The Ledger, every show

“If I was advising a young person where to go, if you wanted to found a company in two or three years, I'd say product, not engineering.”

“The great paradox right now is that people who are in subscription pricing generally have been hit harder than those who are not, but they're nevertheless still growing faster.”

“Because the VCs tend to be trusting and say, what's your CAC and tell me how you calculate it. And isn't that interesting? Whereas the PE people just said to say, give me all your data. I'll tell you what your CAC is fundamentally. Especially in the context of…”

“You know, a VC will look across their portfolio and think of the best CAC payback period, the best LTV to CAC, the best rule of 40, and ask you to do, you know, beat them on all four, right? It's inherently unfair. It's a form of bludgeoning, right?”

“The change management is hard. It may require staff upgrades, particularly key analytics roles like RevOps, FP&A. Sometimes those people are not that strategic. They're not that fast, right? That they're good at making a budget and they're good at getting comp…”

“In 2002, there were only two types of startups in existence. Those that had raised a large amount of money at a ridiculous valuation prior to April 2001, or dead. There was no other type of startup in 2002, when the internet bubble burst.”

“You might go out thinking you're gonna raise twenty-five million, and in this world, find out that you can raise 50. Should you take the 50? In my opinion, yes.”

“So, if you find yourself in this situation, it's probably a sign that you're in a really good category, but you either need to play to win, and go out raise the other guy, or you need to find pivot into some sub-segment where you're not directly competing with…”

“And this notion of having a sell by date, it may not be polite, but often board members have it, and if they have it, I'd advise you to understand what they are. And to try and reframe the issue that it shouldn't be that John or Mary is with the company or not…”

“The last three I just exclude is politics, period. Because what you're saying is you want your function to be more important than the other function. So I throw those out.”

“Their OTE, their on-target earnings, is 300 K. They're gonna cost a 180 K for two-thirds, and you can adjust these numbers to your local market, but do the exercise, right? So I'm hiring a seller. I'm hiring two-thirds of an SC. I'm hiring two-thirds of an SDR…”

“Scaling is very different. It's about a small number of amazing process and infrastructure oriented leaders leveraging a large number of great, but not necessarily amazing people, right? They're not solving problems. They're building systems and processes. Qua…”

“Anyone with an idea is trying to help, and your job is to listen, to understand the idea, and then by and large not do it, right? Because if you have a good plan and a good strategy, you need to go execute that.”

“Americans always inflate their resumes, and Europeans are pretty modest by comparison, and that's a terrible intersection, right, because you have someone who's kind of modest interviewing someone who they think is modest, and that person has created this resu…”

“A lot of people do NFL cities, which I think is a terrible strategy, but you could do that if you want. Just, if there's a football team, put salespeople there. Not, not my recommended one, but people do it.”

“Don't hire a VP of sales, hire a director. And let them try and earn the job.”

“I actually believe private equity people are better than VCs at solving it, right? Because that's what they do for a living. They buy old, not those super big ones like Tomo Bravo or Vista, but the smaller PE firms who buy, kind of, 20 to fifty million dollar …”

“If you go that route, then you got to be careful because if it gets too big, people are going to say, you're not a software anymore. You're not a software company, Nick. You're a services company pretending to be a software company, right? So you have to be ve…”

“So, in my opinion, the founder experience that happens a lot is you found a product company, and one day you wake up and you're running a distribution company, and you go, what happened?”

“The fact of the matter is, if you're talking to your buyer, and it's a high consideration purchase, they will have time to read a twelve-page white paper. They will have time to go to a one-hour demo, right?”

“I think the number one mistake I've seen founders make is they hold people's feet to the fire on all those cells, and I think that's wrong. I think it's demotivating. I think it doesn't reflect an understanding of the fact that the model deviates from reality.…”

“There's nobody who's a five-five. God doesn't make them, right? You either grew up in product marketing, or you grew up in demand generation, right? You also don't get 20 pointers. I think 15 is the maximum number of points you can get on this scale.”

“The ability to raise money is what separates the winners From the runners up and the losers.”

“So to me, controllable versus uncontrollable churn, it is a concept people talk a lot about. But I get super uncomfortable because I think it could easily be a cop out, right? You know what? Like my last company, they got a new CFO and they didn't renew. We ca…”

“Customer success, in my opinion, does not belong in COGS. They, it belongs in sales. And most companies will put customer success in sales.”

“To a certain extent, I'd also stop doing multi-year deals, because if you're giving someone a price lock for a multi-year deal and they're not renewing, you gave something and got nothing.”

“And one of the things VCs do is pattern match, and if you don't channel their energy, you are likely to be pattern matched to death.”

“The last three I just exclude is politics, period. Because what you're saying is you want your function to be more important than the other function.”

“The low-hanging fruit on efficient growth is a dispassionate, calm analysis of what sectors do we sell to.”

“Now, I think the difference between a salesperson and a marketing person is I tended to be more theoretical. What is correct? What is right? Whereas a seller is reading the room very closely. Who cares about what? Who has what interests?”

“If I were screening companies I would, I tend to want to use compound metrics. The more I'm trying to fix broken things, the more I want atomic metrics.”

“In my world, there's three different types of calls. Let me just define them. I think the There's a forecast call, there's a pipeline scrub, and there's a deal review. Purpose of forecast call is to come up with a forecast. Should be all numbers. One of my sid…”

“By the way, everyone should have a closed plan, and every time you hear one of those excuses, it should go on in the closed plan.”

“Selling through curiosity is just amazing, because most salespeople are, in some ways, they're too busy trying to prove how smart they are, be tough and confident, and it's just so humble a place to come from”

“There's a great metaphor, Harry, which is when do you stop squeezing a wet rag? When the water stops coming out, right? So as long as there's water coming out, I'm going to keep squeezing, and then even then, when the water stops coming out, what do you do? On…”

“Look, vertical strategies work, because the people like me effect, they're inherently limited, and they're a little bit high cost, because you now have to learn a lot about all your customers in that industry”

“So if I were a founder of one of these companies, I'd be very aggressive right now to get myself known and established in the market, because this market will organize, right? We're in the chaos phase of the market, and so from the vendor side, this will organ…”

“They think that the product will work in enterprise without understanding the requirements.”

“I think if you ask why questions about how decisions got made, you tend to find out if they were making them.”

“The most common form of misleading is what I call cherry picking, right? You just don't put up the bad numbers, right? You put up different numbers every quarter.”

“And when I give the forecast to the board, I want to give a 90% confidence interval. So I'm giving them the lower bound of a 90% confidence interval. Now people hate that. And if people get scared when you use those words, I have advice. Just say you get to mi…”

“I have one of my MBA is recalculate everything. And I'm like, this is a symptom of a very serious problem, right? We don't trust the management team to present the correct numbers. We don't correct them to do the trust them to do the right formulas.”

“If the top two important numbers are not being achieved and you can't see why in all the other numbers, I can't diagnose what the problem is, but I can tell you have a problem and it does happen from time to time.”

“The symptom is very simple. You go to a board meeting or QBR or management meeting, and the only two people who ever asked numbers, answer numbers questions are the CFO and the head of rev ops.”

“That's going to drive your CAC up because CAC is a function of growth rate in enterprise software because you're carrying unproductive slash ramping resources, right?”

“I actually think the best way to segment them is by aspiration. That, that if we could, and nobody offers these yet, but I want you to just consider this concept that we should segment benchmarks by aspiration, which is if I want to sell for 18 times EBITDA in…”

“I competed against the company that did one dollar renewals. And they would juice their churn rate so they could offset their SAS metrics.”

“Even layer one has taken me with certain companies I work with quarters. And I walk in every time I have this kind of entrepreneurial blind spot going, this is going to be easy. Me, head of FP&A, CFO, we'll get this nailed in 30 days, 60 days. Every time I do …”