Initialized partner and COO Jen Wolf has been promoted to President, making her one of few women to hold such a position in the venture capital industry.
At Initialized, we just returned over $600 million to our limited partners so far this year. Now, we’re going to talk about how we will return billions of dollars over the coming decades.
We’re sitting down with Jen Wolf, who started as a partner with Initialized four years ago, but we first met and started working together in 1998 — that’s 23 years ago. Today, I’m proud to announce she has been promoted to President and Partner at Initialized.
Now, let’s dive into how design thinking, conscious leadership and diversity all work together to help us get to that next level.
Garry: Jen, great to hang out with you as always. I get to see you all day most days, so it’s fun to have you on the YouTube channel. Congratulations! I’m so psyched to call you both Partner and President of Initialized.
Jen: Thank you. It’s great to finally be on the internet with you since I’m known for not having much social media.
How Garry met Jen
Garry: The crazy thing is the two of us have known each other for an outrageously long time. Was it 1998 when I first met you?
Jen: Yes, when you were in high school.
Garry: It was my first coding internship. I remember getting on BART to come into San Francisco, to go to the offices of Adjacency, which was a consulting firm that created the first Apple Store, PowerBar, Land Rover and all of these other incredible brands. You were just starting your career as well, as a designer.
Jen started as a designer
Jen: Adjacency was only my second “real” job. I met the founder — Andrew Sather, who now also works with us at Initialized — through my roommate. I thought it was a company of really cool designers and builders; I wanted to join and be a part of that.
I joined Adjacency and started out doing front-end development. There, we kept running into a particular issue. Originally, we’d serve marketing websites. After a while, designers would design something, but they were hard to build because when you put the real content in, it didn’t work anymore. We quickly realized that we should have a step at the beginning, which is to do user experience design.
We needed to think through the systems of things, the navigation and the hierarchy of things first in order to give that as input to the designers and then also give that information to the engineers. That input was helpful for them when it came to thinking about how to systematize these designs when they’re coding things and how to avoid wasting time. It was very early on in the genesis of what was called at the time information architecture or information architects, which became user experience designers.
Garry: It’s so funny to think that we didn’t even really know what these roles were called. Consulting firms like Adjacency were coming up with the playbook on how to create experiences that actually worked for people.
About eight years after my internship, you ended up giving me a job after I left Palantir. I remember that was my first day-to-day interaction design job, and it was super empowering because instead of having to both design and code, I could sit there and design all day. The funniest thing about that was I had so much time and mental space in the evenings to code that I ended up creating my first startup Posterous while moonlighting for you in 2007.
Jen: I think you’d only worked there for a couple of months when you came to me to quit your job because you got into Y Combinator. We often discuss how that was maybe the genesis of Initialized in a lot of ways, or it started you on that path.
At the time, Y Combinator was very new, and I felt a lot of responsibility for you as my former intern. I didn’t want you to get into a situation that was unsafe or suspicious, so I made sure you really looked into whether this was a serious organization or not. But once that was established, I was super excited for you to go on that journey and see what was going to happen with your startup.
I always thought that was an amazing part of working with you, even at Adjacency, which is that you really liked to build things, try anything, explore new ideas… and you had a lot of excitement for what technology could do and what the future holds. I knew you’d be amazing at running a startup as well.
Garry: Well, I wouldn’t be here at all without your mentorship and support over all these years. I want to dive into your history, story and journey into design and tech. You’re from Seattle originally, right?
Jen: Yes, University of Washington Huskies.
Garry: We are really lucky because you basically have a perfect photographic memory, which turns out to be really valuable, but it sounds like that was honed in high school debate.
Jen: Yeah, I was a Washington state debate champion in high school, and that really honed my abilities to learn and memorize a lot of information very quickly. In debate, you have to look through these little boxes of evidence, printed paper that you made photocopies of because this was way before the internet was very prevalent. You really had to rely on your memory to find things quickly. It also gave me the skills to think on my feet and not be worried about having conflict with other people or conversation debate.
I’ve really taken that through my career, all the way to a lot of what I do today, which is to invest and work with companies but also help founders navigate conflict that is inevitable in any business. It’s better to have a lot of micro conflicts, which are just ways to get ideas out there and understand where differences are and collaborate to get to a good solution, so that it doesn’t blow up into a very large scale, actual conflict between co-founders or founders. These types of conflicts can end up having a really large impact on a business and can negatively impact teams and customers. You want to have a really healthy way for teams and founders to communicate. That is really a really important part of scaling a business once you’ve decided to invest in the right team.
Garry: That’s something I learned from you: there’s actually a relationship between micro conflict. On its face, you talk about conflict, and it’s like, “Oh, that’s conflict. I don’t want that.” Now, what I realize is it’s actually doing the work.
If you combine your experience and worldview as a designer, that’s an extra empathetic aspect to it. There’s conflict, and you need to be able to understand your own perspective but then also understand the perspective of someone else and then take that point-counterpoint and turn it into synthesis. Whether you’re creating a product or trying to start a company or build teams, it’s the same thing over and over again: how do you have synthesis across point-counterpoint?
As diversity becomes a focus, it’s also really powerful when you add it to a mix of design and micro conflict. Then, you can actually create something that touches a billion people, not just your own tiny, little corner of the world.
On design thinking
Jen: Most people think of design as colors and making things look nice, but design and design thinking is a larger field or set of skills that can apply to just any level of a business or a team. I learned a lot of that early on.
When you’re designing something, you have to not just design it for yourself. You can if you just happen to have that perfect alignment where you’re the user and the designer, but most of the time, you’re not the end user. To create a really good design, you have to spend a lot time trying to think about things from other people’s perspectives — what problems might they have; why would they run into these situations; what they might be thinking at each stage of using an interface or a product — and translate that into user experience.
This is why we often refer to that field as user experience design. It’s everything from the words that they see to what they were doing right before to what is most prominent in front of their face. What problem are they trying to solve? What are they going to do after that? What are they expecting to have happen?
These are all skills that take practice, and Garry, you’ve alluded to that. When you’re starting out, you design things, and you think, “This is great”. Then, you test it with users, and they get stuck on it at first.
Garry: They’re like, “I don’t get it”.
Jen: Yeah, they’re like, “I’m stuck on that page one,” and you’re like, “Oh gosh, OK. I’m the world’s worst designer.” I think it’s just something that makes you used to not being right all the time and being open to other perspectives. It also forces you to try to think of what those other use cases might be.
When you’re handing things off or working within an engineering team, that’s the strength of that team, thinking, “Hey, how do I write some code that accounts for all of these different things that might happen and how do I do that elegantly and simply?” It’s a really difficult and hard job to do, which is why good engineers are hard to find and why they’re so highly valued on a team.
The design part is very similar in that you have to think through all of the steps and think ahead. You have to think, “Hey, what’s going to happen if these five things all go wrong? What experience will the end user have?” This translates into a lot of the skills that I use to work with startups: find teams that make sense and try to look for diversity in how people approach problems and think about things and try to match those all together. That lets you see all of the different aspects of a problem or opportunity without getting tunneled into designing something for yourself.
On diversity and design thinking
Garry: There is actually a relationship that is a little bit of a circular cycle. If you start with more diversity, you’re going to have more micro conflict. In order to come to the right or most beneficial resolution to that conflict, you need more empathy. So more design thinking and more empathy. That allows you to let in more diversity, and then, it’s a cycle that fits together so well. The outcome of that is a superior product, or one that basically does better or does something that other products or other teams don’t do. That seems like one of the core, recurring themes in your career and what we’ve been building together at Initialized.
Jen: There’s a lot written on how to manage people and manage teams, and there’s a lot of really good tools on how to have one-on-ones and how to talk to different people. I think what happens when you get diversity is you need another set of skills, which is not all people are managed and motivated in the same way. Even if you just look at the Initialized team, we have people at different stages in their careers and a lot of very senior people.
So how you manage someone vvery senior, who’s very high performing, is not the same as how you motivate someone who is making a career switch into investing or is just getting started in terms of things. I think you use a lot of different tools that we talked about before: empathy, really understanding what motivates the other person and what their goals are. That’s what makes a really good manager, co-founder or teammate.
In order to work together, think about: what is it they’re bringing; what is it you’re bringing; and how did those two pieces fit together really well. I think that’s how you get more exponential value out of teams. There’s a little bit of early effort that you have to put in to calibrate the tool. From there, once it’s calibrated really well, it works about 10 times better than if it was just struggling along at the beginning or just doing the same task over and over, the same approach over and over. I think that’s where a lot of the magic happens.
Garry: You’ve been a leader at Initialized around making sure that we make diverse hires and that we are continuing to fund diverse founders. Before this, we were talking about how you’re leading the team in terms of the highest number of female founders and underrepresented backgrounds for founders in the companies you funded. How did you do it, or how do you think about it and how should founders think about it?
How to do diversity right
Jen: A lot of how I’ve funded so many female and underrepresented founders happened organically. Part of it is that being open to alternate approaches and perspectives does really help a lot.
I think both in our hiring and how I personally look at things is to try to widen the funnel or the sourcing at the front. The more diversity there is coming in, then the more gets through all the way at each stage of things. I think we all agree there’s a lot of interesting ideas and experiences that come from all places. It does start to get a bit of a flywheel going where those founders that I work with talk to other founders or see other companies in the portfolio that they think are great companies and they want to work with the same investors that funded those companies. It’s a mix of some intentionality but also just keeping your eyes open and trying to understand things that might not necessarily be in the exact way you already perceive them from the start.
I always do talk to our founders about how diversity is important early on. For founders, it’s important to think about diversity for their teams early on because if you get to a point where you have even eight or nine people that are all the same gender or the same school or the same approach, it’s a little hard to be the next person that comes in to that team, right?
It’s a little scary to be, for example, the first woman if there’s already 10 or 15 guys that are working together for some time on the startup. It’s a little bit like, “I don’t know if this is going to be a great experience for me. Should I take this risk or not?” That’s something that happens very accidentally sometimes in startups because you’re moving fast and you’re trying to solve problems. Then, quickly you get into this state where it becomes much harder to correct when you’re trying to go from eight to 25 people and you want to add diversity at that point.
It’s something to always be thinking about because those first hires are very important. They set the culture of the company, and they attract the type of people that you want to have join the team. You want to get that exponential aspect early on and not wait until the end where it’s very difficult to try to convince someone to be the first person that’s not exactly like everybody else who works there to join. That’s putting a lot of burden on that person, and it becomes much harder to hire. Start as early as possible, and think about what culture you want and what background or experience those people can bring to make the team stronger, better, faster and more unique in a lot of ways.
Garry: It sounds like not everyone, especially at pre-seed, can do this but certainly increasingly at seed and definitely at Series A, when you have more capital to devote to hiring and hiring recruiters. Implementing Rooney Rule — making sure that 50% of the pipeline, your top of funnel, phone screen and a final interview is diverse in some way — that’s really the best practice, and you might have to spend money on recruiters to be able to implement that.
Jen: I think it’s back on making it a priority. If something’s priority, you put resources towards it and make it happen.
I think even with our own experience, Initialized uses a lot of different recruiters to help us hire. In some fields, I still have to push and emphasize that this is important to us. Even though the field itself is primarily not diverse, I still want to explore options for finding people from different backgrounds or different locations. I think the other thing to think about here too is that diversity can mean a lot of different things to different teams. It’s important for your team to understand where your blind spots are and where you want to fill them in.
At Initialized, we regularly have off-sites where the team gets to weigh in on diversity and our priorities. The investing team is 50% women right now so that is not as much of an issue for us, but we may have other areas where we want to focus on diversity. So, as a team, we talk it through and adapt what we consider diversity to be or what the priority of that diversity is at any given time so that we continue to round up the team and make it better and better.
Neither of us planned to be VCs
Garry: Taking a step back, you and I are both examples of people who tend not to get to become venture capital investors. I came in as a designer-in-residence at Y Combinator, having no real sense that I wanted to become an investor. I remember meeting up with you shortly after I made the leap from designer in residence to venture partner at YC. You were asking me about how to become a design partner at a venture firm. The interesting thing since 2011 is that many of these roles came and went, and now, we get to run this firm together. We’re the investors who use design in our thinking instead of being designers working for the investors, which is cool.
Jen: I work with a lot of different designers and design leaders, and I think a lot of them reach a certain point in their career where they ask, “Well, what’s next for me, Head of Design or Global Head of Design?” I might be at a very large startup and scaling large teams and things like that, but there aren’t as many design roles as there are engineering roles. The later stage career opportunities are not as clear for those team members. I often talk to them about where they can go next or what they should be looking to do. Sometimes, it’s more to go on the product side like I did, which is to say, “Hey, I’ve got these design thinking skills, and I want to apply them to more of the business or the product side of things.” And other times, it’s just realizing that even though you’re “just a designer,” you can start a startup; you can build things; and you have most of the skills that it takes to build a business and understand what people want.
That is something great for building a startup, but then, it also is something great for investing as well, which is thinking about whether people will want this product, understanding how these founders might solve problems or how they think about product and design. These are all skills that make someone a great investor. Garry, you’re an excellent example of that. A lot of what we use today is our design thinking or design skills, product thinking, and we apply those to the investing realm instead of building a specific product.
Garry: Well, I’m so psyched to be able to build this firm with you.
One of the things that you really pushed us to do was to open the search app for not just operations and advising companies’ operating roles but literally the investor role, the Principal and Partner roles at our firm, which is probably the least open sort of thing that most venture firms ever hire for. Most of the time, a lot of firms just say, “Well, who do we go to college with?” It’s that kind of thing, right? It’s a very closed job posting. They don’t exist, let alone an open one with a transparent process like this. Thank you for pushing us to do this. I’m already blown away at the quality of candidates that we’re getting. How do you think about this? We’re going to be talking to lots of folks, so how do you think about values and who we want in this open search?
Building the investing partnership
Jen: We work very much as a team, and I think that comes from our operator startup backgrounds. It is different from a lot of other firms who say they’re a team but still work very independently from one another. We work very closely across all the companies, across all the portfolios that we’re investing in and advising and operating.
Getting people who are very collaborative and able to work with other people, who are empathetic and most importantly, very focused on impact is super important. Those were a lot of the skills and the attributes we talked about earlier that you and I developed from working in design, product and engineering. A lot of that means these aren’t traditional backgrounds that investors normally come from.
So how do we find these people? How do we attract them? How do we let them know that they could be a great fit for Initialized? I think in many cases, especially on the Principal side, they may have never considered that this is a great path for them or that a venture firm even has such a role. To some degree, advertising it or making it more prominent is a way for us to show people this is a great way to translate your background into helping other companies, working with companies.
That’s the part I really love about investing — getting to work with the companies over a really long period of time. There’s the finding of the companies and the funding of them. That’s super exciting, but to me, the really fulfilling part is just working with them through all the ups and downs and seeing them succeed and seeing them try again and again to build something. It’s really inspiring to me, and it really fits in with my background.
That’s why finding people who enjoy that work and have that empathy is something where, “Hey, let’s put that out to everybody and see what they, you know, who that resonates with and who wants to work in that environment,” is a good approach. We want to find the best people, and the bigger the pool of people that we can look at, the better. I’ve only done the early reviews of a lot of the applications, but that message resonates with a lot of people. Even if they’re not a perfect fit for Initialized right now, that message resonates with them, and they might end up growing their skills and being a great fit for us later or being able to take those skills to one of our portfolio companies as well.
What makes Initialized different?
Garry: I think there’s really three things in my head. The first thing is I think that Initialized can be the firm that’s basically made of builders. I wish that that wasn’t weird, but seemingly, it is.
Second, what I think that unlocks is that founders, who have choices, are going to choose builders over all the other archetypes of investors. I also think builders are better at picking. One of the things that I feel like we always talk about is when you sit across from a team that’s trying to make something that never existed before, the number one question I always ask — and I think you do this too — is: if I wasn’t working on this right now, would I go work at that company? Is it something that matters? Do I believe that they’ll be able to make a big difference, and are they people who I would go work for or follow?
The third thing there is if we are builders and we have that affinity, then we’re also going to be way more understanding of if things don’t go well. I’ve never seen a startup have things go perfectly ever, even the ones that are worth tens of billions of dollars today. I guarantee you every single one has hit some sort of rock bottom, and that’s when the nonbuilders just evaporate. They’re just like, “Oh, I guess we scratched this lottery ticket, and it just didn’t work out, so I’m just going to stop responding to them.” I can’t believe that’s how investors treat some of their startups, but they do, and that’s sad. My goal is if we have the right people who are builders, we’re not going to give up at the first notice of something not quite working. We will have seen this ourselves in our own startups, and then we’ll say, “Oh, that. We’re going to fix it this way, right?” And I think that that’s something that founders really enjoy.
Jen: We like to apply that to a lot of our processes and how we do things at Initialized as well. I think because we’re all from a very startup culture, we need to be organized and have structure, but we do it in a very agile way. We understand that change needs to happen, and we need to be able to move quickly; we just want to do it in a thoughtful and purposeful way. So we really do try to meld both the more modern way of doing things, which is moving fast and taking opportunity when we need to with a very thoughtful and structured approach, so it’s not total chaos.
That’s actually coming from our DNA of trying to mix what’s best about startups and action with building systems that work for people because we still have to work together and not get burnt out and create a lot of after burn; that’s what we work on as a team, internally as well, so that we can be the most effective team to work with the founders that are very much like us and very much also going through a lot of those ups and downs of building something.
Garry: Thanks for hanging out with me here. Obviously, we get to work together all the time, so it’s funny to say that. I’m glad that my audience gets to know you through this blog and our YouTube video because we really are trying to make something totally different with Initialized.
What does Jen wish she knew at age 18 or 22 starting in tech?
Garry: One of the traditions we have on the channel is what would you say to the 18-year or 22-year-old version of yourself entering tech and your career?
Jen: Hearkening back to the very beginning when we worked at Adjacency together, it was a special time, and I didn’t fully realize it at that time because it was one of my first jobs. It was special because it was a combination of a lot of really talented people focused on a vision, and it had that feeling of momentum and excitement. Since then, I’ve worked at a lot of places where that wasn’t necessarily the case.
I think it’s very similar to our portfolio founders trying to find product market fit, right? You need to find the right mix of people to create that special mix of art and science to build something amazing that changes everybody who works on it but also hopefully the world or the world for some important group of people. I think that takes a lot of time and work, and it’s a special combination of things, so that doesn’t just happen without any effort. It’s a similar feeling like, “Hey, things are very much aligning. All the momentum is starting to happen. All of the things everyone has worked on for a long time is starting to prove out.” It’s all been a lot of work and a lot of purposeful organization of people and ideas. So it may suddenly seem to happen quickly, but actually, all that effort is what makes that happen. That’s similar for portfolio companies. It’s for Initialized, and it’s from that very first experience when Garry, you and I met each other so long ago.
Garry: Jen, I can’t thank you enough for the chance to work together and the chance to try to make something totally different, totally unique, something that could help a lot of people build startups that touch a billion people. Thanks for coming on the channel today, Jen.
For more conversations like the above, along other leadership and startup topics, be sure to check out my YouTube channel and subscribe.