Two Minutes With Annie Shapiro of Inspired Capital

Growing up in California’s Bay Area, Annie Shapiro got to witness the advent of the tech boom firsthand. Now, as part of Inspired Capital, she spends her time helping up-and-coming entrepreneurs make the connections they need to grow. In a recent sit-down, the charismatic VP of platform shared some of her thoughts on the keys to managing people, potential business pitfalls, and the unlikely connection between art history and venture capitalism.

  1. What do you need to start your day?

    I love The New York Times’ Spelling Bee puzzle. I try to avoid caffeine, so it gets my mind going in the morning!

  2. You have a background in art history. How did you end up in VC and tech?

    I grew up in the Bay Area, so I was surrounded by tech without even realizing it. I started interning at LearnVest while I was a sophomore in college and immediately fell in love with the process of building a company from scratch. I joined LearnVest before we even launched a website and saw it grow to one of the largest fintech acquisitions of the decade. Now in VC, I get to partner with founders who are in those exciting early days themselves.

  3. Were you able to apply any of the skills you’d cultivated as an art history major?

    Absolutely. So much of art history is digging into the backstory and context of something visual, particularly art that might seem simple on the surface. It was a lot of research and translating abstract ideas into a clear narrative. Both skills have been helpful in a tech career that’s mostly focused on marketing.

  4. In the past, you’ve described your introduction to the startup world as a “tour of duty.” What was the most important takeaway from that time in your career?

    So many roles within startups are incredibly niche. Without getting exposure to a wide range of opportunities, it’s hard to identify your strengths and even know what roles might be a good fit for you. By joining LearnVest so early, I was able to take on a generalist role, where I got to dive into whatever area of the business had the greatest need. I spent time building out a customer support system, learning how to lead business development calls, running user testing sessions, and owning our social media channels. By doing a little bit of everything I learned 1) that having variety day-to-day is important to me, and 2) that marketing is the function I’m most passionate about.

  5. Where do you look for inspiration, and what’s the last thing that inspired you?

    I’m most inspired by people’s stories. I am an avid podcast consumer because I think it’s such a phenomenal mode for storytelling. I’m lucky enough to produce a podcast—Inc. Founders Project with Alexa von Tobel—and I regularly take inspiration from our guests. One recent example is the founder of Expensify. He talked a lot about the importance of hiring people who have a life purpose outside of work, because it actually drives them to do their best work.

  6. If you weren’t in your current position, what would you be doing?

    I have always loved baking, so I would love to work in the food industry. I contemplated going to pastry school years ago, but settled for a few weeks of cooking classes in Italy to tide me over!

  7. You’ve played many roles in your career, from marketing director to talent manager. What’s the key to managing people?

    I spent a few years at Namely, an HR tech company, so we thought an outsized amount about people management. I think ongoing communication is critical. I had weekly 1:1s with all of my direct reports. Not only did we chat through priorities for the week, but we always built-in time to talk about career development. When everyone knows what they’re rowing toward—both in terms of goals and career path—it makes for a more effective team.

  8. Do you have any hidden talents?

    I’m not sure if either is at “hidden talent” level, but during Covid, I jumped back into two hobbies I grew up with: playing tennis and speaking Italian, and both have brought me a ton of joy!

  9. Inspired Capital was founded to help people fund their ideas. What’s a basic principle of fundraising that can be applied to everyday life?

    Work with good people! It’s a cliché in venture capital, but it really is about the people. As a founder, picking a VC to partner with is a long-term marriage (that ideally lasts a decade and beyond). Surround yourself with people who share your values and are your go-tos, not only in good times but challenging times, too.

  10. How do you handle making hard decisions?

    I am a talker, so I best process decisions through talking to friends, family, and trusted colleagues.

  11. What’s the hardest lesson you’ve had to learn?

    Very tactically, I’ve had to learn how to not be overwhelmed by the myriad things that come my way. I thrive on the variety of my role, but it also means my to-do list can quickly seem unmanageable. Whenever I was stressed with schoolwork, my parents shared the Anne Lamott quote “bird by bird”—there’s a lovely story behind it, but the takeaway is to just focus on doing one thing at a time.

  12. At the heart of every great business is a good idea. But that doesn’t always ensure success. What are some common mistakes that keep businesses from making the most of their ideas?

    There are a lot of reasons companies stumble. One of the biggest, especially in the early days, is having too many good ideas. It’s essential to have a north star you’re going after and to keep questioning whether every decision—who to partner with, who to hire, what to build next—makes sense within that core vision.

  13. The best/most successful businesses tend to solve a common problem. What problem would you like to see more businesses working toward solving?

    We are seeing such a tremendous talent shortage right now. There are a lot of companies going after this space, but I am excited to see meaningful innovation here that will train up more talent in critical fields (engineering, healthcare, etc.) but also find new modes for that talent to bring their expertise to market (freelancers, fractional work, async work).

  14. Finally, a platform is defined as a raised surface on which people can stand. What do you want to achieve with your personal platform going forward?

    My personal platform within Inspired Capital is to be the most helpful resource to the founders we work with and to their teams. We call it the craft of early-stage company building, so I hope that my platform fulfills that ambition to give founders the tools and support they need to make the journey a little easier.

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