Deploying capital into untapped talent through a $50MM venture fund

Founding partners: Janine Sickmeyer & Brandon Brooks (photo by Megan Leigh Barnard)

It was 2013 and I was a young, solo, woman, first-time founder trying to raise capital in the Midwest for a legal tech product that was going to transform the way attorneys were preparing and filing court documents, starting with bankruptcy. I went coast-to-coast pitching my big idea but the questions I got rarely consisted of the product and team. I was asked about my engagement ring and when I planned to start a family, where my technical co-founder was, and what my fiancé did for a living. I applied…


West Tenth & the Unbundling of Local Networks: Personalization as the Next Wave of Commerce

In the last 80 years, the commerce industry has shifted and evolved tremendously, and will continue to do so over the next 80.

The first shift was convenience, led by Walmart, a big box store with which we are all familiar. Their underlying thesis was that rural areas can sustain large box retailers, and consumers should be able to locate everything they need conveniently in a single store location.

The second wave was ultra-convenience — Amazon emerged to give consumers a catalog of products delivered…


Dispo Proves Nostalgia and Delayed Gratification Wins the Popularity Contest

photos taken with Dispo — no filters

The darkroom

I was sixteen years old when I developed my love for shooting film photography. It was 2002 and I was a sophomore at a suburban midwest high school that had over 3,000 students walking the halls. While I was a social butterfly floating my way from one group to another, Photography class was where I was most myself. The darkroom was my safe space.

I learned how to roll film, process photos with the developer, and stop and fix chemicals, and hang them to dry. And like everything I do, I went all in. I didn’t just do…


My team is growing and we’re working on something special! 🚀

When I started my legal tech company back in 2013, the startup space was a little different. I was a solo woman founder in two of the most male-dominated industries (legal and tech). Located in the midwest, I spent my evenings, weekends, and just about any other free moment working on my business and meeting fellow entrepreneurs. I was a first-time founder who was trying to figure things out, scouring the internet for resources and asking tons of questions. Along the way, I did figure things out, but I longed for a community of alike entrepreneurs who supported each other.


Just a couple of months ago, I started the Let’s Start Up newsletter for founders, investors, startups, and friends. I’ve already sent out nine issues and momentum only continues to pick up.

I started the newsletter to expand my network and inspire others with my experiences as a tech founder. I hope that anyone interested in entrepreneurship, diversity and inclusivity, and tech will find something relevant in my posts.

In the words of a few subscribers:

“Hands down it’s the most authentically engaging content to cross my inbox in a while. Thank you.” -Nneoma

“I got my first newsletter from…


To say that 2020 was a tough year is an understatement. We experienced loss in many areas of our lives and were forced to adapt to a new way of living. But 2021 is coming and with that comes more possibilities. A new year is a time to take some time to reflect on where we’ve come and move forward to a new beginning!

The reflection part is so important because it allows us to identify what went right and what went wrong. …


The holidays are almost here! While our celebrations might look a little different this year, a thoughtful and practical gift is the perfect way to brighten spirits. Just a couple of weeks ago, I turned to my network of entrepreneurs on Twitter to gather ideas for this Founder’s Gift Guide.

Whether you’re shopping for friends, a family member, your co-founder, team members, or even yourself, you’ll find the perfect gift that your loved-ones will obsess over. …


Let’s get real for a second. As a startup founder, I read everything I could get my hands on to learn about how to build and grow a company but it was hard to find books for womxn in tech without all of the cutesy, infantilizing “girl-boss” content. I was searching for real stories of people going through a similar journey to me without the fluff. That was a few years ago.

I’ve since discovered that there are many authors and thinkers who provide actual substance and professional content for womxn without forfeiting personality. These 18 books are perfect reads…


An unconventional startup story: I built a web app without a technical background.

33 weeks pregnant with twins // building in public // 4yrs after launch // 1 yr before acquisition

You read that right. I left my job (and security net) to start my SaaS company in the LegalTech space without much knowledge or experience in tech whatsoever. My nights and weekends were spent behind my computer, looking for others doing the same as I was — building. I tweeted and shared every little milestone I hit online.

I was transparent because that’s who I am and it was what I knew. The term building in public is hot right now, but back then I called it “bootstrapping and looking for other builders like me.” Building a startup…


Many of us have been embracing the remote work lifestyle for months. While there are so many upsides to remote work, one of the challenges a company or manager might encounter is employee onboarding. Even if you aren’t actively seeking remote employees, the coronavirus pandemic has made this scenario much more common because of federal stay at home orders and company safety precautions. There are 7 million+ U.S. Remote Workers, and many experts predict that remote work is here to stay. …

Janine Sickmeyer

Founding Partner at Overlooked Ventures

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