Exactly a year ago today, I posted about taking time off of Duke to join a startup in MV. Since then, I left to run Glimpse full-time after receiving funding from Y Combinator and joining the W20 batch.

My original article has resurfaced due to COVID, leading to more than 2 calls a day with students questioning higher academia. While I love calling and discussing if dropping out of school makes sense for you, I hope answers to the most common questions will help you decide on your next steps.

The 6 Most Common Questions I Receive

“How did you know your idea was good enough to drop out?”

I remember a formative conversation at Philz Coffee in Palo Alto.

I was asking for advice regarding long-term implications of my decision to leave college, and the designer I was with, unbeknownst to me, used the 5 Why’s technique to make me critically think about my decision in a structured way. Only after our coffee did I realize how clever that was. It went a bit like this:

• Why are you joining Smartcar?
  Because of the amazing opportunity, team, and ownership
• Why do you care about finding an amazing team and having ownership?
  I want to learn what good leadership looks like, wear as many hats as possible, and accelerate my learning
• Why do you care about accelerating your learning?
  Learning is the single most important way for me to self-improve
• Why do you want to self-improve?
  I want to make an impact on the world and need as many soft+hard skills to make that happen
• etc.

In the moment, the decision to do something different from what everyone has been priming me for, was terrifying. When I took a step back, it turned out to be innocuous, low risk, and even obvious.

YES — I said dropping out of school was low risk. Call me crazy, but I believed not leaving school was a larger risk. My option to return to school was always on the table. My option to leave felt ephemeral.

And then I got into Y Combinator. That removed any doubt that leaving college was the best decision I’ve made.

YC was a dream of mine since early high school. YC is glorified through Airbnb and Instacart, and, despite overly hyped, I have to say I loved my experience.

It’s amazing for first-time entrepreneurs, for endless energy, and for building your network. Even better if you are selling to other startups in your batch and B2B SaaS. Maybe not something to do twice (or virtually), but worth experiencing 100% — even as a social consumer company.

In school you are safe and protected. You have time to explore and learn. You explore in sandboxes and learn models. When building a startup, you learn that all models are wrong, while some are useful. You learn the power of telling a story. You learn how to excite people about what you are working on.

If you feel this sense of urgency to act now, ask yourself:

• what exactly made it feel like a fleeting opportunity?
• where does your impatience come from?
• why do you care so much?

“How did you know you had all the required skills?”

What gets me about this questions is that it assumes one is able to acquire all the required skills without doing it. For the same reason you won’t learn to cook by reading a cookbook.

Eventually everyone finds out that
(1) their parents are people too
(2) teachers go to grocery stores
(3) even real life software engineers, don’t know what they’re doing

These three realizations should not only remove any sense of Imposter Syndrome, but it is also to register that nobody knows what they are doing. Parents are winging it, as is a newly hired software engineer.

There’s an increasing demand in college preparing you for the real world. The irony is, no technical skill will prepare you for the real world. Universities have existed for so long exactly because they don’t focus on any technical skills, rather on building your work ethic, ability to learn quickly, and problem solving skills.

If you are choosing to go to college, don’t treat it as a way to prep for a job. I cannot stress this enough. ie: computer science degree != SWE.

An infamous 10,000 hour rule declares that to be an expert, you have to do something for 10,000 hours. While it has been disproven, some truth to this exists! The sooner you spend all of your energy on one thing, the sooner you will acquire many of the skills that line you up for success.

If you feel lacking of required skills, ask yourself:

• will you ever have the required skills?
• what are ways to fill gaps in skills you find yourself needing?
• what are your reservations about learning skills on the job?

“How did you get started?”

Just do it.

We “just do” all the time. You’ll find that there’s two types of people: the talkers and doers. Surround yourself by doers and you’ll find you cannot resist from picking up that trait.

We surrounded ourselves with other highly motivated Y Combinator founders by living in a house together in the Mission, SF. Brian and I would find ourselves coding on Caltrain heading to a Y Combinator dinner, debugging in parking lots charging our electric car, awake at 4am reaching our sprint goals, and recharging on the floor at my parents’ house (in pic below).

We regularly paused for passionate conversations about building authentic relationships, being vulnerable, etc., and held ourselves in check that everything we were building was making others feel genuinely more together.

Identify what vision you have, and work backwards to reach it. This will definitely involve a lot of learning, but what’s amazing about 2020 is that we have the internet.

If you feel lost where to start, ask:

• what’s your vision?
• what’s stopping you?
• how badly do you want this?
• how do you test if this is a good idea?

“I heard you built an MVP in just a week? what??”

What a fun story!! A minimum viable product (MVP) is the first beta worth getting feedback on.

We decided to pivot 2 weeks before Y Combinator’s demo day. Imagine prepping for 3 months to pitch to a room of VCs, and then starting what feels like ground zero moments before.

Glimpse came out of our previous in-person-meetup platform (just imagine how a 1:1 IRL platform would look right now). Any MVP can be stripped down to fit whatever timeframe you decide.

Our MVP was stripped down such that it could be built in a week, to give us a week to validate and grow our user base.

Three large components to our MVPs:

(1) Insights, Hypothesis, Idea

A huge part of building an MVP is gaining insights, creating hypothesis, etc. — we had a bulk of that: we went into building Glimpse with a lot of knowledge from our previous attempt to build authenticity.

One being — we learned a driving force in creating offline relationships, was surpassing the activation energy needed to meet up. Scarcity, or in our case, time-boxed conversations, got people jazzed.

(2) Actually Building

We had an advantage here too. We’d been building social apps for a while. We had internal frameworks that allowed us to whip up new skins for similarly structured backends. Infra + db logic was all already done.

This is where the scoping down of an MVP really matters. Understand what resources your team has and factor that in carefully.

We spent a week working remotely from Lake Tahoe, treating it as a weeklong hackathon.

(3) Validation

There’s limited value in building quickly if you cannot test quickly! After getting feedback from our closer circle, we chose product hunt, and were featured in their newsletter, helping us out tremendously.

“How do I find a cofounder?”

This is likely the hardest question to answer because it takes time. You want to work with someone you will trust, respect, love — and to discover that takes vulnerability, intentionality, and time. You are entering a marriage.

Work on side projects. Explore your existing network. Join slack groups?

I feel extremely lucky! Working with Brian is one of the best dynamics I’ve had. We balance each other well with very different personalities and strengths, yet share values and passions. We met beginning of our freshmen year at Duke and worked on Duke’s Conservation Tech hackathon together. We got close through Catalyst, and hacked together at PennApps.

“How did you make it work financially?”

The financial risk alone prevents many from taking the leap of faith, leaving school, and pursuing their startup full time. You won’t be able to dedicate your time to a startup if making ends meet financially is a struggle. Tackling this requires both saving money and getting capital.

Saving Money

• cook! buying raw ingredients and throwing them on a pan is far cheaper (and healthier) than ready made meals or takeout
• startup plans! Free tiers are quite generous. Learn to never pay full price. AWS, Segment, Asana, Sendgrid, Twilio, Fullstory, Mixpanel, etc. They have generous startup plans that have allowed us to operate with almost no expenses.
• work and live together :)

Getting Capital

(this is a massive topic and this is a super high level overview)

• For us it was YC! They wire you 150k to do with whatever is necessary to set you up for success. I know people who pay their college debts with it, others pay rent, and others take a salary.
• Incubators/Accelerators: similar to YC, other incubators give you capital to build along with intense mentorship and a founders community. Techstars, 500 Startups, PlugNPlay, and many more exist around the world.
• Student entrepreneurship programs. Many colleges encourage entrepreneurship and may either support you financially, or treat your work as a credit towards graduation. If you are an international student or on financial aid, this is a fantastic alternative to dropping out. At Duke, the Melissa and Doug Entrepreneurs program would have been my go-to.
• Student VC funds. Dorm Room Fund, Rough Draft Ventures, Contrary Capital, etc., focus on investing in college students.
• The Thiel Fellowship pays you to drop out!
• Angels / VCs. After YC, we did raise more from Angels and VCs. Going through YC helped with growing our network and understanding how to approach those conversations
• Kickstarter. Many successful companies start with initial kickstarter money. If you’re in D2C and need capital to build a physical product, this could be perfect.

so… should you drop out?

Remember the Squeeze Theorem back from AP Calc (🤓): the upper and lower bounds both meet at “this decision does not mater.” It’s an inconsequential decision: if you succeed, dropping out does not matter. If you fail, also doesn’t matter — you can return to school*. Worst case, you have an amazing story and lessons learned.

Back in Spring 2019, I believed that structured higher academia was overdue for a revamp. This pandemic is making others realize the same thing with school being virtual or, at a minimum, implementing covid precautions. Fall 2020, while enrolled in Zoom University, is looking quite disappointing.

Keep in mind my answers to the questions above are pre-covid answers. Every push to leave school is now 10X of what it previously was. Any future employer will understand an odd career path, and, if you’re in good standing with your school, returning* is a breeze.

tldr:
If you’re obsessed with what you’re working on, find a way to just do it.

• disclaimer: every school has a different policy on how course credits and financial aid are treated if you take time off — check with your Dean!

a note to higher education:

To the people designing leave of absence policies — forcing students to stay enrolled by threatening their financial aid, or limiting early graduation, is unnecessarily controlling and favoring those from a privileged background. The decisions I’ve made would have been far more difficult if I came from a different socioeconomic or racial background. Universities have the ability to address a lot of that!

Imagine a world where you’d be encouraged to take time off and explore your venture, where your school did not banish you from campus when you left, and continued to be your support system. Stanford has one of the best leave of absence programs I’ve seen — and last I checked they are a pretty descent university.

For international students interested in entrepreneurship, leaving risks receiving an H1B and they have their hands tied. Can you set up an independent study-eque system where they are technically enrolled and receiving a degree?

Higher academia needs to adapt quickly or go extinct in this burst of educational evolution.

Someone once told me: not everyone can take the risks you do, so you owe it to others, to take all the risks you are able. That sucks. If you love what you do, are giving it all you possibly can, you should be able to. Unfortunately it’s not the reality. Addressing this, is the Thiel Fellowship’s vision! Similar programs are being launched for good reason.

I recently had a conversation with the founder of Future Minds Network. He believes school should be preparing us for the future of work. Starting ventures is an amazing way to gain leadership qualities, critical thinking skills, and more.

COVID is a catalyzing force in driving the evolution of education. COVID is finally making people question what they’ve taken at face value!

A large question remains.
Universities come with prestige, status, a network. With this moving online, a lot of that falls apart. A large question remains: how do you replace the “eliteness” that comes with a top university with an online one?

Is the new status symbol — are you on clubhouse?