Jay Rosenzweig

Jay Rosenzweig, the founding partner of Rosenzweig & Company, is an expert in designing, building and attracting world class executive teams. Jay, a lawyer by background, earned three degrees at McGill University: Philosophy, Civil Law, and Common Law.  In addition, he completed Roger Fisher’s Negotiation Program at Harvard Law School. He also serves as Director, Canada for the Chief Digital Officer Club & Summit. Jay advises several leading edge organizations, most of them based in California, New York, or Ontario, including: Hyperloop Transportation Technologies, Drop Technologies, Winston House, #movethedial, and more.

Jay is a champion of the cause of gender equality and is active in many social causes. He is on the Board of Directors of Nobel Peace Prize nominee Irwin Cotler’s Raoul Wallenberg Centre for Human Rights. He is on the Board of Governors of Mount Sinai Hospital, UJA Genesis Centre For Innovation and One Young World 2016, the premier global forum for young leaders under 30.



Jay Rosenzweig talks about what helps him get through the most stressful times. He also shares his passion for diversity, mentoring, and humanity, and what it truly means to be there for one another.


What you do in the industry is so needed, especially on the many things that you advocate. Thinking about recruiting based on other factors, such as diversity.

I reached out to you because you spoke about mental health on social media. I know in the tech industry, we are a long ways to go in that conversation. Thank you for being one of those people who is saying that, "Hey this [mental health] is really important."

Yeah, it's my pleasure. Happy to talk about anything you want.


Thank you. I would love to know just how you got here. As I mentioned, your approach is so unique. You are a champion of many causes as well, such as #movethedial with Jodi Kovitz.

Yeah, Jodi is amazing. She is a great friend who I am happy to support. In terms of how I got here: so I'm Canadian; I grew up in Montreal. I studied at McGill for seven years. I did a philosophy degree there and two law degrees. I met a really important mentor in law school, a professor named Irwin Cotler, who is an international human rights champion. Back in the day, he represented political prisoners like Nelson Mandela in the former apartheid South Africa, and Natan Sharansky in the former Soviet Union. He has done amazing international human rights work over the years, and has become a very good friend of mine.

Cotler went on to become Canada’s Attorney General and Ministry of Justice where he enacted all kinds of very progressive laws, including same-sex marriage. He freed more people, who were wrongfully convicted of murders, in one year than any of the previous ministers combined.

One thing that inspired me on the gender diversity work that I do is that he was the first man on the woman's caucus. He also transformed our Supreme Court into the most gender representative in the world. It got me thinking about the status of women in the corporate world.

If you fast forward to today, I'm on the board of his Raoul Wallenberg Centre for Human Rights, a broad based, global human rights organization. Among its activities is the representation of prisoners of conscience, the Nelson Mandelas of today in places like Venezuela, Saudi Arabia, Iran, and China.

Upon graduation, I moved to Toronto. I articled for a firm that represented individuals who were wrongfully convicted of murder. It was a defense firm. I became a member of the bar and then fell into the executive talent management business with a boutique firm. Totally by fluke, but it turned out to be a fascinating business to me. That firm was acquired by the world's largest recruitment firm called Korn Ferry. I stayed on there as a Partner for a few years and eventually ended up breaking away and starting my own firm in 2004. The idea was to bring more customized solutions to the table and take on less projects per consultant. Be less conflicted and just bring more accurate, meaningful, and fulsome solutions to our clients.

We've been fortunate, the vision's been realized. We're doing work all around the world in places like Dubai, Brazil, Hong Kong, and all across North America. We've been described by a leading publisher in our industry, out of Chicago, as the leading international boutique firm. We're often looked at as the alternative to the “big” firms. We're working with some of the largest corporations in the world. We’re working with private equity firms. A private equity firm may buy a $300 million dollar business with the idea that with the right leadership, it would be a billion dollar company. We help them change that leadership to achieve their goals.

Lastly, over the last 5-10 years or so, I have spent a lot of time mentoring founders of earlier-stage technology companies. I’m their go-to on issues of talent management, team building, and scaling to the next level. In addition to the people side, I am able to introduce them to the vast network I have developed over the years, to help them with matters such as business development and fundraising. It's gotten to the point now where I'm on the advisory board of dozens of emerging growth companies. A lot of them are in California (Silicon Valley, San Francisco, LA), New York, and Ontario.

I've been doing a report on women at top levels of corporate Canada for the last 14 years. It has also been a joy to support Jodi as she builds up #movethedial. I met her on a technology delegation with Mayor Tory a couple years ago to Israel. We got talking about the status of women in tech. She was determined to do something about it and she did!


Small world.

For sure. What else can I tell you? I'm on a number of other nonprofit boards in addition to the human rights board. I have a beautiful wife and three kids. I have many interests beyond the ones that I've talked to you about, including music and sports and all kinds of other stuff.


Thank you for sharing all that. It’s interesting hearing your story because you've had such eclectic experiences and worked in different industries.

It's all very interconnected. I don't look at any of the things that I've described as being, "Okay, I do that and I do that." It's all connected.

Even on the recruiting side, I'm helping these earlier stage businesses scale up. The larger corporations are interested in working with me on digital searches. They're looking for candidates who have their finger on the pulse of what's next. I have my finger on the pulse of what's next because of the earlier stage work I do. So my ability to play effectively on the early stage side and the corporate side is attractive to my corporate clients. I'm very involved in the Forbes Impact community based out of New York. Investing in businesses that will improve our world, so that again meshes human rights and business.


You mentioned that you mentor many founders and you are on several boards. What do you see when you advise founders? What are things that you notice or you see differently?

The best thing that I can do is to lead by example, so that founders may observe some of my behavior. Very often, I'll be asked questions, "Do you take time off? If you do, how do you do that and why is that important?" Founders are often asking me questions like that, "What do you do to sort of relax or take a load off?"

As an example, what I've been doing for many, many years, is to go to Miami two times a year. It is a very fortunate thing to be able to do.

I sprint very, very hard and I put in very, very long hours during the course of the year. I sprint to the summer when I take two weeks off with my wife. We go to Miami, we just chill. I wake up naturally without an alarm clock and I catch up with my sleep. We go for nice walks on the beach. Go for some dinners. I find that that downtime is invaluable. The reinvigoration that I experience, as I ease into coming back to work is invaluable.

I'm totally burnt out by the time I get to that, so I sprint to that point. Then I sprint again. Just given the place that I am in my life, I know that is important for me, my body, and my mental and physical health. It's really, really very therapeutic for me.

Another thing I do, if I can squeeze it in is massage therapy. Even in the middle of the day, I'll go across the street and do that. It makes the blood sort of flow through your body in a very relaxing way. It allows you to decompress.

Little tricks like that, I share with founders and they listen. They sort of will come back to me and say, "Yeah, I forced myself to take that vacation and it did so much good for me. I'm actually so much more productive.”


That's amazing.

I also love playing piano. I write songs. I do music, which is a great outlet. I do boxing, which I find to be really, really helpful. No matter how busy you are, you need to schedule things that will help you maintain great physical and mental health.


Thank you for sharing that. This message has come so timely as well. In this past year, there have been many news stories of high-profile executives who have burnt out. A lot of people completely go for the sprint, but have no recovery.

I love that you're such an advocate of that, especially for founders.

Yeah, I also am learning more about mindful meditation. You may have seen there's an article hanging in the boardroom. Director X, the video director who does videos for Drake and all the big artists. We're working on a mindful meditation program in the schools, in the prisons, to address the impulse that inclines one to act out violently.

Studies have shown that individuals who are more apt to violence, their pre-frontal cortex is underdeveloped. It's caused often by years of abuse as a child, neglect, things of that nature. It's been proven that mindful meditation can actually regrow that aspect of the brain and really control violent impulses. The results have been incredibly positive.

I feel like I'm meditating always. That might sound kind of funny, but I feel like I'm always meditating and cognizant of breathing. Being very in the moment. Dealing with stress from a meditational point of view, but not necessarily closing my eyes and closing the lights.

I feel like I am in a constant state of meditation.


I am so curious to ask, what does that experience feel like for you? How would you describe it?

I'll never be that person who is yelling and cursing when I am getting cut off on the road. I look at things in a bigger picture way. It's like, “Okay, so that happened.” We just deal with what happened and move on, rather than waste energy on stress. A lot of people waste energy being angry and being anxious about things that they can't necessarily control.

I just understand that whatever is in front of me, I need to face in the best and most positive way possible. If I'm late for a plane or stuck in traffic. Or if I stumble in business. I just deal with it in the most positive and balanced way that I possibly can.


Yeah, that's really powerful. There’s something about your disposition that’s quite calming, despite the stresses of your work. In those times when you're in the deepest part of your sprint, what helps you ground? What helps you replenish?

There's a couple things. One aspect is, whatever happens in the moment, it happens. Right? There's really no point in being angry, or upset, or anxious. It's like, “Okay, what do we do with this? What's the best path forward?”

That's one piece of it. The other piece is that if I know that I'm doing everything I possibly can for my client and I communicate that in the best way possible, the chips are going to fall wherever they fall. I can sit here in good conscious knowing that we've done everything we possibly can.

If there’s issues, then I will let my client know, "Okay, here's the issues. Here's what we've done. Let's brainstorm if you're not satisfied with this solution, given the cards that we've been dealt. How do we pivot?” It's just a matter of knowing that with the highest level of integrity, in terms of process, approach, and skill, you're doing everything you possibly can, every minute of the day.


I love that there’s such perspective in this outlook. Acknowledging that you're doing your best and just having that dialogue with people. I know that in our industry, there can be a tendency to avoid the elephant. Founders often tell me things like, “I knew what I needed to do six months ago, but I was too scared to tell my VC.” Or, "I was scared to tell my co-founder that we needed to replace him."

My passion with this movement is to build the capacity for brave conversation. To see that happen across our community. It could make such a difference, not just in business but in life. How do you go about having brave conversations?

It's really case-by-case. There's so many elements to it. It's tone of voice. It's how you introduce the subject. It's talking on a level that's not personal because it's not personal at all. It's like, “Hey, I've been observing things about the business. I think we have so much potential with it. I have some ideas, which you might find interesting. What if we were to change course a little bit?

Hear me out. No worries if you disagree.”

You try to take it out of the personal. You approach them more of, "Hey, I have an idea, I've something that you and I can do together." You know what I mean?


Yes. Most definitely. I find it interesting because your business is so much about people and relationships. My work with mental health shares the same focus. I am curious to ask. In the tech world, when we think about mental health right now, there are so many different definitions. What does it mean to you?

It means a lot of things to me, but what it boils down to is living the most fulfilled life and having the most positive effect on people individually and the world. Coming at everything from a position of inner peace.

To me, the two of them can be synonymous. In other words, inner peace and mental health. They go hand in hand. Achieving inner peace means reaching a very high level of mental health.


That’s such an interesting definition, especially when you mentioned inner peace. You're the first I’ve interviewed who has defined it that way.

If you're not peaceful inside of you, how could you foster an environment around you of peacefulness? There's a bunch of offshoots of that, including empathy for others, being kind to others, etc.


Oddly enough, I feel like in the tech industry, psychological safety is missing for a lot of founders. When I talk to founders, there is almost the longing for it. So much of the time, we live in a world where we feel unsettled. Like, "Hey! I did a nine-figure exit, but actually I'm still searching for meaning. For happiness. I'm still human."

There's a couple things I and other people have observed. Even in the Toronto tech ecosystem, it's kind of like high school all over again. Who's popular? What parties are going on? Am I being left out? All that's really, really unhealthy, you know?

I'm friendly with the CEO of UNICEF USA, a wonderful woman named Caryl Stern. They've got this big, big gala that happens every year called the Snowflake Ball. Anyway, it was amazing. They do great work and raise important funds for important causes. She invited me and my wife; we sat at her table. Caryl’s husband was saying to me that the two of them travel around the world to these really, really tough places in Africa, where people are living in huts, if they have any shelter at all. Or just sleeping under the stars. They're walking miles to get fresh water.

He said to me, "The thing that's been most jarring and most startling to me, is that these people are happier than I am. Or happier than most people in this room. They're dancing, they're singing, they're holding our hands, and they're laughing all day." It's just very fascinating. I'm not the first to tell you this, but happiness transcends money and material things. Don’t get me wrong, not having to worry about money can alleviate much stress, but in and of itself, you can’t buy inner peace and happiness.

That perspective is fascinating. You know?


Yeah. It is startling in a way. It can be a shock to people when they reach the end of it [their entrepreneurial journey] because they've worked hard for so many years. They reach the end and it's like, "Oh, it's not what I expected. At all.”

You find that with a lot of famous people too. It’s not uncommon to hear: "I've finally reached my level of fame. I'm number one on the Billboard Music Charts worldwide. I can't figure it out. I'm still depressed." Right?


I’m curious then. What can people in our community do to move mental health or emotional well-being forward?

I think outlets are very important. Different things work for different people. For me perhaps it’s sports, boxing, music, massage therapy, spending time with my beautiful wife and kids. It's important to have those outlets. It's important to take breaks. Massage therapy works for me.

Whatever it is, find that thing that works for you. It can't all be work for a long period of time. For an extended period of time, it can't all be work.


Last question. There's definitely founders, investors, people in the startup ecosystem who are reading this interview. What is a parting lesson or thought for them to sit with? Especially as we engage in mental health.

It's not easy being original and you need to be prepared to be judged, often out of context. Especially when you inevitably stumble. You will be given advice out of context, when you dare to be different. That's just the way it is. But you need to tune out the negative and preserve your energy. When you are focused on preserving energy, beware, you might be mischaracterized as low energy! But in my case, be also grateful for the loving friends and family who are supportive of me.

I do my best not to judge others or speak ill of anyone. I like to think that has rubbed off on those closest to me, especially my amazing kids. My wife is incredibly wise, and I feel we learn from each other about compassion, empathy, and truly listening.

It's important for us to be supportive of one another in the founder community, and even beyond. You may know the name Adam Grant. He's a psychologist?


This is Originals?

Yeah. I was fortunate enough to meet him not too long ago. I admire a lot of the work he does. I forget exactly what he said, but it went something like, "Here's some unsolicited advice. Don't give people who are struggling, unsolicited advice. It's more important to let them know that you're present and you're there for them."

I think that's a really, really profound statement. That we should be each other's keepers and as I said earlier, not judge one another, make false assumptions, and criticize. It's important to just be there for one another.


Thank you so much. For not just your time, but for sharing your perspective.

You're most welcome. It’s been fun!

Cherry Rose Tanwave1