Hey, Hey, Hey, we're back. We're black, We're Brown, and I am writing solo. It's your Girl, Mandy aka Mandy Money, and I am not going to be alone for much longer, y'all. For eight years, my little brother, Alex Woodruff has been petitioning to be a guest on Brown Ambition, and finally he asked at the right time. I have never been more impressed with him as not just a career professional, but also from a financial perspective. What he's managed to
do just by the tender age of thirty one. I can't believe he's old, but also that makes me so much older. But anyway, he has paid off a condo, paid off fifty K of student loan debt, built his own beautiful, gigantic home in the heart of our hometown of Atlanta. He has an Airbnb property, and on top of that, he is a badass tech sales rep for multiple companies like IBM and Salesforce. And did I even mention that he has this new, thriving creative endeavor as
a filmmaker. So I am inviting my little brother, my little brother Alex, on the show today and I hope that you all enjoy this conversation. All right, so you know, now I have this, I'm well, I don't know, I don't know what to call myself. And people say, like, what do you do now, I'm like, I do a lot of things, but one of the core things is I have the Manny money Maker career coaching community, which I've just started in the last couple of years. And
You've always been very supportive of that. Thank you. But it was sort of exciting for me in a sick, kind of weird way. Again, I'm a terrible person. Unlike yourself. You're very pure. But when you got let.
Go, when it happened to you, you were few important things like this in public you could have.
You never told me that you liked it when I got laid off.
Well, and from the sense of like, I love it when anyone comes to me with a real life career conundrum and I'm like, ooh, data and project and I want to watch this story unfold so I can learn to make me a better coach, you know, and yeah, so when you but also there's my therapist asked me, She's like, what is it about you and Alex that you think makes you guys have so much faith in yourself for success or whatever, and I was like, I don't really know what's to put up on my finger
on it, but like, I'm not worried about either of us. I'm not worried about you. I'm not worried about There's no real sense of getting let go could derail Alex's success, you know what I mean? The same way for me, Like if tomorrow, god forbid, they take away Brown ambition, I don't know who is in charge of that, no one, because we own it. But whatever, I'll I'll find some way, like I'll be okay. So I feel like when you came to me with, you know, unfortunately being let go.
While I was concerned and I wanted to help you, I also like wasn't I was like, oh, like he'll bounce back. He's going to be fine, you know what I mean. So that's why I think I could like take myself out of it and be like ooh project and like it's fun. But I want you to talk about that because I think you're such an incredible example. And I told you this at the time of professional resilience and someone who you know, you were at this place for less than a year or just about a year.
It was less than a year. It was around nine ten months.
Yeah, and you're like me a job hopper, So how many this was like your how many jobs? And I don't know how many jobs did you have up to this point? How many years?
An unwilling job hopper. I'm I'm searching for long term commitment. I think I found.
It, Like we could hear that bill.
Yeah, I was not trying to like.
Job like hop from the next thing to the next thing. It's when you're in the startup world in tech this can happen. It's kind of the risk you take when you go from an IBM or a salesforce, which is where I worked out of college, into the startup world where it's a lot faster, a lot looser, and you don't necessarily know what's going to happen. The flip side of that is that you can have massive earning potentials. You have a lot of autonomy to run yourself and
your business like it's your business. And it speaks to me more going back to what we talked about earlier, it speaks to who I am to work at a company that I know, the CEO, I have a relationship with that person, and I know what we stand for and I can reflect that. So yeah, getting laid off
is tough. It was very, very startling because I think highly of myself and so while I wasn't shocked because I knew that as a company we weren't performing and as an individual I could have been doing better, but I was definitely surprised. I thought that it wouldn't if it was going to happen, I thought I would have been safe. So there's a couple of things I want to say, Like, definitely I have a chip my shoulder. And when you talk about you always knew I was
going to be okay. You're not worried about me, You're not worried about you. Like I'm going to be okay because I'm going to make sure that whoever made that decision regrets it one way or another.
And they probably won't.
They don't know, so you do have like in my head, Yeah, I want to like make them regret it. I want them to be like saying that dumb shit, Like that's what I want. And so I'm going to force that to happen. And so Fiddler, where I work is getting the hardest working version of me, like possible. It is the I'm on go mode right now because I need to validate not only to myself but to this imaginary hater who I've created in my head, who thinks like I'm going to fail.
I'm gonna flyp like that. That is how I operate.
But on the other end of it, in terms of like when it happened and the fear that I had two reasons I wasn't really afraid. One is that my girlfriend has my back, like she financially can help us out and get us through a period of lean time. And then the other thing, it's not all that lean over here. I'm doing okay, Like I'm not scraping the bottom.
I didn't have a lot of cash in the bank, which you expressed to me, but you didn't have an airbnb.
Yeah, Like, what's the worst that can happen?
Now my massive house and make a bunch of money off of it, and then by the time I'm done doing that, I have a new job, and.
Like you just got to be able to be adaptable, Like.
Yeah, I wanted this.
House, but what if it doesn't work out, that's okay, Like I need what's actually important to me as a human it isn't this house, it's not this neighborhood, it's not the job that I was in at the time. It's like, how do I ensure that I'm not losing sight of what's actually important to me?
And so when I got laid off, Yeah, it was.
It was scary for a little bit, but once I started thinking about it, and I'm like, I'll be fine. I'm going to handle this and no matter what, nothing's off the table as long as you know, me and the people who I love are protected and we're fine, and maybe we live in a smaller place, maybe we rent for a while. None of those things ended up happening. I got a new job in like three weeks.
But like, yes, so let's talk about that. Yeah, first of all, your first your first correct step was to call me.
I called you almost immediately, right, I don't know.
It's extremely pregnant and you know, about to pop any.
You were like any moment.
Now, I'm like, hey, wait, we're kind of putting a date on it. And if we do that, do you think that matters? You've been pregnant twice, Oh, you're right, Well, you know pro life, I've been pregnant.
Sleuthing that hard, I'm fine with.
Yeah, you're right, Okay, Okay, yeah, so of course you called me right away, and I just pro life, I've been pregnant three times.
Okay, Yeah, I'm sorry.
I just I just I caught up with you.
Stick around, kid, you'll learn some stuff today. All right. So you called me up. We talked about it, and like immediately I feel like you were it was your full time job to be looking for work, and like quickly talk about a few things that you did that you feel like three weeks later you had an incredible Not only did you have an incredible job, because we got to the negotiation, which is also so fun for me to like have a backseat to watching you negotiate
because I love seeing it happen in real time. But you had options in three weeks. It wasn't just like I got a break, It was you had two or three potential opportunities. So I think it's really crucial for people to understand how that came to be.
Yeah. So, I mean it's just like when you brought up how I lost hope in college. It was the same exact scenario.
Like I got hope scholarship, not hope in his life.
Oh, you're right, I forget people aren't fromantic.
I lost the Hope scholarship.
I'm not hope as a person. Yeah, I lost a scholarship that I had going to college and that was that was a big wake up call. It reminded me to keep the main thing the main thing, and understand what my floor is and for me, in order to do everything I love and everything that's important to me, I need to be a highly functional software or sales executive. And if the place I was at I wasn't able to do that or deliver, I need to go and fix that first. If I don't, everything else is now
under threat. I can't invest in my movies, I can't have a lifestyle I want to live. I can't you know, put into my retirement, et cetera. So it was extremely important, I put to your point, I was like my full time job for that three weeks was to find a job.
In terms of how I got the options I have developed.
Over the course of my career, A good reputation, and several really important mentors, people who have vouched for me, people who have supported me along my process. One of them is Seth Dobrin, who at the time was the president of the Responsible AI Institute, which I'm a board advisor for, and he connected me with a few people immediately as.
Well as Exponsible AI, the Responsible AI Institute. Okay, gotcha.
He connected with me with people.
I was on LinkedIn, you know, doing what I do from a state sales perspective, but now looking for a job and I'm the product.
So it was very it felt natural.
It was scary for the first few days, but then I started getting interviews and then you start then I'm in the mode, right, I'm I'm Max.
So you reach out to seth, you reach out to the mentors, like via LinkedIn or email or whatever, let them know. Do you tell them? Because I get this question sometimes, should I tell people I've been let go?
What you need to think about? What was your p That's a fair question, I think.
And you had a lot of concern about reputational risk too, until the stigma warranted and valid.
Reputational risk because it wasn't my first time leaving a startup. Right in the prior year, I had left a company and went to a startup and then that startup folded. I didn't get let go, but I had to get out because it was under a lot of pressure. So I left for another startup, and then that startup laid me off. So like, for me, my reputation as a job hopper is not something that I think is valuable in my career. I don't want that reputation. I want
the best opportunity for me. Don't get me wrong, but I don't want to be looked at as a job hopper. I want to go somewhere and deliver and be looked at as Wow, I'm glad that person was here.
So I was worried, yeah, about who I reached out to.
And I think for anyone listening, it's important to think about what your reputation is with somebody before you reach out to them and tell him you were let go, Because if they don't think that highly of you, and you were reaching out to them and letting them know bad news about you and asking them for help, like maybe you should find someone else.
Their reputation could be at stake as well. You know, they have to really well like if they will, because they may decide not to vouch for you just for fear that if they do, like they don't really trust that it'll reflect, you know, well on them. But if someone knows you, they're like, oh, Alex was Alex ended up here? Not because he's not great, but because you know some thing's happened to Alex. I'm still going to vouch for Alex as the product, you.
Know, absolutely, and you don't want to.
It's always you're always trying to build the best reputation for yourself with everyone in your network that you possibly can. So if somebody already doesn't think that highly of me or is not a huge fan of mine, I'm not bringing them bad news.
That's not a valuable investment on my end.
I'm going to wait to pull up on them after I have some good news so that I can improve that impression that they have with me. So I'm going to the people to your point who already think highly of me, who know that if I was let go. You know, it's like when you have a breakup, you go to that friend who's going to be like, man, they were bugging, Like that's who you want to go to in this environment. You want to go to somebody who supports.
You, yeah, and then would vouch for you. So that led you to a couple of not just interviews, but like because you're niching into and people who want to break into tech, I feel like listen up because like
you targeting were you specifically targeting startups? Because I feel like that because it's such a smaller sort of I don't know, like companies small fewer people in between you and leadership, You're able to get that FaceTime with leadership pretty quick, you know, versus like applying to Meta or Google and you know, going into this huge stratosphere that's just like it's hard to break into.
You need to understand what your leverage is. So for me and the skill set I have and the track record I have, I have the ability to go to a startup who needs the job that I do, which is sales, and say you should consider me. Right, But if you're brand new and trying to break into the tech space and you're trying to get a job like the one I have right now, it might be more beneficial for you to go to a bigger company who is hiring more people at once, who has a training
program like what I did when I joined IBM. Right, that would be maybe a good use of your time. Because if you go to a startup. They're expecting you to be ready made. They want you to have gone through training already. They want you to be ready to literally join and Fiddler, I was having meetings with customers like a week after I joined, because I.
Already knew the space.
I was already you know, enough of it expert to be able.
To They don't have time to train.
Yeah, they didn't need to.
Yeah, they didn't want to have to train anyone. So that's the leverage I had coming in. If I were brand new and I were trying to get into a sales job, I would go somewhere with a training program that allows me to generate more skills and a track record of success. And then if I decide eventually I want to be in startups, which is how my career
you know, uh went, then I can do that. And now a startup is a lot more likely to look at me because I have a track record of success and I've been trained already, you know, a valuable program.
Okay, all right, that's really helpful. I think that that's really good to note as well. Like, and I bring up IBM because I've got some clients who work for IBM, and I'm like, shout out to the big companies who give people a foundation of experience. Yeah, so there's no shade to going to a big old company. But I think what's great is that you weren't afraid to change your mind and you weren't afraid to go in a different direction. And I recently heard a statistic that was
like the highest and this is a basketball reference. Okay, so obviously I don't know what I'm talking about, but this stat was like the top five highest scoring players were also the top five highest missed basket players. What do you call that brick?
Yeah, so like they had the bricks.
Yeah, you do conference field goals missed, so they probably had the most.
Yeah, because they're shooting a lot o basketball.
That's not a field goal, is it.
Yeah, it's called a field goal. It's confusing. This is a tough what it is?
Yeah, the thing that Shaq can't do. That's a field goal.
That's a free throw?
Oh feel a free okay anyway, Yeah, but my point is like in order to get the wins, get the house, get the airbnb, you know, get the debt paid off, you had to make like a lot of like take some risks, like go for it, you know, and the layoff being one of the times that it didn't that you could perceive it as like, oh, took that shot, it didn't pay off. But look at all the things that, you know, all the chances you did take that did
pay off. And I feel like a lot of people that I work with and even who listen to the show just are like love coming back because it's like giving you permission, helping you feel safer, you know, taking that shot, because failing is yeah, failing is scary. I have failed. I will fail, you know in the future with some projects that I pursue. But I'm also going to really succeed because I'm going to keep doing stuff.
Yeah, you know, That's why I loved when you first started the show, Like I'm a I'm an artist, so I vibe with concepts and name and even brands and logos. Thanks to wearing ours again. By the way, follow us at Pineapple cut Pictures on Instagram, or you can follow me at alex J Woodriff. I may not be on in a few months.
I might have to leave, you should have said at the beginning of the show, as I will. That's what most listenership is. You know what I'm saying.
Yeah, yeah, like the Brown ambition, the name it speaks to everything you just said. It's like you have to have that be your affirmation. Be ambitious, be audacious when you have the ability to, Like, those are things that have served me very well. Is when I know that I understand what it is I'm doing, I'm good. Those
are the times to be audacious. Those are the times to try to go a step further than maybe where you'd be comfortable, and that's how you're going to For example, I built the house after I first bought a condo. That was pretty audacious, but I did have a little bit of a foundation because I had renovated my condo. So those things, you know, are important to try. And now whatever I do next, who knows, right, but it's going to be something that's audacious because that's just part of my DNA.
I mean direct writing and directing your first features sary short yeah, short film, Yeah, I've learned that from Project green Light. It's a short, but still it's really freaking amazing. I wish I could be there in person to see it. But I want to end on that note, just like talking about the audacity of Brown ambition and how you persona by that, and I'm just so damn proud of you, baby.
Bro, thank you so much, and the feeling is way mutual.
I'm so happy. I wish TIF could be here. I tell her too.
But y'all, maybe you'll come back on the show.
I want to be back.
I mean, you know, you know if you're watching the reviews on this one, like the I want to get the I want to get.
The listening, well, I don't know, you're gonna have to be on i G because like that's where the BA fan is on IG interacting with our clips. Also, you can listen to this on or watch on YouTube if you want to see how much Alex may Or may not look like me, y'all me, I am the original doppelganger, not Drake. Yes, people, then no one used to say you look like Drake when.
His hair goes down. Yeah, it's pretty uncanny.
How much we look like m Yeah, but you know you'll always be number one, all right, Alex James Mischief.
Thank wow.
I love it.
It was either it was either the Pineapple cut shirt or the Harry Potter Sorcerer's Stone T shirt that you gave me. That I couldn't find.
Oh, that's the shirt I brought you. Okay, I knew i'd brought you a shirt.
That's what, and I knew it wasn't Pineapple Cut, But you know what, I just moved on from that, but you came around, all right. Thank you Alex for joining Brown Ambition. You guys please run to go follow Pineapple Cut Pictures on ig where you can stay abreast of
all the news you've got. Your your shorts are entering film festivals, and I hope people get a chance to see My Sore Magic, which is just so cute, so sweet and adorable and heart you know, heartwarming and beautifully shot, just gorgeous the colors, I mean, so much of it. And also Forgive Us is one of the films that really whoa very different than My Sore Magic, but another short that you all have done. And good luck this weekend making your first film.
Thank you.
I won't try to call our text you don't worry, but I will. You won't answer.
That's good.
Focus on the art.
Yeah, I will be very very busy.
Yeah, but it's so dope. All right. Bye,