In this episode, we are joined by Elia Wallen, Founder and CEO of Engine (formerly Hotel Engine), the B2B travel booking platform that's streamlining how businesses manage their travel needs. From its origins as an internal tool for Elia's previous company, Travelers Haven, to becoming a $2.1 billion company, Engine has carved out a significant niche by focusing on serving SMBs with a frictionless approach to corporate travel management.

In this conversation, Elia shares his unconventional path from dropping out of college to founding multiple businesses, including the fascinating story of how Engine began as a side project that he almost shut down several times. We explore his philosophy of maintaining "strong conviction loosely held," his approach to fundraising (including a nail-biting near-miss with payroll), and why staying focused on doing one thing extremely well before expanding was crucial to Engine's success. Elia also offers valuable insights on bootstrapping versus raising capital, building in a non-tech hub, and why eliminating friction for customers has been central to Engine's competitive advantage in the crowded travel tech space.

(00:00) Introduction
(04:20) Where did Elia grow up and how did that shape his view of the world?
(04:42) Why did growing up in Naples push Elia to succeed?
(05:32) Did Elia always think he was going to become a founder?
(06:28) How did earlier founding experiences shape his view of leadership?
(07:28) What is Engine's core product?
(08:51) How does someone break into the corporate travel space?
(10:05) How did Elia think about scaling the go-to-market motion?
(11:59) How did Elia position Engine as it scaled?
(13:55) How did Elia and his leadership team discern which was the right scaling direction to go?
(15:57) How does a founder balance extreme focus while managing two businesses?
(18:29) How was building a company in Denver, and what prompted the decision to move to the Bay Area?
(20:42) How did fundraising begin for Engine?
(22:40) What is a moment when things didn't go as planned during Elia's founder journey?
(25:41) How did Engine think about building out both the integration suite and the business model?
(28:25) How will AI affect Engine's business model and policies?
(30:07) How is Engine thinking about diversifying customer benefits?
(31:35) How is Elia feeling about corporate travel as a sector for growth and opportunity?
(32:04) Where does Elia think Engine and he will be in five years?
(33:20) Who is a woman in Elia's life that has had a profound impact on him and his career?

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