Interview With Janine Sickmeyer

Overlooked Ventures: Backing underestimated founders, driving innovation in overlooked industries, and making a social impact. Learn about their investment journey, challenges, and favorite resources, along with captivating book recommendations.

How and why did you get started in private investing?

‍After I sold my first company, a legal SaaS startup, I came upon a lot more free time while transitioning from founder & CEO to employee. I immersed myself further into the startup community looking for what’s next. It was then that I saw more in depth the struggles women and overlooked founders were facing. The industry didn’t look much different from when it did when I was fundraising as a solo woman founder 10 years ago. I began mentoring founders and angel investing women and diverse founders, eventually starting Overlooked Ventures to make an even bigger impact.

What is the single most important thing you value in an investment opportunity?

The founding team. At Overlooked Ventures, we believe in backing founders with the grit and passion that will make the company soar. It doesn’t matter if they’re a first-time founder or if they’ve failed in the past.

What are the best innovation themes that you see in the market today?

We recently refined our thesis to include startups and founders building to solve real problems in industries lacking innovation because there is a great opportunity in these overlooked industries. I’ve come across so many great founders using artificial intelligence, technology, and data to bring much needed change and efficiencies to industries such as agriculture, construction, mobility.

Beyond economic return, what kind of impact do you hope to make with your portfolio?

At Overlooked Ventures, we invest in companies with one or more historically-ignored founder(s). This is an integral part of our fund, and we hope by investing and supporting Black, Latino/a, and women founders we can help to close the funding and wealth gaps.

What’s the most pressing challenge or pain point in managing your day-to-day private investment activity?

As an emerging fund manager you wear many hats; often ones you don’t expect. Reviewing deals, meeting with founders, and investing in the next generation of startups is the best part of being a venture capitalist, however, fund admin tasks are often time-consuming and complex.

What is the hardest investment lesson you’ve learned and/or the biggest investment mistake you’ve made?

It’s been hard to figure out pacing for investments during the market downturn this year. We were on track with pacing and making new investments but as LPs started to wind down on their investing, we had to as well, making it hard to anticipate when we would be able to continue making new investments.

What are your favorite industry information sources and/or services?

Twitter – if you use it correctly and follow the right people. It might take a while to sift through the noise and find your community but once you do you’ll unlock valuable startup and VC resources + insights.

Please leave us a book recommendation.

I’m a big bookworm and read all geners so I’ll drop a few of my favorite recent unputdownable reads that I don’t often see in book recommendation lists:

• The Apotherecene Reviewed – John Green
• A Little Devil in America – Hanif Abdurraqib
• The Great Believers – Rebecca Makkai
• Nightcrawling – Leila Mottley
• Dare to Lead – Brene Brown

What’s your favorite non-business interest or hobby?

When I’m not working, I’m usually playing with my 4 little kids, reading (I read a lot!) or running outside.

What’s your take on the private market overall?

Scored: 10