rejection

I’ve spent a fair amount of my life as a young person facing rejection. As a child getting cut from sports teams, as a teen not making it into elite colleges, and as a young adult facing brutal internship/job passes, I am no stranger to the painful ache that rejection causes. I have a deep understanding of some of the long-standing effects tough rejections can have, and it’s hard not to recall times when I showed up at my best and met with what I deemed to be the “worst.”

The complex and burdensome emotions that rejection can illicit are something that I spur in founders every day. I spend a large portion of my time as an investor rejecting founders, and being so familiar with the feelings myself, it is a dichotomy I’m learning to be comfortable with. I sit across the table from founders each day who have put EVERYTHING into their businesses, and 99% I follow up with an email on my firm passing on investment.

There are a few reasons in particular why I wanted to write about rejection as my first “soapbox.” #1 I want founders to know that no matter how quickly calls go — I can feel the emotion, time, energy, and capital that they have put into their business and that even though I say no often, I don’t say it lightly. #2 VCs themselves are a business, and that’s not talked about enough. We care about founders, and we deeply want them to succeed, but ultimately, our duty is to our investors called LP’s whom we seek to drive returns for (more on this in the future).

No’s are said for a variety of reasons, and most of the time, No’s can be traced back to more arbitrary reasons and things that founders can’t control, such as portfolio construction, biases towards certain industries/verticals, conviction/market trends, other deal flow in the pipeline, etc. Each “No” is rooted in a complex and sometimes uncontrollable combination of events and circumstances, but that doesn’t make them hurt any less.

I’ve thought a lot about how I can be more comfortable dishing out multiple rejections on a daily basis. I’ve found that transparency drives clear expectations, and intentionality helps reason with difficult emotions. I’ve learned to start each intro call by sharing a clear background on Redbud; I leave time for founders to ask me any questions they may have about our process; if there is a perceived conflict of interest, I mention it immediately. My favorite question I’ve started asking is for founders to share thier favorite articles, white papers, or case studies with me. It has allowed me to do a quick dive into their industry, gather my thoughts, and communicate them to my GP clearly. Information drives reasoning. In the midst of my most poignant rejections, I’ve always asked myself, “why?”. Now, I deliver the clearest and most concise ”why” I can to founders in each rejection post intro or second call.

Ultimately, rejection is an inherent part of raising capital, and while it may never be easy, my goal is to handle it with respect and empathy. I’m striving to create a culture where the pain of rejection isn’t lessened, but the clarity behind it is increased. I’m starting to view rejection as an opportunity for evolution — both for myself and the entrepreneurs I interact with. It’s a chance to mutually refine our approaches, learn from setbacks, and foster resilience. Something that not many other events/emotions have the opportunity to illicit.