Making the Leap from Operator to Investor, an Inside Look at Lessons Learned

“So, what’s it like on the other side of the table?” In my first few months at Primary, I’ve heard this question a lot—from other investors, former colleagues, healthcare comrades, and—most pointedly—my family. My simple answer is, “It's everything and nothing like I thought it was going to be, but I’m loving it.” My longer answer, I hope, can empower other Operators to make the move—and encourage Founders to ask for more from VCs.

A little about me: I started my career in Finance, but after bschool at Wharton, I spent the past 9 years overseeing P&Ls and teams at companies like EmblemHealth, Quartet Health, and CLEAR. Part of what brought me to Primary is the team’s dedication to remaining Operators, even as VCs. It’s not uncommon for our Investors to spend a full day per week with Founders on building a sales pipeline and process, like I do with Perry Health. Investors on our team are outnumbered 2:1 by pure Operators like Brian Gwiazdowski, for example, who spends his time building and discussing sophisticated finance models that help Founders plan their next fundraise and extend runways. But even with our Ops-centric edge, I’ve certainly had plenty of humbling chapters as I wrap my arms around the more traditional VC aspects of the job.

So here are some learnings—still very much in progress—not so much from “changing” from an Operator to a VC, but from learning to balance both sides of the table to optimize success. While this is my personal experience, I hope much of it resonates for others, too.

Operators just get it

For my fellow Operators reading this, rest assured, operating experience is an incredibly valuable asset in VC when making investment decisions and building trust with Founders. My GTM experience has helped me to quickly assess if a company is going to build the early traction it needs to grow (both commercially and via investor support). Those who’ve lived the experience of building companies from the inside can more quickly understand value propositions and build a stronger sense of whether a business will pass muster with a healthcare organization.

Operating experience also builds empathy with the founding team, which is important both pre and post investment. When competing on a deal, it's an asset to have ‘walked a mile in the shoes’ of a Founder. After a deal, you can share highly tactical feedback and advice that continues to build credibility and trust with the founding team.

Starting at Primary, I knew that my operating skill set was not only valued, but would be put into action to drive value. I recently ran a healthcare BD workshop for our portfolio companies, sharing lessons I’ve learned, good and bad, that you won’t find in a book or article. I’ve continued to support many portfolio healthcare Founders with partnerships, tuning value propositions, building consumer engagement models, and by leveraging my experience building teams and product roadmaps.

Tapping your network and building new ones

Similar to my experience in business development, I need to exhibit hustle and continuously build my network. Venture is a people business and I’m always surprised how small of a world healthcare can be. It’s important to know phenomenal Operators who might one day be Founders or join portfolio businesses, build relationships with fellow investors for downstream rounds, seek out new Founders, and cultivate networks of advisors, customers, and thought leaders. There are always more people to learn from, to help, to partner with.

As an Operator, you can tap into your network in a myriad of ways. As an example, an Operator colleague referred me to a Founder early in their fundraising process. I was able to quickly connect with more than five Operator colleagues and Execs who were either working in similar spaces, could validate the problem, and/or be buyers of the solution. Similarly, I quickly connected with Investors in similar businesses to get their perspective, all of these conversations stemmed from my operating experience.

Learning fast is not just about googling (or using ChatGPT!), it's about talking to potential customers, operational experts, and investors in the space. If the idea of meeting 10 new people a day makes you want to crawl into bed and pull the blanket over your head, this might not be the job for you.

Getting comfortable with a wide range of learnings—and unknowns

Not only do you need to enjoy talking to people, you need to love to learn and be comfortable with context switching. Thus far, venture has been an intellectually stimulating job for me.  When I worked in behavioral health, my primary focus area was behavioral health. I absolutely worked to stay “in the know” on other topics, but it wasn’t critical to my job to be in the know in areas well beyond my core domain.

For many people, context switching between projects is exhausting. In venture, you need to find context switching between entire segments of the industry not just tolerable, but invigorating. You need to be excited to learn about data interoperability tools at 9:30 AM and oncology payment bundles at 10 AM. If you’re not performing diligence on a specific deal, you don’t often spend days building deep SME on any one topic. For many people, this is jarring; and for others, it's incredibly stimulating. That said, you learn SO MUCH as you keep an eye on what's working, what’s next, and how you can support inspiring Founders and amazing businesses.

Inherent in this is that you are also acknowledging that you can’t be an expert in everything, and you need to figure out how to learn quickly. To do that, I advise you to remain humble (always, but especially with Founders who have likely spent 10x the amount of time on their idea than you), be actively curious (ask questions, speak up, put yourself out there), and try to help others (what goes around comes around, ‘take the call’ from other people seeking your experience, advice, or support).

Embrace the VC community

The biggest thing I didn’t expect by far was the community and collaboration among VCs. I didn’t realize how collaborative this network is—until you are trying to win a deal! I did not expect firms to share deals with one another (that was nuts to me, now it makes sense). I didn’t initially recognize that later-stage investors are in essence a seed stage firm’s clients, as we help our portfolio companies receive additional rounds of funding. I knew, but didn’t appreciate, the importance of building great investor working relationships—people you might be on a board with for 10+ years, people you think highly of, and who you think act with integrity.

You learn quickly….but results take patience

Similar to healthcare enterprise BD cycles, understanding if you are a good venture investor takes time...a lot of it. As a person who can be impatient, this was frustrating. I wanted to be a good investor yesterday and I wanted to show value right out of the gate. Luckily, Primary had more patience with me than I had with myself. Here’s a few reasons why things take time:

• You can’t predict when you will complete a deal
• It’s a multi-variable equation when portfolio companies raise capital
• You ultimately don’t know the type or timing of an exit. At the seed stage, this is often a seven year (plus) wait. As an investor, there are fewer quick wins and positive feedback loops.

It's been an incredible journey thus far and I will continue to share what I learn—about VC, healthcare trends, sharing my ‘hot takes’, and of course, tactical insights about my operating experience as an investor. I’m incredibly grateful to the entire Primary team—who continue to inspire me to be the best investor I can be (cheesy, but true). I also want to thank all of the incredible Operators, investors, mentors, family and friends I spoke with along the way about this transition - I’m eager to return the favor, so don’t hesitate to reach out!