Jason Shuman

Jason is a Partner at Primary and has been working in NYC as a VC for the past six years. Jason focuses his investing activities on marketplace startups, consumer tech, fintech, proptech, and prosumer acquisition models. 

At Primary, Jason has led investments in Dandy, Lili, Helaina, and Therefore. He also sits on the Board of the consumer real estate data company, Realm.

On his morning routine.

I’m usually up around 6 AM. 

The day starts with journaling. I’ll give myself as long as it takes to clear my head and organize my thoughts, which tends to yield about two pages.

Most mornings I’ll follow that up with a quick meditation using Waking Up.

Increasingly, I’m leaning on meditation to find clarity at the start of my day.

About 3 times a week, depending on how crazy work is, I’ll hit a workout. Once I’m showered and my mind is set, I’ll dive into work: setting up my agenda and running through action items at Primary that require urgent execution.

On triaging workflow.

In the morning, I’ll spend about 30m triaging emails, texts, socials, and Slack.

On MWF I block out a 2 hour period from 9 to 11 AM where I give myself room for flow state. It varies day to day, but it typically entails deep research, writing, and creative outlets. 

I just started working with an executive coach who helped me distill a list of things that energize and drain me.

At the start of every week, I’ll address each activity that drains me.

Then, I’ll quickly remove them from my workflow, which in turn enables me to design an optimal week that only energizes me.

On making mistakes.

Early on in venture, I cut off founders way too much in pitch meetings. It wasn’t intentional, but was a result of my excitement and how fast my mind can work at times.

I learned that I hate when investors cut me off after helping fundraise while operating at Julius. My style has changed since.

I also wasted time not thinking about the most important parts of the business. 

Now, I do my best to distill 2 or 3 things that I “gotta believe” in order for this company to become a billion-dollar company, and try to suss out how the founder thinks about them or wants to approach them tactically. 

Ever since I got into venture, I’ve never been afraid to dig into the tough questions. Those could be about the founder’s upbringing, worst references, bad work experiences, and so on. 

Hard questions and vulnerability help me get comfortable with founders fast...but it doesn’t land with all of them.

On building his reputation.

Reputation in venture is really about genuine connections. I’ve been doing this for 6 years now, and the honest truth is that I had to figure it out on my own.

The most important takeaway has been learning to be vulnerable.

People are human.

The only way we can start connecting as humans is to be vulnerable with one another, instead of putting on this charade that a lot of investors typically do.

You don’t need to act like you know everything and everyone. 

Just be real.

On learning to say no.

You have to hit a breaking point to get better at something.

One way to accelerate that process is by setting goals.

By setting very clear goals around things that you want to achieve in a month, quarter, or year, you can start if you’re on track. From there, it gets easier to say no to the things that don’t help you reach your stated goals. 

It’s also critical that you develop criteria for things you’ll say yes to.

For example, when it comes to investing, I may be looking at 30 to 40 deals a week. But, I’ll typically only dig into a quarter of them based on whether they’re in my sphere of expertise.

If those deals don’t fall within my realm of real estate, fintech, healthcare, or consumer internet, then it’s better to shift those meetings to someone else on the team or pass.

On hiring at Primary.

Our immediate goal is to create a super diverse team. That diversity comes in a lot of strains, including skill set, upbringing, and point of view on the world.

When it came to scaling up our team after the new raise, we started pulling from a rolodex of operators and investors that we’ve always wanted to work with.

We’re looking for the rare mix of high EQ and high IQ hustlers: fiercely curious, intellectually rigorous, and incredible at building relationships with founders.

I look at the best venture funds as being like basketball teams.

Different players play different positions, with different skill sets and they’re all important to have in order to excel.

On his evening routine.

I have a block around 6 PM where I spend about 30 to 60 minutes triaging email and closing out any urgent work.

After that, I’m offline.

At that point, I’ll go out to dinner with friends, listen to a podcast (right now it’s Sam Harris or Tim Ferriss), or just do something more socially stimulating. 

If I’m taking it easy at home, I’ll cook or run through some youtube lessons on photography. Most nights, I’m in bed and lights out around 10:30.