I'm Aye Moah, CEO and Co-founder of Boomerang. AMA about building a profitable, bootstrapped category-creating company

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Hi folks,

I’m Aye Moah, CEO and Co-founder of Boomerang. We created the email productivity extension as a SaaS product category back in 2010.

We invented the concept of snoozing a message and made it so dead simple to use that the concept caught on fire. Now the concept of snoozing a message you don’t want to handle right away is accessible to billions of people in every email app, as well as various tech products ranging from Slack to Trello.

We’ve grown to multiple million ARR since then and we have only taken in $400k total of funding. Our last funding round was back in 2011 and we have grown with our customer revenue. So I’d say we can be grouped under bootstrapped companies essentially.

I stepped into the CEO role just last summer after a decade of serving as the CPO and Co-founder. We are one of the rare companies that still have all three original co-founders still working together after all this time.

In 2018, as monopolistic big tech companies are wont to do, Google started “incorporating” snooze and scheduled send features into Gmail natively. Then Outlook followed their example a year later. We were worried about the impact and feared for the worst. We preemptively laid off two-thirds of our team to improve cash flow and brace for the impact. It was a very hard decision that ended up being too pessimistic. It turned out that Google and Microsoft building worse versions of our products had much less impact on our revenue than we feared.

I personally took 2019 and 2020 off from working on Boomerang full time. I was burned out after 8 years as a startup founder and wanted to figure out what’s next for me. Most of 2019, I spent traveling. Late 2019, I started to do some angel investing and also offer productivity consulting to some folks just for fun.

When I was meeting many founders and consulting clients, I kept running into the age-old problem of meeting scheduling being inefficient and tedious all around. That led me to agitating internally to tackle the meeting scheduling problems with the unique technology we already have around live image generation inside an email from calendar schedules. But we made sure we had some patents filed this time around.

As we were building it, the beta product got me personally re-energized to take on the challenge of growing Boomerang to be the best solution for meeting scheduling. So I came back to work full time in the middle of the pandemic and a few months later, we did a leadership change with me taking over as the CEO.

Our company DNA has always been about product innovation and pushing the boundary of technology to make our users’ lives easier. I think that part will remain the same but some things will be different as we enter the next phase of our company.

Topics that I’d love to talk about

  • What’s it like to be a category creator in SaaS
  • Decision making frameworks around product development
  • Product led growth
  • How we build a multi-million ARR business with very little funding
  • Advantages and disadvantages of not raising funding
  • How to keep innovating even as the company grows
  • What worked well for our team when we went remote overnight
  • Co-founder relationship, especially as a couple co-founder
  • Personal productivity optimization
  • Why sending a Calendly link is rude
  • Why we build schools in Burma and donate to academic labs working on climate change
  • Reading 50 books a year for almost a decade, my gardening misadventures and Burmese food

I’ll be back on March 31st at 10:00AM PST to answer your questions! Looking forward to the discussions and thank you to the Relay team for inviting me!

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Note: This AMA is closed for questions, but you can check out the existing conversations below.

This March 31st, we’re really looking forward to hosting Boomerang’s co-founder and CEO, Aye Moah. From their principled stance on building software that respects the whole ecosystem of users even when it translates to lesser revenue, to their understated, shake-your-head-in-wonder influence on emails over the past decade, and a founding commitment to give back to the world, Aye Moah and team have built a unique business that serves millions of active users (from folks at Square, Twilio, and high-school principals), profitably and sustainably.

AMA Index (Aye Moah’s brain-pickings) :brain:

(Hard-won insights, opinions, and observations; thoughtfully examined and articulated)

— Some deliberately calm, team-wide productivity and comms routines
— On raising a modest seed round
— Considerations on transitioning from browser extensions to standalone products
— Starting out in 2010 and getting off the fundraising treadmill
— What inspired Boomerang’s giving back principle; “I felt very strongly that it’s important to pay it forward for the next generation”
— Kicking off price testing with voluntary subscriptions
— Choosing to be a small, elite team and taking a year-long break as a founder
— Reimagining their trajectory after making the hardest decision a founder can make
— Some qualities and traits of the “small, elite” Boomerang team
— Moah’s reading philosophy and some recommended titles

Further reading/listening/pondering from the interwebz :open_book:/:headphones:

(Other insightful excerpts drawn from blog posts, interviews, and conversations)

On choosing to be customer-funded:

We really focus on the ability to get value out of what we provide as a service to our customers. We knew that we wanted to grow from our own revenue and profits.

It takes longer, right? It’s not explosive growth because we’re not able to spend on unprofitable growth. We focus only on sustainable marketing channels that bring in more money than we spend.

But at the same time, it makes us very focussed. As a customer we only work on things that will bring value to our customers. Because they fund us and guide us through what to do next.

With investors, we’ve been really lucky. A lot of them are our personal friends and personal champions to us and mentors and advisors in addition to being investors. And they’ve been very patient with us.

But the good part is, we were able to issue our dividends and we’ve already issued more than what they had invested in the company just as a dividend. The beauty is that they get dividends and they still own equity in our company as we’re growing. So it’s a pretty happy relationship.

Source: Fund BMC | 2020

On taking an ethical stand with product decisions:

There are some parts of the product decisions that we intentionally chose not to take, even though they certainly will bring more revenue. Because we don’t agree with the damage it would do to the email ecosystem.

For a very specific example, we have a feature called ‘read receipt.’ Which is, when I send you an email, I want to know if you read it or not. A lot of the email productivity companies implemented it as an invisible pixel in your email.

So as a reader of the email you don’t know that you’re being tracked. As a sender, I know exactly when someone opened the email, down to the second, which device, and what location. We don’t believe that that’s information that the sender should have access to.

Just because you’ve sent me an email, I don’t believe you have the right to know where I am and what device I’m using. So we basically implemented it so that as a reader you have the right to opt out…

Even for the ones who don’t opt out, we don’t give them the location or the IP of the device, we just say, ‘around this time, so and so opened your email.’

That’s a respect for both sides of the ecosystem. Because we think that email is the last open protocol. We know that there aren’t any more communication protocols that are completely open. Facebook, Twitter, Slack, they’re all owned by private companies.

Email is the last one. And we really don’t want to make it so that we only serve our users, who’re usually the senders, we want to serve both sides of the table.

Source: Going Deep | 2022

On giving back as a foundational principle:

So when we started the company, we named it Baydin, we put in our company charter, at the time it was just wishful thinking, but the idea was when we make profits we were going to donate a portion of our profits to advance education in Burma.

And we didn’t really know if that’s where we’d get to at some point. Actually making profits when you’re just like signing your paperwork. And then one day, we were like, ‘wait, we’re actually profitable…’ We can donate.

So far we’ve done a few different projects. We funded an innovation, kind of a startup hub in Rangoon where I grew up. We did a mobile bus, to bring education to kids who cannot go to school because they’re working.

We have a very big tea-shop culture in Burma and a lot of them are run or staffed by kids who should be in school but can’t because of their family. They’re from villages, they come to the city and work at these tea shops to send money back to their families. So there’s no way for them to really learn or go to a regular school.,…

So somebody decided to start this project, so we funded the bus with him. They outfitted a school bus into a mobile classroom. And they go to these tea shops and teach kids after.

These kids are amazing. I admire them so much. They wake up at 5am, work all day, and the tea shops usually close around 5. So they’ve had a 12-hr workday and then they come to the mobile classroom to learn for another two or three hours.

Source: Fund BMC | 2020

On the routine, ever-more-demanding work of building on top of platforms:

An extension developer’s life is really hard. If I see a new entrepreneur, asking me, ‘hey, Moah, I want to talk to you about this new extension I’d like to bring, and we’re like, hey, ‘are you sure you want to do this?’

Because you’re at the mercy of multiple layers of controls and systems that are not quite logical. And may not be the top priorities for those companies.

So you’re always keeping up with different policy changes. ‘Hey, Safari is changing their API to this and is going to be deprecated in three months.’

So we dedicate December, the whole month of December to this. We don’t do any new product development to just keep up with all kinds of changes that everybody is bringing.

From Python language changes to Chrome Web Store is going to require these new things, to Gmail API is going to need this, and Outlook is doing this. All of that. One out of every 12 months, we have to resource everybody on that. That’s just to stay alive.

Source: Going Deep | 2022

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Glad to be hosting you here, @ayemoah.

Thank you for transparently talking about the exhaustingly difficult decision of lay-offs. A harsh potential reality most founders are aware of, yet something nobody wants to imagine. It’ll be helpful to hear your thoughts on how differently have you scaled up the Boomerang team and the culture since that decision in 2018.

And kudos on a decade of dedicated reading. What are some titles that have informed and influenced you as a founder over the years?

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Hey @ayemoah,

Thanks for doing this! Great to read a touching snapshot of your journey with Boomerang.

I’d love to hear your thoughts on:

  1. Pricing. You’ve mentioned that Boomerang’s pricing kicked off with voluntary user subscriptions, and has likely gone through multiple iterations since. What role has pricing strategy played in competing with tech giants and growing profitably with millions of free users?
  2. Giving back. It’s really inspiring to read that you had instituted giving back into the company charter from day one. What would your advice be to fellow founders pondering over making a similar commitment?
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Great journey Moah, very inspiring. Curious about a few things

  1. Did your investors have questions/concerns around your giving back charter?
  2. Why did you choose to keep the team so small? Wouldn’t a larger team be able to accomplish more/faster?
  3. How did you ‘plan’ your break? Just curious about the personal resilience journey there
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@ayemoah : It is truly inspiring to see you achieve multi-million ARR while taking so little outside money. Would love to know more about that -

What were your plans for the first $400k you raised?
What did you end up spending it on?
In retrospect, could you have achieved all this without fundraising at all?

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Glad to connect with you here Aye . Impressed with the rhyme “Hey Whoa!”.

Curious to know this - You have built a 10MM ARR with just 11 member team. So what are the qualities, traits in the recruits we should look for? and what is your experience with attrition and other people challenges in such a lean yet high-performance environment?

One more - Though aligning to the product vision is the key thing for a go-live. What are the other qualities that should be paid more attention to throughout the product development process considering the changes over time?

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Hi Aye! Wow wow wow! Thank you so much for participating in this AMA.

I had come across Boomerang a while back but I can’t believe I hadn’t heard of your story before. This is so incredibly inspiring! Congratulations to you and the team on an absolutely epic journey so far.

I am so interesting in everything here, in many ways because there’s so much overlap with our journey at GoSquared… The world has changed a lot since 2010 but it’s great to see real proper OG SaaS tools continuing to thrive to this day!

You mentioned you raised funding early on and then grew — how has the relationship with those investors changed / evolved over time, and how have you avoided the slippery slope of raising round after round of funding?

Also: I am trying to read more… but ~1 book a week is incredible! How on earth do you manage this?!

Thank you so much Aye, and if you are ever in London let me know — I would love to meet you and chat more!

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@ayemoah, thanks for sharing your story. It’s super inspiring. And kudos to you for setting a great example for other entrepreneurs and companies to follow, when it comes to the principle of giving back.

I see that you would be willing to talk about Decision making frameworks around product development - my question could be related.

I’ve observed a few products, that could do a good job as browser extensions, end up evolving into a standalone tooling (like a web app). A couple of reasons for this shift could be (a) the need to not depend entirely on the different browser extension marketplaces (even if that means pivoting or expanding into an adjacent space) and (b) to build a system of record which makes the product hard to replace for the customers. For these products, the extension becomes more of a growth channel than a product experience in itself is what I understand.

I would love to know your take on the above mentioned approach - I see that Boomerang still continues as a pure extension product. I’m also curious to learn if you’ve considered such a shift in product strategy anytime during the Boomerang journey. Thank you.

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Congrats on the amazing journey, @ayemoah!

You’ve mentioned how Boomerang has restricted meetings to a day each week and also that you’ve deliberately thought about carving a flow state into your own routine. Can you share some of the other productivity and comms practices that keep things sane for you as a CEO, as you accomplish so much with such a small team?

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Yes. Today is actually our meeting day! We set aside Thursdays for all our weekly update meetings. So for the exec team, it’s back to back meetings and can be rough. I tried to start Thursdays with a 30 min of yoga in the morning before sitting down at my desk to get my mind centered and ready for the onslaught of new info and decisions to be made. One other thing I do every day is keeping my lunch hour open religiously. I get up and pick some veggies from my indoor garden to eat with my lunch. Then my husband (who’s also my co-founder) and I take a walk around the neighborhood for about 30 mins. I think it’s important for us to refill our mental reserve in nature to ride the afternoon slump.

When I stepped into the CEO role, one of the first things I did was to write out this long form document called “Boomerang Guiding Principles”. Which includes the principles that guide us as a team and a manual for how we communicate as a team. I outlined in detail what information should go in which medium (Slack, Wiki, Email), how to schedule a meeting, how to run a weekly status update etc.

We also do a daily video standup to see each other as humans and figure out bottlenecks and dependencies, keeping each other updated on what’s going on. We followed that live standups with everyone sending a slack written update in the #daily-standup channel for record keeping so if someone is on vacation they can catch up easily on the pulse of the team.

We also do a 2 week ahead review at every Monday standup by opening up the company calendar and talking through the major things coming up.

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Our plans were to draw a minimal salary to pay rent and feed ourselves. At that point, we were on the verge of having to take on credit card debt. So that’s what we spent it on. After that, we also hired our first employee with that money.

Sadly no. We saved up money by moving into the suburbs halving our living costs a couple years before even starting the company. Both Alex and I didn’t come from money or didn’t have family around to fall back on. We had student loans. We started out with net negative net worth after graduating from MIT.

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I think you are probably referring to something like Grammarly. And yes, that is definitely the typical approach as evidenced by Grammarly’s resounding success. And yes, we have considered and even started working on a standalone email client at some point in the company history. It’s just a little bit harder for us because email is such a sticky habit. Part of the magic of Boomerang for Gmail and Outlook is the fact that you don’t have to change your ingrained daily workflow to take advantage of our features. Our users loved how well integrated the product experience is. So the only alternative is for us to build an email client as good as Gmail or Outlook, competing with their decade of development and hundreds of engineers. What’s considered a table stake for an email client is such a higher bar compared to a service like Grammarly. Superhuman took about 3 years to build with several millions of funding as another benchmark to consider.

I think that’s where we are headed for the company’s future with our meeting scheduling. We are starting with the in-browser extension but ultimately what we are going to become is the platform for meeting scheduling that interoperates with every client and every calendar provider.

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Thanks James!
Yea, it’s been quite different from 2010. I do like being the last company standing from our batch of companies we started out with.

We got profitable about 11 months after we raised our seed round I think. I might be off by a few months. But basically we got profitable before you were supposed to raise the next round. So the pressure to raise wasn’t there and it led us to not fully exploring the funding options very thoroughly. That’s how we got off that treadmill.

Thanks for the invite. I would love to visit London again. I have only been once.

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@ayemoah congrats on your success! I am inspired!

I would love to hear about your approach to product lead growth and what you’ve done from an outbound and inbound perspective to drive such phenomenal growth. Thank you!

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The giving back was something we put into the company charter as naive first time founders. But it was a very important value alignment between the three co-founders. We wouldn’t have such a wonderful relationship for over a decade of working together, if three of us didn’t value the same things. So you can view it as a value matching filter for choosing who to work with whether they are co-founders or investors.

For the causes that we choose to give back to, I went to MIT at the generosity of a donor setting up a scholarship fund for students from developing countries. I still had some student loans but the bulk of my MIT tuition was paid for by some stranger who I’ve never met. I felt very strongly that it’s important to pay it forward for the next generation. We also believe education is a force multiplier. Then when we started to feel the urgency of the climate crisis, since we aren’t actively solving the problem ourselves, we figured it’s important to contribute to the progress. I did a bunch of research on where the highest impact we can have and set up clear criteria for how to deploy our donations.

We are truly very lucky to have nicest investors you can imagine who happened to have value alignment with us on this. We also have returned their investments in multiple times over as dividends throughout the years. That definitely helps. :smiley:

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When we did voluntary subscriptions, getting revenue was only half of the goal. They also let us do a real world pricing test with the best data possible. People’s actual willingness to pay. So when we set the prices for our plans, we set them at $5/month (the single most popular amount people were willing to pay) for our personal plan and $15/month (the most expensive amount that a significant portion of voluntary subscribers chose to pay) for our everything-included pro plan.

We had a huge initial user base and so part of our thinking with our free plan was to make sure that there wasn’t a lot of room for copycat services to come in and undercut us. And that worked out pretty well - we’re at least 10x bigger than all of the clones to this day. If we’d had a viral component to the service (we didn’t, nobody wanted the people they were emailing to know they were scheduling emails to send later!) then we would probably have skewed more toward the free plan.

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Well the funny thing is we did indeed have a larger team previously (before the end of 2018) and we actually are moving faster now after we did our team resizing. It seems counter intuitive to what people would believe. It was so eye opening to us how much a small elite team can accomplish. I think there was a podcast episode of Reed Hastings talking about finding a similar thing after they did a big layoff at Netflix. If I find it again, I will link to it.

My plan was to talk to lots of people and get inspired by seeing what they are working on. The best route was to start angel investing and finding founders at their earliest stages. The checks I wrote weren’t big but I learned so much. The second thing was I really wanted to solve the problem of personal productivity beyond email, specifically around understanding what makes some people a lot more productive than others and how they find flow and how they fight procrastination. In a way, I joke that our whole life has been trying to make ourselves more productive and stop procrastinating. And I wanted to travel quite a bit while doing that. Each week, I allocated one day to attend meetings and guide the team at Boomerang, 2 days for angel investing and 1 day for productivity consulting and 1 day for exploring new tools, reading research papers. I had a lot of fun that year!

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I’ve only been CEO for a few months, so we’re just starting to ramp that up. There are a few big differences in the company’s position now compared to 2018. We now have a viral product in an established B2B category with with strong IP protection this time around.

So we’re investing much more heavily on marketing, customer success, sales, operations, and all the other things that build scale instead of just building technology. I have a big vision to make it efficient and respectful for anyone to meet with anyone, regardless of technology, and we’re going to be bringing that vision to life instead of just building new products constantly.

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our focused high performance team have

  1. people who love the work and truly enjoy their craft
  2. people who cared about what they’re building (I think the fancy way to say it is mission alignment) 3. people who like to see the impact of their work rather than the bureaucracy, middle management and political gamesmanship and
  3. people with high self awareness and maturity
  4. people with strong interests outside of work (almost everyone on the team does something unrelated to tech with wide ranging interests. This one we didn’t look for specifically, it just something I noticed.)

For attrition, we have no voluntary departure from the team that we kept after the end of 2018, throughout this whole pandemic. We are really proud of it.

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