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Why This Entrepreneur Met With 2,000 People in Two Years

Morgan Lichtenstein
4 min read

Brian Schwartz, founder and CEO of SIZE Advisory Group, shares how he transitioned from the corporate world to entrepreneurship, why he set out to meet with nearly 2,000 people over a two year time period, and other business insights. 

About Brian Brian leads SIZE Advisory Group, a consulting group that helps high-growth companies scale quickly. Brian received his master's degree in finance from the London School of Economics. He's held leadership roles in organizations such as Expedia and DreamWorks Animation, and spent the last several years as an entrepreneurial executive. As a Hunt Club Expert, Brian even referred Kurt to his current role at the company!

The following interview has been edited for brevity and clarity. 

2,000 Meetings in Two Years

Q: You have a reputation for curating a world-class network and community. What's your secret? 

A: When I decided to move on from my role with Expedia, I talked to Neil Golden (former Chief Marketing Officer at McDonald's) because I was trying to figure out what was next in my life. His advice was to meet 300 people with no intentions, and from those meetings, I'll figure out what to do next. I took it to heart, and in the past two years I've met almost 2,000 people with no intentions. 

Through these conversations, I found I was able to quickly provide advice and guidance on business challenges, and I had solutions to help solve those problems and connect the dots. 

I also found I could identify who individuals should connect with. I’ve done a really good job at identifying what someone is looking for and connecting them with those individuals to create a mutually beneficial relationship. I always try to make sure that both people are going to come back and say, “I'm so thankful that Brian made that connection.” 

Q: How are you able to connect so many people? 

I’ve come to realize that when people actually do what they say, others are mesmerized by that. For example if I tell you that I am going to make 15 connections for you, I am going to make 15 connections for you. If I say I am going to send your deal to 100 investors, I'm going to send it to 100 investors. 

I believe that you should do what you say you’re going to do. For me, my reputation is  most important. I want to make sure that everyone I connect with has positive things to say because this is a long haul. Life is a journey and you never know who you’re going to meet along the way. 

Q: Of the 2,000 people you’ve met, who do you admire and want to emulate? 

A: I am humbled and fortunate to meet a lot of amazing people. One person who comes to mind is Richelle Parham. She is on the board of directors at Best Buy, e.l.f. Cosmetics and LabCorp, was the chief marketing officer at eBay and she’s a partner at WestRiver Group, a venture capital fund. 

I admire her because she's accomplished so much in her career and is involved in many different projects and organizations. I use her as an example of someone who has successfully transitioned from a corporate executive role to having their hands in multiple things, and adding tremendous value.

Making the Move From Corporate Jobs to Entrepreneurship

Q: Prior to Expedia, you were at DreamWorks Animation for six years. What was one of the core values at DreamWorks that stuck with you?

A: Jeffrey Katzenberg (co-founder and former CEO of DreamWorks) was really strong when it came to transparency. He used to blog every day on the activities happening at the studio, and was very candid and open. At that stage in my career, being exposed to that was valuable. 

Also, DreamWorks is focused on community and people. It's a very tight group of folks who continue to stay close. To this day, most folks at DreamWorks are very close friends.

Q: How did you evolve your career from the corporate world to one of entrepreneur and operator?  

A: Following DreamWorks, I worked in private equity and venture capital. Through these experiences, I met a lot of people like me who were advising and consulting, but each advisor was limited to their functional lane. For example, HR consults on HR, finance advises on finance, etc. I wanted to bring together a dream team that could add more value to the companies collectively than individually, across many functional areas. We haven't formally launched yet, but we're already advising 14 companies. 

Q: You’re advising for some high-profile companies. Tell us about that. 

A: We’re focused on growth-stage companies doing $10 million plus in revenue between series A to C. We have learned how to quickly uncover the one or two most pivotal issues for our clients, and come in to help solve for those issues. 

One example is a growth-stage B2B company in the software sector based here in Los Angeles. We started working with them on branding and marketing, and then rolled into business development (we loaded their pipeline with 50+ new companies). Now, we’re helping them raise a significant amount of growth capital. From there, we’re hoping to roll into HR to help with organizational development and building their team. 


Why Cultural Fit Is Most Important

Q: What are the qualities that you look for during the interviewing and hiring process?

A: For me, cultural fit is most important. Everything else comes after that, right? At the core, you want to make sure the candidate is qualified enough to interview for the role, but you are trying to assess the right cultural fit.  

Q: What were some of the ways that you’ve seen organizations build successful cultures?

A: The digital convenience store GoPuff has done this really well. Following a Series B, their lead investor said, “Stop what you are doing and take 30 days to figure out your culture.” This included digging into who they hire, why team members come into work each day and who they want to work with. It's important to take the time to develop the culture in order to be able to recruit and retain the right talent. 

I also encourage founders to play a role in the final interview process for all full-time employees. Their involvement shows dedication to the talent and culture.  

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