Honestly, Still Breaking into Venture
One year ago, as the world shut down due to COVID-19, I joined the Unshackled team as an investor. Making the jump from the First Round platform team to the Unshackled Investment team has been challenging but incredibly rewarding. Over the past year, I have reviewed 1,670 companies, taken 254 pitches, been a part of 11 new investments, and led 1 investment internally. I am constantly learning something new every day from my team and the brilliant founders we work with.
I read a lot about the next generation of investors looking to “break into” venture, and like any good associate, I just want to be helpful. Below are some of my learnings, tips, and tricks for anyone that is thinking that venture is the right path for them.
Venture is a marathon full of 1-mile sprints; train accordingly
The emails, meetings, research, and writing never ends. I have maintained some sanity by really leaning into my type-A personality. Based on teachings and wisdom from my former colleagues, Chris Brown and Megan Kelly I try to keep a very organized calendar to optimize my time. I also work out every day (find me on Whoop, Strava, and Peloton) so that I don’t go totally crazy. The importance of this time blocking strategy is twofold: (1) not only am I able to leave time for all-important deep work but (2) transparency allows my team to respect my optimized work schedule — boundaries are very important, especially in the time of COVID.
My known unknowns have increased 10x
I am acutely aware of what I do not know and have really committed to being honest and vulnerable to my team and founders. I have completed hours of research in the last year, read books, taken Harrison Metal’s General Management, joined an AllRaise Associate cohort, attended a venture financial modeling class, and completed deep dives in everything from API 101 to the Hedra and Hashgraph ecosystem — and yet I know that I have years of learning ahead of me. My advice? Get comfortable with not being comfortable.
Ask good questions and then 🤫 and listen
This is the hardest lesson I have tried to learn since kindergarten. Every single teacher, camp counselor, professor, and manager will tell you the same thing about me — It does not matter where you seat Sarah, she will talk to everyone. I have learned that it is not enough to just talk to everyone, you have to be asking the right questions and then, shut up and listen. Phin Barnes (former FRC Partner) is an excellent coach and teacher, and the best thing he taught me is the art of the ‘5-second pause’…ask a question and then lean into the silence, forcing the person to answer.
Have strong opinions, loosely held
After any meeting, the partners at Unshackled will always ask “the kids” what we thought first. It is as important to have an opinion as it is to admit that with new information your opinion can change. I like to say that I have “strong opinions, loosely held.” I will bang on the table for a deal or a founder, but with new information, I am comfortable changing my mind. I think the ability to gracefully change one’s mind is a key skill in venture.
Venture is a sales and customer success role, lean into it
I did not study finance, nor did I work in IBanking or consulting. My first job was as an early sales team member at a series A startup in NYC. My hot take? Every VC should do a stint as an SDR. During my time at Vettery I learned that cold calling is not for the faint-hearted, you have to perfectly position your product to sell it, and that sales team culture is very important to the success of a company. Honestly, I was not a very good SDR, I was not aggressive enough on the phone and did not always hit quota. I was, however, fortunate to work at a company with founders that cared about their team and was allowed to transition into a customer success seat. On the CS team, I learned that I am much better at problem-solving for people that have already agreed to use a product than I am at cold selling. As an Associate at Unshackled, I use a ton of the skills that I learned at that first job such as helping our teams write cold sales emails, vetting their sales tools stack, and stressing the importance of supporting young team members and letting them grow. Leaning into these skills has made me an asset.
Venture is a notoriously unstructured role, and I knew that I was at a point in my career where I was ready to be the builder of my own structure and goals. I hope to be “breaking into venture” for years to come because I never want to be complacent and stop learning. My one-year learnings in summary:
- Start off being hyper-organized with your calendar so when everything lights on fire at the same time you can handle it
- Get comfortable with your known unknowns
- You are not the ‘expert’ but you can ask the right questions to get to key information
- Have an opinion, and be willing to change it
- Venture is a sales and customer success you are selling capital and founders can submit support tickets that have to be answered ASAP
As I race into my second year as an investor, it’s this I’ll be mindful of most of all — staying curious, empathetic, and surrounding myself with the best in class (immigrant founders, I’m looking at you!) I love helping people with “untraditional” venture backgrounds think about their futures. I am the first to admit that I have a chip on my shoulder about attending a mid-tier state school, working in sales, being a recruiter, and now being an active investor. If this sounds like you please reach out (Sarah [at] unshackledvc [dot] com)! There is no one background for venture and diversity in background, education, and thought will only make the industry stronger.
