Inspirational Women Leaders Of Tech: Laurel Anne Stark of On The Five Things You Need To Know In Order To Create A Very Successful Tech Company

Doug C. Brown
Sep 27, 2020 · 16 min read
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Don’t compare your insides to other people’s outsides. More women than you know are managing trauma, abuse, reproductive challenges and other deeply difficult personal challenges in addition to running their businesses. We are not the “weaker” sex. We are astounding examples of the power of the human spirit to overcome even the most crushing obstacles.

As a part of my series about “Lessons From Inspirational Women Leaders in Tech”, I had the pleasure of interviewing Laurel Anne Stark, founder and CEO of (, the first-ever web app designed to support female entrepreneurs in business and life.

Laurel is an acclaimed business and marketing consultant and mental health advocate, dedicated to empowering self-employed women to do well.

Laurel is also a three-time nominee of the Canadian Women Entrepreneur Of The Year Awards presented by Women of Influence and Royal Bank of Canada, the founder of The New Media Group, a digital communications agency and lead author of The State of Female Entrepreneur Mental Health, the first ever research report of its kind. Laurel has been supporting female entrepreneurs since 2003.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

When I read “Are Entrepreneurs Touched With Fire?,” the 2015 research report that came out of Berkeley University, my own experience suddenly made complete sense. The report concluded that entrepreneurs are directly affected by mental illness at a rate just under three times the global average.

Self-employed since 2003 as a business and marketing consultant, I’ve had my own battles with mental illness that included a severe bout of alcoholism and burnout and bankruptcy, which is so common among entrepreneurs.

When the Berkeley study came out, I was running a digital marketing agency and, as a wife and stepmother of three, I was struggling valiantly to do it all and be it all. Frequent panic attacks and persistent and disruptive negative thoughts were regular accompaniments to my imposter syndrome — and I wasn’t alone in this experience. The entrepreneurs I mentored at the Women’s Enterprise Centre and many of my female clients reported similar experiences. Managing anxiety, depression, overwhelm, substance misuse and the aftermath of the trauma that comes with harassment and worse, seemed a job unto itself. These obstacles were significantly impeding our performance and business growth as self-employed women.

Out of curiosity, I began a search for mental health support specifically for entrepreneurs. I found nothing. I gave my assistant a budget of 20 hours to continue the search, and she found the same — there weren’t any mental health resources tailored to support entrepreneurs. I was aghast. This seemed incredibly shortsighted. After all, entrepreneurs are responsible for significant contributions to the economy, job creation and innovative solutions to every-day problems. Why weren’t there specific resources to adequately support the mental health and wellbeing of a population so valuable and vulnerable?

Meanwhile, my research led me to find statistics that still shock me. Domestic violence rates are on the rise, the gender wage gap still exists and women hold a mere 29% of leadership positions worldwide. I had naively thought that gender parity had been achieved.

What I learned through my research is that women who are self-employed are not only at three times greater risk of being affected by mental illness — as per the Berkeley study — but also must face, manage and overcome a staggering array of gender-based obstacles. Less access to wealth and less safety in the workplace and everyday life are just a few of the serious barriers women were grappling with. I asked myself, what if we looked at these separate studies cumulatively? How many women are managing more than one of these obstacles, along with the stressors of being self-employed? Based on my own experience and the patterns I observed in the thousands of female entrepreneurs I’d mentored over the years, I realized that if a self-employed woman was experiencing even a few of the obstacles noted in my research, she’d be suffering a deep, lonely, mental health crisis.

That’s what led me to initiate research into female entrepreneur mental health and create to provide a solution to this vulnerable community.

Can you share the most interesting story that happened to you since you began at your company?

When was just a few months old, I applied to Pitch at the Beach, an event that connects investors and start-up founders in Tulum. There were over 270 applicants and only 24 were accepted to pitch. Incredibly, was one of them. Fast forward and there I was, standing barefoot in the sand on my birthday, pitching my business to a crowd of LATAM Venture Capitalists, Angel Investors and world-renowned business people — including Zev Siegl, the man who co-founded what has become the Starbucks we know today. It was like a dream. I still can’t believe it happened. I met some incredible people, received honest advice and made valuable connections — all without shoes on, which is very much not how these events are typically run.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was 23 years old and first starting my career, I was offered a partnership at the agency I was working at as a commission-only sales person. I was very inexperienced. I didn’t get a lawyer to review the agreement and I certainly didn’t do my due diligence. I didn’t even know what due diligence was. As a result of signing, I became a partner and acquired, jointly and severally, $80,000 worth of debt. I didn’t find out until four years later. It was an expensive and painful lesson, but it’s taught me that accountants and lawyers aren’t as expensive as they seem!

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Being self-employed through the world economic crisis in 2008 was extremely difficult. I was working in the tech sector at the time as the founder of a digital solutions agency, and the bottom had fallen out of the industry I had built my career on. Checks weren’t coming in, the bills were due, and I was vibrating with anxiety. I did actually try to get a job as a waitress, but they didn’t hire me. I had no choice but to keep going. At the time, I was drinking as a way to cope with stress, and my stress was an all-time high. I was having physical and mental health issues.

Looking back, I was the poster-child for entrepreneurship. I bought into the work-hard, play-hard culture and I had no notion of taking care of myself as being integral to my ability to navigate the recession. It was around that time I burnt-out and hit my bottom with alcoholism. If only I’d had some holistic support from a community of older, wiser women at that time, I might not have struggled so much. Now, everyone talks about how hard those years were, but at the time, I thought I was the only one fighting to survive.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My mentor Brenda Mahoney, the founder of the first Paint and Sip business in Alberta, Canada, among other businesses, helped me with all the things I didn’t know I needed help with. She has consistently shown me that it’s possible to do business with a big heart, taught me how to filter out multiple competing priorities, and also sent me new business and introduced me to key people. She’s led by example and shown me what vulnerable leadership looks like, and has always believed in me. Brenda has been honest about her struggles and it’s given me permission to look at my own. Without her mentorship, I certainly would not be where I am today. In fact, her help demonstrated the value of receiving support from a peer and the value of building authentic community with other self-employed women. That’s why part of my mission with is to connect female entrepreneurs so we can support and learn from each other through the common challenges we face as self-employed women.

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Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

What do you need to do here before you die? In Latin, it’s known as Momento Mori, which means “remember you will die.” Whenever I need a perspective shift, I imagine myself on my deathbed looking back over my life. I then ask myself, what would my future self think about where I am today? I try to make decisions that will minimize the amount of regret I will have. People on their deathbed consistently report regretting not following their dreams, caring too much about what other people think, wishing they had more courage and working too much. I make sure to consistently check in with this future self to keep me on track and fueled by purpose.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. We’d love to learn a bit about your company. What is the pain point that your company is helping to address?

As the first-ever web app designed to support female entrepreneurs in business and in life, helps self-employed women overcome three of the four main obstacles to success. We recently released the first-ever report on the state of female entrepreneur mental health, and our research shows that in addition to the day-to-day struggles of entrepreneurship, self-employed women face significant additional barriers to both their success and their well-being. They are extraordinarily vulnerable to experiencing challenges to their mental health and that impacts their ability to perform. Thanks to our research findings and my lived experience, understands that, for self employed women, business and personal aren’t separate; work is deeply personal and it’s easier to do well when you feel well.

What do you think makes your company stand out? Can you share a story?

Our company stands out because we are developing the only technology that exists to support self-employed women with both their mental and emotional health and their business success. We have already made history by publishing the very first report on female entrepreneur mental health, and hope to spur further research into this topic as well as open a dialogue around why female entrepreneur mental health matters. A report from Mckinsey Global Institute predicts that if female founders scaled their firms at the same rates as male-owned businesses, we’d contribute $12 trillion to the global economy.

Are you working on any exciting new projects now? How do you think that will help people?

We are working hard to bring to life by the end of 2020. Due to the gender based barriers to receiving venture capital investment — last year, female founders received less than 5% of VC investment — we’ve decided to crowdfund as research shows women do better with crowdfunding. Currently the project is self-funded, but in order to make our desired impact, we are going to need a little help. To receive updates on the launch, readers can sign up here.

Let’s zoom out a bit and talk in more broad terms. Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?

Certainly not. We’re under-represented generally and in leadership positions, the bro-culture, especially in gaming, drives women out of the industry, and women-led companies are underfunded despite out-performing their male counterparts. I have six specific recommendations:

  1. Conduct empirical studies on the needs and experiences of female entrepreneurs to give them a voice and create more interest from governments to support their unique needs and potential contributions to society and the economy.

In your opinion, what are the biggest challenges faced by women in Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

Regardless of the limitations of our research and the body of studies presented in our state of female entrepreneur mental health report, we believe there is sufficient evidence to suggest that the impacts to robust mental health in self-employed women are significant and more numerous than those experienced by the average population. The sheer number of factors, their statistical prevalence and their documented impacts on mental health are far greater than we ever imagined when we began this project.

Not only is this group more at risk of confounding mental health challenges, but there are also engrained barriers that isolate women in these experiences and prevent them from talking about and addressing their needs. These barriers include the culture of bravado in entrepreneurship, stigma about mental health, concerns about mental health conversations impacting business reputation, prevalence of internalized victim-blaming and reluctance to provide fuel to the narrative of being “lesser male.”

Arguably, the prevalence of a handful of the following risk factors would present above-average levels of stress on mental and emotional wellbeing in the lives of women.

In the workplace risk factors include gender-bias, harassment, violence and the requirement to be professionally pretty. Domestically, risk factors include the burden of care and the high rates of domestic violence. Personally, hormonal and reproductive factors play an incredible part in wellbeing. For example, wny failed pregnancy,which is so common between 25–50%, skyrockets a woman’s risk for experiencing poor mental health.

What would you advise to another tech leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

I’d offer two pieces of advice. First, go back to the original reason you started your role and the original problem you set out to solve, and see if you can improve how you’re solving it. Put simply, revisit your “Why”. Second, I’ve found that a survey of your client base can often provide motivating feedback — both positive and negative — which is helpful to increase motivation. If you’re always thinking about how you can best serve your customers and constantly innovating, you decrease your odds of stagnating.

Do you have any advice about how companies can create very high performing sales teams?

Educate your sales people on the problem you solve and ensure the folks you have on board are passionate about solving the problem, compensate them super well — both monetarily and with acknowledgment and perks — and show them how they’re progressing towards their goals against their peers.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

Always test your assumptions. When you verify with your customers before making decisions, you gather data to support your hunch. In short, you want to assume, test, iterate, validate, and repeat. Listen to what your customers are saying and find innovative ways to solve their problems. Look for patterns among the client base and use these trends to better understand your ideal customers and grow this community.

At, we tested eight different messages and designs and iterated each of them three times before we launched our crowdfunding campaign. It was incredibly interesting to see how our community responded to different messaging. It proved to us that we can’t read the customer’s mind and that we always need to be verifying with them what we think they need.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

Every user interaction should be strategic, whether it’s the sales funnel or the customer journey, each step should be well thought out, tested, iterated and validated before it goes into the workflow or User Interface. Always ask for feedback and ask for it in three or four different ways. People are busy and inundated with information, so you have to be persistent. And it’s worth it if you don’t want to end up building an incredibly expensive technology that no one wants. Additionally, stay on top of the evolution of technology. You lose so many people by failing to adapt to a new browser or device or technology. You want to bring the new technology to your customers, not the other way around.

As you likely know, this HBR article demonstrates that studies have shown that retaining customers can be far more lucrative than finding new ones. Do you use any specific initiatives to limit customer attrition or customer churn? Can you share some of your advice from your experience about how to limit customer churn?

I have three pieces of advice from my experience on how to limit customer churn. Take advantage of automation to ensure they’re hearing from you at regular intervals, remember small details about them and find clever ways to surprise and delight them. I’ve found this to be hugely impactful in customer retention.

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

1. You can do anything, but not everything. Pick the things you would regret not doing on your deathbed and make sure you at least try to make them happen. The only failure is not trying. Your reason needs to be bigger than money, as you’ll need that passion to get you out of bed in the morning. I started a software outsourcing company that ultimately failed because my passion for the problem I was solving wasn’t big enough to motivate me to do what it took to make sure it was successful.

2. You need community. Accept help, ask for introductions and have three people you can tell the truth to about how you’re doing. Both from a support and networking perspective, leaders are only as strong as their team. When we were building the beta design concepts for, the ideas they had were so much better than the ones I had. My vision had become myiopic as I’d been working at the problem from my own perspective for so long. Our success is 100% because of the strength of our team.

3. Go offline regularly. Completely offline. It will do wonders for your mental health and you’ll find you’re a better performer when you come back online. When I first started my business, I didn’t take time off for six years. I really wouldn’t recommend that.

4. Systemic bias is real. Women have to work doubly as hard for less than half the compensation and recognition. It’s not your fault and you’re not alone. This is how it is right now and why we need your talents to make changes. Learn to identify when this reality is impacting your performance and get support for it, ideally before it becomes a real issue.

5. Don’t compare your insides to other people’s outsides. More women than you know are managing trauma, abuse, reproductive challenges and other deeply difficult personal challenges in addition to running their businesses. We are not the “weaker” sex. We are astounding examples of the power of the human spirit to overcome even the most crushing obstacles.

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I think we’ve got the bones of a movement happening with We are all about empowering and supporting female entrepreneurs in the ways that matter to them so they can do well in life and business. We’ve identified the barriers to their success and we’re working on ways to help female entrepreneurs overcome them. I feel like this could bring enormous benefit to the most amount of people because women reinvest in their communities, they have more engaged teams and tend to operate holistically. I’d like to think that if more self-employed women were doing well, we would have a reduction in many of the social and environmental issues we’re facing as people around the globe right now.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them :-)

I would love to chat with Lady Gaga. As a fellow mental health advocate and pink hair aficionado, I think we would have a lot to talk about. Ultimately, I think she’s an enormously talented and resilient human being and I am so glad she’s using her influence to reduce the stigma of mental health. The reality is, self employed women are at an increased risk for mental health concerns. Right now, that’s 250 million women and in ten years, it will be over 400 million. That’s a lot of women we need to support!

Thank you so much for this. This was very inspirational, and we wish you only continued success!

Authority Magazine

Leadership Lessons from Authorities in Business, Film…

Doug C. Brown

Written by

Sales Revenue Growth Expert | CEO and Business Consultant at Business Success Factors | Author

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Doug C. Brown

Written by

Sales Revenue Growth Expert | CEO and Business Consultant at Business Success Factors | Author

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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