Originally published on Forbes.com
This Trailblazers series takes a look at the pivotal milestones that make up the life trails of inspiring women from a diverse array of backgrounds and experiences. We all know what social media profiles display about the end results women have achieved. This series is intended to take a deeper, more authentic look at the journeys they have taken to get there.
Janine Sickmeyer is a founding partner at Overlooked Ventures, a new venture capital firm focused on supporting and investing in early-stage companies with historically ignored founders. While many investors miss opportunities and perpetuate existing cycles of wealth due to pattern-matching and closed networks, Janine and her venture partner Brandon Brooks have set out to support the next generation of diverse startups through capital, resources and connections. Janine started angel investing after selling her bootstrapped legal tech startup in 2019, with a focus on funding women and Black founders who have struggled to get their first check. She is also a soon-to-be author and a mother of four.
After learning more about the trail that Janine has blazed, I got the chance to ask her some questions.
Rebekah Bastian: Your career journey has spanned several industries so far, including paralegal, photographer, entrepreneur and investor. Did you always imagine a nonlinear path for yourself?
“I find so much excitement in starting something new and building it from the ground up”
Janine Sickmeyer: I’ve always enjoyed building and creating, so naturally I’ve always navigated towards careers that have allowed me to do just that. I find so much excitement in starting something new and building it from the ground up, so when I was working as a paralegal and identified an opportunity to build a software from scratch, I did it. For years I poured everything I had into my startup, and that led to a successful exit via acquisition. Afterwards, I was ready for my next challenge and found so much joy in helping, mentoring and advising emerging entrepreneurs. I believed so much in some of the founders I was working with that I wanted to become a part of their journey as more than just an advisor, and that’s when I started investing. To me, my career path feels pretty linear actually.
Bastian: You’ve been really open about the things that didn’t go as expected in your entrepreneurial journey. How does talking about the rejections and failures that come with being a founder make it easier for those coming up behind you?
Sickmeyer: Entrepreneurship is glamorized. The most popular stories are about the successful entrepreneurs who come from wealthy families or have a safety net to fall back on. But in reality, most people who start a business do not have a paved path to success. These stories can give people the wrong idea and make them think that they have to fit into the status quo to be an entrepreneur and to successfully start a company. I am sharing my “untraditional” entrepreneurial journey openly to show people that they can be a founder, even if they are part of a historically ignored group or aren’t wealthy. I hope that my background, failures and rejections will give people the right idea about entrepreneurship: It isn’t easy. You will mess up a few times. But with enough resilience and tenacity, building a successful company is possible. I want those people who are unsure or don’t think they have what it takes to know that they can take the leap, no matter their background.
“I wasn’t taken seriously, partly because I’m a woman, and was repeatedly told “it’s just too early” or “where is your technical co-founder” or “the market is too small.” “
Bastian: How did your own experience with struggling to raise capital for your startup inform your approach to working with founders as an investor?
Sickmeyer: Even though I didn’t end up securing funding, I spent months cold emailing, pitching to investors, and taking any meeting I could get. I learned a lot along the way, refined my pitch and business idea, and ultimately all of that helped me grow my company to acquisition. Although things ended well, I won’t sugar coat my experience raising capital. It was difficult to say the least, and so frustrating. I wasn’t taken seriously, partly because I’m a woman, and was repeatedly told “it’s just too early” or “where is your technical co-founder” or “the market is too small.” It was so hard for me to convince investors that my idea was solid and that they should invest in me. My somewhat negative experience raising capital, gives me a more understanding and empathetic approach to being a VC and investing in startup founders. Overlooked Ventures is a founder-friendly venture capital firm and we believe in supporting entrepreneurs beyond just an investment.
Bastian: Why do you think there is such a disconnect between the $4 trillion opportunity to invest in diverse founders and the current homogenous investment landscape, where only 2.3% of women and 0.67 of Black founders received funding last year?
Sickmeyer: To understand the lack of funding in diverse founders you have to look at who is doing the actual investing; i.e. the fund managers, investors, and VCs. 72% of decision-makers in VC are white men, and only 4.9% of VC partners in the U.S. are women. It’s clear from these statistics that the diversity problem in venture capital is trickling down to who gets funding. Diverse venture capitalists invest in diverse founders. We need more diversity in VC to change the way funds are being allocated and seize this massive opportunity!
“End every interaction with an ask.”
Bastian: What advice would you give to founders that need capital to grow their companies but are hitting walls trying to find it?
Sickmeyer: Remember, securing VC funding is one way to build a company, but it certainly is not the only way. While bootstrapping isn’t the easiest way to scale your business, many people have done it before and you can be successful. As a bootstrapping founder myself, I found ways to be scrappy and creative in my approach to building my company and taking it to acquisition. If you still want to go the fundraising route and are hitting a wall, I suggest you start by taking as many meetings as you can – and no I don’t mean pitch meetings. Ask people in the industry—founder friends, advisors, mentors, investors—for their advice, honest feedback and introductions. End every interaction with an ask. And do your research to find investors with an open inbox. I like to say that I always have at least one email out in the wild that can change everything for my business. Put yourself out there, you never know what can happen!
Got an ask? Connect with Janine to start a conversation and/or appreciate her journey!