Steve Kupfer, Venture Partner at Reach Capital


Steve Kupfer: Trusted Caddie to Founders and Our Newest Venture Partner

Growing up, Steve Kupfer caddied at the local golf course. Years of lugging clubs for others offered up-close lessons in understanding people and how they approach opportunities and adversity. How they react to tough breaks and lucky bounces. Who’s chatty and who wants to be left alone. How to read shifting winds and subtle cues.

And of course, what guidance they need to get the ball in the hole.

Those skills learned on the course have been core to Steve’s career as a trusted mentor, advisor and investor to edtech founders over the years. He describes investing first and foremost as a customer service job — and that value is just one of many reasons we’re excited to welcome him as our newest Venture Partner.

Our relationship with Steve goes back to 2011 when we co-invested in Goalbook together. Since then we’ve co-invested many times, most recently in Rhithm, whose CEO and Co-founder Josh Knutson said: 

Steve is a rare blend of both analytical and emotional intelligence. He is a SaaS metric guru and caring mentor. He has a unique capacity to deliver a prescient analysis of broad market trends, rich with quantitative detail, in the same way a good friend would discuss their afternoon plans — casual and relatable. He is equal parts personable and brilliant and I’m blessed to have had him along for my journey as a founder

It was clear from working with Steve over the last decade that we were values-aligned in our approach to investing and supporting founders. When it was time to grow the investment team, the decision to recruit Steve was an easy one as he always topped our list.

After graduating from college, Steve’s first job involved building and deploying special education management (IEP) software for districts in Minneapolis and Philadelphia. The “formative moment” of his career, in his words, came in the wake of Hurricane Katrina, when the Recovery School District asked for help to stand up a special education technology platform after the flood washed paperwork away. Then 26 at the time, he was the first on his team to sign up for the job.

Over the next year and a half, based out of the central office adjacent to the Lower Ninth Ward, Steve worked alongside teachers and administrators to implement the first digital special education platform there. “After spending almost two years in New Orleans immersed in the trauma of rebuilding a devastated community of schools, it was clear there was no other mission for me to pursue” than education, he says.

To better understand the sociopolitical dynamics that informed how districts were organized and operated, Steve next worked in executive search and development for superintendents. He recruited and trained hundreds in critical areas including board governance, collective bargaining, political mapping, media relations and community engagement. Over 170 of them have been appointed to a superintendency.

Through this work, he saw a growing dissonance between where capital in education was going, and the urgent problems he saw on the ground. In 2013, he started Red House Education to help entrepreneurs who were tackling big, tangible problems and has since invested in 26 companies, including Ellevation, Paper and TeachFX. He’s helped many founders build successful businesses that have made enormous impact on the mission and financial fronts.

Steve brings a rare combination of deep industry expertise, great instincts in sizing up investment opportunities, operational know-how, a willingness to work side-by-side with founders through vexing business challenges, and an EQ that engenders deep trust from everyone he works with.

We could not be more delighted to welcome Steve to the team! If you’d like to connect with him, reach out at steve[at]