Profile

Jason Pressman

Jason Pressman focuses on investment opportunities in the technology-enabled services and software sectors for Shasta Ventures. Prior to joining Shasta Ventures, he was the fourth employee at Walmart.com, a venture-backed start-up where he was vice president of strategy, business development and operations. In that role, Jason helped build the business into one of the leading commerce sites on the web.

Prior to Walmart.com, Jason served as an associate at Selby Venture Partners where he focused on services and software investments. Previously, he was an analyst and associate at Alex. Brown in investment banking where he advised venture-backed start-ups on financings and merger and acquisitions.

Education:

  • M.B.A., Stanford Graduate School of Business
  • B.S., Finance, University of Maryland.

Areas of Special Interest

  • advertising
  • casual gaming
  • SaaS
  • systems management

Why I Love Working With Entrepreneurs

I respect how much entrepreneurs have to bob, weave and iterate to stay in the game. They have to operate in environments of high ambiguity. Successful people recognize that luck is a gate that opens opportunity, and I enjoy being part of that pursuit. I think what I love most about this job is how collaborative it is. Start-ups tend to be free of politics, which is so refreshing. Everyone is just focused on making the company win.

When I meet with entrepreneurs for the first time I want to hear about the opportunity they’re pursuing and why, what their unique insight is and how they’re addressing a real need or a problem. What’s a real problem? That’s the art of this business. It’s not science for sure. It’s not always obvious.

I also want to hear how they think about the challenges that they’re facing or are going to face, not to see if they know the answers—no one has the right answers at this stage of the game—but to see how they think about things.

Entrepreneurial teams have a fierce hunger to build something, to make something different, to solve a problem, to change the world. They have a drive and a passion to go beyond. I have always loved building things and solving problems. In high school I was on the tech crew for the drama productions, building sets, doing the lighting, figuring all that out. When I was part of the start-up team at Walmart.com in 2000, there was no playbook for how we should build that business, and yet we figured it out enough to grow revenues by over 100% per year for five years.

How We Work at Shasta

Shasta is an extremely customer-focused firm. What that means is that we invest in companies that have a maniacal, relentless focus on their customers and fundamentally believe that a deep customer orientation is what creates a competitive advantage.

At Shasta we view entrepreneurs as our customers and that means that we work really hard for our portfolio companies in a collaborative manner. We truly strive to be honest, transparent, responsive and respectful in all of our interactions with all entrepreneurs, whether we’ve invested in them or not. And we work extra hard with our portfolio companies on strategic planning, recruiting, business development and just being there for them when they need a thought partner. That’s truly the essence of Shasta.

I love the energy and the passion of entrepreneurs and I love having the opportunity to help them solve problems in real time. You make mistakes but you course correct. The CEOs of the companies where I sit on the board call me at all times of the day and night to talk about everything from strategic issues to tactical ones like recruiting for a certain position. I like helping evaluate what’s not working and how you can improve it and make it better. I love making progress against things, and at start-ups the progress is always measurable.

For me this job is about working hard for the companies in our portfolio—whether it’s my investment or one of my partner’s—and being collaborative in that process. I hate losing. I’m kind of a like a duck. Calm on the exterior but paddling like crazy underneath.

Some Things You May Not Know About Me

  • I can’t think of a better way to spend my free time than scuba diving with sharks. They are probably the most incredible and most misunderstood animals in the world.
  • Given that, it might not surprise you that I have 700 gallons of saltwater fish tanks in my house that I designed and helped build. I probably have 50 fish, not including the coral and hermit crabs.
  • I managed a movie theater to put myself through college. My favorite movie from that period of my life would have to be Point Break (I know it was cheesy but something just drew me to it).

Title

  • Managing Director

Expertise

Consumer Services
Ecommerce
Software

Contact Info

"This job is about working hard for our portfolio companies."

Current Investments

Selected Prior Investments


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