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Jay’s unorthodox approach to hiring

Episode 15: Rupy seeks Jay’s hiring expertise before taking on his first round of interviews for a new CTPO (Chief Technology and Product Officer) position with Doctor’s Kitchen. Jay breaks down the different phases of a startup company and what Rupy needs to do to attract a key player to the Doctor’s Kitchen family. How will Rupy position himself to attract the right fit for his company?

What to look forward to:

00:30 – Rupy looks for a new addition to the Doctor’s Kitchen team

02:17 – What should Rupy look for in a potential business partner?

03:15 – The different phases of a company

06:39 – Questions to ask potential new hires

12:18 – Interviewing Etiquette

13:22 – Interviewing Red Flags

14:19 – How to successfully haul in a whale during the interviewing process

15:13 – How Rupy can look attractive to potential hirees

16:29 – How to get rich 

17:05 – Jay’s message to viewers to find their niche as an entrepreneur

Previous guests include: 

Reece Chowdhry & Poppy Jamie



HM Ep. 15


I catch a whale, right? Yeah. And it's time to haul it in. What are the things that I need to do to haul in this whale? I've only got a small fishing boat here. Yeah. Yeah. It's not fit for a whale. Yeah. Yeah. But I want to, I want to catch a whale. What will think, how, how do I get that


on board?

Um, welcome to Happy Millionaire, A show about how to make a profit with a positive impact and stay happy along


So long story short, I put together a job description, and this job description isn't like your average job description that you'd find on like workable or a typical job board. Mine was very different. Mine's like, yo, I've started a, a brand. Five years ago, this is the traction we've got and this is the kind of person, uh, I'm looking for.

love this and you understand [:[:[:

This is


But also I want to give the impression to this person that, you know, it's essentially a co-founder. We're gonna have a ton of fun and they're gonna be responsible for building a tech team, but also being a critical part of the culture that I wanna create at the doctor's kitchen. Right. Like a real, fun, loving atmosphere with a very serious mission at the helm of it.

Like, I'm not gonna let you [:[:



What would you these with these

[:that, to me, that's not good [:

I'd say that's probably number one. Then, uh, I'd say number two for me then would be, because you're so early, right? And there are people just for the listener like there are so many different stages of a company, right? You've got like the incubation phase, then you've got like an early stage where you have a product.

You wanna know the push to customers? I guess phase three would be now you've got some customers, then you've got the product. Then after that it would be, you know, you've now got probably some money behind you and you've got, the business is starting to accelerate. You've got a good number of customers and then offset some moments.

a good number of users, like:eople constantly use, right? [:

This is how you operate. Like you have to keep on moving. So number two to me will be like, have they had that true early stage experience where they, you know, the ship keeps on moving left and right and they keep on falling essentially on the ship? They might be capsizing and coming back in, right? But do you know what I mean?

They have to have that experience. If not, like, it's so difficult, to teach that one. So in my mind that that is super, super key. So you know what questions you can ask there. Tell me a project which you've built from scratch, like recently, because you don't wanna send your last job. You wanna just hear it out from them because the one they're gonna say is the one that means a lot to them.

s gonna slog it. So you need [:

Family and their personal priorities and you know, had you asked that that's a more tricky one. I feel you got to ask them like, how important is the success of this app? And you've gotta look 'em right in the eyes. Cause it's a problem. A lot of people, and you know, I've seen this in my companies, they, they will give a big, big answer.

But deep down, They've got other priorities, and that's fine depending on the phase of the business. Right? If it goes a bit late, you know, as you grow, that's fine. But in this early phase, you need someone who's gonna be, you know, walking with you, like with your, with, you know, holding hands. You are bloody hard, right?

So I'd say, um, that's really important. And I've been, I've given three. I'm gonna pause Any questions before I...

[:they been in this phase yet? [:

And that sort of question to sort of dig into that is, Telling me about a project that they've built from scratch recently, and the fourth, see on


So, you know, sometimes corporate, they get like, like a big wanky like office and $10 million to build a team. So it's like it's not real. Yeah. Yeah. Were. Were you also involved in like incorporating the company? Were you involved in you doing all the legal work and the setup and the operations? Cause a lot of these people are in corporate, they're literally given a throne.

o for a couple more and I've [:

Yeah. They just architecture, They get it. They know how to build a good product, right? However, you ask them, Hey, do you know how, how this is gonna sell in the market? Like, how do you, how do, how are we gonna get this product in the hands of people? I either go to market the commercial piece, right? They're, they're not very good because they're just so focused on their lane.

You need someone who's, you know, put their head up and understands how to also sell this product. A little bit because they should be familiar with who that customer is as well and tell you, Hey, like, yeah. So I would ask them, how do you think we should be promoting this app? And like, who do you think our ideal customer is?

Like they're not gonna exactly know, but they should have a bit of a feeling they should go to have a conversation about the commercial piece. But I'd say that's very, very important. So just ask 'em some commercial-led questions, like, you know, how are we gonna promote it? And who's our ideal customer? Those are very two easy questions to ask.

The other [:

Because a lot of people will go, Hey, yeah, you know, I had a team of like three people, five people, 20, 30, 70, whatever. But they inherited a lot of that, so they didn't hire it. Right? Right. So just say like, how many people have you personally hired? So that's the question. And how many of those people

if you got this job would join in a heartbeat? Right. That's a, I like asking that question to just see if they can bring people with them. You are playing poker a little bit in the interview, right? Mm, you are. So you just have to like try and position it so, um, you can read the hand better.

umber and a lot of them have [:

But you know, I'd also, Same questions to each person. I take notes in the interview as well. Yeah, because trust me, you're not gonna remember. The most important piece in all this, like you, can do the best interview, but honestly, the most, most important thing will be the references, right? Yeah. By far. I feel that is where you're gonna get the most information.

Like if you are interviewing someone, you know it's gonna be someone that is gonna be a colleague, right? And just making sure you do the references right, Um, like re-referred people always gonna be better because especially for someone you trust, because they probably work


How do you define the ideal customer and then, and then target them as well? Yeah. Especially the early adopters and then the hiring pieces. That's such a good question. I probably wouldn't have asked that. Like, how many people have you personally hired?

[:So, this is, this is really [:

Then there's another 30% which are like, okay, they're good enough. They're okay. So you have with another 40% and out of that like, you know, 10 50 percent's like, Oh, this is good. Thumbs up. Yeah, I'll work with them. But they're good. Right? Wow. And then there's like another chunk, which is like probably the last 30%, which is like, or 20%.

They're like, Wow, these are. These are rock stars. I, I would work with them every single day of my life again. Right. So if someone is telling you that 70% is very unlikely, I,


Yeah, that's, Yeah. Very good question. Because Fi, finding someone who. Hires relentlessly, but doesn't have the cognitive bandwidth or the bravery to fire. Yeah. It's probably


Okay, great. And how many, of those 20 did you fire? Right? Just do it straight away. Yeah. Then they like, if they're the right people for the job and it's meant to be, it'll work out. Yeah, yeah. For


I wanna know that they can carry themselves and, at least speak articulately about their area of the business in front of people who are gonna potentially throw money at it.


Right. I would therefore ask them to, A problem of yours, Maybe one or two. Okay. Right. And you know, you get them to present, and then, therefore, you can see how good they are at

[:[:. Your next one should be a, [:

And then it's a presenting round. Some tests are good just in case like personality tests and things like that, person tests or, um, actually a technical test. Are there things that are like sort of gray areas? Like one of the things that we do in Screenloop is give them an opportunity to ask questions at the end is just etiquette.

Like they've given you their time, you gotta give your time talk speed. So you know, English, is not their first language. Um, it's very important that we talk at a good pace. Um, that's again, another. It's a really good point. A big problem we've seen in interviews when


So how do you find these other references? Do I literally go to that old company's HR and just be like, I'm thinking about hiring this person who can give a reference or like, how do I


and like in your case it's, you know, you're hiring someone who's a c TPO O Okay. So you might wanna look at the other exact members, right? And hopefully, there are some mutual connections you've got, but you know, our pure respect tells the candidate you're gonna intend to, um, speak to people. So it does not catch them off guard in terms of, um, red flags.

Yeah, I'd say. Answering my question, I'm telling you right now, so people don't answer the question. That's maybe cuz they're not present or they don't wanna answer that question. They wanna go, Hey, I ain't got that one prepared. Your number two is just the. Yeah, you just know when you're speaking to someone, it just feels natural and it feels good if you hang to make a lot of effort, right?

This is the first date, right? It's not gonna work out. So thirdly how in line are they with what you're trying to do here? Because they're gonna have to go through so many walls. Fourth is I, you know, I like to know if they've got some good questions planned. Cause then they've done their research.

That means they do [:[:

Yeah. Yeah. It's not fit for a whale. Yeah. Yeah. But I want to, I wanna catch a whale. What will thing, How, how do I get that person


Because that's the formula, Like whatever's grabbed them, you need to work out, you have to decode it. Then I would say like, really get your, um, investors and your advisors to help. It's not, it's not just gonna be you here. Like you need the support of all of us. Do you know what, like you have to, unfortunately, and this is where it comes to that woo there, but it's like, if it's meant to be, it's meant to be, right?

, it feels a bit forced, so, [:[:

Uh, if you are a CTO, CPO, CTPO, whatever, and you are coming into a company, what things do you want me to demonstrate to convince you that, you know what, I'm, I'm super excited about this company and this guy's got my back, and we are gonna make this


Right. And you are, you're an example. Ideally, you know, we raise some money before we buy this person, so I feel they need to believe that you can raise the money. I think you need to just say, Look, you and I are. Again, hold hands and we're gonna go raise some money as soon as you join.

want one month or two months [:[:

It's like you're gonna come on board. Yeah. We're gonna break this product roadmap together. I've pretty much done 67% of it. Yeah. With the ideal person on board, we are gonna like an attractive power couple to people who wanna throw money at it so we can grow this thing. There might be that phase of life that you mentioned earlier, that they're willing to, you know, Yeah.

Try this out


Building a tech company. And if you are thinking about starting something, I know you probably look at Ru, say Ru's got a big audience already, and um, you know, it's gonna be easier for him and he's got me. Okay, That's fair. But I think if you find your specific niche, which you do have more knowledge than others, which I believe everyone will have something, even if it's wacky and crazy, there will be something and you know, your main objective will be trying to monetize it.

Right? So Ruby's monetizing all his knowledge through an app. He's already done it through a podcast, done it through a book, but he's realized that um, to win big, he has to do it, to do the app. And what does win big mean is, or touch more people and Yeah, from a money perspective as well, So. Reinvest it, um, to then help others.

everyone needs to go on that [:

Um, and you can feel it in your heart, like when I'm speaking right now, then I believe there is something there for you.

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