The 1st of 3-part mini-series with be inspirational Ysiad Ferreiras in Tech Open Air, Berlin. Rose from a difficult environment to making a lot of money trading hedge funds, went to India with financial independence but quickly fell into depression and realised he needed to seek out a higher purpose, worked his way into the world of tech – all the way to success as the COO and 6th employee of Hustle in Silicon Valley, a peer to peer texting platform for conversational marketing. He helped scale it from nothing to 130 people, $16M ARR (annual recurring revenue) and $42M in investment before leaving them. “In the US I’m an ethnic minority, being a Dominican America, and my family’s from the Dominican Republic. English is my second language. Spanish is my first and I grew up on public assistance in a single parent household. At the age of 15, I was arrested for gang related activities. That’s also pretty atypical that someone can bounce back from that sort of childhood and make it to be a leader in tech, and enterprise SaaS specifically.”
Transcript of Mini-series, part 1
Ysiad Ferreiras talking with Stephen Cummins
Welcome to 14 minutes of SaaS, the show where you can listen to the stories and opinions of founders of the world’s most remarkable SaaS ScaleUps.
In the US I’m an ethic minority, being a Dominican America, and my family’s from the Dominican Republic. English is my second language. Spanish is my first and I grew up on public assistance in a single parent household. At the age of 15, I was arrested for gang related activities. That’s also pretty atypical that someone can bounce back from that sort of childhood and make it to be a leader in tech, and enterprise SaaS specifically.
Welcome to 14 minutes, the show where you can listen to the stories and opinions of founders of the world’s most remarkable SaaS ScaleUps.
This is the first three part Mini-series with Ysiad Ferreiras, ex COO and third employee of Hustle, a peer to peer texting platform for conversational marketing, which he helps scale to 16M in annual recurring revenue. Ysiad talks about the power of reading to transform one’s life and how living like a King in India revealed to him that there’s no escaping the fact that he’s wired to work, build teams, and to live meaningfully. This interview took place and Tech Open Air, Berlin.
Hi, Ysiad. It’s wonderful to have you with us. Thank you for being here on 14 Minutes of SaaS, in Tech Open Air Berlin – otherwise known as TOA. You’re a statistical anomaly, but an inspiring one – tell us your story!
Sure. I mean, given we’re talking in Tech Open Air, and you’ve got a SaaS podcast, I think probably what’s most relevant is the stuff that I’ve done in SaaS, and so regardless of where I came from – just being a C level executive at a company and taking it from zero to at this point right about 16M in ARR. And it took us a little over two years to get there. That itself is extremely rare.
First, you know, the character attribute is hustling but the name of the company as Hustle … Hustle. And yeah, that’s it’s… it’s extremely unlikely. And especially the way we did it, selling to non-profit, advocacy organizations, labour unions, political campaigns etc. It’s only now but we’re really going into ‘for enterprise’ use cases. But yeah, you’re right, it’s a statistical anomaly.
But then also, what I’m sure you’re referring to, is my background. Very rarely are silicon valley executives people who are, you know, come from the sort of background that I have … which is…. In the US I’m an ethic minority, being a Dominican America, and my family’s from the Dominican Republic. English is my second language. Spanish is my first. And I grew up on public assistance in a single parent household. Additionally, I’m pretty public dan open about the fact that at the age of 15, I was arrested for gang related activities. That’s also pretty atypical that someone can bounce back from that sort of childhood and make it to be a leader in tech, and enterprise SaaS specifically.
I think it’s a great thing. And the thing is, you know, I did research you, and, you know, you are the real deal when it comes to actually escaping from a difficult environment. I grew up in Tallaght myself in Dublin, which is not the nicest part of the city, but I don’t think I had the same amount of barriers as you had, because you had the whole racial thing in the US as well, which I don’t think is as strong where I come from. If you were to name one person that’s influenced you Ysiad, in your really quite remarkable career of multiple exits, successful exits, who might that be?
That’s an interesting one .. Who’s influenced me? I think it who influenced me has changed as I’ve gotten older. When I was younger, one of the biggest influencers was this guy, a friend’s dad? And actually at this point, I honestly can’t tell you even like what his name is. Actually, no that’s not true. I believe his name is David Barg – because her last name is Barg. He recommended that I read the book ‘How to Win Friends and Influence People’ when I was 14 or 15 years old. And that book let me see that you could read a book and just learn basic social and business goals. And from that point on I was addicted to, at that time Barnes & Noble was still a thing, and you could just show up at a Barnes & Noble and they’d have all these top selling business books and I would just read them. And that had a tremendously positive impact on my life. And that was very helpful.
And then more recently, I spend a lot of time reading Saastre, Jason Lemkin’s blog, and that was very useful. It helped me understand sales funnels in a deeper way than I understood before, and also the challenges of growing and scaling a SaaS business. So I found Jason Lemkin’s blog to be really helpful as well.
Yeah he scaled Echosign battle with Docusign. And the two of them pretty much carved up, without any real technological differentiator, they pretty much went to market very efficiently and carved that up. Impressive guy. From talking with you earlier, you definitely have a low boredom threshold. That’s a sure sign of a healthy level of curiosity, a keen intellect. Would you describe yourself as a patient person?
I think I would describe myself is that …. if you ask somebody that I’ve gotten impatient with, they might not describe me as a patient person. But I think typically, I’m thinking … as long as I’m learning or somebody who I’m working with who needs to learn is learning from an interaction, then I can be pretty patient.
Okay, very briefly just to take it to some of your formative experiences … What did you learn in your time as a successful founder of Aardvarkium and Managing Director of Jake Roy Pillar.
That was a fun one so. I started Aardvarkium while I was splitting my time between India, New York and San Francisco. So previous to that I was working in the hedge fund space. And was pretty fortunate how that turned out for me. And so I was just like ‘hey, I’m gonna just spend a few years traveling around’ and I lived in India during that period. And some friends and I had started this thing called the ‘International Day of Happiness’ which is now an international holiday that got passed by the UN. It just started out as this idea that we had.
But anyways while I was doing that, I needed something to do, and so that was Aardvarkium. I called it that because I was starting this company and I figured well when somebody is doing their job and evaluating different companies, they might list the companies in alphabetical order and I always wanted to be at the top of the list – because I know for myself when I evaluate companies, I usually get bored. Or impatient or other priorities come up. So I only end up evaluating 3, even if I fully intend to evaluate 7, 7, 10 … right? And I figure everybody else would be in the same boat. So that’s what I did there. And Aardvarkium was … we did some software development and made some product, but then the person that I’d worked with previously at Ryan Associates … his name’s Charles Walters. He was my boss there. I tried to hire him to be the CEO of Aardvarkium. I wanted him to be my boss in my new company, and he said no.
He was like ‘No, like there’s no way you’re going to hire me to boss of your new company, but how about I started a new company and I’ll buy you!’ And that’s what Jake Roy Pillar was. So we started Jake Roy Pillar, bought Aardvarkium, and then we worked together and I was a managing director at his new company which quickly grew in scale to having something like 30 of the top 100 hedge funds as clients. I personally made a data warehouse solution that was used by several of the top hedge funds on the planet.
And in the process of doing that, I started getting real exposure to enterprise sales. What I found was that I had a much easier time hiring and training software developer skills, especially in the hedge fund enterprise software space than I did competent salespeople. So then I got enamoured by the sales and marketing challenges of doing enterprise sales to hedge funds. And then that’s when things really started going for me … you know developing that side of things. Before that I was primarily focused on software development. And then only really using the stuff that I’d learned in these business books that I’d read as a kid to do sales. This is a whole different beast.
I’m fascinated by the fact, I spent four years when I have my parking so fascinated by the fact that you… you speak to spend a lotta time in India and perhaps other places traveling the world. Did you… did you have time to sit back and reflect as well as do all this stuff you were doing like in this day and alone.
Yeah, totally. I mean like that was the bulk of it, right. So mostly I was thinking cool …. I’m 25, I have all this money. I’m done. I’m just, you know, and I was … but it turns out that, you know, so I was living in India and I won’t go into a bunch of my personal details … But it was like I was in a very excellent situation, but I got depressed when I was there. I just didn’t like being there …. within just even a few weeks of being there, I just turned into this completely different person who was depressed. And I realised that well … I just need to work. That’s just how it wired … and to embrace that. And that wasn’t what happiness was going to be for me. So then of course, ironically, while I was depressed I started the international Day of Happiness with some friends. But yeah, I would spend a lot of time hanging out not really doing much and that just drove me absolutely insane. And that’s how I learned that I’m just driven to work. And that’s my purpose. I like solving business challenges. That’s my form of art. That’s what I do.
And I think that probably really feeds into the talk you gave today which was excellent … the Maslow’s Hierarchy [of Needs] based reflection on how to bring someone up above the bottom two layers, and then bring them through. And you didn’t just apply that to yourself. You applied that to building teams. And to enabling people to be the best they could be. Also managing out people who couldn’t maybe fit the culture of the company. Tell us a little bit about how you did that at Hustle … and what sort of scale you got to in terms of personnel. Yeah, sure … So when I joined Hustle, it was a five person company that was all engineers. And they had a couple of unpaid pilots, but no real revenue. And then so I joined as the sixth person or the third employee [he means the 3rd non-founder] … and my mandate was to build a business around these developers.
Now couple of years later, we’re about 130 people. We’ve raised over 40M dollars. Most recently a 3oM dollar series B. I’m the COO of it. And now there’s like maybe four layers of management, right? So, you know, before it was extremely flat or maybe one person reported it to me. Now there’s, you know, like somebody his boss’s boss’s boss kind of thing. So something that I’m really proud of is … in the process of getting to about 130 people, and we’ll be over 200 by the end of this year, I think we’ve only had to like go of maybe a dozen people … or something like that … so it’s a really low attrition rate. And I think that comes from being very clear about what our culture is. And I get very explicit about that.
So I have this document called the cultural commitments to the business team, for example, because the engineering team’s different … with the business team, we’re very much about very direct communication. We’re very action oriented. And I try to make very clear to somebody ‘Hey, what’s a mistake that we don’t tolerate? … Versus what’s the sort of mistake that I want you to feel free to make … right? So one example, one of the things that I think kills companies is when they get into an analysis paralysis mode on a decision that really doesn’t matter right? Or it matters that they get it, right, but it’s okay for them to fall forward a couple of times along the way. Right? So, in that case, I want there to be fast iterations and I want the mistakes to happen as quickly as possible.
So the way that we do that is I’ll say ‘Hey, you get immunity for any decision as long as you e-mail your manager first, and if you’re aware that somebody else might be a stakeholder, include them in that e-mail. I just say ‘Hey I’m, gonna do this unless you get back to me within some time period … two hours, a day..’ whatever … and then you get immunity for whatever happens from your decision …right? Because, again, what I care about is that something happens … that there’s some sort of activity. And this is how we invest in our people. Right. I want them to make mistakes. That’s one of the best ways to learn… is when you apply yourself and it doesn’t work the way you expected.
In the next episode Ysiad takes us into a deeper dive into Hustle’s value proposition. And explains why his personal superpowers lend themselves to being a COO, as opposed to CEO.
You’ve been listening to 14 minutes of SaaS. Thank you to Ketsu for music provided under a creative commons license. This episode was brought to you by me, Stephen Cummins. If you enjoy the podcast, please don’t forget to share it with your network, subscribe to the series and give the show a rating.