Knuckle Up with Nakul

Raw conversations with elite operators.

Recruiting. Culture. Intensity. The inner game of being a CEO.

Hosted by @nakul. Presented by @AudaciousHQ.

[Knuckle Up with Nakul @KnuckleUpHQ]

Building a company is a confrontational act.

Introducing Knuckle Up with @nakul: conversations with people who’ve operated at the highest level.

Recruiting. Culture. Intensity. The inner game of being a CEO.

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[Knuckle Up with Nakul @KnuckleUpHQ]

How Juicebox plans to stay ahead now that AI lets every competitor ship fast. David Paffenholz:

"Short term it's all about good execution. Are we making the right product bets? Are we shipping them fast? How fast are we scaling go-to-market? Are we going upmarket faster than competitors?

However, that's only a short-term thing. That's like the sprint part of the race... And so then the second part is like, okay, what is durable? What do we build in a self-reinforcing way?

There's kind of two interesting types of data that we learn and that we collect. The first is candidate intent and interest data... we track tens of thousands of interested candidate responses at any given point in time.

The second part is the company internal data... It becomes more like hiring someone internally than it does buying another SaaS product."

- @davepaffenholz

[Knuckle Up with Nakul @KnuckleUpHQ]

AI does 90% of Glean's prospecting work. Glean still doesn't use an AI SDR. Arvind Jain on why:

"I think first of all, AI lacks judgment. From an SDR perspective, we use AI heavily, so it is doing 90% of the work for us in the prospecting workflow...

We do have SDRs... their eyes have been on it and they've tweaked it to the best of their satisfaction. And that actually creates much better results because otherwise, people like my high school kids, they can tell you very quickly what text is written by AI and which one is not. And so customers also can tell.

We are very firmly of the belief that AI should be used as a tool, not something that replaces the entire human task. It can replace 90% of that task."

- @jainarvind

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James Cadwallader on a big hiring red flag at Profound: generalists.

"A big red flag for me when hiring is when people are kind of generalists and they're like, 'Hey, I want to do a bit of this, but also a bit of this. I'll start here, but maybe go here.'

What we're really looking for is like, 'Cool, if you're a front end engineer, you want to be the best in the world.' And you are learning from the greats, you are researching, you're doing your homework and you are obsessed with the idea of total mastery of craft.

And that's not just an engineering thing. You could say the same thing for sales, for customer success, for design."

- @thejamescad

[Knuckle Up with Nakul @KnuckleUpHQ]

How Garrett Lord pitched Handshake's board on starting a new business from zero, and what one board member said good would look like:

"I laid out a whole investment thesis, because so much of getting the budget to approve this was telling a story around what this could become...

I started off saying I wanted to spend five or $6 million on this new business venture. And I said that by the end of the year, we wanted to be able to target 25 or $50 million of run rate revenue. And that seemed insane.

I remember asking Will Reed, 'What do you think good looks like in a year?' And he's like, 'I think it's probably 100 million bucks.' And I'm like, 'Dude, you're absolutely crazy.' I mean, we're starting from zero. We have one lab relationship."

- @GarrettLord

[Knuckle Up with Nakul @KnuckleUpHQ]

Every month at Applied Intuition, each engineer and their manager grade the engineer's output and behavior red, yellow or green, blind. Qasar Younis on why:

"Every IC will get a red, yellow, green on a monthly basis... We do red, yellow, green on output and red, yellow, green on behavior, which is roughly values adherence.

It's very, very quick and both people do it. You're my manager, I'm the engineer. You're gonna do red, yellow, green on my output and red, yellow, green on my behavior.

Let's say I wasn't that good this month. It's yellow, but my behavior was a green, and you actually think the opposite. So it's double blind. So when that's shown, that's immediately gonna trigger a conversation.

What you're doing is you're doing a little bit of feedback pretty consistently, rather than some big performance metric.

I continue to believe the most important person in a company is the first line engineering manager. That is the company."

- @qasar

[Knuckle Up with Nakul @KnuckleUpHQ]

Juicebox is at 90 people and hasn't lost an employee in the last two years. David Paffenholz on the three preconditions for doing your life's work somewhere:

"One of those preconditions is you need to have independence... You can actually make decisions yourself.

Second, it has to come with some form of reward. You have to feel that the impact that you're making is seen, be that impact on the customer, be that the commission payment that you can earn, be that the career development you can have.

And then the third thing is, the company is growing fast. We try to make sure everyone has a sizable equity stake in the business so that they also have strong financial upside to be at the business."

- @davepaffenholz

[Knuckle Up with Nakul @KnuckleUpHQ]

Glean's coding interview used to be a program you could write yourself in two hours. Now it's a task you can't finish in two hours without AI.

"We used to have this programming exercise before. It was a 2-hour session and there was a program that we thought could be done if you write code yourself in 2 hours.

Now we don't actually tell people and prompt them that you can use AI to do it, but we give them a task, which is so, so much more in complexity that there's no way for you to finish that in time in 2 hours, unless if you use AI.

We've done that across departments. AI fluency is a key check."

- @jainarvind

[Knuckle Up with Nakul @KnuckleUpHQ]

Exa CEO Will Bryk on why 2am is when he does his best thinking:

"I come into the office around 9:30, and the second I come in, it's just chaos. There's so many things going on. There's so many problems. There's so many amazing things. Slack is going crazy.

Then I'll go home at maybe midnight or something... and then my brain starts to synthesize everything that happened. And then it's like, oh wait, this is the most important.

And then I'll send a bunch of messages at 2:00 AM to people, 'Okay, we got to do this, we got to do that. We got to change that.' And then I'll fall asleep... and then I do it over and over again. But that's kind of the day, which I just love."

- @WilliamBryk

[Knuckle Up with Nakul @KnuckleUpHQ]

Why Guillermo Rauch has a few vendors on the chopping block at Vercel:

"I'm literally reconfiguring all of my priors. I used to think your software is good or bad based on, I don't know, the website is fast, it has a lot of features, I can click around and it works reliably. Now that's all table stakes, of course.

I have a few vendors on the chopping block... maybe they do have an MCP, but their MCP takes, I don't know, 2,000 tool calls and it fails a lot.

A lot of software maybe did present the right API, maybe did present the right interface, and now you have a billion agents querying it at 100 requests per second."

- @rauchg

[Knuckle Up with Nakul @KnuckleUpHQ]

@bipulsinha Full conversation: https://t.co/TnCsowekbb

[Knuckle Up with Nakul @KnuckleUpHQ]

David Paffenholz's contrarian take on AI adoption inside Juicebox:

"90% of employees don't need to be AI-pilled. They need to be good consumers of AI workflows or happy to adopt them, but they're probably not going to be building the actual workflow because that would be a bad use of their time and resources.

And so we have dedicated builders, be that our go-to-market engineer, we have a product engineer that just build internal workflows.

We'd rather have one or two people who build at a really high quality for internal workflow, and then everyone else is AI-pilled in the sense that their work got easier, not necessarily that they're building something with AI."

- @davepaffenholz

[Knuckle Up with Nakul @KnuckleUpHQ]

Arvind Jain has talked to over 1,000 enterprises in the last year. The top three AI concerns he hears:

1. Who to bet on. "One day you have GPT being the best model, the other day Gemini takes it over, then Claude takes it over, and then GPT comes back."

2. Cost. "They've created these annual budgets and they've blown past that in 1 month or 2 months... business value is still elusive."

3. Sprawl. "You have a lot of AI slop... People are building skills and agents and there's a lot of duplication."

- @jainarvind

[Nakul Mandan @nakul]

Next up on @KnuckleUpHQ: @paraga!

[Knuckle Up with Nakul @KnuckleUpHQ]

Juicebox CEO David Paffenholz on a product call he got wrong:

"I thought an MCP server for a recruiting platform is kind of silly. I felt pretty strongly about that. We did a bunch of customer interviews, and it seemed like that made sense. I was wrong on that.

It made it look like we were behind. I probably set the team back by like a month.

I have to be comfortable getting those wrong, and then I also have to be comfortable telling the team, 'Hey, I got this wrong, and here's how we're going to change it.'"

- @davepaffenholz

[Knuckle Up with Nakul @KnuckleUpHQ]

How Garrett Lord decides which problems get his time at Handshake:

"I like to think about problems of red, yellow, green. What's red today but will be green in six months? I try to not focus on those problems.

A lot of the team wants to flag issues to me where there's a fire, and I'm like, red, yellow, green, is it going to be fine in a quarter? Is it going to be fine in two quarters? If it's going to be fine, if you guys have the ball, I'm not going to spend my time there.

I'm going to try to focus on things that are red today that will be red in the future."

- @GarrettLord

[Knuckle Up with Nakul @KnuckleUpHQ]

How Garrett Lord decides which problems get his time at Handshake:

"I like to think about problems of red, yellow, green. What's red today but will be green in six months? I try to not focus on those problems.

A lot of the team wants to flag issues to me where there's a fire, and I'm like, red, yellow, green, is it going to be fine in a quarter? Is it going to be fine in two quarters? If it's going to be fine, if you guys have the ball, I'm not going to spend my time there.

I'm going to try to focus on things that are red today that will be red in the future."

- @GarrettLord

[Knuckle Up with Nakul @KnuckleUpHQ]

Vercel is nearly 800 people. How Guillermo Rauch still stays close to hiring:

"I don't meet every hire, but we have agents that can be posted on the progress of all of the interview loops. We've put in a lot of my requirements into the different prompts that summarize the candidates.

We care a lot about candidate experience. Even if we don't hire you, we think of you as a customer.

I take each hire so seriously because I'm gonna invest in you, and I expect you to stick around for a decade."

- @rauchg

[Knuckle Up with Nakul @KnuckleUpHQ]

Does Exa run 996? Will Bryk's answer:

"I don't require people to work at certain times, but people do work extremely hard because they are excited by it. I make sure everyone works on whatever they're most excited by. When you do that, it doesn't even feel like work.

Having to enforce a rule like 996 is a symptom of a problem that you are not matching the things you need at the company to the right people."

- @WilliamBryk

[Knuckle Up with Nakul @KnuckleUpHQ]

A lot of Profound is in the office six days a week. You can also leave at 6pm and no one bats an eyelid.

"Culture at the extremes is very easy. I can do the rah-rah 9-9-6 thing. There's the warm, fuzzy, we're all a happy family thing. The difficult thing about building culture is to capture nuance."

- @thejamescad

[Knuckle Up with Nakul @KnuckleUpHQ]

Frank Slootman on the most common growth mistake in a good company:

"99% of all people don't lean in hard enough. They are on their heels. Skis are designed to be over, not on your heels.

If you have a good company and a good product, odds are that not leaning in hard enough is a huge mistake. This is how you create separation from your competition."