Joseph Benson-Aruna

November 9, 2023

On Regrets

I've always prided myself on not having regrets. I own every decision I make and move on quite faster than most people. But over the past couple of years, I've started racking up a few—three at this point, to be precise. Two of those are related, and I'd like to touch on them a bit.

I regret having to leave Wallets. I don't talk about it much unless you're Seun or, in some cases, Victor, but damn! That hurt like hell. Building that company was something I'd been trying to do for more than 8 years before I finally got to, and then having the opportunity to do so and losing it so quickly was a huge bummer. I basically drifted through 2020 in a very numb state, unable to accept what was my new reality.

In 2010, Iroiso, Obaro, and I thought it would be a great idea to make it easier for us to pay our school fees. Back then, you had to pay cash in the bank, then take a copy of the payment slip to an office at the university and hope that it had been posted and then confirmed. There were many cases where you had to go between the bank and the school bursary multiple times. That process took nothing less than five days if you were lucky. Well, we thought, "Why not make the process simpler?" Purchase airtime to the tune of that amount, get a code from the airtime vendor, input the code on the school website and that's it, school fees paid! I know how ridiculous this sounds now, but back then, NIP didn't exist. We aptly named it Air. But we had no idea what we were doing, and we ultimately got nowhere.

Fast-forward a few years, I'm working in the payments space and even though we have made progress as an industry, things were still complex, especially for end users in the banking space. No one seemed to care that customers deserved ease of use. I spent some years working to make the experience easier at different firms, but I somehow felt that to properly define the experience, I had to own and direct the vision in some way. So when my co-founder showed me what was at the time an MVP he was building, you can imagine how interested I was. It took me almost two years to join fully, but I committed myself to making sure we built a company customers loved and people wanted to work at. And boy, were we making it happen. People loved us, my colleagues were amazing, and even though I was broke as hell, I finally had that opportunity to build the bank of my dreams. Then it ended for me. Just when we were reaching escape velocity, it ended. YC Demo Day was on the 19th of March that year, and by December of that same year, I was out.

I regret not being able to finish what I started. I regret having to leave the most amazing people I ever got the opportunity to work with. I regret not having the chance to execute all the amazing ideas we had as a team.

Okay, that sums up regret number one. Number two: I regret not immediately starting again. This one didn't hit me until Seun brought it up about two years ago. We were perfectly positioned to start again and do it successfully. We blame it on the PTSD we were dealing with at the time, but it doesn't remove the regret. I definitely should have taken another go at it.

All that being said, I'm happy I got to experience all that. I wouldn't give it up for anything. Wait, I'd definitely give it up for a few million dollars. But you get the point. It's hard to put a price tag on all the lessons learned. Now, when I work with founders, I'm actually more useful to them.

I'm grateful my regrets don't weigh me down.