Molly Gunderson of Freestyle Capital
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While most of us were wading through the wild adjustments of COVID-19 WFH last quarter, Molly Gunderson marked a major milestone: 8-years as the Director of Operations for Freestyle Capital.
In her role, Molly drives critical business and fund operations to help Freestyle function at top form. Additionally, she drives the firm’s annual internship program, recently launched a recruiting pilot program for Freestyle’s portfolio, and is responsible for curating the Freestyle Founder Digest, aimed to provide a bevy of resources and vendor discounts to their ever-growing portfolio.
Molly’s path to venture capital was anything but standard or traditional. Like so many of us tackling this nascent role in the world of VC, there’s a good story behind how she got here.
Back in early 2012, Molly was running point as a hostess with the mostess at The Buckeye in Mill Valley, where Freestyle founders, Josh Felser and Dave Samuel, often frequented and regularly chatted with the General Manager and co-owner, Peter Schumacher. Peter recommended Molly to Josh as a potential killer-hire for Freestyle. He lamented losing her but was confident someone with her level of tenacity and work ethic could help them tackle the administrative and operational challenges of running an early-stage venture capital firm.
Driven by her adventurous nature, Molly accepted the opportunity. She figured a job in venture capital could be a great chance to learn and grow, both professionally and personally. Molly’s vivacious approach to life is one of the primary reasons she immediately fit right in with Freestyle’s culture, philosophy, and approach to investing.
“Molly’s resilient and moves toward challenges, which is the embodiment of entrepreneurship and of Freestyle.”
- Dave Samuel
Her energetic and up-for-anything attitude was instilled by parents who encouraged Molly to get out into the wild and do her own thing, be it on Outward Bound and NOLS wilderness expeditions or in her day-to-day adventures growing up amongst Marin County’s natural wonders. She followed in her Dad’s footsteps, attending college at UC-Boulder and then afterward, heading to South America. There she lived and worked for 2-years facilitating the Universal Student Exchange relocation program in Peru. These collective experiences, coupled with her family’s unconditional support, set a foundation of independence and trust that fuels her courageous spirit and conviction there’s nothing she can’t handle.
Molly has always needed to do something different. It just so happens the audacity to be different is something the team at Freestyle exemplifies:
The company name (Freestyle) clearly defines their approach to investing and to life: we are at our best when we are free to just be. As such, Molly has taken the role of VC fund operations on with her own unique vigor. She has a prowess for managing the multitude of tasks thrown her way and a knack for figuring things out, big and small.
“When you’re the sole employee, everything kind of just falls into your lap.”
- Molly GUNDERSON
Her dependability on the job has been critical to the fund’s long-term growth and success, especially so in these uncertain times. Molly has the grit and determination to see things through, and the partners at Freestyle know there isn’t anything they could throw at her that she can’t handle.
“She is able to move seamlessly from the challenges of managing much of our back-office and the resource needs of our founders to planning our wildly fun corporate events.”
- Josh Felser
Her dexterity is elemental, and the fundamental reason why Josh, Dave, and Jenny Lefcourt (who joined the Freestyle partnership in 2014) trust her to navigate the firm’s day-to-day functions, as well as provide business-critical operations support to their early-stage founders.
“Molly has made herself indispensable to Freestyle founders. They know they can reach out with just about any need or request and either she will have great recommendations or go and find them. Her personality, smarts, EQ, and resources make for a powerful combination that our founders need and appreciate.”
- Jenny Lefcourt
Having gone from zero VC experience (and, admittedly, not knowing what venture capital really was prior to 2012), Molly’s professional growth and depth of tactical experience have been immense.
In recent years, her role has expanded to managing the firm’s investor relations and helping lead Freestyle’s founder focused projects, driving efforts to ensure founder satisfaction and the launch of their (newly announced!) founder wellness initiative. Molly aims to see things from the founder’s perspective while building a relationship with them rooted in trust and mutual respect.
“Molly's superpower is deep founder empathy which translates into an even deeper understanding of core founder needs, both emotional and [in] business.”
- Josh Felser
Taking this innovative approach to founder success brings with it a unique set of challenges, but Molly believes in tackling them with an “ask for forgiveness, not permission” mentality. This grit and fearlessness come, in part, from some of the big wins Molly’s seen during her tenure with Freestyle. Notably, their 2015 investment in Airtable. Molly helped beta-test the product in its early days to provide user feedback and has relished witnessing the company’s trajectory during periods of unbridled growth. Anyone who knows Molly knows she’s a self-proclaimed Airtable “freak” and has adopted the software into her workflow best practices. Now she couldn’t live without it.
Molly’s proven adeptness at wearing a multitude of hats (something all VC operators are required to do!) suits the moxie she moves through life with. In addition to her work with Freestyle’s portfolio—and driven by its success—Molly’s enthusiasm for the investing side of venture capital has flourished. It motivated her to expand her VC skillset and learn about the fund’s deal flow processes, which she now regularly assists with. Taking this on gives Molly fantastic exposure to the tactical aspects of investing, while also giving the partners at Freestyle more time to focus on pursuing and nurturing the startups they’re most excited about.
“Molly manages the whole Deal Close process that I used to do. She does the whole thing and it’s been pivotal for me, Molly, and Freestyle.”
- Dave Samuel
Molly’s willingness to grow and take on more is an inspiring spark plug model of a successful operator. It’s allowed Freestyle to maintain a small, nimble team that’s able to accomplish big things. Additionally, it’s served to foster a culture of collaboration, authenticity, flexibility, and fairness that fuels genuine relationships and informal camaraderie amongst the internal team; something Molly values deeply the more time she spends in VC.
Though she came to the role (and to the venture industry) in a rather unexpected way, Molly has unabashedly blossomed and thrived. She’s added true, measured value to her firm and its growing portfolio, defining what being a first-class VC operator is all about. Her bold spirit, coupled with the creative and passionate team at Freestyle, have perfectly mulled into a meaningful and special tour de force. Here’s to many, many more!
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Let’s Talk Ops (LTO) is a community of first-class operators powering some of the most successful venture capital firms in the world from behind the scenes. We provide connective tissue, mentorship, and tactical support to help members execute at top form across the many verticals they manage inside their funds. LTO also provides high-powered professional development to assist members with career navigation and to ensure the best talent stays. In that vein, we’ve launched our LTO Member Spotlights, aimed to elevate the visibility of VC operator contributions to the venture ecosystem at large.