SEATTLE, WA — We are pleased to announce that Nate Doran has joined the General Partner team as Operations Director. Nate is already working on scaling the operations of Mastersfund, bringing a decade of experience in managing end-to-end deal flow for SWAN funds with him. His strong support and innovative approach contribute to Mastersfund’s continuing growth and success.

Interview with Nate Doran

Question: What attracted you to Mastersfund and what excites you most about your new role as a member of the General Partner?

Nate Doran: I’ve been in this business for 10 years. Around 2016 or 2017, I read an article about how very few venture funds were employing AI and automation in their processes and, considering the advantage such integrations would bring to a fund, I began to employ them. Since then, I’ve been writing scripts and code to streamline operations, allowing me to manage multiple funds on my own. At Swan, where we’re on our third fund, and at Mastersfund, where we are on our second fund, I’ve automated many processes for myself and others.

What attracted me to Mastersfund is the innovative approach and alignment with my interests. I have been looking at various investment models, including revenue-based financing. When I joined Mastersfund as an LP in Fund I, both my wife and I were excited. We have two daughters, and I’ve noticed that 30% of the deals I look at are run by women. It’s shocking that only 2% of all VC money goes to women-led companies, but it also represents a big opportunity.

Joining Mastersfund made a lot of sense. There’s a significant market opportunity and I feel good about investing in women-led companies. I can share stories about these great CEOs with my daughters, which is personally fulfilling.

After 10 or 11 years in venture capital, you understand how things work and what the real numbers mean. Getting your money back as an investor is crucial and very few funds achieve this consistently. Mastersfund is attractive to LPs for pragmatic reasons — “dollars and cents” reasons. Women are returning higher ROI to investors; their companies are underrepresented (remember that 2% of venture capital that is invested in women) and underpriced. All this means investors are more likely to see outsized returns by investing in women-led companies

I’ve been sending companies to Mastersfund since we launched Fund I and I kept meeting interesting people at events.

I enjoy this work and now have the privilege of working with some outstanding founders. They constantly improve and drive growth, which is inspiring. It’s not just about why I got in, but also why I continue to want to do this work. I find it very fulfilling.

Question: You mentioned that you have been thinking a lot about AI, even before it became popular, and you’ve been implementing it at Swan. Can you talk more about your plan on implementing AI into Mastersfund?

Nate Doran: There are definitely strengths and weaknesses in what is now called artificial intelligence, which is really machine learning—LLM are a glorified stochastic parrot, basically. My focus with Mastersfund has been on automation. Currently, we’re still fundraising and have a limited budget to invest in human resources to build a large-scale operation. My experience with Swan was similar; we had to DIY a lot due to budget constraints.

At Mastersfund, we’ve been doing things manually at first to figure out the process. I’ve been identifying and estimating how long each step takes, based on my experience over the past 10-12 years. For example, if a task takes three minutes but occurs frequently, it can add up to significant time over a year. By building scripts around these tasks and integrating them into our workflows, we’ve automated many processes.

I’ve written scripts and code for our investment team’s dashboard, saving a lot of time and preventing entrepreneurs from falling through the cracks. This automation standardizes the setup process for incoming companies, saving hundreds of hours per person per year by eliminating repetitive administrative tasks.

Going forward, I want to empower our VPs to focus on what they enjoy—talking with entrepreneurs and thinking about investments. Automation helps them manage their workload by organizing tasks and checklists in real-time. For example, if a VP is working on a deal, they will receive tasks that need to be completed in the next week or two, ensuring nothing is overlooked.

By implementing AI and automation, we aim to handle a higher volume of work more efficiently. One program I’m working on right now for a single step in our process could save 150 to 300 hours per person annually. I’m working on automating every step of the process for each of our team members, which, at scale, already saves the team thousands of hours.

As for AI’s strengths right now, it excels in summarizing and drafting content. However, I don’t fully trust AI to send emails without review. I prefer to use it for drafting, which I can then personalize. We use templates for tasks like rejection emails, where a draft is created for review. This saves time while ensuring we maintain control over our messaging.

In due diligence, organizing documents and financials are crucial. AI can help streamline this process to some extent, but human involvement is still necessary for detailed analysis. We run our investment process on a champion model, where VPs champion the process from start to finish. I believe this approach preserves the discovery and magic of the investment process.

Overall, our philosophy is to remove friction, not the role, by leveraging AI and automation appropriately.

Question: How do you recharge and maintain balance outside of your work at Mastersfund? What hobbies or interests do you pursue?

Nate Doran: For me, recharging starts with getting enough sleep, if I can manage it, and spending quality time with my kids. There’s a real necessity to step back and appreciate what’s right in front of you, and my family life helps keep me balanced.

Conversations with my wife also play a big part in maintaining balance. She’s a working professional and an attorney who often works 78 to 80 hours a week. I encourage her to take a week off once a quarter, and I try to follow that philosophy myself. Taking a week off every few months, even if it’s just to take advantage of federal holidays, helps me step back, reflect, and appreciate things.

In terms of work, it’s about pacing myself and accepting that I can’t get everything done. I focus on the biggest fires and let automation handle repetitive tasks, which reduces the need to worry about every little detail. While I still need to be aware of what needs to be done, technology helps me ensure consistency and reduces my stress levels.