Katharine Woodman-Maynard has for seven years created a gorgeous and enduring graphic manifestation of this podcast on the web. I am fortunate to have this gifted artist enhancing my work with her talent and wisdom. She returns to talk about her favorite interviews, to share her journey as a professional artist and to offer valuable advice for those starting out.
Highlights:
Sal Daher Introduces Katharine Woodman-Maynard
Katharine's Perspective of Startups
"... I'm very grateful to you for having connected me with Drew Madson, who founded Readlee. Tell a little bit of the story. How did you connect with Drew?..."
EndeavorOTC
"... I found it fascinating in the interview that Eddie talked about how it was actually shown in trials to be more effective for adults than it was for children..."
"... Human interaction resets us, brings us back to normalcy because if we're off on our own, we go batty..."
Katharine's Professional Artistic Journey
Sticking to a Schedule
"... Once you can learn self-compassion for yourself and realize you're human and you make mistakes and not waste so much energy on being negative and hard, I think you're a lot freer to, advance in your career because you're not so hard on yourself..."
Advice to the Audience
ANGEL INVEST BOSTON IS SPONSORED BY:
Transcript of, “Talent and Wisdom”
Guest: K. Woodman-Maynard
Sal Daher: Hey, this is Sal Daher. I'm delighted you found the Angel Invest Boston podcast in which I interview people who know a lot about building technology startups. I now have a Substack about losing and keeping off 100 pounds of body weight in my 60s. It's called Aging Fit and my goal is to build a community of people interested in keeping fit as they age. Look for Sal Daher on substack.com. Daher, by the way, is spelled Delta, Alpha, Hotel, Echo, Romeo. Enjoy the podcast.
Sal Daher Introduces Katharine Woodman-Maynard
Welcome to Angel Invest Boston, the conversation with Boston's most interesting angels and founders. Today, we have a great treat for our audience. It is the return of Katharine Woodman-Maynard. Welcome, Katharine. Welcome back.
Katharine Woodman-Maynard: Hey, Sal. So nice to be here.
Sal Daher: Great to have you back. Katharine is the graphic artist responsible for the beautiful looks of our website, Angel Invest Boston, but she's also a very astute businesswoman. She has a business as a graphic artist, as a graphic novelist. She's a published graphic novelist and very knowledgeable about this interaction between founder of a startup and graphic artists. Artists tend to be, what was he saying about poets? Was Alexander Pope said something about, all poets are fools, but not every fool is a poet.
Katharine Woodman-Maynard: [chuckles] Right.
Sal Daher: Yes. In this case, this is a very wise artist.
Katharine Woodman-Maynard: Oh, thank you.
Sal Daher: Someone who has a head for business but also is unbelievably creative. Look at her graphic novel, The Great Gatsby. It's just a gorgeous thing. Katharine, since this is a show about startups, let's talk about some of the startup interviews that we've had that stick in your mind. You're doing the graphic work on this stuff. You have a different perspective on it. What things come to your mind?
Katharine's Perspective of Startups
Katharine Woodman-Maynard: One of them that comes to my mind is with psychiatrist and founder, Jacqueline Olds, who created a wearable sunlight tracker called SunSprite. I personally know Jacqueline because I worked as a graphic designer on SunSprite and it was really my first big graphic design client. That's how I got connected with Sal and it sort of started out my career and the capacity to be able to make a living as a graphic designer, which also subsidized my graphic novel career.
I really liked about the interview with Jacquie was she talked about how, this isn't so much about startups per se, but about loneliness in America, that she and her husband wrote a book called The Lonely American. I believe that's the title.
Sal Daher: Yes. The Lonely American.
Katharine Woodman-Maynard: She talked a lot about the importance of community and these small interactions with people and not being so alone in our single-family homes and not having all these interactions with our neighbors. That actually really got me to be more conscious about my life and how I interacted in my community. I live in Minneapolis, Minnesota, in a pretty small neighborhood and I've just found so much joy in actually knowing my neighbors and being able to call on them and trying to be more aware of that. That just personally helped me.
I also think from a career space, I've also been trying to do that in a larger sense where I have almost weekly calls with different cartoonists or artists. I don't consciously be like, "This week I'm going to talk to Sophia," or whatever, but it's just happened that way. I have found the conversations to be so rewarding and so helpful in terms of helping me figure out my career and different advice that people have and feeling connected. That's something I hear again and again in the show is the importance of that founder community, the startup community, whatever community you're part of. Jacquie's interview really helped me get more conscious about that path.
Sal Daher: Oh, every time I talk to her, because she's a neighbor of mine, I run into her, it's such a privilege. It's such a joy because she's such a happy person. A psychiatrist who's happy. [laughs] It's a rare commodity. She and Richard, two psychiatrists who have a good marriage and who are happy. It's amazing.
Katharine Woodman-Maynard: It's great.
Sal Daher: Well adjusted. She went out of her comfort zone in starting SunSprite, which was a device to measure how much sunlight people got because a lot of people in northern latitudes don't get enough sunlight and they get depressed. It was not a commercial success, but I think it was certainly a wonderful experience.
I invest in it and I have no regrets having invested because I got to know, Jacquie, I got to know you. I got to know Ed Likovich, who was the CEO at the time. It's wonderful. It's just wonderful. I think what Jackie was pointing at this connectedness problem that we have is that technology offers us many wonderful things. It has given us the ability to live longer than we used to live, not be worried about getting enough nutrition, and so forth. At the same time, it has a darker side that it can separate us from other people, it can cause us to eat too many delicious things and put on weight, which is a struggle I have, and a lot of people have.
I think the wise thing to do in this, as we confront technology growing ever more powerful, is just to look for the things that the technology can do that make us better human beings and employ it for that purpose. In that interview, Jacquie points to, for example, Zoom rooms, having open Zoom rooms while people who are working remotely are interacting so that they can keep track of what's going on. A little bit like the old Squawk Box and the trading floors. You would know if Citibank had several trading floors and there was a Squawk Box with them, you knew what was going on in the other trading floors and you're generally aware and connected.
This is really important for us to confront technology, not on its own terms, not in the way that it's marketed, but in the terms that serve us, our human needs. I think that this is very much a thing that fascinates me. I think there's a lot to be done in this whole area of just looking for ways for human beings to use technology more in a way that's more humane.
"... I'm very grateful to you for having connected me with Drew Madson, who founded Readlee. Tell a little bit of the story. How did you connect with Drew?..."
Speaking of that, I'm very grateful to you for having connected me with Drew Madson, who founded Readlee. Tell a little bit of the story. How did you connect with Drew?
Katharine Woodman-Maynard: Drew and I met at a Harvard networking event and we just became friends, my husband, and his wife. Actually, Drew is very energizing, "Let's all go do something." He got us into open water swimming. He's like, "Hey, I'm going to this pond in the morning, let's go swimming." My husband and I had been wanting to do that but never had that push. It was actually just an example of, using a community and accountability to get us out exercising.
It was such a great way because Drew has such wonderful energy. If you hear the interview. We would just have these, quick little conversations before we hopped in the water and swam across the pond and back. It was so fun. That's how we became friends. Drew founded a successful startup that he exited from called Readlee. It helps kids learn how to read better, particularly out loud, and using technology to give them feedback.
Along the lines of Jacquie, both Drew and Jacquie, Jacquie is a psychiatrist, Drew as a teacher, was seeing a need that his students had where they didn't have any feedback on how their reading was doing, especially if their parent didn't speak English. He started to realize that, he was encouraging all of these children to follow their dreams, but he wasn't following his dream. I felt like that was a really inspiring thing.
He went on to go to Harvard and get, go to the Ed School and create this company. With both of them, I find that really inspiring. I've been thinking about that a lot in relation to myself because I've been using technology to create videos, explaining different aspects of the graphic novel-making process and different psychological challenges you might have when you're making art or emotions that come up, things like that. People really respond to it and it's been a really positive thing.
I've been, thinking with these inspiring people in my life, how can I expand on that and do that more because it feels like it helps people? I'm sharing something I'm teaching. It's coming back to me where I'm creating this little community of artists that are really engaging. That's exactly what you were talking about, Sal, with how to use technology to create community and not have it such a negative thing, which I feel like when I first started using social media, it was a negative thing. It was just a, "Ugh, I put my art up there and nobody responds, it makes me feel bad, whatever." Now it's just a much happier place.
Sal Daher: The worst thing about social media is so many people who are fooled into thinking that their interactions on social media have any weight at all. It's all manipulated by algorithms and they are not creating any social capital at all with the time they spend on social media. Social media is useful to a certain extent but we have to look at it as a very treacherous servant who sometimes we tell it to do one thing, it will do that thing, but other times it will subvert us and twist us into all kinds of horrible directions.
The idea of seeing Facebook envy, people's perfect lives on Facebook and your life is-- I think Jacquie talks a bit about that in her interview, and how people's lives-- People's lives are never perfect. Lives are always complicated. They never look as wonderful as, like my cousin, always off at some gorgeous location and with his beautiful wife and he's at the beach and so forth. Everybody's like, "Oh my gosh, I wish I could go to the beach," and so forth.
I know that that's not his life. I know he works like crazy and so forth. Every once in a while he goes off to a nice place, but people like envy, "Oh, I wish I could live like that guy." That is very deceptive. It's a treacherous servant. Technology is a treacherous servant, but it is a powerful servant that if we are diligent, we can harness to serve us, we can use it to serve us in a good way.
It's like Aladdin and the genie. It's amazing how these stories are so old. I think that what Drew did was so brilliant because during COVID, the ability to communicate remotely led us into a disastrous, disastrous dead end for people of lower economic means, socioeconomic means. The Zoom class was able to stay home. They had the social capital to stay home and enjoy being with their kids and work remotely and so forth.
People of lower means of less education and so forth had to work grueling jobs, be exposed physically to disease, and then had the problem of what do they do with their kids? They're not at school. They're going to be in some precarious care situation and then on Zoom school. This was a catastrophe, a catastrophe for the people who are not part of the Zoom class, our class.
I think Drew did something extremely valuable for those poor kids who are not part of the Zoom class. His bit of technology was able to use speech recognition technology and help these kids learn to such an extent that it was recognized. Teachers were like, "Oh, this is a really valuable tool. It was one of the few startups that really shined during COVID because of the value that it created. Once again, I think it's like making the genie do what we want it to do and not being thwarted by the genie under the tricks that the genie has.
Katharine Woodman-Maynard: Absolutely. creating that relationship with social media and not letting it derail you and distract you, figuring out that balance. Because for me, it would be horribly detrimental to my career not to use social media. It's figuring out a way that it would be enjoyable to me and that I would have a benefit to others. Once I figured out that I wanted it to benefit others, it made everything clear. It became a lot more fun because I'm like, "Oh, I'm not just doing this to benefit me. I'm helping people." Then it became much more authentic.
Sal Daher: Maybe social media could be viewed as an amplifier of the real connections that we have, the physical connections we have. It can amplify a little bit. You're not going to amplify it a thousandfold, but you can amp it up a little bit. I have more people with whom you would have an in-person interaction and be helpful in that sense. Beware, it's the genie that's on the bottle. It is not a faithful servant.
EndeavorOTC
Katharine Woodman-Maynard: Right. Yes. I think it really leads naturally into Eddie Martucci, which was a recent interview about a device or an app created to help with ADHD, which is something that I suffer from. I was diagnosed in high school from it. It's still something-- I've been able to create my life so that I don't have a lot of distractions. There are times when I really do feel those symptoms come up. I was really excited to hear that interview, which was about EndeavorOTC, which is, well, I'll let you explain it.
Sal Daher: I was an early investor in EndeavorOTC. Eddie Martucci pitched at Walnut and it was just astonishing that it's been long been well known that first-person shooter games helps improve certain aspects of attention, but only certain aspects of attention. It doesn't improve other aspects. It has the pathology, this is the genie, the evil genie here that it can become addictive. Kids become addicted to these games and that's all they do. They have unbelievably fast reflexes, but they can't interact with other humans. It draws them in and it destroys them.
The thought here was based on science from Professor Adam Gazzaley at University of California, San Francisco. There are these pathways in the brain that are engaged. Grossly speaking, you can say that there are two types of pathways. One that focuses people's attention, and another one that blocks out distractions. They created a video game that is scientifically engineered to play with these two pathways and to, over time, build your ability to multitask between these things. Then it actually improves people's ability to function when they use this. This has been validated in clinical studies. Actually, the same app, the EndeavorOTC app, was approved for treatment of ADHD, cleared by the FDA as something that was shown to improve ADHD in children 8 to 12.
Now, I was never diagnosed with ADHD, but I am 68 years old, and my working memory is not what it used to be. I used to have a phenomenal working memory. Long-term memory is still very good. Old age, it's your working memory that goes first. I find that when I started using it, I was the bottom third of the population. I am now almost at the top quarter of the population, the general population. This is not just among 68-year-olds. This is among the entire population. They have 7,000 patients. I'm using this right now. I use it every single day. My wife uses it every day.
It has tremendously improved my ability to engage my short-term memory and to not tell the same story to the same person twice. It's an old traditional thing. As we get older, that's, "Oh, I don't know. Oh, there he goes again." That same story, we've heard it 100 times. It is just an amazing thing.
I should disclose that I was an early investor. I invested in more shares after they did the SPAC and went public. I bought some shares more recently. I'm way underwater in investments in Acquia Interactive. I could have gotten out at a profit at some point, a significant profit, but they reported 7,000 users. Their revenues climbed. They had a really tough slog with the prescription model for children because insurers wouldn't pay.
Now, Endeavor OTC is over the counter and the user pays. It's like $130 a year or something if you get an annual subscription, which I have.
"... I found it fascinating in the interview that Eddie talked about how it was actually shown in trials to be more effective for adults than it was for children..."
Katharine Woodman-Maynard: I found it fascinating in the interview that Eddie talked about how it was actually shown in trials to be more effective for adults than it was for children, which I found really fascinating.
Sal Daher: Older adults, it's more effective for adults, and older adults are super responders.
Katharine Woodman-Maynard: Interesting.
Sal Daher: He speculated that the effect size may be something 10 times. They didn't actually calculate it, but it's entirely possible that the effect size is 10 times that in children. Why? Because, one of the sad things about aging, Katharine, is that the rule that use it or lose it is true at every time in life, but it becomes more and more true. It becomes stronger and stronger. It's multiplied by two, by three, and then it's the second power as you get past a certain age.
As you get older, you need to make a big effort to maintain muscle structure. You lose muscle. It's much harder to build muscle when you're 60 than when you're 40, meaning build as much muscle as you can when you're 40 because you're going to lose some. Or it's going to be hard to maintain. It's better to start with a higher base. The same thing with working memory. I believe that evolutionarily, the idea was that old people were good to have, just like to average out the odds of a saber-toothed tiger coming in and they might eat the slowest-moving old person.
There was some evolutionary value in having old people around, but they didn't have to be particularly strong. A saber-toothed tiger ate you. Doesn't matter, right?
Katharine Woodman-Maynard: Right. They can look after the kids.
Sal Daher: Yes, and they would eat less because they'd have less musculature to eat less and allow the young to have more nutrition so they could reproduce more and so forth. Evolution is tough. Evolution is tough. It's how I can see this. We're fighting against evolutionary pressure. There's no reason for old people to be muscular. There's no reason for old people to have quick minds and so forth, but we can cheat evolution. We can beat evolution at its own game in a certain way. Not entirely. Eventually, we'll go, but we can slow the process.
This is where I think there's a huge potential for EndeavorOTC. 10X effect size, 70 of the 10X for older people precisely because a little, exercising this thing has huge effects. Whereas young people build muscle, for example, very easily. They retrain their neural pathways amazingly. Children are just like, a little bit of work with the kids and bingo, they're on top of the whole thing. Of course, they're not going to stick to it the way an old person would stick to it. That's the advantage of an older person who'll do it every single day, exactly the same time, exactly the same spot. By the way, it bears saying that, keeping the genie in the bottle, so to speak, the great thing about EndeavorOTC is you cannot do it for more than 25 minutes in a day.
Katharine Woodman-Maynard: Right. I think that's very key. It was funny. When I heard this interview, I was like, "Oh my gosh," to my husband. I was like, "We've got to go get this. I'm really excited by it." He read up on it and he was like, "Well, this is only supposed to be for people with ADHD. Then he went online to some survey, and he was like, "Oh, I think I have a lot of the symptoms of ADHD. He's like, and I think my whole family does too. We were like, Christmas presents for everyone?" [laughs] Getting them all subscriptions to Endeavor OTC. Because we were thinking for our parents.
Sal Daher: That's a great idea. I'm serious. Everyone who's, past really 55, I would say, is a great present because I can tell you, I went from being at the bottom quartile to the top quartile and I'm a very busy, I'm an active person. I run all these different businesses and so forth, but my cognition had declined to a great extent.
Katharine Woodman-Maynard: Right. When we've seen this with some of our parents and just seeing it would be a huge benefit. I don't know if we'll be able to convince them or if they'll be offended or anything. We started using it and I am one of the 1% of users that gets nauseous by using it.
Sal Daher: Oh my.
Katharine Woodman-Maynard: It is a driving game. You're turning the phone as you go and--
Sal Daher: You're not supposed to turn you're supposed to tilt.
Katharine Woodman-Maynard: Even with tilting, I get-- I almost threw up.
[laughter]
Katharine Woodman-Maynard: We decided that, although I think this is a great idea that this was not for me. I tried it a couple of times and I was like-- It was also a good lesson in terms of like, I don't particularly enjoy video games or driving games, but I was like, "I should be more serious about my ADHD and look at other interventions that I can be doing."
I love meditation. I was like, "Well, if I'm willing to do 25 minutes of this, maybe I could increase my meditation every day." I think that has been shown to help. Think about other ways to do it. My husband [chuckles] has gotten really into it. He loves it. He thinks it's really fun. He also likes that he never got into video games because he found them so addictive, but now he has the permission to play because it's good for him.
Sal Daher: For 25 minutes?
Katharine Woodman-Maynard: Yes.
Sal Daher: It's good for you for 25 minutes, no more. By the way, Katharine, I had Kevin Majors MD, who's a psychiatrist who does cognitive behavioral therapy. Actually, he teaches cognitive behavioral therapy at Harvard Medical School to students or to interns who are doing their specialization in psychiatry. He says that it can be treated. ADHD can also be treated with cognitive behavioral therapy. You might look into that as a possibility. There are probably some mental exercises that can--
Katharine Woodman-Maynard: Yes, it's tricky because I don't find it-- In school, I found it very challenging because I can't block out people's voices and things like that. Now it's like, I work by myself at home, and but it's--
Sal Daher: You can design your environment.
Katharine Woodman-Maynard: Exactly. I think I should look into that. CBT is a good idea. Yes, so anyway, that was an interesting one. We're excited to see how my husband hasn't been doing it long enough at this point to see changes to his everyday life, but we're excited to see where that goes. Sal, I want to say, one thing I really appreciate about you is how growth-oriented you are, like with the cognition or with the weight loss, and that you're so open about your own journey. I think that's just so inspiring and really great to see because especially, you don't hear a lot of people who are as open as you are. I just wanted to thank you for being that way.
"... Human interaction resets us, brings us back to normalcy because if we're off on our own, we go batty..."
Sal Daher: Thank you, Katharine, I appreciate that. This is one of the things that goes back to our conversation with Jacquie Olds. She has this great story. It's like a archetypal story. You wake up in the middle of the night and you have a horrible, this horrible concern that the world's going to hell in a hen basket and things are horrible. You have all these horrible thoughts. Then you sit across your spouse at the breakfast table and you're having coffee and you look and you realize that all of that was just an illusion.
Human interaction resets us, brings us back to normalcy because if we're off on our own, we go batty. Human beings need other human beings much more than we can-- Let's harness that. I don't want to overshare. Good thing about a podcast you could always turn it off but I find that when I talk about these problems that I grapple with, it has two effects. One is it helps me work out how I'm dealing with it. It helps reinforce the habits that I'm trying to build and so forth and inspires other people. That's a hard thing to do but this guy's doing it. You can figure it out. It's not easy, but it can be done. It gets easier over time.
I think there's a lot of value in people sharing their struggles in the case, ADHD or struggles with weight, struggles with alcohol, and how they're doing, the strategy they're using to contend with it. I think it's extremely valuable because human beings can't do it all. They can't do it alone. If we were just on our own, we would never have survived. How can one person take down a mastodon?
Katharine Woodman-Maynard: Right, no.
Sal Daher: You need a hunting pack. Anyway, maybe what we could do is, at this point, I'll just do a brief promo for the podcast, and then we could get into a little bit of the new directions that you're going in, and some advice, because you are a complete outlier. You are a person of artistic sensibility that manages to make a living at being an artist.
I work with two such people. The other one is Raul. They do it different ways in different media, but there's a certain amount of craft to running art as a business. Some of it is art, but also a lot of it is the habits that make possible this creative enterprise. I want to get into that with you-
Katharine Woodman-Maynard: Absolutely.
Sal Daher: -because you have a lot of wisdom. If you're listening to this and you find this conversation with people like Katharine Woodman-Maynard to be valuable you can help us get found. Trick the algorithm at your podcast platform into paying attention by first following us so that we show up in your feed every week and then giving us a rating and writing a review.
The review doesn't have to be long. A short two or three sentences, well-crafted sentences, is really powerful in helping people discover this effort that we have here, which is really human beings struggling along, trying to figure things out. Nobody pretends to have figured everything out, but there are things that we can learn from each other. That's amazing. There's some wonderful stories about people learning from other people, and they don't even realize.
Anyway, so Katharine with all the experience you've had now, how long have you been working as a production artist?
Katharine's Professional Artistic Journey
Katharine Woodman-Maynard: Since I graduated from college. I had an unpaid internship for maybe half a year, and then segued that into a full-time job as an animator. That was 2009, was when I started, I think, essentially. That's just what I've been doing since I started in animation and then got really interested in graphic novels and transitioned to being more graphic design.
For years, I did both graphic novels and graphic design. Now the graphic novels are taking over, and I'm trying to figure out how-- I have wonderful graphic design clients, but I think that my focus now is going to be more on trying to do more workshops and things, teaching about comics and graphic novels and art. That's what I'm trying to figure out now. I am pretty entrepreneurially oriented, and I love reading books for startup founders.
Sal Daher: It's amazing because your starting point was graduating from Harvard College. There are not a lot of artists who graduate from Harvard. Then, you've had 14 years, almost a decade and a half of working full-time as a professional artist in various capacities in different media, graphic media, but there are different manifestations of it. Can you give us some meta hints to a person who's starting out in this space?
Katharine Woodman-Maynard: I think it's so important to be sacred about your creative time. Sal's seen this where I say I'm working.
Sal Daher: Absolutely. Katharine. Tuesdays and Thursdays, I did graphic work. The other days, graphic novel, other projects, and so forth. Don't even call me.
Katharine Woodman-Maynard: No, I did not say, don't even call me.
Sal Daher: I'm just saying that. I love-- It's like, my dear sister-in-law turns red, Katharine turns red, so I love that these are making her turn red. She's turning red.
Sticking to a Schedule
Katharine Woodman-Maynard: When I started, I used to do mornings, graphic novels, afternoons, graphic design, and then I got a book deal for another adaptation that is not public yet, but I'm very excited for it. It's going to be for a 50-year anniversary of a classic book.
Sal Daher: Oh, wow.
Katharine Woodman-Maynard: It's coming out in 2025. That's why I've segmented now to Tuesdays and Thursdays being graphic design and the other days graphic novels. My point with this as advice is it's really hard to shift your brain all the time, going back and forth from writing or art to then answering emails from a client. I find that it's a lot easier to put your time together, and have that hat on, all lumped together. That's one piece of advice that I think is really important. Also to not have phone or social media. When I'm doing creative time, those are off. I still struggle with it, but it's really important to do, and the work I create is a lot better and faster when I do that.
The other piece of advice is be responsible. Be responsive. I am interviewing students right now for an internship, and the kids who do what I ask them to do with the application, I just ask for a cover letter. The kids who do the cover letter, I'm like, "Okay. They followed what I ask them to do or, they respond to my messages." Really basic social interactions. I think a lot of artists just think that their work will be good enough to get them by, and that is probably true for, a very small portion of people.
For most people, just being responsible and responsive and a good communicator will just get you a large portion of the way and make you stand out. I'm sure that there are many graphic designers who are very good at their job, but if they don't respond to emails, it's not much good to the client.
Sal Daher: Yes, duh. Look, he's a twisted little character, but, Woody Allen is a comic genius, and he said, 80% of success is showing up. Showing up as in responding to emails, showing up as in putting a cover letter and doing the things that are necessary to be present, to present yourself to someone who might hire you for a job because you're going to be shortchanging yourself by not doing that very basic stuff. You know what? These are all habits that can be built. Read Atomic Habits.
Katharine Woodman-Maynard: One of my favorites.
Sal Daher: It's such a powerful book. It's such a powerful book because you can build a habit of responding to emails in a sane way, not that I have been known to delay responses to emails. I just responded to a few of those. Thankfully, Gmail makes things pop up five days after, if it hasn't been opened.
Katharine Woodman-Maynard: Right.
Sal Daher: Things like that.
Katharine Woodman-Maynard: To cut you off, Sal, though, you are also much further along in your career than somebody who's, 18 and looking for their first internship. I think you can not respond immediately to emails.
Sal Daher: No, no, no, no, no, no. The thing is that at my stage of life, I get a lot more emails.
Katharine Woodman-Maynard: Right.
Sal Daher: Believe me. The number of emails I get is unbelievable. You have to build a habit. Once you have that habit, it becomes easier. You can handle those things more easily. Don't beat yourself up over it. You're not going to do it perfectly the first time. Eventually, get on top of that.
"... Once you can learn self-compassion for yourself and realize you're human and you make mistakes and not waste so much energy on being negative and hard, I think you're a lot freer to, advance in your career because you're not so hard on yourself..."
Katharine Woodman-Maynard: My third piece of advice is self-compassion. I think a lot of artists are really hard on themselves. Once you can learn self-compassion for yourself and realize you're human and you make mistakes and not waste so much energy on being negative and hard, I think you're a lot freer to, advance in your career because you're not so hard on yourself. You're more freer creatively. That's been a long journey for me because I tend to be somebody who's very hard on myself.
There's a wonderful book by Kristin Neff, N-E-F-F, she's a psychiatrist, called Self-Compassion. I've read it several times, and right now I'm doing a meditation course based on that. It's just always reminding me just like, wow, when I'm more self-compassionate, so many other things in life come together. I have better interactions with people. I'm more creative. I'm better able to be flexible in my job, all these things. Those are my three pieces of advice.
Sal Daher: No, but this last piece of advice, I'm going to subject it to a decision function, okay?
Katharine Woodman-Maynard: Okay.
Sal Daher: If you are someone who's very focused on achieving things and very on top of things, like Katharine, you need to be more self-forgiving. There it applies. If, unlike a lot of people, especially young people, you are totally unstructured, completely all over the place, and so forth, be a little tougher on yourself. Don't be self-indulgent and expect that other people are going to forgive you for mistakes that you make. In that case, don't beat yourself up, but put yourself in the position of the other person that you're interacting with. Think, "Now, would I like it if I say I'm interested in the job and then I don't show up? I ghost the person on the interview." What does that do? That's wasting someone's time. Someone blocked a chunk of time. I don't show up.
Katharine Woodman-Maynard: Right. I think that's empathy, being able to put yourself in the other person's shoes. The person who you're more describing, somebody who's not quite as type A as me and maybe doesn't have as good follow-through. I think often that can come from lack of self-compassion, that they're overwhelmed by the anxiety and the stress. I almost wonder if they'd be better if they were more freed up because that's a whole part of the self-compassion training is that there's this idea that we won't get as much done if we're compassionate on ourselves because we'll be easier on ourselves. They've shown in study after study that actually people who are more self-compassionate get a lot more done, so that's been fascinating. You should really check out this book. We'll link to it in the show notes.
Sal Daher: Yes. Excellent. I think that's an excellent move to link to that book. I wonder if it's also that idea of self-compassion. It's acceptance of the fact that we're going to fail and that we're not going to do things right the first time. Then we come back at it and do it a little bit better the second time. We'll bang our head against the wall a bit until eventually we really get better at it. There's also that, acceptance of the fact that we're not going to succeed in everything that we do.
I think those things go together in that, but I definitely think that the idea of self-compassion, there are a lot of people who could benefit from that. I know people like that, and really having a better perspective on this is wonderful. It will be really powerful, so Katharine, do you have any other thoughts that you want to communicate to our audience of founders, of angel investors, people thinking of starting companies that you can do that for them?
Advice to the Audience
Katharine Woodman-Maynard: Yes, I do because I've worked with a lot of startups over the years. That's my main clients for my graphic design business, and there are three things that I see again and again that keep coming up that I think founders should work on. One of them is just getting really clear on what your business is, like what your message is, and I know that it's so hard because I have this struggle too.
Sal Daher: This is so true. This is so unbelievably true. Katharine, I was having a conversation this very morning with a very entrepreneurial friend who's, as a matter of fact, he has like an AI platform to help founders hone their message. We were having a conversation precisely about this. I said, "Chris, look, founders have to understand that the message is not just a selling thing. The message is figuring out what your dang business is. What is your business model?" By honing the message, people finally understand what their proposition is. What it is that they're offering that sets them apart.
This is why, as an angel investor, when I see a pitch from founders that they're beginning the race, in the beginning of the race, and then I see a pitch at the end of the race, if the pitch is exactly the same, I say, "These people are not learning. Forget about it." Sometimes I see people, in the beginning, they're a mess, and at the end, the thing clicks. It makes sense. They have actually figured out how to explain to people what their business is, and I think they have internalized also, "This is our business, this is how we can go about it," and they are better founders by going through that process of figuring out the message.
Message is not just selling. Message is not just about sales. Message is about-- it's like when you write an essay. You have to organize your thoughts and then you really understand what you're writing about once you organize your thoughts. Arguments for, arguments against, and so forth. It's the same thing. The message, I agree 100%.
Katharine Woodman-Maynard: Yes. It's the same for writing stories because I write graphic novels and you have to have your one-sentence pitch. I find it so hard. I hire somebody to help me because I just have such a hard time coming up with that description. I think that it's something that as I'm thinking about this new direction, I'm thinking a lot about because I see it again and again. It also makes the job of the designer or anybody else on your team a lot harder if they don't really get in a basic way what you're trying to do. The other thing is be clear on your audience because that is something that's really hard as a designer when somebody is like, "Well, everybody's our audience." [laughs] You're like, "But are they?" [laughs]
Sal Daher: You're going to have different audiences. There's the audience that you start with, and then there's eventually the audience you might hope to get once you figure things out. There are different personas. You really have to pay attention to what is your customer persona. I agree 100%.
Katharine Woodman-Maynard: Yes. There can be multiple personas.
Sal Daher: Eventually. Yes.
Katharine Woodman-Maynard: It just makes everything else so much easier for your team, but especially from a design and marketing perspective, if they have an idea of this is the person, what would appeal to that type of person? It just makes it a lot less guesswork. It's a lot more focused. That's another bit of advice. My third bit of advice, which Sal, is very familiar with is have a good headshot.
[laughter]
Katharine Woodman-Maynard: Oh my gosh.
Sal Daher: Make sure it's not a tiny 85K-
Katharine Woodman-Maynard: Pulled from LinkedIn.
Sal Daher: -and pulled from LinkedIn portrait, because those things are crumby. It needs to be at least one megabyte. How many times have I said this?
Katharine Woodman-Maynard: Oh my gosh.
Sal Daher: As a matter of fact, I judge founders. If they send me an 85K, I think I said that this person does not execute well.
Katharine Woodman-Maynard: This is something, for the podcast, we have photos of the guests on the website and we use it in various ways. Sal always has a nice description of what he needs. Often we get somebody just pulled it directly from LinkedIn and it's tiny and it looks horrible and it's pixelated. Especially now when iPhones have such good camera functions, you can put it on portrait mode, just go outside and have some neutral backdrop or have trees or whatever. It's really not that hard, but it does make a difference in terms of how you present yourself, how people feel about you. It's a big deal.
I've seen this as a graphic novelist. When The Great Gatsby came out, I had a little press package on my website that had my headshot. It had sample pages from the book, things like that. I got an article in the Star Tribune, our local newspaper here that I-- they never contacted me about it. They just pulled things from that press kit and used it. I'm pretty sure that one of the reasons the article was on me, not only that it's a wonderful book, but also that it was just easy for them to get that, what they needed.
From a marketing perspective, you want to make it easy for people to feature you too. Having a nice image on your website, things like that, I think is just really important.
Sal Daher: Outstanding. This brings to mind my friend, David Kessler, who's an angel investor and he's an engineer, very successful. He has a breathing tube. He's combating cancer here. I asked him, David, send me your headshot. Gosh, you should look up his headshot. He took that himself. He's a very accomplished photographer. It has the breathing tube on it, but it's very honest. It's a very honest picture. It's a very compelling picture. It's a beautifully taken shot. Wasn't that a great headshot? I think it's one of the most memorable headshots we've had.
Katharine Woodman-Maynard: Nice. Yes. That's wonderful. You've done how many interviews at this point, Sal? Almost 300?
Sal Daher: No, it's 260-something.
Katharine Woodman-Maynard: It's very impressive. I've been happy to be part of it. It's been wonderful.
Sal Daher: Seven seasons. It's tremendous. I've learned a lot and I've connected with some incredible people. This is great. Katharine, unless you have some other thoughts, we will wrap it up right now. Look forward to seeing this beautiful webpage with all the right links and everything on this.
Katharine Woodman-Maynard: Yes. I guess I should mention too that I'm very active on Instagram and on Substack. My Substack is called Creating Comics and on Instagram, I'm @WoodmanMaynard, which is my last name, which we'll link to too.
Sal Daher: Oh, I'm going to immediately follow because I have a Substack also, Aging Fit. Creating?
Katharine Woodman-Maynard: Creating Comics.
Sal Daher: Comics. Okay.
Katharine Woodman-Maynard: Yes. Thank you so much for having me. It's been wonderful and it's always a pleasure to work on your show and to speak with you, Sal.
Sal Daher: Well, it's tremendous, Katharine. All the best. All the best to the little listener there shaking its collar. I hope it gets better soon.
Katharine Woodman-Maynard: Yes, us too. The sedatives have helped a lot.
Sal Daher: Poor guy. Thanks a lot. This is Angel Invest Boston. I'm Sal Daher. Thanks for listening.
[music]
Sal Daher: I'm glad you were able to join us. Our engineer is Raul Rosa. Our theme was composed by John McKusick. Our graphic design is by Katharine Woodman-Maynard. Our host is coached by Grace Daher.