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82 VC Rejections Later, This Mompreneur’s Startup Was Acquired By Fastcase

4min read
Business

If you're someone, like myself, who loves to follow inspirational pages on Instagram then you have definitely seen countless quotes about a very uncomfortable topic– failure.


It's almost as if you're reading the same thing over and over again, but written differently every time. The ole "failure makes you stronger" and "rejection is just the Universe redirecting you." While these quotes are inspiring in the moment, when we actually experience failure in our real lives, we quickly find ourselves ready to throw in the towel and give it all up. However, for one entrepreneur, no amount of rejection or failure were enough to dissuade her from accomplishing her goal of establishing a successful legal startup.

In an interview with SWAAY, mompreneur Janine Sickmeyer talked about her experience in turning her disappointment into determination to build her business from the ground up. She began her career in the legal industry as a bankruptcy paralegal for a law firm in Columbus, Ohio. Over a period of time, Sickmeyer began craving the flexibility that came with being her own boss and later started her own virtual paralegal firm where she prepared bankruptcy documents online for attorneys all over the country. With over a decade of experience working in the legal industry, Sickmeyer realized there was room for a more efficient and intuitive way to meet the needs of her clients and legal professionals that the current, yet antiquated, methods were incapable of doing.

In 2015, Sickmeyer founded NextChapter, a cloud-based web application that allows bankruptcy attorneys to prepare, manage and electronically file bankruptcy cases. With an innovative and unquestionably game changing idea in her midst, Sickmeyer was hopeful that she and her co-founders would successfully build a platform that would receive a positive response from VCs and ultimately lead to funding. However, her reality appeared to be far from that of her expectations.

With little technical experience, Sickmeyer entrusted the CTO position to her then co-founder who took the reins in coding the application. Understanding the difficulties building this platform entailed prompted Sickmeyer to offer as much help as she possibly could despite not being a technical founder. However, her string of seemingly endless bad luck began when her co-founder unexpectedly left the position after realizing how challenging their goal had become. When her second co-founder left, Sickmeyer was taken aback feeling lost and alone. "I took a few days to really process what was happening. That's when I decided I would start learning to code – I would become a technical founder. Because after going through it twice, I knew I couldn't allow myself to depend on someone else to make it happen, said Sickmeyer.

Taking full ownership of bringing her idea to life, she teamed up with developers to work part time and for equity as she taught herself how to code— all while pregnant with her first daughter. With her newfound technical knowledge, she was then able to set realistic development goals such as timelines and tangible product features for the app. Despite things looking up for the CEO, Sickmeyer encountered countless hurdles in her efforts to get funding. After pitching VCs 82 times, she was met with rejection each and every time "Many investors decided to pass on NextChapter because it was too niche. At the time, NextChapter was only built out for bankruptcy law, and investors saw the market potential as too small," stated Sickmeyer. Unfortunately, being too niche was not the only issue investors had with the entrepreneur.

To no surprise, legal and tech industries are male-dominated fields which bring with them their own unique set of challenges to female entrepreneurs who aspire to become leaders alongside their male counterparts. For Sickmeyer, her gender played an unquestionable role in her failed efforts to receive funding. While she admits that these fields have become far more diverse and inclusive of female founders, her initial experience was less welcoming than it is today. "Many times, I felt like no one took me or my company seriously because of my gender. Instead of really listening to me, they would look at the size of my wedding ring or ask me inappropriate questions," said the founder. Despite struggling to navigate the relentless cycling of pitching to different VCs, Sickmeyer eventually self-funded her business without ever accepting any outside funding.

While Sickmeyer's achievements are inspiring, to say the least, her most impressive feat has been overcoming obstacles while raising a family. Just weeks before the launch of NextChapter, she gave birth to her first daughter. Sickmeyer also bore three more children, two of which were twins. As any parent can attest to, taking care of a family is a mentally, physically and emotionally exhausting job, but despite the uncertainty of NextChapter's future, Sickmeyer never allowed her fear of being unable to provide stop her from pursuing her goals, in fact, she was able to reinvigorate those feelings of joy that her work and motherhood gave her. "I found ways to streamline my life and outsource things that don't bring me joy. I don't want to spend my time doing yard work or going grocery shopping. Instead, I'd rather be playing make-believe with my 4 children or working on growing NextChapter," said the mompreneur. Following her passions while making time for what mattered most to her fueled her drive to persevere in spite of her tumultuous entrepreneurial journey.

After losing co-founders, failing to receive funding and being worn down by sexism in a field she aspired to innovate, the tech CEO remained passionate and driven to bring her application to the legal industry. Today, Sickmeyer revels in knowing her hard work and dedication paid off as her beloved company, NextChapter, has been acquired by leading legal publisher, Fastcase. Looking back, Sickmeyer has no regrets about jumping right into the world of entrepreneurship and offers aspiring mompreneurs a little piece of advice.

"Just start up! Sometimes the hardest thing about being an entrepreneur is just taking the leap and deciding to go for it. You are more than capable; believe in yourself and have confidence. I have a blog and podcast where I share actionable tips, including how to find a product-market fit, managing a team and more."

3 Min Read
Lifestyle

Help! Am I A Fraud?

The Armchair Psychologist has all the answers you need!


Help! I Might Get Fired!

Dear Armchair Psychologist,

What's the best way to be prepared for a layoff? Because of the crisis, I am worried that my company is going to let me go soon, what can I do to be prepared? Is now a good time to send resumes? Should I save money? Redesign my website? Be proactive at work? Make myself non-disposable?

- Restless & Jobless

Dear Restless & Jobless,

I'm sorry that you're feeling anxious about your employment status. There are many people like yourself in this pandemic who are navigating an uncertain future, many have already lost their jobs. In my experience as a former professional recruiter for almost a decade, I always told my candidates the importance of periodically being passively on the market. This way, you'd know your worth, and you'd be able to track the market rates that may have changed over time, and sometimes even your job title which might have evolved unbeknownst to you.

This is a great time to reach out to your network, update your online professional presence (LinkedIn etc.), and send resumes. Though I'm not a fan of sending a resume blindly into a large database. Rather, talk to friends or email acquaintances and have them directly introduce you to someone who knows someone at a list of companies and people you have already researched. It's called "working closest to the dollar."

Here's a useful article with some great COVID-times employment tips; it suggests to "post ideas, articles, and other content that will attract and engage your target audience—specifically recruiters." If you're able to, try to steer away from focusing too much on the possibility of getting fired, instead spend your energy being the best you can be at work, and also actively being on the job market. Schedule as many video calls as you can, there's nothing like good ol' face-to-face meetings to get yourself on someone's radar. If your worries get the best of you, I recommend you schedule time with a qualified therapist. When you're ready, lean into that video chat and werk!

- The Armchair Psychologist

HELP! AM I A FRAUD?

Dear Armchair Psychologist,

I'm an independent consultant in NYC. I just filed for unemployment, but I feel a little guilty collecting because a) I'm not looking for a job (there are none anyway) and b) the company that will pay just happens to be the one that had me file a W2 last year; I've done other 1099 work since then.

- Guilt-Ridden

Dear Name,

I'm sorry that you're wracked with guilt. It's admirable that your conscience is making you re-evaluate whether you are entitled to "burden the system" so to speak as a state's unemployment funds can run low. Shame researchers, like Dr. Brené Brown, believe that the difference between shame and guilt is that shame is often rooted in the self/self-worth and is often destructive whereas guilt is based on one's behavior and compels us to do better. "I believe that guilt is adaptive and helpful – it's holding something we've done or failed to do up against our values and feeling psychological discomfort."

Your guilt sounds like a healthy problem. Many people feel guilty about collecting unemployment benefits because of how they were raised and the assumption that it's akin to "seeking charity." You're entitled to your unemployment benefits, and it was paid into a fund for you by your employer with your own blood, sweat, and tears. Also, you aren't committing an illegal act. The benefits are there to relieve you in times when circumstances prevent you from having a job. Each state may vary, but the NY State Department of Labor requires that you are actively job searching. The Cares Act which was passed in March 2020 also may provide some relief. I recommend that you collect the relief you need but to be sure that you meet the criteria by actively searching for a job just in case anyone will hire you.

- The Armchair Psychologist