In this episode of Connected Commerce, Hai Mag sits down with Clark Lindsey, CEO of Try Olina, to discuss why cash flow is one of the biggest challenges facing ecommerce brands and how smarter financial decisions can unlock faster, more sustainable growth.

Clark shares his journey from selling phone cases in high school and launching a meal plan business, to working in venture capital, and eventually returning to ecommerce to solve the problem founders kept bringing up: cash flow.

He explains how Try Olina helps brands replace large bills, including inventory, 3PL, logistics, and Meta invoices, with a single daily payment. Instead of saving up for a big bill at the end of the month, brands always know how much capital they have and can put the rest to work on advertising, inventory, and growth.

Hai adds the brand owner's perspective: as a business scales, its operating cash needs grow with it, and that gap often becomes one of the biggest headaches for founders.

The conversation then turns to one of the most important questions in ecommerce finance: when should a brand take on debt?

Clark breaks down the difference between using debt to fix a timing problem and using debt to fund growth. When debt is used to cover timing gaps, such as waiting on marketplace payouts while a large bill comes due, it often leads to a "debt spiral," where strong businesses with great unit economics end up sending a significant share of every sale toward debt payments.

They discuss how to recognize this pattern, why debt should be tied to a clear growth model, and practical alternatives like paying large bills early in smaller installments.

The discussion then shifts to the growth side. Hai explains how Eva Commerce approaches advertising like a poker game: deciding where ad dollars should go across Meta, Google, and Amazon, and understanding competitors' pricing, inventory, and strategy to know when to attack, defend, or target new audiences.

They also explore why cash constraints hold brands back. Advertising returns can take 30 to 60 days to arrive, and without enough cash on hand, founders hesitate, underinvest, and lose ground to faster competitors.

At the center of the episode is a simple idea: sustainable ecommerce growth requires both healthy cash flow and a smart growth strategy, working together as one connected system.

Host: Hai Mag, CEO of Eva Commerce

Guest: Clark Lindsey, CEO of Try Olina

Connect with Clark:

LinkedIn: https://www.linkedin.com/in/clark-lindsey-370565124/

Try Olina: https://tryolina.com

Follow Eva Commerce:

Website: https://eva.guru

LinkedIn: https://www.linkedin.com/company/eva-commerce-inc/

Instagram: https://www.instagram.com/eva_commerce/