Why I overcommit to resolutions

We’re about nine weeks (!) into 2022. Studies show that 80% of people who make New Year’s resolutions will have given up on them by now. At first glance, it might look like I’m one of them. I made some ambitious goals, and I’m not on track to meet all of them. I don’t consider that failure. I used to, though. For most of my twenties, I gave up on my resolutions by Valentine’s Day💔. This was really discouraging. Every time I tried to improve myself, I ended up feeling like more of a failure. For a few years, I stopped trying altogether.

Then, when I was 25, I realized how unhappy I was. I didn’t feel professionally fulfilled or challenged, and it was affecting my confidence. I sat at a desk all day and needed something to get me out of the office and out of my head. So, I went for the classic office-worker physical challenge: the half marathon. I found a local trail race and signed up. I love hiking, so this seemed like a way to kill two birds with one stone: get back in shape and spend some time in nature. I figured once I had the date set—and the money down 💸—I would be motivated to train and stick with my goal.

Spoiler alert 🚨: That didn’t happen. I toed the starting line completely unprepared. Running 21 kilometers isn’t easy under any circumstances, but trail running requires even more strength, stability, and endurance to handle the terrain and altitude changes. I was in trouble and I knew it. I started the race with no expectations but simply with the goal to make it as far as I could. Throughout the race, everything that could go wrong did, and I finished as the organizers were loading up the vans. When I crossed the finish line, there technically wasn’t a line there anymore.

But, I did finish! Maybe it was grit. Maybe it was perseverance. Maybe I was just too stubborn to give up. Regardless, I felt amazing. I immediately signed up for another race—that’s how they get you! This time, it was a 70k race six months out.

“Okay,” I thought to myself. “I will definitely train for this one.”

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On paternity leave

TL;DR: I'm taking paternity leave for 6 weeks, and expect to be back at work by mid-December.

My wife and I are expecting our firstborn son in <2 weeks; though, in the words of our OBGYN, “only God knows when he’ll arrive“. We couldn’t be more excited about this new chapter in life and the many adventures that await us!

I always knew that I would like to take time off for the birth of my child. A couple of months ago, I began to give the duration of leave some serious thought.

You see, I’m a solo GP at a VC firm – the only founder of the org. And while I had planned to have a full-time employee by now, I’m still working on 27V all by myself. Don’t worry, I still love every second of it!

However, this does mean that when I take time off, all work stops. 27V is, effectively, paused. No deal flow conversations, no new investments, no portfolio support, no firm operations, nothing. And for me, that is scary as s***!

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Reflecting on 2 yrs of 27V!

It’s 27V’s birthday today! 🎂🎉🥂When I started raising my first fund in 2019, I couldn’t have predicted everything that has happened in these past two years (except for the continued success of Fiveable, Toggle & 101Edu — my first 3 investments — which seemed inevitable 🚀 even then). What I can say for sure is that my experience has taught me many lessons to apply to the next chapter of 27V — and confirmed a few I already knew, but needed to be reminded of 😜.

First, the lessons:

  1. Working as a solo GP does not mean working alone.
    I’m often asked why I’m a solo GP, especially given that everyone who knows me would characterize me as a people person. Day-to-day, though, I’m not alone: I’m collaborating with founders, investors, limited partners, and industry professionals. A special part of my job is to be constantly synthesizing insights from forty-five (45!) portfolio founders. Any GP can have ex-C-suite advisors with operational experience, but I get to build close relationships with entrepreneurs who are doing the work today and know what it means to build a company in this highly unique moment in time. Their feedback is invaluable, and I think they should have a say in the curation of the community we’re building together, which is why I ask the founders for feedback before making every investment — the #27Vfam rolls deep!
  2. Errors of commission > errors of omission.
    Part of being a GP is embracing the inevitability of missed deals. My responsibility is not to jump at every flashy new idea, but to make sure the ones I do invest in are financially sound and viable businesses in the long term. It’s cliche now but really, half the deals that get signed these days are based more on FOMO than actual potential. What I don’t want to do is invest in something where the math doesn’t make sense or that’s a reputational risk.
  3. Invest with conviction, at the right stage.
    Counter-intuitively, first-time fund managers (<$25M funds) are advised to invest a portion of their Fund Is in later stage companies to prove they have access to marketable names. That never sat right with me because I sincerely believe that I owe it to Fund I investors to generate meaningful returns for them rather than optimizing for the longevity of my business (the firm). Over time, I recognized that this advice (Seed funds investing at A or B) is even worse from a math perspective. A $25M fund investing $500K checks at $50M (or even $25M) valuations will never generate the net multiple return needed to justify LPs risking their capital. Which led me to the thesis of investing with conviction, because ownership numbers matter.
  4. Community is NOT a commodity, when built with intentionality.
    When I started 27V, I knew we were building something special with our portfolio companies, but I didn’t know how to explain it. What I did know is that I had a group of people — not just founders but their employees, too — connecting and helping each other with everything from investor lists to TikTok strategy (the Slack channel’s called #TikTank and I’m a regular lurker 👀). Most startup employees are moving into roles they’ve never held before. By opening up our Slack to all employees, we have the experienced engineering manager formerly from Twitch or Niantic giving advice to this young new manager in the midwest who has never worked at a big tech company. And, the knowledge flows both ways. I have four DTC companies using TikTok as their primary channel of growth. The #TikTank’s median age is under 25. They know how the target audience is using social media and are working together to figure out solutions for problems they all face. Teams can learn best practice from the people actually practicing, not investors who are out of the game. Building a community where the companies can help each other and are invested in each others’ success is collaboration at its best, where rising tides can lift all boats.
  5. Being a specialist investor with general knowledge IS value-add.
    Despite having a lot of relevant experience in investing, I had a bit of imposter syndrome during my first year as an investor. I didn’t know how to explain what I was bringing to the table. But, I learned that you can either be a general investor with a specialized value add (e.g., you invest in any sector and help them with deep product expertise), or you can do what I do and invest in a specific sector about which you are knowledgeable and passionate. In my case, that’s education and the future of work. As long as I can help in this specific space, whether I have a functional specialization or not doesn’t matter.

On to what I already knew.

  1. Relationships matter.
    This is not novel wisdom, but it’s true. My first LP came through because of a 6 year relationship. My first investments, Fiveable and Toggle, were from building relationships with the founders over months. I was a risk for these companies, but they chose to make space for me because we’d gotten to know each other. Of the 21 portfolio companies, more than half have come through referrals. Again, this is well-known in the investing space, and the tactical advice is just as enduring: be yourself and connect authentically. Investments are transactions, relationships are not.
  2. Location doesn’t matter.
    I’ve always been a remote investor. I live in Asia and deploy most of my capital to North America. While recruiting portfolio companies, many VCs limit themselves to their local regions or recognized tech hubs. They’re missing out! Game-changing innovation can come from anywhere. This location-agnostic approach was also a huge benefit in adapting to the pandemic. While most firms were spinning up new processes and getting comfortable on Zoom, 27V was already there. As innovation diffuses away from San Francisco and New York, I’m ready.
  3. Education and the Future of Work are the next horizon in investing.
    Investing in education and the future of work is why I wanted to start a fund in the first place. I’ve always been convinced that this space would have the most impact, and I wanted to build a firm to invest in those technologies. The pandemic threw into sharp relief just how imperative these sectors are, catalyzing rapid growth in invested $$$. It’s great for the ecosystem, and I’m not afraid of a little competition (just try to keep up 🏃‍♂️).

If the past two years have taught me anything, it’s that you can’t predict the future. The next year’s going to be even more special as it will bring on my biggest adventure yet with the birth of my first child. I’m sure becoming a father will change how I think about education, work, and everything else! But whether I’m supporting the Batra family or the #27Vfam, I’ll keep abiding by the same principles: showing up authentically, doing the math, rolling with the punches, and supporting the team as best as I can. Cheers to another two years 🍻, and more 🤞

I can’t tell you a single thing I learned in school. Here’s why that doesn’t matter…

As a VC who spends a lot of time and money investing in education, people are often surprised to learn that I didn’t really care much for what was being taught in class. I wasn’t a bad student. Teachers liked me, mostly because I was nice 😇 and followed the rules. My grades were decent, and I performed highly when I needed to (on standardized tests). But, my head was rarely in the classroom. This stayed true for the entirety of my academic career, elementary school through college. If pressed to tell you a single thing I learned in a classroom, I’d have a hard time answering.

This might not seem like an argument for education, but hear me out.

I wasn’t focused on school, not because learning wasn’t important to me, but because I was finding opportunities to build knowledge and skills elsewhere 🤯. I spent my days planning school events, participating in public speaking competitions and putting together theatre productions. While at university, I organized a conference for which more than a thousand students and teachers traveled to my home city to participate. I was managing inventories and accounts, coordinating logistics and programming, practicing my TED Talk voice, and more.

I was learning a lot! I just wasn’t at a desk while doing it.

This is called experiential learning, or learning by doing. Experiential learning occurs when learners take an active approach in the learning process, compared to the passive approach of listening to a lecture.

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Thoughts on Homeschooling

I recently had an investor friend ask for my opinion on Homeschooling. This is what I think – concerns and opportunities.

I recently had an investor friend of mine reach out to ask what my opinion on Homeschooling is, especially as it relates to investing in the many startups building products/solutions for the space.

Given the current situation that the world finds itself in – locked down, learning & working at home – there is definitely increased attention on the concept with many parents considering it a viable alternative to the uncertain future of in-person learning. I will add that this has been a growing trend for a while now; been reviewing relevant companies for more than a year now.

My concerns re. the homeschooling market are:

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