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Gilbert started Leaf Grow in 2018. They detail the beginnings of their company in their Starter Story interview: 
Q: How did you get started on Leaf Grow?
Leaf got started as a consumer-play offering music fans a different kind of music experience in the form of Leaf Music, one that would put the artist at the center (vs the playlist of most other services) and one where sharing your favorite music was built in its DNA. We wanted to connect fans and artists together and in doing it, to give artists a direct way to engage, grow and monetize their fanbases. Little did we know that the very same foundation we build to help us grow Leaf Music would become the future of the company in the form of Leaf Grow, and that just as we helped musicians and their teams to reach the right people at the right time, we would go helping brands, commerce, and companies of all sizes to deliver on their growth objectives by empowering to reach and engage their perfect customers.
When we started Leaf Music we didn’t know anything about marketing, the founding team was product people and as such, we took a very engineering approach to marketing. Using as a starting point a hypothesis about who our target customer would look like, very soon we found that acquiring customer was expensive, very expensive, and knew that for it to work we needed to nail down the right audience really quick, one that would find our offering perfect for their needs and one that would allow us to scale.
> Make it profitable, then scale. Focusing a profitable business from the get-go will give you the right blueprint for when the time is right to scale.
We built python scripts that would allow us to iterate through these hypotheses fast, crunch the data and guide us in the direction we needed to evolve. This constant refinement gave us a leap forward and soon we were delivering growth at a fraction of the cost of most other advertisers both on Facebook as on Twitter. Facebook wrote a case study about us, invited us over to Palo Alto to accelerate our approach and there and then we realize that we have had created was special.
Leaf Grow became our vehicle to share with others what we had built, the growth engine that propelled us to become one of the main music services in Latin America, the same engine that would allow artists big and small to double the performance of their promotion campaigns and deliver sold-out campaigns for both merch, releases and tours; more often than not, breaking the internal benchmarks of their labels, majors and indies.