VC Corner Q&A: Molly O’Shea

Molly O’Shea is an Associate at Trail Mix Ventures, an early-stage venture fund investing in The Future of Living Well across enterprise and consumer startups solving for Sustainability, Care and The Future of Work. She is an e-commerce founder and industry-agnostic technology investor, with experience in early and growth-stage funds and startups. She has had experience at Google’s 30 Weeks an incubator for designers, a family office venture fund in Miami and a APAC cross-border pre-IPO venture fund.

The Startup Grind Team
Feb 4 · 4 min read

— What is your / your fund’s mission?

Trail Mix Ventures is a women-led and owned early-stage enterprise and consumer venture firm investing in the Future of Living Well across Sustainability, Care and the Future of Work.
Areas we are actively researching include Sustainability & Climate, Opioid & Addiction Treatment, Personalized Health, Microbiome, Child & Elder Care, Smart Cities, Frontier Medicine, Supply Chain & Last Mile Logistics and AI/ML Platforms & Services.

— What is one thing you are excited about right now?

I’m excited about many things! But a couple of areas that have endured over time:

  • Solving for the unintended consequences and effects of the rapidly increasing climate crisis
  • Treating the root cause and/or prevention in healthcare
  • Empowering underrepresented individuals
  • Discovering whitespaces that increase efficiency in legacy systems
  • Improving the quality of life for generations to come

— Who is one founder you think we should watch?

While I may not be able to pick just one, all of our portfolio founders display tremendous examples of perseverance, passion and the ability to rapidly problem-solve… But I am a huge fan of Dr. Robin Berzin and what she has built with Parsley Health.

— What are the 3 top qualities of every great leader?

  • Integrity — strong principles, moral compass, honest excellence
  • Openness — humility, knowing what you don’t know, ability to learn & grow, coachability, flexibility, creativity, positivity
  • Perseverance — in leveling up, vision, experimentation, finding product-market fit, execution, passion.

— What is one question you ask yourself before investing in a company?

Is this going to change people’s lives?

— What is one thing every founder should ask themselves before walking into a meeting with a potential investor?

Have I done my research on the investor?

— What do you think should be in a CEO’s top 3 company priorities?

  • Product Market Fit — Who are the customers? What are the driving factors of the business? How can we optimize for that?
  • Culture — Building and retaining top-quality talent, continuously leveling up internal ecosystem and culture
  • Growth — Long term vision, with reasonable and measurable short term milestones

— Favorite business book, blog or podcast?

I’m quite the podcast and audiobook addict. A handful of them that I have on a daily rotation include:

Podcasts: Animal Spirits, Robinhood Snacks, Recode Decode, Goop, Goldman Sachs, MindBodyGreen, The Economist, WSJ’s Future of Everything, and How I Built This

Audiobooks: The Mind-Gut Connection, Crashed: How a Decade of Financial Crises Changed the World, What You Do is Who You Are, High Growth Handbook, Man’s Search For Meaning, Complexity: The Emerging Science at the Edge of Order and Chaos, and Who

Blogs: Scott Galloway, & my lists on medium:

— What is your favorite thing to do when you’re not working?

Mindful relaxation, either on a boat, at the beach, with friends, in an infrared sauna or at the gym (usually listening to a podcast or audiobook).

— Who is one leader you admire?

I’m not sure I can single out one leader, but a quality I’ve gathered over time in leaders I admire is their ability to structure out their goals, level up, level down and have a strong vision for the future. I really admire leaders who take upcoming talent under their wing to empower generations for future leadership. Of my mentors, I’m always so grateful and honestly sometimes surprised by the time and effort they take to answer my texts, calls or emails on the same day. More importantly, they challenge me. They ask me questions that lead me to my own discovery and conclusions, intellectually pushing my personal growth and standard.

— What is one interesting thing most people don’t know about you?

I grew up training as an artist, won local + national awards and showed in Greenwich’s Bruce Museum. I thought I’d become a designer, sustainable architect or developer.

— What is one piece of advice you’d give every founder?

Make meaningful relationships, level up, develop an obsessive growth mindset and write everything down.

— Anything else you’d like to share?

If you’re a phenomenal founder building something incredible in The Future of Living Well reach out to me at

Startups interested in an opportunity to pitch Trail Mix Ventures can apply here.

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