Bob Moesta and Paulina Masson: JTBD and Selling Your Company

In this session, Bob Moesta and Paulina Masson discuss how the four forces of Jobs to be Done (JTBD) come into play when Paulina sold her business, Shopkeeper.

They discuss:

  1. Paulina’s thought process as she moved from running the company to selling the company;
  2. On the buy side, how an acquirer will assess the opportunity and the value of having a supportive and knowledgable broker between the two parties.

You will understand how the four forces come into play for you and a potential acquirer as you approach and prepare for a sale so you can be better prepared to achieve an ideal outcome for yourself.

First a reminder of the four forces and how they might apply to an entrepreneur who is considering selling their company.

The Four Forces that come into play when someone considers switching product.
The Four Forces that come into play when someone considers switching product.
The Four Forces for an entrepreneur considering selling their company.
The Four Forces for an entrepreneur considering selling their company.

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Transcript

Bob Moesta
So, I’m just gonna interview Paulina about selling her business. And I have a bit of notepad, you can see that oh, you can’t see that. How do I do? Hold on, I gotta fix that. Stop flirting my background. It’s this. I’m just gonna start with a blank sheet and just have a conversation to understand the kind of what were the forces? And what was the thinking? What are the variables that caused her to say today, today with today? This is the day I want to be able to sell my business. And what I would say is if you have questions, or you want to push pause, I have a phrase where I talk about game on game off. And Mark, like, if questions come up, and people want to ask, like, Why did I ask that question or where I went? I think it’s as you feel free to kind of go game off mark, and then I’ll say, then we’ll go being back on okay. Paulina,

Paulina Masson
Hey everyone. Nice to see you. Nice to meet you. Nice to be here.

Bob Moesta
And just so we’re clear,we have never met before. So I have not met Paulina at all. This is Mark doing his matchmaking at his best. So, Paulina, can you just do a little introduction about who you are, and you know what business you sold? And just give us a little bit of your background? And then we will we dive into the interview?

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Paulina Masson
Yeah, so thanks, everyone for choosing this breakout, Mark also

Mark Littlewood
was keen for this.

Paulina Masson
So my name is Paulina, I wear a tag of serial entrepreneur these days. And I’d say that I build and sell businesses. Since the previous one, which was a successful one, I decided this is the label I want to wear.

So my background is in software development. I went to university in Canada, in Ottawa, and I’m originally from Lithuania. And right now I live in Turkey. Living the digital nomadic life.

Bob Moesta
So awesome. Yeah.

Paulina Masson
So yeah, so that’s a little bit of insight into who I am.

Bob Moesta
Got it. So you’ve done multiple, so let’s just talk about the last company that you sold, and and we’ll kind of walk through the process of how we kind of uncover this, right? So what What business did you recently sell?

Paulina Masson
So in entrepreneurship, I’ve been 11 years. And this one, I sold that the last summer, so it’s been

Bob Moesta
Summer of 2021. Right?

Paulina Masson
Was it? And when?

Bob Moesta
And when did you? When did you start it? Start this one? So it

Paulina Masson
Was three years before that?

Bob Moesta
At some point the summer of 2018. Right?

Paulina Masson
Exactly. So in essence, every business that I ran, it was about one to three years. Yep.

Bob Moesta
Yep. I’ve done seven

Paulina Masson
Yeah. So.

Bob Moesta
So what was the business? What did it do?

Paulina Masson
So the business was called shopkeeper. If you want, I can share my screen, just like while I’m talking is very nice. Is that okay with you? So the business was called shopkeeper.com. So it was a software for Amazon sellers. It’s the dashboard that tracks their sales. So that’s what it was. And the pricing model was like monthly dynamic pricing model. And so just to jump ahead and let you know, like, I have another business right now, which I started, which is a similar one. So again, it’s targeting solopreneurs this time YouTubers and the pricing model. Again, it’s a similar thing. So I’m like building on the knowledge that I have from the previous one.

Bob Moesta
When did you when did you did you start this one before? By the way, did you start this next one before you sold the shopkeeper?

Paulina Masson
No, so I didn’t know exactly what I’m gonna do next. I just knew that my plan is to build and sell. I couldn’t handle a one product for more than three years. I learned that is just like I am that type of person. I think all entrepreneurs are like that. If you are an entrepreneur, you know what I mean? Like you have one shiny object, then you get it. You’re excited to the 100% and then you work, work, work work and their time comes like all the challenge is done the hump of learning curve is done. And what’s left is daily zoom calls and “did you do this? Okay, you’re gonna do this” and that is not fun anymore! So that’s the time to sell

Bob Moesta
So perfect. So when did you have the first notion that was like, Okay, we’re getting close here, like, what was what was like, at some point when did like, because you always use you build it with the notion of selling it. But when did the trigger start that? Or when did you start to realise? Like, you now I think it’s gonna start to be time, like, when did you actually start to have those early thoughts?

Paulina Masson
So in reality, this one I’ve built with that in mind. So I had a plan that I want an exit, seven figure exit in three years. And the way I did this, I reverse engineered what it was gonna take. So I made the plan like that. So I reverse engineer, meaning I took a price tag of seven figures, and then I also okay, what’s gonna be the selling multiple, probably about 4.5, because that’s what my type of companies go for that little bit of googling / little bit of talking to potential brokers who are gonna sell my comapny.

Then that 4.5 Turns out into the monthly revenue that I need to have minus the expenses, that turns out into the profit that I need to make every month, divided that by number of customers. And now I know how many new trials I need to get every day now where I’m gonna get them. Okay, if I need 30 new trials, that means I need to have at least 30 SEO articles. And one SEO article takes a week to make so I’m gonna work 30 weeks one SEO article a week to sell for 1 million. So it’s like, I reverse engineer that pylon number that I wanted. I just wanted seven figures because it made sense, I’m gonna pay off my house, I’m gonna buy this buy that, you know, it just made sense in my life at that time. And once you have that number that really like makes you happy, you know that this is not going to be your final product. Like nobody has a final product in their life, you know, ever. Yes, we are entrepreneurs, we are gonna do something else. But what will make you just like, solve all your revenue problems, you know, revenue solves all problems, what’s gonna solve and make you just enjoy what you do? You know? So that was my number.

Bob Moesta
When you started this though, you had that number in mind, and you use that number to guide you to kind of the actions and the things you needed to do. But at some point in time as it’s as it’s growing, are you getting excited? Are you getting excited for it growing or you’re getting excited to get out?

Paulina Masson
So in software, in my experience in the first year, you don’t really make any money. It took us 18 months to get the break even point. So we were building it for about six to eight months, then we launched now one came, made a lot of mistakes and so on, we were flat with 20 customers for another eight months. So it was really really hard to get the the wheels going, you know, in the beginning, I don’t know. Like I was just smashing spaghetti is everywhere, you know, and trying to see what works. Googling things like okay, marketing methods for SaaS companies, what can I do? And then I tried like 27 different things. Okay, let’s launch on ProductHunt oh, let’s do like helpmyreporter.com Whatever, you know, and then, okay, Reddit ads, ah, that’s gonna work. Like all crazy things that just really not worth your time. Now, I know, they’re not worth my time. But that time I didn’t. I didn’t know it’s not gonna work.

Bob Moesta
I’m just gonna go game off for one second. This is this is the exact thing I kept talking about is prototyping to learn. When you’re an entrepreneur, people from the outside, look at it and say, You’re failing all the time. But if you listen to her voice, and what she’s doing, she’s learning all the time. And she knows she doesn’t know and I have to go figure it out. And this is a really important point as you go to build to realise like, even though you build a plan, it doesn’t actually it never falls together as a plan. But it’s about building thresholds of where you can say like, Am I making progress? Are we doing the right things and having the right metrics to guide you along the way, but at the same time, you don’t know what you’re gonna do next month or next quarter or after that, and you have to put some some predictions together but it’s more about basically this notion of just figuring it out. And you can tell she loves the fact of figuring that out. Right?

Paulina Masson
Every entrepreneur likes is undefined space. That’s why we love it right? Because other people are uncomfortable not being safe out of the job we are comfortable we want this so we’re

Bob Moesta
We’re comfortable with being uncomfortable.

Paulina Masson
Right exactly we wanted to find something sensible

Bob Moesta
Help me understand when when did you start to have enough traction to know that it was getting to be time?

Paulina Masson
Right so at that point, while we were still getting to breakeven, that seven figures seem so far away, you know, I didn’t know if it’s gonna happen for me or not. But I already started seeing some traction in the company. So at the break even point And, you know, we were already making, I think it was just like $6,000 MRR, you know, for us, that was enough to cover the development costs, you know, that was the breakeven, right? So it was not that much of money. But it was enough for me to know that it’s gonna work. You know, I had customers, I have the systems. And at that point, some point like a few months after that, I already talked to my broker. I told him, I want to sell for seven figures. What’s that number every month? That has to be that I have to reach? And he said, Okay, so you have to reach, you know, such a number of MRR a month. And that’s where you going then call me, you know, when you get there? Yep. So now I know, you know, from 6000, I need to go to double digits, you know, and I’m like, okay, so we are going to work on that. That’s how I went through this.

Bob Moesta
And so and so at some point in time, when when was that, that you broke, even if you sold this in the summer of 2021, when was the breakeven time I

Paulina Masson
don’t remember the date. I remember that it was exactly 18 months after starting the project. So like

Bob Moesta
December of 2020

Paulina Masson
A year after launch.

Bob Moesta
December of 20. So it’s almost like when, when COVID hit just one COVID hit somewhere around that.

Paulina Masson
Yeah, no, wait, no, that’s another year before that. COVID was not in a launch. That’s another year.

Bob Moesta

So 2019.

Paulina Masson
That’s why I raised my eyebrows. Did I sell last summer of the summer before.

Bob Moesta
But the one of the things is the trigger this so here’s the thing is the trigger to get you to start to think about selling was the moment you said I can I like the thing that you were does it work? And the notion is can I get it to break even it’s like, okay, I got to break even. I know I can scale it. But the reality is, there’s a lot to do. And so the past, the first thought really comes when you get to break even, and you call your broker not to sell it, but to say like, what are the numbers I gotta hit to basically be able to sell this thing. So now you have the true numbers as it relates to the market right now. Right? And

Paulina Masson
then seems so you had gold versus, like, it seems like a structure that I had, but in reality, when you’re in it, you just swimming wasn’t the structure, it was just this one thing that I had in my mind the number and I knew I need to get there. And it’s like every month, okay. Last month, we got five new customers. So that brought us extra $1,000 a month, you know, what can I do to get extra five? Okay, here’s the things I’m gonna try and not, you know, another month I tried something else. This worked better. Now, let me do more of that. The next one. So is this like, every time building on the knowledge that I’m gaining while I go? Eventually, out of these 25 marketing methods, I found the three what works the best. And I just stick to these three. So like in the last year, we just did SEO affiliate partnerships. And that’s it like, and there was a combination of other things. But we discovered the things that work and stick to those. And I dropped all the Reddit ads and other stuff that didn’t work. Yeah. And that really helped. You know,

Bob Moesta
when did you when did you actually start to engage the broker? What was the moment where you started to say, like, Okay, I’ve got these metrics. He’s the right thing. How far before summer of 21? Did you actually start to go like, Alright, I’ve got this, we got to start shopping.

Paulina Masson
So look, I had about 10,000 I think MRR that’s already one I called him. Because when you go to a broker, he will tell you that small websites and businesses sell on Flippa I sell minimum $600,000 type of exits, you know, so it’s like, minimum six figure exit he’s gonna take on as a customer. Well, I want to seven figures. So he he he told me how much I need to have on my calculator, okay, if I’m gonna get 30 new customers paying customers every month, and because they’re paying me up to $200 a month, you know, I’m gonna get there and that time, so I calculated the number of customers I need to have in order to get there in one year from then. So basically, when I contacted the broker in about 15 months from that I already sold. So like we kept in touch with the broker as I grew.

Bob Moesta
And when were you were you? Were you ready to get rid of it? Like it the point where you were you there but let’s so it sounds like okay, I’m building a building and I’m building it. And was this getting to the point where you wanted to go like, Alright, I’m done. Like, let me get it. So I’m done with it because I have other things or was this more about I’m done with it because I don’t like the work I’m doing.

Paulina Masson
So usually when you’re selling there’s always two options. You can either stay on with the company, which many buyers wants you to do. And some of the buyers that approached me, one of the big Amazon software companies they actually wanted to buy a then close down so people have to keep Me, for the price that I wanted that’s not cool. But I’m saying you have choice, you always have to either stay on with the company for a while, like if you are tested, you know, and you want to help on you want your customer or you want can completely be out. So the offers that I had, I had about five offers. And like two of them wanted me to stay on one one to six months and another wanted to stay three years. And that was not what I was looking for. I just wanted to be out of it.

Bob Moesta
Why did you want to be out of it?

Paulina Masson
When you’re building, small company is like a burning crashing ship that you’re trying to sell to the shore, you know, is burning, and you’re sailing it like, for example, we had 500 new customers come in so fast. And my database is from scaling issues is crashing. And I have no idea what to do. I’m basic developer and my developers knew we were just surviving it like Oh, my God is crashing, and people need performance. One big seller came and the whole thing is slow by 12 seconds. Now we are going to google how to do the scaling, you know, big data, how to work with that. And then other kinds of issues like support in different languages. And like, it was not, okay, somebody good, who was good at corporate stuff needs to come in and like figure things out. So I didn’t have big systems in place code was written like, developer says, Can we do it faster, or slower and proper, I said faster, faster. So every time was faster features out. And that gave a lot of development depth, you know, because you’re building to just make happy the customer, but actually, to have good strong software, you know, scalable, it’s completely different kinds of jobs. So, because, you know, so I knew I wanted out, I just so stressed stress, I want that stress out of my life.

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Bob Moesta
So part of this is as as you’re proving it’s working, there’s the scaling problems that come up, there’s the you know, the support, lag, there’s all these problems that kind of come up to scale. And it’s like, what you what you say what I like to do is get to figure how to get to work. But as we start to scale it the fact that we’re going to run into these problems, and I want to sell it before it’s almost like that it falls apart because of the scaling issues. Because at some point, it’s worth something but other people who buy it will have the infrastructure to do and solve all those problems. And I don’t really want to be part of that

Paulina Masson
Yeah it’s not only it’s not only that really comes to the personality of your, you know, are you the type of person to run a big, stressful type of business? Do you want to run big Uber type type of business, or you want the lifestyle business where you will work. So I had a choice, I could’ve hire someone, to do general to be a general manager and run that stress for me, you know, to put myself out, but I’m not enjoying the management side of things. I’m enjoying building, you know, so I knew already I want out because there’s not much to build after you already built out the core features, you just scaling it.

So it’s more about like adding small feature one a month. You can even add features quickly if you want because you’re so big now, you know, one feature affects cascades into all the other features of your software and like, introduces new bugs, and oh my god, it’s not easy. And I had this 400 features that I wanted to make. And we were making 10 a year, you know, I was, it was completely not what I expected. So I know my personality, I wanted to take a blank page and build from scratch. And I’m gonna do it again. And again. That’s what I enjoy the most. That’s why maybe venture capitalists when they acquire companies, they let go the original founder, because it’s just a different type of personality that needs to run a bigger business. So I’m that little beginner guy who likes to start from scratch.

Bob Moesta
Yep. And so I think that the the lesson here that was that that builders are different than scalers, as I call it. People who create something from nothing, always want to tweak and push. And they love the intensity of that part that almost the birthing process of it. But the point is, is when it gets to a certain point, you want to keep tweaking it. But at the same time, the problem started to become almost mundane or things that are like not, they’re important to scale, but they’re not important about creation. And so you can actually find other people to do those kinds of things. And so it’s like, you will make more money by creating something from nothing to a million versus building something that’s you know, something from nothing to 100 million, because I can iterate myself more and more and the the work is way more fun and the early parts than the the other part. Is that right?

And so part of this is that as as you built it with the intent to sell it, but the fact is, is it’s this notion of that as you got to break even and as you as you start to hit the limits of the scaling and some of the other pieces, it’s like okay, it’s time because those problems are not going to go away without some major major work but at the same time the fact is, is other people will actually have solutions for that. And if I solve it, I’m not gonna, it’s gonna be work I don’t want to do and it’s at the same time. It’s, it’s it’s work that other people can do, and they can value for what I created not for the problems that I have. Is that right?

And so the other part is that you freed you up, because to your point, I think you said it very early on in the call, or the talk here is that, that, you know, as you get to be, you know, as as it grows, you spend all your time on Zoom, and you’re managing and telling people what to do, and you’re not actually building and creating anymore. And so you you, as you remove yourself from that your work satisfaction goes down dramatically. So you almost feel like you’ve done, you’ve been busy all day, but you did no work.

Paulina Masson
But certain type of people would enjoy that. Like, if you feel almost like you would be more comfortable in a job, actually, you’ll be very comfortable managing the business that’s already running. That’s why people like the guys who bought my company, they just all they do that all day, they just acquire companies that already took the hardest part and what I like to do that hardest part, you know, so it’s like, it’s, it depends who you are, and what you want to do with your life. Yeah.

Bob Moesta
And I would say I’m the same entrepreneur, I’m the one who can take nothing from nothing to something. But when it comes to scaling it, I’m horrible at it. I don’t like the work. I don’t like the managing, I don’t like the the compromises I have to make. And I want to tweak more than I actually want to scale. And so it’s one of those things where I’ve learned that once I get something to 10 million, I’m better off selling it because the pain and agony of going from 10 million to 100 million is work I do not like to do but work from zero to 10 million is the work I love to do. And so that’s how I’ve been. And what I would say is I’m a serial entrepreneur, I’m not sure by choice, but more that the my skill sets have drawn me to those situations. And so most people don’t set out to be a serial entrepreneur, but you become one because you learn to love that first part that you have.

Paulina Masson
Know, what else is good about serial entrepreneurship, I sold one business and I put some money aside for the next one. And then so I’ve been doing that already without selling the other ones, they were just like changing in the market. So via the the first business like the job IBM was funding my first business and then that business was kind of dying the first one and then was funding the next one, then the next one just market was changing. So it was also dwindling down. So that was funding the next one. And now I sold shopkeeper and shopkeeper sale, I put aside some money to start CreatorBooks, and then I’ll just keep it. So it’s really a nice, comfortable way of self funding, you know, in this chain that way? Well, it’s

a way to build security in so think about as you’re trying to build security and to know that you’ll have something else because what you have is the confidence to create things. But at the same time, now you have the funds and the reserves aside to help you go do that.

It takes a lot of stress out like I’m always about avoiding the stress, and in looking for investors is like its own job a full time job. And if you can completely take that out of the picture. Plus working with any partners or working with any, like poor people in the company, I’m not that kind. I’m a solo person. Sure, I always have employees around me to do the task based type of thing. But I’m, I’m not good at partnering or taking investors on. So that’s also another thing why I wanted to sell the company because when you grow bigger, you have to have other people that are decision based, not task based. And I’m the best working with task based people. So it’s because I don’t like okay, we’re gonna make it green or red, and you make it blue in the end. So both of you are like, oh, you know, it just doesn’t work I wanted to red is gonna be read. And I want to make them five minutes with no overhead of chatting with someone. And I was just like I said, it’s gonna be fun, you know, this way.

Bob Moesta
The other part though, is a lot of times you don’t have the data to make those decisions. So you can make it red. And then you can learn about why read works or doesn’t work, you might end up in blue anyways. But you’re better off to make a decision and get feedback on it, then make no decision or spend too much time trying to figure out what that decision is and so or what that thing is and so part of this is you love you love the puzzle and trying to figure out how to make the puzzle work.

Paulina Masson
Exactly.

Bob Moesta
I don’t want to I don’t I don’t want to I don’t want to actually frame the puzzle. I want to break it up and go do another puzzle.

Paulina Masson
When you overcome the challenge without somebody else I told you it’s gonna work. I don’t want this. I told you I want to figure it out. And then I’m like, yes. Yeah,

Bob Moesta
I think the other thing to realise is that at some point in time, though you had the intent to sell it. It’s that fact of knowing kind of when is it time and knowing where the limits are and what I would say for me as an entrepreneur Are my first two I actually stayed too long. And I had that option to stay. And it was one of those mistakes I made where I never did it again and knowing who you are and what you’re about and to map your career path, or your entrepreneurial path is one of those things where you don’t know what you’re going to do. But you know, you’re going to rotate every two to three years, and you’re going to build something and sell it. And at some point, you’re gonna, you’re gonna get to another point where you’re like, alright, what does progress really mean? And it might be, instead of doing it, it might be helping others. And so you start to realise that as you mature through this process, your notion of progress will change, but to know, like, what are the signals to know when I should sell? And why do I want to sell, and in most cases, you want to sell because at some point in time, like you’re not having fun anymore, and at the same time, you can go get some resources, and some revenue, or some capital to go build something new, which is the stuff you love to do. And so it’s that notion of once it works, it’s like, Alright, how do I do it? And you don’t want to, you don’t want to worry about investors, because at some point, it’s all about pleasing them. And you’d rather say, don’t invest in me, just buy me. Right?

Paulina Masson
Yeah. You know, let me share a little bit about the actual preparation to sell, like, what did I not do and what should I done?

So the most important thing, when you already have in mind that you’re gonna sell your decisions change, for example, I used to mix up personal expenses and business expenses a lot, because I fly there and to this conference, I used personal business and, you know, all like spend at Starbucks, I have to log that transaction, because I use some for the business of the whole transactions of my personal spend have to be logged now. So I had like 11 bank accounts, that the buyer had to fiddle through and I had to put together nicely to okay, this is business expenses, not this is this, this is a, that was horrible. So now I know, for the next company, I should not mix up personal and business just have special bank accounts. And it was it was 11 of them. Because, you know, I lived in Canada, so Canadian dollars, PayPal, Canadian dollars, PayPal US dollars, and then you know, TransferWise, and then all these different accounts. So that’s important.

Another thing that in the building of the software, when you know, you’re gonna sell, you make very different decisions. It’s not like, let’s give them whatever, but you know, that you’re not gonna get to that scale yourself, like, most likely when the scale comes, they’ll have to rebuild that component anyway. So you don’t spend time over engineering things and you make decisions based on on that fact that you’re going to, for example, until we sell, we’ll have 12 features for these 12 features, do we need that capability in the code or not? No we don’t, so we don’t do it, you know, if we wouldn’t know that we’re gonna sell like, eventually, yes, we’re gonna need that. So let’s build in, we get to over engineering spending too much. That’s very, also when hiring people, you hire people. With that in mind, I had the best developer ever that I want to work with. And unfortunately, I had to sign something that says three years after sale, you cannot work with the same guy in any project, and is painful to me, because I know how he works. We are good team, like he’s my best full stack developer, I want to make a new project with him. But I couldn’t because I signed something that says three years you can’t work with this guy. So I had another assistant that I knew I might lose the same way; developer I couldn’t like phase out. But I phased out my assistant that is eight years worked with me in all my projects, I phased her out eight months before the sale to be in a separate component. So that I don’t need to kind of sell you know, with the team. So it was like many different decisions you make along the way just because you know you’re gonna sell it will be completely different company and to do last minute type of thing.

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Also things that they asked me, I didn’t even expect they will ask they asked me about 100 questions the broker before selling. And some of them were like, Okay, so tell me exactly percentages of people why they are cancelling and what’s the percentage so who cancelled for the reason they have no more money who cancelled for the reason why. And I had no such statistics. So I had to spend the whole week going through intercom chats, seeing what they said, you know, we didn’t even collect some data on people who were cancelling, you know, so this time in CreatorBooks, we have a box when you press Cancel, you have to enter something a reason to cancel, you know, before you can cancel, and so many different small things that we’re going forward that now I know, you know, when building the next one.

So this big document, the biggest things that I didn’t have were statistics, like how many people are converting? What are the churn rates? Which countries are they coming from? What are the traffic sources? They asked like which SEO works on which countries on how many conversions like my Google Analytics was not hooked up properly to show conversions per each country. I didn’t have the proper tracking on each page for the funnel, you know how the homepage funnel is working? How many people come home and click on this button, I had no such data. So they asked me all these questions, and they have nothing to provide them. So this time, I am so much better setup from the beginning, you know, and that report that they asked him for that due diligence process, you know, the 100 questions is for the due diligence, and then they go and double check all that data, you’re giving them access to all of these places, I have plus one, my biggest problem was I had a lot of little things that I tried so many, many small accounts in many different places with my personal email address. So Reddit ads, my personal email address, and later I had to sell those logins to all of these places, because like I was using email software, ConvertKit, and then something else and a few of them were on my personal email address with like personal credit cards. And when you sell, you have to give a take, they take over the accounts, they even take over the email address of the business, you know, so I had no other choice, but like clean up my personal email address, like change, it was possible. But in some cases, it was not possible. So we basically just took over.

So this time, everything I registered, like sign up for any new account on any new app, it’s always the business email address and the business credit card so that when you give it over, it’s easy, and it’s theirs. They also took over things like Google Spreadsheets, I had big influencer database I was keeping and that also was like on my personal Google things. So you know, again, transferring that all this whole thing was like 1000 lines spreadsheet that we were just like doing due diligence and trust transfer time was like a month, you know, until we get all of it,

Bob Moesta
How long did it take you to actually clean all that up and get to the transaction?

Paulina Masson
In reality, we’ll have more hiccups than just due diligence. But if talking just about that process, two months, I was working everyday, full time just to like transfer over the ownership. It was impossible mess, because I tried million things and I had costs everywhere. And so really, when you run your business, try to run it as much as thinking you’re gonna sell so like, separated, encapsulated into its own buckets that are easy to transfer.

Bob Moesta
Even though you set out with that in mind, the fact is, is that at some point, there were a lot more details about that, that you learned this time that you will not let happen next time.

Paulina Masson
I did the low I first time trying to sell I don’t know what they’re gonna expect. I didn’t know I’m gonna have to like transfer the passwords and so on. You know, it’s just like, I had no idea. Yeah,

Bob Moesta
Can you could you just articulate why I just said you want to sell? Why didn’t you just take VC and grow it yourself?

Paulina Masson
Taking a VC means that somebody’s over your head, wanting you to grow to the hugest company in the world. And then you’ll get a small tiny share when that eventually exits. Plus, they’re gonna push you to grow quickly and exit quickly. And growing quickly. It’s not the same growing quickly is impossibly bad, like, you’re gonna have to, I don’t know, that’s too much stress again, why would you want to have a limited number of years, like I have 20 years left in my life or whatever. And that’s how many minutes working days and how many minutes I’m gonna waste on like pleasing. And I think everyone is who wants to grow big and exit, and I’ll get $200,000 In the end of it, because my share will be 4% I’m better get my seven figures which is 100% Mine, you know, and, and just move on to the next thing.

Plus, even if they don’t bother you, many of them don’t bother you, right, they stay aside. But just the fact that they exist, it gives you this pressure, like you feel like you need to do better than you’re doing you feel always like this unfinished feeling. Instead, I was like, Ah, we’re gonna do this thing. This customer said, the mobile should look awesome. I’m gonna just make this all mobile friendly. And you sit down and the whole day, I’m just spending this, I’m not thinking about what investor wants help us to grow. I’m thinking I’m gonna please this big customer that I just found and how we’re going to chat about it. And how I’m going to implement in the one colours we’re gonna put, it’s just so much more exciting, you know, the type of business that it becomes.

Bob Moesta
That’s awesome. That’s awesome. So how far along are you on for the new business?

Paulina Masson
So we didn’t launch yet in September, we will be launching this time. But it’s great because this time is the same type of customer solopreneur and on solopreneur. Last time, what worked best was informal SEO articles, so not the corporate style, but like very simple and affiliate partnerships. So copy paste now you know, and it’s also a dashboard from the previous one. It was a business dashboard. Now it’s a business dashboard. Now I know not to mess my finances. Now I know you know how many trials I need to get now and like I just didn’t have email list last I’m email marketing, this time I am doing it. For sure. So it’s like, the very important thing that I missed was email marketing. And this time we have masterminds with crypto YouTubers who are my potential customers. So we do Zoom calls like this. And we just chat about, you know, YouTubing and stuff. And that will be like my initial audience who I’m going to launch to, when the time comes. So it’s like, at the same time, it’s an email list, and we do this monthly mastermind calls as well with them.

So it’s like, completely different way, it’s much more relaxed way. And now I know what I’m gonna do exactly, I don’t need to think of where to spaghetti to throw, I know exactly what’s gonna work and how much I’m going to sell it for, and how many articles I need to make how many people I need to hire. Sure, there will be hiccups. It’s a different business. But it’s so nice now to build on the knowledge from before. So like you feel comfortable with decision.

Bob Moesta
It’s the freedom part of it is the freedom, what you love with the freedom about this, and the fact that as it grows, and it gets there, it becomes, almost becomes constraining. And so when it becomes too constraining, it’s like, Alright, it’s time for me to sell it. And here are the numbers I gotta hit. And how do I actually figure out how to exit faster. And so this next iteration is really about kind of, you want that freedom, you love the fact of being able to kind of discover and learn and figure it out. But at the same time, you’re building the infrastructure. So you don’t have to go through all that pain when you go to sell, to step back and have to clean all that stuff up. So it’s way faster on the exit. So then you can do another one.

So you’re just learning how to actually build the flywheel it just kind of turn it faster and faster and faster. And so you didn’t, you didn’t know before, you’ve learned enough from the last time to know what you should do this time. And you’ll learn new things this time as well. But what’s so special about what you’re saying is that this is a this is an example of somebody who knows what they’re good at. Somebody who knows what they love to do somebody who also knows what they don’t want to do. And they also are very clear about when, when they when when to do what they want to do. And so this is kind of like where, where my belief is, most people have to get into life, because most people just kind of stumbled through. And if we can actually help people understand why you’re doing this, and what you can get energy from and what you love to do, and what you what literally you hate to do. So we can shape not only what jobs you have, but when you should switch from one place to another because it’s you’re not actually having fun anymore, or you’re not actually making progress. Right. Yeah. That’s the beauty. Mark, is there any questions? Or anybody have any any comments? Or do you want to

Mark Littlewood
No I’m fascinated, I was sort of frantically taking some notes, I have to say,

Paulina Masson
Really, you are my good son, thank you very much.

Mark Littlewood
I don’t say almost wet myself laughing when you were talking about that, you know, the people that work really hard all day, they don’t get anything done. And you’re like, Yeah, but some people are just like that. Outputs over outcomes…

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Bob Moesta
Pauline is right, that there is a time in your life where you want to build things. And there’s a time in your life where you want to just one thing. And part of it is, it’s your context wrapped around you that, you know, my belief is 20 years from now, Paulina will be like, you know, she might love to create what she might be creating now by painting or sculpting or doing something else besides building software. And so part of it is as we, as we get older, it’s to know what is at the core of what we like to do. But also to understand that sometimes we might have to go outside our comfort zone to make that progress. And so as she gets, as she goes through this, it’s being able to understand, you know, what do you like to do? When is it time to actually move on? And what is the next thing that you want? And so, a lot of times people run from something and they just go to the next thing, as opposed to what you’ve done, which is, hey, I, you got rid of this one business? Well, now what do I want to do? And you you’re thinking about ways in which to kind of leverage even more your learning and your expertise, but at the same time, also cutting out the crap that you don’t want to do?

Paulina Masson
Yeah, maybe you design your own life, you know, and yeah, exactly.

Mark Littlewood
Yeah, that was, I mean, just just fascinating. wasn’t, wasn’t sort of, I mean, I learned some really interesting. Some interesting things that you had your list of 1000 questions? Is that basically your new dashboard? Or have you incorporated that into your dashboard?

Paulina Masson
1000 questions?

Mark Littlewood
So you had a had a broker that experience was really helpful, but they asked the questions that and you’re using that as the blueprint for your new business and the way you’re thinking about it,

Paulina Masson
I had to back in my mind, mostly it’s about analytics and like many questions about analytics, and then there’s a segment about customer conversions, churn, and so on. So it’s all about the stats, and then there’s segment of marketing methods and what worked and how much percentage, you know, and there’s like a segment of the actual market analysis, you know, in it. So like, I just keep in mind those big components that they will expect, and, but really, at this time is still too early, like, I’m still building within launch. I know I’m gonna sell, like at this stage, I’m not thinking about that yet. Like, because we didn’t launch I didn’t look up anything yet. And then, you know, just the website is done. So yeah, analytics is there, but conversion tracking is not there yet. So it’s like, as we go, well, I’ll be adding those things.

Mark Littlewood
Would you use a broker again?

Paulina Masson
Yeah, I definitely go, oh, my god, that was broker was too good. And I talked to a few and you probably have your bias, maybe I’m not gonna say the name, I don’t know.

Mark Littlewood
Say who was it?

Paulina Masson
Okay, Quiet Light Brokerage was the one that I picked because they were so nice. I wasn’t the transaction to them, compared to the other two that I talked to the big ones, I was like, a transaction. And then it was like all about your Canadian company, okay, we cannot do this sale of shares, we’ll have to sell the assets. And when you have assets, you will have this capital gains exemption. And then Canada is like that. And it’s just like, he’s not even from Canada, you know, like, it was very, very personal, very targeted to me, he talked to me what I need to prepare, where I need to get, like what’s going to be expected. And most importantly, in the process, my buyer backed out at some point, he backed out, like, we started the due diligence, and he backed out. And he said, I’m not buying and we are the picking from the five or one. And then the Quiet Light Brokerage, my broker, he’s like, Okay, so let me be this olive oil style and talk to the buyer. And then I was upset on something and he’s, like, talk to me the same way. And I keep buyers together. And always when there was a conflict, he like smooth things out, you know, and always found this middle ground.

It was so nice to have him not to have this confrontation, you know, directly with the buyer is so important that he handled those things. Like I wanted that much money, but he wanted to, you know, this percentage, because they don’t give you like, the whole amount right away. They gave me like 90% right away, and then 10% Over the next year, you know, so we were negotiating over that percentage, you know, it was gonna be the next year like, there were revenue targets. If you reach those targets, you know that then, so yeah, broker was Quiet Light Brokerage was really, really good.

Bob Moesta
Most people, most people say they don’t want a broker, but a broker actually is that person. It’s like having a very good lawyer who knows how to help you make progress as opposed to most lawyers or brokers they very transactional or very matter of fact, and so the more you can find somebody who understand the emotional part of making this transaction as much as the the functional part of the transaction, it’s very, very important.

Mark Littlewood
Thank you so much.


Paulina Masson

Founder, ShopKeeper & CreatorBooks

Paulina is a software developer and serial entrepreneur with experience of building and selling companies she has founded. ShopKeeper was a profit dashboard for Amazon sellers and building the company gave her a deep understanding of what makes a business profitable. Paulina created ShopKeeper for personal use, but quickly understood it could be very useful to other sellers, so opened it up to the public.

After selling ShopKeeper she founded CreatorBooks, a company that aggregates earnings for creators from YouTube ads, Patreon donations, affiliate programs and product sales, so creators can focus on creating new content.

Bob Moesta
Bob Moesta

Bob Moesta

co-Founder, The ReWired Group

Entrepreneur, innovator and ‘the milkshake guy’ from Clayton Christensen’s famous example of Jobs-To-Be-Done, Bob was one of the principal architects of the JTBD theory in the mid 1990s.

Bob is the President & CEO of The ReWired Group and serves as a Fellow at the Clayton Christensen Institute. A visual thinker, teacher, and creator, Moesta has worked on & helped launch more than 3,500 new products, services and businesses across nearly every industry, including defence, automotive, software, financial services and education, among many others. The Jobs to be Done theory is just one of 25 different methods and tools he uses to speed up and cut costs of successful development projects. He is a guest lecturer at The Harvard Business School, MIT Sloan School of Entrepreneurship and Northwestern University’s Kellogg School of Management.

Check out Bob’s other talks here.


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