Lenny's Podcast / episode intelligence
Speakers in the public record
Claim mix
Evidence policy
Every row below preserves an exact excerpt. Identified speakers are linked; unresolved voices are labeled and excluded from people counts.
Claim ledger
22 published records
01 / belief
“Oh yeah, I think that a lot of companies, sorry, a lot of folks that serve the enterprise, they have a butt in a seat in their office.”
02 / uncertainty
“Again, they do this one in every three years, one in every two years, maybe one in every five years. Hell, I don't know.”
03 / belief
“I think that that's the best type of salesperson because it doesn't feel like sales.”
04 / belief
“Do you want to buy from this person? I think Jason, Jason Lemkin said that best.”
05 / belief
“You got your foot in the door and you can expand it exponentially in a healthy manner. I think that that's fine.”
06 / belief
“One of the biggest fears I think founders have is having a company pull, basically build just for their use case and then it ends up not being used by a lot of people.”
07 / commitment
“I will not get in on another call with someone because on the first call it's either a yes or a no, there's no in between.”
08 / uncertainty
“There's a lot of companies out, I'm sure OpenAI, and this is what someone told me they were in and talking to CTOs and helping them better understand how AI and their organization can better work together. And it was them coaching them, educating them, whether they did it for free or not, I don't know, but they got their foot in the door, they started to build trust and then it gets adopted.”
09 / belief
“There's the obvious companies that everyone is always trying to get these days, OpenAI and Anthropic and Stripe I think is one.”
10 / belief
“Either pick SMB small company, which I know you said there's a million ways to differentiate what this means, but I guess I think of employee numbers under some number over a thousand is maybe enterprise.”
11 / observation
“In the very early days, people will discount till the cows come home because they think that's the way to get a deal done.”
12 / prediction
“What is the opportunity that you're selling? That if they are excited by that, they will take a call.”
13 / preference
“A VP of sales at a large company, I would say, they're best suited for a large company because one to 10, you're running through walls.”
14 / evaluation
“I think about linear, which started very startup-ey and my take is they did that because changing the way you work is really hard and their bet was like, "Let's start with companies and grow with them and over time that becomes the default.”
15 / prediction
“I look at headcount too because it's just such an easy way to think about it because you can also gauge usage off that and a bunch of other things, but sometimes the small companies, I think we're going to see a lot more larger companies become smaller because of AI, not significantly smaller, but also high margins allow them to experiment more too.”
16 / recommendation
“Maybe a former founder if you can get that, because they're used to selling, they sold investors and they've sold employees.”
17 / evaluation
“" That is the founder's job. And I think we did a bunch of design partnerships late last year and there was a lot of feedback given, a lot of feedback given, but the founder had such clarity with where he wanted to go that he was like 80% noise, 20% had I not asked this question, I wouldn't have gotten that gold in terms of where they are today.”
18 / preference
“Think about it. So many people are so specific about what they're able to, I think especially technical folks, I'm not a technical person, but I would imagine that they're not going to go to, they don't like to go to these corporations because they're forced to use some incumbent tools.”
19 / evaluation
“It's fascinating because if you ask someone to describe the mid-market, actually, if you ask someone to describe the enterprise, every single person has a different answer. It's either based off of revenue, it's either based off of market cap, it's based off of employee size, and I think a lot of people can get lost because selling to a hundred person organization is a radically different game than selling to a thousand person organization and there's no hybrid approach.”
20 / evaluation
“It's not on email anymore. It is a relationship you're building with someone where if my enterprise client called me, I'm picking up that phone immediately or I'm responding them to immediately because that builds so much trust.”
21 / recommendation
“It's about selling the opportunity. That's what gets the tier one logos excited and that is the best thing for a founder to sell, selling the vision versus the problem, and also it's what gets them to want to take a swing.”
22 / preference
“I don't use a tool because I believe in the manual and I'll explain why. Every single note I send is slightly different because I see a picture of them and I'm like, "Oh, I don't know if that's going to land.”