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From High School Dropout To CEO of Sequoia Backed Startup

After getting out of my comfort zone and starting to write more (thank you for pushing me, Maya Grossman), I began receiving questions about my background. People were curious how I went from dropping out of high school to founding two companies, and most recently, raising money from Sequoia Capital. 

Here’s my journey in a nutshell. 

Real-Life Experience > School 

When I was younger, you could say I was never really motivated by education, outside of math and design. For me, it wasn’t mentally stimulating. At thirteen, I started selling mixtapes—those were the Limewire days for anyone who remembers. I’d get requests from people over MSN, burn mixtapes, and then sell them for £4 (the equivalent of $5). Sometimes, I’d sell 100 of them in a week. Even at that young age, I was learning a lot about business and entrepreneurship. 

Over the next couple of years, I continued to sell different things from truckloads of clothes from Abercrombie & Fitch to buying and selling mobile cell phones (when Nokia banana phones were cool). But when it came to exams and doing homework, I just didn’t really understand the value. 

I was learning more through real-life situations where I was negotiating, building relationships, and ultimately learning how to interact with people from all walks of life. That to me was valuable. 

During this time, my friends were deciding where they wanted to go to college and this didn’t connect with me. My parents never pushed me to go to college. And, when I shared my dream of building my own business, they laughed at the idea. That led me to consider being an architect. Why not? I liked numbers, art, and design. It seemed like a great match. My parents said as long as I could get a job they would be supportive, and that was enough for me. 

I failed all of my exams by not showing up. Of course, my parents weren’t very happy about that (and rightfully so). At sixteen, I had nothing but sales and people experience but struggled to find a job for months. But this didn’t stop me from trying. Then came my break—I joined a recruiting company in London as a trainee in 2006. 

First Job & Beyond 

I was so grateful for the opportunity. I will always remember my dad telling me to be a sponge and absorb as much as I can from the highest performing people. I did exactly that. I was obsessed with learning. I probably asked more questions than anyone else, to the point my manager would ask me to batch my questions daily. My manager taught me that with a great attitude, resilience, and hard work, you can accomplish anything you want. I still have this mentality today. 

I will forever be grateful for my first two managers. Even as hard and direct as they were, it shaped me to be the best version of myself. So what did I do? I helped software engineers find jobs at investment banks. I loved it. I was speaking with much smarter people than myself and helping them navigate their careers. I found this so rewarding. 

Then came 2008—the financial crisis. The whole market crashed, thousands of people lost their jobs and I was shocked. I was an eighteen-year-old in my first job and I was seeing thousands of people lose their jobs. It was an emotional time for everyone, and it allowed me to really appreciate life and work even more. 

It also was a time that became a huge opportunity for me. Everyone wanted help from recruiters, and especially in banking. This became the birth of quantitative trading (electronic trading in simple form)—the art of math and technology to automate what a human would usually do when it came to trading on Wall Street. 

This is when I started to have success and was placing 20-30 people a year into Goldman Sachs, JP Morgan, and several other investment banks. After this, my managers approached me to join a new firm they would be starting. At first, I shared my concerns with them. But instead, this turned out to be a place where we created the culture, one around collaborative recruiting. It was less about competition internally, and more about togetherness and helping each other to leverage our relationships. Through collaboration, we achieved greater success for our clients and candidates. 

We scaled the company to twenty people in two years and began working with some of the most elite quant funds in the world, from Two Sigma Investments to De Shaw. You name it, we worked with them. This presented a huge opportunity for me, and after being offered jobs internally by several clients, I proposed something else. I offered to exclusively serve them and they would pay me upfront (retainer in recruiting terms). They were completely on board. Two clients gave me $250,00 and with that money, I built my own recruiting firm at twenty-one years old. 

I remember asking my Dad if he wanted to invest but he said no, stating, “You’re not ready.” This became my biggest motivator in my career. Still to this day I remember the conversation vividly. 

Becoming A Founder & CEO 

I was scared and excited but I knew there wasn’t much to lose. I had confidence in my abilities and what I’ve accomplished and now I could build my own business. This company quickly grew and went from a former colleague and me to 10 incredibly motivated and driven individuals. We were serving around 8-10 quant funds and the success we had with Two Sigma quickly got around and more companies started reaching out for help. It got to the point where we had to turn away business to focus on quality over quantity. You never want to over promise and under deliver. 

As we grew, we took on more business at the peak in 2016. By then, the company was 20 people strong, turning over $14m. I was twenty-six-years-old, recently married, and had more money than I knew what to do with. This is the time I reflected on everything I had achieved. You could say it was my mid-life crisis, ten years into my career as a recruiter and more recently, a CEO. It was tough because as much as I thought I wanted all of this money and success, it became meaningless. All I really cared about was building something successful that helped people in a positive way. Nothing and I mean nothing, feels better than placing a candidate in a new role and them telling you how happy they are. That feeling was why I did the job, especially the ones that said no at the beginning. 

During this time of reflection, I realized what I had learned was pattern recognition and how the industry as a whole is broken. I was helping companies build a more biased and less diverse workplace. I’m sorry to say it but these firms only cared about pedigree. As much as they shared with the outside world and public about diversity, I saw they really didn’t care. I tested it over and over again and witnessed so much, that to this day I couldn’t believe it. From helping one company hire their first black engineer at 150 people to later go on to fire this person, accusing him of accessing a private file and having the FBI break down his door and fire him all within 24 hours. 

It’s sad to say, if you didn’t go to Harvard, Stanford, MIT, or Cornell, they weren’t really interested in you. This showed and still shows today with companies having “target schools.” What even is that? They only speak to people from certain schools? It’s clear the industry was and is still broken.  

Nobody had really done anything about it. And that’s when I decided to start my next venture. 

I would continue as an investor at the recruiting firm but wanted to now help millions of people find a meaningful career and finally hold these companies and recruiters accountable for their actions. And in 2017, Canvas was born. 

You might be wondering, why? What’s the reason? The real catalyst was the birth of my second daughter in January 2017. I want my daughters to grow up in a world where they are not judged for the school they went to or where they worked. It should be about who they’re as people and what they can bring to an organization based on their interests, passions, and values. 

It was time for a change. I had felt and seen these biased behaviors for way too long. Platforms were enabling recruiters to source and spam talent on LinkedIn, focusing on Boolean search strings that look similar to this: “Google” and “Stanford” and “Software Engineer”. Think about what this is doing and how many people you are simply missing out on. (I’ll talk about this more in another article on recruiting and the secrets behind internal recruiting teams.) 

Canvas grew and we raised $2m in a seed round, and then later raised our Series A from Sequoia Capital. It was a real dream come true for me. You could say I was biased and you’d be right.  Everyone told me if you raise money from them it shows credibility and is the best VC in Silicon Valley. During my Series A fundraising, I only spoke to Sequoia Capital (most Tech CEOs will laugh at this), but I learned a lot. You could say it was a one-shot wonder, but I’m really grateful for the experiences I’ve had and they’ve been a great partner to me and the company over the last two years. 

We are growing at 3X revenue YoY and we’re working with some of the most incredible companies in the world, from Airbnb to Twitch. We’re working with companies that care about diversity and aren’t just talking the talk but walking the walk. We are holding organizations accountable and we’ll continue to do that more and more as we develop the most complete diversity recruiting platform that gives everyone the same access to opportunity. We’ve helped thousands of people find opportunities across tech and finance and I won’t stop until we help millions. 

The Take Always & The Future

Don’t give up—People will tell you it can’t be done and will try and bring you down, as that’s life. Don’t let that stop you. Be resilient and always have the attitude that you can do it if you commit yourself 100%.

Follow your passions—There will always be options and possibilities but don’t let others affect your opinions. Stay true to yourself and your core values and hold yourself accountable to them. 

Fail, learn, and grow—You have to fail. Don’t overthink things. Just take the leap of faith. It gives you so many opportunities to learn and grow-make sure you take them! 

With all this being said, find good people to work with who are genuine and great teammates that will always help you grow and be your authentic self without being judged. Things will change and need to change, but it takes us all to stand up and have a voice regardless of our own individuality. 

We are the future, you are the future.

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