Recap: An Automatter Fireside Chat with Vedika Jain

In January, Automatter kicked off our series of Fireside Chats in which we host featured guests for small-group conversations moderated by myself and Jeremy. In these chats, we talk about process, automation, and the unique ways our guests and community use them in their personal or professional lives. Since January, we’ve hosted some amazing guests including Ben Tossell and Amie Pollack, Samir Kaji, and, most recently, Vedika Jain.

Vedika Jain is the Chief of Staff at Weekend Fund, a pre-seed and seed stage fund that invests across verticals in “companies that are capitalizing on a consumer behavior or technology shift.” Prior to entering the world of VC, Vedika worked at Stripe and then as a Product Manager at TrueLayer, an API-first fintech company. 

Vedika recently published a blog post on Weekend Fund’s Tech Stack which garnered quite a bit of attention on Twitter (and showed up in my Twitter DMs no less than 12 times). Automatter was lucky enough to host Vedika for an Automatter Fireside chat to dive deeper into the workflows, tools, and habits that are essential to the VC tech stack. 

Personally, I’d like to note that Vedika was the first “real VC person” to chat with me about automation and process design right around the time that Automatter launched - so I’m incredibly grateful for her wisdom, candor, and friendship!

Here are just a few of the gems pulled from our conversation with Vedika (with a bit of my own commentary inserted):

On why the VC industry doesn’t talk about process and operations…  

  1. An inflated sense of urgency: Operational strategy isn’t prioritized when execution feels urgent.  

“Automation and improving workflows never feels urgent, and investors are spending most of their lives working on things that seem urgent.”

  1. The double edged sword of unlimited resources: Large organizations with abundant resources have a bad habit of throwing people at operational problems. On the flip side, companies or firms with limited resources are typically forced to be more strategic with how they spend their time and money. Automation and process design becomes an opportunity to create more leverage. 

“Leverage is about doing more with less.”

“We can't throw people at problems because we don't have people. If you did have those people, I can definitely see the temptation to do that.”

  1. Emerging micro-funds are increasingly collaborative and benefit from “building in public.”

As a small, solo GP fund that invests at the earliest stage, “it’s really in our best interest to show how we work.” 

On venture capital being a relationship business… 

We often hear that automation doesn’t have a place in venture because it’s a relationship business. But, if you take a look at Weekend Fund’s stack, almost every workflow is centered on building and nurturing relationships with founders - as well as with “introducers.”

Vedika explained that a core part of Weekend Fund’s workflow is about “closing the loop with the person who introduced us [to a founder].” If they end up passing on a deal, they make sure to share the pass email with the person who introduced them to the founder to provide insight into the way that they think as investors. 

This is a genius move. Not just because it helps to maintain and nurture relationships, but because, by sharing insight into the way that they think about potential investments, Vedika and Ryan are leveraging their network to make stronger introductions in the future. They’re using systems and workflows to extend their capacity as a two-person team. 

On the value of having a Product Manager background… 

Vedika started working at Weekend Fund on nights and weekends (literally) while she was still working as a Product Manager during the day.  Ryan, the GP of Weekend Fund, also comes from a product management background. Because of this influence, Weekend Fund’s operations were built through a product management framework. 

Vedika, on starting at Weekend Fund: “It was a product manager dream because there has been very little experimentation in VC product-wise. You could try anything as long as you were willing to be wrong. We really try to bring that product thinking to the fund: thinking about portfolio founders as users, thinking about not yet founders as users as well. Thinking about: what products can we build to help them start more companies?”

Weekend Fund has built a number of tools for their portfolio companies (or potential portfolio companies), including Founder Brainstorms, where they bring together 4-6 portfolio founders for group problem-solving sessions. They’ve also launched Weekend Build to give potential founders the opportunity and leverage to turn their side projects into companies.

“The highest NPS thing we do for our portfolio is called Founder Brainstorms, which are group problem solving sessions. We jump on a call with 4-6 founders from our portfolio, and we’re very explicit that anything that is shared there never leaves that room.”

Another product that comes to mind here is The Community Fund’s Investor Matching Tool, which has been used to facilitate 800+ introductions between founders and investors since May 2020. 

On why it’s so important to prioritize process documentation and automation, even as a small team… 

Across industries, small teams often make the mistake of neglecting process design and documentation. They assume that they can build, maintain, and recall smart processes within their collective brains. They forget that a task without a process will see a process develop organically - and that organic process is typically not the one that will create the most leverage. Vedika discussed why and how Weekend Fund has prioritized process and documentation, even as a two person team.

“The forcing function is being a two person remote team. If I need to act when Ryan is asleep, or he needs to act when I’m asleep, both of us need to have perfect context.”

“When you are big, you almost forget what it's like to be small and scrappy. The traditional way of scaling a venture fund was scaling up. You raised a fund one that was $10M, and if that had a certain TVPI, then you went and raised a larger fund. And at every step, you’d hire one or two people. But I have a saying: ‘Never hire someone for work you wouldn't do yourself, and don't automate work you aren't already doing’. Because what can happen is that you go into this infinite optimization trap where you spend all of your time trying to get the perfect system.”

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On collaborative investing and brokering introductions…  

Weekend Fund’s substantial network is an important part of their moat. Leveraging a large network and facilitating strategic introductions can be a huge operational burden - but it doesn’t have to be. With a healthy dose of Ecosystem Ops, emerging managers and solo GPs can create a huge amount of leverage from their network and alleviate some of the operational burden.

“This hits on the idea of creating network effects around your fund. When you have another portfolio founder, investor, or operator join your network, how do you leave everybody else better off?”

“We do a lot of brokering introductions to investors for our companies. A part of our value prop is that we are often the first to commit and, if we're doing our jobs well, we help our founders close their rounds from better investors, faster. This is extremely operationally intensive. Every time this happens, we send out 10-20 personalized emails to investors. Ideally, there should be a way for founders to request intros directly to the investors and other people in our network.”

On why the future is bright for emerging fund managers… 

“Legacy elements such as being geographically concentrated allowed the secrecy to flourish. The internet and COVID have completely blown up the localization point. All of these new firms are getting off the ground and they have the opportunity to build really strong systems and think very carefully rather than just the classic finance model of throwing bodies at diligence processes and building siloed teams.” - Max Thoeny (Fireside attendee) 

I couldn’t agree more with this sentiment. Why throw bodies at operational challenges when you can just Automate the Andreessen Analyst?

Special thanks to Fireside attendees Ashley Liu, Cheryl Campos, Abena Anim-Somuah, and Max Thoeny for their wonderful contributions to this conversation.

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