Nov. 17, 2022

#65 - How to Quit Your Job

If you’re a founder or creator, chances are you start out doing something on the side. But as things start to scale, you will need to give serious thought to going all in.  

In this quick episode, Brendan and Bob talk about how to make that transition. Because you don’t want to burn any bridges, you do want good references, and you might even be able to turn your existing employer into a customer…

If you’re a founder or creator, chances are you start out doing something on the side. But as things start to scale, you will need to give serious thought to going all in.  

In this quick episode, Brendan and Bob talk about how to make that transition. Because you don’t want to burn any bridges, you do want good references, and you might even be able to turn your existing employer into a customer…

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Hey, Bob, guess what? 

It's another edition of Let's Chat Sales. 

No! Let's Chat Sales! 

Yes it is. 

We're gonna talk about how to quit your job and as you move into your own thing, when you go off on your own, how to go about doing it? 

So this would be that scenario where you've been working at your full-time job probably during the day

and you've been building a business, 

your solution to the world problem at night and on weekends and on your days off.

And now suddenly you've maybe gotten a couple customers 
or you're just ready to make that jump. 

Yeah. Right. 

And how do you do it? 

How do you go about doing it? 

And the key being how to do it without causing problems? 


You don't wanna burn a bridge. 

So the first thing is legally can you do it?


Let's just start right there. 

Cause you might 

have a noncompete or a nondisclosure agreement also, 

Or whatever value that you create in your spare time belongs to somebody else, right?

And so that's beyond the purview of this conversation. 

I mean, if you got some sort of legal document or 

you're somehow constrained from working on something outside of this. 

Outside of your job then you gotta go talk to someone who really knows that 

and you gotta have them examine whatever the document or documents are that are constraining


Cause that's not in our, 

And you say if you think this might be an issue worth your time to go talk to a lawyer before you

leave your job. 

Yeah. Yeah. 

That's how you 

Yeah, figure that out. 

Figure that out. 

ROI on that. Huge. 


So, Right. 

So then, that's one. 

The other is, have you been doing it in such a way 

that it's ethically to the benefit of yourself and is not harming your employer, right?

Are you doing things harm employer? 

So you're not gonna steal all their customers? 

You're not stealing your customers, you're not taking their intellectual property,

you're not working for your business on their time and getting paid.

I mean, that's just let's be human about this. 

Let's be upstanding citizens. 

If you're cranking away, 

We'll believe in karma. Bad karma's coming at you if you do this. 

I totally believe in karma, right? 

So karma is, karma is key. 

That's another one, right? 

So you got those outta the way, and now it's, how do you go about doing it?

Like, what's the right way to tackle that?

You wanna take a stab at it? 

I have a lot of experience. 

Let's, I've got some ideas.

I mean, one is, I think having an honest discussion with your employer.


About the situation. 

I've found and I've left in my career, I've left 15, 16 jobs. 


I've always done it with the utmost respect and concern and always the thought in the back of my


I might actually have to work with this person or company again.


And in one case, the person who was my boss became my boss, unbeknownst to me at a second



And several other times, people that I worked with in my career have been at jobs where I've


So especially in a town like Baltimore, if you're in the Baltimore area like you and I are. 

Everyone knows everyone.

It's a small world.

And you're in an industry that's very small. 

Everyone knows everyone in that industry, all over the place. 

There's no such thing as a big industry at this point because of the internet and so forth, 

but like I work in, a large part of my work is in healthcare and in health technology.

And that is arguably the biggest industry in this country and one of the biggest industries in the


One of the reasons it tends to be small because everyone tends to niche down.

So even though I'm in a particular part of healthcare.

I'm in a part where you connect the interface between physicians 

and patients and health plans and customers, members that side. 

So I don't get involved in backend billing anymore or EMRs and that sort of stuff. 

So that niches you down right away.


So it's a small world, so not to belabor the point, you're gonna run into people again.


So to do, in the most. 


So let's do it the right way. 

Let's be upstanding. 

Yeah, be upstanding. 

So having that discussion with your employer, not as you're thinking about it.


But when you're really like close to it or actually gonna do it. 

I've, in several cases, I've actually said to my employer, Hey, I'm getting ready to leave.

I've talked to some, I've got some things coming, and I just wanted 

to give you a heads up because I know it takes a while to replace someone. 

And I might be giving you my two weeks notice in the next couple weeks. 

So you might wanna start seeing what, you know, get the ad ready and those things.

So when you do that, there are a bunch of things that could happen.

One of which is, and this is one you have to be prepared for. 


One of them is, 



If you're leaving, don't let the door hit you on the way out.

We're ready. 

We're ready to see. 

Right, Right. 

You'll have to ascertain whether or not your company is like that.

Some companies, they want you out there that day.

Other companies, they're very tolerated, but it depends 

on the relationship you have with them, that sort of thing. 

The other is also might matter whether they think you could take their customer. 


Well, that's certainly gonna, 

If you're doing something that's very similar to what they're doing, 

they may cut you off right away so that now you've told 'em, 

Hey, I'm going out to be your competitor.


And if you're going out to compete with them, that's a whole other kettle of fish. 

And then, you have to wrestle with that. 

How are you gonna tackle that?

Then you know you're not gonna be received very well. 

From them if they're, if they view you as a potential competitor 


but, alright. 

So that's maybe in some cases the worst case scenario. 

 But, another 

worst case scenario as you leave them and they actually hire you. 

Well, that's where I was going.


Right, right. 


I was gonna say that they could hire you. 

They could come back at you and say, Oh no, we only want you to leave.

We're gonna pay you more money.

Think and why don't you keep developing your thing on the side, but we'd like to keep you

because you're invaluable to us. 

That's one, another is they become your customer. 

Or they hire you part-time afterwards as a consultant, part-time for the transition, 

or maybe they decide, Hey, listen, we still want you, but we're gonna spend less on you.

And this way if we get you as a consultant, maybe we can ratchet back how much our investment is

or what have you. 

So that's another 

I have a friend who work for a company,

and he told them what he was gonna go off and do, and they we're really interested in that area,

we've been talking about that area.

They started talking about it and they actually bought his solution. 


That's And made head of that solution in their company. 


 Oh yeah. 

You know, crazier things have happened. 


That could definitely be the sort of thing that could be the outcome, right?



So anyway, 

There's multiple options. 

Yeah, yeah, exactly.

But the key behind all of them and all those possibilities is being honorable and doing it as effectively as you can. 

Because if you start burning bridges or badmouthing your company or going out and selling what

you're doing,while you're still working for the company on their time, it tends to get back to them.

Yeah, that's kinda schmucky. 

Yeah, that's like, I wouldn't recommend that. 

And this goes back to the fact that it's a small world 

and I'm running into this right now in a certain circumstance where we've got an ex-employee

And they're, they're gonna kind of undermine the enterprise 

and also ruined their reputation, which could be damaging to you in the long run.


So, yeah. 

Well, the reason I started this company is because 

I didn't like the way my company was doing it. 


So I wanted to prove them wrong. 


That tends to not make for good playground activities later in the day.


I think that's it. 

I think we killed this one, don't you? 

I think we covered it pretty well, but I think the one thing I would say is do it honorably.



Talk to you. 

Let's do it again.

That was another episode of Let's Chat Sales a quick one, of course. 

And I hope it was helpful. 

And if it was please like, and subscribe and more importantly, share it with your friends.

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It should be good.It's probably good. 

Certainly short.

It's probably helpful. And thanks for listening or watching.