Harper Reed might be best known as the first ever CTO for a US president, helping Barack Obama to win a second term by creating a slick digital marketing campaign back in 2011.
He’s also the oh-so-recognisable owner of the least political get up that may have ever crossed the White House threshold – beard, thick glasses and all – more suited to Shoreditch than Capitol Hill.
But today Reed sits as the CEO of one of PayPal’s latest acquisitions after his Chicago-born ‘contextual commerce’ company Modest gets absorbed into the online payment giant’s ever-expanding global infrastructure.
Reed’s small team now shares a floor with hundreds of other people, including the team behind Braintree, another Chicago startup, which was acquired by PayPal back in 2013 and whose mobile payments ads can now be seen on billboards all over London.
Tech City News spoke to Harper Reed ahead of his London appearance at Braintree’s event this evening: Code. Ship. Repeat. From Startups to the White House and Back.
So what do you think of the London startup scene?
Like many of the startup scenes around the world, and Chicago is very similar to London – we had to find our own way – we had to figure out why we existed.
Chicago is going to be Chicago and make Chicago-style companies. I think Braintree is an example of these companies that are very good but kind of secret until they’re not secret. No one talks about it and all of a sudden they’re taking over. And London has its own type of company it creates as well.
I don’t want to be San Francisco, I want to be Chicago because that’s where I live.
If you talk to famous entrepreneurs like Michael Acton Smith or Richard Moross, the new guard of the London entrepreneurial scene, I’m sure they would have the same idea – that they do it London-style not San Francisco-style and I think that’s what’s exciting right now.
What have you learned since you started, has the global startup scene changed?
At first everyone tries and figure out how they are compare to Silicon Valley and so you get Silicon Alley, Silicon Prairie and Silicon Roundabout.
I think that these are fake and I think they’re fake because what it is trying to emulate has this historical and cultural identity that somewhere like Chicago or London doesn’t have.
So what I’m excited is for that conversation to die. And that’s so they aren’t talking about Silicon Roundabout, they just say they have a nice office space in East London near other startups.
It’s more organic and it’s more about finding the community that you live in instead of a forced community of jealousy, which I think is how it starts. It’s not “why can’t I raise money in Chicago? I have to go to San Francisco”.
If I wanted it to have Chicago be like San Francisco I’d just move to San Francisco, which is a great place. It’s just I live in Chicago. I want Chicago to be Chicago but I want that same opportunity.
And as Chicago has more startups that are successful it’s creating more opportunities for entrepreneurs. As the financial markets stay the same, more people are investing into private companies, which means it’s more interesting, there’s more angels.
And this seems to be the thing that’s happening in many communities across the world – whether it’s Singapore or Indonesia – there’s a lot more private investing and I think this is leading to better communities that aren’t just trying to copy the magic of Silicon Valley.
And with the internet and communication we all get to see what’s happening in Silicon Valley so we can learn from it but don’t have to replicate it for success.
Lots of startup communities have a diversity problem, how do you get diversity right at a startup?
My view on diversity is very straightforward– I think that no one actually tries to hire diversity. As you know I’m a white man and it’s very easy for me to say “I really like diversity” and then not do anything about it. That’s a cheap thing to do. It’s actually hard for me to say “I think diversity it very important” and take action.
We have spent a lot of time over the past two years understanding how you can hire a diverse team because the fact of the matter is that there’s a lot of people out there that may not fit the profile of what a lot of people want to hire into tech.
And we’ve found that honestly that profile largely was bullshit, because the profile is usually they went to the same school as me. The profile is usually a men’s club profile. I love clubs, I think they’re great, but at the same time I also want people to come in and build products on my team with me that are much different than I am.
Because the products are for the internet and the internet is a hyper-diverse place. And if you don’t have a team that represents that diversity then your products aren’t going to represent the internet and they’re not very not going to be very good.
That’s the thing that is really important – getting that stuff set.
What practical things have you decided to do?
There’s this really great project called Job Lint and the first thing it does is it removes gendered language from your job posting. It looks for things like ‘he’ and says use ‘they’, use non-gendered pronouns.
The second thing is, you shouldn’t say thing like “dude come join the tech bros” or other very aggressively gendered things. It’s absolutely terrible and it happens all of the time.
That’s the thing that we really need to solve absolutely immediately – but it’s not so straightforward. Inclusion is hard.
One of the other things we did which is really important was we went ahead and made a decision early on to change our interviewing process. We made it so it’s less about the brainteasers, because no one in the world has ever worked with brainteasers when you join work. So we tried to make it much more accessible.
We’re also really strong on remote culture and flexible work hours because that’s how you attract people that have different life expectations. We made sure that remote work is ok, which means that sometimes your interviews are also remote.
How are governments taking on the principles of startups?
If you’d have interviewed me in 2009, I would have talked about how the most exciting thing I’ve done is sell t-shirts. That was pretty exciting, it was a lot of fun, but it’s not helping anyone. I probably had this desire to help – and now I can solve that problem, I’ve done that. And I think that happens in a similar way to many technologists.
UK Government Digital Service or US Digital Service, which is bringing startup folks into government, is kind of solving this problem.
It’s also a point of privilege. The people who are working in those organisations are people who have had a lot of success in their career and it’s really awesome.
Are digital governments where they should be? Should we all be voting online?
It is good that these people are there, they’re where they should be, but that doesn’t mean we should turn everything into technology. The reason for that is you can’t do anything without people and often we think we’re just going to replace people.
What is most exciting you right now?
I’m a terrible prognosticator and I have no idea what the future is but I’m very excited about and I think there’s going to be an opportunity for some really neat security. Because we live in world of both surveillance and a world where we need to be more secure. So it’s exciting and hopefully our governments don’t accidentally ruin that for everyone.
I personally have a lot of hope around the internet of things and I think that right now we’re just seeing the veneer of what we can do with it. Last night I was able to change the music playing in my house by just speaking, that’s pretty cool. And that’s just the top, that’s the surface. And I don’t think it’s as silly as we see it now.
It’s more about when you start to think of factory floors and you start to think of how much intelligence factories have, when this part is going to break or when this piece is going to need replacing. Or all of these great sensors around us being able to work together to create a better picture of what’s happening so that we can be more healthy. There’s a lot of opportunities for that and that’s why I’m very excited.
What’s the journey been like from the beginning to Modest getting bought by PayPal?
We built this really amazing product called Modest and when you’re in a place like Chicago or London, one of the things that we constantly did was showed off what we were building and what we were talking about.
The side effect of that which is actually really exciting is that I got to spend a lot of time with Bill Ready who is CEO of Braintree.
And the last time we had that conversation with him it just became clear that we were focused on very similar things and he said “you know, is there a way we can join forces?”.
Next thing you know I have a PayPal badge and we’re basically doing the same type of thing but with a huge, huge, huge set of customers, which was amazing and that was the real secret.
We’d built this amazing product and we wanted to add customers and we were like “wait, how do we do this without a four to five years slog because we want to get there fast because we think the opportunity is now?”.
And so this acquisition was all about that cheat code, as I like to call it, like when you’re a kid and you type in that cheat code and all of a sudden you have these superpowers where you can get ahead.
Do you worry about losing the startup vibe?
That’s a very good question. Starting a company is a very ego-based thing because you think you can do something better than anyone else and a lot of it comes down to your power and your decisions. But the acquisition has allowed me to not focus on these big scary decisions like how we’re getting money or revenue.
It means I can focus on the things like product, how do we get customers, to solve contextual commerce rather than making sure that I pay salaries. The decisions have changed.
The only downside thus far is that when we were in our own little office we could play whatever music we wanted and we often played terrible music. And now that we have a couple of hundred more people, it’s a little more tricky to find consensus around that so it’s a little more headphones.
But PayPal has done a very good job of making sure that the Braintree team is able to keep its culture and then the Braintree team, because they went through this themselves, are able to understand that they should do as much as they can to help Modest keep our culture.
It’s been very positive and we’ve had a lot of support and people are excited about the product which means that they’re excited about getting this done in a real way, which means that they’re ready to invest, so that’s the thing that we’re most excited about.