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07
April 2026

Unlearning to Learn: Entrepreneurial Lessons with Bryan Habana

Dov Girnun
Host
Bryan Habana
Rugby Legend, Entrepreneur. Paymenow Co-Founder
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In this podcast
Here We Grow, by Merchant Capital, is the podcast for South African entrepreneurs ready to scale. Hosted by Dov Girnun, each episode features candid conversations with the leaders behind some of the country’s most inspiring homegrown businesses.
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In this episode of Here We Grow, Dov Girnun sits down with Bryan Habana, rugby icon and founder of Paymenow, to unpack how lessons from the team, the field, and family have shaped his life. From discipline and resilience to leadership and trust, Bryan shares how the mindset forged in sport has translated into building and scaling a purpose-driven business and the unlearning required along the way to succeed beyond the game.

Transcript

Chapters

●      00:00 – 00:27 | Opening

●      00:28 – 04:46 | Transitioning from a Springbok to an Entrepreneur

●      04:47 – 06:05 | Unlearning to Learn

●      06: 06 – 08:18 | Balance

●      08:19 – 09:56 | MVP

●      09:57 – 14:22 | Unlearning

●      14:23 – 21:37 | Growing Paymenow

●      21:38 – 26:25 | Kaizen Principle

●      26:26  – 41:55 | Raised in Privilege

●      41:56- 44:25 | Looking Ahead: Delivering Respect

00:00 | Opening


Dov: Welcome to the Here we Grow Podcast. Today I’m joined by Bryan Habana, rugby star and entrepreneur.

00:28 | Transitioning from a Springbok to an Entrepreneur


Dov: How have you managed to transition from a Springbok rugby player into a successful entrepreneur? 9 out of 10 successful sportsmen don't manage to make that transition. You peak in your 20s or 30s, very different to someone’s business career. Typical entrepreneurs peak in their 40s, 50s, or 60s.

Bryan: The stat in South Africa is that if you play schoolboy level rugby in your final year of school in South Africa, your chance of becoming a Springbok rugby player in the next decade is around 0.00058%. Since 1896, I think there's only ever been 957 players that have represented South Africa.

Bryan: I started my first ever game at King Edward School in the Under 14G side. There were a lot of learnings in rugby, and you get thrust into the limelight early. The biggest thing sportsman struggle with is a sense of purpose when you retire and the fact that you must unlearn to learn.

04:47 | Unlearning to Learn


Bryan: You can build a brand, you look after who you are, create partnerships, don't burn bridges. In the business world you become reliant on the team around you. I needed to unlearn the methodical way of being disciplined, of sacrifice, because in a business context, you need to unlearn to be able to learn new things.

Bryan: I think that's where a lot of athletes get it wrong, because when you do retire, that sense of purpose and identity gets stripped away from you.

Dov: I'm just sitting here thinking about how powerful and how applicable that is in business and building a business. And you had to do it at such a young age.

06:06 | Balance


Bryan: Unfortunately, if you want to be the best or successful in something, balance is the last thing. I use the simple equation, if you have 3 silos in your life, if you have work, life, physical, and you give each silo balance in a mathematical context, you're giving each silo 33.3333%.

Bryan: How do you be intentional in those allocations of time that you get within those silos? Discipline, sacrifice and hard work on non-negotiables. There's an element of sacrifice that people think is just not there when you're in this balance, but there's unfortunately sacrifice.

Dov: You hear a lot of successful CEOs talking about it. There’s no such thing as a work-life balance if you want to be ambitious. It is all about integration.

Bryan: As an entrepreneur, it’s a midnight-to-midnight job. Only one in 20 make it, what is your defining unique selling point?

08:19 | MVP


Bryan: I knew we were great technologists.

Bryan: I had no clue that when our Chief Digital Officer (Gerbrand Potgieter),  phoned me in 2019 saying he's built our MVP, I was like, Gerrie I'm the MVP. He's like, no, Bryan, we're in the tech industry, that’s a minimum viable product.

10:04 |Learn to fail fast.

Dov: I love this lesson around unlearning. You were top of the world, you had won the 2007 world cup, you were the highest scorer. How do you unlearn that?

Dov: The ability to unlearn is such a valuable lesson for entrepreneurs. If you are not fluid, if you don't have agility, if you are really stuck and rigid in your ways in a world where it is ever changing, then you lose your edge.

Bryan: the successful entrepreneurs have, I think, a sort of common thread. If they fail, they fail fast, but they learn faster. And I think as an athlete, we always had this next job mentality because I couldn't rest on my laurels about knocking a ball on because the next phase of play was happening.

14:23 | Growing Paymenow

Dov: Fintech and rugby aren’t obvious bedfellows. Paymenow is doing millions of transactions, has got hundreds of thousands of customers.

Bryan: Our CEO Deon (Nobrega) came across the early wage access concept. He had financial services and tech experience and I had the brand. Seven years later, we have about 750,000 employees on our books, process 1.2 million transactions a month, and over 26 million transactions in six years.

Bryan: We have made a massive merge with PayCurve.  

21:38 | The Kaizen Principle

Bryan: There is a correlation between sports and business. How do you become 1% better every day?

Dov: The Kaizen Principle is a Japanese Principle focused on continuous improvement.

Bryan: That's where I think CEOs become instrumentally key because a lot of the most successful CEOs don't look at the now. They understand the potential needs to be a fix for the now, but they see the long-term vision.

Bryan: Heyneke Meyer had this phenomenal thing that was like key theme for us in the build up to 2007. He said, if you want to be #1, train like you're #2.

Bryan: Rassie made it so fundamentally important that no individual is bigger than the team. And I think that's what the best CEOs do.

26: 26 | Raised in Privilege

Dov: We are both fathers to two young boys. How do you bring your boys up in this world of instant gratification? I heard this saying, how do you make sure that the luxuries of today don’t become your kids’ necessities of tomorrow?

Bryan: I was very privileged in comparison to people of color in South Africa at a stage where it was really difficult in the early 90s. I was brought up in privilege. I see myself as South African because I wasn't worried about the color of my skin. I was just worrying about being a great South African. And I'm really grateful that sport has given me that.

Bryan: If I look back at my upbringing, there were levels of me needing to unlearn the example of a father that I shouldn't be. And I think there's a real difficulty, particularly in male society around, we're almost not willing, because if that's all we've ever known, and you're not going to do something different to change it.

Bryan: I think one of the key successes of life is who you choose to spend the rest of your life with.

And Janine has been fundamentally life-changing for me, because I think firstly having someone that's always in your corner, but someone that can keep you accountable to who you are, but it's also been actually very different of, and I think ever since we've met, she's constantly challenged me in ways in which no one else challenged me.

Dov: I couldn’t agree more around picking the right partner. Having the right spousal support in one of the top things you need as a founder.

Bryan: If I can teach my kids discipline in how they approach life. Sacrifice, hard work, resilience and perseverance. Those are non-negotiables from a sporting context that if contextually applied correctly in the real world will mean success.

41:56 | Looking Ahead: Delivering Respect

Dov: A final question, which I ask every guest. When you are 80 and look back at your life, what would you be most proud of?

Bryan: I want to be remembered as a person that constantly delivered respect everywhere he went. I've been very fortunate that rugby defined me to other people, but I tried to not let it define me as a person. And I think when I walk out of rooms that people feel better because I was in there.

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