My Path from Fashion to VC Investor at Madrona
TLDR: I will be joining Madrona Venture Group as an Investor in October 2021. I am thrilled to be working with this incredible team to invest in and support impressive founders from day one. If you asked me what I wanted to do for my career a few years ago, I would have told you I wanted to be an artist or fashion designer. In this post I share my path into venture capital and action steps for people pursuing paths into VC. If you’re a founder in the Pacific Northwest or thinking about starting a company, I would love to meet you. My email is firstname.lastname@example.org (I’ll reply after I start) or you can find me on LinkedIn or Twitter!
Your interests will change, and your experiences will provide a perspective. I am not your traditional economics major that spent two years in investment banking and landed a job at a venture capital fund. If you asked me in high school what I envisioned for my lifetime career and profession, I would have responded that I wanted to start my own fashion company and create a more sustainable fashion industry. I was an artistic child but also enjoyed math and science classes. I wanted to apply my interest in innovation to something about which I was passionate, which was clothing. After trying to convince my parents to let me go to art school, I found myself at Washington University in St. Louis (WashU) as a fine art major. I remember during freshman orientation finding out, WashU had an undergraduate business school, Olin Business School, and thinking, “this is great, I can take business classes to help my art or fashion business.” Freshmen fall I signed up for calculus, economics, and all the entry level business school courses. I would run across campus between art studio classes and statistics courses. I eagerly cold emailed numerous fashion companies until I landed summer internships in New York City as a designer at Zac Posen and Proenza Schouler. After both internships, I concluded that to have the level of impact I desired, I needed to run the business instead of being a designer, so I switched into the business school at WashU. I feel in love with the entrepreneurship programs, wrote a business plan senior year for a DTC brand focused on the circular economy, and pitched angel investors. I was clueless about all of this when I applied to WashU four years earlier! I had no idea undergraduate business was an option, and I ended up graduating with three majors in Marketing, Entrepreneurship, and Design. The key is to be open minded because you never know where you may end up.
Blogging opens doors. Through working on my own DTC brand during college, I realized many of the best consumer businesses today are grounded in media and community. So I decided to launch a blog, The Power Thread. I started interviewing small business owners, entrepreneurs, and people with unique career paths. Soon people started volunteering to write for The Power Thread, make graphic designs, and produce content. We realized most of our interviews featured women with entrepreneurial career paths and that our best performing content discussed entrepreneurship, mental health, sustainability, and feminism. We responded by producing storytelling content that aligned with those themes. After a year, we were a team of 10 part-time people who contributed content weekly and 25 student ambassadors from colleges across the U.S. We even had a contributor in Australia! I continued building The Power Thread on the side of my job at Gap Inc after college.
Have a range of experience in one job. When college graduation came, I decided to accept an opportunity to be in the Rotational Management Program at Gap Inc. I was excited that I could combine my quantitative and creative sides into my job. The rotational program was incredible and exposed me to more than 10 business models. I rotated through multiple product-lead growth functions and eventually landed in a merchandising function where I developed and executed the strategy for the Gap Women’s Sleep and Lounge business. I came to Gap wanting to change the fashion industry in a positive, sustainable way. I was super excited to help Gap be the most sustainable, democratic, American brand. While it was an amazing learning opportunity, I felt stuck and unable to create the change I envisioned. Fashion and corporate retail are extremely complex businesses and hard to change.
For a consumer business, everything comes down to the customer and the product. The goal is to create an incredible experience for the customer with the best product. Every other strategy or goal needs to align to the customer and the product goals. Working at Gap provided me valuable insight into the operations of a large corporation and a consumer business. In unexpected and surprising ways, managing an assortment of 150+ products have many similarities to portfolio construction. Like venture capital funds, Gap had a Monday business meeting where I would present updates on my product portfolio, and we had a monthly investment review, but instead of investing in startups we invested in apparel product assortments.
Side projects are the best way to explore your interests. Realizing I wanted to have an entrepreneurial career, I continued managing The Power Thread on the side of work at Gap. I would regularly wake up at 5:00AM, work on The Power Thread 5:15-6:45AM, go to a 7:00AM workout class, and be at Gap by 8:45AM for work. As our Power Thread team grew, we started posting content daily. We launched a weekly newsletter and started hosting panels and workshops quarterly in New York City. The following grew to more than 14,000 people and the Slack channel became increasingly active. I realized that having an ad based business model simply was unsustainable, but there was opportunity to leverage the network, brand, and community to build something new.
Your peers are the best mentors. Before the pandemic, my college friend Rani Kubersky asked to meet over coffee because she was interested in careers in retail. Rani and I were not close friends, but I always had a lot of respect for her and wanted to learn about her experience in investment banking. During our meeting she mentioned that she interned at a venture capital fund for two years during college and was interested in doing some investing on the side of work. My response was, “so cool, I know all these founders from The Power Thread that you can invest in.” After a few minutes of discussing, I said, “let’s turn The Power Thread into a VC fund!” As slightly naive but driven 23-year-old women, we started strategizing how to raise a fund. When the pandemic sent us home from work, in 2020, we would sit on Zoom together after work, daily developing an investment thesis, networking with founders, and searching for angel investors.
Reach out and ask questions. One of our mentors suggested we start raising syndicates to build a track record. We started conducting diligence on startups, writing investment memos, and we circulated opportunities to angel investors that we met over Twitter and Zoom during the past year.
Learn by doing. When a company had a lot of interest, we would raise a syndicate. This meant accepting $1-25K checks from accredited angel investors and then writing one ~$50K check to the startup for ownership in the company. We were uncompensated for this, but did it for the experience and learning opportunity, and we were in position to take 20% carry at exit. Our investments include: Brij, Dirty Labs, Couplet Coffee, Leda Health, and an angel investment in Solv.
Offer to help people, teach them something, and build your network. Each of our investments are in values-driven consumer companies. Neither Rani or I were accredited, so we were unable to personally invest in our syndicates, and less than 5% of the capital raised originated from our families. Most investors were people we met on Zoom over the past year, and more than 80% of investors in our syndicates were women. We now have a network of more than 300 angel investors, and more than 50 strategic contacts and advisors. To build relationships, ask people about their challenges and how you can help them. Whenever you meet someone take note of what excites them and what is most top of mind for them. Then check in regularly, send them articles, invite them to events, and introduce them to other contacts in your network. People want to learn, so if you can teach someone something new during a call, offer advice, or share a fact, you will add value. They will remember you. But listen first and see what people want. Demonstrate that you understand them.
You work for founders as an investor. As 25-year-old women, Rani and I bring unique perspectives to every cap table and add value through community building, hiring, mini-projects, and introductions to funds for future rounds. Always be responsive to founders, even if you have more 200 emails per day. Help founders first because without founders there are no investors.
Don’t be afraid to be an intern again. Prior to the Covid-19 pandemic, I had no idea what a syndicate was and had little knowledge of venture capital besides knowing that they invest in startups. Asking questions and leaning into my interests was an invaluable learning experience. In January of 2021, I realized I wanted to work at a VC fund fulltime. I reached out to one of our mentors, Liz Gordon at L Catterton. She was incredibly supportive and connected me to her friend Claire Smilow at Box Group. Claire said the best way to find an investing role at a venture capital fund is to already be doing the job and find a fund where you can bring a new perspective and fill a white space on the team. She also emphasized the value of internships at VC funds. I started applying to almost every VC internship, fellowship, analyst, and associate role at funds in cities across the U.S. I would email fund partners explaining that although I’m not an MBA student, I want to be part of their MBA internship program. In April, Armory Square Ventures offered me an opportunity to be a Venture Fellow for the Spring and K50 Ventures offered me an opportunity to be a Summer Associate. Both funds knew I would be actively interviewing for investor roles at VC funds during the internships. Knowing that I had about six months of internships at VC funds lined up, I made the decision to leave Gap.
Always leave a job on good terms, with a plan, and know that time is your most valuable asset. Do not just quit your job because you no longer want to do it or think it’s not the right fit. I gave my job at Gap 110% every day for more than a year knowing it wasn’t the right fit. On the side I explored other options in order to figure out what I should be doing for my career. This allowed me to make a thoughtful and calculated decision. I made the decision to leave Gap when I knew I had six months of internships that would enable me to reach my goal of being a VC fund investor. I do want to acknowledge that it is a privilege to be able to do this. I did not have student loans, had saved money over the past few years, and had a supportive family that enabled me to take the risk of reducing my income for a few months. There is a lack of diversity in VC and the challenging path to VC reduces diversity among the applicant pool.
When you make career decisions do not worry about disappointing other people. When I left my job at Gap I was scared. I thought I would disappoint my team, my parents, and my friends. Take everyone’s advice with a grain of salt. Many people gave great advise as I evaluated opportunities and made decisions. But many people gave me what later proved to be bad advice, or at least not being in line with my needs and ultimate decision. Over time, I realized there is no concept of disappointing people. People may disagree with your decision and have recommendations for a different path, but ultimately you are the one most impacted by the decisions you make. Do not worry about what other people think because they are not you, and they don’t think about you that much.
Find the opportunity where you will learn the most. It takes 10 years to really know if you have the talent for this job because it can take up to 15 years to exit an entire portfolio of companies. Consequently, funds that have raised multiple funds and have been investing for more than 10 years have incredible knowledge and experience. VC is a mentorship industry; earlier career employees learn from partners and managing directors. So I decided to target working with partners and managing directors that have been investing for more than 10 years. Another personal goal was to diversify my experience and have exposure to both consumer and enterprise businesses. I wanted to find a fund where I could bring my perspective, add value to the team, and learn in new ways.
Think about how you feel after each interview. After my first interview with Madrona, I remember saying to my parents, that was my favorite interview at a VC fund! I felt challenged during the conversation and case study, but in a healthy way. Every interview with the Madrona team confirmed I would be pushed outside of my comfort zone and forced to grow in a constructive and non-intimidating way. The Madrona team showed they are collaborative, honest, open-minded, humble, passionate, and incredibly smart. After each interview I thought, “Wow! This person is awesome.” I am truly lucky to be joining a fund with an incredible history and future ahead.
If you want to be an investor at a VC fund, be patient and gather a range of experiences. The most important advice I can offer is to recognize that the interview process is unlike any other job interview process. And it is long, tedious, and challenging. Many funds have 2-5 employees and may hire one person every three years. Friends of mine have shared experiences of interviewing with funds that last for more than six months. Funds interview candidates much the same way as they diligence company founders. You should interview with funds where you can bring a different perspective. At the start of my process, I was targeting consumer-only funds that invested in future retail companies. I quickly realized; however, I could not bring a new perspective to those teams. They already had the knowledge I would bring from Gap. Instead, find funds that are growing and want a new perspective on their team. Madrona is a perfect fit for me because they want to engage in more consumer investing. I have a different background than most of the team, so I can fill a white space on the investment team. I will also benefit and grow because I will be working with people that have different perspectives, interests, and experiences. Here is a summary of tips for breaking into VC.
Start doing the job before having the job. That doesn’t mean you have to invest. You can do this by tracking startups and developing an investment thesis.
Have operating experience. Working at a company and operating a business helps to empathize with entrepreneurs and realize that companies are not hypothetical.
Bring a unique perspective. Anyone can learn financial modeling and develop hard skills, but a perspective comes from prior experience in specific industries.
Find a white space at a VC firm that you can fill.
Treat every coffee meeting or Zoom call like a first round interview. Emphasize how you think. Describe your interests. Ask questions. Share your goals. And always offer to help the other person first.
Listen and give first. Constantly find ways you can help everyone you meet.
Be yourself. You can be very qualified and an incredible investor, but not the right fit for many funds. It’s not personal. You may get rejected from a fund because the fund wants someone with experience specifically working at a B2B SaaS company or someone with experience investing in LATAM. Every fund has a different need.
Stay in touch. Send people updates. Share deal flow. Hiring needs and interests change monthly. Maybe there are future opportunities to work together. If a fund moves forward with other candidates, ask if they would be able to connect you with a contact at another fund that may be a stronger fit.
Prioritize your time. What is your goal and what things can you put aside to allow more time towards reaching your goal? Time is your most valuable asset.
Prioritize quality relationships and peer mentors. Stay close with a few mentors, peers, and founders. I would not have known I wanted to work at a VC fund but for my peer mentor Rani Kubersky. Peer mentorship is incredibly valuable.
Special thank you to my incredible mentors and friends: Adriel Bercow of K50 Ventures, Andy Cloyd of Revolution, Claire Biernacki of BBG Ventures, Claire Smilow of Box Group, Julia Maltby of Flybridge, Kait Stephens founder of Brij, Liz Gordon of L Catterton, Madison McIlwain of Defy, Meagan Loyst of Lerer Hippeau, Neenah Jain of Armory Square Ventures, Rani Kubersky at Stern, Rich Keller brand marketer, Shriya Nevatia of On Deck Catalyst, my parents, and my sister Danielle.