SPEAKERS

Dan Portillo, Managing Partner & Founder @ Sweat Equity Ventures

Dan is a former Talent Partner @ Greylock. Previously, he was VP of Success & Engagement at Rypple, and VP of Organizational Development at Mozilla, creators of Firefox. Earlier in his career Dan spent a decade building out successful early-stage, venture-backed consumer and enterprise companies. Dan also served as a Council member for Code2040.org, a non-profit creating opportunities for underrepresented minorities in tech.

"I always ask, how can I help? How can I help with whatever it is that you're doing right now? What are you trying to learn? Who are you trying to connect with? And so, can I help you?"

- Dan Portillo

Jim Cook, CFO @ Orbital Insight

Jim is a hands on strategic and operating executive (COO/CFO) whose wheelhouse is creating and aligning a company's strategic plan to proper operational structures and execution with an intense focus on building great cultures and great teams.

Jim's passion is sharing his 30+ years of experience in scaling some of Silicon Valley's most iconic brands from their foundations to billion dollar valuations (Intuit, Netflix, Mozilla). He was one of the first finance hires at Intuit. He was one of the original six founding members at Netflix. He also launched the Bench Board Executive Network, which is a leadership network and knowledge sharing network for operational executives.

In 2019, Jim joined Orbital Insight, the leading Geospatial Analytics company backed by Sequoia and GV and several other top tier VC's.

"And the most successful people in Silicon Valley, if you really look at them... across the spectrum... are successful BECAUSE of how they help others. Not because of how rich they are. Or who they funded."

- Jim Cook

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Show Notes

• Early career lessons on people, relationships, & “giving” (2:24)
• Vulnerability & the impact of lowering your guard (8:37)
• Building authentic relationships & trust long-term (12:55)
• Breaking down power dynamics & building up “relationship credits” (14:49)
• Learning from mistakes, burning bridges & removing your ego (19:38)
• Tactics for effective relationship building & networking (24:27)
• How to prepare for an important introduction (28:24)
• How to balance your priorities & invest time to help others (29:21)

Transcript

Early career lessons on people, relationships, & “giving”

Dan Portillo: Wonderful. How are you doing Jim? Long time.

Jim Cook: Good. Dan, how are you?

Dan Portillo: We didn't mention that.... So, so I've known Jim for, I guess it's got to be becoming on 18 years?

So we joined Mozilla. He was one of the few people that was at Mozilla before I was. In Mozilla was about 20 people. And Jim was, was already there.

And I would say that there's two people that have had the most profound impact on my career. And it's Jim and John Lilly, who is the CEO of Mozilla and my partner at Greylock. And a lot of like learning how to be an executive, I learned from Jim, so grateful to get to, to get, to spend time with him on this one.

We had a conversation about this, about the foundations of network. And I don't really consider myself a networker. I don't... I know I am a bit of an introvert. I don't like going to conferences and walking around and talking to big groups of people. A lot of the focus has always been on individual relationships.

And we talked a lot about the foundation of like, how do you build relationships? And so, Jim I wanted to just ask you of like... what are the lessons that you learned from like Netflix or earlier in your career and that how that transition to how you work with companies now and how you work with people and individuals?

Jim Cook: Yeah, no, thanks. And Dan, I just wanted to say thank you. For inviting me here and thanks to ELC.

But you know, all of us, we were introduced as experts at this right. Experts at networking. And I kind of took a deep breath and said, "Well, I haven't always been an expert. In fact, I didn't know how to do this relationship thing when I first started out."

And I will say that I'm still working on it. And so I think that's important is that relationships are... for me, it's all about relationships. And I learned from everyone I interact with and including you Dan. So, thanks. Cause I've watched you do what you do.

I too, believe it or not... am also an introvert to an extent but I've learned to be more of an extrovert.

And so I think, just what I've learned and what, just keeps reminding me is that relationships come first. Right.

You can't do anything... And it's weird to say that from a CFO seat. But relationships have to come first because relationships are the foundation of trust. And without trust, you really can't do anything in your personal life or business.

So I'll pause there and that's kind of the theme of where I've come at it. And relationships have to do with being vulnerable. And that's a weird thing coming from a CFO and from an introvert. It's hard to be vulnerable. But it's hard just to be casual and to share as much as you can, without any expectations of getting something back.

And when you can do that it's amazing the power that you get from that because people want to help you. If you help them, they want to help you.

Dan Portillo: I would say like there's for... if you remember nothing from this, go buy Adam Grant's book, "Give And Take." Cause it really is a foundational book on realizing, how do you build and maintain relationships over time?

I think I started my career in recruiting as I mentioned, joined Mozilla when it was about roughly 20 people. I think for most of that time, a lot of the interactions were, were fairly transactional. Of like, when you're looking to recruit someone you're both selling and evaluating.

And I know everyone's having a hell of a time recruiting right now, but it, and we would go that. And I do a reasonable job of connecting with people, but it was still a transaction of trying to figure out if they were going to be a good person for Mozilla or one of the companies that we're working for.

And the transition for me really happened as I went to Greylock and moved into venture where I have probably met and interacted one-on-one with at least 30 new people a week for the past 10 years.

And so I had a pretty big network going into Greylock from my time at Mozilla. But within one year, like it doubled. And within two years, it doubled again and created this really like exponential growth and connection.

And to this day, like I'll have people that I talked to years ago, that'll say like, "Hey, it's like, you were amazing at helping me with X, Y, and Z."

And I don't remember that conversation, but like the mechanics of actually connecting with someone that you're meeting new of how to like, not make it feel transactional was w was like massively impactful.

And Jim, I'd love to ask how you approach things. But I have... whenever I meet someone new, whenever go meeting, I'll go look at their LinkedIn, I'll look who we know in common, I'll look at where they worked. And I usually, before we even get into introductions, we end up in like a bit of like a dialogue and conversation that's very kind of social. And then I usually have to wait like, wait, wait, wait, spend five minutes. Like we should probably actually do like the formal introductions, give our backgrounds.

And so the ability, like the faster you can connect in the beginning of a conversation with someone, the more it kind of disarms the conversation allows you to learn a lot more.

And so to this day, I go without a lot of intent. Like when I'm talking to someone. There's usually... maybe I want them to be a customer for one of our portfolio companies and maybe I want them to join one of our portfolio companies.

But my focus is always on learning as much as I can about the individual. And, I'll preface things with like "I may or may not have something that's interesting for you today or tomorrow or five years from now, but before I kind of like pitch you on something or share something with you, I really want to know about you and what makes you tick and what you're interested in, because what I was going to suggest may make no sense at all, or like may not be relevant at all."

And I think for people that are actively recruiting right... like there are certain things that you can do. And that I do with, with individuals say you know, "here's a lot, I'm like, I will do my best to educate you on my company or what you want to do. Like fundamentally, I think you should make the right decision. And I'm happy to introduce you either to people that I've worked with in the past or other companies or other venture capital firms because what we have may not be right for you."

And so I think if you're able to connect with people on having their interest or feeling like having them feel like they have their interests in mind, they will like lower their guard a bit and help you. And then allow you to build a better connection. So you can then kind of pitch them on what you're living, what you're doing.

So I'll stop there cause I've been blathering for way too long.

Vulnerability & the impact of lowering your guard

Dan Portillo: But back to my original question, Jim, like as you're now meeting new people for, when you meet someone for the first time, how do you actually structure that?

Jim Cook: I do it very similarly, the way that you just described and you kind of had me with the word that you just use lower your guard. Cause as you said, those words, I thought to myself, wow. I have had to unlearn many of my past biases.

You know, I come from the finance world. You know, when I started work 30 years ago, it was some people were in ties and business shirts. And in my world, you know, everything was about being professional, being credible. And, and to have your guard up right.

And what Dan is talking about is, especially in Silicon valley and somewhat unique to Silicon Valley is this concept of letting your guard down first. Connecting first and then getting to business.

And I've had to learn this and continue to remind myself... and I've gotten a lot better at it, but, and I've watched people do this very successful people.

So the tip and trick I would give everybody is to see who does it really well in your own networks at your own companies, at events. And copy from the best. Look for pattern matches of what they're doing to connect with people, if you're not as good at it. That's what I did.

I was like, "Oh, you know, that CMO of marketing or my CEO, how did they do that? How did they connect with people?"

And you can look for patterns and you can practice them. It's like anything else, you almost have to practice them. And the one practice is letting your guard down.

I remember when I first got to Silicon Valley Bank. I didn't work Silicon Valley Bank. But as a client... I didn't understand how they operated, but, over the years I realized they operated with this relationship first.

They would invite me to events and I thought I was going to get this big pitch, use the bank, do this, do that. No! They would literally get up on stage and say, we just gathered everybody here together cause you guys were all cool. And magic is going to happen here and we have no agenda.

And I was like, "What the heck's going on?"

And I realized that that's kind of how Silicon Valley works. And I've used that as an example because they continue to do that and they go relationships first and they just know that they can mold that into what needs to happen once people can let their guard down and trust each other. So you had me at let your guard down Dan, so that was

Dan Portillo: Yeah, I think it's, it's a little bit daunting to get used to just like talking to people and striking up a conversation. And I think a lot of what I've picked up over the years is to basically like I have a very like particular tactic or not tactics.

So if I'm meeting like a new founder, I'll focus a lot on like my background more as a sense of like, "here's a set of stuff I've done that's been like valuable and like, I'm happy to talk about my time like working with the White House, the USPS, or like getting started at Mozilla. Or like when was it early at Greylock and helping them out. To the extent of where you are and how can I help you in any particular way?"

Actually, I don't talk much about what I'm doing with Sweat Equity now, especially with founders. And I have them like tease that out instead of like you. That so like really focusing on the set of things that are hopefully most valuable to that individual. So that you can then provide some sort of awareness or education or something directly to that individual. And we all have things in our expertise and background that we can do.

And then one of the things that I talked to Jim about was earlier in my career, everyone that I spoke to was more valuable, like that interaction was way more valuable to me, than it was to them.

And at some point in your career, like that value will shift. Like, will switch. Where like your interaction with them is more valuable than their interaction to you.

And, what I would then recommend is like, some people kind of turn into jerks at that point and stop interacting with other people or, or people that they view as being beneath them, which is a colossal mistake.

And so part of what you really want to do is continue to invest in, not just the people that knew more than you. But the people that are kind of coming up. Because you never know when that intern is the new CEO of like some massive company in the future.

Building authentic relationships & trust long-term

Dan Portillo: I guess I wanted to ask you like Jim... how do you view building like the authentic relationships and, and trust like over time. And the, and so we've had, I mean, we've known each other for 18 years, but how have you kind of focused on building that skill?

Jim Cook: Yeah, I love how we kind of think in the same terms and finish each other's conversations. My own personal litmus test is exactly what you just described. Which is the more experienced you get... And I think we have a bunch of engineering managers on this call...

The more successful you get as an engineering manager, or any walk of life, the more there's a disconnect between those coming up, like the interns you said. And the more successful you are, the more gap you're creating. In this, "Oh wow. It's Dan Portillo"

And I've had this.... and it really embarrasses me cause I'm from the Mid-west like, "Oh Jim! Yeah. You're from Intuit. You're from Netflix. It's like, I don't want to ask you this question."

So you have to work harder and harder at breaking that barrier because people have these biases going into the conversation.

Like, look, I'm just Jim Cook. I eat chips and salsa like everybody else. Right. I spill it on my shirt like everybody else.

So work at that to make it a safe space for those people who may be intimidated by the conversation because it's only then that you can get to that authentic conversation and help each other out. Right. If they're so in awe of you, they're not going to get to the real question.

And on the other side, my own personal litmus test for those assholes is who have made it, who don't want to give you the time of day is... it's your choice whether you want to engage with those folks as well.

And I would probably say it's probably not worth the time and effort to engage. There's plenty of folks who aren't like that, who want to have those real relationships.

So, yeah. I'm not sure I would spend a lot... I personally don't spend a lot of time with those folks. Even though they are so much more successful than I am.

Breaking down power dynamics & building up “relationship credits”

Dan Portillo: Yeah, I think that there's a couple, like... for a lot of folks right now, they're probably interviewing a lot of candidates. And so a lot of people will try and focus on that power dynamic. And so how do you break it so it does not feel like a power dynamic with the interview?

If you're interviewing them, like someone that's trying to come to your company. So you're able to now get into the technical questions in the evaluation, everything you would do there.

There's this one thing that I learned from John Lilly, which is like the question that he would always ask, that I've since adopted, which is... I always ask, like, how can I help? Like how can I help with whatever it is that you're doing right now? And so, or what you're like, what are you trying to learn? Who are you trying to connect with? And so can I help you?

And so I think over the decades, I have built up a bunch of credits with people that I've helped, so that at some point if I ever need to like cash them in... I can.

and Jim has like infinite credits with me... for the amount of time that you've helped me over the years.

Jim Cook: Vice versa. I love the concept of credits, right? I love this concept of just help first.

I think my mom always used to say, you know, if "whatever you give back to the world, you'll get back three times in return."

And she's she was right. I think she told me that when I was six years old and I still remember it.

And so I think this is why Dan and I and others get along because you kind of go with help. And the more successful you get, obviously the more you can help cause the more, you know, and the more people, you know.

And the most successful people in Silicon Valley, if you really look at them, across the spectrum, are successful because of how they help others. Not because of how rich they are. Or who they funded.

There are several examples of people who funded companies. Who are just, and I'm gonna use the word again, "assholes". Who aren't really successful in the Silicon Valley because no one wants to do anything, have anything to do with them.

And there are others example, people who maybe haven't made it all the way, or they're not, you know, not, not from an income standpoint we're just like, man, that person's successful. They just, every time I turned to them, they helped me.

And so I think that's so important.

Learning from mistakes, burning bridges & removing your ego

Dan Portillo: I think having valuable interactions with people... so it's not like you have to send someone a Christmas card or holiday card, or like, know their birthday or, have a calendar where you reach out like every quarter. Like that's actually not really required.

Like, what really matters is to have that when you do interact, that it's a very high-quality interaction. And that like one, you're helpful;. Two, you actually have a meaningful conversation that they hopefully remember. So, you know, you come back a year later or two years later that they're willing to take the call again.

A lot of that I think has come like over the years of learning how to just interact authentically with, with someone and to take an active interest in them, in a human and the set of things that make them tick.

And I'll try and do some tactical things as well of... like one other question that I always use is like, "Look, I've read your LinkedIn profile. But I always like to hear people's story. Tell me the whole story. Like, tell me you got here. Like, where were you alone? When I first started, I went to blah, blah, blah school. And you're like, now, where were you born? Like, where did you grow up?"

And then asking like really good questions about what they've done in the past and really getting to figure out like, which were those, those moments or those career moments that that had the most impact on you.

And I think there's some interesting things that you can do around mistakes that you've made or, or things that you got wrong and how you got them wrong.

And Jim, I don't know if you have any examples, or I don't mean to put you on the spot of like, like a clear mistake or like this learning moment that, that shows like some vulnerability that you're able to kind of share with people that you're coaching or working with.

Jim Cook: So, first of all, I believe that, you know, you don't move forward unless you make a ton of mistakes and I've made a ton of mistakes. And I think one of the biggest mistakes I've made just in a meta sense, is this concept of burning bridges.

And Dan, you and I have talked about this. Like the more you get connected to people by definition, not all these conversations are going to be positive. The more you deal with people and the more like you're going to have differences of opinions.

When you have differences of opinions or someone pisses you off because even though when you get to friendships, right... business colleagues aren't necessarily friendships, but you know, we're humans, we have emotions. And don't let those emotions get in a way of the relationships.

So the mistakes that I've made are, in a couple of instances I have let my emotions and my ego get in the way and. And told the person or, or told other people, you know, about this one instance, which clouded the whole relationship. Which wasn't fair to me, it wasn't fair to them. And I've learned never to do that again. Because the valley is small. And the benefits far outweigh, any pain points you might have with that person.And stay connected.

Because like anything else, everybody only shoots eight out of 10 shots on goal. I'm going to piss people off two out of 10 times. So is every one of my connections. That's not the point.

So yeah, I've made that mistake personally. And I would just encourage people to not burn bridges because anyway, I know Dan, you have a lot to say on that.

Dan Portillo: Yeah. I mean, I think it's, it's very easy to like, get... If you're upset to like hit the nuclear button and like really like tell someone off or... and it's not that you shouldn't have standards or morals or, and definitely, you should speak up when you see something wrong.

But I would say aside from my family, like the thing that I value most is my reputation. And so, and I guard that with, with my life. And that no matter to the interaction, whether it's with a portfolio company or a candidate, or just a random person that I'm meeting. That focus on always being above board, Always doing my best to do the right thing and acting with integrity, is like the single best way to have a network that values you and will support you and do good things for you. If you're like, they know that like you, that you're willing to do the same.

Jim Cook: Yeah. I mean, it's about aligning interest and, and really comes back to trust for me. I mean, we started this conversation with trust. But everything you're talking about is building and maintaining trust. And if you build that foundation, then you can get commitments from people. And when you can get commitments from people, then you can actually do some great things. Right. And so, but you can't get commitments from people if they don't trust you or they want to do something for you.

And so people skip the relationship thing a lot, but it's almost like the foundation of your house, if you don't have it, you're not going to be that successful in building your networks

Tactics for effective relationship building & networking

Dan Portillo: Any technical things on your side? Like, how do you bring like your, and now you do a lot of coaching with like CFOs CEOs... and imagine like for coaching to work effectively, the relationship really has to be good, like from, from the get-go.

Any specific tactics that like you from coaching world that you would use or that you could recommend other people could use and as they're, as they're building relationships with people?

Jim Cook: Well, first of all, build relationships one-on-one using the techniques we described.

But a really great tactic is to be the glue for helping them create their own networks as well. So once you get good at understanding that the power of the network is everything, then ask permission to bring the one-on-one people you're having a relationship with to "would you mind if I introduce you to somebody else and let's have a group conversation here."

Because here's the thing... having group conversations is way more powerful than having one-on-one conversations. And everyone seems to me, at least the pattern matching I've done... is so appreciative when you can expand their network with your network and vice versa.

And so always remembering that you've got other people that are smarter than you and saying, why don't we bring this person in the conversation, that person conversation, guess what? Next time you have a conversation one-on-one, to go the back to the one-on-one thing... they're going to remember that you're always bringing somebody else to the conversation and how valuable that connection is.

So I guess that's the tip or trick for me. It's not always one-on-one it's how can everyone help everyone? Right.

Dan Portillo: Yeah, I would say like other tactically, it was like just interact with, not that certain people are low quality, but just be very deliberate about who you spend time with and who you help and connect. Right.

So there's, I want to be very open with my network. But I want to make sure that that person is the right person to give that connection to.

And so like, you know, Jim and I worked with the now CTO of Facebook, like Schroep, we've known him for 20 years. It's like, there's plenty of people that say like, "Hey, can I get an intro to Schroep?"

But like, you want to be very selective. That doesn't mean you just do anything everyone asks like you just have to be selective in how you apply that. Because a good way to burn your network is to make kind of bullshit introductions that like waste other people's time.

So there's that another tactical thing that I would say is like respect other people's time. That means not having to have conversations go way longer. Not taking up their time with like weak asks. like introduce them to like to people that are probably shouldn't get that level of introduction. And to be just respectful that they're willing to like spend time with you.

And that doesn't necessarily have to be more senior people that could be even candidates that you're interviewing. It'd be like, Hey, they're their time is a gift. And they're kind of giving it to you. And to always be respectful of that.

Jim Cook: Yeah, I totally resonate with that, Dan. And what I resonate with that is... It's almost like the empathy question of make sure that when you're introducing people in your network, what's in it for them as well. Should be in the back of your mind and be very open and honest about that on both sides. I think just in general, I think a lot of times I tell people, "Yeah, I'm not sure that's a good idea to introduce with, can I get an introduction to John Lilly" or whatever.

And it's like, well, I'm not really sure you're at that stage yet. And I'm very upfront with like, "I, you know, I like to respect John's time.So until we get this to a certain stage that he can do something with, I'm going to hold off on the introduction."

I just tell them that

Dan Portillo: Yeah. Well, I think it's like, you're not ready for that intro yet.

Like I haven't done, I've done it, definitely done that with it. And then Patrick, you're welcome to come back for, for Q&A.

But I've definitely had that conversation of "you get one shot at this conversation. And so you need to be ready when you have it, that you could actually kind of take full advantage of it. So like, you should probably go and practice with like a few more people before, before you go and have that."

How to prepare for an important introduction

Patrick Gallagher: That was an incredible point is I think it's really hard to tell people no for an introduction or I find that I tend to avoid even responding to something like that.

How do you get people to prepare for that conversation, Dan? You say you've got one shot? What's the coaching you give people to help them get the most out of that shot?

Dan Portillo: Yeah, if you're like... it happens a lot with like fundraising... someone's like getting their company started and like, they want to get that first customer. Or they want to go and talk to like a particular investor.

I'd be like, "You need to practice your pitch or like go practice with like these three investors of like investors in air quotes over here before you go, like for the big one, like, you need to have like your knives sharpened or like let's practice your pitch or whatever it may be." ...

Patrick Gallagher: Okay.

Dan Portillo: ...before you make that introduction. Because I, if I make an introduction and it goes poorly, like that reflects on me. And so I want to be very cautious of doing that.

Patrick Gallagher: Awesome. Thank you.

How to balance your priorities & invest time to help others

Patrick Gallagher: So we had one question that came in was how do you prioritize helping others while still maintaining focus on what you need to do for yourself and your business? Jim, do you have any thoughts or Dan about how to make that balance?

Jim Cook: You know, honestly, it's just a conscious time management effort. It's almost like anything else on your calendar. If you don't make time for it, it won't happen. So you almost have to consciously make time to... back to my example of I have a note post-it notes. Can this be a group network event versus a one-on-one coach?

I do a lot of the same modules over and over again. And I have, I have to remind myself, "I think more than one person needs to hear this. Let's turn this into a panel talk because it seems to be a pattern match."

But then you have to make time to remember to ask yourself that question and actually calendarize

Dan Portillo: I probably have between 50 and 60 meetings a week. Like, I think I did almost 70 meetings one week. It was... that one of them almost broke me. And so I do spend a lot of time. But I also am like very cognizant of looking at my calendar and of those meetings like how many, like, were any of them not a good use of my time?

And so I think I've now kind of trained myself that Yes, I'm going to meet a lot of people. But it always has to be a pretty good use of my time.

And there's varying degrees of help that you can offer. And so there are certain things that you can do by just making an email introduction or like that doesn't require that much amount of time, but creates a huge amount of value.

So you have to be like... if something's like a really heavy lift like that it needs to be well worth it. Right. That, that you're like, all right. And then, and then you would make them aware of it. Like, "Look, that is, that is not an easy ask. And so it might take awhile."

But you know, the more you can do, like via email or, or provide value in seconds versus minutes or hours is ideal. I mean, like granted to be fair, like I've now I've been working since like the web van days of the internet. So I got started in 99 and just like the benefit of being here and for so long just makes it very easy to go and do that.

So people that are early in their career, they don't have that same... Or if they're in a job that doesn't touch as many people as mine does. But like figuring out the opportunity to like, we're going to have dedicated time to be able to make new connections. And like start with the people that are already around you. And then start to expand from there.

Jim Cook: I'll add a very pertinent example on Reid Hoffman. I would encourage everybody to search or Google search "How To Interact With Me" by Reid Hoffman. You'll find it. I don't know how to search that word... but he's got a great article about how you need to interact with Reid.

And it starts with... make sure you know what you want and what you're asking for and how I fit into the equation. You have to be very deliberate about that.

So search that out. It's a great article. That's what Dan's talking about.

Patrick Gallagher: That sounds like a really powerful framework just to carry into almost any conversation for folks. Is doing that due diligence ahead of time. That can be a great way to help make sure it's a really good use of your time.

Jim Cook: Know what you want. Know what the next step is.

Patrick Gallagher: That's great. Wow.

Dan, Jim, thank you both so much. That's all the time we have for questions, but thank you so much for sharing your perspective, your practices, your life stories. And I think the frameworks to allow people to build really rich relationships that open up opportunities and impact within their communities and their relationships.

So thank you both so much for your time and insights.

Dan Portillo: Thank you for having me.

Jim Cook: Thank you all.