Introduction

Welcome to the Zero to $10M ARR Podcast. I'm your host, Tom Morkes, along with my co-host Alex Turnbull, the founder and CEO of Groove and Helply. Today, we're excited to have Aye Moah, the Co-founder and CEO of Boomerang, join us.

In 2010, moah and her team pioneered the email productivity space by introducing features like message snoozing and scheduled sending, concepts now standard across various platforms. Under her leadership, Boomerang has grown to a multi-million dollar ARR company with minimal external funding, raising just $400,000 since their last round in 2011.

Remarkably, all three original co-founders continue to work together, a testament to their enduring partnership. In 2018, when tech giants incorporated similar features into their platforms, Aye navigated the company through potential challenges, emerging stronger and more resilient.

After a brief hiatus, she returned with renewed energy, stepping into the CEO role in the summer of 2020, and has since been driving Boomerang's mission to enhance email and meeting scheduling productivity.

Moah, welcome to the show!

Questions

1. What was the primary growth channel that got you to the first million in revenue, and looking back, was there anything you would have done differently in those early days?
2. Pros and cons of being a browser extension, something that relies on existing tech like gmail / outlook?
3. In 2010, Boomerang introduced features like message snoozing and scheduled sending. What inspired these innovations, and how did you approach educating the market about these new concepts?
4. How is the company structured in terms of ownership? What percentage do you and the other founders own, and how has that influenced decision-making over time?
5. Zero to $1M ARR: What was the primary growth channel that got you to the first million in revenue, and looking back, was there anything you would have done differently in those early days?
6. Scaling from $1M to $3M ARR: What strategies worked best during this phase? Were you doubling down on the same growth channels, or did you have to make a significant shift in how you acquired and retained customers?
7. $3M to $5M ARR Growth: At this point, many SaaS companies see diminishing returns from early growth channels. What were the biggest challenges in scaling past $3M, and how did you adapt your strategy to reach $5M ARR?
8. $5M to $10M ARR Expansion: What’s been the biggest driver of growth in this stage? How have your acquisition and retention strategies evolved, and what has surprised you the most about this phase of growth?
9. Current Growth Levers: Right now, what’s the primary lever you’re pulling for growth? What strategies and tactics are top priorities for Boomerang today?
10. Competitive Pressures & Innovation: In 2018, major tech companies integrated features similar to Boomerang's into their platforms. How did you assess the potential impact, and what steps did you take to differentiate and protect your market position?
11. Given your journey, what should founders think about when deciding whether to bootstrap or take outside funding? What are the biggest misconceptions about bootstrapping that you’ve encountered?
12. Pioneering Email Productivity: In 2010, Boomerang introduced features like message snoozing and scheduled sending, which have since become standard in email platforms. What inspired these innovations, and how did you approach educating the market about these new concepts?
13. Bootstrapped Growth: With only $400,000 in funding since 2011, Boomerang has achieved multi-million dollar ARR. What strategies did you employ to drive this growth with such limited external capital?
14. Co-Founder Dynamics: It's rare for all original co-founders to remain actively involved after more than a decade. How have you maintained this partnership, and what advice do you have for others to sustain long-term co-founder relationships?
15. Navigating Competitive Pressures: In 2018, major tech companies integrated features similar to Boomerang's into their platforms. How did you assess the potential impact, and what steps did you take to differentiate and protect your market position?
16. Leadership Transition: After taking time off in 2019 and 2020, you returned as CEO in mid-2020. What motivated this return, and how has your leadership perspective evolved since stepping into this role?
17. Product Innovation: Boomerang has a history of introducing unique features, such as the Magic Live Calendar for scheduling. How do you identify and prioritize new product developments to stay ahead in the productivity space?
18. User-Centric Design: With features now ubiquitous across platforms, how does Boomerang continue to offer unique value to its users? Can you share examples of how user feedback has directly influenced your product roadmap?
19. Balancing Innovation and Competition: In a rapidly evolving tech landscape, how do you balance the need for continuous innovation with the risk of competitors replicating your features?
20. Future Outlook: As email and communication tools continue to evolve, what trends do you foresee, and how is Boomerang positioning itself to meet the future needs of users?
21. Advice for Aspiring Entrepreneurs: Drawing from your journey with Boomerang, what key lessons would you impart to entrepreneurs looking to bootstrap and sustain a successful SaaS company?

Outro

That wraps up today's episode of the Zero to $10M ARR Podcast. A heartfelt thank you to Aye Moah for sharing her invaluable insights into bootstrapping, innovation, and leadership in the SaaS industry.

If you found this conversation insightful, please subscribe, leave a review, and share it with fellow founders and entrepreneurs. To learn more about Aye and Boomerang, visit boomerangapp.com.

Mo, thank you once again for joining us.