How to break into tech sales without a perfect background | Grey Bradshaw-Mack (Default)

In this episode, I sit down with Grey Bradshaw-Mack, GTM at Default, to talk about his unconventional path into tech sales, from starting out in nonprofit work to breaking into software sales through PitchBook and eventually moving into early-stage startup roles. Grey shares how a major skiing accident forced him to relearn how to walk, created a difficult gap in his resume, and ultimately shaped the way he thinks about resilience, discipline, and telling a compelling story in the job market. He also explains what he learned at PitchBook, why that experience gave him such a strong foundation in sales, and why he was drawn to startups over larger, more established companies.
We also get into how Grey landed roles at Sunset and Default, why networking and staying close to people over time mattered more than simply sending cold applications, and what candidates should actually look for when evaluating a startup. Grey breaks down the appeal of joining an early team, the tradeoffs of startup life, and some of the most common reasons startups fail, from founder conflict and poor capital management to losing touch with the customer. He also shares why candidates should backchannel current reps, ask much tougher questions in interviews, and treat the interview process as a two-way vetting process instead of just trying to prove they deserve the job.
TOPICS WE COVER
- Grey’s path from nonprofit work into tech sales and why his career path was anything but linear
- How a major injury and long recovery created a resume gap and changed his perspective on work
- What Grey learned at PitchBook about discovery, product positioning, customer curiosity, and outbound
- Why startup sales appealed to him more than staying at a larger company
- How Sunset first became a prospect and later turned into a career opportunity
- How Grey got his role at Default through networking and relationship-building over time
- Why LinkedIn DMs, networking events, and staying in touch can create real job opportunities
- What to look for when evaluating whether an early-stage startup is actually worth joining
- Common reasons startups fail, including founder disputes, careless spending, and weak customer feedback loops
- Why job seekers should ask harder questions, talk to current reps, and treat interviews like a two-way evaluation
ABOUT THE GUEST
Grey Bradshaw-Mack is on the GTM team at Default, a New York-based startup, and previously worked in sales at Sunset and PitchBook. Before entering tech sales, he worked in the nonprofit world, giving him a nontraditional path into software sales. He's also an investor in Mercor.
LINKS
Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Default: https://www.default.com/
Carter (00:01.134)
Hey Gray, so give the people a little intro. Who are you? What do you do now?
Grey Mack (00:01.48)
Thank
Yeah, no, thank you so much for having me on man. I'm so excited so happy when you reached out background
Very quickly, went to Wesleyan University, graduated in 2017, managed right after school to find a really wonderful job at an amazing nonprofit organization here in New York. Have taken a very circuitous, very atypical path, I'd say, into the world of software sales. I have held three kind of formal roles in tech sales, if you will. The first at the company PitchBook, really wonderful organization, had a ton of great experience there.
left there to go and I cut my teeth in the startup world, joined an amazing early stage startup based here in New York called Sunset. was leading up sales there for about a year and a half and then most recently in the fall just joined another incredible company based here in New York, a series they started called Default. So, excited to get into it, excited to chat, excited to meet you finally and yeah.
Carter (01:07.062)
Yeah, and that's what I wanted to ask you about. You have done a lot of different things. Did you have an ultimate plan or was each move a pivot basically every time?
Grey Mack (01:13.942)
A lot of this stuff was just personal exploration. No, I don't think there was much of a very clean path the entire time. If there's a logic to it, it was only really found in retrospect, looking back. But...
Carter (01:43.992)
Yeah.
Grey Mack (01:47.83)
you know, sequential jump, like Michael J. Fox out into my kind of period of self-exploration, going out and doing my own thing, checking off some big stuff from the bucket list, post that, getting to Pitch Book, that was very intentional, Pitch Book to Sunset, very intentional, but overarching, you know, career goals, career path has been, yeah, has been a bunch of experiments that I think have led me to a really great place, but.
Carter (02:16.864)
Yeah, that makes sense. You, wanted to talk about, saw you had a serious injury that took you out for six months. You had to relearn how to walk. How did you navigate reentering the job market after that? Did employers look down on that job gap or did it give you an awesome story and they were, well, awesome maybe is not the right word, but did that story, did that story help you at all?
Grey Mack (02:37.013)
Yeah, no, it's a great question, man. So yeah, for the listeners, big kind of update was when I was 25, I rolled out of my work at the Michael J. Fox Foundation. I was on the side actually building a project with a friend that started to take off a little bit and, you know, bring in
a, let's call it supplementary income that had me feeling comfortable to take a step away from work for a little while. And I used that money to go.
go do a bunch of stuff that I had always wanted to do growing up. The first of which was literally get into my car after, you know, leaving my job and drive across the country aimlessly, attempting, you know, pointing my compass very loosely at California and saying, let's just stop anywhere interesting along the way. And in one of those kind of side quests, if you will, I went to a really wonderful ski mountain up in Tahoe, literally saw a little sign that just said, hey, you want to ski for free every day?
you know, save this year and apply to be a lifty. And as I mentioned, maybe, you know, before the call got started, I'd gone to Tahoe by way of being in LA and I started to grow tired of like being 65 degree and sunny.
So decided I was going to take that wonderful ski mountain up on their really attractive offer to go ski for free every day. So I applied to go join their lift operations group and worked as like a ski lift operator and ski school instructor and did a whole bunch of random stuff around the mountain. It was wonderful, but it caused one thing to happen, which was me to get way too cocky about how good of a skier I was. And in one of the last days of the season, I went out for
Grey Mack (04:28.982)
for a run that resulted in me breaking my neck, my back, both my hands, my foot, my knee, and a couple other things. So I was quite literally that dude in the cast in the hospital, all done up on bed rest for a few months. But yeah, to kind of answer your direct question, man, like navigating the workforce after that injury was intense for a bunch of different reasons. Of course, there's like, you know, sort of the emotional physical trauma that an injury like that puts you through that.
I had to, you know, I to kind of get through. But then, yeah, maybe to kind of your last point in the question there, like, there's a gap in the resume. Most recruiters, most hires look for like some continuity. It was definitely something that I had to kind of confront head on. And...
Carter (04:59.223)
Right.
Grey Mack (05:19.342)
I think one thing you learn, God, lights are turning off everywhere. I think one thing you learn in sales is that it really comes down to how you tell your story, how you spin your story. And I was able to, I think, take that experience and convey to any hiring manager that I was capable of doing really hard things, right? I was capable of coming back and spilling a ton of resilience.
You know, definitely, were questions raised about it, but it wasn't something that I couldn't overcome. yeah, when I look back on it now, mean, so much of that injury recovery period was, you know, again, incredible in hindsight. Like,
really test who you are as a person to get that low. And I don't know if you've ever been through a pretty hardcore nasty entry before, but.
Carter (06:16.465)
Nothing like even close to that. No
Grey Mack (06:18.794)
Yeah. And it's, you know, I will say like if I'm, if I'm doing the classic, you know, LinkedIn post of 10 things I learned about B2B SAS for my time, breaking my neck, in a recovery like that, everything is about like the day that like the, the daily discipline to do the little inputs, the thousand and one little foot raise exercises that feel totally arbitrary. And I know you were an athlete back in college. I was too, like people who, you know, have always felt a comfort in their physical body.
having to like retain that and just kind of like push and trudge your way through a miserable period. mean man, taught me so much about what I'm capable of dealing with, taught me so much about how disciplined I can be. And on the other end of it, I'm here running, I'm here walking. Like you know, even temporary pain is not permanent. anyways, long ramblin' answer there but.
Carter (07:16.022)
Yeah, but yeah, that's, that's nuts. And then, so after that you went to pitch book. Pitch book's a big company. It's a well-known name in sales. What did you learn there that you've carried into these startup environments?
Grey Mack (08:43.496)
Listen, Pitchfork taught me a lot.
I think in a lot of ways it was the place where I learned a lot of my like foundational sales skills. So how to run a sales process, how to do discovery, how to do product positioning and demonstrations, how to manage closing and transitions and handoffs to CS. And again, when I look back on that time, I'm like, that's really where I started to learn a lot of these like foundational sales skills for the first time.
There were also some really unique aspects to PitchBook's motion that I think translated and carried over really, really well to startups. On the one hand, there's a really deep product with a lot of applications to a bunch of different people, which required you to get...
in order to be really effective seller, you had to become really curious and you had to really learn, hey, if like a small corporate business that's going to do &A is looking to bring on PitchBook, how exactly are they going to leverage a tool like this? And I think that exact kind of thinking, that frame of mind is like the exact thing that you need to carry over into early stage startups, like an obsession with the customer, like as best as you can, a deep, deep understanding of
their day in, their day out, their workflows, the things that keep them up at night. Because, you know, at the end of the day, when you're a startup, what you're really trying to do, and what you're essentially doing is you're making a bet, you're saying, hey, you know, I think the market needs this thing, this new thing that I've created. And especially in early stage sales, lot of it's like just going out and validating whether or not that's true, right? So you're like,
Carter (10:30.702)
Mm-hmm.
Grey Mack (10:38.58)
You're saying, Hey, I made this thing. think you, I think you should want to use something like this, but like, help me understand how do you approach this? How does this resonate with how you think about how your job should look or how the team should run? And I think if I had started at an org that, you know, maybe had like a very discreet product that only sold to one type of customer where I could maybe just like, you know,
you
memorize a script and learn a couple of things about how, you know, B2B marketing works. Like I maybe never would have developed that habit, you know, if you will, that frame of mind that says like.
Carter (11:24.449)
Yeah.
Grey Mack (11:27.6)
get really really close to the customer, really learn. And then one other thing that I'll just call out here too was, know, PitchBook was a really big organization. They had a really big sales organization. I think, you know, in the few years prior to me joining, they had done an absolutely amazing job executing their go-to-market strategy and really going after, going after and winning the business of a lot of the core logos that they, you know, attempted to go out and get or that they could possibly serve.
I joined, you know, it was a culture where like there was inbound, sure, there was some amount of like leads being fed to you, but you also had to go out there and get it on your own, right? And like you had to be scrappy, you had to have the discipline to go work all your inbound deals and then constantly be building your own pipeline in the background. And the same thing, you know, the same mindset kind of holds true at a startup, right? Like
Carter (12:02.766)
Mm.
Grey Mack (12:26.134)
When you're a startup, you don't have the luxury of having a brand or having a huge gravity often to your business. You're often not drowning in inbound leads and you have to go out there and sell the vision and pitch. So yeah, think developing an outbound muscle is a really big thing that I learned at PitchBook that's carried over really, really well to startups.
Carter (12:50.752)
You know, I'm curious because now your last two roles are at sunset and default, which are both startups. Why startups over bigger companies? And then what do you look for when you're evaluating those startups, whether it's worth joining, whether the company is going to fail, you know, in six months? Yeah.
Grey Mack (14:12.682)
I think the appeal of...
coming into an organization, establishing frameworks, being in a really high leverage position, Like knowing, I think both at, especially at Sunset and now somewhat so at Default, you're coming in and you're joining a team that doesn't have really anything in place. that was a really exciting challenge when I was looking at it initially.
And I think what's kept me in startups is the, yeah, it's just like the ability to come in and just be able to make a big impact, test and experiment. mean, you you often hear like the same kind of cliche story from folks that were previously large orgs and joined startups. I think, you know, many of them felt similar to me that like when you're in a bigger organization, there's, you know.
there's benefits and there's drawbacks to it, right? Like there's proceeding and sometimes there's the feeling like you're just kind of a cog in the wheel. And when you don't necessarily agree with the direction the company's going in, maybe like you realize you have no ability to kind of change that, right? It's like outside of your control. And yeah, my actually my story of like finding Sunset and getting into startups in general was actually somewhat ironic.
Carter (15:22.027)
Yeah.
Grey Mack (15:48.054)
in that I was actually, since it was a prospect of mine when I was at PitchBook, so I was trying to pitch that. Yeah, I thought through like a, you know, again, in the, in the...
Carter (15:52.401)
okay, nice.
Grey Mack (15:59.446)
In the vein of being scrappy, I was trying to think through potential alternative use cases for startups to get more value out of PitchBook's data set. Sunset was one of those ones where I looked at the fact that, hey, PitchBook tracks funding rounds for early stage companies. We can tell you the last time a company raised money. I was like, bet if you guys were to take this data set and do some interesting algorithmic predictive analytics, you guys could start to get a feel for who's not raised money.
in quite some time, right? Maybe you overlay that with like headcount decline and maybe you guys get yourself like a pretty hot list of companies that might be on the chopping block in the next six to 12 months hitting the end of their runway.
Carter (16:30.766)
Mm-hmm.
Carter (16:42.518)
Right. Cause they were this company, they help startups shut down, right? That's their, that's their whole thing.
Grey Mack (16:47.37)
Yes, the most ironic startup of all startups. The startup to end them all, if you will. Yeah, Sunset was a company that comprehensive shutdown services to businesses that were going out of, know, were no longer operating or trying to figure out how to no longer operate.
So I was trying to sell them on this idea that, you guys can use this as maybe a lead gen source or something to go power paid ads or other growth experiments. And the founder was like, listen, appreciate it. But we're trying to not be like the rest of them that fail. spending $15,000 on a software that may or may not be helpful for us doesn't feel like smart capital allocation, if you will.
Carter (17:32.769)
Yeah.
Grey Mack (17:34.836)
But we developed a really great relationship through that whole evaluation. And we stayed super close to each other. And very slowly but surely, he started to express that they were starting to see some real interest from the market. He was thinking about hiring out a team.
And he came to me and basically said, I were to hire a salesperson, what should I look for? And my naive self couldn't really put the two pieces together until after the call ended that he was more or less testing to see if this would be something that I'd be interested in coming to take over. So very long, way of saying.
Grey Mack (18:19.766)
Startups gave me, I think, this really wonderful opportunity to come in and make a huge impact and get my hands involved in a bunch of different ways in an organization that just working at a large company would take long for me to be able to do. So call it impatience, call it ego, call it me thinking I saw the writing on the wall, this was a good opportunity. I just decided to jump full in, yeah.
Carter (18:49.186)
Yeah, that's very interesting actually, because I was curious, how did you get your most recent role default? it cold apply? You know, somebody get recruited again, maybe you worked with them at, well hopefully I guess you didn't work with them at the, at the last place. but yeah, what, what, how did, how did that happen? Like anything tactical here for, people trying to do a similar thing.
Grey Mack (19:01.604)
It's actually...
Grey Mack (19:08.754)
Yeah, yeah, yeah. There's actually a really quick funny story on the, as part of the default job interview process, they had me come in for a interview where I was going to be pitching the service and the offering that I was currently selling, which was default, or sorry, sunset.
And as part of this, I had the founder of Default role play as if he on behalf of Default was evaluating Sunset because their company was gonna be shutting down. And I had this room with all the rest of the sellers and all the other people that were in the hiring committee hear me do this mock call with Nico talking about how Default's failing and they're having to shut down and he's dealing with all these problems. And we get to the end of it and he was like.
You did such a good job, but I am so depressed right now that I can't give you feedback. Anyhow, how Default came about was... Yeah, yeah, yeah. So I think you can never underestimate the power of quick connection. So I met some of the Default guys at a wonderful networking event here in New York.
Carter (19:58.224)
Right.
Carter (20:05.644)
Yeah, how did that happen?
Grey Mack (20:24.928)
think about 10 months before I joined or even saw that they were hiring for the role. I think somebody who's looking to have a career in sales and especially somebody who's looking to break into sales.
would do well to embrace either like virtual or physical networking events as much as possible because, you know, what was like a 20 minute conversation at that networking event led to us exchanging numbers, led to us following each other on LinkedIn, led to us, you know, staying in touch and engaging with each other from time to time. And when I saw, you know, kind of job posting alert come through that default was hiring, I applied and managed to back-chain.
with a lot of the people that I'd already known to say, I'm really interested if you could put in a good word that would sort of mean the world. And so I think in a lot of ways, similar to my experience joining Sunset, this was kind of a relationship I started with no expectations that it would go anywhere or that it would lead to anything in particular for me. And by just keeping those doors open, it led to something that I'm
just incredibly grateful to be sort of here and along for the ride. But yeah, if I'm like trying to give tactical advice to anybody young, anybody who's, you know, trying to break into sales, I think like, you know, the old Dale Carnegie expression of like, everybody loves talking about themselves, right? Everybody loves people who are interested or express interest in who they are. If you're new to this,
and you're not currently in sales, reach out to somebody who is and say, I think your career looks really interesting to me. If you're ever interested in having a call, hop on my podcast, sitting down for coffee, and just having a chat and hopefully build a little bit of relationship there. You never know how those things are gonna boomerang back around and show back up in other stages of your life.
Carter (22:29.134)
Well, and tell me about these networking events, because any time, maybe New York City, there's a lot more going on there. But any time I've been to a networking event, it's just bums, basically. Not to be a hater, but it's basically just bums. So I'm curious, what are these virtual and networking events you're going to? How are you finding these?
Grey Mack (22:44.616)
Yeah, listen, know, New York definitely has the luxury of there being quite a few more events to go to. My experience has been much the same, man. Lots of times you go and it's, you you're kissing all the frogs on your way to find the princess, so to speak. But.
Carter (22:50.797)
Yeah.
Carter (22:56.268)
Right.
Grey Mack (23:01.342)
No, think, listen, there's some really great online sales communities that I tend to engage with. Companies or organizations like Pavilion, they're really wonderful. They host a lot of great stuff. They have a really engaged online Slack group that I often will jump into. in there, there's multiple different channels for people who are both searching for jobs, people who are hiring for roles, people who are new to cities or new to industries and are just looking to network with other folks.
You know, I think the advice I would give to anybody is kind of dependent on where they are. But like, you know, for example, I have a younger brother, he's 22. A bunch of his friends are graduating college right now and a lot of them are looking to break into sales. And, you know, I'm like...
Do not underestimate the power of a LinkedIn DM, right? Like you see somebody working at a cool company in a role that you can see yourself being in, reach out, share a little bit about you and a little bit about your interests, but like have the focus be on them. And I think...
Yeah, I think finding interesting people online and reaching out to them or engaging with their content and seeing if you can get them to respond and get them to engage with you, that's one huge way. I think there are really wonderful online sales communities that anybody who's aspirationally trying to get into sales should go and look up.
And then, yeah, the other thing is like they should anticipate that there's going to be, kind of to your point, like lots of dead end chats, lots of conversations that don't work. Lots of people you meet where you're like, this doesn't feel right. I don't want to learn from you or whatever. And yeah, it just takes like time and effort and discipline and, you know, yeah, just going through the motions over and over and over. eventually I think eventually you all, you know,
Carter (24:34.083)
Right.
Grey Mack (24:55.722)
You almost always find somebody who sees something in you, whether it's a younger version of themselves or they see potential or they see something about your story that really lands. I think a lot of people underestimate how much folks are interested in supporting others and bringing them along and opening up doors. I think you just got to take a long-winded answer there.
Carter (25:24.974)
Well, no, that's really good. That makes a lot of sense. So final question, I was really curious about this. How are you an investor in Mercor? Tell me that story. And this is 5X since you invested, right? So have you made a fat bag on this now at this point?
Grey Mack (25:39.2)
Yeah, it's funny. remember when you you you chumped me the note ahead of the call about how you'd want to bring this up and potentially some takeaways for for other folks that are curious about angel. I think I think listen like with any risky asset I mean to answer your question if I've made a bag it's on paper it's not in my wallet so there are two things I always say when it comes to angel investing you know
Carter (25:48.952)
for sure, yeah.
Grey Mack (26:04.126)
never bet more than you're willing to lose, because as my experience at Sunset so clearly showed, vast majority of pan out to do nothing, right? Most of them fail. Most of those checks are just like, you know, getting thrown into the wind.
Carter (26:12.95)
Right, right, yeah.
Carter (26:18.786)
But do you have to know, I don't know anything about it. Do you have to know somebody or I can just write a check into any, any private company basic for the most part, unless it's they're up to a certain stage.
Grey Mack (26:29.684)
Yeah, usually you need access in some way, form. The greatest access is directly to the team itself, so you can kind cut through the middleman. And when I say middleman, there's sort of two ways to typically go about it. There's a lot of tech platforms that are out there aggregating access to early stage startups, sometimes in the form of direct investments, other times in the form of secondary as rates to try to create options for early employees to exercise.
their shares and sell them off to the open market. The other intermediaries are often people who organize and fundraise for things called SBVs, which I'm sure some of your listeners, you are probably familiar with. Now, yeah, SBVs are special purpose vehicles. They are a...
Carter (27:13.908)
No, not at all. have no idea what you're talking about.
Grey Mack (27:22.666)
I think the easiest way to think about them is if you imagine a cap table as a spreadsheet and it's just a bunch of individual rows representing individual investors or funds investments into the company, an SPV is like one row on that spreadsheet that if you were to click into it, it would represent a whole bunch of different investors. So they're basically these little vehicles where a bunch of small people can come together or smaller checks can come together to make up either a minimum investment
Carter (27:35.789)
Right.
Grey Mack (27:52.82)
or a particular allocation target that somebody has. And so what very frequently happens in kind today's fundraising world is people with access will be told by a company that they could put anywhere, let's say for simple math, half a million dollars into a route, right? But that individual themselves may not have half a million dollars liquid to go put into that. And what they'd rather do is go out to other folks in their network and say, hey, are people interested in investing
a small check to help us kind of fill up this allocation that we have access to. We will funnel all of these checks, this whole investment into an SPV and that SPV is gonna go invest into the company. There's a bunch of like absolutely incredible resources online to go learn about SPVs, to go learn about people who are organizing and collecting. They are...
riddled with their own set of risks. like, know, investors beware, certainly not financial advice to go look into it. But yeah, anyway, very, very long-winded way of saying, Meriport came together again through like a, you know, a random happening, a pretty random connection. I had met at a networking event at the SF Tech Week programming.
It was a young kid who was, his basic thesis was he was like, I'm a Gen Z builder interacting and engaging with a bunch of other Gen Z founders. I have direct access to a lot of these companies and these people trust me. And so when they go to raise money, they often look to me and ask if I want to get involved. So this like young, cool, interesting 22 year old kid that I met at this, you know, this again, networking event.
kind of boomerang backed around into my life really randomly and was like, I have this amazing investment opportunity for AmeriCorps. If you're interested in getting in, here's more information. I can get you access to the team. And yeah, again, man, it was just like a very random conversation that led to me getting access to what hopefully is, say, we'll be a generational company here.
Carter (30:03.402)
Yeah, that's very interesting. seems like it's worked out so fine. I used it on paper, but it seems like it's going pretty well so far. that's pretty, yeah, that's pretty interesting.
Grey Mack (30:11.37)
Yeah, dude, mean, listen, I think, again, all it's gonna take a while for me to probably see the fruits of that labor. Five X on paper is great, but it's on paper. And yeah, I try and do, I try and stay close.
to what's going on in the market. And I'm involved in a couple of these different like angel syndicate groups where, you know, different deals are put in front of my desk, you know, weekly here. You know, like any discerning investor, I'll pass on 99 % of them and invest in a very small portion. I think like,
Carter (30:51.309)
Yeah.
Grey Mack (30:55.99)
There was a question you had asked earlier that I remember right now that I didn't fully answer here. When you're getting into early stage startups and you're trying to think about how you should evaluate these companies, what you should be looking for.
Carter (31:06.53)
Yeah, yeah.
Grey Mack (31:12.468)
I had the privilege of being at Sunset where I got this pretty cool, interesting pattern recognition developed around what companies tended to do on their way to failure, that I was able to reverse engineer in a way and say, okay, let's make sure that they're not doing any of these things and let's actually assume the inverse. And if we can see that they are doing some of these things, that probably signals a sign of success.
Grey Mack (31:45.588)
You never know. Like at the end of the day.
Carter (31:48.386)
That's the moral of this story. Well, I'm curious. Okay. I know I've had you on here for a minute, but what are the re what are the reasons they go out of business or there's there like a list of things.
Grey Mack (31:56.01)
Yeah, yeah. Listen, I think companies that...
So a couple of reasons. Founder dispute is a very common one. two of the co-founders having mismatched visions as to where the company is headed or what the direction of company should be, that can often lead to deep fissures forming in the foundations of the business that become insurmountable. I think companies that have relatively careless capital management practices is another thing.
you know, even if it's like don't invest in really great accounting, you know, foundations or are not particularly discerning about like the way they've, you know, fund their business. You know, that often ends up being the case or that often ends up leading to a downfall or can lead to a company failing.
Grey Mack (32:55.126)
What else man? I used to have such a loctite list in my head. It's been a little while.
Grey Mack (33:06.9)
I mean, on average, first-time founders tend to have a much harder time than repeat founders, kind of succeeding on their first go-around. There are obviously exceptions to that rule, but in many cases, know, lots of like repeat entrepreneurs tend to be a lot more successful than first time. I think, you know, there's some like behavioral patterns of companies that
that we can also signal high likelihood of failure, which is like not staying particularly close to the customer, not iterating and shipping really fast, spending too much time developing and building based on their own assumptions rather than like putting something out to market and using actually tactile user feedback to determine product roadmap and things along the like.
Grey Mack (34:01.783)
And what else? There are...
There are so many things, man. But I think if you're outside looking in, trying to evaluate a company, trying to figure out, is this startup for me? Try and get.
as many points of reference within the business as possible. You know, I think something that many job seekers often underestimate is how much access they have they're entitled to when they're going through their interview process, Meaning like so many folks think it's about...
them proving that they're a fit for this company. But I think it's equal parts the onus of the business as well as the individual vetting the business to do the absolute inverse and say, have the company prove that it's the right place for you and that it's the right place for you to your career on. So you should feel entitled to ask hard and tough questions. How much runway do you guys have? What's your hiring plans? What's your fundraising strategy?
How do you think about, you know, performance management and, you know, tell me a time where you guys hired somebody and it didn't work out. How quick were you guys to realize that and resolve it? Because, yeah, I think like so many people...
Grey Mack (35:34.102)
So many people can look at a startup and fall victim to the things. Yeah, no, I don't know. Hopefully some of that's helped.
Carter (35:44.13)
Well, I get what you're saying though. Yeah. Cause they look cool sometimes. Yeah. Who, if I'm talking to a startup, I have no, I see what they are telling me and I can look online and they look cool. So I think, this, this seems good. But yeah, that, so that makes, that makes a lot of sense. Cause you're right. It's a lot of time you're going to spend working for somewhere. You don't want to work somewhere and they just die in like six months. That would be bad.
Grey Mack (36:02.954)
Yeah, man. to your point, the tough reality about startups is every idea is actually pretty good. Very few businesses fail because the idea was just flat out bad. Most people who become founders are smart, fairly obsessed about a particular problem, have really thought something through in depth enough to make them feel like, they should go bet their lives on making this thing happen.
So yeah, to your point, you're online, you're looking at a website, like lot of startups look great from the outside, but.
Carter (36:38.286)
Alright, and they've raised millions of dollars, yeah, who's to say?
Grey Mack (36:41.61)
Yeah, and like, if you're talking about particularly in like a sales context, if you're interviewing for a role, like go back channel and talk to every rep that you can that's at that company and like ask them really candidly about how things are going. How's the team performing? What does pipeline look like? What's quota attainment look like? How is, you know, management's approach to working with sales? Is there leadership? Is this the place where like,
I can step in and learn from somebody who's really proven and done this. Or is it like, perhaps like a guy like me when I was at Sunset, where this was my first go around being the founding sales guy. For a kid fresh out of college, that might not have been the best learning environment for them. I guess what I'm trying to say is you should really dig deep. You should really try to talk to as many people.
Carter (37:30.05)
Yeah.
Grey Mack (37:38.602)
because startups are not, you know, they're not as glamorous as they look from the outside in, I'll tell you that much. At least not every day.
Carter (37:47.308)
Yeah, no, that makes a lot of sense. Well, I think we got some good stuff here. I'll end it right here.


