The
View from Initialized

Meet the Partners Breaking Venture’s Glass Ceiling

(Left to Right: Jen Wolf, Alda Leu Dennis, and Kim-Mai Cutler)

While less than 5% of U.S.-based VC partners are women, our current senior investment team is 50% women. We’re proud of this, and want to support a vision of inclusive entrepreneurship. In honor of Women’s History Month, we sat down with the women breaking venture’s glass ceiling — Alda Leu Dennis, General Partner; Jen Wolf, COO & Partner; and Kim-Mai Cutler, Partner. 

How has the VC landscape changed since you started investing?

Alda: There is a lot more money, a lot more opportunity, and a lot more investors today. There’s a lot more capital in the market and more investors are willing to take risks. Investors who missed the last decade’s booming market are realizing that they have underperformed. Now, it is also easier than ever to be an investor; all you need is a checkbook and some money. Not to mention, it’s easier than ever to build reputations and followings from anywhere on insular networks and social networks like Twitter and LinkedIn. Relatedly, these communications tools are ubiquitous and access to information is democratizing. 

Jen: As capital in the market has expanded over the past five years, it has required VCs to be even more crisp on what they offer founders. Founders are not just looking for money from anyone — they want to work with someone they like and trust, someone who can offer help in a variety of areas. Initialized’s team-based approach has been an advantage here. Partners can be specialists, and together we form the world’s best generalist. 

Kim: I only shifted into investing five years ago from working in journalism, so it’s actually a relatively short period of time to be an investor. But even in that short period, I’ve seen the landscape change. For example, in the last five years, SaaS has established itself as a bonafide, much more predictable category in public markets, whereas consumers led the first half of the 2010s before fading then ultimately coming back strong in 2020. Crypto has waxed and waned with peaks in the ICO wave of 2017 and again now, with Bitcoin’s recent surge and the re-emergence of NFTs. The whole category of venture is so much larger than it has ever historically been.

Why did you become an investor?

Alda: I became an investor because I like working with early-stage companies and helping them grow. I also enjoy thinking about how to make the world better and being able to invest in the ideas that will help do that.

Jen: I started in consulting and enjoyed learning about a variety of industries, businesses and approaches. As I progressed in my career, I focused on helping my teams identify who they are designing and building for and how to use product and design to solve problems. Investing was a natural extension of this — I’m able to scale my experience working with hundreds of companies, founders and products to help additional founders avoid common pitfalls.

Kim: I had covered tech for years as a reporter for TechCrunch and wanted to do more on the operating side. Being an investor helps me do that. 

According to data, only 4.9% of U.S.-based VC partners are women. How does having three women partners give Initialized an edge?

Alda: Great investors take calculated risks and see things differently than others. I don’t know how you would do that without diversity of thought and perspective. Each partner at Initialized brings something different to the table.

Jen: Each of us has a very different background: Kim was a journalist; Alda was a lawyer and has worked in VC for some time; and I have a product and design background. We bring these different lenses to seek out and evaluate investments where women are a big portion of the consumers, buyers or participants (e.g., A-Frame Brands, AptDeco, The Mom Project) and have this in the forefront of our minds. I have also had several women founders specifically looking to work with a woman. Women founders notice when they go through a pitch process and never speak with a woman on the investing team. At Initialized, we also help our portfolio founders focus on diversity and inclusion in their companies early on. Diversity is often important to founders, and they feel more comfortable asking a woman they know and trust about how best to do this authentically and systematically.

Kim: Women are 50% of the global talent pool, and they make some of the most important household purchasing decisions from a consumer perspective. You could be overlooking 50% of the population and 50% of talent out there if your team isn’t representative. 

What are some helpful personal or professional tips shared with you along the way that have stuck with you on your VC journey?

Alda: Working with so many different types of founders and colleagues through the years, I’ve learned to listen first and if you disagree with someone, to think about the best way to communicate ideas to that person so that they will be heard.

Jen: First, ask yourself, “What are the highest leverage things you can be working on?” When thinking about these things, don’t just work on deadline or urgency. Secondly, be as direct as possible with communication and expectations — don’t let problems fester or hope that they will go away. The key qualities of an effective COO are: good judgment; a sense of fairness; and a focus on doing what is right for the company above all else.

Kim: Be curious. Learn in public. Be willing to learn from mistakes. 

How are you empowering female founders and investors?

Alda: I actively talk to many female investors on a regular basis to share deal flow and advice. From an investment perspective, I have invested in several female founders and try to provide as much help as I can to make their companies a success. I have also invested in businesses that serve or solve problems for women and mothers.

Jen: Fifty percent of the companies I own have a female founder. This has happened organically, but I always have a strong belief in the founders’ own intuition. Working with founders is often a combination of being a person who believes they can achieve their vision and also giving direct feedback and advice to help them get there. 

Kim: We should eventually normalize that it isn’t special or unusual to have female founders or investors. We should also normalize entrepreneurship at different phases of life — whether you’re just starting out close to the end of school or whether you’re raising a family. Having more women as leaders will improve quality of work and life for everyone. 

What’s one hard truth about being a VC who happens to be a woman? What’s one of the best things?

Alda: When there aren’t enough female VCs, a female-focused company, especially at later stages, can have a hard time finding champions when 95% of VCs are men who can’t relate.

Jen: Hard truth: senior investing roles often take previous investing track record (i.e., returns) into account, and because women haven’t had as many opportunities in VC, this approach either limits women’s access or forces women to change the conversation so a variety of skills and strengths can be considered. But I personally don’t feel as constrained by how “others” have done. One of the best things about being a VC is applying my active listening skills. It’s natural to use these skills and empathy when working with other people.

Kim: I agree with Alda. We need more women at funds with larger assets under management (AUMs) to champion companies and products that may not otherwise get a fair shake or hearing.

Advice for other women looking to build their career as a venture capitalist? 

Alda: Take advantage of this moment we are having where VCs are eager to bring in female investors. Take a job at a top firm; learn; do some deals; and if they don’t promote you, leave and start your own firm.

Jen: Be someone who can get things done and who people want to work with. If you can apply this to a variety of operating activities (e.g., product, engineering, sales, marketing, recruiting, culture, etc.), this is a great foundation for being someone who founders want to work with and take money from. 

Kim: Develop a deep understanding of a very large, either poorly addressed or rapidly changing market, its ecosystem of companies and entrepreneurs and become known for your expertise in it. Angel invest in founders and companies you believe in to develop a track record.

How did being a lawyer prepare you for the VC world?

Alda: As a lawyer, I think very rationally and logically and have excellent reading comprehension skills. Those things have served me well in every walk of life.

What turned out to be true (and wrong) after you made the switch from journalist to investor?

Kim: Being curious and asking lots of questions translated really well, but companies that make great investments sometimes don’t make for compelling stories and vice versa.

You’re known as being the startup whisperer and helping them deal with internal growing pains (e.g., co-founder conflict, etc.). How has this changed the way you view mentorship?

Jen: Over the years, I have moved from giving “solutions” for problems to focusing on giving founders or team members the tools to solve things on their own. These tools might include frameworks, questions about motivations and goals. Another tool might be talking through how to respond to tough topics. In many cases, it’s about clarifying what are the process issues; what are feelings or anxieties; and what are differences in expectation or communication style.

Interested in connecting with Alda, Jen or Kim? Find them on LinkedIn (Alda, Jen and Kim) or Twitter (@AldaLeuDennis and @kimmaicutler).