#27 James Orsini, COO of VaynerMedia, on Launching New Divisions, Operating & Scaling a Global Digital Agency & What It Really Takes to Execute Garyvee’s Vision

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*It’s officially been a year since I left VaynerMedia: here are my Top 5 Tips for New Entrepreneurs based on the very real lessons I learned. It also includes a free Business Checklist for New Entrepreneurs that I made in partnership with my attorney Nico Becerra (Ep. #14).

I feel particularly passionate about this topic because most entrepreneurial content online is motivational and not about what you genuinely need to do in order to create a legitimate business. That’s why Nico and I are working to provide you with valuable resources to make sure, if entrepreneurship is actually the right path for you, you can set yourself up for success right out the gate.

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“Ideas are shi*t, execution is the game.” -@garyvee

Big ideas aren’t enough to sustain a business. You need executors – James Orsini is an executor.

This week’s interview is with VaynerMedia’s Chief Operating Officer and Gary Vaynerchuk’s #2, James Orsini.

James has more than 30 years of finance and operations experience. He has held high level positions at global agencies like Saatchi & Saatchi & Interbrand. He was a global CFO overseeing 31 offices in 26 countries before he was 30. James has held most C-Suite executive roles from CEO to COO to CFO to CIO (and he’s also a CPA!), which makes him beyond qualified to speak to what makes some of the biggest agencies in the world run successfully.

On this episode, we talk:

  • -His process to bring Garyvee’s business visions to life
  • -What makes a good COO
  • -Scaling a business the right way
  • -How new divisions at VaynerMedia are created
  • -When it’s time for divisions to be dissolved
  • -How VaynerMedia thinks about fees & pricing
  • -Why James is not interested in being a CEO again (& more!)

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SHOW NOTE TIMESTAMPS

3:42 – James’ background before Vayner

6:24 – So you said you were a global CFO before you were 30- how were you able to rise through the ranks so quickly? Can you explain even the difference between the role is as a CEO vs a COO vs a CFO (and which of those is the most stressful)?

8:14 – So when you started at Vayner you came in as Chief Integration Officer. What was your decision to actually join Vayner, and why that role? Did you know that was going to ascend to COO later?

11:10 – How has your day to day role changed in the move from Chief Integration Officer to COO?

12:01 – To give people a little background what is Vayner X?

13:45 – When Gary acquires a “Pure Wow”, do you oversee the operations of “Pure Wow” or does that operate completely independently?

14:42 – Gary and AJ have business experience but not traditional operations experience from the magnitude that you’re used to in advertising. What operating systems were not in place at Vayner that you helped institute?

16:19 – How is Vayner the same as agencies that you’ve worked for and how has it been different?

17:00 – A COO’s responsibilities are so dependent on the CEO you work with, and one of the things I loved about working with Gary is that he’s not a micromanager. I don’t know how your relationship goes in terms of decisions; does every decision need to run through him? Are you allowed to execute on ideas you have or is it him coming to you with ideas and then you just have to execute on those?

18:00 – How has Gary been different from other CEOs? Is it just his vision or has it been something more than that?

20:34 – What makes a great COO?

21:53 – Gary is famous for saying ‘ideas are shit, execution is the game,’ so obviously you have that background. What’s your decision making style then? How do you logic something out? If he comes to you and he’s like, ‘I want to build a Twitch studio tomorrow,’ where do you even start?

23:29 – You’re obviously a financial mind, too. So let’s say he comes to you with an idea, where do you start? Do you start with the financial aspects, do start with trying to understand it as a general business, do you try to understand it as a process that doesn’t maybe exist yet?

25:18 – Because you do have this financial experience I’m sure you’re looking at profit and loss statements. How does your job interact with the CFO world? How do you and Alan work together?

27:23 – So a big part of your role is efficiency. What are the metrics to gauge efficiency? If something is not efficient, where do you start looking to streamline it?

28:12 – So then how do you think about the strategy – in general for growth and expansion, is it usually coming up with new offerings, is it about bringing in more business for the same offerings?

30:55 – We’re definitely going to talk about Vaynermentors, but even just talking about the 4 D’s and other offerings like AI and voice services, how do you guys figure out what to charge? I know with at least the 4D’s you can maybe ballpark like what Gary would get for an hour or whatever, but if you’re implementing a completely new service…?

32:12 – So is that when you decide if you should raise rates?

34:00 – You’ve worked for a ton of companies at this point. What are some of the biggest mistakes you see when people are trying to scale and how can you avoid them?

35:24 – So I know Vayner has the London office and that there’s always been talk about a Singapore office or some kind of Asian hub (who knows if you’d expect the Latin America) —  What are the important elements to look for in terms of global expansion?

36:29 – Speaking of things that might not work, when it comes to divisions of the agency that end up getting dissolved, how do you gauge when it’s time to call it quits?

39:08 – So then what’s the rotation for you on checking in on departments? Like you said, now you have the experience aspect, you have the studios, you have a Vayner Talent, and a Vayner Beta, and all of this stuff happening…

40:37 – What aspects of Culture do you need to take into account? What are you guys having that kind of conversation about?

41:34 – So I’m always interested when Gary introduces a new offering. We touched on it earlier, but I know you’ve been particularly excited about Vaynermentors- can you tell me a little bit more about who this is for?

45:45 – So how much growth can these companies expect, or is there no expectation put on that?

47:02 – I know this is new but how long does it take to really deep dive and truly understand one of these businesses? It seems like it would be very time-consuming.

47:50 – Is there anybody that you look to for business advice, and how do you stay up-to-date on trends?

48:49 – You’ve been really active on social media now- were you active on social media before you joined Vayner?

49:22 – So are you working on building your personal brand? Is that actually a goal of yours or is it more just for fun?

50:30 – What do you think the secret to influence is?

51:55 – You mentioned that social and digital is the last piece that you didn’t have on your resume- what’s the dream for you at this point?

53:07 – You have been the #1 and right now you’re Vaynermedia’s #2- when did you realize you didn’t want to be a #1?

55:53 – Where can people find you?
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To connect with James:

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VaynerMentors Info

To connect with Brittany:

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