Episode 613 | Hacking Your Founder Psychology

Sherry: It’s not a sexy topic. It’s not going to help them 10x their business. It’s not going to help them scale. I think reading a good book about grief and being very proficient in the language of difficult things can save your business.

It’s a difficult message, because people don’t want to acknowledge that they’ve been in grief or that they’re going to be in grief. I think most entrepreneurs in particular prefer to live in the reality of what they can accomplish, and what they can push through, and to kind of push these soft or more vulnerable realities to the side.

Rob: In today’s episode of Startups For the Rest of Us, I welcome Dr. Sherry Walling back on the show. We discussed several things including the release of her new book that comes out today. It’s called Touching Two Worlds. You can get it at touchingtwoworlds.com or wherever greater books are sold, Amazon, Barnes & Noble, all the places.

We talked about the hustle of launching something like this, the behind the scenes of how Sherry has hacked her own psychology a bit to ask for favors, and ask for endorsements, and ask for people to help promote the book, even though that’s not something that comes naturally to her.

We talk about the grief of entrepreneurship, the grief of sometimes having to sell your company, fire someone, or having to leave a company that you love and how grief, which is the topic of the book, ties into entrepreneurship. Per usual, there is the witty banter and the verbal sparring that you would come to expect from Sherry and I getting on the microphone together. I hope you enjoy this episode with Dr. Sherry Walling.

Rob: As of a few hours ago, you are now a published author. Congrats.

Sherry: I’ve been a published author for a long time.

Rob: That’s true, let’s talk about that. You self-published your first book, the first book that you and I co-wrote. Now you’re through a publisher. Is there that big of a difference?

Sherry: It’s a different gauntlet to run through. You said, now I’m a published author. One of the most difficult acts of publishing I’ve done is to publish in academic journals. That’s really hard. Compared to that, writing a book is actually not that difficult. Because in academia, there’s this level of scrutiny about every word, every citation, every premise. You have to defend everything.

Self-publishing your own book, of course, like hey, you can say whatever you want. It’s just up to you to do the work to get it in front of people’s eyes. It feels like publishing with a traditional publisher is a little bit of a hybrid of that. There’s more scrutiny, there are different phases of convincing someone that your idea is good, valid, and sellable. Each of them have their own kind of world to navigate.

Rob: Right, and we covered you finding a publisher in the last episode you appeared on. We’ll link that up in the show notes. It was quite the hustle, quite the grind for you to do that. I think you cold emailed, I don’t remember what the number was, 30, 40, 50 publishers. Eventually, you got a connection and got an intro to somebody. The story went from there.

I want to start off by saying if folks are interested in buying your new book that literally came out today, it’s called Touching Two Worlds: A Guide for Finding Hope in the Landscape of Loss. They can head to touchingtwoworlds.com. or they can go to Amazon.

It’s a book about grief. It’s a story of your grief losing your dad and your brother six months apart. But it also, I think, transcends that. We’ll get into it later in this episode about how there’s grief and entrepreneurship in a lot of ways, in selling your company, having to fire someone, and having someone quit in imploding. It’s all around us in this space. We’ll touch on that in a bit.

I think I want to find out. You finally made it to this day after writing the book for 6 plus months, 12 months in editing, then you found a publisher, and then it was like another 18-24. It’s literally years in the making. What does this feel like today? You’re at the starting line of promoting the book, but you’re kind of at the finish line of the hero’s journey in terms of getting it out into the world.

Sherry: I think it will feel really good to hold it in my hands. Like in entrepreneurship, there are lots of starting lines and lots of finishing lines. The publication date is the finish line of all of the process that’s gone into making the book, selling the book, pitching the book, and talking about the book, so that all the people would know about the book the day that it comes out. That feels like a version of a finish line.

Of course, it’s also a starting line. It’s the starting line of this book having a life outside of me, a life out in the world. Hopefully, it’s the starting line to more conversations, more podcast interviews, and this other path of now supporting the book in its next phase.

I think the tricky thing for me, as for many entrepreneurs, is to also acknowledge the finish line on the same day that I’m acknowledging the starting line, to sort of take the win to celebrate that this particular part of the process is complete, while also gearing up and being ready for the next phase.

Rob: Yeah, and I think that’s a really astute way to say it. It’s not uncommon that I will say, building your product and launching, now you’re 20% of the way there or now you are at the starting line of this whole new phase which developers and product people don’t think about, which is, now I have to essentially find people who want it, although really even that is backwards, because as we know you start marketing the day you start coding. You’ve done the same thing.

You started connecting with people promoting the book, setting up podcast interviews, and basically trying to get the word out what was it, six months ago?

Sherry: Oh, at least. Yeah.

Rob: Six to nine months ago for a launch date. Again, folks who haven’t launched something, whether it is a book, a product, a course, or software, they often think that the marketing starts the day you launch. But what have you been doing? We’ve been calling it the hustle. You’ve been hustling on this more than anything since you were an intern at Yale, since you had your postdoc.

Sherry: Not the last book. Anyway, we can debate that another time, but yeah.

Rob: Yeah. You hustled on the last book, but you had other stuff going on. This one in addition to your circus show, in addition to you pulling in all the stops with your entire network to basically get on podcasts and get the word out, it’s something I haven’t seen you do prior.

Sherry: The hustle began last November when I needed to do the first round of hustle, which is to get early endorsers for the book. That was me reaching out to all of the high profile people that I know, people who have an audience, people who have some authority in the world, and asking them if they would review the book. That was quite a hustle.

It’s hard to get the attention of really busy, accomplished people, people who are more accomplished than I am, even then you are, and to get their attention long enough to say, hey, look at this thing, will you give me a quote, can I put your quote in the back of the book, et cetera. That was really the beginning.

From that hustle, all of that reaching out, all of that navigating the process of getting quotes, and talking with people about it, came this sort of beginning of the book launch, which is, what’s the best way to introduce this book to the world? I decided to do a very unusual thing, which is to host a launch event that was based around an original circus show, which used circus artists to tell a piece of the story of the book, but became a thing to invite everyone I know too.

Instead of, hey, here’s my book, will you talk about it, it’s, come to the show, you’ll get a copy of the book, it’s me introducing you to the content of the book in this really unusual way. That was a risky decision, because it was a huge investment of time, of resources, and of attention. I’m really glad that I did it that way, but certainly it was a risky decision.

Following the show, which happened in May, now it’s time to do all of the podcasts, interviews, article pitches, and all the other things that go along with a more traditional book launch. It’s been a pretty long hustle, I would say, beginning last November to now. We’re here in July.

Rob: If folks want to see pictures of that show, it’s transcendent. It was absolutely magical. It’s touchingtwoworlds.com. There’s a circus show link or circus event link in the header. You have pictures of it, and a video, soon, will come out at some point. When you said you reached out to prominent, important people for endorsements, did my email get lost? You think it went to spam?

Sherry: I think I figured you would endorse it. If you weren’t going to endorse it, I didn’t want to have the marital complications.

Rob: Unfortunately, I endorsed this other grief book and it would be a conflict of interest.

Sherry: This other grief book is better.

Rob: Yeah. Cold outreach or even warm, lukewarm outreach is not my favorite thing, not a lot of people’s favorite thing. Does it come naturally for you?

Sherry: It’s terrible for me. I am the least marketing-oriented person who’s this successful entrepreneur that I know, because my work and my way of being in the world is so relational. To have a transactional conversation, I’m terrible at it. I can do it, but I’m not good at it.

The cold outreach was really difficult. I think the thing that helped, if anything helped, was really believing in the story and in the value of the work. If I could take myself out of the equation and feel like, oh, hey, will you do this thing for me? That was really uncomfortable. But I could say to people really with integrity and with good energy to say I wrote this book, and I think it’s actually really helpful. I think it has something important to say, will you take a look at it?

It felt easier to ask on behalf of the book than on behalf of myself, which in parallel, I’ve talked with entrepreneurs about all the time. Whenever they feel like they have to do something difficult, we’d reframe it as doing it in service of their business, not necessarily in service of themselves.

Rob: I think it’s a really good reframe. I know that when I am proud of something I’ve done or that I know, it will actually help people. I’m not a salesperson. I’m not good at sales. I used to do sales demos, they’re awkward. It’s just not a natural mode for me.

When I know that I have the best solution, like, no, I know that Drip is better than XYZ, I know that TinySeed is a better model than XYZ, I know that MicroConf is the best community for bloggers. I’m not selling, I’m just telling my truth, but I’m just telling the truth as I see it. This is truly something that will help people. That’s a really good way to think about it.

Sherry: I think one of the challenges with this book in particular is that I’m selling something that people don’t necessarily know that they need and they don’t want to need. It’s sort of like a hemorrhoid cream or something. It’s like, hey, if you need this, you really need it.

It’s not a sexy topic. It’s not going to help them 10x their business. It’s not going to help them scale. I think reading a good book about grief and being very proficient in the language of difficult things, can save your business. It’s a difficult message, because people don’t want to acknowledge that they’ve been in grief or that they’re going to be in grief.

Both are true. But without it being this stated need, I think most entrepreneurs in particular prefer to live in the reality of what they can accomplish, and what they can push through, and to kind of push these soft or more vulnerable realities to the side.

Rob: I would agree, because that’s kind of my natural reaction to it. It’s like, well, I’m not in grief or I have not lost a loved one in the past six months, so I’m not in grief. But I think you’re thinking about it in the right way of you’ve either been in grief or you will be.

Have you approached that objection, head on, in some of the conversations or some of the outreach you’ve had of like, well, this is why all entrepreneurs need this or all humans it. It’s just focused on entrepreneurial grief, it’s focused on everyone?

Sherry: Right, but of course, the challenge is that so many of the people that I know and are connected to are entrepreneurs. Those are the strings I have to pull. I actually had this really long email correspondence with Andrew Warner, which was really thoughtful about this. No matter what you think of Mixergy, Andrew has been a supporter of mine in a variety of ways for this book and for the last book.

He just kept trying to figure out how to make the topic fit with Mixergy. He was like, I just can’t make it fit, I know it’s important and I value your work. I had kind of a similar conversation with Channing from Indie Hackers, just the sense of like when people come to our site or listen to our podcast, this is not what they’re listening for. This is not what they want as customers.

That’s been discouraging to have people who have a lot of following and have been supporters in the past, say, we believe in you, we believe in this project, but it just doesn’t quite fit with the conversation we’re having. I haven’t found a great marketing workaround to that. I just take people at their word and say, hey, I honor and respect that you are the keeper of your audience, and you have a job to do for them.

No one needs to impose a message that people aren’t looking for. It does make it a little bit more difficult to pitch this book than the other work that I’ve done.

Rob: Right, given the reach you have in this particular space. I do appreciate that’s a very thoughtful response from Andrew to say I support your work, I believe in it, but I just can’t make it fit. It’s an honest response. I get the feeling that Channing at Indie Hackers was the same thing.

Sherry: Absolutely, super thoughtful. Again, it’s such a gift for people to even consider bringing you into their podcasts or into their audience. I don’t take that for granted for a moment as a podcaster myself. I feel very much like the mother bear of people who come on my podcast. If their work doesn’t really fit, then I accept that, for sure.

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You’ve kind of been hacking your own psychology. I’m sure you hate that term, because you’ve been getting up at butt crack of dawn, which may be the normal time you get up anyways. Have you been doing almost Pomodoro sprints, where you’re setting a timer and you’re like, I have to get 20 outreach emails out in this amount of time? You know the terms of BDR and SDR?

Sherry: Yeah.

Rob: You’ve kind of been that for endorsements or like I want to get on a podcast or I want to somehow promote this book and let the world know about it. You want to tell us more about your process?

Again, you said it’s not natural, it’s uncomfortable. There’s a lot of folks listening to this who are going to have to do sales calls, going to have to do cold outreach, or going to have to do marketing that is not natural, not comfortable, but they’re going to have to push through it. I’d love to hear how you figured that out.

Sherry: Yeah, there’s a spreadsheet. There’s a big spreadsheet. Spreadsheets are a little painful for me, I’m just going to be honest. I’m a lot more of an artist, creator, psychologist feeling oriented person. I’m a trained statistician, mind you, but spreadsheets are not my favorite.

I have a big spreadsheet. On the spreadsheet are kind of like every podcast in the world that I think I might potentially want to be on. Every person, not maybe in the world, but all of the professional contacts, personal contacts that I have, they’ve got a line in the spreadsheet. A lot of you listening to this podcast might have a line in my spreadsheet.

In this spreadsheet, I’ve gone through and sort of thought about, what’s the connection with this work? What might I want to ask for? Is it an introduction to someone else? Is it for them to simply buy the book? Is it for them to endorse the book, leave a review, or buy the book for their book group or for their company, or whatever?

I have a wonderful friend named Elizabeth Marshall, who’s really good at helping authors execute on a launch. She has helped me go through the spreadsheet and sort of prioritize in a world of finite time, which folks are most accessible, have the strongest connection to, and might be sort of most responsive to the message.

I’m not trying to do it for everyone. I’m trying to be strategic and manage my sanity and my time. It’s been really helpful to have a third-party conversation with someone who can help me think through how to do the messaging and how to manage the prioritization of who to reach out to. It definitely is a system. Every day, I spend at least an hour simply doing outreach for those lines in the spreadsheet. 

The other challenge, though, is I have the hour where I do the outreach, but then thankfully, sometimes people respond. Carving out the time to then manage those responses thoughtfully and intentionally, it’s definitely like a part time job to launch a book well.

Rob: Yeah, and you are doing essentially a what might be a SaaS sales process, where you have the, I forget if it’s SDR that does the outbound web. The SDR and BDR does outbound, and the other one is inbound. You are essentially doing that outbound. Some of it is warm, some of it is less warm, in terms of cold outreach.

You are essentially fielding and qualifying those folks, or in essence, trying to set up appointments and that kind of stuff. I think if you were doing this constantly ongoing, you would hire pieces of this out. You could have someone email on your behalf because you would have a process. But at this point, you’re kind of custom drafting a lot of these emails based on who they are and what they do.

When I say kind of, I think you’re doing quite a lot of customization, which is probably why this whole podcast tour—this is what I call it,  a podcast tour. It’s like a band going on tour. You want to tour through all of these various podcasts.

Sherry: Yeah, and it is a very interpersonal endeavor. These are personal relationships. Certainly, my mailing list will get an email. Certainly, there are one to many forms of communication that are involved in this process. But a lot of it is one to one, especially to people who are gatekeepers of the many, if that makes sense. They’re connectors, their podcast hosts, they have a big newsletter, or things like that. Nurturing those relationships. 

We’ve talked about before, on this podcast, that there’s so much relationality in all that we do as entrepreneurs. I think I’m just immersed in the relationship management of doing that well.

Rob: Yeah, it comes back to that again and again. The Startups for The Rest of Us drinking game is when everyone has to do a shot when I tell the story about how I didn’t like my co-workers, so then I went to start a company, or I wanted to just be on my own with no attachments, no employees, no co-workers and this and that. Then I realized, oh, it’s not actually that I don’t want to work with people, it’s that I don’t want to work with people I can’t handpick and choose to be in a relationship with. These relationships are super valuable, whether it’s for…

Sherry: Control issues?

Rob: Oh, please. Every entrepreneur has control issues, am I right?

Sherry: Some more than others.

Rob: I am the most easygoing, patient, chill entrepreneur to work with.

Sherry: It’s what your t-shirt says.

Rob: My t-shirt says, I with stupid, is what it says.

Sherry: Wait, that seems like it’s insulting to me. Am I beside you in that story? What?

Rob: Moving on. We really haven’t talked much about what’s in the actual book. I gave kind of a broad overview of it, but how would you describe it to someone who’s thinking like, well, I may want to buy this book and have it, I may want to gift it to someone that I know who has gone through grief or is going through grief? What’s in those 200, 300 pages?

Sherry: The broad framing of the story of the book is that my dad was diagnosed with esophageal cancer right at the same time that my brother took a very significant deep dive into mental illness and addiction. Essentially, there was a two-year period of watching them both implode, and they both died. My dad died of cancer, my brother died by suicide. It’s the story of all of these moments of watching this process unfold.

Some of the moments are really funny. There’s this moment of me standing in Target trying to figure out which sheets to buy for the bed that my dad is going to die in and just the surreal nature of that process. I tell it in a way that is quite light-hearted. Then there are much more serious moments, like calling my mother after my brother’s suicide attempt and trying to navigate that.

The book is framed as a bunch of very short stories or small essays that all have an analysis portion, where I’m thinking as a psychologist around what worked about my experience, what didn’t, and what I would recommend to others. More than a memoir, it’s also a very tactical book, as much as you can be tactical with grief.

There are journaling practices, there are breathing exercises, there are letter writing practices, there are things to do with these big feelings. Then I’m sort of representing how I engage those practices in my own life. It’s a little bit of a show and tell kind of process.

Rob: Yeah. When I read an early draft of it, you had sent me a Google Doc, literally, probably a couple years ago now. I was struck by how well-written it is. I know you’re a good writer, but it flows so well, and it’s so engaging. I remember thinking, we’ve just lived through this. Do I want to read about it again?

You told it in stories and anecdotes that some of which I was present for and knew about it more than others. I didn’t know about you going to Target or whatever to try to buy those sheets. Dare I say it’s entertaining in the way that it’s heart wrenching but it’s also entertaining. It’s funny, but it’s also sad. It’s real, but it’s also jovial. There is a lot to it.

I guess, I don’t know that I’ve ever read a book about grief. I don’t know that I’ve ever bought one or that I would have had a need to, but this was so helpful for me to hear from you, even though we’re married. But to hear from you as a psychologist trying to deal with your own grief, it was a nice framing of it for me of A, this is how it feels and B, these are ways to to deal with it. Not even just the tactical things, but the humor. You put humor in there and that’s it, and we forget that.

I remember when my grandmother passed away and you and I went to Las Vegas to her funeral, Finn was our oldest, and our oldest son who’s now 16, I’m guessing, was he 2 or 3?

Sherry: He was 2. Yeah.

Rob: Yeah, super precocious, huge vocabulary. I remember, everyone was kind of somber and he would make these jokes. He’s been like, well, intuitively, I will have that snack or something. I was just like, oh, my gosh, this is so stressful because he’s going against the mood, but everyone there loved it.

It was this light, this humor, and this new life because he’s a young kid. He brought a level of sunshine on this dark moment. I feel like there are many points in your book where I felt that way too of like, okay, this is how I want to view grief as I’m going through it in the future.

Sherry: The book is called Touching Two Worlds to speak to that duality. On one hand, against my will, against my choosing, we both entered this phase of life of lots of darkness, of pain and suffering, and people getting really sick and just sort of falling apart in front of us.

On the other hand, you and I, since you were in this story, too, were both also experiencing flourishing careers, beautiful children, and a tremendous amount of joy. I think the message of my book, if anything, is the ability to navigate back and forth between both, because both are real and both happened to us.

I think a lot of people fear going toward the grief, because they feel like they’re going to get stuck there. They feel like it will be too uncomfortable or they don’t know how to navigate it. But I think it’s only in entering that phase of sort of the shadow that you could really experience the fullness of the other side of the lightness, of the joy, of the playfulness, of the delight.

I think introducing that duality, there’s humor, there’s growth, there’s flourishing, there’s joy, all at the same time. To be present to both worlds, to be able to be comfortable in both, is what’s, I think, essential for us to become the fullness of who we are.

I guess I do feel like the book is particularly relevant to entrepreneurs. It’s not written for entrepreneurs, but entrepreneurs, as a group, get the high highs and the low lows. We kind of live there anyway. I think my experience of grief has been very much informed by my life as an entrepreneur, and the fact that I spend all of my time with entrepreneurs, and the need for them to be able to navigate back and forth between the good and the bad that happens sometimes in really quick succession. I think that has been helpful for me to meditate on. 

The book, I will say, I will echo you, it’s really well-written. I’ve not really had the opportunity and all of the writing that I’ve done to bring my full self to the story. It’s a very personal book. It’s very poetic. There’s a lot of my heart in it. There’s also a lot of my mind, wisdom, and learning. To be able to be part of a project that feels fully me, like drawing on all the resources that I’ve accumulated over my almost 44 years on the planet, that feels so satisfying.

Rob: You should be super proud of it, because it’s one of the best books I’ve read in years in terms of keeping me interested and not because I was part of the story. I’m a very peripheral part, I think I mentioned a couple times, but that’s not why. It’s not why I know this story. It’s just something that’s so compelling and well-told, even though it was off the beaten path for me.

There are times when I stumbled upon an Audible book or a Kindle book for that matter. But I just do a lot of audio, where someone really recommends it to me, and I’m like, this doesn’t seem like something that is going to resonate with me. Then I start listening and I couldn’t stop. That’s how this book was for me. Although I was reading it as a Google Doc, you have it as a paperback, Kindle, Audible.

Sherry: Audiobook.

Rob: Audiobook that you read.

Sherry: Into the big studio.

Rob: Yeah. Folks can really consume it in any way they want to. I hope that folks listening to this, whether they feel like they want to read a book about grief or not, I…

Sherry: It’s like the grief book you don’t know that you need. But honestly, this is the psychologist in me, this is not the marketer. It’s nice to just have one on hand if you need it or if there’s a loss and you need to give a gift that feels thoughtful. I think I also sort of wrote it for the intention of having that go-to resource to give to someone when they’re in the midst of grief, and you don’t know what to say. You can sort of, oh, hey, here’s some thoughts that might be helpful to you.

Rob: Yeah, I would agree with that. So touchingtwoworlds.com. If folks want to find out more, obviously, they can buy on Amazon, Barnes & Noble, Audible, wherever greater books are sold.

You are @sherrywalling on Twitter, if folks want to keep up with you. Of course, the Zen Founder Podcast, where you have several hundred episodes of stuff talking about entrepreneurship, mental health, startups, family, and life. Thanks for joining me on the show.

Sherry: Amazing. Thanks for having me.

Rob: Thanks again to Sherry for coming on the show. If you feel like she’s given you some value over the years, whether through this podcast or her podcast, Zen Founder, it’d be amazing if you could head to touchingtwoworlds.com or amazon.com, barnesandnoble.com, audible.com, wherever you go to buy books, and pick up a copy of Touching Two Worlds. Thanks for listening to this and every week. This is Rob Walling signing off from Episode 613.