I am extremely excited to welcome Jenny Fleiss to the Initialized Capital team as a partner. We set out to find a partner highly aligned with our team-centric, founder-focused investing approach who also had demonstrably been through the gauntlet of starting and scaling a company. It’s hard to imagine a better fit than Jenny. From co-founding Rent the Runway, to her strategic role at Walmart, to her extensive time spent investing in and working with early-stage founders, she was an obvious match.

We had clear goals for our search: to find a successful founder with recent operational experience and enough investment experience to apply their knowledge effectively. To be honest, at the outset, I was not sure how prevalent this combination would be in the candidate pool. As I reviewed the hundreds of applications we received through our open search process and saw the depth of talent and experience of many applicants, I found our initial search goals were validated. But even among that strong talent pool, Jenny’s profile immediately stood out. 

Aligning With Our Collaborative Approach

Speaking with Jenny quickly validated the strengths we saw on paper and evidenced deep alignment with our firm’s values, first in her buy-in that investing is best done collaboratively. There are natural incentives that pull venture firms and investors toward siloing and thus it takes intentionality to consistently work as a team. I find that sometimes the value of this is lost on our peers in venture. In contrast, the value is obvious to people who have spent a lot more of their careers at startups, so it wasn’t surprising Jenny was highly aligned.

Jenny’s drive and determination particularly impressed us. We value relentlessness in founders – the ability to persistently and impatiently propel a startup forward, overcoming obstacles along the way. She reminded us of the profile we look for in founders, which gave us confidence in her ability to spot that drive in others and advise our portfolio on what moving fast truly looks like. From speaking with her, it became further clear that she had honed that raw ability to success, spending time talking to early stage founders and choosing to invest in many successful startups along the way.

An Ideal Partner for Early Stage Startups

Jenny’s depth of experience, coupled with her relentless work ethic, positions her as an ideal partner for early-stage startups. She embodies what we value at Initialized: a generalist approach, network-driven mindset, and experience that makes her immediately credible as someone founders should listen to. Her practical experience in scaling companies like Rent the Runway and Jetblack (a text commerce platform she built for Walmart) offers invaluable insights for our portfolio founders, especially in navigating complex logistical challenges.

It’s truly a pleasure to have the opportunity to work with Jenny directly, but I’m equally enthusiastic about introducing her to our portfolio and network as a representative of the firm.