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In episode 715, Rob Walling is joined by Dr. Sherry Walling to discuss a variety of topics. They chat about two recent and meaningful interactions made possible by the Internet, the motivations behind organizing and performing a circus show, and they chat about upcoming launches on the horizon – new books and courses for SaaS founders.
Episode Sponsor:
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We have been partnering with Lemon.io for several years, and they’ve proven to be a great choice when it comes to hiring for a highly skilled developer to work on your project.
Here are five reasons why you should consider working with Lemon.io.
- The time from your request to getting a candidate is just 48 hours.
- Developers have previously worked with tech giants such as Apple, Google, Netflix, Airbnb, Intel, and LEGO.
- They only provide senior devs, with an average of 7 years’ experience.
- Their talent pool covers more than 300 dev languages & frameworks.
- Your hire comes with a zero-risk, replacement guarantee.
Customers of Lemon.io typically stick around for at least a year, proving they know how to gain your trust by delivering consistent results.
Quit wasting time searching for a solid developer at a great price. Get in touch with Lemon.io.
As a bonus for our podcast listeners, you’ll get a 15% discount on your first four weeks of working with a developer at lemon.io/startups. That’s lemon.io/startups
Topics we cover:
- 4:00 – Examples of thoughtful, nuanced Internet interactions
- 8:12 – Impacting people you otherwise couldn’t online
- 15:12 – Dr. Sherry Walling’s circus show motivation
- 21:53 – The psychology of business exits
- 25:27 – Commonalities across founders considering exits
- 31:11 – Speaking to the whole lifecycle of a SaaS business
Links from the Show:
- Apply for MicroConf Masterminds before June 12th 2024
- Sherry Walling (@sherrywalling) | X
- Sherry Walling (@dr.sherrywalling) | Instagram
- TinySeed
- Discretion Capital
- Before The Exit by Dan Andrews
- Episode 532 | The Art of Selling Your Business with John Warrillow
- The Entrepreneur’s Guide to Keeping Your Sh*t Together by Sherry Walling, PhD and Rob Walling
- Enter your email at Robwalling.com
- Sign up for the Zen Founder newsletter
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Subscribe & Review: iTunes | Spotify | Google
[foreign language 00:00:01] Rob Walling. And in this episode, I’m joined by Dr. Sherry Walling, where we have a great conversation, it’s fun. We move from the best uses of the internet. We tell a couple recent stories that have more relevance to us as humans than we talk about, Sherry’s recent circus show and her desire to do that. It’s as much of an entrepreneurial venture as anything is given the amount of time and focus and money and energy it takes to put that on. I asked her why she does it, and I think there’s some lessons to be learned from her journey and what we all do as entrepreneurs. And finally, we talk about our new book, which I say new book, I mean we’re probably still six months out, question mark, from launching it, but it’s a book about selling your company, about thinking through whether to sell it, things that could change, that would make you consider selling it, the mental side of the process, dealing with all the humans involved. We haven’t talked anywhere else about the book in this depth as we do in this episode.
Before we dive into the episode, I wanted to let you know that our MicroConf Mastermind Program is open for applications. I’ve talked a lot on this podcast about how important masterminds have been to my entrepreneurial success, but finding the right founders to join up with can be hard. Over the past few years, our team has successfully hand-matched over 1,000 founders into mastermind groups by looking at your revenue, team size, strengths, goals, and a few other data points to make sure your peer group is the right fit. Once matched, you’ll also have access to our mentorship series, a three-month program where you can connect with some great minds in sales, business development, marketing, and more. If you’re looking for accountability, honest feedback about your business, and the opportunity to make new friends that care about your success, you can learn more and apply today at microconfmasterminds.com. Applications are only open until July 12th, so make sure you sign up before then. Again, that’s microconfmasterminds.com. With that, let’s dive into our conversation.
What’s the difference between a light bulb and a startup founder?
Dr. Sherry Walling:
Something about screwing?
Rob Walling:
Oh my gosh. Light bulbs stop working when they burn out.
Dr. Sherry Walling:
Founders never stop working.
Rob Walling:
No. Burnout. [inaudible 00:02:37] I figured is-
Dr. Sherry Walling:
I love burnout jokes.
Rob Walling:
Isn’t it fun? Is burnout-
Dr. Sherry Walling:
My whole life is like a burnout joke.
Rob Walling:
Something to joke about. Well, thanks for coming back on the show. Dr. Wallings, great to have you here.
Dr. Sherry Walling:
It was a pleasure. Mostly you didn’t have anybody else, so you’re like, “Hey, will you be on my podcast?”
Rob Walling:
Did you just say it was a pleasure as if the episode’s down? I just think, “It is a pleasure?” Kind of checked, we’re 48 seconds in-
Dr. Sherry Walling:
It was a pleasure to be asked.
Rob Walling:
Oh my God, it was a pleasure just to be nominated.
Dr. Sherry Walling:
I’m happy to be here.
Rob Walling:
Oh my goodness, we’re off to an amazing start. Okay, so I want to kick us off. We’re going to dive into all kinds of fun stuff today about motivation, about the exit book we’re talking about, maybe even talk about a circus show. But I want to kick us off with a story from you: the best use of the internet. Tell us this story.
Dr. Sherry Walling:
This is a good story related to this aforementioned circus show.
Rob Walling:
That you hosted.
Dr. Sherry Walling:
That I hosted. So I wrote and produced and starred in…
Rob Walling:
Geez.
Dr. Sherry Walling:
… sounds very pretentious, a circus show in honor of Mental Health Awareness Month, so using movement art to really depict what I think is a core idea about human flourishing. We’ll talk more about the details later. But anyway, so I’m putting together this show, I’m doing a lot of promotion for the show. Basically everyone I know or is connected to me on social media is probably overhearing about this show. But one of the things that I was doing was looking for visual images to depict the ideas and the characters in the show. And so, of course, like a good tech person, I go to Dall-E and get some cool images that depict this idea of the mind, body, and soul in this certain color scheme that we’re using as characters in the show.
I think that’s a perfectly fine way to go. The images are fine, they’re okay. But I got a message from a woman who is a local artist, a tattoo artist and a painter, and also dabbles a bit in circus, so I know her peripherally. She sent me a message and she was like, “Hey, just so you know, a lot of visual artists are really struggling with AI-generated art. We’re triggered by it. It is replacing us. We’re getting a little lost in the story of AI-generated art.” I was like, “I completely understand.” She said, “Basically, you might not know that it might be upsetting to some people in your community that you would use images like this.” And then she said, “I know you’re doing this show, I know it’s really important to you. I wonder if I could help you create some art for it that is really from a thoughtful, soulful, non-artificial intelligent way.”
And so we talked about how I don’t really have budget for that line item for the show. We talked about some other ways that I could in kind reciprocate. But anyway, she made this really beautiful art for the show. I actually have it right here. I think it’s really beautiful, really captures the spirit, really colorful. I loved the best of the internet story because she saw that I posted something that bothered her, not deeply made her, but just bothered her, and she doesn’t know me very well, but she took at the time to write me a very thoughtful note, gave me the benefit of the doubt, wasn’t accusing, wasn’t like, “Hey, you’re clearly aligned with the robots and hate all artists.” It didn’t make it this polarizing discussion, but she just spoke her truth about it in a very thoughtful, respectful way and then offered to help, offered this collaborative, kind solution.
I know that not every AI-generated piece of art is going to generate that kind of warm human interaction, but I really loved the way that she handled it as opposed to all of the potential ways that could have been much more inflammatory. It also really gave me a space to super celebrate her artwork both on the internet and in 3D, and it was a big poster for the show. So I like the story.
Rob Walling:
Yeah, there was some nuance. There’s nuanced thinking of like, “Oh, it’s not all bad or all amazing.” And also it sounds like she came in with a posture of questions, of genuinely seeking to find out your thoughts on it, offering a solution instead of just raising… How many people approach you-
Dr. Sherry Walling:
It just wasn’t a rant.
Rob Walling:
Yeah, it’s a rant. How many people approach me about my businesses or stuff I publish or MicroConf, it’s just, oh, problem. “Did you know there’s a problem here? Oh man, there’s a problem here. You should really fix that problem.” And it’s like, “Oh, what are you doing to help fix that problem?” I think as a community, we could all fix that problem. She wasn’t saying, “Oh, you created a problem and you should fix it.” She’s like, “How can I offer to help?” That’s great. I love that story.
I have a best use of the internet story as well, not at all related to startups or entrepreneurship at all. But little known fact, I set the record at my high school for the 300 meter intermediate hurdles. I set it back in 1993. I don’t think about that at all. Obviously it was something that I probably should be proud of. It was a great moment. I remember the moment it happened. I remember qualifying for the state meet in California that year, which is hard to do. And I remember breaking the record. But since I left school, I just haven’t thought about it. My track coach from that year pings me every five years or so on Facebook Messenger and says, “You still have the record, no one’s beat it. You still have the record.” So he thinks about it more than I do because he’s involved with it, it’s a point of pride for him. It was his first year of coaching.
And so I get this Facebook Messenger message from a guy I went to high school with, and I have not talked to this guy since the day we graduated in 1993. He says, “Someone just broke your record, 31 years.” And he said, “My son runs for our same high school we went to, and is a really good friend of his. I’ve watched this kid go after your record all year, and he just broke it.” He said, “I think there’s a video of it too. I can send it.” I was like, “What?” A, I was like, “Are you trying to scam me out? Do I need to wire you money?” This is so out of the blue. Again, I haven’t thought about this in forever.
And so he sends me a video of the race, and this kid, I mean, he’s a seventeen-year-old, he’s junior, he’s way ahead of the rest of the field, just destroying them. My friend said, “It makes me realize actually how much of a badass you actually were.” It was such an odd comment, but it just came out of the blue. He says, “Seeing how dominant this kid is and to know that you were running this in the ’90s, that’s a big deal.” So it impacted me a lot in a way, all positive. I was not upset. I was not sad. I don’t think like, “Oh, my record.” All I thought of was, “Good job, kid. Good job. Super proud of you.”
Dr. Sherry Walling:
I love too that you know this kid was gunning for you.
Rob Walling:
He was.
Dr. Sherry Walling:
You know that he knew the number and he knew that you said it, and he’s like, “I’m going to get Rob Walling’s record.”
Rob Walling:
And my name and number, they have all the records, so my friend said, “He was gunning for Rob Walling’s record.” That’s just such a trippy thing because, again, I don’t think about it that way, but he has no idea who I am. I’m wondering if my friend ever told him that he ran track with me. Maybe he did, maybe he didn’t, but I’m just some amorphous person who ran this 39.30 time in the hurdles. So I thought about it-
Dr. Sherry Walling:
Until…
Rob Walling:
Yeah, until he broke it by three… well, 2500ths of a second. I was really impacted by it in a way. It made me nostalgic, but it also made me super proud of myself for being 18 and doing that. It also made me really, really happy for this kid. Just really happy that he could share in that joy. I don’t need the joy anymore. You know what I mean?
Dr. Sherry Walling:
You’ve accomplished some things.
Rob Walling:
Yeah, I don’t need the joy of being the record holder. It just doesn’t matter. So I sat down and I recorded a video, a three-minute video on my iPhone, and I said, “Hello,” insert kid’s name here. “My name’s Rob Walling. You probably know…
Dr. Sherry Walling:
You know my name.
Rob Walling:
“You know my name.” Oh, it was so funny. And I said, “You just broke my record, and I have nothing but incredible respect for you.” And realize the rarefied air, like our school was… It’s a high school, I think it was started in the ’70s, and the record I broke was set in the ’70s. So I was either the second or maybe the third person to hold it. So now you have this kid who’s the third or fourth person to ever hold this record. And it’s fast. He’s either going to beat his own record or I think it’ll be decades again. This is a hard record to beat.
Dr. Sherry Walling:
He’s a junior, right?
Rob Walling:
He’s a junior, he’s 17.
Dr. Sherry Walling:
He is not done yet.
Rob Walling:
Crazy. And so I recorded this video, and it was just like, “Mad respect for you. Super impressed. Welcome to the club.” There’s three of us, four of us. Obviously we don’t know each other, but it’s pretty incredible. And then I told him, “I’m pretty old now, it’s been 30 years since I broke that.” And I told him how much track and being an athlete has meant in my life, how much it taught me about hard work and about…
Dr. Sherry Walling:
So you gave this kid a three-minute, old guy lesson.
Rob Walling:
A little bit. But I tried to be really authentic, like, “This is the rest of your life in the sense that this-
Dr. Sherry Walling:
Matters a great deal.
Rob Walling:
That’s what I was trying to say, “This matters so much.” I still remember the day I broke it. I still remember the accomplishments that I did in track. Even though I don’t think of them that often, once I do, it’s a big part of my life. So anyways, I sent that to his parents because I had their info, and they showed it to him and he was like, “Whoa, this is crazy.” And then the parents were like, “Oh my gosh.” His dad was like, “You just taught him more in two minutes than… I’m trying to teach him all this stuff, but he’s willing to listen to you because you and he are like the only people that have done it.”
Dr. Sherry Walling:
You’re in this special club that I’m not in.
Rob Walling:
Just crazy. Anyways, that’s my best use of the internet, because without the internet, I wouldn’t have found out about it. It would’ve been months. I couldn’t have sent him a video. Just so many things coming into play of that is really cool, and I hope this has a big impact on him maybe just for a day, maybe for a week, or maybe, like me, for the rest of most of his life.
Dr. Sherry Walling:
I love the impact that it’s had on you, on the sense of connection to that part of you, that 18-year-old version of you. And since this has happened, you’ve gone back and you found the video of the race where you set the record, and we watched it together. You showed it to our son who’s just beginning his track career. I think the ability to connect both with other people that you wouldn’t necessarily interact with, but also to connect with this past version of you feels like quite a gift. Thanks, internet.
Rob Walling:
We’ve been partnering with Lemon.io for several years, and they’ve proven to be a great choice when it comes to hiring for a highly skilled developer to work on your project. Here are five reasons why you should consider working with Lemon.io. Number one, the time from your request to getting a candidate is just 48 hours. Number two, their developers have previously worked with tech giants like Apple, Google, Netflix, Airbnb, Intel, and Lego. Number three, they only provide senior devs with an average of seven years experience. Number four, their talent pool covers more than 300 dev languages and frameworks. And lastly, number five, your hire comes with a zero-risk replacement guarantee. Customers of Lemon.io typically stick around for at least a year, proving they know how to gain your trust by delivering consistent results. Quit wasting time searching for a solid developer at a great price. Get in touch with Lemon.io. As a bonus for our podcast listeners, you’ll get a 15% discount on your first four weeks of working with a developer at lemon.io/startups. That’s lemon.io/startups.
So speaking of a past version of you, just a couple short weeks ago, you were hosting, producing, starring… And you sound like Sylvester Stallone, “I wrote the movie because they wouldn’t let me be… I wanted to be the lead.” I mean, this circus show was an event. It was to how many performers, hundreds of attendees, three different performances, a lot of moving parts. Talk us through what it entailed and why you did it. Why do you do something like this that’s hard?
Dr. Sherry Walling:
So this is the second circus show that I’ve created. It involves 20 artists, and we had 400 attendees over three shows. One of the shows was a continuing education class for licensed psychologists, marriage, family therapists, social workers living in our state, which in and of itself is quite bizarre that the boards of those different entities have to approve an educational activity like this. So they approved a circus show, which I think is pretty cool.
So the shows that I’ve created, both of them, have been an attempt to bring into the 3D, bring into physical artistic expression some deeper observation or truth about human functioning and human flourishing. So it’s a little bit like Cirque du Soleil meets your therapy appointment. So if you could imagine your therapy appointment being acted out by a Cirque du Soleil troupe, that’s our show.
Rob Walling:
That’s a heck of a tagline.
Dr. Sherry Walling:
I only starred in this one because I needed a couple extra acts and I didn’t have any more budget. So I was like, “I guess I’ll do it.” Truth, actually. But I get to work with these extraordinary performers. I think I love doing this work because so much of my work is so intellectual, it’s word-based, it’s thought-based. It’s doing this, it’s having one-on-one conversation with founders, which are hopefully of deep service to them and very helpful to their ability to lead and flourish and function well. But there’s also a whole part of my life as a human and of all of our lives as a human, which is not cognitive and it’s not word-based. And so if we can find ways to have collective or shared experiences together where we’re engaging a topic or learning something or tackling something but not necessarily with this prefrontal cortex, word-based language, I think that people are pretty hungry for those kinds of experiences. It’s what going to a concert does. It sort of sweeps you out of your mind and into the music and into the shared experience of the music that you’re hearing alongside other people. And so, creating a show is about making collective a set of emotions and a set of ideas.
Rob Walling:
And you put a ton of work, time, energy, effort, money into it. What do you get out of it?
Dr. Sherry Walling:
I think I get out of it a sense of I’m doing a bit of what I was called to do. I know that’s maybe a weird, maybe philosophical or spiritual way of thinking about things. But many of your audience members may know I lost my dad and my brother in close proximity to each other, so I’ve worked through grief pretty deeply. We have in our lives in the past few years. One of the things that I just have absolutely taken away from those experiences are the fact that words don’t account for everything that’s important and that art and creativity and movement are absolutely essential to human wellbeing. And so, I can talk about that and I write about it and I tell everybody, but to show it and to invite people into an experience of it is a way of having people know something, not just with their minds, but with their cells, with their whole bodies.
So that’s just part of my mission in life. So when I do something like this or invest all this time and energy, I feel like I’m following marching orders from whatever, the universe, the divine. I also really love to shine a spotlight on other artists. You and I have accomplished a lot in our lives, and I’ve had a lot of opportunity to be on a stage, I’ve had a lot of opportunity to get my ideas across, but to have the opportunity to really cast the focus on other artists feels extremely satisfying to me. I think that’s part of the second half of life work, which is how do we really spotlight people who have something to show and something to say, in this case, the language of movement. So that feels important and meaningful to me. Also, it’s just a thing I think should exist. I think we should have more deep level, meaningful engagement on meaty topics in the creative ways. So that’s what I’m about.
Rob Walling:
Yeah, it sounds like a really nice compliment or in alignment with life’s mission, life’s passion. It’s nice to be able to do something. And that’s where you’re willing to do something hard and invest time, attention, and energy and do something that is mentally and physically and psychologically challenging, but it’s worth it, maybe like playing a sport, being a founder.
Dr. Sherry Walling:
Yeah. It also feels in balance. I talk to a lot of founders who spend a lot of time in their heads, and that’s the job, your value is in the functioning of your brain and your creative ideas and the way that you communicate, the way that you see the world. That’s the unique asset that a founder brings to their company. But I think that there’s a vulnerability to get too heady. And so I talk a lot with founders about hobbies, about passion projects, about legacy work, about having a cause or a thing that you think matters and having that be really important in your life. Not to take away from your primary focus on your business, but as a supplement, as a balancing out of the neural circuitry in your brain so that it’s not using the same things over and over, but is diversified in its ability to see and function and problem-solve and feel like you are in the wholeness of yourself. I can’t tell other people to do that if I’m not willing to do it myself.
Rob Walling:
I want to mix it up and talk about the book that we’re working on about exits, The Psychology of Exits. I haven’t talked much about it on the podcast. I’ve hinted around about it, but…
Dr. Sherry Walling:
Your marketing strategy is like my marketing strategy, which is write a book and then see if people can find it.
Rob Walling:
Hey, can you find it based on some… I used a pen name too, so you can’t even use my real name.
Dr. Sherry Walling:
It’s like a scavenger hunt.
Rob Walling:
Yeah, it’s great. No, but I was just looking in the document, and we have 16 chapters and seven chapters have a first draft. We have 27,000 words, which puts us on pace to be exactly a Walling book, which is right around 200, 250 pages. All the books we’ve written have been that. I guess Touching Two Worlds is a little longer.
But yeah, I want to give people an idea of what’s in the book. Chapter one is Why Is This So Difficult? Chapter two is When Is It Time To Go? So obviously that’s thinking through things that might change or come into play to have you move on. Chapter three is Exit Options. Four is What Does An Exit involve? Then it’s Walk-Away Mindset, Getting The Deal You Want, Why Do You Need A Support Team, Collateral Damage, Minimizing Negative Impact, Who To Tell When And How. And then that’s only the first eight chapters. The rest is dealing with the process and managing it afterwards, and you have your team and all this and that. So why did we decide to write this book? What’s the need? Why are we good at this? Why do we know what we’re talking about? No, but why does the world need this? You and I both came to this conclusion that the world needs it and that you and I are as good a people as any to write this.
Dr. Sherry Walling:
I think we’re the perfect people to write this. You know how bad I am at marketing. But I think we are the perfect people to write this because you’ve been through the exit directly. I’ve been through the exit as your partner, so indirectly, but definitely on the bus for all of the roller coaster of emotions up and down and left and right and upside down. Stop with that, with your face.
Rob Walling:
It was fine. It was easy and fine, best memories of our life.
Dr. Sherry Walling:
So we’ve been through it. And then if we take it a level back, in your work with TinySeed and your work with Discretion, in your work with MicroConf, you’ve been on the periphery/the supportive guiding function, the counseling function for a bunch of exits over time. And in my work with founders, I’ve been on the mindset side like, what’s happening? How do I decide to pursue an exit? How do I get through the exit process? What do I do with myself after an exit?
So we know this topic from every layer imaginable. I think it’s extraordinarily important because it is a thing that people get so stuck on so often, but there’s very little language about that. I mean, again, best-case scenario, an exit is phenomenally successful. Someone walks away with a pile of money, everybody’s happy. That founder is often in the midst of a great deal of emptiness and lossness that is very, very difficult to voice. So anyway, exits are way more difficult than people recognize, give them credit for. You and I know that on all the levels of possibility, and I think I have some really interesting ideas about what to do about that and how to make it strategically preventable to have some kind of… You don’t have to have an implosion around your exit.
Rob Walling:
Yeah. I remember a couple of years ago on this podcast, it was probably three or four years ago, I said, “Look, an exit, you might only do it once, especially if it’s a seven or eight-figure exit. You might only do it once in your life, and so if you’re at a point where you feel like spending 30 minutes talking to someone who has some experience, knowledge, and advice to give on this, ping me directly and I’ll talk to you.” So I talked to, I don’t remember, 15, 20 founders over the course of six months all at different stage. I mean, some of the exits were, “Oh, I’m at sale for 750K.” Other people were like, “There’s a $10 million offer on the table.” All of this is life-changing, and some of it is never-have-to-work-again money. What I realized through those conversations, and you’ve had a lot more and more in depth than I have had, those obviously aren’t the only ones I’ve had, but I just remember it being a very compressed time, I got to see that, “Oh, there’s a lot of commonalities.”
I started saying about 60, 75% of the same things over and over, where I was like, “Oh, you’re in… ” There’s a lot of commonality. And that was when I realized, “Oh, someone should write a book that talks about this side of it.” I told them a little bit of like, “Oh, you should get an M&A advisor or a broker, a great one, a great SaaS one is run by Intervals at Discretion Capital, but there are others out there, certainly quite light and a fee and all that we talk about, but M&A advisor. But then there’s mechanics of it of like, “Ooh, I think about it this way.” But then there was a lot of the mental side of it, of just thinking through, “How do I think through? How am I going to deal with this when I’m in the middle of it? How will I deal with it at the end?”
And there are other books on this topic, right? We know Dan Andrews… Is it Before the Exit, After the Exit? I forget which one it is, but After the Exit. John Warlow’s written three books on this stuff. But we have more to say. In fact, we talk about all those books in the book, like they’ll be in an appendix of like, “Hey, here’s further reading,” but we have our own additions to make and our unique takes and our unique advice. I really feel like there is a gap in the market for this type of book. Look, it’s not going to focus just on SaaS or on tech companies. We obviously have a lot of experience with that in the network, but you also know folks who have tried to move out of agencies, service businesses, even trapeze schools or circus stuff. There’s still real businesses that you can sell. Just because they’re not SaaS doesn’t mean that we won’t include them. And hopefully, what we have to say… I think what we have to say is really pretty valuable.
Dr. Sherry Walling:
It’ll be interesting to see how the book reads because you’ve got two people with different expertise and different ways of thinking and different voices. We’re trying to weave it together to feel seamless, but I think your deep procedural knowledge about exits and your just ways of thinking in decision criteria, to sell or not to sell, you think about, “Okay, if I’m making this much at this point and this much ever this time… ” You make it like a word problem, like a math equation. I just approach that question very differently. I think both are really, really relevant and both are important. So if we nail it, which I have some hope that we will, I think the fullness of the perspective will really, really be an asset to people who are reading it.
Rob Walling:
Yeah, I think about it as a spreadsheet. You think about it as an intuition or there’s a lot of heart and mind going into it. I think about it as an escape room, solving a puzzle.
Dr. Sherry Walling:
You think about an escape room, I think of it maybe as an existential philosopher.
Rob Walling:
Totally.
Dr. Sherry Walling:
What’s the meaning behind this?
Rob Walling:
And that’s what I hope we can bring to this, is there’s a bit about mechanics, a tiny bit, but that’s already been covered in other books, how do you think it through? Here’s the thing, if there’s any criticism someone can give me about The SaaS Playbook or Start Small, Stay Small, any criticism that I will accept because it’s how I write, is it’s like dense. It tends to be succinct, terse. I give maybe an example here or there, but it’s not filled with a bunch of anecdotes about stuff. And, one could think it might be a little dry. I feel like, “Look, I’m very practical about things.” It’s informational, right? Yours is certainly informational, but from a different perspective. I think you drive a lot of, “Oh, here’s a story. Here’s an example. And here’s,” like you said, “an existential question,” rather than, “Are you doing math in your head, or are you really thinking about all the people involved?”
Dr. Sherry Walling:
Ultimately, exits are both, right?
Rob Walling:
Yep.
Dr. Sherry Walling:
They are a math problem of what numbers make sense and they are like, “What is the nature of what is important in my life?” kind of problem. So that’s where, again, I get really excited about this book. I think other people have talked about aspects of that, but probably not with the fullness with which we’ll tackle it.
Rob Walling:
So I’m excited about it. We have about three quarters of it mapped out really well and obviously half of it written, so hopefully coming, I don’t know, later this year.
Dr. Sherry Walling:
What are we launching this book?
Rob Walling:
Don’t know yet, but I do-
Dr. Sherry Walling:
My chief of staff was asking me, “Well, what’s your timeline on this?” I’m like…
Rob Walling:
“Yeah, writing this summer, try to get it done.”
Dr. Sherry Walling:
Because you have a few other things that you’re launching.
Rob Walling:
I have another book.
Dr. Sherry Walling:
So we’ve got to launch all our things. I also am going to do a deeply revised update of The Entrepreneur’s Guide to Keeping our (censored) Together. Well, we are.
Rob Walling:
Totally. I think it could use it, right? I mean, that’s a six-year-old book. It’s held up well, but we have so many more stories, anecdotes, and thoughts. When I read through it now I’m like, “Oh, this is cool. It’s a little light.” I have a lot more to say.
Dr. Sherry Walling:
Yeah, I have so much more depth now.
Rob Walling:
And then, of course, The SaaS Launchpad, which is my precursor to The SaaS Playbook, the early-stage stuff, that book, I keep saying it’s written, but now as I go back and read it, I’m like, “Ooh, this is like 80% of the way.” I need to rewrite a lot of pieces, and I think… Not a lot, but I need to rewrite some pieces. I’m doing a video course through MicroConf called The SaaS Launchpad. I think that’s going to be the next thing I launch. SaaS Launchpad itself as a book I think is behind The Exit Playbook, depending on timeline.
Dr. Sherry Walling:
In terms of launch timeline?
Rob Walling:
Yeah, I could see SaaS Launchpad being next year.
Dr. Sherry Walling:
I do love how you/we are going to be able to speak to the whole life cycle of SaaS business. There’s the launchpad, which is like, “So you’re thinking about making a SaaS company.” Then there’s The SaaS Playbook, which is like, “Here’s what you’re going to do.” And then there’s The Exit Book, which is like, “Here’s how you wrap it up nicely, take your bucket of money and go.” And then The Entrepreneur’s Guide will help you not lose your sanity or your family while you’re doing said books one through three.
Rob Walling:
I’ll tell you what, they have the Star Wars trilogy, right? They have the Unholy trilogy, which is Kevin Smith’s… Was it Clerk, Mallrats, and Dogma I think? Or maybe it’s Clerk, Mallrats, and Chasing Amy. And we are… What is this? A quadrilogy now?
Dr. Sherry Walling:
Quad, yeah.
Rob Walling:
Yeah.
Dr. Sherry Walling:
Unless you wanted to be a trilogy, and then The Entrepreneur’s Guide is like Silmarillion.
Rob Walling:
It’s the lore.
Dr. Sherry Walling:
Here’s what’s really going on in your head.
Rob Walling:
Oh, boy. It’s the deep lore. If you want to read Elvin or Elvish, whatever-
Dr. Sherry Walling:
No, don’t say that. It’s very, very approachable.
Rob Walling:
Oh, boy.
Dr. Sherry Walling:
Yeah. I’ve never, obviously, relaunched a book before. I want to do it that way to retain the title. There’s a lot of reasons to do it. Because it’s not a totally new book, but I’m aiming for 30 to 40% new, which is a chunk. So if you’ve purchased it before, please consider purchasing it again.
Rob Walling:
Oh, yeah. We will make it so it’s worthwhile. And we’ll re-read the audiobook because the audiobook quality is so-so.
Dr. Sherry Walling:
Yeah, and we’re going to do it together, right?
Rob Walling:
I mean, I don’t know. That could be interesting. We’ll have a lot of off-the-cuff moments, arguments caught on tape.
Dr. Sherry Walling:
Remember that big fight we had in chapter four?
Rob Walling:
Yeah, that’s great. Let’s talk about this. Boy, let’s relive some… While we’re at, give me some paper cuts and pour lemon juice on them. This would be great.
Dr. Sherry Walling:
I’m curious, maybe people in your audience know, are there audiobooks that are co-written or co-read by the two co-authors? Because we’re co-writing two books and…
Rob Walling:
Yeah, I have heard some. So if you’re listening to this and you’ve heard it done well, please let me know. I’ve heard some where it’s basically the two authors trade-off chapters. They don’t actually read it together. I can see why that’s the case, because reading it takes a long time, and who wants to sit and stare at each other through an audio or a recording app for that long? But if you’re interested in any of these books, then be sure to go to robwalling.com, enter your email there. I don’t email very often, but that is the hub where all my book stuff comes out. And while you’re at it, head to zenfounder.com to get Sherry’s weekly newsletter, about twice a month, founder mental health and… No, it’s just the right amount.
Dr. Sherry Walling:
It’s not too much.
Rob Walling:
With that, I know that you have to run off to a track meet. I have to take someone to the airport. We are heading on our way. Ready, Break?
Dr. Sherry Walling:
Go team.
Rob Walling:
So thank you again so much for joining me today. Folks who want to follow you on Twitter, you are @sherrywalling. And any other place you want them to go to find out more about what you’re doing?
Dr. Sherry Walling:
I mean, if you are on Instagram, my Instagram’s pretty cool because it’s a cool mix of entrepreneurship and circus. Who doesn’t love that? So that’s @dr.sherrywalling.
Rob Walling:
Thanks again for joining me.
Dr. Sherry Walling:
Yeah, my pleasure. 27 years in.
Rob Walling:
27 years. Each day better than the last.
Thanks again to Dr. Sherry for joining me on the show, and thank you for joining me this week and every week. [foreign language 00:34:47] Rob Walling, [foreign language 00:34:53]. Wow, that’s a lot harder than it seems.