Matt Mazzeo: How to ask questions like Chris Sacca

Late Friday night, billionaire venture-capitalist Chris Sacca Periscoped the airing of his guest appearance on ABC’s Shark Tank. Sacca was in good company, with friends and family all around. After the episode aired and ended, a massive 1 hour Q&A session started. Moderating the discussion between the living room panel and Periscope viewers was Matt Mazzeo, Managing Director at Sacca’s firm, Lowercase Capital. I asked Chris Sacca a question in the Periscope chat.

“You’re a fantastic people-hacker. How can we get onto your level?”

I had heard stories of Sacca sneaking into pricey networking events by negotiating in Spanish with the cooks in the back. I marveled at how he graduated from law school by skipping class and throwing a “bring your notes” kegger every semester to get the in-class topics needed to ace finals. I asked this question hoping to learn how to wiggle my way into places where I slightly didn’t belong, or how to change my view of people as immovable obstacles into malleable opportunities.

Mazzeo read the question and turned to Sacca. In his brilliance, Sacca reflected the question back to Mazzeo. “What does that mean to you?”

Empathy & unloaded questions“[Chris is] really amazing at getting at the heart of what of why [founders] are doing what they are doing.”

Mazzeo answered that the core of Chris Sacca’s interpersonal arsenal is a deep understanding of empathy — empathy for founders, empathy for users, empathy for products.

When meeting with founders, Sacca is keen on discovering their motivations through a series of intentionally vague questions. “How do you envision success with this product? What does success look like?” The value in these broad questions, versus “how many users would you like to acquire?” or “how big of an offer would incline you to sell?” is that they allow the founder to fill in the rest of what is unspoken about their future.

It makes sense that by asking open-ended questions that have a multitude of answers, you find unbiased points of view. It’s easy to ask a question that makes a person answer a certain way, even if its a lie. These intentionally vague questions remove any indicator of what the asker wants to hear and allows a shared understanding to unfurl.

While I myself am not anything remotely close to a venture capitalist, I wonder: does understanding the people behind his investments separate Chris Sacca from the rest of the VC world? On the surface, it makes sense for a time-crunched, successful venture capitalist to demand only efficient and quantifiable answers about the company in question. It saves immediate time. But by revealing in the intent of the people behind the company, Sacca is able to save time over years. Founders who would be satisfied with a lifestyle company are fished out immediately. Likewise, founders who want to build an empire, and will relentlessly win are identified early.

What does that mean to you?

As I reviewed the Periscope stream to write this article, I noticed this very same gracefulness in how Sacca asked Mazzeo to answer this question. “What does that mean to you?” I think that finding the answer that someone wants to tell you versus finding the answer that you want to hear is a noble goal, and one that I will aim towards.

Thanks to Chris Sacca for opening up the space for questions, and Matt Mazzeo, thanks for answering mine.

If you missed last night’s #WestCoast Periscope Crew, here is the panel’s Twitter handles.

Chris Sacca | Crystale English-Sacca | Matt Mazzeo | Jesica Ahlberg |

Dick Hillenbrand | Jackson Dahl |

Matt Mazzeo: How to ask questions like Chris Sacca was originally published in Hacker Noon on Medium, where people are continuing the conversation by highlighting and responding to this story.