8. Value, Systems, Vulnerability: Playing Long Games with Yommy Ojo

"FOMO is one of the most powerful human behaviours. Having acceptance or having clout is actually a big powerful motivator for a lot of business owners. But it's rarely talked about openly."

That's Yommy Ojo speaking a truth most founders don't say out loud—and it's where our conversation begins.

In this episode, Yommy—entrepreneur, systems and growth strategist, and founder of Online Ascension—shares what he's learned from working inside the startup and scale-up ecosystem. From investment banking to building digital products in fast-growth tech companies to founding his own businesses, Yommy has seen both the ambition and the scars that come with entrepreneurship. He now helps service-based businesses grow with less stress and more profit, focusing on scalable systems that enable leads, sales, and sustainable growth.

But this conversation goes deeper than tactics. It's about the psychology underneath our financial decisions, the costs we don't talk about, and what it means to build something that actually matters.

In this conversation, we explore:

  • The goals founders won't admit to—how social acceptance and recognition often drive financial targets more than we realise, and why everyone wants what they don't have
  • Why revenue numbers don't tell the whole story—and what founders should actually be measuring instead
  • "At what cost?"—the question every founder needs to ask about their ambition, and Naval Ravikant's principle of "playing long games with long people"
  • What founders should sacrifice and what they shouldn't—employee mental health, family relationships, personal health, and the opportunity costs we ignore
  • The metrics that actually matter—why retention is the biggest leading indicator of growth, and how understanding CAC, LTV, and average customer value changes everything
  • Why existing customers are where the money is—and how the best founders think about their CRM differently
  • The sales psychology most people miss—understanding different buyer decision-making styles and knowing when someone is hot vs. when they need time
  • How to create your own personal board of advisors—Yommy's WhatsApp broadcast list practice that became a powerful accountability and connection tool
  • The power of structured vulnerability—why sharing wins, lessons, and next steps openly (with the right people) creates deeper relationships and opportunities
  • Why so many businesses don't have their systems sorted—even years into operation, at significant scale—and what investors can smell a mile away
  • What "good systems" actually look like—centralized truth, accessible data, leadership oversight, and why it takes time to build properly
  • The full-circle moment between banking discipline and startup growth—how the systems, controls, and metrics from big institutions are exactly what scaling businesses need

We also talk about leaving a stable, well-paid banking job to follow curiosity into tech, the social pressure around "prestigious" career paths, what it means when founders aren't honest about their real motivations, why being vulnerable in content makes people lean in, how to audit a sales funnel, and why knowing your numbers is half the battle with investors.

It's a conversation about money, yes. But also about honesty, connection, and understanding what we're really building for—and at what cost.

Read the accompanying article: Value, Systems, Vulnerability: Playing Long Games with Yommy Ojo

Connect with our guest Yommy Ojo:

Special Offer from Yommy: Mention this podcast and get a free sales funnel audit where Yommy will run your numbers and visualise your profit potential.

Learn more about The Money Story Project and how to share your own story.

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