and put it right there so you can kind of see.

And then, yeah, basically we ba we build it so that. If you want super customizable, you can say, I want to give you this five times, and then those are the five times that you get and you can click it and it, it is all done. Or if I want to be more flexible, then I can do the currently type of rolling and availability where the image just slide to whenever you opened it.

Right? So if I send it to you today, but you are off on your honeymoon and you came back two months. the image, it’s still live. So there are a lot of things that we wanted to kind of handle it just so, and I started pushing our attack team to be like, Can we do this? Can we do this? Let’s figure it out. And then we built it and I started using it and I was like, This is it.

This is, this is the, this is the way people need to schedule their meetings. And like that’s what the next decade should be. This is how people should think about scheduling. For the na, like it’s kind of like snooze, right? Like, but, but there’s the priest news and post news era. I was like, this is the nice thing.

Andrew: And that’s what

Aye: That’s why I came back and

Andrew: that you started to see a need and you said, Okay, I’m excited, invigorated by this. It’s not just improving email a little at a time. It’s a whole new, Okay, let me say this. Anyone who’s listening to this, you’ve been hearing about email marketing from the recipient point of view, let’s talk about it from the center’s point of view.

Because one of the best ways to reach people is through email marketing and there are tons of software out there for email marketing. Why am I suggesting that you use Send in Blue? Let me say that slowly. They’re the sponsor Send in Blue, because what Sendin Blue does is they have all the smart automation features that you’re looking for.

They also will integrate with sms. I have to say to you, Mo, I talked to guests about Sendin Blue and I, and I say, Is it something you use or not? I had this one guest say I use it, but oh, I would use it, yes, but we get more traction from sms, from text messaging. This ends included. They will do text messaging, they will do chat communication.

They will do automation. They’ll do all the things you’re expecting, and then some. What they won’t do is give you a low teaser price and then jack the price on you later. But what they won’t do is make it too complicated to use that. You’ll say, This is a good feature when you sign up, but a year later say, Why don’t we ever use that feature?

We must not be doing something right. We must be at fault. No, it’s not you at fault. It’s the other software that makes it too difficult. So you don’t use it. All right. If you wanna get started, I’m gonna give you a, a discount on their already low prices. All you have to do is go to send in g send in

G by the way, had the, the business do mo in the year that you took off.

Aye: It was okay. We basically kind of, you know, continued to support our current features and then we were building something called Boomerang Insights, which is kind of like personalized report on your email habits and insights that. Like improve your email game, right? So it will tell you like, Hey, you tend to check email 20 times a day.

Here are the times that you do check, uh, this is how you can get better focused time, that kind of stuff.

Andrew: Okay, and so they were working on that. I’m assuming that growth was maybe not going to, was growth just flat or was it still continuing?

Aye: was so continuing. It was continuing, but like not, not at the rate that we had before. And then we also didn’t spend any marketing, right. We were basically cut it to, to spend minimum.

Andrew: Okay. And so then when the business was on autopilot, that’s where it was, you come back in. How long did it take you to, to get this new, um, scheduling feature

Aye: a year, a little bit over a year, and then we did it in three phases. We started with the suggest time, which is, you know, ability to offer specific times to people. Like I pick Monday at two, Tuesday at five, Wednesday at three, and then you put it into a email, they send it off. And that has a little bit of higher startup costs, as in like as a sender, you have to choose the individual time and send it.

and then we have share Free Busy, which is just like I am pretty open book, especially people like who they’re in sales or outbound facings, they don’t care when you want to call them, right? So they just give like, Here’s my availability nine to five. Whenever I’m free, just call me. Uh, so that’s on the, I am a kind of a control freak, so I don’t use that feature as.

and then, so those two were a little bit easier to build, so we got them out. And then the last part is the newest one that we just launched this April called Bookable, which is you set up a schedule and then the image is a sliding window of your availability to whatever time you are looking at. And I think that’s like the

Andrew: Oh, and the image is a screenshot from the calendar. Minus what’s, what’s there? Just the

Aye: availability. And then you can book directly from the image. And depending on when you are looking at the image is refreshing so that you are never double book. So that part was a little bit harder to build. And we did pretty interesting technical work. Basically like we build a matrix and mapping, image mapping in the matrix to.

Andrew: Oh

Aye: kind of know which, uh, click you, which, you know, grid you were clicking and what time it correspond to, so,

Andrew: Because images on HTML images have always allowed you to have what they, I guess it’s called, uh, mapping, where each pixel essentially could have its own url, and that’s what you’ve created for each individual email updated in real time whenever the person checks the message.

Aye: that’s, and the harder part is like making it work across all email platforms, right? You’re sending it from Gmail, but they’re opening an Outlook. We wanna make sure that it renders and it behave correctly. We have an Outlook product where they send it from Outlook. It should still work in everywhere else.

And then the next part, the next step. Of the product roadmap is making sure that if your a user is sending a image from the, your availability from Gmail and you are opening it in a different place, your ability to overlay your own schedule without even leaving your

Andrew: Uh, yeah.

Aye: I think there is a major advantage being a third party middleman because we are integrating with each of different platforms, APIs, and optimizing the experience for everybody rather than, Hey, if you’re in this ecosystem, we optimize it and make it good for you, which is what, you know, major platforms tend to do and but our target customer profile.

If you’re using this, you’re typically a externally facing person in your organization, right? Because if you’re somebody who’s just scheduling meetings with your own team, you probably just use Outlook or Google Calendar or pull it up their schedule and you know when they are available. It’s the, for the people who are talking to people like you, right?

You’re talking to multiple guests. They are from different organization. You don’t control what calendar they use, and they are not going to share their calendar availability with you. So this is basically externally facing people and for them, this interoperability for any platform, any email client you use is really, I.

Andrew: What do you make of the fact that Count Lee now is, at least according to a Tech Crunch article from last year, it’s worth 3 billion from this one feature that doesn’t have the flexibility, Is it that it’s just easier to use and it’s made for the mass public versus yours, which requires a little bit of thought?

Is it that it’s got, I don’t know, uh, a head start on others? Do you think that there, Yeah. What do you

Aye: I don’t think we, ours is, uh, require more thought to use. It’s just that ours is something nobody’s ever seen before. So it does seems like more sophisticated, but like one, you actually count the number of clicks and number of things that you have to do to use it. It’s actually a. I think they’re just, you know, they have a hashtag start and they have a great sales team, right?

And they have great, great

Andrew: But their free is also a good sales team, right? You use their free, and then you’re telling other people about Calendly with the free, And then by the way,

Aye: Yeah. Moving scheduling itself

Andrew: might sign up,

Aye: the product itself is like viral by just in. Build in virality for, because you’re meeting with people and it’s usually across organizations, right? So it is not just like you’re meeting with your own team, it’s going from one organization to another.

I think they just are really well run se business.

Andrew: Well, you also have a free version. It’s available at Boomerang. it’s, It’s on boomerang But then when I go into one of the links, I’m in Boomerang for Gmail maybe, because that’s what I have is Gmail. Uh, Gmail. But you also have a free version that goes out. You don’t promote it in the free version, right?

I don’t know that people will know that this comes from

Aye: Uh, it is, it has the bar, the, we have, we now have like links for, like, this is coming from Boomerang now. Um,

Andrew: It is. Okay.

Aye: And then when you go to the landing page, you will see like this is, you know, you’re booking through Boomerang and then meeting events and stuff. All have like coming from Boomerang,

Andrew: All right. I gotta close out with a personal observation. So I’ve watched a bunch of videos of. . You have these beautiful dresses that have the Boomerang logo on them. I didn’t expect you to come in today in a business suit. That looks great. That also has the Boomerang logo on it. Everyone else has a T-shirt or something else.

Tell me about this. This is intentional. You have somebody embroider your clothes, don’t you? You buy Highend clothes and then you embroider it.

Aye: you know, like people talk about how Steve Jo wear the same thing, and I decided that any kinds of professional engagement, I don’t want to worry about what I’m gonna wear and spend my brain cycles on it so that I can focus on the conversation, right? So this morning I was rushing to get the two kids out the door and then I can kind of like take a pause to think about what we’re gonna talk about, but I don’t have to think about what I’m gonna wear.

So, Uh, and I have,

Andrew: Wait, but it’s not always the same. I’ve seen you do it. I thought maybe it was, it’s not. It’s different, but you know, I have a set of clothes. They all look professional. They don’t look like I’m wearing a t-shirt or the polo shirt that a lot of people have with their logo on it. , it’s gonna look good, but it will still have our logo on it so that I’m representing the brand even in photos.

So if Andrew’s just doing a quick search for my photo to see what I’m gonna look like today, he’s gonna see the logo

Aye: We basically, did that mostly out of like, I don’t know, we we’re kind of quirky. We do a lot of weird things as a company. I can, I can talk about all the crazy things that we do, but this is one of the things we have, uh, button down, like long sleeve button downs for men with embroid shirts of so that they can, you know, go up.

So I have two or three dresses all brighter and then this jacket I can just throw on anything and be ready,

Andrew: All right, . Well, congratulations on your success and your refound enthusiasm for the business. I’ve been watching you for years and I’m gonna continue to follow you. And I think the big lesson that I took from this was that the competition from the bigger guys is not, obviously, it’s not great, It’d be better if Gmail had none of these features and you had a monopoly on the features, but, Barring that.

The next best is to know that this is being introduced to people who then say, I need more of this. I, I now see that snooze is a clear part of email engagement for professionals, but I have deeper need. And Boomerang is gonna do this for me. I have, so these professionals are saying to themselves, I understand that I can get a calendar service with a, with a a page, but I have deeper needs for more granular interaction with people and customization.

And Boomerang is going to do that. And that feels like an interesting playbook that I can take away from this conversation.

Aye: we have this kind of deeper insight into what customers are doing and what they need. Because we talk to them constantly. We have great relationship with them. I have a funny story. So we are raising our prices for the first time in 11 years, and we send out the email saying, Hey everybody, we are raising our prices and you know, to lock in your old price, we have this.

Button you can click and lock in your old price for one more year. And we have many, many supportive customers emailing in saying, Hey, yes, you guys should raise your prices. I’m a business owner. I know you know what? These times are happily locking in for the. next year. And then there are people who are like, I’m actually not locking in because I’m willing to pay the extra price for you so that you’ll have more revenue sooner,

And it’s like the most heartwarming type of support that you can, you know, imagine, right? Because we’re, we’re scrappy tiny company that focuses on our customer needs and what we can do for them in their daily lives. Saving time. And they know that they respond to it.

Andrew: There is something very warm about a group of customers who can say, I want you to keep going because you’re helping me. And the internet has been really good about bringing that out, and I felt like maybe that’s just behind us because now it’s all much more transactional. But you’re reminding me that’s true.

And you increase your prices recently, and you told me the reaction before we started. You told me the reaction was.

Aye: We have, you know, way lower than expected rate cancellation way more of like, like just the emails that are coming in. We expect it, like there will be a few grumpy people, you know. Uh, Kind of mad about price increase, which is normal with any consumer product, and we did not get any negative feedback and all the feedback’s been like, It’s about time, or I’m in support.

I am with you. So I think I’m gonna write a long blog post on how we approach this and what type of email bodies though we tested, we tested two. That we send to kind of test a sentiment. And the first one was just like straight a businessy. You know, we look at how select did their price increase and pretty much copy that type of message.

And then the next one was like very personable. Hey, we, you know, be been building this for 11 years. We never raised their prices. Here are the things that we have built and. With their revenue and the support. These are the things that we’ve been able to accomplish, some of which includes like building schools in Burma, right?

We donate a, a proceeds of our profit to build schools in Burer, uh, build help with the kind of column captured labs. Academic research lab working on Calvin Capture. So like we basically tell the customers what their support and you know, subscriptions are able to. Create and then we sent a picture of the team with, you know, basically we recreated the picture that we sent originally 11 years ago with just now a slightly bigger team and a different message we sent.

So original pictures that will coat for food, which was like, Hey, we. We need to charge for this, for us to eat. Right now we are like still coding. Still eating . Thank you. And people, I think people really respond to that type of personal connection with the team.

Andrew: Yeah. Yeah. All right. I certainly have, I mean, I’ve really connected with you and your team over the years, and it’s fun to actually get a chance. As soon as I heard that I had a chance to interview, I said, Yes. I wanna find out what happened. I wanna find out how they’ve been doing this, how they’ve been growing, and I’m glad I’ve gotten to know you here through this interview.

For anyone who’s interested, it’s boomerang And of course, I wanna thank my two sponsors. The first, if you need to hire developers, go to And the second, when you’re. To do email marketing and everybody’s always ready to do email marketing, so that’s a trick question. Now that you’re ready, I should say, to do email marketing, go to send in g mo Thanks so much for being on here.

Aye: Bye

Andrew: Cool. Bye everyone.


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