Tough Love

At the beginning of my junior year of high school my English teacher, Dorothy Palme, gave me a D minus on a paper I wrote. It was the first grade below a B I had received in my entire academic career. I was flabbergasted and livid. I stayed after class to ask her why she gave me the grade and she walked through all the reasons. What it boiled down to was that I was a poor writer. I left the classroom even angrier after getting the feedback. Like the little brat I was, I brought the paper home to my parents and exclaimed that I had been cheated. They read the paper and I'll never forget their reaction. They unanimously supported Mrs. Palme's assessment that I couldn't write worth a damn. They said so themselves and I knew they were a combination of disappointed and embarrassed.

Mrs. Palme was the best teacher I ever had. Over the course of the year, she worked with me to transform the way I approached writing. She taught me about introductory prepositional phrases, how and when to appropriately use adverbs, how to coherently structure my thoughts, and so much more. She did it all on her own time outside of class, too. Her lessons will stay with me forever and it's not hyperbolic to say that she changed my life for the better.

Most teachers would have played it safe. Perhaps they would have graded the paper a B minus or a C. But Mrs. Palme wanted to teach me a lesson - that I could and must do better. It was a lesson that required her to be brutally honest, and to roll up her sleeves and take the time to help me if I wanted to fix it. And while I hated the lesson in the moment, it fondly sticks with me to this day.

The Mrs. Palme's of the world are far and few between. Over the course of my professional career, I haven't encountered a lot of people who had the courage to tell me how it is. There are two investors and board members I've worked with that particularly stand out: David Weiden and Scott Feldman. David once lambasted me for not truly understanding basic concepts around unit economics like payback periods. And Scott once vehemently claimed that I was in the process of running my business into the ground because I was being a poor steward of capital. Both took the time to explain what they meant to me, connected me with people that could help, and also did the hard work of helping me themselves.

When it comes to investors, David and Scott are the exception to the rule. Most egregiously pander to entrepreneurs. For many, telling the brutally honest truth doesn't have any upside. Why rock the boat and develop a reputation with founders as being the mean investor, especially in the hyper-competitive market of the past decade? So much emphasis is placed on supporting entrepreneurs and being "founder friendly" that it's nearly impossible for most operators to get to the truth.*

The irony is that withholding the truth is the opposite of being founder friendly. There is a market for those who can do this exceptionally well. It's something I try to do when I invest in companies and work with founders. And to my delight, it's not just me who appreciates "real-talk." Entrepreneurs crave it. They may hate it in the moment because it can hurt the ego, but it resonates. When it comes to company building, I want to partner with someone who tells it how it is and isn't afraid to hurt my feelings than someone who prioritizes simply being liked. In my experience it's those that dish out the tough love that I've grown closest to and admire most.

*The counterpoint to this is that a majority of VCs are terrible at giving feedback, are bad at what they do, have zero compelling or relevant operational experience, and their hands-on involvement is oftentimes destructive. Choose your partners wisely or suffer the deleterious consequences.

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