Inspiring Conversations with Chad Billmyer of Inhouse

Today we’d like to introduce you to Chad Billmyer.

Hi Chad, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I’m an experienced operator and product leader with a passion for scaling early-stage, mission-driven ventures, particularly at the intersection of product-market fit and technological transformation. Currently, I apply this experience by serving as a Mentor in Residence for programs at UCLA, Brown University, and StartOut. Additionally, I serve as a fractional COO/CPO for startups like the legal A.I. venture, Inhouse.ai. Inhouse strives to make legal advice, document drafting, and document review more affordable and accessible for small business owners.

A major catalyst for this career path destination was my Federal Work-Study job in college. I ran audio visual services for a lecture hall on campus. In my sophomore year (1999) I worked the AV for a startup pitch competition and discovered that my college gave away thousands of dollars to winning teams. I vowed to enter the following year. Three friends and I entered the competition in 2000 and won. After a few pivots, that venture focused on building software to help college financial aid offices run more efficiently. The business exists to this day and runs at over 800 colleges and has supported millions of families navigating financial aid.

After successfully founding and exiting my first venture, I sought to understand scaling from an enterprise perspective by joining Nelnet, a publicly traded education planning and financing company. I left Nelnet to start my second venture, Panjo, a marketplace that helped the members of auto, sport, and hobby communities buy, sell, and trade. After the enthusiast mobile app, Tapatalk, acquired Panjo I joined Slickdeals. where I applied that scale-up mentality as Head of Product.

Slickdeals is the home of the best deals on the internet every day. As Head of Product at Slickdeals I had the privilege of leading through a period of tremendous growth and supporting the work of brilliant product managers, product designers, lifecycle marketers, SEO specialists, and engineers. I exited Slickdeals just as A.I. was breaking out of its shell. I’m thankful to be engaged with the legal A.I. company Inhouse right now. This work serves as a vital forcing function that allows me to actively define and navigate the rapidly evolving landscape of digital product management in this period of A.I. transformation, ensuring I can bring cutting-edge strategy to the ventures and entrepreneurs I support.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
The road certainly hasn’t been smooth. The exit for my second venture, Panjo, fell short of expectations. It wasn’t the big win investors or I had envisioned. This led to a sabbatical while I figured out my next move. Instead of immediately jumping back in, I chose to apply my skills to a deeply personal mission: running the annual giving program at my son’s LAUSD elementary school. That shift, going from CEO to public school volunteer, was a forced pause that made me realize the power of community engagement and the non-monetary value of my skills. It was a crucial recalibration before I made the leap to a major scaling operation like Slickdeals.

This constant balancing act with my family, however, has made me a much more empathetic and effective people leader. It forced me to move beyond ‘always on’ startup culture and build teams that prioritize output and autonomy over face-time. I learned the essential business skill of setting firm boundaries and how to foster a culture where other working parents don’t have to choose between their kids’ snack time and their career progression. I often ask and arrive at different answers to the questions: What is the opportunity cost for my career to stop what I am doing at 4 PM to prepare my son a healthy snack when he arrives home from school? What is the opportunity cost for my son if I don’t do that?

Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
At the moment, as a fractional COO and mentor in residence, the greatest bulk of my time is allocated to a great venture, Inhouse.ai, a legal A.I. company. Business owners and individuals turn to the platform to draft customer contracts, employment agreements, protect intellectual property, and to get support for a range of other legal matters. I arrived after a phenomenal founding team of Ryan Wenger and Aarshay Jain found product-market fit. There are so many customers of the legal platform benefitting in so many ways that it presents a great and classic product challenge of feature and growth prioritization. The joy at Inhouse is that so many of the problems are the good problems to have.

Beyond Inhouse I am working with a wonderful entrepreneur at UCLA, Nick Kohan, who is trying to improve student access to internships that lead to employment through his venture trylrun.com. As reported by Forbes in 2013, the National Association of Colleges and Employers found that “only 63 percent of graduating students who had held paid internships received a job offer by graduation. As for unpaid internships, students who have them are today hardly more likely to get a job offer (37 percent) than those who have no internship at all (35 percent).” Nick is working hard to fix this broken pipeline.

Meanwhile at StartOut, a 501c3 dedicated to supporting LGBTQA entrepreneurs, I support a spectrum of ventures that range from consumer packaged goods to stuffed animals.

Finally, I recently launched my tiniest startup to date, a 8.5×8.5 inch illustrated children’s book that just won 2nd place in the fall 2025 BookFest awards. “Curly Sue and the Beetle” is a wonderful bedtime story with exceptional oil on panel illustrations by artist Kory Alexander. The book was a passion project. Each time a parent or grandparent shares a photo of their child reading the book it brings me joy given all the hours I put into the story. True events inspired the story of a dog who spends her day searching for the perfect gift to show her love for her boy.

What would you say have been one of the most important lessons you’ve learned?
One of my first bosses at Nelnet, Taige Haines, used to say that she worked for me. She viewed her responsibility as my boss to support my success. That meant she constantly looked for ways to get me the resources I needed and to remove barriers to maximize my success. I loved this perspective as a people leader and I bring it to my role as a leader to all my teams.

Contact Info:

• Website: https://www.inhouse.app/
• Instagram: https://www.instagram.com/curlysueandthebeetle/
• LinkedIn: https://www.linkedin.com/in/chadbillmyer/
• Youtube: https://www.youtube.com/@CurlySueandtheBeetle
• Other: https://www.trylrun.com/ https://www.curlysueandthebeetle.com