#SWAAYthenarrative
Photo Courtesy of Janine Sickmeyer

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
Business

Five Essential Lessons to Keep in Mind When You're Starting Your Own Business

"How did you ever get into a business like that?" people ask me. They're confounded to hear that my product is industrial baler wire—a very unfeminine pursuit, especially in 1975 when I founded my company in the midst of a machismo man's world. It's a long story, but I'll try to shorten it.

I'd never been interested to enter the "man's" world of business, but when I discovered a lucrative opportunity to become my own boss, I couldn't pass it up—even if it involved a non-glamorous product. I'd been fired from my previous job working to become a ladies' clothing buyer and was told at my dismissal, "You just aren't management or corporate material." My primary goal then was to find a career in which nobody had the power to fire me and that provided a comfortable living for my two little girls and myself.

Over the years, I've learned quite a few tough lessons about how to successfully run a business. Below are five essential elements to keep in mind, as well as my story on how I learned them.

Find A Need And Fill It

I gradually became successful at selling various products, which unfortunately weren't profitable enough to get me off the ground, so I asked people what they needed that they couldn't seem to get. One man said, "Honey, I need baler wire. Even the farmers can't get it." I saw happy dollar signs as he talked on and dedicated myself to figuring out the baler wire industry.

I'd never been interested to enter the "man's" world of business, but when I discovered a lucrative opportunity to become my own boss, I couldn't pass it up.

Now forty-five years later, I'm proud to be the founder of Vulcan Wire, Inc., an industrial baler wire company with $10 million of annual sales.

Have Working Capital And Credit

There were many pitfalls along the way to my eventual success. My daughters and I were subsisting from my unemployment checks, erratic alimony and child-support payments, and food stamps. I had no money stashed up to start up a business.

I paid for the first wire with a check for which I had no funds, an illegal act, but I thought it wouldn't matter as long as I made a deposit to cover the deficit before the bank received the check. My expectation was that I'd receive payment immediately upon delivery, for which I used a rented truck.

Little did I know that this Fortune 500 company's modus operandi was to pay all bills thirty or more days after receipts. My customer initially refused to pay on the spot. I told him I would consequently have to return the wire, so he reluctantly decided to call corporate headquarters for this unusual request.

My stomach was in knots the whole time he was gone, because he said it was iffy that corporate would come through. Fifty minutes later, however, he emerged with a check in hand, resentful of the time away from his busy schedule. Stressed, he told me to never again expect another C.O.D. and that any future sale must be on credit. Luckily, I made it to the bank with a few minutes to spare.

Know Your Product Thoroughly

I received a disheartening phone call shortly thereafter: my wire was breaking. This horrible news fueled the fire of my fears. Would I have to reimburse my customer? Would my vendor refuse to reimburse me?

My customer told me to come over and take samples of his good wire to see if I might duplicate it. I did that and educated myself on the necessary qualities.

My primary goal then was to find a career in which nobody had the power to fire me and that provided a comfortable living for my two little girls and myself.

Voila! I found another wire supplier that had the right specifications. By then, I was savvy enough to act as though they would naturally give me thirty-day terms. They did!

More good news: My customer merely threw away all the bad wire I'd sold him, and the new wire worked perfectly; he then gave me leads and a good endorsement. I rapidly gained more wire customers.

Anticipate The Dangers Of Exponential Growth

I had made a depressing discovery. My working capital was inadequate. After I purchased the wire, I had to wait ten to thirty days for a fabricator to get it reconfigured, which became a looming problem. It meant that to maintain a good credit standing, I had to pay for the wire ten to thirty days before my customers paid me.

I was successful on paper but was incredibly cash deprived. In other words, my exponentially growing business was about to implode due to too many sales. Eventually, my increasing sales grew at a slower rate, solving my cash flow problem.

Delegate From The Bottom Up

I learned how to delegate and eventually delegated myself out of the top jobs of CEO, President, CFO, and Vice President of Finance. Now, at seventy-eight years old, I've sold all but a third of Vulcan's stock and am semi-retired with my only job currently serving as Vice President of Stock and Consultant.

In the interim, I survived many obstacles and learned many other lessons, but hopefully these five will get you started and help prevent some of you from having the same struggles that I did. And in the end, I figured it all out, just like you will.