In this episode, Ashwin Kamlani shares his dynamic journey from an e-commerce pioneer at Melia Hotels to becoming a serial entrepreneur and the CEO of Juicer. Ashwin dives deep into the critical moments that shaped his career, including how he transformed Melia’s e-commerce strategy from the ground up, his leap into entrepreneurship after a bold offer from a Danish entrepreneur, and his decision to bootstrap his first company.

Ashwin highlights the lessons he learned from bootstrapping versus raising capital and shares his unique perspective on transparency, leadership, and balancing the personal with the professional. From walking into meetings with the chairman of Melia as a young leader to driving across the U.S. in a pink polka-dot RV with his daughter—meeting clients along the way—Ashwin offers powerful insights into the entrepreneurial mindset. He also reflects on the importance of staying true to yourself in business and how bringing his personal life into his professional world has helped him build trust and lasting relationships.

Throughout the episode, Ashwin candidly discusses the challenges of scaling a business, the tough calls he's had to make, and why intuition and authenticity remain his guiding principles.

Chapters

00:00 Introduction and Ashwin's Early Career at Melia

02:17 Rising through the Ranks: From Intern to Global VP
06:55 Pioneering E-Commerce at Melia Hotels
10:58 The Leap into Entrepreneurship: Regatta Travel Solutions
14:53 Bootstrapping vs. Raising Capital: Lessons from Both Worlds
21:12 Navigating Acquisition and the Next Chapter
24:48 Juicer’s Origin and Navigating Dynamic Pricing
32:09 On the Road: Ashwin’s RV Journey with His Daughter
39:24 Personal Insights: The Role of Family in Entrepreneurship

Takeaways

Ashwin’s journey underscores the importance of bold risk-taking, from relentlessly pursuing an unpaid internship to launching his first startup after a life-changing opportunity.
Authenticity and transparency in business foster trust, leading to deeper client relationships and stronger connections, even in highly competitive industries like hospitality and restaurants.
Successful entrepreneurs must balance instinct with adaptability, knowing when to pivot and when to stick to their vision.
Bootstrapping taught Ashwin independence and ownership, while raising capital with Juicer gave him the resources to scale quickly—each path offers valuable lessons.
Dynamic pricing in restaurants offers a vast opportunity, but fear of consumer backlash is a hurdle many companies are hesitant to tackle.
Ashwin’s journey across the U.S. in a pink polka-dot RV with his 12-year-old daughter offers a unique blend of personal and professional life, illustrating how family and business can intersect in meaningful ways.
Having institutional investors who trust your judgment and support your vision can be a game-changer for scaling a business.