From Engineer to Operator: Trevor @ Olive Legal on Taking Over a Business He Didn’t Start

Ricky @ SourceReady: The Global Supply Chain Reset

Ricky sold his first startup at 23. Instead of taking a break, he jumped straight into building SourceReady, an AI platform that helps companies source top products from global suppliers. In this episode of The Way In, Ricky shares his vision of building the “Google search for supplier data”. Why now? In 2025, the U.S. collected $287B in customs duties - up 192% year-over-year. For the first time since the 19th century, tariffs became a major revenue pillar again. More and more companies have to adapt the global supply chain reset, and SourceReady is built to navigate through it. We talked about his journey from dropping out of UC Berkeley to becoming a serial founder, his experience of building in the ecosystems in China and the U.S, the challenges and opportunities in the global supply chain landscape, and what businesses should expect as trade policies and tariffs continue to evolve.

Kate @ Dip: Anti-Amazon Entrepreneur on Growing Without Selling Out

In a beauty industry obsessed with greenwashing and Amazon scale, Kate Assaraf, founder and CEO of Dip, chose a different path. In this episode of The Way In, Kate shares how she built a 7-figure haircare brand rooted in community and clear positioning. We talk about early product development, her decision to grow without Amazon, and why brand positioning matters more than massive distribution. She also opens up about rejecting preachy sustainability marketing, cutting through industry misinformation, and building a performance-driven brand without selling out - all while balancing motherhood and leadership.

JJ Ram @ Claim Health: From Startup Bouncer to Building for the $100B Home Health Market

In this episode of The Way In, I speak with JJ Ram, CTO and co-founder of Claim Health, about his journey from a start-up bouncer to building an AI company for the $100B+ U.S. home health industry. JJ shares how he and his co-founder navigate the challenges of running a startup together - combining deep tech expertise with the operational knowledge of their clients and learning how to complement each other’s strengths along the way. We dive into: * Operational bottlenecks in home health care and how AI can help * The co-founder dynamic: how different expertise drives early-stage growth * The early days of Claim Health and the key decisions that shaped its trajectory * Market opportunities and the impact of healthcare policy changes

From Engineer to Operator: Trevor @ Olive Legal on Taking Over a Business He Didn’t Start

In this episode of The Way In, I speak with Trevor, CTO of Olive Legal, about stepping into leadership at a company he didn’t start. Trevor joined Olive Legal as the first engineering hire, drawn by the chance to learn from experienced founders. When those founders later moved on to a new venture, Trevor was faced with an unexpected opportunity: take over a revenue-generating business while untangling an inherited codebase and finding the right partner to build alongside. IN THIS EPISODE, WE COVER: * Taking over a company you didn’t found * Building vs. operating an existing business * Lessons carried forward from Trevor's first startup * How lawyers worked before Olive Legal and what changes after * Designing tools that support, not replace, legal professionals * Hiring a CEO as a technical founder * Measuring success through retention and real usage

Founder Duo @ Marmalaide: Where Creativity Meets AI Marketing

In this episode of The Way In, I speak with Eric and Dev, the founder duo behind Marmalaide, a company using generative AI to create high-quality marketing content. Eric shares his background as an independent filmmaker and how the writers’ and actors’ strikes pushed him to experiment with AI, leading to a viral parody video that helped catalyze Marmalaide’s early momentum. Dev breaks down the business model, from defining the ideal customer profile to balancing one-off projects with long-term collaborations, and shares their view on the future of AI in marketing.