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.”
Continue reading “Why I overcommit to resolutions”
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***!
Continue reading “On paternity leave”
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:
- 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!
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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 🤞
last updated: 30 April 2021
this guide is republished from an internal document that was hitherto visible only to 27V team members and portfolio founders.
Run to keep sane
Always curious, always learning
True measure of success is how helpful one is and one’s relationships
- I work from home, on my own flexible time 🤷♂️
- On my desk 7am-8pm HKT most days; other than a long-ish lunch break when I relax by watching TV 📺 or drumming 🥁
- Over-communicate! I find working remotely can be quite isolating so I tend to email/message/talk to people a lot.
- I believe asking tons of questions ❓ is the mark of someone who’s actively learning, so ask away.
- Quick acknowledgement (even a simple emoji 👍) goes a long way with me.
- Prefer not to use IM apps for work, to the exclusion of Slack #️⃣.
- The reason Slack makes the cut is that it enables siloed work conversations. Never use WhatsApp or Messenger for work conversations – they’re reserved for personal uses. (ofc if you’re a portfolio founder, you do have my phone number and are welcome to call me any time!)
- For all comms with people outside the team (which is 27V + Portfolio), I use email. I’m very responsive on email 📥, try me.
- I’m a power user of Calendly 📆 and have different links for differently meeting lengths; 95% probability I’ll send you one to schedule a meeting. However, if you don’t find a suitable time, lmk and we’ll play calendar jenga over email.
- For better or worse, I spend a lot of time on Zoom calls. Default to audio – it’s very draining being on video 5+hrs every single day 📹.
- I like to have an agenda for every call – if I haven’t sent it in advance, I’ll give you the context at the very start. I set aside an hour every day to prepare for the next day’s meetings.
- If you’re a founder pitching your startup, you should expect me to have visited your website and read your deck. For more specific information on how I run the pitching process at 27V, read our Operating Manual here.
- For recurring meetings, I maintain a running note 🗒️ to collate our conversation highlights and enlist action items ☑️ for me to follow up on.
- I obsessively use productivity tools – Superhuman, Slack, Notion, Airtable, Zapier, Notability, Calendly, Otter, Command E, Google Drive and even standard OS text replacement ⌨️.
- Ask me about my favorite hacks and I’ll happily share ✌️.
- I’m a nerd for great design, and spend hours ⌛ perfecting the last pixel on a deck. A common theme with all the apps I use is that they’re very well-designed. I care about aesthetics – serif over sans serif fonts, usually…
- I believe to succeed, one must constantly be learning. So, I read voraciously – books, research papers, articles – and I listen to podcasts (10+hrs/week). 📚🎙️
- Please send me content you found valuable 💎!
- My wife says I’m very harsh with my feedback 🤭; which is probably true. However, as I say to all my colleagues – you should know that it comes from a good heart with the intention to be of help.
- I try to be thoughtful when communicating feedback but often struggle with phrasing and tone.
- And I welcome feedback from you. I try to hold myself to very high standards (despite regularly missing them) and would love to hear how you think I can be better both as an investor and as a human (!) 🙌.