Welcoming Molly O'Shea to the Investment Team

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The Upfront team continues to grow; this week, we’re thrilled to introduce Molly O’Shea as the newest member of the investing team.

Read on to get to know what Molly will focus on at Upfront, what she learned as a founder herself, and why LA is the best city for venture and tech now.

What’s your scope at Upfront? As an Investor at Upfront, I’m working alongside our partner Greg Bettinelli who spends a majority of his time studying the consumer with early investments into Ring, thredUP, GOAT, Rally, and Loupe, just to name a few.

We’re leading investments at the earliest stages which lends a great deal of responsibility to portfolio management, sourcing opportunities and researching new areas of interest. With portfolio management that means supporting our founders and their teams with recruiting top talent, business development/strategy, partnerships, and downstream fundraising. For sourcing opportunities, I’m speaking with founders, investors, operators, students and anyone in between, as well as keeping up on my own reporting with my newsletter Sourcery (a must follow)!

Is there an area of particular interest for you when sourcing? Greg’s superpowers are in the marketplace and commerce arenas, so we’ll particularly be spending time on those categories exploring how they translate into the next cycle of the internet, or as some may call it, Web3. Whether Web3 and the world of decentralization succeed or fail, it has made massive impacts on the market and consumer in the last year, and more so in the last couple of months. We want to understand how the transition to Web3 fits into daily life, what that means for identity(ies), the consumer, enterprise, the outputs (DAOs, NFTs, etc) and if there is some category that will actually endure. Not just shuffle from one table to the other.

We’ll also be diving into new areas of interest such as the consumerization of climate, and enthusiast categories, among others. My inbox is open: molly(at)upfront.com

What excites you when meeting a new company? Apart from the opportunity to meet incredibly smart individuals on a daily basis, each new company we meet helps us understand a larger narrative about a category or opportunity. And as nerdy as that sounds, I find it very exciting. It takes a number of elements for something to “pass go” or to unlock an insight about a space, like the founder’s vision, why now, why are they the right team to build it, can it scale, can they recruit top talent, etc. It’s like a game of Tetris, you’re looking for the right shapes to fit together at the right time. Sometimes they don’t, there are weird gaps, and the game is quickly over. And then sometimes, but much less frequently, they all fit and you can continue to play and reach a higher level. It’s a continuous process, just like startups and investing, and ultimately you begin to gain pattern recognition, apply your insights and leverage the experiences to the next one.

What’s a practical piece of advice for founders and entrepreneurs? Start now! Get reps in and start making mistakes. I recently attended an event here in LA where Fred Ehrsam of Coinbase spoke and his piece of advice was to start tinkering and playing around, to make toys, and to have fun with it, because even the smallest things can have a big impact and the journey along the way of learning and meeting new people can be wildly valuable.

You’ll also start to realize even the most seemingly ‘successful’ entrepreneurs started with nothing, sometimes knowing nothing about their space, but they got curious, and they began to spin their wheels and built their networks, bringing life to their ideas.

What one lesson did you learn as a founder that you wish you’d known sooner? A lot of things, but the top two would be to lean into what you don’t know and to be open minded about meeting new people. During undergrad one of my program directors at the NYU Entrepreneurship Lab, Frank, said that he believes your luck increases with the amount of people you meet, and to start talking to humans. He literally wrote a book on this. And I’d say it’s worked quite well for me so far. You’d be surprised how much you can attract and what starts to come to you when you begin to put things out in the world. It’s also pretty freeing once you open your mind up to opportunity around you.

You just moved to Los Angeles. Why is LA a great city for venture and tech? I think to add to the question, why is LA a great city for venture and tech now? There is no argument that LA is the epicenter of entertainment and creatives, but what we’ve seen through the pandemic is how resilient and valuable those categories are to the consumer and the greater fabric of the economy. For example, TikTok blasted off and now those creators are expanding their footprint with other businesses/partnerships, investing in other creators, unlocking new categories of the market, and shifting archaic power dynamics around.

And, on top of that, people can now choose where they want to live, and what’s better than 365 days of 70 and sunny? Needless to say, talent is flooding to LA. I, for one, am almost a month in and am loving it. I was in NYC for about eight years and don’t know how I made it that long!

__Lastly, what’s a non-work passion you have? __ Art, architecture, fresh air. And it’s great when you can combine them all and visit The Getty, LACMA, Eames Foundation, or Stahl House here in LA, or on the east coast Storm King, The Highline, Dia Beacon, or stroll up/down the Hudson River Park Path.

It’d be wrong not to mention Upfront’s office is here in Santa Monica – the indoor/outdoor design and furniture does not go unnoticed, it’s pretty incredible.