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Marketplace to Subscription: Matt Ovenden’s Playbook Shift

Marketplace to Subscription: Matt Ovenden’s Playbook Shift

TGTC Content Team 4 min read

In this episode of The Future of Consumer Marketing, host Roman Kirsch interviews Matt Ovenden, serial entrepreneur and founder of The Wine Engine and Borrow A Boat. After building Borrow A Boat into a 400,000-user platform that transformed the boat charter industry, Matt is now applying his marketplace expertise to wine subscriptions. The Wine Engine represents his shift from low-frequency, high-ticket transactions to high-frequency, subscription-based consumer marketing. Through AI-powered personalization, flexible subscription models, and a focus on making wine more accessible, Matt is challenging traditional wine clubs and major players like Vivino by creating what he calls “the Netflix of wine.”

Topics Discussed:

  • Building subscription-first businesses in traditional industries
  • Using AI for personalization and consumer education in wine
  • Transitioning from low-frequency marketplace to high-retention subscription model
  • Competing against established players without massive marketing budgets
  • Leveraging crowdfunding as both capital and marketing platform
  • Evolution of marketing tools and team structures in the AI era
  • Preparing for the shift from SEO to GEO (Generative Engine Optimization)

Lessons For Consumer Marketers:

Build Subscription-First and AI-Native From Day One

Unlike his boat business which was transaction-focused, Matt designed The Wine Engine as subscription-first with AI personalization built into the core experience. This approach reflects how modern consumers expect personalized, convenient access to products rather than one-off purchases.

Use AI to Democratize Expert Knowledge

The Wine Engine’s “Grapevine AI” serves as a personal wine concierge, allowing customers to ask questions they’d be embarrassed to ask in person. This removes barriers to entry in intimidating industries by making expert knowledge accessible through conversational AI.

Leverage Crowdfunding as a Marketing Platform, Not Just Capital

Matt discovered that equity crowdfunding platforms with over a million investors provide massive marketing reach. By converting customers into investors and investors into customers, he created a virtuous cycle of engagement that goes beyond traditional customer acquisition.

Focus on Lifetime Value Economics in Subscription Models

The shift from Borrow A Boat’s monthly customer acquisition mountain to Wine Engine’s recurring revenue model completely changed his marketing approach. Higher lifetime value allows for different unit economics and more diverse marketing strategies.

Prepare for the SEO to GEO Transition

Matt is building The Wine Engine to be optimized for AI search engines from the start, recognizing that traditional SEO is evolving into Generative Engine Optimization as consumers increasingly use AI tools for product discovery.

Choose Digital Channels That Can Be Tracked Over Above-the-Line

Despite spending significantly on tube station advertising and boat show sponsorships with Borrow A Boat, Matt found that trackable digital channels often provided better returns. However, he notes that above-the-line marketing still has value for reaching audiences who don’t engage with digital acquisition channels.

Automate More Marketing Functions with AI Tools

Modern marketing teams can accomplish more with fewer resources by leveraging AI for content creation, multi-channel posting, and strategy development. This allows smaller teams to compete with larger, more established players.

Build Authentic Voice and Communicate Across Multiple Channels

Matt emphasizes having a meaningful brand narrative and communicating consistently across all media channels. With consumers consuming more media than ever, authentic brands have more opportunities to connect with their audience.

Address Industry Pain Points with Flexibility and Personalization

Traditional wine clubs select wines for customers with limited flexibility. The Wine Engine differentiates by allowing customers to choose their wines each month while providing AI-powered recommendations, combining convenience with personalization.

Consider International Expansion Challenges Early

While Matt aims to build the biggest wine subscription in the UK first, he notes that international expansion in wine faces unique shipping and regulatory challenges that require careful planning.