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Interview with Jacqueline Khayat, angel investor and Marina Massingham, CEO of Aifred Health

As part of its new Women Who Dare initiative, which aims to increase male-female diversity within its membership, Anges Québec is unveiling a series of interviews with inspiring female entrepreneurs and angel investors who have made their mark in a male-dominated field.

 More about the initiative.

Meet Jacqueline Khayat, angel investor and Marina Massingham, CEO of Aifred Health.


Hello ladies. Thank you for accepting our invitation!  Can you tell us a bit about your professional backgrounds?

Jacqueline:  I am a new angel investor, having been with Anges Québec for 2 years now. I was attracted to AQ because of my interest in entrepreneurship (I always had a bit of the entrepreneur in me).  I didn’t start many companies, but I was involved in many startups either as a business coach or by making small and big investments.

I currently work for Neptune Wellness, where I have participated in reshaping the company in many ways.  The company went from being a single-ingredient manufacturer in the Omega 3 space, to now being a full CPG company with different brands, doing extraction services and products in cannabis and doing hemp in the US. Throughout the years, I have played a major role in many strategic decisions involving the diversification of the company’s revenue streams. 

I always say I am an entrepreneur within a company, as I have participated in creating value and building a story for investors.   In a nutshell, that’s what I do!

Marina :  I’m English, more precisely from London.  I arrived in Canada 7 years ago.  My professional background is management consulting.  I became the youngest and only female partner at my level when I was in my 20s.   Shortly after, I did a classic transition from consulting into industry, where I worked in CPG and then moved to the pharmaceutical industry.  There, I held the position of Global Head of Talent Development for the commercial side of Novartis’s global business. 

After I arrived in Canada in 2013, I cofounded my first startup, a specialty pharma company, which had a successful exit in 2015.  For a few years, I worked for the post IPO startup that acquired us before joining Aifred Health as a professional CEO 2 years ago. Aifred specializes in mental health and is creating digital clinical decision support tools for physicians to improve treatment management and treatment selection in mental health, starting with depression.

Recently, we announced that Aifred had been chosen as one of the three finalists of the Global IBM Watson AI XPRIZE, a 4-year global competition offering a 3 million-dollar first prize.

I am driven by passion since a close family member suffers from major depression with psychosis.  He was 17 when he first became ill, 18 by the time we managed to get him treatment and it took 10 years before he became stable.  Therefore, I am very mission-focused and passionate about what we do at Aifred because I see the need to make a huge step change in the way patient with serious mental health issues are treated.  The trial and error approach taken to treatment selection today is the same as it was 20 years ago, and I believe our technology can really make a difference in patients’ lives.


Marina, what is the essential characteristic you look for in an investor?

I look for investors that share my passion, because if they share my passion, they will support Aifred’s mission.  This is not about a cheque; we are initiating a relationship. The cheque is just the first stage. 

If investors share my passion, understand my mission, that facilitates that relationship and I know that they will likely be supportive when things get difficult, as well as when things go well.


Jacqueline, what is the essential characteristic you look for in an entrepreneur?

I look for people like Marina who are very passionate about what they do and who believe in their story.  I think that is very critical because an entrepreneur needs to embody the organization’s values and mission in order to be able to deliver it to employees and customers.   I also like businesses and entrepreneurs who are innovating and are truly identifying gaps in the market in order to bring a solution to a real-life problem.

Put all these elements together, add a good leadership team and surround them with good talent, and you have what I am looking for as an investor. 


From your point of view, is there a difference in how an investor will analyze a male versus female entrepreneur?

Jacqueline : I think there is a difference.  I have read that an identical pitch given by a male versus a female does not result in the same outcome.  So then there is clearly a bias, which is not necessarily surprising, because it is an ongoing issue that has been carried for years by society in general.  Although I think there is a shift happening, which is great, I do think a woman will be viewed differently by investors in general.  A woman will be analyzed more critically, will be less believed in her ability to execute a strategy and reaching certain milestones, rather than being seen for the opportunities her business presents.

Marina :  I have heard a lot of what Jackie is talking about and I do agree that it exists.  In my experience, there has often been plenty of focus on the potential downsides and problems, and fewer questions about what the potential is.  You must recognize it, accept it, navigate it.  I don’t see that as diminishing me.


If there were more female angel investors or partners in the venture capital industry, would it change anything and if so, what would it change?

Marina :  I can talk for my own experience.  Only one of my VC partners is female and she and I made an immediate connection as people. I am sure that is an important part of the investment decision, because it is one human investing in another.  Yes, there are a lot of slides and numbers, but a connection is important.  It can sometimes be easier to make a connection with same gender individuals.  I would love to see more females like her across all VCs.

Moreover, I think there is also a different type of questions that you get asked from female investors, stemming from a different perspective and experience.  It gave me the chance to showcase some of my experiences and skills that were not explored by other investors.  I felt that she made a decision which really understood me completely as a person and the organization, and I feel that she may have a more global understanding of what we do than other investors we spoke to who were only focusing on what the potential downsides could be.  I believe she probably made a smarter investment decision because she had better knowledge of the ensemble.

Jacqueline :   For starters, if we had more female angels or partners in VC firms, maybe we would attract more female entrepreneurs.  Really, it’s the chicken or the egg question, but I certainly think that the VC world has been very tough with women.  It is a very bro-like culture that has been dominated by men and I think women feel somewhat uneasy at times because of the culture and/or ways.  I think it is changing, but yes having more female investors would make a difference in attracting and bringing more female entrepreneurs to the table.


Marina, before started to approach investors in order to raise funds, did you have any apprehensions about how you would be treated as a woman?

Marina : I am a healthtech entrepreneur.  As soon as you add “tech” to anything, I do not conform to the stereotypes of what a successful tech leader looks like. I was always conscious of the mental model people had of tech entrepreneurs, whether they were investors or not.

I would love to see more successful female tech entrepreneurs highlighted so that when I walk into a room, investors have another model that they could map me too.  That is challenge, it really is.


As for you Jacqueline, when first joining Anges Québec, did you have any apprehensions about how you would be treated as a woman?

Jacqueline : I think I assumed the membership would be predominantly more male, just out of habit.  I am so used to it that I don’t really think about it anymore.  It doesn’t stop me from doing things and daring.  Although my expectations were very realistic, I was surprised how few women there were in the room when I attended my first event.

I completely understand how it can be a little intimidating, but at the same time, I felt like my experience was interesting and I was confident.  I remember showing up alone and sitting at a table with a bunch of men that I didn’t know and they were perfectly nice and very intrigued by who I was, so at times being a woman almost becomes an opportunity for you to stand out.


What are some solutions to attracting more female entrepreneurs to the venture capital industry?

Marina :  I think having more female investors is of course beneficial, but I think having a good mix of women pitching in those sessions would help.  I think women gain confidence by seeing other women in the same position as themselves.  I have been very fortunate to have now started to build, in Montreal and outside, a network of great female startup CEOs, with who I can share common issues, exchange experiences, and grow as a CEO.

When you go see individual VCs, you go in just alone.  Anges Québec is one of the few places in the VC industry where you are part of a roster of people and you see who else is coming in.  I think having more women in that room passing through the AQ process at the same time would be really nice to see.

Jacqueline : That is a really good point.  Furthermore, I think everything starts with an intention, therefore I love the fact that Anges Québec has given itself a mandate and a goal regarding male-female diversity.  If you don’t actually have an intention, it is never going to happen.  I also love the fact that we now have a female CEO at Anges Québec, which is a great way to lead by example.

I think we all have to hold ourselves accountable to meet the objectives set forth and really try hard to be the progress that we want to see. Women Who Dare is a really great initiative.


In your opinion, how do women relate with the concept of perfection?

Jacqueline :  I think women have to let it go.  I think the problem is that a man will not hesitate twice to put his name on the list for the next promotion, whereas a woman will have all the qualifications and will still be hesitant, unsure and not be as daring.  We need to change that early, with kids and young females.

You don’t have to be 100% ready.  You have to take that leap of faith and trust your abilities. You can’t wait for things to be 100% perfect or ready, because then you will miss out. What has helped me is that I had great male mentors who recognized my talent and actually helped push me forward and challenged me. Taking risks is critical.  We are more risk averse as women, we don’t like to dare that much and tend to make investment decisions in a more traditional way.

Marina :   I think exactly the same as Jacqueline.  With age, experience, supporting mentors and colleagues you learn to judge yourself on what you are able to accomplish rather than how perfect you looked or how perfect the execution of an idea was versus your original vision.  You build your confidence through that experience. 

Also, I think young women are living in an Instagram culture, a world which encourages and demands a degree of perfection that we didn’t have to deal with ourselves growing up.  I wonder if that will make it more difficult for them to embrace imperfections, risks and ways of challenging themselves.


Quick fire questions

A woman that you admire, famous or not?

Jacqueline :  Everyone loves Kamala Harris for being the first female Vice President, whether they are Republican or Democrat. I think she is capable, articulate and has a great presence.  On the flipside, someone like Brené Brown I think is just truly awesome.  She has been known for her courage to talk about vulnerability and how women should show up in a room full of men and embrace the vulnerability they might feel.  She is a great speaker, author while also being super funny.  One of her most famous books is called Daring Greatly.

Marina :  Mine is a bit random.  There is a female mathematician from the 1800s, called Ada Lovelace.  She worked on a precursor to the computer and published the first algorithm intended to be carried out by a machine, which you can expand, in some ways, to the precursor of modern AI.  She was a remarkably intelligent woman born in a very boring age for her gender.  The fact that she was able to do what she did and break gender stereotypes of her age, use her amazing intellect to produce work that is still recognized today is beating the odds.  That is just using your smarts and creativity to just blast through barriers.


Do you have a personal motto that you live by?

Jacqueline : I have a few.  I often like to say that there is no future in the past.  There is no point in looking back and regretting.  I like to always look forward and overcome new challenges.  There is also this famous quote by Marilyn Monroe: women who seek to be equal to men lack ambition.  (Laughs)

Marina :  I look to be true to myself, to my mission and loyal and supportive to my team. I also always think about climbing the next mountain, then the one after that, and so on.

There is one phrase that I often tell my team: don’t cling to a mistake because you have invested a lot of time making it.  It is quite hard for people to let go of things that aren’t working but it is necessary.  We are in an ever-changing environment and if we are going to be innovative, we have to recognize when something isn’t working, when the resources are not yielding what you want, and then have the courage to let it go and move on to something else.