When I returned from San Francisco back in September, I was honestly a little lost. I knew I wanted to build something, as many people do, but as all entrepreneurs know, the road is rough and lonely. Most of my good friends had full-time jobs, or were actively looking, whereas I was thinking of which problem space interested me and how I would go about building a business to address it. This wasn’t a more ‘noble’ or ‘purposeful’ path, but simply the one I felt was the best fit for me.

Trying to build something is not a fun headspace to be in, but one thing changed that — joining Dorm Room Fund (DRF). Since coming onto the team in November, I’ve been surrounded by highly motivated people, many of whom are trying to build their own business. In this post, I’ll dive into my experience with the organization thus far, my experience at our annual retreat (All DRF), and how that all fits into ‘community’.

What is DRF?

In 2013, Josh Kopelman and the team at First Round Capital (FRC) decided to make a bet. They saw that some of the hottest tech companies were being started by college founders, many of whom dropped out to build their business. This didn’t have to be the case; college is an incredible time in your life, whether that’s undergrad, MBA, or a different stage. The access to professors, resources, and like-minded students should incubate the greatest ideas. FRC wanted to improve the experience of building in school by funding student founders with a $20,000 pre-seed cheque.

The DRF team is essentially split into two parts — investment and operations. The former consists of ‘investment partners’ in each of our investment cities (Boston, NYC, Philadelphia, and San Francisco) that attend school in that area. They source deals from surrounding schools and make decisions on whether DRF should invest. The latter, operations, consists of partners that support DRF in a specific capacity, as well as DRF portfolio companies. I joined this team to help with marketing alongside my co-lead, Phillip, however there are other roles for engineering and design.

It was rewarding getting to share my marketing / growth ideas with our portfolio companies, and see them implement that into their planning. It has also been a blast getting to run DRF’s brand via social media, blog posts, and other cool initiatives in the pipeline. However, that’s not the point of this post; the best part about DRF has by far been the community.

‘The G.O.A.T.’

Ever since Tom Brady staged an incredible comeback to win the Super Bowl, the term GOAT (Greatest of All Time) has been thrown around in increasing frequency. It spilled into non-sports related conversation in reference to other incredible people, i.e. ‘That movie was amazing, DiCaprio is the GOAT’, and later spread to products and inanimate objects: ‘I’ve never felt so organized, Notion is the GOAT’, finally culminating in daily use for simply accomplishing a task (see below):

How does this relate to DRF? Well, as cocky as it might sound, I strive to be the GOAT. I want to be the top in my field, have drive and grit that pushes me beyond the crowd, and inspire others to do the same. At the same time, I’m human — I’m prone to sleeping in, being comfortable in complicity and/or mediocrity, and being risk averse.

Community is a big indicator of success and potential. I prefer to call it ‘tribe’; the people you heavily associate with, who project and reinforce your value system, challenging you to strive for new heights. I try to surround myself with people who are at the top of their game, but this is rarely in a contrarian sense. Top = coveted job that everyone is striving for. This unfortunately creates a culture based on achievement; people who obtain these jobs have ‘made it’, and it becomes difficult to break the chain and continue to challenge yourself. I’ve seen this become an issue for people in their mid-20s, who face existential crises on whether they’re pursuing a career based on their values, opposed to one that validates their value choices.

Enter the DRF community: partners that hail from Ivy League schools and coveted MBA programs, all of whom were already at their top of their game when joining the DRF family. In just (6) years of existence, past DRF partners have gone on to become partners at top VC firms, start and run companies worth $100M+, participate (and graduate from) Y Combinator, and, as many high-caliber people do, work at those highly coveted jobs in tech, finance, and other fields. The difference, which I’ll dive into later in this post, is that they possess the drive to relentlessly pursue experiences (job-related and not) that get them one step closer to self-actualization.

3 Takeaways from All DRF 2019

Last weekend, I had the pleasure of attending DRF’s annual retreat, All DRF, that brought together 70+ current partners, alumni, and allies of the program for programming, updates, and team bonding. This was my first exposure to the full team and alumni in-person, and for an extended period of time, hence it’s the focus for this post. Below are some key takeaways I got from the weekend, which I think are universally applicable to any community / tribe.

(1) Support & Challenge

This past year, I witnessed a number of friends get new jobs and make big life decisions. In the process, they were supported by close friends who helped them prep, and made introductions for them that would increase their chances. This is typical of any strong community, built on a backbone of support. If these jobs were conventionally attractive (i.e. high-paying), or life decisions that were expected (i.e. moving for high-paying job), a pat on the back was automatically extended.

DRF is similar, in the continual openness and support offered by the community. The difference is that, in my experience, a ‘pat on the back’ is never automatically extended. You got a great job, kudos, but why are you taking it? It felt natural to get that outcome; what would be unnatural AND give you the same sense of gratification? Challenging your closest friends and urging them to share their thought process is crucial to building a strong and hungry tribe. It avoids confirmation bias and increases the probability that you’re pursuing the path of greatest return, not the one of least resistance.

(2) Search for diverse perspectives

I’m a marketer, which means my views are largely shaped from a ‘business’ lens. Most of my good friends are in business-related roles, i.e. finance, sales, etc. The majority of them also received a business education. This creates a homogenous worldview, despite efforts to diversify. Building on the previous point, a homogenous group can only challenge themselves to a certain extent; it is impossible for them to ask questions or approach problems in a way that is alien to their foundation.

DRF is bonded by a love for tech, a knack for building, and an interest in venture capital. This brings together a smorgasbord of people — engineers, researchers, MBAs, and more. Some partners are freshman in college, others are 10+ years into their career with multiple degrees. This range of perspectives means I can have the exact same conversation with a couple different people, and each goes in a very different direction.

Example: Over the weekend, I asked a few people how they reconcile their values with their work. I’ve tried this in the past with other circles, and it was usually met with ‘that’s a good question!’ or ‘I’m still trying to figure that out’ — the former forgotten a few minutes later and the latter met with no plan of action. At All DRF, this was rarely the case; in fact, I’ll list a few (summarized) views below:

Person #1 — Believes that you can reconcile your career with your value system, and pursue a career that fulfils it. I.e. social impact investing for someone that wants to make a difference. Reasoning: had an earlier near-death experience and seeks something more from life (work and personal).
Person #2 — Believes you don’t have to reconcile career with value system. Work is a natural motion and trying to find value in everything leads to misery. Reasoning: runs their own startup, is possibly already fulfilled to a certain threshold?
Person #3 — Believes that value system and career are mutually exclusive. Being challenged in work does not (always) mean being challenged in values, should aim to realize that through personal relationships and pursuits. Reasoning: wants to be a chef but works in tech, hard to aim for a convergence of the two paths.

This is just one, specific example, but there are many more that happened throughout the weekend. I.e. talking about starting a company yielded different results — one did it while in school, another dropped out, and another left a highly coveted job (Google APM) to pursue it. Tl; dr is that intentionally surrounding yourself with diverse perspectives gives you more to compare against when introspecting, and (in my opinion) gives you an enriched worldview. Can’t find these perspectives? Force yourself into situations (and communities) that will provide them.

(3) Never stop having fun

All this talk about career planning, optimizing for learning, and other cliches bring one thing to mind: hustle porn. The LinkedIn and Instagram ‘influencers’ that talk about ‘never stop grinding’, that laugh at the idea of work-life balance and idolize an unrelenting hunger for productivity. I hate this; it’s toxic, suppresses vulnerability, and makes you feel less valuable if ‘grinding’ is not your #1 priority.

At All DRF, after the workshops on venture investing and recapping DRF initiatives, we had fun. Everyone, regardless of age and stage of life, enjoyed decompressing through bowling, basketball, and even flip cup. I loved this part about All DRF, and to know my community values this balance, as it reinforces the notion that your career — synonymous with ‘hustling’ and ‘grinding’ — is only one part of your life. Personal relationships, hobbies, and, to put it bluntly, things that make you happy, comprise the rest. I believe that any successful community, and one I’d want to be a part of, should promote having fun and building relationships (note I said relationships, not connections or a network) as a core tenet of their membership.

Conclusion

Like many of the recent developments in my life, DRF was not ‘part of the plan’. Last summer, in San Francisco, I went to a NavTalent speaker event that my friend invited me to. In the pizza / drinks part of the evening, I met an Asian dude with impeccable style who was a design intern at a tech startup. After grabbing beers a few days later, he mentioned that a group he was a part of (DRF) was hiring for a new marketing partner. A few months later, after applying and interviewing, I joined the family.

I can’t thank DRF enough for taking a chance on me and welcoming me into their family. As with many other communities, it’s what you make of it — and I hope I can maximize my contribution in the time I have left. If you’re looking to improve student entrepreneurship on your campus, or if you’re a student starting a venture and looking for funding, drop me a note at trevor@dormroomfund.com :)