My conversation with Dan O'Malley, CEO, PerkStreet Financial

Last week, I had the pleasure of having breakfast with Dan O'Malley, the CEO of PerkStreet Financial. He had a very fascinating story to tell as a first time entrepreneur who closed his first round of funding within 6 months of starting, and an uncommon passion and willingness to walk off the edge of a cliff in order to pursue his dreams. That really resonated with me.

Dan was a senior executive at Capital One before he launched PerkStreet last year. At Capital One, he successfully introduced the decoupled debit card. A decoupled debit-card is is so-called because the cards are issued by Capital One but they are linked to checking accounts held at other banks. When he then came up with the idea of offering a debit card with rewards, there was a conflict of interest within Capital One that prevented the idea from being pursued, even though he had the backing at the highest levels inside the organization. Something Dan said at this point put things I was pondering in perspective for me:

"Regret is a powerful emotion. I did not want to regret not taking the chance and watch someone else build my product".

That is the passion a founder must feel! When he said that, something cleared in my head and I knew the choices I had to make. An entrepreneur must feel that kind of burning need to act on his vision in order to have a chance of successfully navigating the challenging, arduous path to the finish line.

Dan also said something else that really stuck in my mind. I asked him about the highs and lows of his entrepreneurial journey so far. He offered a philosophical response - it's dangerous to be swept to the peaks of happiness or be overwhelmed by setbacks, because higher the peak and lower the trough, farther the fall to the bottom. The key is to maintain a somewhat neutral steady-state, that allows you to wake up each day and roll with the challenges the day brings.

How very true! Dan said this so much better than I ever could have, and the point really struck home.

It took me forever to learn this lesson, and I am still working on trying to maintain a steady-state at all times. Some times I am more successful than others, but I suspect it's a very important lesson for me to learn and master in my journey as an entrepreneur.