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Kate Isler of TheWMarketplace: “Women are just over half of the population”

Women are just over half of the population. I talk with women everyday and they tell me why they can’t have the career, job, family or life that they dream of. I never thought I could either, and I share my story with all of the ups, downs, and real events so that they can […]

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Women are just over half of the population. I talk with women everyday and they tell me why they can’t have the career, job, family or life that they dream of. I never thought I could either, and I share my story with all of the ups, downs, and real events so that they can see what is possible. I came from a place where I didn’t have a fancy education, money or high-level connections. What I did have was children, a husband, and a desire to succeed. I want to inspire women to not self-select out of following their passions or dreams.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Kate Isler.

Kate Isler is the Co-Founder of TheWMarketplace, an economic engine for women and eCommerce platform that supports women-owned businesses, services providers and gender balanced companies. With over 20 years of international executive leadership experience gained working for Fortune 100 companies, Kate’s journey of leadership, challenging the status quo, overcoming adversity, and breaking gender stereotypes motivates and inspires. Her experience in high tech as a CEO of a digital health startup and as an executive at Microsoft, where she spent many years living and working overseas, provides a powerful platform of real-world expertise and examples to draw from when addressing gender equity and balanced management practices. She shares her incredible story and insights in her forthcoming memoir, Breaking Borders (HarperCollins Leadership), available on March 2, 2021.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I started out in technology and spent what feels like 200 years in the software industry, working for Microsoft. Most of my career was spent working and living outside of the US. I lived in the Middle East and Eastern Europe and worked in Africa, Central Asia, China and Latin America. I returned to Seattle, still with Microsoft, and led the Windows International Marketing team. After I left Microsoft, I led a digital healthcare startup. It was hard and lonely to move from a corporate setting with large teams to a start-up where I was the only executive!

A friend who had moved from Europe was experiencing her own struggles to get her family settled into Seattle and one evening over a glass of wine she suggested that we find an International Women’s Day event to attend to cheer us both up. We couldn’t find an event in Seattle, so we hosted one! We promoted the event on our social channels and at that first event had 85 people celebrating International Women’s Day in the basement of a We Work building. Over the next 4 years, our audience grew to over 500 attendees and I quickly found that working to accelerate gender parity was much more fun than digital healthcare. And as I was out of money for the startup, we closed that business down. Then COVID-19 happened and the world shut down just a few days after our International Women’s Day event in 2020.

As the weeks and months went on, and more stories came out about the disproportional effects the pandemic was having on women, I felt I had to do something. I kept thinking that there must be a way to put money into women’s bank accounts.

I started thinking that if I could connect my technology experience with the upward trends in online shopping, and direct this trend toward women-owned businesses, it could make a real difference. A few days later as I was talking with a friend about the idea, she revealed that she, too, was among those women being affected and was facing the prospect of being laid off from her job. As another woman who is passionate about gender parity, she joined me to start this business.

We opened TheWMarketplace for consumer shopping just over 3 months later with over 300 products for sale.

Today, we are 5 months in, and have over 300 women-owned businesses and professional services offering over 2,000 products and have had 60k visitors to the site.

We have built a values-driven online platform and ecosystem that focuses on building a business and community. We are the Economic Engine for Women. We have removed many of the barriers that discourage women from starting or growing businesses by providing a way to grow their existing online business or pivot from brick-and-mortar to online. And we have given them a community to connect with, learn from and from which to purchase products or services. It’s an ecosystem that reflects how women raise each other up and support each other. Our goal really is to change the world.

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

It has been unprecedented in my experience to gain the momentum and enthusiasm that we’ve received for TheWMarketplace and our mission. This is not my first startup, and I have to keep telling my team and co-founder that what we are experiencing is not normal. We simply started talking about the platform and our mission and people joined us. We opened a round of funding and closed it within 3 days. We have built a team of passionate women who are aligned with the vision and jumped on board before we could pay them.

Once we tell people that our mission is to be the Economic Engine for Women, they jump in with both feet. Women are facing such an uphill battle for equity, especially during these extraordinary times, and I am heartened every day by the support we are receiving from both women and men.

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?

I have two answers here. First, the biggest mistake we made was not listening attentively enough. We had identified businesses and women who we thought would be early adopters and supporters of TheWMarketplace. We contacted each one and gave our pitch. All of them nodded along, and were very supportive. One in particular asked about sponsor packages and how to really get involved in supporting us as we launched. We were so excited and certain that she was going to buy a sponsorship package and be a featured brand. After the third call, when we were high-fiving each other for how awesome our pitch was, we received an email from her explaining that she was supportive of our mission but through all of our conversations we had not asked one question about her business goals. In our excitement to tell her about our business, we forgot to ask about hers and that led her to decline the sponsorship. What a wake-up call! We reflect on this experience regularly and have embedded active and reflective listening into every aspect of our business. We listen to our customers, our sellers and our team so that we are aligning and adjusting our goals with what is important to each of these groups. Without all of these constituent groups, we would not have seen the growth that we have.

My funny story is about our company’s observance of “Catherine Miller Day.” Catherine Miller was the first person to make a purchase on TheWMarketplace who no one on the team knew. All previous purchases had been made by someone in our network, so having an unknown customer trust the site and our business enough to make a purchase was a very big deal to us. That was our first big celebration as a team and we have vowed to celebrate “Catherine Miller” day every year.

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?

There are a number of people that have been very influential in my career. Some of them in a supportive and positive way and some have been examples of what I never wanted to be as a leader.

One, in particular, was a woman I worked for early in my career. I worked at an ad agency and one of the partners was a woman who was a brilliant marketing and communication strategist. I watched her assess marketing problems and come up with just the right approach and write amazing campaign messaging that almost always hit the mark and drove successful results. But she had terrible interpersonal skills and was difficult to work with. The team would be on pins and needles each day until she arrived and we had the chance to see what kind of mood she was in. A bad mood would set the tone and tension level in the office for the whole day.

I learned so much from her about marketing and about how NOT to be a leader. I sometimes think of her when situations come up and I have to consider how my attitude or response will affect the larger team.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

What’s even more alarming to me is that those female-founded companies are only receiving 2 percent of venture capital investment. That number dropped from a high of 2.8 percent in 2019 back to 2 percent in 2020.

There are 12 million women-owned businesses in the US. Women start 60% of the new businesses in the US, (40% of those are by women of color) and earn revenue twice as fast as businesses started by men. Funding is what fuels business growth and success. Without investment, many businesses fail.

Simply put, many women become discouraged by the lack of funding for their businesses, especially when they see men-founded startups disproportionately receiving funding.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

The best thing that can be done to support women’s businesses is to fund them!

  1. Governments need to modernize their support: The Small Business Administration offers templates and coaching on traditional business practices, but very little on eCommerce. There are also too few funding and grant programs to support women in starting businesses that have an online presence, which is so crucial for success in today’s economy.
  2. Banking: There is a saying among female founders that many women-owned businesses die in bank parking lots. Banks need to be deliberate about investing in female-owned businesses. I can tell you firsthand how difficult it is for women-owned businesses to secure any type of credit from banks. Even credit cards are a challenge. I have experienced it with banks of which I have been a personal customer for many years.
  3. Investing: There seems to be an investment climate in which every business must be a billion-dollar unicorn within the first few years or it is not worth investing in. I believe that we need to take a more measured view when investing and look toward the long-term, stable growth that women-owned businesses often excel at. What if the goal for investment returned that are steady and generated over time, created jobs and supported families and employment? It seems to me that this would be a better model for investment and growth that would support entire communities, rather than a few unicorns at the top of the investment pyramid.
  4. The pandemic and economic downturn have driven over 2 million women out of the workforce in the past 11 months. The response has been for major companies and brands to fund virtual job fairs that offer resumé writing and interview coaching. This approach ignores the fact that many of these jobs have gone away and women have left the workforce because they are responsible for childcare and homeschooling. A great resumé won’t bring a job back or solve the childcare problem. The job fair and resumé and interview coaching solutions all feel like attempts to “fix” women: if your resumé were just a little better, or if you were more appealing in an interview, you would get a job. But women aren’t the problem and they don’t need to be “fixed.” The structure of our society and the imbalance in access to capital is the problem. If women were paid the same as men, had accumulated wealth at the same rates, had the same job access and security, we would see men and women returning home to provide child care at the same rates. But that is not happening.

I believe the way forward is to meet women where they are. Invest in their businesses which would enable them to determine their own working conditions and support job creation in their own communities. And let’s listen to the data that has indicated over and over that women-owned businesses are sound investments.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

I don’t want to minimize that being a founder is scary and hard work. But the reward of working in a business that you are passionate about is magic. You can choose who you work with, and how you work, and determine the culture of your workplace and your team.

As a founder or co-founder, you have the ability to create the job you have always wanted, without established norms and workplace cultures.

What are the “myths” that you would like to dispel about being a founder. Can you explain what you mean?

I think one of the biggest myths is that founders know everything about a business. The best founders I know ask the most questions and build teams of people that have skills in areas that they don’t.

I went into my first startup thinking, “This is a small business, how hard can this be?” I found out just how hard it can be when I had the wrong team and ran out of money. I was afraid that if I asked too many questions people would think I really didn’t have a clue how to run a business. In some ways that was true, but if I had been honest with myself, I would have hired different people and made different decisions.

One of the major reasons that TheWMarketplace is successful is that I know what I don’t know and have built a team of experts around me to help with finance, digital marketing, operations, etc.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

I honestly have just started thinking of myself as an entrepreneur and founder. I had a corporate job for years and I thought that was who I was and who I always would be. Being a founder is about passion and drive. Anyone can do it if they have those two qualities and have an idea that they simply cannot stop thinking about. But I think it’s also crucial to build a team around you who can provide the expertise that you don’t have.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

I wish someone had told me or I wished I had listened? 🙂

First, be passionate about the business you are going into. Understanding a market isn’t good enough. When you are starting from scratch, your passion will come through and attract the people you need around you to be successful.

My first startup was a digital healthcare product. It was a great product, and there was a need for it in the market. BUT… I saw it as a business opportunity. I didn’t have a lot of the first-hand experience with the need for the product so I never came across as authentic and ultimately I wasn’t a good testimonial for the product. People told me there would be a steep learning curve, but I didn’t really believe them. I thought if I learned the market and had the data that would be enough. It wasn’t!

Second, ask questions, even if you think they are dumb. Starting and running a business is complex. Laws, regulations, attitudes, and market conditions change all of the time. You can’t possibly know everything all of the time. Establish a community of expertise that you can tap into.

When I was raising money this past winter, our investor wanted to change the term sheet in a way that would significantly drive down the valuation of the company. I had raised money before but didn’t know how to manage this situation. So, I brought in an expert and asked our attorney for suggestions. She came up with an amazing, creative solution that would keep the cap table intact AND give the investor what they wanted. I had no idea that this solution was even possible. Asking the simple question made a huge difference in the moment and long term for the company.

Third, create the company you want to work for. When you are building your team and looking to hire, just because someone is available and has a skill that you need, doesn’t mean they are right for YOUR company. Pause and determine whether or not the person meets your cultural goals. Skills can be learned, but attitude and cultural fit can make or break a business.

In a previous company, I hired an engineer who had great recommendations for his technical skills but who wasn’t committed to the business the same way as the rest of the team. This lack of commitment was a distraction for the business and it cost money to pivot and replace him. In the end, it was bad for morale and expensive, even though he had looked really good on paper.

Fourth, a co-founder is critical. Having someone who has your back, shares your passion and is your partner makes all of the difference.

Susan and I are a professional married couple in every sense. We are one another’s sounding boards, support each other’s decisions, and have locked arms on our journey to make TheWMarketplace successful. Being a founder is a two-person job! Despite working remotely, we talk almost every morning to set daily and longer-term goals, clarify priorities and check in on each other. We also bring different skill sets to the table and know that we can rely implicitly on the other to handle parts of the business where we have less experience or depth of knowledge. It is profoundly important to not carry the entire burden of a start-up on one set of shoulders. Plus, it is so much more fun to celebrate successes with a partner!

Finally, LISTEN. To your customers, to your community, your partners, the market, and ALL your stakeholders. Listening and understanding what your customers and stakeholders are saying is the difference between success and failure. Founders start a company because they see an opportunity or problem in the market that needs to be addressed. But realizing that there may be multiple ways to address it is key.

We thought eCommerce was going to be our first big revenue source. But it isn’t! Listening to the market, we have a great solution and a competitive advantage, but the biggest contribution to our revenue at this time is through partnerships and advertising. Our investment in consumer marketing is high but as we build brand awareness the return is low. We know this will shift with time, but when we started, our timeline was very different!

How have you used your success to make the world a better place?

The mission of TheWMarketplace is to be the Economic Engine for Women. I am determined to accelerate gender equity and change culture. The World Economic Forum Report on the Gender Gap in 2020 estimated that it will be 257 years before women reach economic parity. That is several hundred years too long!!

My goal is for TheWMarketplace to remove barriers for women to achieve success online and provide a values-driven online platform and ecosystem where women-owned and gender-balanced businesses can sell their goods and services and learn from one another. We have also discovered that women entrepreneurs crave a supportive community where they don’t feel so alone in pursuing their business goals. TheWMarketplace provides exactly this community with our monthly community calls, ongoing communication through newsletters, and showcasing the sellers on our site with our “Her Story” spotlights. All of these pieces contribute to a feeling of belonging and support that is so crucial in our “remote” worlds. I want to change the world!

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Women are just over half of the population. I talk with women everyday and they tell me why they can’t have the career, job, family or life that they dream of. I never thought I could either, and I share my story with all of the ups, downs, and real events so that they can see what is possible. I came from a place where I didn’t have a fancy education, money or high-level connections. What I did have was children, a husband, and a desire to succeed. I want to inspire women to not self-select out of following their passions or dreams.

I also have in my life what I call my “Council.” This is a group of women who I know always have my back and to whom I can turn to for advice, support, or the occasional course correction. I would encourage every woman to be very intentional about creating something similar. I can’t live without my council. Ask me and I will join yours!

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment 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.

Jennifer Klein and Julissa Reynoso, the co-chairs of the Biden Gender Policy Council: I believe that in order to narrow the gender gap there will need to be broad-scale cultural and policy changes. Access to healthcare, equal pay, political representation and solutions to childcare are systemic issues for women in the US and globally. There are no quick solutions. The issues that women are facing must be acknowledged before they can be addressed. I think the national policy is a good place to start.

Sallie Krawcheck and Melinda Gates are fierce women’s right advocates. Each of their voices carries weight. I would like to meet them and ask them to amplify the voices of average women.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

Thank you for this interview! I can talk all day about my passion for gender parity and my excitement around providing a new platform for women-owned businesses to grow and find community. It’s a pleasure to share this with your readers.

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