Things about being a VC I wish I knew 2 years ago —part I

Ana Wolsztajn
4 min readMay 23, 2021

I can’t say getting into the world of investing and VC was my dream since I was a kid (didn’t know about a career path like that back then 😉). But over the years working at startups and with startups at accelerators and events, I realized my very special way of seeing things and connecting dots can nicely match with the job requirements — if venture capital funds were open to ever hire someone like me.

My Sesame family in their natural habitat (pre-Covid ofc). Photo by Dan Taylor.

The opportunity to at least try to get a shot at this career presented itself in 2019 as Included VC — the first fellowship with the aim to open venture capital to underdogs and overachievers with diverse stories, still hardly seen in VC firms. I remember the warm, summery night I spent writing the essays in my application, pouring my heart and soul into every vulnerable answer. Few months and a number of interviews later I was ready to join the very first cohort.

Standing in front of the group, shy of 30 fellows from all around the globe, chosen from around 1.5K applicants to meet with the mentors and learn from founding partners and seasoned investors at European VC firms at the summit in Berlin I felt a mix of imposter syndrome, the pride of getting there, and gratitude.

Sure, it wasn’t my first summit being surrounded by inspiring leaders and innovators (vide my events gigs at Startup Sesame Summit, Singularity University, Turing Festival, SLUSH, Pioneers, Leaders Paris, Engage Prague, Wolves Summit, Techfestival CPH, and obviously countless SaaStock on Tour and in Dublin conferences), but this time I was not just an observer, member of the behind-the-scenes crew, and admirer, I was stepping up and stepping in.

The gang at the end of the 1st (and only offline) INVC summit in Berlin

Still a bit hazed by jetlag, I’ve spent the late hours of the night working on my presentation and rehearsing for the next day. In the hindsight, it seems like a taster of what’s life in VC is like: you put in the work, get this one extra push, and then there are some happy moments when all works out and it’s been all worth it.

A year later, even before graduating from the Included VC fellowship, I was braving my way to venture capital — starting with a summer gig at Balderton (I consider it a good omen to follow in the steps of Harry Stebbings of 20VC). Remote due to lockdowns, I took it upon myself to zoom-meet for lunch or morning coffee with many of my insanely clever colleagues.

Coming fall, after an intense few weeks of interviewing around Europe, I ended up in Prague, joining my mentors at KAYA.VC (back then still known as Enern) for a full-time hybrid position that allows me to care for our portfolio startups, take an active voice in the brand development, as well as sourcing deals, and investing alongside the team.

KAYA Team. From top left: Martin, Tom O., Jakub, me, Tom P., Pavel

But even the long, MBA-like, fellowship didn’t prepare me for the mindblower of everyday challenges of a VC life. What did I wish someone told me before?

  • It’s fiercely competitive — from the moment you decide to start applying till the moment you retire. Oh and if you ever wondered where all the debaters and contrarians at… IC (Investment Committee) may be a good bet.
  • The saying about working smarter not harder doesn’t apply — to survive and thrive you need to do both. So if you were considering switching to venture capital because the startup pace is too crazy, think again.
  • Following on the previous point: decision fatigue is real, especially after days filled with pitchdeck reviews, zoom calls with founders, and team debates. That's when the passion for what you do comes in handy.
  • Being diverse means you’ll be one of a kind, and that presents you with an extra set of challenges when interacting with the team, LPs, founders… You definitely need a lot of grit and determination to keep at it. But it can also become your unfair advantage (if you think about yourself as a startup endeavor of sorts ;) ). What helped me is this interview with Michael Moritz, once upon a time a diversity hire, now Partner, at Sequoia Capital:

I like to think that if I persevere along with a number of others considered diverse now, in a decade or two people will smile and question how someone like me was ever seen as a diverse hire. And female VCs will invest in both male and female founders equally just like their male colleagues, investors being immigrants themselves will be open to founders from different schools, countries, socioeconomic backgrounds. Finally, disability will be normalized and neurodiversity cherished as yet one more unfair advantage — both on the founders’ and investors’ side. And all this will bring to life a new generation of a truly diverse herd of unicorns. Doesn’t it sound like a great future to look forward to?

Till this future materializes itself, I plan to do my part — searching for the future tech decacorns in Europe and beyond, while practicing candor and fortitude.

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Ana Wolsztajn

Seed Investor | Brand Storyteller | ex-Tech Journo @ Tech.eu | Included.VC and VC Unlocked Alumna | VC @ KAYA.VC | Coffee Geek, Sci-Fi Nerd & Travel Foodie |