Episode 585 | Moving Outside Your Comfort Zone with Dr. Sherry Walling

Rob: It’s Startups for the Rest of Us episode 585. Where I welcome Dr. Sherry Walling, my wife, back on the show. We talk about a few things. We talk about moving outside your comfort zone. We talk about the power of relationships with some very specific examples of how having strong relationships, having a solid network helped Sherry with some recent things that she’s working on. We also talk about her book that is coming out in June or July of this year, a book about grief. And we talk about her interest in psychedelic-assisted therapy.
I always enjoy the episodes when she comes on the show because surprise, surprise, we have rapport. We’ve known each other for 26 years, been married for 21. I think this conversation turned out pretty good. The MicroConf State of Independent SaaS Report is in the works, and just three to four weeks from now, we’ll be releasing that report as well as doing a live stream of some key findings.
Producer Xander did a bang-up job this year on mixing things up. I believe 20–25% of the questions were different. We have sentiment about how people felt about the last year, what hiring is like, asked about no code, and asked about just a bunch of topics that go beyond just the numbers and the nuts and bolts. I’ll make sure to mention that once we have the date set. With that, let’s dive in to my conversation with Dr. Sherry Walling.
You know how I don’t drink coffee anymore?
Sherry: Oh God, really? Are you buzzy?
Rob: I drank a latte and I added a shot. I had a three-shot latte today.
Sherry: Why did you do that?
Rob: I feel so alive. This afternoon is going to be a little rough.
Sherry: Says every addict ever.
Rob: Since I don’t drink coffee anymore, I’ve talked about it on the show before, but it makes me anxious like I feel my heart pounding. It really impacts me.
Sherry: I thought that was just you hanging out with me.
Rob: I stopped, but now, I started tea in the mornings, as people know. But what I found is that every once in a while when I have a latte now, it’s great. I’m so focused and productive. Caffeine, highly recommended.
Sherry: Are you going to have a really focused and productive day today?
Rob: At least for the next hour or two until I crash so hard I fall asleep. Thanks for coming on the show.
Sherry: My pleasure.
Rob: Dr. Walling, back again.
Sherry: You had to book me quite a lot of it in advance.
Rob: I really do.
Sherry: My people had to call your people.
Rob: Yes, they did. I’m glad we’re able to make it work. I have so many questions for you. You’re doing so many things right now. I don’t mean literally right now, but you are working on a book. In fact, the book is done. Here’s the thing. You wrote a book like two years ago, I read it, and it’s amazing. It’s a book about grief. It’s called Touching Two Worlds. The title has changed.
Sherry: That is the title we’re going with.
Rob: Awesome. Instead of self-publishing, which you had done for The Entrepreneur’s Guide to Keeping Your Sh*t Together, you decided to go through a publisher. I’d love to just kick us off. I have like four topics to cover today. All things that you’re doing that I think are interesting and at least tangentially related to folks who listen to this show. But I want to find out why not self-publish this book?
Sherry: I was lucky to have the choice. I worked really hard to write a proposal and to work my network and work connections to try to do the traditional publishing route. I just want to, of course, honor that I had the choice, which not everybody does. The reason for me that I decided to try to work with a traditional publisher on this particular project is because it is an expansion of the audience that I normally speak to. While I have lots of wonderful connections in the community that we share in working with entrepreneurs, this book is really written for a much broader audience and more general audience. It’s an audience that I haven’t cultivated per se.
I was hoping that working with a traditional publisher would help me to think about how to better launch a book into a general audience. I also did get it in advance, which isn’t a game-changer in our world in the sense that we can put some funds and resources towards the cost of publishing a book. But I think the advance does help feel like there are resources behind launching the book. Like the book is sort of paying for itself. The book is funding itself in some ways, which I think is really helpful.
Rob: Right. You said that the advance doesn’t make a difference to us, but even 7, 8 years ago, it was a substantial amount of money. It’s not nothing that they’re investing in, which is really cool.
Sherry: Yeah, specifically, I’m working with a publisher called Sounds True, which is a really cool publisher for me to work with. They are kind of like the publisher that does really scientifically informed wellness and personal development. They’ve published authors like Brené Brown, Wim Hof, people who many of your listeners will recognize. To be in that community of authors feels like a really big deal. I’m not sure if it’s going to pan out, but I’m hoping that being published by this particular publisher will help me to get in the room and get some connections with people who I think could really be advocates for this book.
Rob: Yeah, there is an aspect of being part of a club, of being able to reach out to someone like Brené Brown or Wim Hof and say, hey, we’ve been published by the same publisher. That instantly separates you from someone like me. If I reached out where it’s just like a cold email random guy on the internet. I can see there being a lot of value with that.
To get the book deal though, you had to go outside your comfort zone. I remember you contacting 30 agents, right? You kind of need an agent? I don’t know how it all goes, but you were cold emailing, trying to get intros, and just working it. I remember that feeling frustrating/you felt like it was a bit of a waste of time because it wasn’t yielding for like months.
Sherry: Oh sure. Someone told me to prepare for 100 rejections. That’s just to get an agent. That’s not to get a book deal. Ultimately, none of that cold emailing mattered at all. The agent that I eventually got connected to was a connection of a connection of a connection. There was a direct trail of someone that I knew and had spent time with to someone who read the book, loved the book, and passed it on to their agent. Ultimately, of course, it was the network and it was the connections that helped get the deal.
Rob: The person whom you met who made the intro you met at an in-person event, right?
Sherry: Yeah. It was Tucker Max, who your audience may be somewhat familiar with. But yeah, we met at an in-person event. He runs a company called Scribe Media, which helps people write books. I went to a workshop that they were doing about writing memoirs. The dominos felt that way.
Rob: I often say doing things in public creates opportunity. By that, I both mean shipping things like writing, podcasts, video, social media, or whatever, just being out there, shipping apps, shipping products. But also going to an event. For someone like me, I actually…
Sherry: You really don’t enjoy it for a guy who runs a lot of events.
Rob: I enjoy my events, but I don’t enjoy a lot of other events, to be honest.
Sherry: Do you go to any events that aren’t your events?
Rob: Certainly not since COVID. I can’t remember the last event I went to that wasn’t one of my events. But which is part of COVID and just part of the last couple of years of me realizing where I’m at, where I want to go. I actually think that once things settle down a bit, I do think I will go to some other events that I have not attended before. It’s outside my comfort zone. I bring that up because you’ve gone to a bunch of events and I’m sure some of those were outside your comfort zone. But dominoes fall and eventually, you get a book deal almost exclusively because you did that. You took yourself outside your comfort zone.
Another thing you’ve been doing outside your comfort zone recently is asking people for essentially, I call them testimonials. It’s like recommendations or just someone’s name below a quote about your book, right?
Sherry: Yup.
Rob: That’s been a lot of cold and warm emails as well. You’re hammering away at it. You’re doing a good job, but I can tell that you don’t love it.
Sherry: Yeah. I’m getting ready to put together the landing page for the book and then we are also finalizing the print version of the book. Any testimonials that will go on the back cover or to the book jacket have to be in basically this week, even though the book is not coming out until this summer, but those things have to be in and will be on the website.
Yes, once again, I’ve been cold emailing lots of people who would be great to have their name on the book. This worked really well for me before. I actually reached out to Seth Godin. It wasn’t a cold email because he and I had spoken at the same event. I had handshake met him. We weren’t like buds, but I had at least this point of like, hey, remember business of software? He did an endorsement for my first book which appears on the back cover and that was a really big deal.
I’m doing it again. I’ve reached back out to Seth Godin. He was like no, I’m not really doing a lot of blurbs. I was sad. A lot of the people that I reached out to either did not respond or some of them responded with very kind no’s like Seth. Once again, I’m working with the network. It’s people that I know, have met, or have been in their room with in some capacity who have responded.
It’s been so interesting because a lot of very busy people will say, I’ll glance through the book, why don’t you write me a few sample endorsements and I’ll tailor it to make it my own or I’ll sign off on it. I actually really value that. Someone is lending you their credibility. Whether or not they have read the whole book or whether or not they have written all of the words of the endorsement themselves, they’re still lending you their credibility and I hold that in high regard. That matters to me. I don’t want to diminish that.
But then there are some people who have read the book like my mentors, people who I have worked with, and people who are my professional contacts. They’ve read the book and they’ve written long emails that have been so, so meaningful to me in terms of giving me a lot of personal feedback about what the book has meant to them and then writing these wonderful statements of support for the book.
Even though it’s this long arduous process and a lot of the email and a lot of the work that I’ve done has yielded nothing, the people who have responded, oh, it’s been really, really meaningful and encouraging. It makes me really excited to launch the book out into the world because I already have a little circle of fans who are people who are really important to me.
Rob: It’s so interesting. I mean, there are two points on that. One is, it’s hard work and you don’t particularly love it. You are very gifted in a room and you’re very gifted speaking on the mic, in front of a camera. But sending cold email, I would say, is perhaps not high on the list of things that you are best at.
Sherry: Email in general, not my strength.
Rob: But you’re grinding it out. You’re doing what needs to get done to do it. I think the second point is, I know that there’s someone listening to this thinking well, it’s easy for Sherry because she knows everybody and she has this tremendous network, or it’s easy for Rob to do it, similarly when I talk on this podcast. Do you remember 10 years ago when we knew no one and no one knew us in the entrepreneurial space.
Sherry: I still feel like that. I almost didn’t get a book deal because my social media following is so small. They were like, you have 2000 or 3000 Twitter followers? We don’t talk to people like you. They didn’t give a crap about my Ph.D., but they’re really worried that I don’t have enough followers, that I don’t know enough people. I guess knowing people is also very relative because there’s always someone with more celebrity and more connections. It is like you got to start somewhere. You have to start somewhere.
Rob: You’re talking about audience, I was talking about network. The two are different, right? It’s like who knows you is your audience and who you know is your network, that’s how I think about it. I think that you have a pretty strong network. You have an audience, but we’re all still building it. But you’re right, your audience is not as big as some others.
I just want someone listening to this to say, this didn’t happen magically nor overnight. It’s been a decade. I started blogging in 2005, that’s 17 years ago. I started podcasting 11 or 12 years ago. You started podcasting 10 years ago. We started speaking and it’s like how many conferences did I pitch and crickets? No one would take my calls, so to speak. This podcast had 200 subscribers after 12 months of doing it weekly, it was incredible. It’s like tens of thousands now, but you work up to these things.
You getting a book deal and you being able to get these testimonials, it doesn’t happen overnight and it doesn’t happen by accident. Hard work, luck, and skill, right?
Sherry: And risk. My network has come from me speaking. It’s speakers, it’s the other speakers. That’s how I got access to Seth Godin. That’s how I had an afternoon chat with Sam Power. Anybody that I know is almost always because I pitched a conference, got up there, and did it. I’m not the most gifted speaker. It’s not easy for me. It’s still hard and stressful, but that’s been the investment that is now yielding. Any network connections that I have are through that.
Rob: I have a couple of other topics that I want to chat through. I hope we have time for all of them, but the last one that I will get to is you talked to so many founders and you put out so much content about founders. It’s fundamental help, but it’s just like being a high-functioning individual. I want to find us some common things that solo founders struggle with, small teams, et cetera.
But before we do that, you put out a tweet two days ago, a couple of days ago, as of this recording, you said, “100 hours of training crammed into an already full life. I’m glad for the chance to learn and to cultivate a thoughtful, informed voice about psychedelic treatments. Thanks to the team at @mindcurehealth for allowing me to partner with them. And to @MAPS for a great training.”
MAPS is MDMA Therapy Training Program. You have a certificate of completion. Folks have been following your social media or your podcast, Zen Founder, you’ve been talking about psychedelic-assisted therapy for I don’t know, six months, nine months now.
Sherry: A couple of years actually.
Rob: Yeah, I just don’t know when you start talking about it in public. You and I certainly talked about it for several years. I’ll admit, let’s say, five years ago I heard Tim Ferriss talking about this on his podcast. So much of the stuff he talks about to me, it’s just eye roll. It’s like oh, here it goes, off on this thing that’s like nobody else cares about or he’s trying to do it for attention or whatever it is. And then I heard Joe Rogan talk about it. That’s instantly like Joe Rogan’s entertaining, but let’s just say I’m not a big supporter or a fan. A lot of stuff he talks about just feels way fringe or just out there in a way that I’m like yeah, whatever.
But when you started talking about it, you were, like, yeah, this is a thing.
Sherry: You started rolling your eyes, didn’t you? Like oh, here she goes.
Rob: There’s a book by Michael Pollan, is that his name? Michael Pollan. The book is called How To Change Your Mind. He had written really good books about dietary.
Sherry: The Omnivore’s Dilemma.
Rob: There you go, Omnivore’s Dilemma. This is three or four years ago, you had me read How To Change Your Mind. It’s like, oh, okay, this isn’t something people are making up. There are clinical trials and the FDA is involved. There are dozens of tier-one universities that are using psychedelics in therapy.
Sherry: About 70—Yale, Harvard, UC San Francisco, UC Berkeley.
Rob: It’s not a joke. It feels more like a coming wave of something. It’s really helping people. I guess there are a couple of questions. Like any innovation, it’s like people roll their eyes at Web3, which is crypto and NFTs, and like, oh, this is about the people roll their eyes at the dot-com boom, people roll their eyes at whatever other innovations.
When you mentioned psychedelics, your mom might be like, oh my gosh, do you mean drugs?
Sherry: My mom is very worried that I’m a drug addict, by the way.
Rob: What should people know? What is happening in a nutshell? Who will this ultimately help? What’s the benefit beyond traditional therapy and timelines? Give us a five-minute primer on what’s happening?
Sherry: Yeah. We will see in the next five years that psychedelic-assisted psychotherapy will become much, much more common than it is now. And that it will be used to treat a variety of concerns. The common ones like anxiety, depression, post-traumatic stress disorder. There’s also some really promising research related to eating disorders, obsessive-compulsive disorder.
Psychedelics, of course, are a class of medication. Psilocybin is the active ingredient in magic mushrooms, LSD. There’s a lot of work happening with MDMA, which is also the street drug ecstasy. MDMA is not a classical psychedelic, but it’s sort of grouped into this whole movement.
What’s happening is that people are pairing psychedelic experiences, which is usually sort of a fold day under a medicine. They are combining that with psychotherapy, usually 12–15 sessions of psychotherapy and maybe 3 sessions of medicine. And have developed some treatment protocols that the FDA is currently reviewing and they’re in the last phase of that review. Phase III or Stage III, which is the final phase. Very likely we will see the FDA approve MDMA for use as a treatment for PTSD. Psilocybin for use as a treatment for depression will probably be approved in 2023.
I think these are super interesting interventions. It’s the only protocol that involves both therapy and medication that the FDA is approving as a package deal. We’ve long known that the best way to treat mental health concerns is a combination of a biological or biochemical intervention and therapy. But they’ve never been approved in a package before. I think just as an innovation that’s probably really important.
There also is some really interesting promising research that looks at the ways that these medicines impact the brain differently than our traditional psychiatric medicines like SSRIs— selective serotonin reuptake inhibitors—I mean, other medicines that are sort of commonly prescribed for mental health. Psychedelics work a little bit differently. Well, they work a lot differently. They work probably more comprehensively. They work in different parts of the brain all at once.
One other sort of quick thing that I think is really interesting, The New England Journal of Medicine just published an article looking at a comparison between psilocybin—mushrooms—and SSRIs like your Prozac and found that psilocybin was as effective at alleviating depression as SSRIs were. But one of the significant differences that I think is really important is that SSRIs tend to numb emotion on both ends of the spectrum or diminish emotion. Numb probably isn’t the best word.
For example, it makes your depression less, which is wonderful for folks who are really experiencing depression. But it can also make you joyless. It can turn down your capacity for positive affect.
Psilocybin doesn’t seem to do that. The research is still pretty new, but The New England Journal of Medicine found that it was a strong enough study to go ahead and publish it. They only saw that diminished emotional capacity in the negative end of the spectrum, in the depression side. People could still retain their level of joy and enthusiasm even when using this kind of biomedical intervention for depression.
I could obviously lecture about this a lot. I’ve been thinking about it a lot. I think the science is really interesting. Actually, last year, I worked with a company called Mind Cure to do a podcast all about psychedelics called Mind Curious, which folks are welcome to check out. But I think this is something that you just want to have your eye on. You want to be aware of folks who are informed consumers in mental health care.
I think these medicines have tremendous promise. But like all new interventions, there are going to be some bumps in the ways that they’re rolled out. There’ll probably be some folks hanging shingles who aren’t necessarily that qualified who don’t totally understand the science. I’m really wanting to position myself as somebody who can speak the science, but also talk about the practical applications of these interventions and help people really be informed about what’s coming and what might be accessible to them.
Rob: That’s the voice that I think a lot of folks need to hear. I’m guessing, many people may be hearing this for the first time, that this is a legitimate thing on this podcast. That’s why I wanted to talk even briefly with you about it is that this is happening. It’s in fact, psilocybin—mushrooms—are already legal in the state of Oregon for this treatment. They got legalized in the past six or eight months. This is happening. To your point, misinformation may be strong, but there will be people who say they know what they’re talking about, but they don’t. There’s certainly an underground version of this that’s not FDA-approved that’s happening.
Again, Tim Ferriss and Joe Rogan talking about doing mushrooms a few times a year is something they do. To hear how legitimate this is becoming and how effective it is without so many of the downsides of SSRIs have a lot of side effects from my understanding. You take them for a long time versus these are kind of, like you said, more focused treatments that they kind of re-cut the trenches in your brain. Re-cut is a weird way to say it.
Sherry: We talk about resetting the default mode network is the language that will be used. It’s just a good thing to be aware of. There’s a difference between recreational use, there’s a difference between spiritual use, and the sort of area that I’m most curious about is the clinical application. The treatment uses of these medicines.
Rob: We published The Entrepreneur’s Guide to Keeping Your Sh*t Together three years ago. To date, I still see that book getting recommended a lot. I see people talking about it on Twitter. It really has had an impact on a lot of people because it covers all these aspects of a founder’s journey. I’m curious, since then, if you could add a couple of chapters to that book, is there anything that you feel like you’ve learned, come across, or experienced in the past couple of years that you would be like, you know what, that would make it a cool addition to an updated version of that book?
Sherry: To return to where we began the conversation today, I think one of the things that I would want to emphasize more in the book is the power and importance of network. We talked a lot in that book about the internal life of the entrepreneur. We did talk some about relationships, but I think that network is of paramount importance in a way that I didn’t even quite understand then. Network, friendships, we did talk about it, but I think the isolation that has come with the pandemic and the isolation that a lot of solo founders or small team founders already feel is really the biggest mental health vulnerability of the day-to-day founder.
The ability to have a really strong network, to be in a mastermind, to have deep, connected relationships with people who understand the ins and outs of the business and your life, I just can’t emphasize it enough. It’s like the song that I want to sing all the time every day to everybody that I talk to.
Rob: I want to emphasize that you’re using the word network, but I think it’s the word relationships. Let’s say five years ago when I heard network, I was like, oh boy, it’s the person who walks in, hey, I know that person and had this whole I’m playing chess with people and I’m matching them up. But you’re not talking about that, you’re talking about having relationships. Sure there are professional relationships that help intro you to a book agent and then write a recommendation for your book—those are great to have. But you’re also talking about having friends and having both founder and non-founder friends.
Because the founder friends understand you, but you also don’t want to talk about business all the time. It’s like having those people to backstop you and to be like, hey, when we were trapped in the house for six months in a pandemic shutdown, who will do a Zoom happy hour with me? That really brings me joy.
Sherry: Yeah, network maybe has a bad rap. But it’s all the web of connections that support you. Some are much closer to you. The people you live with, the people you’ve known for a long time. Some are getting farther and farther out away from your day-to-today life. But they’re still important connections. People that you can ask a favor for or offer a favor to. It’s those human relationships that are hard to build. Let’s not oversell it. It requires a lot of work. It’s a lot of awkwardness.
I’m not great at developing relationships, certainly not over emails, certainly not virtually. But the importance of figuring out those skills is as important as a lot of the hard skills that go into building the business and promoting the business.
Rob: Yeah. This is something that I learned that I’ve talked about before, but you recall in the 2000s when I was still working full time jobs, I kept saying, I don’t like working with people. I don’t want to work with anyone. I don’t like coworkers.
Sherry: I thought you said that like last week, honey.
Rob: No, that’s not true. Tracy, Xander, Einar, Alex—I like you guys. That’s when I was like I’m going to be a solopreneur. I’ll have no employees and I’m just going to do it myself. What I realized is not that I didn’t like coworkers. It’s that I didn’t like coworkers who weren’t very good, who I couldn’t handpick, who didn’t care about the job, and who weren’t really good at what they did.
I did the solopreneur thing for a few years. And then as Drip started taking off, it was like, I can’t do this as a single founder with no employees or no support. I started building a team around that and learned that lesson of like, oh, I actually really enjoyed being on a team, but a team of high-performing individuals. I thought I could do it all on my own.
To come back to your thoughts and idea of network, it’s like what would starting TinySeed have been like if I couldn’t have just reached out and emailed Hiten Shah, Laura Roeder, and Rand Fishkin, all the people that are mentors. That instantly made TinySeed stand out.
Sherry: It wouldn’t have happened.
Rob: No.
Sherry: You’re really smart and I like you, but I don’t know how in the world it would have happened because you didn’t have that social credibility and you wouldn’t have had access to the people who knew you and believed in you.
Rob: That comes from, like I said earlier, it doesn’t happen overnight and it doesn’t happen by accident. It comes from doing things in public. Doing things in public creates opportunity. It builds relationships and puts you on people’s radars. It puts you in people’s minds as someone who does interesting things, and therefore, it’s like we want to be around those folks.
To bring it back to your earlier comment, it’s not just about business networks and being able to reach out and get a testimonial or have someone be a mentor. It’s also about some deep relationships and having someone to rely on and to help support you.
Sherry: Yeah. I think it’s about realizing that you’re on the journey with other people. You’re not exactly on the same path, but you can sort of see where they are and they can see where you are. You’re watching their progress and legitimately celebrating it. Caring about how they’re growing and developing in their personal and professional lives. Then watching them or letting them care about you. Letting them know like here’s what I’m struggling with. Here’s where my successes are. Here’s this book that I wrote about my family and our losses. You’re invited into my life, into my world. I’ll show up for you as well. That happens, of course, in all these different levels of intimacy. But it happens because you give it attention.
Rob: With that, I think we should wrap up. I know, this is good stuff. But I literally hear the dog barking because I think the cleaners are arriving right now. It’s about to get really loud in the house and we’re at a nice transition point. If folks want to keep up with you on Twitter, you are @zenfounder. You, of course, host the weekly Zen Founder podcast. Your book comes out in June or July. If someone is interested in reading this book, it started as a memoir. You wrote the whole thing as a memoir and then the publisher said put in more, I don’t know what, actionable kind of—
Sherry: Be helpful. Be helpful to people.
Rob: For what it’s worth, I think it improved the book.
Sherry: Yeah, totally.
Rob: If folks are interested in that, they should go to zenfounder.com, sign up for your email list, and you’ll reach out when the book is in pre-order.
Sherry: Absolutely. Thanks so much for having me.
Rob: Absolutely. It’s great to have you. Thanks again to Sherry for coming on the show and thank you for coming back every week and listening and subscribing. If you haven’t given a five star review in whatever podcaster you use, I would appreciate it. If we’re not connected on Twitter, hit me up @robwalling. That’s it for this week. I’ll be back in your ears again next Tuesday morning.