From Club Monaco to a Principal in VC

TLDR: Recently, I joined Cultivation Capital as a Principal on their Investment Team. Despite COVID & shelter-in-place, I scaled my VC network over 300% this year, and this post is all about my path into Venture Capital. It also includes 8 actionable tips for those pursuing paths into VC.

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In October 2014, I was a Senior at Vanderbilt University. While sitting in class one day, my Managerial Studies Professor asked us to write down a personal mission statement, a goal for what we wanted our careers to look like over the next few years. When he asked us to read it aloud, I volunteered to go first.

I had written down that I wanted to be disruptive as a buyer in the fashion industry; I remember people being confused why I was using the word disruptive.

The word “disruptive” sometimes gets a bad rep, but I meant it in the sense that I wanted to be a force for good, and to change fashion’s perception. I wanted to move the industry forward in a more sustainable manner, which was also more democratic and less elite.

I spent the first 5 years out of college driving product-led growth and operations for a wide variety of consumer brands. I worked on more than 10 different business models and spent most of my time identifying new opportunities (i.e. a new vendor or category). On top of that, I was pitching these investment strategies to executive leadership. Ironically, building and managing an assortment of brands carries a lot of similarities to portfolio construction.

Yet, all the while, the one constant bottleneck for my longer term view of my career was that in Fashion and in Corporate Retail, it is extremely hard to convince people to change their perspective.

So in 2018, I launched my own venture, VER CO., a DTC fashion brand making sustainability more accessible and affordable to millennial women.

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The best advice I can give to anyone pursuing a career in venture is to build something first. Empathy for the entrepreneurial journey is REALLY different when you’ve been on the other side of the table as a founder; you are significantly more aware of potential knowledge gaps.

This brings me to my most important point:

The quicker you can ascertain what you know vs. what you don’t, the sooner you’ll be able to truly lean into your strengths and openly discuss knowledge gaps and learning opportunities without fear of judgment or failure.

My introduction to VC was through the eyes of a first time founder who knew very little. I always wanted to further educate myself, but also was eager to share that information with other founders in my personal network. I ended up immersing myself in the VC landscape, and soon became obsessed with learning about new industries and tracking early stage incumbents.

And the one theme I had so desperately longed for in my career, “to be disruptive,” was the common motivation shared amongst all the entrepreneurs, operators, and investors in the space.

As the old phrase goes, “this must be the place.”

At the same time, I made the difficult decision to migrate back from Full Time to Part Time Founder and joined Club Monaco, as an Associate Merchandise Planner. On the side, I was heavily focused on building & showing my capacity to build. I already had a solid network of founders (400+), but continued to scale that network across a wider range of industries. I attended every pitch night and Ask Me Anything, and eventually started informally advising numerous founders in my circle.

Then, one day at an AWS Loft event, a guy came up to me, and asked me if I was a founder. I didn’t know how to respond. For some reason, I just kept it simple. “Yes, but I’m looking to transition into VC.” Who knows why I told a stranger about my secret passion, but he gave me his card and we kept in touch. At the time, Ben was a Principal at Starta Ventures, and ran Starta’s Accelerator program.

Ben sent me several book recommendations, John Gannon’s newsletter, and lots of advice for my VC job search. Then, almost 7 months later, he asked me if I’d be interested in a Portfolio Support Internship to support some of the Retail Tech startups in Batch #9 of Starta’s Accelerator program. I said yes.

About two weeks into the role, Covid hit. A lot of the magic of Accelerators is the in-person community and events programming, but I refused to be discouraged. I stayed engaged and involved with Starta, and in June, I was asked to assist with sourcing startups for the next cohort as a Summer Associate.

As shelter-in-place continued, I doubled down on scaling my VC network and mostly prioritized building new relationships. At this time, I had also started GoingVC’s educational program, so I was doing lots of reading and assignments on topics like Valuations and Cap Tables. I also was actively tracking opportunities and building an investment thesis around Sustainable Food and Beverage with my colleague, Cameron Demsey.

We even launched Future Of, an event series to engage the wider community around Sustainability and Tech. I spent a lot of time performing market research, industry analysis, and competitive landscapes; that project gave me the opportunity to develop a unique point of view on the space.

The value of Investment Thesis work cannot be understated; this work is imperative to making strong impressions when networking with VCs. In addition, I was sourcing about 25 pre-seed opportunities a week for Starta.

All in all, I scaled my VC connectivity over 300% this year in just a few short months. A lot of those first Zoom calls came through warm introductions from founders or other VCs, who knew me since the beginning of my search. The rest were through cold emails (a separate post on the power of cold emails coming soon!!)

And now, I can say I’ve done it. I’m officially joining Cultivation Capital as a Principal on their Investment Team. When I first met with the Cultivation team, I was immediately drawn to the team’s focus on nurturing strong relationships within the Investor community and community-driven approach to sourcing. In addition, Cultivation’s thesis on identifying undercapitalized markets ripe for disruption deeply aligns with the more diverse and equitable future I hope to drive forward for the broader VC landscape.

If you’re an early stage founder in the Software and IT space building in the Midwest or Southeast, please don’t hesitate to reach out to me. I can’t wait to meet you!

Last (but certainly not least), don’t underestimate the power of building even if it’s just an intimate community of founders and VCs in your corner. These are the same folks, who may tell you about a job that’s not yet posted, or better yet send over the strongest recommendation or referral for you as a candidate.

Bonus: here are a few additional tips for your VC job search. A few things I’ve learned throughout my journey.

1. Treat every informal coffee or Zoom as if it’s your last round interview.

Emphasize how you think as opposed to what you think. Ensure your personal decision making process for previous life events is clear and well founded.

2. Let go of personal anecdotes; leverage data instead.

It’s evident that historically there’s been a lot of bias in VC; if you’re someone joining this community, I encourage you to advocate to change this. It is imperative; lots of amazing firms have already scaled up massive internal data infrastructure to be disruptive.

3. Be yourself and have fun.

These Zoom calls can be awkward and dry. Make sure you have perfect lighting. I recommend sitting by a window in which you can get natural light & dressing up as you would in person. Make sure you’re sitting up appropriately and centered well on the screen, and just…

Try to relax and enjoy the process! I can assure you that you’ll meet some amazing people and learn a great deal throughout the process.

4. Stay in touch.

The one thing that’s true for any relationship is that they take time. You can easily stay engaged by commenting on LinkedIn posts, retweeting folks you’ve connected with, or even shooting them an interesting article. I’d also encourage you to share updates regarding what you’re currently working on; great examples might include a relevant Investment Thesis or potential investment opportunities for the VC you’re talking to.

5. Prioritize the quality of your relationships vs. the quantity.

While it’s imperative to track founder conversations and actively monitor the scalability of your network, always ensure there are at least 10 founders, who you’ve over-delivered significant value to. These founders will be the champions for you in the rooms or Zooms that you’re not in and will always sing your highest praises.

6. In a post COVID world, when we return to IRL events, understand that it’s not about being the loudest person in the room or asking the most questions.

I highly recommend optimizing for just one strong connection at each event whether it’s someone from the audience or someone on stage.

7. Ask for what you want.

Similar to my story with Ben, in VC, as in anything else, it’s imperative to be clear about your goals and what support you are looking for.

8. Don’t be afraid to reach out to ME!

My email is amann@cultivationcapital.com or you can find me on LinkedIn, Twitter and Instagram as well at @itsalanamann :)

Special thanks to: Ben Reiter, Isabela Becerra of 8VC, Luke Armour of Chaac Ventures, Nicole Johnson of Forerunner Ventures, Nikita Singareddy of RRE Ventures, Brett Andersen of Bullish, Tina Dai of Silverton Partners, Natalie Dillon of Maveron, Bryan Rosenblatt of Craft Ventures, Gautam Gupta of M13, Micah Rosenbloom of Founder Collective, Geri Kirilova of Laconia Capital, Andy Cloyd of Revolution, John Gannon of GoingVC, and all the amazing entrepreneurs I’ve had the opportunity to support and work with: you all inspire me deeply and continue to make this journey worthwhile!

Written by

Principal @ Cultivation Capital. Rooting for underrepresented founders & those building in undercapitalized geographies.

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