CollegeVine HQ is where our team of 50-and-counting is building the guidance office of the future. We used to be based in Cambridge, MA but have since gone fully remote.

2022

This year, I stepped into the Interim COO role to help us scale into our full business opportunity.

2022 has been an interesting year. The start of the year is what we now know to be the dying days of our generation’s bull market. In May, all startups were advised to prepare for 18-36 months of nuclear winter and to focus solely on fundamentals. As 2022 draws to a close, CollegeVine did just that, yet finds itself accelerating into hypergrowth in 2023 due to the market’s pull.

So I find myself in the midst of a unique time and energy that may never come around again. I don’t know what self-actualization is supposed to feel like, but this might be it for me. The trick is to not think so hard so that you wake yourself up from the dream :)

Resources

If you want to learn more about CollegeVine, I’d recommend checking out our website.

If you want to learn more about me at CollegeVine, my LinkedIn is a good place to start. My bio links to a piece of writing that was originally intended as a scaling tool, but which turned out to be better as an advertisement for our organization to potential candidates: Working with Mohan.

Organization Building

So much can go wrong between the 25 to 100-employee ramp that I consider it make-or-break for a promising startup. Sure, if the market pull is strong enough, you’ll “succeed” whether you were intentional about it or not, but man—just the amount of unnecessary suffering when it’s done poorly!

I didn’t expect this of myself, but it turns out that I am a Series B animal. In fact, I’ve come to realize that I’m better as an advisor than an operator in the early stages. But when the systems get more complex, sniffing out where the leverage is and managing the change through a growing organization plays perfectly to my strengths. So 25 to Dunbar’s number is when I’m most in the zone.

I’ve been an IC (individual contributor) in a painful ramp and I’ve been a newbie executive in another—both tremendously valuable experiences. However, this time, on the third go-round, the game feels much slower to me and I’m actually having fun and able to exercise a lot of spontaneous creativity as a result. I’d love to trade notes!

Advising

Before I was COO at CollegeVine, I was CTO for 6 years (and will probably return to the role once I’m out of my depth as COO).

I’ve recently been talking to engineering leaders at startups that are in an earlier stage than CollegeVine and have found great joy in helping them transform their engineering teams by teaching important concepts and principles that I’ve learned over the years.

I didn’t realize it at the time, but the intuition for why I’ve captured and distilled the right framework and principles is that CollegeVine essentially allowed me to do the closest thing possible to a controlled experiment on culture: we built the business one way through 2019, decided we didn’t like that business model, pivoted and downsized, I did a bunch of thinking about engineering’s role in all that, and did it all over again with another business model and culture with the same core group of people.

So the people didn’t change, but the results were drastically different this time around. That’s probably as close to an A/B test on culture as you’ll get in this line of work.

But don’t take it from me. Here’s what a grateful advisee had to say:

“Just wanted to say thanks again for all the advice man. We’ve talked to many CTOs at various stages but you are the one who [our lead engineer] and [engineering manager] consistently want to hear more from.” — a founder/CTO

Due to these positive experiences, I’ve vowed to always take a call from any budding engineering leader who wants help. Think of it as my way to pay it forward for all the good mentorship I’ve gotten over the years.

2015

I co-founded Canopy Education Inc. in 2015 with my cofounders Zack, Johan, and Vinay with a mission to become the trusted source of lifelong guidance for the next generation.

As our story is not fully written yet, I feel like there’s no point waxing poetic about the nature of the rollercoaster ride, though there’s no doubt we’ve had seven colorful years thus far.

We’ll tell the full story someday when the time is right, but for now, we’re focused on what the present brings and what the future holds.