Tech Trek Final Reflection

This trip was absolutely incredible… and we have plenty of pictures and a few pieces of swag to prove it. But as much as Apple or AirBnB’s offices were visually stunning, in my final blog post I’d like to reflect on the more intangible elements of entrepreneurship in the Valley–common traits of character and frames of mind that we kept encountering in the people we were so fortunate to meet. For me, there were three boilerplate common threads–although I’m definitely interested to hear other people’s impressions on character qualities of the types of people we met. 


The first and most fundamental character trait that was emphasized on the trip was the importance of persistence. CJ Reim and Peter Bell kicked of our trip with a focus on this quality. CJ did research on Peter’s companies as a student, and wound up annoying him enough times to land an internship (and a stay at his house…). We saw this theme echoed again in Riley, and his description of crafting 50 personalized cold emails to people and companies he was interested in when he was senior is simply next level hustling. Another one of Riley’s stories–his systematic research into the attendees of an event he was at, zeroing in on an employee at Visco, and then approaching him, leading to a new client for Campus Insights–it’s a scene out of a movie. Peter, like Riley, also exemplified persistence when he mentioned investing in a Princeton kid–and calling anyone he could find to learn about the character of this kid–including people in the dorm.


Grainy pic of Riley in action

Of course, another dimension of persistence concerns how one deals with failure. Amy Errett detailed her prior startups–one of which blew up. Yong Kim at Wonolo touched on his struggles in immigrating to the United States. Persistence is also demanded at the company level–we saw Brava and Omni struggling to define themselves–and there’s a good chance they might run out of time.

However, the problem with persistence is that most times there seems to be an overwhelming gap between where the people we meet are and where we feel we are. That’s where I think the second idea that kept resurfacing throughout our week–intent–fits in. Change does not happen instantaneously–and in persisting, one needs to keep in mind what he or she is persisting for in the first place. One of my favorite quotes on the trip came from the CEO of Instawork: “Inches off at Launch, Miles off in Orbit.” Not only does one have to be persistent and diligent, but there needs to be a focus on what one is doing now in the day to day, and how its contributing to whatever one chooses their goals to be.

And as Sophie Miller advised us, one needs to articulate clear goals–telling people what you are looking for. And it’s not that all the alums who were killing it out there had smooth paths–Mike Perry was rejected from Twitter the first time around, several young alums at the Rainforest startup panel left Oracle–but I think many of them, in persisting and exploring different options, were hyper-focused on what they were hoping to achieve, what skills they were hoping to acquire–in short, why they were doing something in the first place. This is the heart of what it means to be intentional. It seems kind of obvious, having a reason for why, but I know from my personal experience sometimes its very easy to go through the motions in doing something–maybe without even realizing it. Trying to be more intentful was one of the biggest personal takeaways from this trip for me.

Finally, I think the value of trust ties together the themes of persistence and intent. Beyond being a core value at some of the companies on the Trek, such as Instawork, one has to trust that their persistence and focus on having intent in planning will prove rewarding–even if no readily available metrics of improvement or progress are available. As we heard at Wonolo, there’s no textbook out there for building Wonolo, and at some point, one has to take all their persistence and intent and take that leap into the unknown. Sometimes, we saw, companies fail, or have to pivot–and it is ridiculously difficult for founders and even investors to keep believing that they are not just banging their head against the wall. Balancing taking chances while not being delusional–that’s a real challenge. But that’s also entrepreneurship–and at a core level we have to cultivate some form of a trust that a better  product, service, or something in between can be built.

In closing, I’m incredibly grateful for this trip. Thankful to the professors, kelsey, and everyone in the class for making the week so enjoyable. Hopefully at some point BC kids will be visiting people on our class on a future Tech Trek. In the end I felt that this week, beyond meeting alums and touring companies, became about how to acquire an entrepreneurial mindset–and some of the character traits I highlighted were the ones that most stood out to me and I most hope to improve in.


Bad lighting here, but walking in Palo Alto a couple of us found this plaque for the original “The FaceBook” office


Cooking with Brava

4 thoughts on “Tech Trek Final Reflection

  1. Great post Charlie. I really liked your ideas of establishing clear goals and the value of trust! Great to get to know you on the trip, even though we were not able to see the Golden Gate on our hike ://


  2. I really love that you touched on how entrepreneurs deal with failure. Larger company culture typically works to avoid failure; where it is viewed as a natural step in startups. It’s no coincidence Amy Errett said that a great operator needs to be resilient!


  3. Hey Charlie! I was also super impressed by CJ’s and Riley’s persistence and hustle. Like who would be borderline-stalkerish to plan to “accidentally” bump into the person like with Riley’s story? It’s this kind of mindset and drive that really distinguishes them from other people which really shows in what they do as well as how they present themselves. Definitely some good role models to look up to for career advice!


  4. Charlie, my man. Great post. I enjoyed reading your perspectives on the trip. I particularly enjoyed the quotes from the InstaWork CEO and the idea re: starting a company from the Wonolo CEO. These are two things that I had errored in not jotting down, but glad you reminded me of them. I had a great time getting to know you through the week– our adventures created some lasting memories.

    Liked by 1 person

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