The Ledger, every show

“The IPO bar is just spectacularly high right now. I think it's around five hundred million in ARR by my math.”

“The biggest thing I've learned about working with PE is I thought they were fixer upper people... And I don't actually think many of them like to do that. They want it fixed first.”

“A lot of times founders think it's not possible and give that company to a PE person. And I guarantee you they're going to have 20% EBITDA, maybe 30% EBITDA in a couple of years. It can be done.”

“I do think somewhere around 24 to 36 months people stop calling you back, so you have a different problem. It doesn't matter how good your story is if you don't get the meaning.”

“I think most startups, when they make that argument to me, I think they're vastly underestimating the size of their market. That if you have a really, really big market, That, that you haven't picked all the low hanging fruit.”

“And by the way, if you asked, like, the most recent study, I think, said one oh five. The reason I said one oh eight is I just can't make my mouth say one oh five. But I think it may have come down from one 20 to one oh five, to be honest, and I think it's thr…”

“The single biggest sin in SAS is putting your farmer against someone else's hunter, right? Cause they will lose.”

“So, so I just think CS for it, I am, if a VP of sales misses their forecast, I'm somewhat understanding. To me, it's I'm not very sympathetic to a VP of CS that misses their forecast, because how is it that you didn't know?”

“The hardest case is not firing somebody who's not selling. That's easy. The hardest case is keeping somebody who's not selling.”

“If you're selling a 5000 dollar a year system to anybody, As a generic productivity tool, I have a lot more trouble getting excited about outdoor.”

“If and when you replace a founder, which was extremely unpopular for the last five years, but I think will get more popular going forward, you will tend to replace them with a GTM person.”

“Jason Horowitz, in my opinion, Put that trend on hold for a decade or more, right?”

“Well, you know, battery came up with a famous slide well now famous slide, but they basically said, I'm going to get the, I think to support 30 sellers, they argued that today it takes a 110 personal organization and that tomorrow it'll take 75. So they're say…”

“Hiring a VP on pedigree value who turns out just to have been in the right place at the right time.”

“I honestly don't believe that floggrowing startups, as they say, stuffing them full of cash is a healthy behavior. Some are actually good. I know a few that seem good at raising money and not spending it and saving it to grow later, right? But most people, whe…”

“Another friend of mine has this expression from Machiavelli that warring princes means one thing, a weak king. And if you're CEO of the company, you cannot allow warring princes in your company. Everybody sees it. The whole company knows if two E staffers are …”

“I did a year at Salesforce in the middle of all that, and I was mentioning Zendesk. I was like, hey, there's these guys called Zendesk, and they might be a problem for, like, our customer service business and I got the kind of uh-oh moment where, like, oh, and…”

“Avoid this fake either or framing, which is you need to speak like you're vision driven. So when you're talking to customers and analysts, the markets, talk about the desired end state. Talk about the vision. Don't talk about competition. When you're building …”

“First, you did not have on a quarterly basis in an enterprise company, 80% of your reps every quarter. You might have had 80% every year. You might, right? 80% at a hundred percent of quota on an annual basis is very good. On a quarterly basis, it's almost imp…”

“I've worked with many startups where the figure it out sales VP had to leave when we hit ten million. And I always feel bad about that, because I don't actually think they have to leave. I think they should be redeployed. Like, my answer is, what do you do wit…”

“In terms of second product, I talked about Jason Lemkin's work before, but he's done a series of tweets and blogs, and from his research to me, for most companies, it's probably a hundred million plus in ARR, and maybe multiple, for the companies I work with, …”

“Create your own agency or your own services org. Charge for it. Charge market rates. Maybe even a little more than market rates. Actually, not maybe. Charge more than market rates, and then build a partner network.”

“You're confused by ill-defined terminology and process, most marketers are not that rigorous in their thinking and you're drawn into conflict between sales and marketing, right?”

“Now to me, the best practice here is that marketing should be the quarterback of the pipeline, because if you think about those four funnels, the only person they all report to is the CEO. So either you're going to be the quarterback of the pipeline, or you're…”

“There's a semi-famous quote that but cash is a fact, profit is an opinion. I feel the same way about ARR and churn, that ARR is a fact churn, And churn rates are an opinion.”

“The R squared is only .O six between net dollar retention and enterprise value to next 12 months revenue.”

“So it's not a valuation driver. I now think of it as a financing enabler, right? Okay. So a higher one isn't necessarily by itself going to drive a higher valuation, but I could tell you if you don't have a high enough one, you're not going to be able to raise…”

“If you're in some horizontal platform category, people may throw hundreds of millions, maybe even billions, of VC at the category. And you don't get to not play. So, if you find yourself in this situation, it's probably a sign that you're in a really good cate…”

“If I'm not keeping the board busy, Helping me drive the company, they are going to come in with ideas and ways to help that I may not find helpful.”

“Avoid this fake either or framing, which is you need to speak like you're vision driven. So when you're talking to customers and analysts, the markets, talk about the desired end state. Talk about the vision. Don't talk about competition. When you're building …”

“By the way, for whatever it's worth, I don't actually think customer success should report to sales. I think that's a stress reaction to save money. I think the company hits a downturn. There's too much sales expense, which customer success is usually classifi…”

“Unless your business plan is predicated on price model disruption, do what everybody else does.”

“There's two ways to solve that problem. One is to have super consistent pricing, which in my experience in enterprise is very difficult. The other is to have very complicated pricing. So it's very hard for them to figure out who got the better deal.”

“An ICP, ideal customer profile. ICP starts out as an aspiration, and over time it becomes a regression, right?”

“I'd say a 1.5 or less is in enterprise. I mean, here we are back to your question. The bigger the deals, the more permission you have. So an enterprise, I might go one five. In SMB, I might go one O.”

“As an operator, I actually just do it on new ARR. My first order CAC is just, it's not net new, because net new introduced churn. You just made my metric more complicated, right? You made it easier to cheat. You took away some of its meaning.”

“Churn forecasting to me is actually easier than new sales forecasting.”

“And a good forecast looks like this, gently upsloping to the actual number you sell. Notice I've never talked about quota. Because forecast is not about quota.”

“Some sales managers use the forecast as a club to kind of push the reps around. Like if I could just in a moment of week is get you commit to one 20, then I can hold it against you for the rest of the quarter. First, I don't think that's great sales management…”

“So I like hiring three at a time but not for the Hunger Games effect, for the controlled experiment effect.”

“I would say somewhere between six and 12 months in enterprise.”

“As a CEO founder, I think you just need to look at the materiality of the deal to the quarter. And like, are you What's the word? But negligence in your duties. Like at some level, if the deal is material of the quarter, you better be in it deep.”

“You don't make the software. So your only job is to sell the software. You're not a technical resource. You don't help customers deploy. So this is kind of the, you had one job argument, right? Like you had one job. And it's like, let's just remember, that's w…”

“The company got acquired on the last day of the quarter, all purchasing got frozen. Okay! Right? That we couldn't have seen coming, right? But it needs to literally be that level of act of God, right, before It's before it's an excusable reason for a slip.”

“I don't love it as a negotiating chip because if I'm doing right by your business and if I'm delivering value and if we have a good relationship, you should do it anyway. And if you're only doing it because of a gun to your head, because you promised you'd do …”

“I think Outbound actually worked better four years ago than it does today, because I think everyone's doing it, and people are getting flooded with it, and they don't like getting called on their cell phone, they're not answering their regular phone, and you c…”

“I mean, I can summarize all of Jeffrey Moore in one sentence, which is people buy when they think people like them use your solution, period.”

“The other thing, so I imagine this all as a matrix of vertical versus use case, and every time you're hopping a cell, it's danger, right? Like you know how to sell the custom publishing use case to publishers. Can I sell it to airlines? First, the first one is…”