This transcript is an interview between Kevin 'KD' Dorsey and Kyle Norton discussing how to evaluate companies and leadership, when to 'quit' (reframed as 'fold' from poker), and practical signals to watch for after joining (customer churn, lack of transparency, senior turnover). Kyle emphasizes the value of mentors and networking for getting inside perspectives, cautions against jumping ship too early given macroeconomic shifts (interest rates, fundraising climate) and notes hiring-market changes—resumes are often weak and applicant pools are crowded. The conversation mixes anecdote, tactical advice, and references (Annie Duke's book on quitting and Thinking in Bets).
Chapters
So it's one thing to vet, but I want to go this route for a second, right? Like, okay, I vetted, did it. I got in there. When do I know? It's like, ooh, maybe this isn't what.
I thought it was going to be.
I love thinking in bets and how we think. Is this our third one?
I don't know. I've only read thinking in bets. This is just called quit. And for a poker player, quitting is a different framing because you're not quitting, you're folding. When is it time to fold this opportunity? It is natural to have to make very different and difficult business decisions. So just because your company's laid people off does not mean it's like, like going in the sewer.
What are some things I can do to vet the team, to vet leadership a little bit, to get a feel? Because, you know, it, like I said, it always sounds great, right? No one in the interview process is like, yo, I can be honest. RCO is insane, right? Like, they're always like, oh, like, oh, just brilliant. All that. So, like, what can I do to vet this if maybe I don't have that direct line to, like, the leadership team?
Such a good question. I would say mentors are your biggest asset here because I could give you information like, you know, you want to look at track records and trajectory and this and that. But, like, honestly, I've just had so many reps and I'm like, so obsessed with the venture capital markets that I. That, you know, I just know it sort of inherently. I think as an individual contributor in the first couple of years of your career, you're so right that it is a hard question to answer. Mentors are the most incredible resource in general, and I think in particular here it's important. So if you don't have mentors, go get mentors. And you'd be crazy surprised who you can reach out to just on LinkedIn with, like, compelling personalized messaging that was that those people will be willing to take. Take some time with you as long as you're an awesome mentee. I would go find. Find access people you trust. Everybody can know. Everybody knows somebody through one or two connections that you could access to. But I think that's where I would start if I was an early career individual.
Yeah, I like that because it is. It's like if you don't think to ask it, but then you don't have access. It's not like you get to sit down.
Right.
The CEO isn't necessarily doing that right now. I'M going to flip this the other way, and we'll keep going down this path. When do you know it's time to abandon ship? So, so, so it's one thing to vet, but I want to go this route for a second. Right. Like, okay, I vetted, I did it. I got in there. When do I know? It's like, ooh, maybe this isn't what.
I thought it was going to be like.
Walk me through that a little bit.
Yeah, that's. It's such a good topic. In Annie Duke's new book is all about this exact topic. Talking about, like, how quitting can be good. And she's a professional poker player. So, like, quitting is.
I love Thinking in Bets and how we think.
Is this our third one? I don't know. I've only read Thinking in Bets.
Okay.
Yeah.
Love Thinking in bets. And she has another one that is on, like, my shelf somewhere I haven't gotten to yet. But, yeah, so I think, like, how we think or something.
Okay. This is just called quit. The power of going on to walk away. And for a poker player, quitting is a different framing because you're not quitting, you're folding. And so we need to think about that in our careers as well. Like, when is it time to fold this opportunity? And so I would ask the same questions. Marketing product about your current company, and also get outside insight. And so things that are warning signs for me. You know, I've had a lot of career conversations with people from my tree the last bunch of months, and then one of this is sort of the advice that I give to them. Be really diligent on Churn. Like, if customers are churning like crazy and it's for product reasons, and there's not like, an insane desire, like code red type of hustle to figure those things out, then that's definitely a warning sign. Lack of transparency when a company is, you know, holds off from sharing information. So if your company's not sharing information on Burn and Runway and Churn and all of their success metrics, you know, you want to ask the questions, you know, ask your manager. Be like, hey, you know, like, curious. Like, you know, I know we've. We haven't really been hiring much lately, and this is going on. Like, do you know, can you share much what's happening in terms of our net retention rates or Churn that we've seen in the market? Like, that's a pretty big indicator, getting outside opinion on the caliber of the team. If you see senior folks coming in and out Especially if they come from like exciting pedigrees. Like, that's probably not a great sign. But you know, getting insight from folks around you. But it's a really careful balance because again, like the markets have been drunk the last couple years and I've never reviewed resumes, I've never reviewed so many resumes with so many nine month stints on them as I have in this period of hiring that I've just done. It is crazy. And I'm like, man, do I need to recalibrate like my expectations here? Because normally I see like two or three of those in a row. I'm like, oh, okay, no way. But so many folks that I've seen applications for have that. So you certainly want to be cautious of jumping too early. And just because your company's laid people off does not mean it's a bad thing. Because the markets were, the markets were affected by free money, free money and crazy money coming in from the Fed, which caused us, which caused interest rates and sort of the return on capital to be viewed completely different than it is today. And so companies were doing actually like normal things, invest like crazy in growth, Money's free. So your discount, acute future cash flows, like that equation is going to be different. When the cost of money is zero, when the cost of money is 5, 6, 7%, then as a business we are forced to make very different decisions because of the fundraising climate and all these things. So it's not that your company or your CEO is dumb or reckless or whatever. Actually, in that environment, those things are pretty normal. Reasonable, smart people could make that decision. Now that the market has changed and the economics of getting access to capital are so different, it is natural to have to make very different and difficult business decisions. So just because your companies laid people off does not mean it's like going in the sewer. In fact, the earlier they've done that and the sharper they've been to make those changes to set the company up for success, the better. And the zombies are the companies that are going to that won't have done it fast enough that didn't take that advice early enough. So you don't want to jump ship too early for sure, because like in challenging environments, great careers will be made. Like so much of my early career success was, I started selling in the 0809 recession. They fired a bunch of people. Then when we were rehiring, I was there as a top rep and I went over and above and we were growing again. So there was lots of opportunity. So, so there's two sides to this coin for sure.
And I'm glad you addressed that because I think it's something. It's been so easy to point and say, oh, they were being reckless with money, or, oh, it was bad planning. And it's like, look, no one at the start of 2022 had their bingo card out and said, okay, 9% interest rates, okay, or inflation, 7% interest rates, a war overseas, a supply chain issue. Like, no one had that planned for. And so the adjustments had to be made. And it does suck to go through, which actually does, I think, take me to the next point I want to make, right? Is like, okay, so now the hiring environment is different, right? You could, you could go get a job, be there for six months, and a recruiter would hit you up, and you go jump to that. Like, I know people that personally that went from like 100k OTE to like 250 OTE in one year by getting three different jobs.
Like, did they get hired from Shopify? Because this sounds like what happened to my reps. Like, I want to know.
Where they all ended up. Because this was happening everywhere, right? You could, you could just put your finger out and get a job. Now it's the opposite where a lot of people aren't hiring, or if they are hiring, they're 75 applications in the first how, you know, however many minutes of it going live. So what are things to do right now to stand out as an applicant? Because otherwise, you know, you're just getting buried in the resume stack. And it all, it all look. All resume looks the same.
We can talk about this later.
I hardly ever look at resumes. I just don't believe them. Like, everyone says great things on the resume. I'm like, I don't even need to take time to do this. So, like, as a candidate, you know, how do I get to the top of that stack? How do I at least get my foot in the door to give the opportunity to land some of the gigs since hiring is a bit tighter now.
It's funny you say that, because I've actually gone through so many resumes the last couple of months, and so few people have a compelling resume. I see so much of the time manage the book of business, met and with clients and demoed and closed business. Like, I don't care about any of that. Just, like, tell me the results. So I'm glad you're seeing better, better resumes than me.
No, I'm not, because I don't look. I. I don't even look at resumes ever. I do not. For the past three years. I never look. There's nothing for me to see that. Because either I am going to have a recruiter talk to them or I'm going to interview them. What you say on your resume does nothing for me at all. I just never even look anymore.
