Efficiency Tips from a VC

As a VC, I’m always pressed for time. Between performing due diligence, supporting portfolio companies, developing investment theses, meeting with founders, raising a new fund, and writing the periodic blogpost, it’s often difficult to prioritize my schedule. Being a new parent adds another layer of complexity to matters, not to mention the lack of sleep. For these reasons, I’ve developed a comprehensive strategy to optimize my efficiency. I’ve found this strategy to be highly effective and hope that it’s helpful for others. The three pillars of this strategy are utilizing tools, managing energy, and avoiding wasted time. 

UTILIZING TOOLS 

I credit one of my mentors, Jim Matheson, for encouraging me to think hard about tool utilization. Jim is currently the CEO of Oasys Water and VC with Flagship Ventures. I’m grateful to Jim for imparting the importance of selecting the right tools as early as possible in any new position. Any tool we use for business tends to be sticky, so it’s important to not get too attached to tools that will slow you down. 

For example, my favorite efficiency tool is Evernote. It’s such a simple idea, a note pad that syncs on your phone and laptop via the cloud, and yet it is incredibly powerful. Right now, I have the ability to instantly look up my notes from almost every conversation I’ve had over the past two years. This especially useful in fostering relationships with folks I don’t interact with every day. Whenever I have a meeting with someone I haven’t seen in a while, I just look up my notes from our last conversation. You should see people’s eyes light up when I can remember things they said years prior. Try doing this with your Moleskin notebook. I remember a colleague of mine who started carrying two moleskins to every meeting. After inquiring, he admitted that he need to reference his old notebook frequently while starting to write in the new notebook. You can imagine how much time is wasted managing this antiquated organizational system. And good luck looking up anything in any reasonably short amount of time, assuming you even have the right notebook handy. 

I used to keep an Excel spreadsheet on my desktop with a list of my “To Do’s.” It was prioritized, color coded, and even gave me alerts if I missed a deadline. It was pretty slick, but I spent a lot of time managing it. The bigger issue is that it wasn’t cloud-based. If I needed to check the list or add a task while I was on the go, it was impossible. There are a number of cloud-based tools and apps out there, but I prefer ToodleDo. It allows you to prioritize and categorize action items, to apply due dates and reminders, to generate a “hot list” of action items for the day, and it syncs in real time across all my devices - even my Apple Watch. The power of goal setting and task management has been well documented and researched (so I won’t spend time convincing you of this), but this tool has everything you need at a modest price point. 

The third tool I use is my Outlook Calendar. Like most people I used my calendar to schedule meetings and calls with colleagues and manage appointments. Unlike many, I also use it to map out each day and to ensure I complete the tasks I’ve identified as critical for that particular day. Every morning, I look at my ToDo list and figure out what I want to accomplish that day. I then make a quick plan of what I wish to do when. Then I actually put placeholders in my calendar for things I need to do. This helps serve as reminder of what I need to get done and actually reserves the time to complete each task. By having a firm start and stop time in my calendar, it helps me focus in on the one task, without getting distracted by others. In addition, often I’ll challenge myself to complete tasks in less time than I’ve allocated (e.g. an hour long task in 30 or 45 minutes). This keeps me on the ball. I even build breaks into my schedule, so that I can catch up on email or respond to unanticipated tasks that arise throughout the day. Sometimes, I just need a quick 5-10 minutes to transition from one task to another. Otherwise, I’ll use the break to take a quick walk or grab a fresh coffee. 

Tools are sticky. We often get attached to our tools and the perceived switching costs become rather high. For this reason, it’s good to think hard about what tools you need and why. Then do some research and find the best tools for you. 

MANAGING ENERGY 

I find managing my energy levels to be one of the most difficult challenges to overcome throughout any given day. There are a lot of factors at play, including how you slept, what you’ve eaten, how much caffeine you’ve had, and even the temperature of your environment. We’ve all experienced that moment at work when your energy dips unexpectedly and even the simplest tasks seems herculean. For many of us, these energy dips can become a regular occurrence, which is why I’ve developed a few simple strategies to keep my energy up as much as possible throughout the day. 

Exercise is the cornerstone of my energy management strategy. I’ve come to realize that periodic exercise helps smooth out the peaks and valleys of my energy levels throughout the day and generally provides me with a more positive outlook on life. Choosing the right time to exercise is up to every individual, but I find that mid-day exercise works the best for me. Instead of going out to eat for lunch, I usually prefer to go for a run, swim a few laps at the pool, attend a yoga class, or hit the free weights at the gym. I eat lunch immediately afterwards, usually on the way to somewhere else. (Yes, I eat quickly.) I return to work in the early afternoon with an energy level similar to the one I started the day with. A lot of office cultures frown upon midday workouts (not the Chrysalix culture thankfully), but I’ve always found this to be illogical. My exercise routine takes an equivalent amount of time that others spend going out to lunch, AND it makes me more productive for the rest of the day than I would have been without it. 

  
When it comes to food, I prefer light lunches and healthy snacks throughout the day. Sushi works really well for me because it’s light yet filling. Heavy salads can also do the trick. There is an outstanding BBQ place down the street that I go to every once in a while. They have outstanding ribs, corn bread, & baked bean; however, whenever I indulge, I know my afternoon is going be suboptimal (to say the least). 

Statistically, your brain functions most effectively two hours after you wake up (preferably with a hot cup of coffee in your hand). Figure out your own biorhythms throughout the day and determine at which tasks you’re most effective at which times. For example, I can do my most effective isolated work in the mornings, such as writing, developing presentations, number crunching in Excel, and reading/evaluating technical reports. In the afternoons, I’m more effective at interactive tasks, at answering short emails, leading meetings, engaging in discussions, and networking. In the past, I wasted a lot of energy forcing morning tasks into the afternoon, and vice versa. 

Inevitably, I do find myself slumping every so often. When I do, another tactic I use is to switch locations. Even picking up my laptop and moving into a conference room sometimes does the trick. If I need something more extreme, I’ll run over to a nearby coffee shop. Oddly, sometimes I find myself able to concentrate better in busy, distracting places. It’s as if my mind overcompensates to subdue the external stimuli. It’s worth a try in the event you get stuck. 

Often times, the big tasks can feel impossible when you’re in a slump. My advice would be to start small. Knock off some of the smaller tasks on your ToDo list, even if they are not as important as the big tasks. These small wins can supply you with the momentum to tackle larger ones. Plus, it just feels good to see that ToDo list shorten, even if it’s the easier tasks that are eliminated first. 

Managing your energy will help you perform at your best and make the most of every hour in the day. 

AVOIDING WASTED TIME 

Up until this point, I’ve talked most about things your should do. Now, I’d like to focus on what you should NOT do. 

Don’t sort your email. I always gasp when I see the multitude of folders people maintain in their Outlook inbox. It makes me wonder how much time people spend sorting their mail into these various folders. I used to do it myself, and I’d say it easily cheated me out of 30 minutes everyday, especially when you count not only the filing process itself, but the distraction of the switching tasks in order to sort new mail as it comes in. Over the course of a year, that 30 minutes per day can add up to 125 hours per year. Think of what you could accomplish in that time. Instead, I suggest leaving everything in your inbox and just search for things when you need them, just like Evernote. 

Don’t put up with conversational tyrants. I’m a nice guy, sometimes too nice, or so I’ve been told. My parents always taught me that interrupting someone when they’re speaking is rude. That said, we’ve all been cornered by a bloviating individual that hardly lets you get a word in edgewise. I’ve come to the conclusion that cutting people off is oftentimes necessary and sometimes it is even appreciated. Most people don’t want come across as boring or annoying, so they will ultimately appreciate it if you interrupt their soliloquy and respectfully redirect the conversation to achieve the goal set out at the onset of the conversation. Time is too precious, cut people off. 

Don’t say “Yes" to everything. VCs are notorious for saying “No.“ At Chrysalix, we see over 1000 deals per year and typically will invest in only 2-3. It’s the nature of the business. That said, I’ve always been a Yes person. Another way of saying it is that I’ve proactively trained myself to have a bias for Yes. If someone invites me to an event or asks for my advice, I’m always inclined to say Yes. The problem becomes when you have too many potential obligations and it becomes impossible to say Yes to everything. For this reason, I’ve had to switch my default response to No. Don’t get me wrong, I still say Yes to many things, but only after I’ve given it some serious thought and prioritized it relative to my other goals and responsibilities. This can be painful but necessary to protect your most valuable resource, your time. 

I hope this helps folks who are similarly driven to increase their productivity. By being more effective at work, it allows to be more successful in both our careers and in our personal lives.