In this solo mini‑lesson, Joshua Fraser recounts his 2017 Techstars Boulder experience where he pitched a six‑minute presentation before a 1,300‑person audience and met with over 100 venture capitalists. He explains how he deliberately chose Foundry Group’s Jason Mendelsohn and Brad Feld as mentors, and shares two core lessons they gave him. The first lesson is the mantra “brutal honesty delivered kindly,” which he describes as a continuous practice for founders: being completely truthful while framing feedback respectfully so employees and colleagues receive it constructively. The second lesson is an analogy that VC funds operate like ten‑year marriages; before a fund writes a check, the founders are essentially entering a long‑term partnership. Fraser uses these stories to illustrate how transparent communication and an understanding of the fund’s timeline can improve founder‑investor relationships and guide everyday entrepreneurial behavior.
Chapters
Foreign. Honesty delivered kindly. At some point in my life, I'm probably gonna get this tattooed on my body, I swear to God. I'm just gonna tell you the quick story of how this came to be. As stated, we went through Tech Stars in Boulder in 2017. At the end of Tech Stars, you go in front of an audience of 1300 people and you have a six minute pitch. I'm going to share that in YouTube in the links below. Here you can see me nervous, pit stained, sweaty and freaking out, pitching in front of 1300 people for the first time in my life. But that morning we pitched 100 VCs and I already picked out the VCs that I wanted to work with. Jason Mendelsohn and Bradfeld, they're part of Foundry Group. They're a tier one venture capital firm globally. They do a lot of B and C rounds, but I knew that these were the guys I wanted to work with, learn from. And Jason Mendelsohn, one of the first pieces of advice that he gave me when we were sitting down at dinner, there were two actually, but brutal honesty delivered kindly. You need to Often as entrepreneurs we're moving so quickly, we're in the fast lane, we forget to deliver information kindly. I'm still a work in progress. I'm sure you are too. But you just have to constantly remind yourself that you always want to be brutally honest. You have to be respectful, you have to have constructive criticism. But if you can deliver that kindly, your employees are going to appreciate you so much more. And this is a line that I repeat to my friends, my family, my employees today. And I'm just constantly repeating it. So I figured this was a really good lesson to share with you guys. And I dive into the entire story with Foundry Group. The second lesson that he taught me that you may or may not know when venture capital fund invests in your business. They typically on a fund are a 10 year lifespan. And we're sitting down at dinner with Brad Feld and Jason Mendelsohn and they ask us if we're going to invest in you guys. Like do you know how long the average US marriage is? I'm a 26, 27 year old kid. I'm like no, I have no freaking idea. I'm Canadian too. And they're like, it's seven years, 7.5 years or something. Our fund is a 10 year fund. So technically before we write you a check, we're going to have to marry you. And that was like very direct. Brutal honesty delivered kindly in a way and Jason would always. I always thought he was brutally honest. It wasn't always delivered kindly, but I knew that even him, at his level of success, like he's a billionaire, was always still working on this. And so that's something I find myself telling entrepreneurs over and over and over again. So that's number four.
