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

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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About reading I figured I’d put my one answer in a single reply.

I’ve always been a book worm since I was a kid. There were many arguments with my parents around books & reading (which books I’m allowed to have, book I wanted was too expensive, reading in the back room instead of socializing when my parents were hosting a party, reading late into the night and not sleeping enough etc). To me, reading is how I live multiple lives instead of just one.

I read for fun and without prejudice against any particular genres. But the book must be interesting enough for me to finish. I probably start 80 books a year but only finish 50. There are books I can’t get through and I just leave them unfinished because life is too short to be a completist about something I am not enjoying.

Here is a tip for those who want to read more books but feel stuck when they picked a book that they don’t enjoy because people tell them they should or must read this book or that. Give yourself permission to not finish a book you are not enjoying and excited to pick back up.

The other trick is to always have the next few books you want to read lined up. I am always getting recommendations from people or podcasts and saving them in my Kindle by using the send free sample feature from Amazon. It’s not unusual for me to be reading 3 books in parallel because each day you have a different mood and different books suit different moods. I also re-read books I’ve read previously when I need something comforting.
I think the reason I can read hundreds of books over the years is because I don’t treat it as a chore or a checklist to get through. I read what I enjoy and find interesting and want to learn about. Make reading fun and the habit will stick with you for life. This is how I am introducing reading to my kids too.

As for when I find the time, I read in bed every night before going to sleep. It can range from 15 mins to an hour to sometimes a couple hours. I am also an occasional insomniac and there are nights I read almost all night. Don’t recommend that approach but if you read 20 mins a night every single night, you can finish probably 2 books a month on average. But make it a fun habit instead of something you ought to do.

Book Recommendations for entrepreneurs:
Influence by Cialdini (everything we do is selling or convincing or persuading)
Checklist Manifesto by Gawande (this is required reading for operations side of our team)
Nudge (so many things that you can apply to ranging from marketing copy, product design, customer communication to team processes)
Farsighted : how we make decisions that matter
Getting Past No and Getting to Yes (the classics for negotiations)
These are the ones I would recommend. There are many okay books for particular topics I want to learn or grow. But these are the ones I would recommend for any founder.

You might notice a trend in that I tend to favor research based non-fiction over biographical business books. I can count biographical business books that I have read in two hands despite having read tons of non-fiction. I’m not sure why that is.

If anyone wants fun books to read, I have tons of recommendation for fantasy, sci fi and literary fiction. The genre I particularly enjoy is historical multigenerational epic sagas.

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Thanks for sharing where that early impetus for paying it forward comes from, @ayemoah. And voluntary subscriptions, as you’ve deployed them, seem like an excellent way for testing pricing levels.

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Thanks @ayemoah. How you’ve restructured the product and the team to diffuse bigger risks is quite instructive. And thanks also for telling us about your reading philosophy and making some great recommendations, too. :slight_smile:

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@ayemoah, thanks a tonne for sharing, in thoughtful detail, how you’ve navigated some of the currents of starting and scaling up Boomerang. :raised_hands: As is evident in how often ‘inspiring’ shows up in the founder questions above, there’s so much to learn from your unique and spirited journey. :sunflower:

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And, thanks, as always, to Relay founders (@wingman4sales, @puneet, @Deepika, @jamesgill, @matthew, @aditi1002, and @patty) for their open, searching, and equally thoughtful questions. :raised_hands:

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Thank you so much, Aye! This is so fascinating and connects up with advice others have given me — don’t feel the pressure to keep going and finish a book if you are struggling to read it each night. Thank you!

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