From Impossible to Inevitable with Aaron Ross

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Aaron Ross is the award-winning author of Predictable Revenue, a SaaS Sales bible outlining the outbound sales process that he implemented during his time at Salesforce to scale it to $100 Million.

Now he’s back with a brand new book, From Impossible to Inevitable, co-authored with the Godfather of SaaS, Jason Lemkin.

Aaron Joined me on The SaaS Revolution show podcast to discuss the new book and hyper-growth in a business and personal sense as well.

You can listen to the full podcast on Itunes or Soundcloud Now. Below is a lightly edited transcript of the podcast with Aaron.


Alex Theuma:  Aaron, as I’ve said, I’ve been wanting to have you as a guest for a while.  I think we discussed over email that it would be the right time to have you on as you’re coming to launch a new book because you spent a lot of time writing that last year.


Aaron Ross:  I did.  Just a pain in the ass.


AT:  Your first book, Predictable Revenue is fabled in the SaaS industry.  What has this book meant to you?  Have you been able to measure how it’s impacted the SaaS community at all?


AR:  Well, yeah.  Predictable Revenue it’s interesting.  I don’t have a way to measure it except I will say the first time I knew it was starting to take off…now, they call it the Sales Bible of Silicon Valley but 2 or 3 years ago, it was 2011… Anyway, a couple of years ago I keynoted the first Sales Hacker Conference in San Francisco and there was like 200 or 300 people there.  They’re big, if you’ve ever done conferences it’s a bit small compared to others.

I asked how many people have read Predictable Revenue and about 90% of them their hands went up.

My father will say he’s on the airplane.  There’s someone reading it next to him, or the funniest story… this is how I measure is like random occurrences.  My wife, her friend went on a date with somebody and was stopped by his place and it was on his table.  And he’s a trapeze artist.

So I don’t really have a way to measure it except that it happens… it’s like those random coincidences I would never have thought of.

There’s a couple of times on the street I’ve been stopped.  Like, “Hey, are you Aaron Ross?”, in whole foods, “What?”  It’s fun that way.


AT:  I’ll add a story to that.  One of the podcasts I recorded was with a young founder called Jakob Marovt out in Copenhagen.  He’s got a SaaS startup called Pipetop.  And in his customer development phase, I think he interviewed 40 potential customers.  The ones that he interviewed as a thank-you, he bought them all Predictable Revenue and gave them all Predictable Revenue as a present.  I thought that was pretty cool.  Hopefully, they will have read that.


AR:  Yeah, that’s cool.  You know, there’s still time to get a bulk order of the new book before I launch it.


AT:  Definitely.  We’ll talk about how people can do that in a bit.

You said you’ve been working on the new book for some time and this time you’ve been working on it or co-authoring it with Jason Lemkin from SaaStr.  Is this the sequel to Predictable Revenue and what’s it called?


AR:  It’s interesting.  If you don’t know or if you haven’t read Predictable Revenue, you don’t need to in a way.  It’s different.  This book really is a sequel plus a prequel plus an update.  So it sort of not only adds… there’s a whole section there called Nail a Niche which is like the prequel.  It’s like what you need to do before Predictable Revenue.

But the new book also goes into… we can get into that but an entrepreneur’s journey and sales and marketing, so it’s bigger.  It’s much better, it’s bigger, it’s a growth book.  Really it explains and answers these questions you might have which is why am I struggling or why am I not growing as fast as I want?  Like how do I grow faster and how do I keep it up.

The title which was… we’re going to go for like so many damn titles.  There’s definitely some parts I loved about this book and I love books but they can be quite frustrating, which is probably a different story.  But the title is called From Impossible to Inevitable.


AT:  Why the name?


AR:  Well, so Jason Lemkin, if you haven’t heard of him or not follow him, he’s a brilliant guy.  One of the few people I actually follow.  He started SaaStr.  He has a big conference, SaaStr Annual, and the title of the conference this year is From Impossible to Inevitable.

I think where the idea comes from is the beginning of having a company or like having any kind of really big goal, it feels impossible.  Unless you’re young enough to sort of be ignorant about what it takes to do something big.  Because starting a company is hard.  Well, actually starting a company is easy.  Getting it off the ground to make it cash flow positive where you can make a great income can be hard, much less like a $10 million, $100 million.

Anyway, at the beginning it can seem impossible to get to these goals but if you just keep doing the work especially with a SaaS company then you get your first customers then your first 10 unaffiliated customers, you get to like a million ARR and then $10 million.  At some point success is inevitable.  You get the flywheel turning and you can’t help but be successful.

That’s sort of the idea of the book which is how do you take these impossible goals you have and make sure that you will be successful at some point, your inevitable success.


AT:  And you mentioned a bit earlier the prequel element to it, the ‘nailing a niche’, or I think the U.S. folks say niche.


AR:  You and Canadians.  Canadians say it that way too.


AT:  They’re in the Commonwealth with us so I think that’s why.

Can you elaborate why you’re not ready to grow until you nail that niche?


AR:  Yeah.  Well, I can’t speak for Jason but I know from personal experience, because a lot of my personal… the way I make money in my business is mostly around helping companies, I do keynotes.  But usually for years it’s been helping companies build outbound prospecting teams and programs to generate more leads.

Over the years I’ll get companies who say, “Hey, we’re ready to grow, we just need more leads.”  And either we talk to them or maybe I’ve done a project or something happens and realise there’s lots of companies and people who think, “I’m ready to grow.  I need more leads or I should hire more salespeople, I need to start money marketing,” and actually they’re not ready to grow because they haven’t really… they think they’ve figured out who their customer is and what they care about but they haven’t.

And this whole section, there’s actually a bunch of really important ideas in it but one of them is this idea that we call it… most companies you start out, by definition you should be getting customers from your networks: people you know, friends of friends, someplace where you have some leg-up to start.  But the challenge is you get to your first few customers or 50 customers or sometimes people grow to millions through word-of-mouth.  And at some point when you decide you need to grow faster, you need to… it’s about creating a skill to go out and talk, communicate, find and communicate with people who’ve never heard of you.  So your organic growth gets you so far then you need to be proactive growth.

What people don’t understand when you go through with this or you underestimate is you think, okay, we got 50 customers through word-of-mouth in some way and so maybe it will be like twice as hard to get the next 50, because the first 50 were easier, not that they were easy.  Or it’s the same thinking like, hey, we live in San Francisco.  Maybe we’ll just move to San Diego, but it’s not that big a difference.

The reality is like getting, finding and engaging and selling to customers who have never heard of you or your company it’s like you vastly underestimate how much harder that is.  Like vastly.  It’s not like moving from San Francisco to San Diego.  It’s like moving from San Francisco to China.

So what happens, people think, “Oh, you know, it will take us 3 months to grow,” and 2 years later they’re still struggling to really figure out how to grow past in ways that don’t require relationships or word-of-mouth in some way.

In the chapter I go through like why, break it down like why is it harder?  What do you do about it?  How to understand it and account for it.

From impossible


This is kind of a growth playbook. There’s some case studies from these hyper-growth companies like Zenefits and Slack and HubSpot…


AR:  And me, in my personal one.


AT:  And your personal one as well, of course.   When people read Impossible to Inevitable and they take this growth playbook, could there be a ton more SaaS startups getting to hyper-growth and this billion dollar valuation?


AR:  I don’t know about the billion dollar valuation but, yeah, just at least to go from, if you feel like you’re struggling to grow, to having some sense of understanding what does it take, like why aren’t you growing faster and what does it take to grow faster.

My personal story, I went to this myself where after I worked at Salesforce for a few years, left and I was trying some different things.  I was like, I don’t want to start a tech company.  I want to make as much money as I want doing what I love.  I don’t know what that is but I’m going to try.

I did this thing called Unique Genius, which it was helping… like my personal life coaching.  How to make money through enjoyment.  Or to individuals, how do you combine fulfilment and money to that

I did CEOFlow including a book around it, How to Turn Your Employees Into Mini-CEOs.  If you’re a leader, how do you create more self-managing teams.

The thing is, even in those projects, those were really interesting but they were hard to grow.  Like there wasn’t really a way to grow them without that wasn’t incredibly like laborious and unpredictable.

And part of those lessons from me personally and seeing all these other companies is the level of skill that it takes to grow proactively.  You might think when I attend you maybe just need to be like a 3 or a 5 or 7 but you need to be like a 9 to really be able to grow your company proactively.  And for me, that’s when I got married.

Five years ago I got married and had two kids with that marriage from my wife’s prior marriage.  We had a baby right away.  I had this “Oh, shit” moment where, oh, I’ve got to make a lot more money.  And when it came down to what’s the easiest way to make money, for me, it was not Unique Genius.  It wasn’t CEOFlow, but more fuzzier.  It was Predictable Revenue.  It was basically showing companies how to create money.

Going through that whole thing and evaluating here’s these different opportunities.  Which ones are… what does it take to be able to grow?  And then doing it because I’ve grown my business more than 10 times in the last four years.  Under, it feels like a $60,000 – 70,000 income 4 years ago to almost a million dollars last year.

Going through that myself all those lessons went into this chapter.  I think that’s why it’s the number one, it’s the most important.  People so often they don’t understand what place do you have to be in your career or as a company that you’re even able to grow faster.


AT:  I found that interesting because you talk about your personal story there and give that as an example of hyper-growth.  This 10x growth in the last 4 years, for me very interesting to read about as an entrepreneur at the beginning of his journey and certainly would aspire to have 10x growth within 4 years myself, as I’m sure many entrepreneurs who are listening.

That personal element to the book, Impossible to Inevitable pleasantly surprised me.  There was the personal story, there was this motivational, almost self-help kind of feel in some of the chapters.

Define Your Own Destiny, for example.  Personal stories that resonate with the struggles of being a founder and some of the struggles that I’m going through that many of the founders probably listening are going through and some of the hardships that both you and Jason have had.  Whilst you’re doing incredibly well now, you’ve gone through hardships like many of us experience in the early stages.

Why did you bring this into the SaaS growth playbook?


AR:  Well, I think it’s really important to… I believe you have kids, Alex?


AT:  I’ve got one and ½, because the half is on the way.


AR:  A lot of people have kids.  There’s some part in the book it’s if you’re trying to grow your company, you can’t ignore your life too or the lives of your employees.  It’s not that it’s bad or good.  It’s just let’s be real about here’s the environment.  If you suffer from depression, or if you don’t, or if you have…

I have 12 kids now.  The last four years now I’m growing my own personal income in business by more than 10 times.  Family went from 0 to 12.


AT:  Wow. Hyper-growth on the kid front.


AR:  Hyper-growth on family.  Everyone’s got challenges in life.  It’s not bad, it’s just being able to be, I guess, honest about them and not being afraid to acknowledge them.  Because I think when you hide things from yourself or others, so like better just to deal with the problems up front and acknowledge them and work around them rather than trying to pretend they don’t exist.  That’s one part.

And the other part is in the book there’s a whole section called Do The Time.  There’s seven parts, or 7 painful truths, one for each section.  Section 5 is called Do The Time.  The painful truth is it’s going to take years longer than you want.

Like for that big goal, it’s going to take years longer than you want.  And people, we hate to acknowledge that but it means that all the struggles you’re going through and you never don’t have some struggle because, as you go on, you solve some struggles then you get new ones.  Hopefully, they’re better struggles.

But if you’ve been at a company for 5 years and you’re still at like a few hundred thousand in revenue per year or a couple of million, like why is this so hard for me?  Everyone’s just nailing it.  It doesn’t mean you’re doing something wrong.  It doesn’t mean you’re failing.  It might mean you’re just right on this path and doing what you need to do to get… it can be 7-10 years but it doesn’t mean you’re doing everything right.  Obviously, we wouldn’t write there…

There’s a lot of ideas in the book which will be useful but don’t quit.  Don’t give up.  Don’t think you’re failing.  It’s just it takes you years longer than you want.

There’s those lessons which as you’re trying to figure out how to grow, it’s not 30 days, it’s not 90-days, this can be years.  I mean, sometimes it’s faster but you can’t count on that.


AT:  I’m still a little awestruck in not only the 10x growth of your business but the 10x growth of your family at the same time.


AR:  Lots of adoptions.


AT: I don’t know how you’ve managed that because as I say, I struggle with one and ½ and being an entrepreneur.


AR:  That’s the hardest.  That’s actually pretty hard.  But I think once we get to like five, so then after five I think we have our system.  Plus, we adopted some older kids, too, like some teenagers and they’re great.

The hardest, like physically gruelling is that first year with the baby.  That’s the tough one.


AT:  It’s the sleep deprivation.


AR:  It’s physically gruelling.


AT:  I remember maybe the first five podcasts or so that I did was when my daughter was just born and then a couple of months old.  I wasn’t getting any sleep in a 2-month, 3-month period and I was on 4 or 5 cans of Red Bull a day and taking podcast calls with folks in the West Coast at 9:00 p.m.  I was out, I was zonked.  I didn’t know what I was saying.  It was hard but I got through it.  Then you just kind of get the breakthrough and get the sleep pattern.

We’re not turning this into a baby-and-kids podcast but I guess the story perhaps resonates with many of the entrepreneurs out there who have kids.  But yeah, it was tough.


AR:  Right.  And it’s easy.  It’s like you’ve been at it for 3 or 4 years and, ah, this isn’t working so I’m just going to spend tonight, instead of my regular podcast I’ll just watch Netflix tonight.  Then you start doing that more and more and you sort of like don’t consciously give up, you just take your foot off the pedal in some way, or to neutral.

There’s always times… I don’t put a lot of hours into my work.  Most weeks I work 20-30 hours a week.  Some weeks more.  I like to travel.  So it’s not necessarily just the hours that can help but also like the commitment and that willingness to get out of your comfort zone to do things that you know you… it’s like for a lot of people, you probably would want to write…

Like I really want to write a book but you come up with a million reasons why you don’t.  If you just decided, “Here’s the most important thing.  I’m going to write this book,” or, “I’m going to launch this product,” or, “I’m going to do x,” or, “I’m going to do y,” or, “I need to get divorced.”  Like you make that happen.  Because if you don’t put that as the top your whole week can get filled up with all the little tasks that happen every day and you never get to that big thing that you…

Or your anxiety is you just like, “I’m nervous.  I’m going to go check email or look at Instagram for 2 hours.”  All those things get in the way of just staying focused and clear on like I’m going to make this grow, like I have to make this grow.  And I’m not squishy but I’m totally committed to this thing, whatever it is.

Or it could be a relationship.  You can’t be like if you’re one foot in, one foot out the relationship or a business growth, it’s not going to happen.


AT:  I know this book hasn’t launched yet but it’s launching on the 9th of February.  In fact, the day that will coincide with this podcast will be published on the 9th of February.  Actually, that’s the day that SaaStr kicks off, SaaStr Annual.  Have you already been discussing a third book? A trilogy?


AR:  No.


AT:  No.  This is it?


AR:  Yeah.  I have a lot of fun… I’d say that writing this book wasn’t fun.  It was fulfilling in a ways.  It was definitely struggles.  I resonated with someone who said once like every book he wrote is a bestselling author.  At some point during the process, the creative process, he ended up on the floor, like pounding the floor and crying in a foetal position.  I think that there is something.  I think people are just realising that when you do create something that’s new and significant at least to you, you go through those phases.  It’s part of it.

I have a lot of fun in helping my wife with some books that she’s been working on.  She hasn’t published anything yet.  She’s not going to publish it under her own name but it’s been really fun helping her.  So not my own but my wife’s will be out at some point.

Easier with someone else’s stuff, which is also why a lot of people don’t start their own business, don’t write their own book, don’t do their own blog because it’s like, “What will people think?  Ah, probably hate it.”  You got to get over that.


AT:  Who should buy this book and where can the listeners of this podcast and the readers of SaaScribe buy your book?


AR:  I’m going to go back to the first section on Nail a Niche because there’s one really important idea I want to share with people and how to get to that book.  Because there’s a bunch of ideas in the first chapter but one is if you have either a services business or if you’re selling a platform… because I’m sure it’s not just pure SaaS listeners here, but services business and more of a platform business or there’s lots of… if you have a bunch of products, there’s a shift in especially services.  There’s a shift in your mindset that is required in order to grow.  So if you’re not growing yet and you’re wondering why, it’s probably this is one of the pieces.

The thing is you’re used to going… what’s made you successful to get to where you are is that you can talk to a customer or a prospect and you say, “Hey, what are your problems?”  And they’ll tell you their problems, “Okay, yeah, we’ve got some stuff.”

“We can solve that.  Here’s how.”  You’re used to being in that consultative, we can start to do all kinds of things because we know exactly what you need.  We can do it.  That has worked for you until now but that’s what will stop you growing.

The growth mindset is 180 degrees.  It’s you ask them, “Do you have this problem?”  And if they say no, maybe they say yes or no, they don’t have it then you’re, “Okay, were moving on.”  Because there’s one problem we solved.  That is a huge mindset shift for especially services but sometimes platform companies that are used to building anything for anyone.

But let me go back, well, to your question.  People who should buy this book, for sure, if you’re an executive or leader in any Business-to-Business company, CEO, VP Sales, Sales and Marketing, if you care about revenue.  And if you’re CTO, like if you’re a leader but you’re not C-level, like you need to know about how to grow companies if you want to go advance your career whether you’re in tech.  So anyone who is or wants to be a leader in a Business-to-Business company, for sure.

Also to, if you actually, I mentioned at the back, if you read between the lines of the book, if you’re sort of stuck with your career and you’re trying to figure out how to grow it, the same principles that help create hyper-growth for companies is really the same for a person.

I’ve used this myself and, for example, in that last chapter there’s 7 parts, like the last part it’s called Find Your Destiny.  It’s the chapter that kind of like… it’s all the stuff an owner of a company wants to tell their employees but is afraid to.  So power truths that you need to hear if you want to be successful.

I actually mentioned it before we started this, it’s easier to dream than to do.  Which is dreaming is important but at some point if it’s replacing the doing, you’re not going to get to any of those goals.  Those impossible goals you want are going to stay impossible.  At some point, you have to take the steps even if they’re baby steps.


AT:  Before the call we were talking and I mentioned that I was perhaps dreaming for 10 years before I started doing more recently.  I took the easy option and now I’m taking the harder option.  But actually I’m just really, really enjoying it despite the fact that it is tough.


ARs:  Well, I think anything, if you look at having kids is really hard in lots of ways but it’s incredibly fulfilling in other ways.  Starting a business that succeeds is hard in many ways but can be very fulfilling in other ways.

A lot of people don’t have kids, don’t start a business, don’t write a book because they can see what they’ll lose.  Like if I have kids, I’ll lose my freedom or it will cost money.  But it’s hard to see with… it’s like harder, they’re more afraid of losing what they can see they’ll lose versus gaining something they’re not sure what they’ll gain.


AT:  And having kids and starting a business at the same time is crazy.  Or stupid.


AR:  Yes.  Or running both projects in the next years.

I have an amazing life.  Everyday I’m frustrated.  Everyday I’m tired in some ways but also other parts of the day it’s amazing.  It’s all worth it.


AT:  Definitely, definitely.

So where can the listeners and readers buy this book?


AR:  The easiest place is the site.  Of course on Amazon.  I don’t know about different countries but From Impossible to Inevitable on Amazon is probably mostly worldwide at this point.  It’s not translated.  It’s just in English.  It’s going to be, I believe, actually Chinese is the first one we translated it to but it’s a year away.

So or on Amazon.


AT:  I think you mentioned bulk orders as well.  Is that more aimed at the corporates?


AR:  Yeah. there’s information, there’s some bonuses, some gifts.  There’s lots of companies who they want to get it for their entire sales team or their entire company or give them away as part of their own lead generation.  Like you said, the guy who gave the book away to people he met, there’s some people ordering too as part of campaigns or… There’s levels from 1 up to 10,000 books.


AT:  Awesome.


AR:  All kinds of variety.  And you can get a free sample at as well.



Aaron, it’s been a real pleasure to have you on the show today.  I think this is probably the first podcast that I’ve recorded where in fact we’ve included some personal stories and not necessarily just talked about SaaS.


AR:  I personally didn’t want the book to be just like another sales book and like a boring one.  It is different in there’s the art.

And Jason can speak for himself differently but at least for my contribution, I want it to be more like a book.  I want it to read not like another same old sales and marketing book that repeats the same old stuff again and again, blah, blah, blah, blah, blah.


AT:  Well, definitely you achieved that.  cCongrats and I hope the book does really well.




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