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While being a venture capital investor has become one of the most sought after careers for a lot of people interested in technology and startups, there’s no one defined path or guidebook on how to become a venture capitalist. For current Accomplice Partner Cack Wilhelm, unconventional has been the name of the game with one constant: working really really hard no matter what she did.
Cack graduated from Princeton in 2006 and started out her career as a Nike sponsored professional runner training for the 2008 Beijing Olympics. How did she end up in the world of venture capital? A mix of hard work, luck, seizing the moment and knowing how to standout and not be forgotten.
Her background as a professional athlete also taught her the importance of finding winners, “I appreciate it in other people when I’m hiring or investing, I’m always looking for that winner attitude, a strong demonstrated sense that you are a winner, you’ve done things and have been a winner, and that you aspire to win. While I didn’t make the Olympic team, I was still in the near pinnacle of the sport trying to get there. I want to see that spark that you’re trying to get there.”
From Running to Banking to Tech
While Cack learned a lot from her 2 years training for the Beijing Olympics, she knew that she ultimately wanted to end up in the world of business. So she decided to swallow her ego and start from ground zero in the working world as an investment-banking analyst at Montgomery & Co. While Montgomery taught her a lot about broad business skills, Cack would be ready to move on after a year.
She shared, “I remember telling my college friends that I was leaving investment banking to sell database software for a company like Oracle. People thought I lost my mind. Knowing that, I did it because I did banking for a year, the second week on the job, Lehman had collapsed, the world was imploding, and afterward, there weren’t a lot of IPOs or mergers.”
After getting the advice of a few mentors and older people she looked up to, she realized that the next best move would be to work at a big tech company and learn a core function. She added, “When I started, I had no clue what databases were but that was the single most valuable decision I made because selling something requires a different understanding of the product and that was my crash course of technology, it was me talking to customers about all their databases, infrastructures and getting a sense of buying cycles and how Oracle deals with quotas that was extremely valuable.”
Early Sales Rep at Cloudera
While Cack knew that she eventually wanted to go to business school, she decided to hop on one more new experience before business school. She shared, “Cloudera was just beginning to start sales, two of my colleagues from Oracle had moved from Oracle to Cloudera and they called me. I knew that I wanted to go to business school so the risk of joining an early stage company would be low.” Cloudera exposed Cack to a new set of technologies including Hadoop, how a fast-growing company operates and how a startup builds and scales a sales team from scratch—experiences that would be valuable in her subsequent careers.
How Business School Led to VC
A year after Cloudera, Cack was headed to business school in UChicago. She shared, “In the West Coast, a lot of people knock business school. But I’ll forever be grateful for my time in business school because it got me the job [in venture capital] afterward.”
Early on Cack knew that the jump from being an inside sales person to VC investor was going to be near impossible but she knew that business school would give her a chance to experiment during the summer. Through a bit of luck, Cack would land a 5-week internship in Scale Venture Partners.
She shared, “I had this job at an early stage startup and I had a second 5 week internship at Scale Venture Partners. I got the opportunity from this friend who I had met in banking and was working at Scale Venture Partners. He saw that I worked in Cloudera and they were trying to get their head around Hadoop, and asked if I wanted to come to do a project.”
Breaking into VC
Cack knew that she needed to give it her bet shot to break into VC. She shared, “I was no fool and I knew that venture is tiny industry so if you have one shot, it is probably your only shot so don’t mess it up.”
During these 5 weeks, Cack realized how much she loved the VC role. She added, “Venture is a really awesome job for the intellectually curious, high metabolism, thoughtful person who loves tech. It was a dream job, and it was a natural fit from the start and for the first time, I really loved my job. I was old; I was 29 and to be really loving my job for the first time was a really inspiring moment for me.”
Towards the end of her 5 weeks, Cack knew that the day she left that they would forget about her and for the most part she would just be remembered as the intern from the summer of 2013 so she decided to make a bold move on her last day, “I went to the office of the managing partner and told him that I loved it and if you give me an offer right here right now, I would sign it.”
What followed was a round of questions from the managing partner, and long story short, Scale Venture Partners would end up giving Cack an offer a few months later, which she signed that same day.
Building Out Accomplice
While Cack really loved her time at Scale, she knew that structurally, she wanted to engage in earlier stage deals across a broader set of industries. She shared, “Scale was B2B, mid stage focused. We had a well defined product market fit and knew what we were looking for. I wanted the opportunity to look at more and invest in more be it consumer, robotics, and frontier tech.”
Additionally, Accomplice had just spun out of Atlas and wanted Cack to build out the SF practice, which was a really exciting opportunity she couldn’t turn down. She added, “Friends asked me why don’t you talk to Lightspeed, Greylock or NEA, but I told them: Trust me on this one. Building, creating and being part of something new is something I want to try and ask me in a decade and we’ll see if it’s successful.”
Advice To Early Stage Founders
Having done sales for both Oracle and Cloudera, Cack is a big believer in the importance of founder led sales during the early days. She shared, “I really do think that I’m all for bringing on sales but there’s a point where it’s too early. The founder should feel early product market fit before they hire outside sales people to create a system. I need to believe that the founders I’m investing in are capable of the founder led sales or they’ll never get to the point where you scale up the team and hit escape velocity.”
She also advices founders to know where the spend for marketing and sales is going and to be really data driven when it comes to spend. She added, “The idea of basing your company value on how much money you’ve raised or how many rounds you’ve taken is a false sense and it should be about how many customers you’re making happy everyday.”
Looking back, Cack is glad that while she took an unconventional path to the world of VC, every stop has helped her realize the constant things one should be doing to succeed: working hard and following through. When asked what it takes to be a good VC, she replied, “It’s really just what it takes to be successful in any field but applied to venture. Just being known as hard working, being quick to reply to emails and to follow through with what you say you will do. I’m amazed by when entrepreneurs say, ‘wow, you actually did what you said you would do’ and I pride myself on being true to my word and I’m going to do it quickly and if you need me, I’m going to be accessible and available.”
You can learn more about Accomplice here.
About the Author: David is a senior at Penn studying Cognitive Science and Computer Science, originally from the Philippines. At Penn, he’s heavily involved in the startup scene as an investment partner at Dorm Room Fund. Currently, he’s working on SkillStackers, the easiest way to scale work using a virtual workforce. Previously, he started a nonprofit organization called YouthHack which has gone on to scale to do programs in over 8 countries in the last 3 years. David enjoys meeting new people and sharing the stories of exceptional entrepreneurs!