Bootstrapping to a Billion-Dollar IPO: Dax Dasilva on Lightspeed's Journey

In this live episode recorded at the Elevate Conference, host Matt Cohen interviews Dax Dasilva, founder of Lightspeed and the conservation initiative Age of Union. The discussion covers Dax's entrepreneurial journey from his early days growing up in Vancouver as the son of Ugandan refugees, through the founding and growth of Lightspeed, and his venture into conservation and environmental advocacy. Dax shares insights on transitioning from a bootstrapped company to VC-backed growth, going public, his time away from the company, and his recent return as CEO. He also emphasizes the importance of spirituality, conservation, and embracing change as a leader.

About Dax Dasilva

Dax Dasilva is the Founder and CEO of Lightspeed Commerce. Founded in 2005, Lightspeed is the unified POS and payments platform for ambitious entrepreneurs to accelerate growth, provide the best customer experience and become a go-to destination in their space. It powers the world's best businesses in over 100 countries globally.

Dasilva was reappointed as CEO on February 15, 2024. Prior to that, he served as Executive Chair of Lightspeed’s board of directors for two years, and previously led the company’s operations as Chief Executive Officer since its founding in 2005.

Lightspeed employs thousands of staff, and powers hundreds of thousands of customer locations worldwide. During Dasilva’s leadership as CEO, the company went public in March 2019 on the Toronto Stock Exchange under the symbol LSPD, becoming one of Canada’s top 10 technology IPOs. In September 2020, the company listed on the New York Stock Exchange. Lightspeed also undertook 9 acquisitions over the course of a four year period to consolidate the global market and launch two, best-in-class flagship products: Lightspeed Retail and Lightspeed Restaurant.

In this episode, we discuss:

* (01:16) Dax explains his long-standing relationship with Elevate and the importance of in-person gatherings.

* (02:03) Growing up in Vancouver, Dax was introduced to technology through his father’s job and his early exposure to a Mac startup.

* (04:00) Dax talks about how his initial programming work with Mac dealerships led to the foundation of Lightspeed, serving complex retailers.

* (05:09) Dax reflects on balancing growth and profitability during Lightspeed's first seven years without external funding.

* (07:54) Dax stresses the need for a detailed business plan, which guided Lightspeed through its early years.

* (09:00) Lightspeed’s shift to VC-backed growth began with a $30 million Series A led by Accel, as Dax discusses how they prepared for scaling and moving to cloud-based services.

* (12:22) The challenges of leading a company through IPOs in Toronto and New York required Dax to adapt to public market pressures.

* (15:01) Dax shares insights on handling the volatility of public markets, especially during the pandemic and interest rate shifts.

* (17:00) Dax explains why he stepped back from Lightspeed in 2022, the projects he pursued during his time away, and the advice he received before returning.

* (18:43) Dax reflects on how spiritual practices like meditation have helped him balance various roles and projects.

* (20:32) Dax provides an overview of Age of Union, his conservation initiative, and his experiences with grassroots projects worldwide.

* (23:16) Dax encourages startups to embrace a learning mindset, iterating through failures, and applying entrepreneurial thinking to different fields.

Fast Favorites:

* Favorite Podcast: 20VC

* Favorite Newsletter: Nate Silver's Silver Bulletin

* Favorite Tech Gadget: InBody fat and body composition analyzers

* Favorite Trend: The rise of meditation

* Favorite Book: Good to Great by Jim Collins

* Favorite Life Lesson: "The journey is the reward" – Steve Jobs

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