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My Next Move: Why I’m Stepping Back From Being an Operator To Become a VC

Maia Benson
Oct 14, 2022
min read

For the past 20 years, I have been a Founder building new SaaS products for companies that dominate the Entrepreneur/SMB market like LexisNexis, Pitney Bowes and Shopify. Last year, I left the nest and joined the ranks of being a Co-Founder myself, launching NiftyLuxe to open up new digital products and experiences to the luxury fashion market.

Now I’m stepping back from all of this to sit on the other side of the table as a venture capitalist with Forum Ventures.

I know I’m walking a relatively worn path from operator to VC, but for me, it is an extension of a mission I’ve spent decades serving — lifting up Entrepreneurs and small businesses through technology. Venture unlocks a path to scale this mission — more Founders, more technology, more mentors, and more capital.

An operator helping entrepreneurs

My entire career has been focused on helping entrepreneurs, whether small and solo law firms at LexisNexis, small businesses at Pitney Bowes, or omnichannel merchants at Shopify. And I have loved it. There’s no greater joy for me than building tools with real value — the kind that gives Entrepreneurs more time, money, or domain expertise to survive and thrive. Entrepreneurs are trading limited resources that inevitably can be personal (kids’ college tuition, food on the table, rent) for the tools to unlock a return to justify that risk — a truly humbling and the very essence of bravery.

I gained a deep admiration for the risks these individuals take every day to make a living, provide for their families, and make a difference in the world. These folks are the basis of the American dream — 99% of all employment is powered by firms with fewer than 500 employees and these businesses account for close to 50% of our GDP. Entrepreneurs operate without a safety net and see trading this risk for the upside of being their own success story. This is special and foundational to our democracy rooted in individual freedom and choice.

After nearly 20 years of supporting entrepreneurs leveraging the capital and distribution channels of large corporations, I stepped into the co-founder seat of my own company. There I experienced firsthand how difficult it is to get two days of work done in one, how lonely it can be, and how important it is to listen to your own advice and ask for help! I also realized that when you choose to build products in a market (NFT) that is just being born, it takes a community to drive a revolution, and the runway to success can be long.

Finding the right Forum

After spending a year working with the VC community as a Founder, investor and advisor, it became clear that I could scale my impact with bigger checks and a greater operator network with a best-in-class, early-stage VC firm. I wanted the perfect mix of hands-on operating work with the ability to write pre-seed/Accelerator and Seed checks to help see companies from inception through growing revenue traction. I also wanted a firm that had a diverse portfolio, including a focus on next-gen eCommerce and logistics tech.

The good news is there are many amazing early-stage VC funds. The question for me was which one would enable me to provide capital AND meaningful hands-on help to Founding teams? Who had proven this combination and drove outsized returns back to the LPs?

Forum Ventures became the obvious choice. The team has a great track record of success, including early investments in Firstbase and VendorPM. But what really drew me in was their team and culture. Powered by ex-operators and founders with proven experience scaling from the earliest stages to revenue and growth that practices leading with empathy and diversity, two critical elements for nuanced technology solving complex problems.

Logistics, consumer, and eComm… oh, my!

Taking on this new roleI at Forum, I will be a Generalist with a sensitivity to next-generation eCommerce and logistics tech. These two worlds have rich value chains and are still in their infancy in a creator-led, omnichannel, digitally native, I-want-it-now-sustainably, and I-might-buy-it-with-crypto-powered world. It’s also where electrons (software + data) meet atoms (people, process and packages) — electrons being highly easily, fungible and atoms, not so much.

If you’re building in this world, let’s work together: Pitch me your business. Check out our Seed Fund and Accelerator. At a minimum, you’ll get access to our Founder Starter Package, which includes discounts on platforms like HubSpot and Brex.

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