Staying Uncomfortable (or What Got You Here, Won’t Get You There)

Every year, I spend the week directly after New Year’s thinking through my goals for the year.

You can check out some of the previous posts here – but its interesting to go back and read through how the “main” focus for my role has evolved over time.

2010: Engage with team
2011: Work with portfolio and platform
2012: Learning deals and investments
2013: Form own opinions and become more external facing

This process was based on feedback from a mentor at Perfect Wave Records early on who noticed I was struggling (and continued to struggle with) giving up control at individual events as the business scaled.

Even as we had 8 people working with us, I still wanted to be at every event and be involved in every small decision – and while that attention to detail had been great when it was just me throwing concerts – as we brought on more individuals and began to add business lines – our success would no longer be based on those skills, but rather my ability to hire and manage talent and work bigger business deals. (And my inability to really understand that advice then was one of the big issues that led to eventually winding the business down.)

As such, my focus at University (and projects since) has been driven by the question – with where you are today, what are the missing skills that help you (and the business get to the next level)

For True, when I joined 3 years ago, I didn’t really have a job title or direct responsibilities. We liked each other and thought we’d be able to figure out a role together – either inside the fund or within the portfolio.

So when I joined (and really in the months leading up to joining), I spent an incredible amount of time meeting with folks involved in the venture ecosystem (early-stage investors, startup founders, incubators, etc) and trying to better know the True team. Internal goals included things like “One Lunch a Week with Someone at the Firm”, “Say Yes to Any External Event with Colleagues”, “Find What People are Passionate About and Try It With Them”

The goal was to get deeply acclimated with the team, how they think, and understand the firm as well as the broader industry – with the idea I’d be able to figure out the type of role I’d like to pursue and have the relationships built to support that decision.

In January 2011, this led to the next set of goals – “Work with Platform and Team.” At the time, we were still a small group and the portfolio had grown quickly in 2010. A big part of our offering to Founders is access to our the True Platform (or our group of ~220 Founders) and the events related to it.  We had a small team focused on hosting events, providing services, and generally making sure our Founders stayed connected.

For this year, the focus was to stay close to the team, help proactively with events, and pick up ad-hoc one off projects for specific portfolio companies (some of which that fit into my background and others that were totally new.)

In 2012, the goals focused to learning more about the deal portion of the business – specifically looking to begin working closely with individuals partners on specific deals (and reading every legal document), interacting with Founders on an ongoing basis, and digging into specific markets where individual partners had research interests. (Mainly enterprise infrastructure)

Going into 2013, I didn’t write a blog post – but the focus begun to shift more external facing – leveraging the experiences of the last three years to start to build a book of business in the venture business.  Many of these goals are directly related to developing my own thinking around markets and sourcing deals, writing and speaking more publicly, and hosting events (small and large) which help solidify relationships in broader industry.

Writing about it in a retrospective makes it seem way cleaner and planned out – the reality is that there’s a lot of overlap and messiness from year to year (as you can see from the old blog posts) – but the common thread was a desire to maintain an appropriate level of discomfort to keep growing every year.

This post came out of a conversation this weekend around when being comfortable – to which I said – I’m only really comfortable when I’m not completely comfortable.


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I work for True Ventures, an early-stage venture capital fund with offices in San Francisco and Palo Alto. We partner with promising entrepreneurs at the earliest stages in the technology market providing hands-on management support to guide our portfolio companies through the challenges of early growth.