Value, Systems, Vulnerability: Playing Long Games with Yommy Ojo
Themes: FOMO and unspoken motivations · social acceptance versus financial reality · vanity metrics and what actually matters · retention as the truest indicator · playing long games with long people · the real costs of ambition (health, family, mental wellbeing) · structured vulnerability and personal boards of advisors · systems as foundation for scale · value exchange and what we give to others · the psychology of buyer decisions · when everyone wants what they don't have
What are you really chasing?
"I'll never forget when a friend of mine said he got into Selfridges," Yommy tells me. "His business got into Selfridges, and then the day after, he hit such a low point."
The reason? He'd only set a goal as far as reaching the big mega store. He didn't actually know what his identity was afterwards.
This is where our conversation begins - in that uncomfortable space between the goals we set and what we actually want.
Yommy Ojo knows this territory well. From investment banking to building and scaling tech startups, he's seen the full spectrum of how founders relate to money, growth, and success. As a systems and growth strategist, he now helps service-based businesses grow with less stress and more profit - and he's deeply attuned to aligning growth with what founders truly want to achieve.
The goals we won't admit to
When I ask Yommy about the gap between financial goals and what founders actually want, he shares an example that gets to the heart of it.
A founder was already making £20K a month - good money, better than some of the biggest influencers in her space. But as Yommy discovered, she wanted to hit £30K months because she wanted to be accepted socially in certain circles.
"It didn't matter about the fact that she was making good money," Yommy explains. "What mattered to her was the fact that people weren't speaking about her business, her brand, and giving it as much reverence as some of the other names."
She was missing out on being part of certain conversations, certain circles. That's FOMO - the fear of missing out - and it's not just about trends or sales tactics. It's about belonging, about being included in the spaces where other successful founders gather. It's one of the most powerful human behaviours, and it drives business decisions more than we like to admit.
Yommy describes another situation: two founders. One had the big profile, all the likes, the follows, the social credibility - but their business wasn't making as much money. The other was technically invisible online but was generating far more revenue.
"This big influential founder was actually coveting having a business that was generating more income," he says. "Whereas this other less known founder was actually coveting having the influence."
Everyone wants what they don't have. But here's the thing - those external metrics rarely tell you what's actually happening inside a business. A £30K month could mean healthy profit, or it could mean you've just spent a fortune on ad spend with razor-thin margins.
At what cost?
This brings us to one of the most important questions Yommy poses throughout our conversation: At what cost?
He talks about Naval Ravikant's principle of "playing long games with long people" - and how the game you're playing matters more than how fast you're playing it.
"Business is about solving a problem and going on a journey where there's the possibility of success, the possibility of failure," Yommy says. "And who do you play that game with? I believe that is gonna make all the difference."
Depending on what stage you're in, getting started obviously requires momentum. But keeping that ambition going at all costs? That's where founders need to pause.
"Is it the cost of your employee's mental health? Is it the cost of your family?" Yommy asks. "You might be saying, oh, I'm working this hard to provide these things for my family. But if you end up losing your wife in the process or not having a really good relationship with your kids, was it worth it at all?"
He pauses, then adds another cost we often forget: "Your health."
One needs to be cognizant of what they're sacrificing in the process. The opportunity costs. What could you be doing instead that the world or the market actually wants from you?
The metrics that actually matter
So if revenue isn't the whole story, and social proof is often a vanity metric, what should founders actually pay attention to?
For Yommy, the answer is clear: retention.
"Retention is the biggest leading indicator of growth," he tells me. "If you are acquiring customers continuously, but customers are leaving as quick as they come, you'll never be able to grow your business."
Beyond retention, he recommends keeping your eyes on:
- Cost of acquiring a customer (CAC)
- Lifetime value of a customer (LTV)
- Average value of a customer
"Investors want to know that you, as the owner of the business, have a handle on what it costs to acquire a customer," he explains. The lifetime value gives you a barometer for what you should spend to acquire that customer. And understanding average customer value helps you determine whether your sales team is chasing the right opportunities.
"We all find that the customers that pay more tend to be better clients, tend to be better customers," Yommy observes.
One of the best sales-focused founders he worked with would say: "There's so much money in my CRM." This founder thought of every person as a potential customer, and existing customers as people he could help expand their journey with.
"A lot of the basic mistakes we can make is to think about acquisition and acquiring new customers, but forgetting that you need to build trust in the beginning," Yommy says. "Whereas your existing customers - as long as you delight them, as long as you stay front of mind and balance that ratio of delivering more value before you ask for the next ask - there's so much money on the table."
The power of structured vulnerability
When I ask Yommy about advisors and governance, he shares something unexpected: a WhatsApp broadcast list.
He credits a friend, Claudine, with the idea. Early in her journey, she created her own personal board of advisors. Not formal mentors - because asking someone to be your mentor can feel overwhelming for everyone involved. Instead, a simple group of people who genuinely cared, understood a bit about her, and wanted to see her win.
Yommy started with a broadcast list on WhatsApp. In a very honest way, he would update people on: his wins, his lessons, and his next steps.
"It's quite funny what started as a small list grew slightly, but even without any responses, the process of writing that down really helped me and shaped me," he reflects.
The broadcast format did something else too - it allowed people in his inner circle who really cared about him to know what he needed help with. To see the journey he was on. To stay front of mind for them.
"One of the people in that group has actually opened up about some of the challenges she was having with the stage of her business," Yommy shares. "That's led to a much stronger relationship. We're actually meeting in a couple weeks time."
He pauses, then asks: "Would we have this connection if I wasn't sharing so freely in this format?"
There's something here about vulnerability and connection that runs counter to typical founder culture. The secrecy. The cards held close to the chest. The reluctance to tell investors when things are going wrong.
"I find that being vulnerable and with the right people - even in content - when people have done their most vulnerable content or they've been willing to be embarrassed a little bit, people lean in so much more," Yommy observes. "At the end of the day, that is the real cost - a little bit of dignity. But it seems to work."
It comes back to what we discussed earlier about wanting social acceptance, about belonging. We're humans even when we've got a hat on as founder, entrepreneur, business leader. We're still trying to manage relationships.
"When people are telling something personal, we all just stop and listen," I say. "It's a great way of getting people's attention and bringing people in on that journey."
Systems as foundation
Our conversation comes to systems - the behind-the-scenes work that makes everything possible.
"I personally love it, love it, love it," Yommy says with genuine enthusiasm. "The right system is the one that gives you the truth about where your business is in a very centralised way, a way that's easily accessible, but also gives the leadership oversight of the bits that they need to."
He's quick to add: "It takes time. It takes time to get a really good setup."
But here's what he's learned working with businesses at different stages: if you're looking to get external funding or prepare for an exit, having your numbers ready makes your life so much easier.
"We've all seen The Apprentice, right? Or Dragons' Den? Not knowing your numbers - when the dragons feel that out, it's almost like attack. You can win half that battle just by being prepared, just by getting an eye on your numbers."
What shocked him most? How many businesses that had been running for years at a certain size didn't have these things in place.
"It doesn't need to be overnight," he reassures. "It could be something, a decision you can make right now to say, actually we wanna be on top of our numbers."
Having real-time information means you can actually make decisions. You can monitor metrics and influence them. Without the setup to have data coming through in a way that makes sense, you often find things that went wrong six months ago that you didn't realise.
This is where Yommy's background in investment banking comes full circle. The systems and controls, what's measured, the routines - that discipline from big institutions is exactly what growing businesses need.
"If you've seen what good looks like in a big system, which a lot of smaller businesses are aspiring to be if they're growing, you need really good systems to make it happen," I observe.
"That's it. Yep," he agrees.
What money means
Toward the end of our conversation, I ask Yommy: if money were a person, what would you like to say to them?
His response is immediate and heartfelt:
"Thank you for the journey you've taken me on, and truly helping me to realise and understand what value means. Because for me, value is what you give to other people, not what you implicitly are. Or feeling valuable. It's what you do for other people. It's what you give to other people."
And that's why, at the very beginning of our conversation, when I asked him what comes up when he hears the word "money," he said: value exchange.
We can get so carried away with what value means - with revenue targets and social proof and all the external measures of success. But Yommy brings it back to something tangible and mission-driven: what can I do to help other people?
That's the real metric that matters.
Connect with Yommy Ojo
Want to work with Yommy and Online Ascension? He's offering podcast listeners and readers here a free sales funnel audit where he'll run your numbers and visualise your profit potential. Connect with him on LinkedIn and mention the Money Story Project podcast.
This conversation reminds us that the numbers we chase often hide deeper needs for connection, acceptance, and meaning. And that the most sustainable path forward isn't about growth at any cost - it's about playing long games with long people, with systems that support real value creation.
Listen to the podcast episode with Yommy here or via Spotify or Apple Podcasts
