Startup vs Fortune 500 Companies? How to pick

Welcome back to the Ally from Corporate Podcast. If you're interested in learning more about career development, job searching and growing as the badass professional I know you are, you've come to the right place. So sit back and relax. Let's get into it. Welcome back to the Ali from Corporate Podcast. I'm your host, Allie, and today we have a very special guest. This podcast is career development and job searching. I have guests on all the time, like this wonderful one that we have today that I'll introduce in a minute who talk about their job search experience, their career journey experience, lessons learned that they want to share with you. So let's get into it. This is Kyle Thomas. Kyle, I'm so excited to have you. Thank you for joining us.

Excited to be here?

Yes.

Yeah, excited to be here. Thanks for having me.

So Kyle, you live in New York. You are a amazing dad of three. You are a. You help startup job seekers land amazing roles at world changing startups. Is that right?

Yep. Ambitious career accelerating roles at world changing startups. Best way I've been able to describe it.

I love that you put the word ambitious in there because I truly believe if you are looking to land an amazing role as a job seeker, you need to have the ambition piece. Like, you can't be a lazy job seeker. You're not going to get the roles that you deserve or want. So I love that you have that in there. So tell me a little bit about, I know you're a career coach, tell me a little bit about your program first and the ways that you help your clients.

Sure. So the program that I have created is essentially everything that I wish that I would have had when I was looking for my startup jobs. So startups are kind of a bit of a black box to some people outside. Even if you're in the industry, sometimes it can be hard to understand what's out there. Salary and equity is challenging. Quite often that people don't have a ton of exposure to. So, um, the program that we help, who we help is like I said, ambitious career or ambitious job seekers looking to accelerate their career through their next role at a startup. Most folks are mid career and senior level folks, although we do have some young, hungry hustlers, you know, young, young career folks and they actually see fantastic results as well. And so we combine a handful of different elements. There's a community element, so everybody's together. My goal in the program, and just in general, is to eliminate the anxiety, uncertainty and loneliness of the job search. The community element definitely tackles that loneliness piece and then we help people create that really compelling vision of what's the end point, two years, five years, 10 years down the road. And then help them develop the understanding of what are the skills, experience, network and teachers that are going to accelerate them and make that vision that they have of the future inevitable. Get them really confident in what? In their ability to get there. The results they drive, who they drive them for and the types of companies that they want to work for going forward. And then work with them to develop a scalable networking technique that will leverage their existing network. Really works for cold targeted outreach at the companies and individuals that you want to work with. And how to create value, what does that even mean? How do you create value in order to stand out with people? And then we layer on top of that things like, you know, mock interviews and all that kind of stuff to really make sure that you walk out of the interview process saying and really like the approach to any company that you really want to work for saying there's nothing more I could have done to land that job. And then when it comes to startups, we layer on top of that investor grade tools. So because I have my own company, I'm able to get access to pitchbooks so we can pull really detailed targeted company lists. Once you develop that ideal target characteristics for the type of role and the type of company that you want to go after, we can pull lists of hundreds of companies that match that description that have offices in your location or have offices in the US and we're also able to pull hyper accurate salary and equity benchmarking based on the function of the role, the seniority of the role, the location of the role, and then a bunch of details about this specific company. So things like the amount of money they've raised, how much the company is worth, the number of employees at the company, the revenue of the company, you know, we can get really granular and specific so that when we help those individuals negotiate their salaries, we're able to maximize that offer and really accelerate them towards, you know, that, that end payout. And particularly when it comes to startups, the big thing that, that a lot of people say is they're like, oh, it's so risky. And so we try and de risk that with a, the method and really like making sure that folks structure it in a way so that they're getting those skills, experience, network and teachers because can lose a job, but you can't lose those things and using those investor grade resources to say okay, investors say that this company has a 98% chance success of exit. Now, you know, take that with a grain of salt but at least it gives you a little bit of more confidence that this company's going to be around for a while. And there's other methodologies that we teach in the program to how you suss out the company's longevity and if you want to work there. But that's the, that's the basis of the program.

Nice. That sounds so helpful. So you touched on a couple points that I want to bring back the loneliness of the job search. Last time I job searched it was so depressing and just like in a vacuum. Like I love that you have a community aspect because if somebody is getting auto rejected and getting emails from, let's be honest, robots saying sorry, you didn't get the role, that could just be so discouraging. But if you have somebody else that you can talk to and say like hey, are you going through the same thing? And they're, they're like yeah, I got those emails too, but here's what I tweaked instead. Maybe that'll help you. Like that is a game changer. So I love that you have a community aspect. Another question I have is I used to use glassdoor.com and salary.com for salary benchmarking data. Do you use different tools?

Yeah.

So.

I was able to gain access to a tool. The reason why I use the tool that I use now was. So the answer is yes. One of the things, the vision that I have for the program and just like in general there's so many things about the job search that are incredibly frustrating that I don't necessarily think need to be that way. And one of the things that frustrated me the most was that you kind of have to go out into these like self reported data locations and then piece together like what is the 10th percentile, the 20th percentile, the 50th percentile, the 75th percentile, the 90th percentile of each of these different roles and all the different companies and then trust that the person's giving you accurate data and, and it's so frustrating as a job seeker and you have no idea like you're at such a disadvantage because these, these like many companies there's like free resources for them to use if they plug in their salary information and cap table and things like that. So I use a different resource for that that's not self reported in order to get that data.

That's so cool.

So and the rationale behind that? Yeah, the rationale behind that is Access to that tool when I was leaving Uber allowed me to negotiate a $100,000 salary increase. And the. And I would not have asked for that much money had I not known that that's how much people in that role were making. And so this is why it can really work as a disadvantage to the individuals on the job search, because they don't know what people are worth. And oftentimes people are so cagey about their salaries. Luckily, me and my friend group that had left Uber were very open about it. And so I had a relative idea, and then this gave me actionable data that I could take and hand to the startup and say, look, this is what I'm seeing. I don't know if you guys are kind of thinking about it the same way, but here's kind of the data and what I'm. What I'm looking for.

Wow. So you worked for Uber, right? You were early. One of the early employees.

Yeah, so I was employee number 250.

250. How. Okay, I'm so curious about this because obviously Uber has grown to be a. Would you call it a unicorn or was it a unicorn?

Oh, yeah, it's like a. It's a. It's at least a decacorn. I don't know what it's called when it gets into. Yeah, it's a multi decacorn at this point.

Okay, so first, can you define what a startup unicorn is? And then I want to hear all about how you got the job at Uber.

Yes. So a startup unicorn is a company. Somebody's going to probably, in the comments will.

I'll look it up. I'll look it up.

It's a company that's. It's a company that's. That's reached a billion dollars in valuation. There's some other factors in there as well. I think that they.

You're right.

Yeah. So. So there's. There's a couple other factors in there as well, I think, to qualify it. But it's essentially a company that's reached.

A billion dollars in automation before going public, obviously. Right?

Yeah.

Wow. That's insane. Okay, so tell me, so you got a job at Uber as one of the early first two 50 employees. That's huge. And other people listening and watching might also want to work for a company who they think could get that big, but they're starting early on. So how did you get in early? Why Uber back then? Did you know it was going to be huge?

So it was, it was definitely not purposeful in a sense. I. I definitely Wanted to work for the company. I, I grew up in Seattle and Seattle was one of the first markets that Uber launched. And Seattle does not have a very good public transportation system. They, they have buses, but there's no subways. There's no, there wasn't trains at the time. They've gotten significantly better since then. But at the time we were relying on yellow cabs. You know, I was, I was 20, in my, like early to mid-20s. We were going out on the weekends and you know, you had to call the cab company and they might show up, they might not. They havesle of you about cash. And so when Uber came about and I, you know, you requested the car, the guy showed up, he's wearing a suit, he opens the door for you, there's cold water. It was just like such a game changer that it was worth the, you know, nominal extra cost and it wasn't really that much expensive. And my introduction to the, to, to the, to the company, actually, I first found out about it one of the, the only, or one of the only members of my high school who had gone to an Ivy League school had gotten a job at Goldman Sachs. He was definitely making like the most money of anybody that I knew out of college. And then on LinkedIn, I see that he quits his job and starts working for a company I'd never heard of. And I was like, what in the world? Like, why would somebody go and take this job when they have the, you know, the golden ticket? And that company was Uber. And he lived in New York City at the time. We played basketball growing up and knew each other in elementary school. And ultimately what ended up happening, I was working a job I hated in Seattle and tried, applied to the management trainee program there, was trying to get ahead as much as I could, and was rejected three times in two years. And then the final time I was rejected, I was like, I don't even want to be here. Why am I doing this? I'm not super interested. It's like pulling teeth to try and get interested in this. So I went on this kind of journey of self discovery over a year and traveled to Guatemala for two weeks. I don't speak any Spanish. Ended up at EDC Vegas at this massive electronic music festival and ended up meeting a gal that would become my future wife at that festival. She lived in New York City, I lived in Seattle. And so we did long distance for a little while. Eventually I was like, I hate my job here. You just got promoted, I'm going to move over. So I Quit my job at three months of Runway, saved up, moved to New York City, in with her and her three roommates, and really, like, spent the three months pounding the pavement. Like, didn't really know. I knew that I wanted to do something that. And I kept a journal the entire time, which is incredibly helpful to look back on. But I knew that I wanted to work in something that was really excited about and passionate about. So I was reaching out to just, like, really successful people on LinkedIn. Got some conversations there, but wasn't really building traction. I didn't know what I know now and, like, what we teach in the program, and was about to run out of money. So I took a job at a company where I'd be selling domain names. Wasn't passionate about. It would have been terrible. And while they're running my background check, all the networking that I've been doing paid off. A gal that I knew in high school was living with the guy that had become one of the first 50 members at Uber. This guy I used to play basketball with, and he shoots me a text and says, hey, heard, you know, Kelsey told me you were looking for work. Would you be interested to come and help us hand out marketing palm cards at the airport taxi lines? And I was like, 100%. I'm in. And he was like, all right, 25 bucks. That was like, you know, a million dollars to me at the time. 25 bucks an hour. So I went out to the tiny, little crappy office in Queens. And, you know, this is one thing for. For folks that are looking at startup companies, like, it's not all, like, the sexy stuff, you know, this. This office was, you know, a dump in. In a, you know, not so awesome part of Queens. And he filled up a backpack full of these marketing Pong cards for me and took and shot me in an Uber along with another tax taskrabbit out to the LaGuardia Airport taxi line. And then for hours, I just, like, walked up and down selling them on coming back to the office, create an account, did that for a couple days, tried to be as helpful as possible around the office. It helped them, like, break down iPhones. So at the time, the Uber app was not able to be downloaded. The driver app was not able to be downloaded in the App Store, so we had to give iPhones to the drivers. So it was kind of an easy sell. When I was walking up and down the taxi lines, I'd say, you know, have you. Have you heard of Uber? Give my pitch. And at the end, I'd Say, and we'll give you a free iPhone. So, you know, that got people back to the office. But you know, he brought me back into the office, said, hey, you know, don't go out to the taxi lines today. Help me sign up drivers and teach them and onboard them. So I did that for a couple of days and by the end of that week, you know, I was like, hey, Andrew, do you have any full time positions? He said, yeah, 100%. We're looking for another operations manager. Just like shoot me your resume and I'll hand it to the recruiter. So I never applied. I went through an analytics exercise that was terrifying. You know, it wasn't looking back on, it wasn't crazy hard, but like, you know, I hadn't used Excel in so long and things like that. And, and then the recruiter, and this is what I teach in the program. The recruiter said, the team loves you. It's a, you, you're already doing the job. So the team loves you. You're already doing the job. It's a no brainer to move beyond to the final round. And so I interviewed with the hiring manager. That's what I interviewed with the hiring manager. And that in itself, the interview with the hiring manager is another pretty funny story. But. And then I was hired and it was a dream. I worked there. Like, you know, one of the things that I think I, I talk about in the program and I teach other people is it really pays to go after companies that you're really excited and interested in, because if you're not. There was a guy that was also living with us at the time in New York City and he had other career ambitions. And I said, you know, hey, why don't you come with me? They need extra people. And he said no. And his career is different now. He didn't necessarily want the things that I wanted, but you know, mine, you know, turned into this seven year journey at one of the fastest growing companies of all time. And it was awesome.

Wow, that is such an incredible story. First, I love how you met your wife. I want to go to EDC someday. I love like electronic in house music. So that's awesome. Wow. So. So you got that job through networking. Bottom line is networking, being willing to provide value for somebody without anything in return besides $25 an hour, which, let's face it, that's not.

Yeah. And honestly, I would have done it for free. Yeah, probably I would have done it for free anyway. Yeah.

Yeah. And there was. You saw your, your basketball friend leave a huge Opportunity to go somewhere that was an unknown. And you were like, he probably knows something that I don't. I'm interested now. So that's so interesting. Okay, so let's talk now about the differences between startups and big companies. So you probably have more startup experience. I have more big company experience. In my experience with interviewing at big companies, it's like an elephant moving through a forest. And I would say a startup is like a mouse running through a forest. The elephant, it's slow moving, it's big, it's hard to pivot, it's hard to turn its big body and pivot directions. But a startup is like, zoom, zoom, zoom, zoom. So tell me about startup interviewing experience and like company culture in general.

Okay. Startup interviewing experience. Anything specific about startup interviewing experience that to kick off or just go where I.

Yes, I want to go. So in my. So I'll tell you where I'm headed with this question. So in my experience, I've worked for two startups. I got burnt out at both. Both ones and I had to leave. What indicators are there during the interviewing experience that a job seeker can look for so that they can tell what kind of work life balance they'd have at the startup? Are there red flags that people are like, oh, they look really stressed out or they're. They were 15 minutes late to this interview, like, maybe this isn't the right place for me. What are some red flags for interviewing at a startup for somebody who wants work life balance?

That's a good question.

Such a specific question. It wasn't supposed to be so.

Yeah, no, no, no, no. It's a good question.

So.

I think one of the things that, one of the things that I suggest people do as they're going through any interview process is to not just reach out to like the hiring manager and the recruiter, but to reach out to people on the team that they're going to work or that they're like, targeting. And oftentimes those individuals will be quite more forthcoming than somebody who's involved in the hiring process or somebody who's on the interview panel. And so you could really ask them, you know, what are things that you wish that you would have known coming in? What are the biggest challenges that you have? What does. The way that I like to ask those types of questions is I will frame it from my personal experience, provide both sides of the coin, and then ask them about something with regards to work life balance. So what that looks like is something along the lines of, look, I've worked in an Environment where everything was super cool and calm and every once in a while there would be kind of these crazy all hands on deck moments where everybody had to jump in and we would work until midnight and get up at 4am but really it was kind of this short period during a crisis scenario. And I've also worked in places where it was all hands on deck all the time until we raised the next round of funding. But it was like months at a time. So just out of curiosity, how often are things all hands on deck? Is that kind of what's always expected? Is that really just a once in a while thing? And then of course they can kind of BS you, but that's the way that I like to frame that. So it's not coming across as, look, I'm not wanting to work hard. It's coming across as like, I'm just trying to gauge to what level is there an all hands on deck mentality. And, and how often are these, you know, midnight runs and late office visits or working the weekends happening?

Working on Christmas?

Yeah.

Yeah. Okay, good. And some people who are looking for a job and who want to work for a startup are totally cool, putting in 60 hours or more. They're, they don't, maybe they don't have a family yet, maybe they're single, maybe they live alone and they're like, yeah, I want to put in 120% at a startup and get a big payout and I'm, I want to be dedicated. But some people are looking for more work life balance. Maybe they have a family, maybe they have hobbies, maybe they're really into traveling and they can't work weekends. So. Okay, that's interesting. Yeah. Startup.

Another. On that, on that, on that, on that front, like, you know, you could ask somebody, given that, like if those are your priorities and things like that, you can ask somebody about their hobbies and how often they get to do them. Right. And that's like a, it's like a, it's a, it's a, it's a circuitous way to say like, what are you super interested in? And then you ask a follow up of like, and how often are you able or do you get to do that? And they may say like, oh, never, not since I started this job. And then you're like, okay, that's an interesting point.

Okay, no more hiking for me. Yeah. So I tell, I teach people it's important to make small talk at the beginning of any interview because that you establish rapport with your interviewer. You show that you're like, you're calm, you're calm, cool and collected. You're confident. So that's a great question to ask. Hey, how was your weekend? What'd you do? If they say, I hiked, I went, I visited my mom in another state. You know, I relaxed, I feel great. But if they're like, I worked all weekend, then you're like, okay, interesting, cool. I love this. So, okay, we have one question from people on TikTok. I'm on TikTok Live right now. If you're not following me, my handle is at Ali from Corporate Zero. And we have a question for you from somebody. So how do you talk about the funding aspect in an interview without sounding like you're money hungry? How do you bring up money?

Yeah, so I think that there's different things to be curious about when it comes to funding and this is why in our program I have access to a software called PitchBook, which is a like investor grade software that gives you a all the details about the company's recent fundraising history, who the investors were, how much they fundraise raised. Oftentimes they'll include in there what they've said that the fundraising is going to be used for. And so a doing your research pays off a ton when you're asking that information. So if you're curious if the question is more related around, how do you ask about funding? Because you're not 100% certain whether or not this company is going to be around for the next six months, then what I would say is do your research, go to CrunchBase, go to PitchBook, search the company's name and search for recent funding, or search for funding with the company's name. And you should get enough information as to when the last funding, when the last funding round occurred, how much it was. And so if it was like super recently, then you can ask questions about, hey, you just raised X amount of money from your, from your understanding, depending on the level of seniority that you're applying for, the person may know this or may not, but what are the key priorities that the money is being put towards or something like that. You can also phrase if the question is around burn rate, because that's something that burn rate is essentially how much cash is the company burning every month. And it's really important for a lot of these unprofitable startups because essentially it means how much longer can the company survive until it goes under without another round of funding. So, and the level of openness that people have with regards to that Varies. Oftentimes you can ask like, hey, I would. Again, similar way of framing the earlier question that we were talking about. I would frame it coming from a point of curiosity and less of a point of, like, accusation or. And I would. I would. I would frame it using data so you can say something along the lines of, you know, I saw that you guys recently raised, you know, $200 million, but the funding was two years ago. Out of curiosity, what's the current burn rate? And how much Runway does the company have before they need to fund again? And are. Is the company currently fundraising or do they not need to, due to the current profitability of the company? So, like, and. And that will even, like, you being able to reference the fact that they raised money and how much they raised, who they raised it from or whatever. It just, like, shows that you did your research. So that's the one question. And then based on funding levels, like the salary ranges and things like that, like, you know, it depends. That's why, you know, I wouldn't know. And so, like, that's why I have the software to help me out. But that's the way that I approach those types of funding questions.

Okay, got it. And before we end here, I have one more question for somebody on Live. What does Kyle think about unlimited PTO at a startup? That's a hot topic right now. A lot of companies are starting to offer that it might be a bad thing because then they don't have to pay you when you leave for your unused days, but maybe it's a good thing because you can get every Friday off. What do you think?

Yeah, I think so. I think it has its pros and its cons. So I'll talk about both from my personal experience. The pros are that you don't really ever have to worry about. Like, hey, there's this event next Tuesday. You know, is it. Is it cool? I. I did this work. Here's the coverage document. Is it cool if I take it off and the manager's like, yes, 100%. Or like, you just don't need to worry about, like, oh, I'm running out of names or whatever. Yeah, right. Like, that's, that's. That's the best thing. On the flip side, it can work against you in the sense that because you don't have that scarcity, you're less likely to use them. So there's no, like, there's no. There's no mandate that you use a specific number of days. And there isn't. It's hard to Judge, it's like is 30 days too much? Is 20 days too much? Is 15 days too much? And so really it really puts the onus on you as the employee to have an open and honest conversation with your manager and really understand, you know, you have this open, this PTO policy. Just want to kind of put our cards on the table and really understand to what extent can I take advantage of that or what does that look like and how can I best prepare you so that I'm able to take the days off that, that I want. And I, I really like in the early days at Uber I didn't take, and I know this sounds awful, like I took like one vacation in like the first four years but, but, but I'll put like an asterisk on that. I can't tell you how many three day weekends, four day weekends, like you know, and that was more on me. And so like other people did take advantage of it and took you know, a week here, a week there. But, and then like even, even over the holidays I'd go home for multiple weeks and then like I'd be working but like you know, on and off it wasn't super serious. So it just provides a lot of flexibility there. But it can be abused because, because like I said, in the event that the company does not like you don't have a good manager who is going to be open and honest with you and provide that expectation setting, then it can be really stressful as an employee. So best practice I'd say is make sure that you have a very open and honest conversation with your manager as early in the process as you can after you're hired in order to set those standards for look, I'm going to do everything that I can to create a coverage document and make sure that whenever I do take time off, the team is a hundred percent ready and prepared in order to cover anything necessary that I do on a day to day basis. And out of curiosity, how many days is too many? How long should I let you know in order to take that vacation time and things like that?

Great answer. Love that. Great. Well, this has been an awesome session. Talking with you again. If you're listening and tuning in for the first time, this is Kyle Thomas. He helps ambitious startup job seekers land career accelerating dream roles at world changing startups. So thank you so much for joining us. I know my listeners, this is going to be on YouTube. It'll be on Apple and Spotify and then live on TikTok. I know my listeners and viewers have gotten a lot of exciting stuff. We've had over 2,000 people join us on TikTok since we started, so this has been great. Thank you so much for joining us. Thank you. And I will talk to you later.

See you, Allison.

Bye.