The Way In

Shijia Mao
  • 5.0 (5)
  • ENTREPRENEURSHIP

The Way In dives into the choices, risks, and lessons behind building a business. Each week, founders and small business owners share how they carved their own path - one choice, one risk, one step at a time.

  1. MAR 9

    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.

    32 min
  2. Kate @ Dip: Anti-Amazon Entrepreneur on Growing Without Selling Out

    FEB 28

    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.

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

    FEB 17

    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 helpThe co-founder dynamic: how different expertise drives early-stage growthThe early days of Claim Health and the key decisions that shaped its trajectoryMarket opportunities and the impact of healthcare policy changes

    26 min

  4. FEB 8

    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 foundBuilding vs. operating an existing businessLessons carried forward from Trevor's first startupHow lawyers worked before Olive Legal and what changes afterDesigning tools that support, not replace, legal professionalsHiring a CEO as a technical founderMeasuring success through retention and real usage

    33 min

  5. FEB 1

    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.

    29 min
  6. Navigating SaaS in the AI Era: How Sid @ Spendflo Chose to Disrupt His Own Company

    JAN 24

    Navigating SaaS in the AI Era: How Sid @ Spendflo Chose to Disrupt His Own Company

    In this episode of The Way In, I speak with Sid Sridharan, co-founder and CEO of Spendflo, about the evolution of the company from SaaS spend management to an AI-native platform. Sid shares lessons from founding and scaling Spendflo, the role of venture capital, the difficult decision to exit a market, and why he’s now focused on building AI teammates to reshape how procurement work gets done.

    23 min
  7. Radical Transparency: Sol @ Neptune on Building a New Prenup Experience

    JAN 18

    Radical Transparency: Sol @ Neptune on Building a New Prenup Experience

    In this episode, Sol shares her personal journey with prenups and how Neptune is changing the narrative around these conversations. We discuss the lessons she learned from her first startup, the challenges couples face when talking about money and prenups, and how Neptune aims to simplify the process through education and access to trusted experts. Sol also reflects on the role of AI in legal matters and shares her long-term vision for Neptune as the company expands its services.

    31 min
  8. Brian @ Verteel: Reinventing Medical Logistics with Drones

    JAN 9

    Brian @ Verteel: Reinventing Medical Logistics with Drones

    Brian, founder of Verteel, didn’t start out in tech - he started in the cockpit. In this episode, Brian shares his journey from being a professional pilot to building a drone company focusing on transforming medical logistics. He discusses the challenges of navigating regulatory environments, the importance of customer discovery, and the innovative approaches Verteel is taking to improve healthcare delivery through drone technology. We also touched on the future of drone delivery, the competitive landscape, and Brian's personal growth as an entrepreneur.

    43 min
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About

The Way In dives into the choices, risks, and lessons behind building a business. Each week, founders and small business owners share how they carved their own path - one choice, one risk, one step at a time.

Information

  • Creator
    Shijia Mao
  • Years Active
    2025 - 2026
  • Episodes
    23
  • Rating
    Clean
  • Copyright
    © 2025 Shijia Mao