Michelle De Guzman is executive assistant and personal assistant to Gideon Yu (Co-owner and former President of the San Francisco 49ers, and former CFO of Facebook and Youtube).

Michelle De Guzman Leader Assistant Gideon Yu

I really enjoyed my conversation with Michelle and know you will too! Michelle shares the story of her first interview with Gideon, tips on working with a high profile executive (a role that’s not for everyone), and a save-the-day story about Pokemon. Enjoy!


(I’m) truly thankful for great friends and colleagues who tell me the hard truths that allow me to become better.

– Gideon Yu


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Michelle De Guzman is the Executive Assistant to Gideon Yu, whose resume skills section include the sale of YouTube to Google, and financing Levi’s Stadium for the San Francisco 49ers. Michelle has been an EA for over a decade, despite lacking a college education, and working as a single mother, she has rightfully gained a seat at the table with the most influential people in Silicon Valley and Hollywood.

Michelle mentors a small group of EAs who also have not attended or finished college. Her guidance has helped many advance into roles at the biggest tech companies in the world.


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Michelle De Guzman 0:00
Hi, this is Michelle De Guzman. Today’s leadership quote comes from Gideon you truly thankful for great friends and colleagues who tell me the hard truths that allow me to become better.

Podcast Intro 0:18
The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, Game Changing leader assistant.

Jeremy Burrows 0:26
Thank you for listening to The Leader Assistant Podcast. Hey everyone. Thanks for tuning into The Leader Assistant Podcast. It’s your host Jeremy Burrows and we are at episode 87. And I’m excited to share my interview. But first just wanted to remind you all to check out leaderassistant.com/community We have a thriving Facebook community, a Slack workspace group where we share job opportunities, encourage each other, ask for help with a variety of EA projects and things related to our roles. And sometimes things are not related to our roles. So slack, Facebook, and we also do weekly zoom chats on Wednesday afternoons. So leaderassistant.com/community Leaderassistant.com/community Hope you can join us in our free slack, Facebook and zoom communities. All right, we will jump right into today’s episode. Hey everyone. Thanks for tuning in to The Leader Assistant Podcast. It’s your host Jeremy Burrows and today I’m excited to be speaking with Michelle De Guzman. Michelle is executive assistant to Gideon Yu co owner and former president of the San Francisco 40. Niners Michelle, how’s it going?

Michelle De Guzman 1:45
I am doing really well. Hi, Jeremy, how are you?

Jeremy Burrows 1:48
I’m doing very well as well. And I’m in St. Louis, Missouri today. Are you in San Francisco? I’m assuming

Michelle De Guzman 1:56
I am in San Francisco. Awesome. So

Jeremy Burrows 1:58
I’m hoping it’s a little warmer there than it is here.

Michelle De Guzman 2:02
Not so much.

Jeremy Burrows 2:04
Well, chilly today.

Michelle De Guzman 2:06
A little chilly.

Jeremy Burrows 2:07
So like 26 degrees or

Michelle De Guzman 2:10
not that chilly.

Jeremy Burrows 2:13
Nice. So tell us a little bit about how you ended up working with Gideon.

Michelle De Guzman 2:19
How I ended up working with Gideon. It’s actually a very funny story. I was driving to work one day, this was 2014. And I had gotten a call from Valentina, a recruiter I met casually. And at the time, I was supporting the CEO of a small startup in California. But I had just given my notice. And I was a few weeks away from starting a new job. Valentina told me that there was a very important client looking for an assistant. And she instantly thought of me. I told her that I was flattered, and thank you for thinking of me, but I was on my way to my dream company. And I remember her saying, do me a favor, when you stop driving, just google him. And Jeremy, Googling him, actually did not help. I took one look at his Wikipedia and said, yeah, there’s no way I could support this guy. You know, I called Valentina and I thanked her for time, but I was convinced that my experience was not strong enough to support someone like him. She pushed back and said, you know, look at it this way. It would be cool to just have coffee with him. And she went on about how an opportunity to sit down with some like, Gideon doesn’t come around, like ever. So I ended up taking the interview. And the daily met for coffee was interesting to say the least. Gideon had been running behind schedule. And there was another candidate meeting with him before me. But he was so late that I had already shown up for my meeting. And he wasn’t even there yet. So I actually sat at the table next to him while he interviewed the other person. And I’m sitting there and I can hear the entire conversation. And I remember thinking, this girl is going to get the job. I mean good for her. She has a master’s degree, previous experience supporting a high net worth executive. All of her answers were so polished and I’ll never forget this part. She was wearing a cardigan for crying out loud. I mean, she was just beyond perfect. And after her interview, she leaves and he moves to my table, which was literally the next one over and the interview was very intense. In the beginning he asked a lot of questions. He asked about my lack of education. He asked about my GPA in high school. I mean, this interview was tough. And I remember I started sweating profusely in my button up shirt, with no cardigan. And now I’m thinking good thing, I’m not wearing a cardigan. And I’m doing the best I can with my answers, just to get to the part where I can ask him questions. But then our conversation shifted to topics like family, my children, life in general. And after two hours of chatting about so many things and thinking, crap, he would be a really cool boss. But still, in my mind, this was not going to translate into a job, I had zero experience supporting such a high profile executive. And I’m sure that it is required for something like this. But a few days later, I got a call from Gideon, and this part to me is so unreal. It’s usually like the hiring manager or the recruiter or Santa Claus, or just basically anyone else. But the executive calling you and Gideon is telling me that I’m getting an offer. And at this point, I’m thinking to myself, Okay, this is the time to come clean. It’s it’s gone too far. And I start giving him the old. It’s not you. It’s me speech, which, as comical as it sounds, was 100%. True. But he tells me that he understands I don’t have the kind of experience he’s used to. And while things like booking a private plane could be taught, certain characteristics could never be taught. And there were going to be mistakes made along the way. But he was okay with that. And after the call, I received the offer and assign it. And the entire thing was so serendipitous to me and I think, because we were both completely transparent with one another, in talking about work and home life, which would have been completely impossible had I felt the pressure of wanting the job. But since I was able to be so open with him, it created a sense of comfort that ultimately resulted in being paired with him naturally.

Jeremy Burrows 7:22
Wow. Yeah, that’s interesting. I heard another story. Similar where it was like, hey, you know, I’m just gonna be honest, and be myself in this interview, and I probably won’t get it. But then they kind of the same thing happened where like, they really connected and next thing, you know, they got the job.

Michelle De Guzman 7:39
Ya know, I mean, I think some people tend to forget that an interview is a two way street. Both parties are trying to determine if there’s a fit, in my opinion, being brutally honest, in that interview is crucial for longevity. I mean, here I am supporting Gideon, roughly, what is it six years later? And I definitely owe that to the transparency that happened in our first conversation.

Jeremy Burrows 8:05
So how has your partnership evolved over that six years?

Michelle De Guzman 8:11
Well, Gideon, and I have an incredible partnership, and asked about my opinion in various parts of the business and just in, in life in general. And I definitely have a voice. I’ll give you an example. A few years ago, Guinea, and I were discussing the possibility of adding a second assistant to our two person team. We talked about pros and cons, how would we divide the workload, and people he thought might be a good fit. And personally, I wasn’t on board with the idea. I didn’t feel like it was the right solution. I think he could kind of see my lack of enthusiasm through my demeanor. And at that point, I remember him asking me, okay, so who would you hire? And at this time, I spent most days at the audio company. And I began to take notice of a very ambitious product manager. He has this like, incredible story of driving to California with no job, just trying to make it. But curiously enough, he wasn’t becoming BFFs with anyone at work, meaning that a lot of people didn’t like him. So I went around the office asking why people didn’t like the sky. I mean, just very direct data collection, like, what are these reasons? And the reasons people gave me actually made me like this guy even more. I mean, I will say the reasons on the podcast, but I began to realize pretty quickly, this was someone I can easily respect. And I remember suggesting this guy to get in. And he was extremely confused and asked, I mean, you would hire him as my second assistant. And I said, No Well, the question is Who would I hire? Anyway, getting ended up giving this guy a job and totally took a chance on him. He’s proven to be such an asset not only to get in, but to are now three person team. And I think it’s been a little over two years. And the kid who drove from Iowa to California was promoted to Chief Operating Officer. So going back to your question, our partnership has evolved tremendously. And I think, in the beginning, I was too timid to speak up. And there was a part of me where I was unsure if speaking up when matter, or if it would make a difference. But I can say that all of the times I did speak up, it didn’t matter and more times than not, it made a huge difference.

Jeremy Burrows 10:49
That’s great. Yeah, it’s interesting how, you know, over time, you can get that but what what do you think it was that? Were there other times where you didn’t speak up? And it went poorly? And that kind of made you think, oh, I should probably speak up next time? Or was it just simply a, you know, you got you built more trust and got more comfortable with working relationship?

Michelle De Guzman 11:16
I think it was just coming into my own, I think it was more it had nothing to do with as the executives that I was working with, but more. So just being comfortable in, in my ability to assess a situation and give recommendations. And I think that just happened with me personally over time.

Jeremy Burrows 11:40
Awesome. So when? And why did you become an assistant? Were you an assistant before working with Gideon?

Michelle De Guzman 11:49
Well, I started off as a receptionist at a small firm back in 2004. And I had just given birth to my now 16 year old daughter, whom I had when I was 20 years old. And to be completely honest, I took the receptionist job, mostly because I was hungry, and not in the deep, profound ways that Steve Jobs meant, but in the literal way that I needed to feed myself and my family. And a few months into my new job, the CEO asked me to support him. At that time, I had no idea what the role meant, or what it entailed, or what it could mean for the future. But because I am incredibly reactive and learn things very easily, I was able to complete projects, and then move on to the next task pretty instantly. And so that alone sort of helped me lock in a huge chunk of time, just learning by experience, which in retrospect, was huge for me since since I don’t have a college degree. So I really got that big break by working hard and people taking notice. And by 2011, I had just given birth to my son, and was working full time as a single mom. So I decided at that time, I needed to make a move. And I remember Googling, quote, best places to work, mom, and Cote. And after several hours of online research, I decided I wanted to be in tech, I studied all the skills that were needed. And I took a grueling job at a startup and cried myself to sleep every night the whole time, but tufted out to get that Tech experience on my resume. And then it was during that time I was introduced to my current executive. And so like many EAS, I sort of fell into the role. And while the reason I became an EA was not by choice, the reason that I stay in EA is absolutely my choice. I really enjoy what I do. And it never feels like work to me. I mean, does it take up a lot of my time? Sure. But it doesn’t feel like I’m using a lot of my energy on it, even though the work itself is pretty significant.

Jeremy Burrows 14:16
That’s great. So do you have any stories about crazy times when you save the day?

Michelle De Guzman 14:25
I mean, absolutely. I mean, there is one story that stands out. I think probably because this was the moment when I realized that networking was an important part of being an EA. It was back in 2016 and pokimane announced it would hold its world event in San Francisco. And what that is it’s this huge annual competition that they host in different parts of the world. And that year it was in California. So naturally my boss wanted to take a son and I think an EAS job consists of various tasks. And I find that most of these one off requests from, for me anyway, are always things you have never dealt with in the past. Therefore, it’s very unlikely you’ll have a contact or even know where to begin. And in my earlier days, I would immediately hit the ground running. I mean, I had no idea where I was running towards, but I mean, it felt productive, just to get started. But having a bit more experience, I now understand the value of sitting at your desk, just thinking. And I’m thinking, gee, how easy would this be had the event not been invitation only, I mean, I could buy the passes online, email them to my boss and call it a day. But it never works out that way. And some sitting at my desk thinking of ways to approach this. And I think, okay, maybe I can see if the venue can get some passes. And I’ll chat with one of those concierge companies that gets tickets for things like the Oscars. And of course, I’ll reach out to Pokeyman. Reaching out to the venue was a bust, they stressed it was a private event, and didn’t have any passes. So I reached out to Pokeyman through their contact form on their website, and was told that they didn’t have any public passes. And so finally, my last hope, was the concierge company. And after weeks of battling with them on if we can even get this done, they finally agreed to secure two passes for $25,000. I mean, oh, you know, just a mere $25,000. Wow, while you know, I should be jumping up and down. And because I’m finally able to get to my goal and complete this project. I wasn’t very satisfied with the terms. So I mean, I’m thinking to myself, There’s got to be another option. And my gut is telling me that Pokeyman is going to be the best way to get these passes, if they’re available to the public. So I went on LinkedIn, and searched for pokimane employees in Seattle, specifically employees with a marketing title, because they would be involved with the event. I finally reached out to someone, introduce myself, explained how Jonathan who is my boss’s son was a huge fan. And asked if there was any chance of snagging a few spectator passes. I get a response back a few days later, and was told, you know, they don’t sell the passes. But would just love to host Jonathan anyway. And you know, at this point, I’m so thrilled. I’m like jumping up and down on my desk, I’m celebrating and I’m just so happy. And I remember I had to come to the venue, the day before to get the passes, and met with the person whom I connected with on LinkedIn, had a cup of coffee, we chatted for a while. And she’s a very lovely person. And, you know, this was such a pivotal moment for me, I realized how powerful networking could be. And also just the art of being a solution collector, and figuring out which solutions to shelf and which to put in front of your boss and actually use. And you know, what’s really incredible is that all of that materialized from a simple message on LinkedIn.

Jeremy Burrows 18:42
Wow, that’s great. Yeah, LinkedIn is pretty powerful. I mean, that’s how we met. I think I’m pretty sure

Michelle De Guzman 18:50
it was through LinkedIn. It’s awesome.

Jeremy Burrows 18:52
Yeah, that’s great. Well, I love your I love your resourcefulness and just kind of reaching out and they can Alright, well, who’s going to be? Who’s going to be in charge of this event? Who’s going to be working on it? Who would you know, have maybe an inside scoop? So that’s, that’s great. Yeah, EA magic.

Michelle De Guzman 19:09
Oh, absolutely.

Jeremy Burrows 19:11
So what do you love about the role of an assistant?

Michelle De Guzman 19:16
The E role is so powerful. You’re at the table with some of the brightest minds. And as a result, EAS will subconsciously pick up skills from their executive, they become influential, they’re negotiating deals, and you really become an executive in your own right. A close friend of mine is a hardware engineer at Facebook. And the Facebook campus is close enough to my office that I can occasionally have lunch with him. And, and over lunch one day, he tells me that when some of the admins walk around the campus, other employees clear a path so they can walk by. I mean, it doesn’t get more badass than that, right? I mean, Even and, and so I really love how assistants are massively respected. Being a leader doesn’t require a title. I mean, it’s a characteristic and many of the EAS I’ve partnered partnered with over the years could easily become CEOs in the future.

Jeremy Burrows 20:19
Yeah, I love it. I think you’ve been EAS. You mentioned not not having a degree, I think being an EA for a few years is better than a MBA degree or a master’s, some master’s degrees. Just because you get so much real world, hands on business experience. So Oh, yeah, absolutely. So any tips for working with high profile executives.

Michelle De Guzman 20:49
So supporting a high profile executive is not for everyone. I mean, you have to be available at all times and be prepared for anything. I literally, like have my cell phone like taped to my body, I mean, IV, which might sound pretty standard as an EAA, but at this level, it’s not simply a matter of just being online and available. I mean, we deal with constant international time differences. So you might need to wake up at 3am to ensure you know, the flight crew is ready, and the driver is in position. And you’re basically awake, anytime your boss is awake. There’s a movie called The Devil Wears Prada, which is one of my favorite movies of all time. My husband hates it, because we’ve watched it so much. But it’s a pretty accurate portrayal of the role, in my opinion, except that the executive is much nicer in real life. But there’s a scene where the assistant is scrambling to find a flight for her boss. And she’s clearly out, you know, at a social function. And it’s so relatable to me. And while it’s not your boss’s intention to disrupt your plans, it happens. And you’ve got to be ready and willing to adjust with absolutely zero notice. And also, as an EA, you work very closely with your boss, and it will show if you don’t love your job. And we all know why people take jobs that they don’t particularly like, I actually went to school to become a nurse, I’m from the Philippines and all Filipino parents want you to get into nursing. And gather this is because the pay is relatively good. But during my clinicals, we would care for elderly patients and some of them would pass away. And I’d get really emotional and cried a lot. And I remember a veteran nurse came in to talk to our class about their journey becoming a registered nurse. And he said something that I still to this day carry with me. He said, Whatever you do, don’t do it for the money. And shortly after that, I dropped out of nursing school. And the point here being that you are well compensated for your role as a 24/7 ea, but I’m not sure the money will be worth the unhappiness. I mean, you’re trading your life, in exchange to do a job. I mean, you should love it if you can. So if you’re like me and truly enjoy the role, you completely understand the demands of it, and want to work with a high profile executive. My tips are, think big, be humble. Cast really wide nets and stay hungry. And not in the literal sense, but for growth, for accomplishments for interactions with people and just stay hungry for what’s going to happen next.

Jeremy Burrows 24:04
Love it. What would be a tip or maybe something you’ve done to stay humble?

Michelle De Guzman 24:14
I think that I’m just naturally humble and I think that being an EA kind of exercises that skill for me or not skill but characteristic and I don’t really like the limelight, I guess and even though I am fantastic at my job. I never feel like I’m fantastic at my job. I’m always I’m always looking for ways to be better. I’m always looking for feedback. And I’m always looking to learn things from other Are people and, and not have it be as a negative thing to be like, Oh, why don’t I know how to do this already. But I’m very grateful for the knowledge and I think just always wanting to learn it is very helpful.

Jeremy Burrows 25:21
Yeah, that’s great. The idea of you don’t have it all together and you can always learn is definitely a good way to stay humble. Awesome. Well, Michelle, thanks so much for taking time out of your night to share your story. And just some tips for assistance listening, is there somewhere we can find you online and connect and support what you’re up to?

Michelle De Guzman 25:46
I am on LinkedIn. I think that’s how we found each other. So I’m definitely on there.

Jeremy Burrows 25:53
Awesome. Awesome. Well, I’ll share your link in the show notes. And then yeah, well, we’ll talk soon. Hopefully we can meet in sunny San Francisco sometime and yeah, thanks again.

Michelle De Guzman 26:05
Thank you so much, Jeremy. Have a great night.

Jeremy Burrows 26:08
Thanks again to Michelle for a great interview. Please check out her on LinkedIn to say hi and thank you for being on the show. You can check out the show notes at leaderassistant.com/87 Have a good one and keep leading Well friends.

Unknown Speaker 26:34
Please loom you on Apple podcasts. Goburrows.com


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