Purpose: Company blog content for Simple, an online banking startup based in Portland, Oregon.
My role: Content Marketing Specialist

In July 2009, Josh Reich emailed his college buddy Shamir Karkal with a very direct subject line—“Let’s start a retail bank”. Seven years later, Josh looks back over Simple’s progression and takes us through the lessons he’s learned.

Simple is celebrating its seventh anniversary, and CEO Josh Reich has a lot to celebrate. Simple started as a company of just two back in 2009, and has since grown to a little over 300 staff. This success hasn’t always come easy, however—Josh says he has learned a number of lessons over the years that have shaped where Simple is today, and where it is headed in the future.

So, to celebrate seven years as a business, we asked Josh about seven lessons he’s learned in his time as CEO.

1) Don’t pop the champagne too early

Josh learned the importance of patience pretty early on in the game. It all started when Josh sent an email to his college friend Shamir Karkal, with the bold subject line, “Let’s start a retail bank”. In it, Josh says: “What would it take to start a really boring, simple bank?” At the time, Josh saw a bank’s functions as, among other things, “a place to hold my money so I don’t need an oversized wallet or mattress”. He also thought that the bank he was using at the time had a “terribly obtuse” interface that made it difficult to “rationally choose banking products”.

Around the same time, Josh took to social media to vent his frustration at banking alternatives in America, which failed to live up to the advancements banking had made in his native Australia. This frustration stirred the interest of a venture capitalist, who would later see Josh’s email to Shamir, and request a meeting to discuss funding.

Josh says, “We met with them, they said they’d fund us, and then Shamir brought a bottle of champagne over to my house to celebrate. I told him it might be a little early to pop the champagne, and that we should wait for the check… it was another year before they ever actually offered to invest.”

2) Learn their language (even if you’re both speaking English)

During Simple’s fundraising phase, Josh and Shamir met with more than 100 venture capitalists. One such offer started out promisingly enough, but there was one problem.

Josh says, “This venture capitalist only invested small amounts, in the thousands. That was fine, but he added in, ‘Come back when you have a thousand customers, and then I’ll consider writing a check’. At this point, we needed to raise a couple of million to get even customer number one, let alone one thousand. It was clear that banking was very foreign to technology investors, and we’d have to meet them where they were.”

Josh and Shamir thought they’d reached a similar impasse when top venture capitalist Matt Harris, who said very little during the pair’s initial hour-long pitch with him. Matt didn’t reach out after their meeting, either, which left Josh and Shamir assuming the worst. Josh recalls, “I ran into him at a party a few weeks later. He casually came up to me and said, ‘By the way, just wanted to let you know that we’re in.’”

As it turns out, learning to speak the language of venture capitalists like Matt was exactly what Simple needed. “Getting the seal of approval from a well-respected person unlocked a lot of potential for us, and to this day, Matt Harris remains on our board of directors as our chairperson.”

3) Let your ego get in the way (no, really)

Shopping your business around for venture capital is tough going. During Simple’s fundraising phase, Josh and Shamir had more than a few doors (politely) closed in their faces. But instead of getting down, Josh says he and Shamir had one thing that kept them going—pride.

“In the face of things that were failing, the thing that kept Shamir and I going was not wanting to lose face in front of each other,” laughs Josh. “For example, before we finalized our first bank partnership, we had three other partnerships lined up, and they all flamed out for really heartbreaking, and potentially soul-destroying reasons. But we didn’t stop, even when things went from Plan A to Plan… Q.”

Josh says, “We worked it out with a little bit of ego, tenacity and trust between the two of us. We decided that we’d told people we were going to do this, so we better get it done. If I was just doing this by myself, I wouldn’t have gotten anywhere.”

4) Don’t fear the suits

He’s now known internally as “Actual Saint”, but when VP of Operations Brian Maher showed up for his first job interview in a suit, Josh joked that Brian was bringing with him “the end of optimism”. Instead, Josh found that bringing people from the banking industry to Simple had a few spirited flow-on effects: ideas, process, and yes, even optimism.

“Once we were able to see past the suit,” laughs Josh, “we saw the potential of having people come here from the world of banking. “They had an inbuilt understanding of how to do things, what we were up against, and a desire to help create culture within the business. People like Brian Maher really unlocked a level of optimism that we hadn’t seen up until that point.”

Josh says, “I think it’s all-too-easy to come up with ways to make yourself feel smart, and to give yourself reasons why you shouldn’t do something. It’s okay to push those feelings aside from time to time, and try something different. When it came to hiring someone like Brian, it worked out.”

5) Leap, and the net will appear

Not long after launching to customers in 2012, one of Simple’s main features was ready to ship. Goals were working perfectly in beta, but Josh was nervous that the new feature would take a lot of education in order to get off the ground.

“We’d been talking about making an animation or a video, or maybe even a how-to page, but we just couldn’t find a good way of explaining it,” says Josh. “In the end, we just turned Goals on for our customers. No explanation, nothing; another tab just suddenly appeared on their account page.” Josh says, “By the end of the day, when we went back to check, customers had flocked to Goals in their thousands, and were already using the feature without us needing to explain it. The lesson there was that we shouldn’t feel like we always have to have the right way to ‘message the product’ down; sometimes, if a feature is really cool, people will use it, and like it.”

6) Take your time

Over the last seven years, Simple has released a number of features, and each time, Josh says the company has become better at staging their rollout.

“We learned a lesson a few years back that flipping a switch isn’t the best way to drive the business forward,” says Josh. “We like gradual rollouts—we like testing, learning, and setting up metrics for success in advance.”

Josh says, “One of the lessons we’ve learned is that unfortunately, gradual rollouts of new features aren’t sexy. It certainly feels exciting to be shipping big new features, but so far this year, we’ve been shipping small things that help customers on a day-to-day basis. It’s hard to keep saying that the big things are coming, but they are; they’re just being properly tested and rolled out. We’re not flipping a switch.”

7) Take time… for yourself

If there’s one lesson that Josh wishes he’d learned over the past seven years, it was one given to him by original board member Jerry Neumann when Simple was starting out.

Josh says, “I remember speaking to Jerry, and telling him, ‘I’ve got nothing to do today, and I feel guilty’. His advice was, ‘Don’t worry. Instead, recharge and enjoy today, because in three days’ time, you’re going to need the energy you’ve saved’.”

Looking back now, Josh admits that he’s learned to cope better, and that having a larger company means there are more people to share the weight of the to-do list. He says, “When it’s your first time on a rollercoaster, you might feel sick or anxious, but once you’ve been around a few times, you don’t feel sick any more. I’ve learned to stop running on adrenaline, and constantly thinking that something’s going to drop out from under me. However, I think if I had to go all the way back to the beginning, I’d have spent more time with family and friends. Jerry, you were right.”