I was recently promoted to Partner at Weekend Fund. I started at the fund as a part-time Chief of Staff in 2019 and joined full-time six months later.
The last 3.5 years at Weekend Fund has been exponential for my learning, growth and networking. I was lacking the vocabulary to describe the impact Weekend Fund has had on my career when I came across the idea of a “breakout opportunity” in The Startup of You:
Careers, like start-ups, are also punctuated with breakouts…Our professional lives are not a sequence of equally important jobs. There are always breakout projects, connections, specific experiences, and yes, strokes of luck — that lead to unusually rapid career growth.
The words clicked. Weekend Fund has been a “breakout role” in my career.
Reflecting on my journey at Weekend Fund, here are some lessons I’ve learned on how to see, identify and land a breakout opportunity:
- Expand your network to see more opportunities
- Pick people, not companies, to work for
- Pursue roles that maximize growth
- Start doing the work (you don’t need permission!)
- Bet your career on emerging waves
- To maximize reward, you need to take risks
This post is on what I think you can do to maximize your chances of getting a breakout role, but it’s not a formula to get one. I don’t think such a formula exists. Statistics, not calculus, as Peter Thiel would say. There are unlimited ways to have a rewarding career.
Expand your network to see more opportunities
I got connected with Ryan for the Chief of Staff role after he reached out to a friend of mine for recommendations. Harry Stebbings introduced us (I’m so grateful!). I met Harry through my brother, Varadh, shortly after I moved to London. Harry and I became friends, spending a lot of time talking about startups, venture capital and technology. He shared a lot of personalized advice with me; the ins and outs of venture, his learnings, and observations on the market.
If you’re looking for a breakout opportunity, you’re really looking for breakout connections. The benefits of expanding your network aren’t limited to “high profile” people but also come from peers. Scooter Braun, a talent manager who represents Justin Bieber and others said this:
The mistake of youth is thinking that the mentors you need are older than you. That you should work on getting in a room with some powerful person because that’s going to change your life. It’s not true. What changes your life is your peers… The people you rise up with. They’re your power base.
To build relationships with peers, I wrote a report of the State of the Chief of Staff in Tech, started a talent newsletter called Talent Drops, hosted “Young, not yet arrived VC Society” meetups and more. I got connected with Steeve through running Talent Drops, and ended up connecting him to the team at Afore VC, one of our close co-investors, where he’s now a Venture Partner. Nameet, who ran “Talent Drops” with me is now a close collaborator. Mene, an investor at Chapter One, who read my post about setting up our stack is now a close co-investor and a personal friend.
Having a network of talented people is important for any job but it’s especially important for a job in technology where things move quickly, there is a lot of inequality in access, and the future is unevenly distributed (a part of why we raised our latest fund from 370+ LPs).
The unseen hand in life is the networks that surround us .When you come across people working on something interesting, don’t be afraid to reach out cold (or ask for a warm intro if it’s available). To be clear, this shouldn’t be transactional. This isn’t a game of maximizing LinkedIn connections but instead about investing in meaningful relationships.
Pick people, not companies, to work with
I’ve been lucky enough to work for some great companies. Companies are made up of people, and I’ve learned that growth comes from working with people you can sincerely learn from, people you sincerely look up to. The most valuable skills can’t be taught, but they can be learned.
I didn’t know of Weekend Fund before learning about the opportunity to apply as its Chief of Staff, but I looked up to its founder Ryan Hoover. In my first conversation with Ryan, he lived up to the hype. His charisma, communication, ability to ask the right questions and ability to make people feel “seen” stood out. Even more importantly, he had strong evidence of execution. Ryan is the Founder of Product Hunt, an ally to founders all around the world, and has an extremely strong reputation. Many of his former Product Hunt teammates have had tremendous success beyond their tenure at the company including Niv Dror started Shrug Capital; Erik Torenberg co-founded Village Global and OnDeck; and Andreas Klinger runs Remote First Capital, among others. He also responded extremely fast to emails. Small thing, but it made him feel unstoppable.
Ryan says “The best partnerships look like a Venn diagram.” Ryan and I are aligned in important ways. We’re both extremely curious, highly optimistic, have product backgrounds, are children of entrepreneurs and are eager to experiment. We’re also different in important ways. For one, I grew up India and live in London. My experience is in B2B/infra, his is in consumer/community. I’ve had a different set of life experiences.
I think Ben Casnocha is right about this:
The people you spend the most time with will change you in ways you cannot anticipate or ever fully understand after the fact.
Pursue roles that maximize growth
Breakout opportunities allow you to develop skills, build relationships and gain experiences that lead to rapid growth. They become the dividing lines in careers — steady before, exponential after. When Ryan was leaving PlayHaven, his friend Nathan Bashaw told him:
When you look back at yourself six months from today and don’t feel embarrassed by your naiveté, there’s a problem. That means you’re not learning, growing.
Shortly after he left the company, he started Product Hunt.
Here are some ways I identified the CoS role at Weekend Fund would lead to rapid growth:
- Learn from the best: The founder and GP, Ryan Hoover, was someone I looked up to and could learn from (see point on “Pick people, not companies, to work with”).
- High degree of autonomy: Ryan mentioned in the interview that he would expect the CoS to make up their own work. I would get to work on everything from setting up our stack to investing in early-stage companies to supporting on experiments.
- Access to networks: The role would place me in high-quality networks of founders, LPs (we have 500+ LPs across our funds), and co-investors.
- Grow with the fund: Weekend Fund was early to the wave of emerging funds and had aspirations to become the best fund in its category. This was a wave I wanted to ride.
It’s also important to identify the right type of role to lead to a breakout opportunity. One tactic here is to trace the careers of others who pursued similar opportunities. Does the before vs after look like a minor step or a major step change? I traced the careers of other Chiefs of Staff: Ben Casnocha (ex-CoS to Reid Hoffman), Julia DeWahl (ex-CoS to Eric Wu) and Sam Teller (ex-CoS to Elon Musk). It was clear that their Chief of Staff roles led their careers to take off.
Pick roles based on slope, not Y intercept.
Start doing the work (you don’t need permission!)
I did a venture capital internship in college. I found the work so interesting, it didn’t feel like a “real job”. I knew I wanted to go back into venture “one day”. I started my career at Stripe and then joined TrueLayer in London as their first Product Manager. While working at TrueLayer, I started writing fantasy investment memos. Writing these memos allowed me to pursue my genuine curiosity about venture without quitting my day job. When I came across a company I thought was interesting (usually through a funding announcement), I’d research the product, the market and the team behind it. I’d organize my research into a “fantasy investment memo”. I didn’t have “access” to these deals, the teams or any “intel”, but that only made me more resourceful. The internet makes it easier to start doing the work you want to do (or some version of it).
During the interview process, I shared these memos with Ryan. The role I applied for was competitive (over 600 people applied) and the memos helped me differentiate myself.
If you already know what your breakout role is, start doing the work. You don’t have to quit your day job. Doing so will better prepare you when the right opportunity comes along, you’ll:
- Have more conviction about the role which will make you pursue it with maximum drive
- Be prepared so you don’t have to “scramble” which is especially helpful when roles are moving quickly
- Stand out as these roles can be extremely competitive
The Pmarca Guide to Career Planning is right about going for it:
The world is a very malleable place. If you know what you want, and you go for it with maximum energy and drive and passion, the world will often reconfigure itself around you much more quickly and easily than you would think.
Bet your career on emerging waves
Venture Capital is now 50+ years old and I believe a lot of the action is going to be at emerging funds. There has been an explosion of emerging fund managers since I joined Weekend Fund 3.5 years ago (there are 800+ VCs on AngelList alone). Working at Weekend fund has given me a front-row seat to this movement, and I’ve had the chance to work on a series of experiments to better serve them (OperatorLPs, Signature Block and more).
Breakout opportunities are likely to be where the action is. In turn, the action is likely to be at places that are ahead of emerging waves.
We believe in this point by Dino Becirovic (Where are the next big waves?) at Weekend Fund:
The most impactful and largest startup outcomes arise from betting on small waves on the horizon that become big waves.
I think the same is true for careers. At Weekend Fund, I’ve had a front-row seat to emerging shifts that are shaping our world:
- The shift to remote/distributed work through our investments in Deel, Codi and others
- The emergence of new asset classes through our investments in Pipe, Bonside, Alt and others
- The cultural, regulatory and accessibility shift in psychedelics through our investment in Mindbloom
Read about, listen to and spend time with people building on the frontiers. They often feel messy, but don’t let that throw you off. Search for the “small waves on the horizon growing into big waves” and get ahead of them with your career. The biggest companies, the biggest careers, the biggest fortunes were built as a result.
To maximize reward, you need to take risks
I hold an Indian passport. 11 months into working at Stripe, I lost the H1-B visa lottery, packed up my life and left the U.S. The stress of work visas has always been present in my working life.
When I got the offer to join Weekend Fund full-time, I accepted the role without the certainty I would get the visa to continue living in the U.K (Weekend Fund is U.S based). That said, after working at the fund part-time, I knew that this was a breakout opportunity. The opportunity cost of not taking it felt too high. If the visa didn’t work out, having to leave the U.K was a cost I was willing to pay to work at Weekend Fund. Thankfully, it did work out. I was able to stay in London.
Taking risks, especially early in your career, can have a huge payoff. Look out for opportunities that maximize your risk-reward payoff. Sam Altman makes this point well (How To Be Successful):
I am willing to take as much time as needed between projects to find my next thing. But I always want it to be a project that, if successful, will make the rest of my career look like a footnote.
This is a defining time for Weekend Fund. We’re continuing to experiment with better ways to serve the community around us, leaning into our strengths and building on our learnings. We’re running Signature Block to crowdsource knowledge for emerging fund managers. In 3 months, our posts have reached 175K views. We just welcomed two part-time Analysts, Eric and Selene, to help with sourcing, market mapping, and portfolio support.
The privilege of working at Weekend Fund is never lost on me. I will continue to do my best to serve our founders, LPs, co-investors and the community around us.
Thanks to Ryan Hoover for taking a bet on me by hiring me at Weekend Fund, changing the trajectory of my career, and giving me an opportunity to do work I love with our founders, LPs and co-investors.
Thanks to Harry Stebbings and Varadh Jain for introducing me to Ryan.
Thanks to Laura Clugton, Liam Moore, Rachel Farley, Ryan Hoover, Sheena Shiravi, Suzy Ryoo and Varadh Jain for reading drafts of this.