From founder to full-time VC.
Today, I am excited to announce the next step in my investor journey as General Partner at Flybridge. At Flybridge, I’ll be focused on investing across the full range of B2C and B2B opportunities with a specific interest in community-driven companies, commerce 3.0 (logistics, discovery, payments, social commerce, small business solutions), marketplaces, and the everyday economy. I’ll also be continuing my work with XFactor Ventures (a pre-seed and seed stage fund in partnership with Flybridge backing female founders) and will be providing support to our growing community of entrepreneurs and investing partners.
How I Got Here:
Nine years ago, I was standing with my cofounder, Christine Rizk, in the hallway of a hotel conference center next to a large poster of a handbag we had printed at Staples that morning. It was our first time pitching our company- an Ecommerce marketplace to change designer clothes into cash for a cause. The poster was designed by me (a law student) in Apple Pages, our “donation kits” were blank USPS flat rate boxes with poorly printed instructions taped to the front, and to make things even more cringeworthy- the name of the company at the time was Swapfish. But, it was 2011, and we were full of entrepreneurial optimism and undeterred by our lack of design, experience, or even a quality laser printer.
A week later, something remarkable happened; the donation kits we handed out started coming in. I distinctly remember the excitement of opening those boxes and thinking maybe we were onto something. If people would donate designer bags and dresses through such a rudimentary system, imagine what would happen with branded kits and a website?
What followed that night was an incredible entrepreneurial journey of building and scaling a consumer marketplace to tens of thousands of items, negotiating and launching national partnerships with major retailers, celebrities, and thousands of nonprofits, navigating the complexities of reverse logistics, learning the intricacies of wholesale, managing an ever expanding team, three office moves, a sprawling warehouse, multiple millions in funding rounds, and an ending that was far from textbook.
A few years later, I would do it all over again with my second company- this time building a community-driven marketplace to discover emerging products made by women (h/t to my cofounder Vanessa Bruce!) and learning valuable insights into the distinct needs of small and medium sized business owners.
Through it all, the most important lesson I learned was about people. The key to building a successful company isn’t a business model, a killer product, or a well-crafted marketing plan. It’s who you choose to bring with you on the journey. This initially sparked my interest in venture capital- I wanted to be that trusted partner to cheer on founders as they turn their vision into reality.
My Adventure into Venture Capital:
Over the course of my first company, I pitched to what must have been hundreds of investors spanning Boston, NY, and SF. However, even with my best efforts, only 2 of the 60+ individuals on the cap table were women, a direct result of how few there were on the other side of the table.
In January 2017, I set out to change those stats and took my first leap into investing. I was fortunate to find an incredible partner in Flybridge and Chip Hazard, who shared the belief that female founders were building big, meaningful companies. Together, we created a model for a fully distributed VC fund, recruited nine amazing partners with a broad range of expertise (all women operators who had succeeded in the trenches), designed a masterclass in venture capital, and launched XFactor Ventures. Three and a half years later, XFactor Ventures has now grown to 22 investment partners across six cities and has made nearly 60 investments, making it one of the most active pre-seed & seed stage funds backing female founders. Through XFactor, I’ve had the chance to discover that the skills I had developed as a founder of seeing around corners, mapping trends, building a network, mentoring, and identifying talent and opportunities are all skills that made investing a natural and easy transition. Most of all, I love working with ambitious entrepreneurs at the earliest stages of their companies and having a chance to be the type of partner I would have wanted as a founder.
That leads me to today’s announcement and why I’m joining Flybridge. I’ve had the opportunity to work closely with the team over the last four years- building and scaling XFactor Ventures, as a founder in their portfolio, and spending a year in their office literally watching Jeff Bussgang work all day (the walls were glass and my office looked into his). I was continually inspired by Chip Hazard, Jesse Middleton, Jeff Bussgang, and David Aronoff’s judgment, integrity, advocacy, and the deep relationships they formed with their founders. People matter, and they are some of the best around. It’s an honor to be joining this team.
I’ve also seen first hand in my career, the power of community, which is a key part of our thesis at Flybridge. Initially, as a part of the Techstars Accelerator where my first company got its start, and in building that company to a marketplace spanning 36 countries, 2000 organizations and over 150,000 supporters. Next, I saw the valuable connections made across the hundreds of small business owners and tens of thousands of shoppers throughout the Dough community. Finally, community was at the core of XFactor Ventures, where our network of talented investment partners have seen 4000+ companies and provided mentorship and guidance to hundreds of early stage founders. I’m looking forward to building and expanding on this thesis as a part of Flybridge.
I just joined the ranks of VC Twitter (@AnnaBPalmer) 👋. Over the next few weeks, I’ll be sharing more about my investment thesis, what I’m looking for, and my personal fundraising playbook I used as a founder. If things get wild, I may even throw in a picture of me in a Patagonia vest just to make this announcement official. I believe strongly in expanding access and opportunity and so if you’re a founder building a great company, especially reimagining commerce, marketplaces or one that is driven by community, DM me- I would love to chat!