Ep635: Ilise Benun – Ask Every Question You Can Think Of

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Quick take

BIO: Ilise Benun has made it her business to teach basic business skills to creative professionals who should have learned them in school but, alas, did not because it’s not taught in school.

STORY: Ilise hired a designer to design a brochure for her consulting practice. Instead, he delivered a folder with her logo.

LEARNING: Stand up for yourself. Ask every question you can think of.


“Ask every stupid question to confirm the details of any arrangement.”

Ilise Benun


Guest profile

Ilise Benun has made it her business to teach basic business skills to creative professionals who should have learned them in school but, alas, did not because it’s not taught in school. This has, for years, perpetuated a “starving artist” mentality amongst creative professionals, who are naturally talented and could easily bring their creativity to the business side of their business if only they knew how. That’s her mission with all of her work through marketing-mentor.com, including The Marketing Mentor Podcast, seven books including The Creative Professional’s Guide to Money, three online courses for Creative Live and Domestika.org, and much more. If you want more from Ilise on mindset, money, and marketing, sign up for her Quick Tips.

Worst investment ever

When Ilise started her business, she came across a graphic designer and thought it would be great to have a brochure for her consulting practice. The designer showed Ilise images and examples of what the brochure would look like. Ilise was very excited. But when the brochure arrived on her doorstep, it was not what she had imagined. The designer designed boxes of folders with Ilise’s logo on it. The designer asked her all sorts of questions, and she answered them. She was utterly disappointed in the product but didn’t say anything. She just never worked with the designer again. Ilise was so young, immature, and afraid at that point in her career that she just didn’t stand up or advocate for herself.

Lessons learned

  • Stand up for yourself and bring yourself to the negotiation.
  • Strip away all of those things you imagine you’re supposed to be so that people can see who you are. That’s who they’re going to want to work with.

Andrew’s takeaways

  • When working with service providers, ensure that they deliver incrementally or get feedback as you go through the process. Don’t wait to get the final product to give your input.
  • Stand up for yourself to deliver to your business partners, employees, and family.

Actionable advice

Ask every question you can think of, even if it feels like it would be a stupid one.

Ilise’s recommendations

Ilise recommends her Domestica course, Writing a Winning Proposal. She teaches what she calls the proposal Oreos strategy. This is a way to help people using a food metaphor to learn how to have the money conversation and then decide whether or not to write a proposal based on that conversation.

No.1 goal for the next 12 months

Ilise’s number one goal for the next 12 months is to expand the E-commerce part of her business, take all the content she’s been creating, and turn it into products she can sell.

Parting words


“The only mistake is making the same mistake more than once.”

Ilise Benun


Read full transcript

Andrew Stotz 00:01
hello fellow risk takers and welcome to my worst investment ever stories of loss to keep you winning in our community. We know that to win in investing, you must take risks but to win big, you've got to reduce it. Ladies and gentlemen, I'm on a mission to help 1 million people reduce risk in their lives. And that mission has led me to create the become a better investor community in the community. You get access to the tools you need to create, grow and protect your wealth. Go to my worst investment ever.com right now to claim your spot. Fellow risk takers this is your worst podcast host Andrew Stotz, from a Stotz Academy, and I'm here with featured guests, Ilise Benun, Ilise are you ready to join the mission?

Ilise Benun 00:44
Indeed I am.

Andrew Stotz 00:47
Let me introduce you to the audience. Elise has made it her business to teach basic business skills to creative professionals who should have learned them in school, but alas, did not because it's not taught in school. This has for years perpetuated a starving artist mentality amongst creative professionals who are naturally talented, and could easily bring their creativity to the business side of their business. If only they knew how. That's the mission, she's on with all of her work through marketing, mentor, marketing, Dash mentor.com, including the marketing mentor podcast, seven books, including the creative professionals guide to money, three online courses for Creative Live and domestica.org. And much more in these take a minute and tell us about the unique value that you are bringing to this wonderful world.

Ilise Benun 01:45
I think because it's true, there are other people who coach, I'm mostly a coach, and I am a content machine. And I create content out of everything that I learned as I'm coaching, but I think I am a good listener, I try to listen really carefully. A lot of people come to coaches and expect them to talk a lot. I don't do a lot of talking, I just listen and then try to give people what they need when they need it. No more, no less.

Andrew Stotz 02:13
And when you listen to people, you know, I'm curious because I did a thing A while ago, where I sent out in my email, I said anybody that wants to book a call with me, I'll do a 15 minute call with the first 10 people I'm going to set up my Saturday afternoon. And I was completely booked out. And I went from one call to another and you know what I was thinking to myself, What am I possibly going to say? You know, and they're going to have a questions and you know, they're facing difficulties. And you know, all that. And it was no problem. All I did was listen. And I heard and half of this half of the feeling that they got from that was just being able to voice something. So while listening really works. Even if you know, sometimes you are listening to respond, is there something I can help in this case, but other times, just listen. So I really admire that in you.

Ilise Benun 03:06
Thank you, I really enjoy it. Although it feels very gratifying to know that you can just be in the moment and be with someone and then maybe give them a little bit of what they need.

Andrew Stotz 03:19
One way that a pro tip on that too, for the listeners is one way to kind of force yourself to listen is to take notes. Because it's very difficult to speak and write at the same time. And so I find that, you know, taking notes, I'm doing that all the time when I'm talking to you when I'm talking to others. So I like what you're saying, now that before we go into the big question of the podcast, maybe you can just tell the audience a little bit more about what's the best way for them to interact with you to get more of what you're doing and what should they get from that. What should they expect to get from that?

Ilise Benun 03:58
Well, as I said, I'm a bit of a content machine. And I'm constantly coming up with ideas for tips and content and new angles and ways of thinking about marketing for creative professionals and new metaphors that might help people understand better what the heck I'm trying to explain. And I do that a lot through my podcast, as you said, but also through my quick tips. I send out an email newsletter every other week, where I feature a video from my YouTube channel and then I just add some ideas to it so that people can get again, a little bit out of at a time, right? We don't want to overwhelm people because then they can't really take anything in.

Andrew Stotz 04:41
It's a good point. And where can people sign up to get on that newsletter?

Ilise Benun 04:45
That is at marketing dash mentor.com or marketing dash mentor tips.com

Andrew Stotz 04:52
Perfect and I'll have the link to that in the show notes. Well now it's time to share your worst investment ever and since no one goes into their worst investment thinking it will be tell us a bit about the circumstances leading up to and then tell us your story.

Ilise Benun 05:05
So, you know, I really actually had a hard time coming up with something, not because I've never made any mistakes or bad investments, it's just that I really feel like I learned from absolutely every single thing I do. And you really don't know, if it's a bad investment immediately, right, like 10 years down the line, you could see oh, that was actually the best thing I ever did, even though it didn't feel that way at the time. And so I tried to think about a situation where I had made a mistake. That's how I thought about it, I had invested whatever time money myself, my fantasies, right my brain into something that I shouldn't have. That's the way I was thinking about it. And I was thinking actually about a business partner that I had for three years. And you could look at that and say, Well, that was a bad investment of three years, because it didn't work out. But actually, he is the one who had the idea for the podcast. He's the one who had the idea for my online store. And I have once he exited, and it was there was no bad blood. We basically I made it my own and built up on what he did, and his ideas. And now it's been like the cornerstone of my business. So I thought about that as a possible bad investment. But it really wasn't because that was indeed the best thing I ever did. But I did think of one thing, okay. And that is early on in my business, and I've been in business for almost 35 years now. So early on, I would say in the first 10 years, I came across a graphic designer, and I thought I needed a brochure for my consulting practice. And so we went through a whole process where he asked me all sorts of questions, and I answered them, and he showed me images and comps and examples of what it was going to look like. And I was very excited. And then when it arrived on my doorstep, it was not at all what I had imagined. I thought I needed a brochure, he basically designed folders, boxes and boxes of folders with my logo on it. And I can't remember how much I spent it was a couple $1,000 It wasn't a lot of money. But the investment that was the mistake to me was the communication or the lack of communication, if you will, plus the fact that I never said anything about it. I never said hey, wait a minute. That's not what I thought I was getting, or that's not what you said you were going to do. For me. It was just a total like mismatch and miscommunication. And I was so young and immature and afraid at that point in my career, that I just did not stand up for myself or advocate for myself, or do anything. So to me the investment was not the money or the time it was like the lack of me invested in that, if that makes sense.

Andrew Stotz 08:21
Yeah, I'm wondering how you felt when you open up that first, you know, can you remember that feeling?

Ilise Benun 08:27
I do. I was like, What the heck is this? This is not what I asked for. This is not what I paid for. And I don't even think I knew at that point that it was a miscommunication. I was just disappointed. And like, All right, well, I'm never working with him again. Right? It was like totally writing off the whole thing as opposed to I don't know, perhaps the more adult thing would have been to say, have a conversation about it and say, where did we miss communicate?

Andrew Stotz 08:56
Can you remember the time that you first started talking to him? Or you started thinking about how this brochure or you know, this introduction to you and your business was going to impact your business? Like, did you obviously we go into these things thinking it's going to be impactful? And there's excitement in that?

Ilise Benun 09:18
Yeah. And actually, you know, it's a little meta because as a marketer, you have to have marketing materials, and to have made a mistake about my own marketing materials is kind of embarrassing, right.

Andrew Stotz 09:32
And that's why the My worst investment ever podcast is sometimes called a confessional.

Ilise Benun 09:40
Yes, definitely. I mean, I think I totally blocked it out. I didn't even think about it after that. I just put it behind me. And then it was really just your question and your outreach to me that brought it back to my memory, you know, oh, so long ago, so I don't know. It's been kind of fun. Just thinking about it and thinking about the lessons,

Andrew Stotz 10:02
and how would you describe, let's just summarize the lessons that you would take away from me.

Ilise Benun 10:08
And actually, I think there's one other thought I had that is probably an answer to the question you just asked, because I do remember, like, he asked me all these questions, and I thought my answers to the questions would be in the brochure. And what I've since learned is that often designers ask all sorts of questions, just to get a good not to get a good feeling, I don't mean to make fun of it, but like, for their brand experience, right to know what the visual is going to be like, and, and, and how they're going to be creative, like adding to the creativity, but I was very literal. And I thought those things I said, that's supposed to be in the brochure. Right. And so that was the other thing, like opening the box and seeing the folders. Like, where's everything I said, Where's me, basically? So

Andrew Stotz 11:00
I, maybe I'll just go through a couple of things that I take away if that's the one thing that I take aways, Inc. I try to deliver products incrementally. And meaning that okay, okay, I think I understand what you want. Give me a week, and I'll come back to you with some thoughts. And then I deliver kind of a framework, and then they go, no, no, no, I want it, the more like that. Okay. Yeah, yeah. And then, so I'm iterating through this kind of incremental disclosure. So that and I always, it's the way I manage to when I have, you know, particularly new staff or interns or others, I'm like, Look, just do that. And then they come back with that, and I go, No, yep. Oops, not that, you know, because it's even when you're good communicator, it's hard to communicate, really what you're thinking. And so my first lesson that I take away is, you know, maybe delivering in an incremental way, or getting sign off or feedback as you're going through the process. The second

Ilise Benun 12:00
thing, let me add something to that, because what you're describing to my mind is more of a collaboration. And a lot of times creatives, especially they want to like take the project, go away, right? Do the work, and then come back and go, tada, what do you think? And then they're waiting also for the applause. And that is not at all what a collaboration is about? Hmm,

Andrew Stotz 12:24
yeah, so collaboration is a great word. And I think when you think about almost any work that you're doing, you know, there, I would say, once you reach a certain level in your business, maybe you know, you can get enough of a guideline. To go back, I remember a guy that did most of the designs that related to my business, everything he delivered was pretty spot on. I mean, I was impressed. And so, you know, once you get really experienced at that, you know, maybe you don't need to do it as incrementally, but I take that away, I think the other thing is stand up for yourself. And this is hard. And I think it's a good lesson, to listen to what you went through. Because what it can help is young people right now, who you get, you know, you didn't get what you ordered. And it arrived at something different. And maybe you think, Well, you know, it's close enough or whatever, you know, the way I always look at it is look, I have an obligation to my business partners, to my employees, to my family that I get, I don't waste money, and I get the best that I can for what we're doing. So sometimes I use that as a tool to step beyond the feeling like wow, I don't want to you know, I don't want to Oh, you know, yeah, you know, no, no, no, I have an obligation, I have a fiduciary duty, you know, I have a duty of trust, it's based upon money that I've got to deliver, if I don't deliver to my business, to my family, to my employees, to my business partners, what am I doing? So I use that as a tool to get a little bit to get a little bit more of a backbone to stand up for myself. And so that's kind of one of the things that I also take away and I think that the listeners can take away.

Ilise Benun 14:13
Yeah, I agree. I mean, the idea of advocating for yourself actually reminding me of my favorite book at the moment, which I happen to have right here. Do you mind if I show you please? It's called Bring yourself by Morita Hara poor how to harness the power of connection to negotiate fearlessly. I just had her on my podcast, actually, this week. And it's just, it's all about standing up for yourself and bringing yourself to the negotiation because often people imagine in all of these situations that they have to be someone else that the professional is someone different from them. And it's a constant struggle to try to bring, you know, what you called my unique value in this world. All right, to the work, to the conversations to the collaboration. And that's often one of the things I'm working with people on is how do we strip away all of those things you imagine you're supposed to be so that people can see who you really are, because that's who they're going to want to work with.

Andrew Stotz 15:18
That's such a, it's a counterintuitive thing. Because if you think about a young person, and you know, I mean, also, you could say, you know, I'm young, I mean, look, I'm just a kid. I mean, you've looked at my life, you know, you may think, you know, so some people may be hesitant to bring their true self out. But also, you know, what, what people learn in school, and all that is the idea of like, you know, be a professional as there was a comedy skit on Saturday night live many years ago called giant businessman, and my friend, and I used to always joke, hey, giant businessman, you know, and he had his briefcase, and you know, and like, that's what we're supposed to be. And for creative, that's very different from the way that you're thinking the way that you're running your life and all that and, you know, be bring yourself so that's an interesting, I'll put that the book in the show notes. Also a link to that is, yeah. So based upon what you learned from this story, and imagine, let's say, a young person out there, that's in a similar situation. And you know, what you learned from this story, what you continue learning what what action would you recommend our listeners take to avoid suffering the same fate?

Ilise Benun 16:24
Well, I want to say, ask every stupid question to confirm the details of any arrangement. But that is not an easy thing to do. Because you have to interrupt a mental process, a mental habit that most of us have, which is to kind of override the things that we think so you have to think something? And then you have to say, no, that doesn't make any sense. I've got to do something different. And maybe that different thing would be going beyond my comfort zone and asking a question like, Wait, let's just make sure we're on the same page here. Right. And often people think that these are stupid questions that they should know certain things already, without learning them without asking the questions. And so, you know, I guess the simple way to say it is just ask every question you can think of, even if it feels like it would be a stupid one.

Andrew Stotz 17:22
Great advice. And that's a challenge, as you say, for, for people, particularly if you're younger, the person is experienced, maybe they're busy, and they're like, Well, you know, even if it's a bother if you bother people with the look, ask the question. So that's great advice. So let me ask you, what's the resource that you'd recommend already, you've read, you've recommended one resource, which is the book you just mentioned, but any others of yours or any other resources that you'd recommend for us?

Ilise Benun 17:48
Well, actually, my domestica course, which is relatively new is wonderful, in my opinion, and it's called Writing a winning proposal. And in it, I teach what I call the proposal Oreos strategy, which is a way to help people using a food metaphor, right to help people learn how to have the money conversation, and then decide whether or not to write a proposal based on that conversation, because A similar thing happens. Someone says, I've got a project for you. And the creative professionals say, Oh, my God, they want me, I'll do anything for it. Right, as opposed to well, let's see if it's a good fit. Let's see if you can afford me. Let's see if we're going to communicate well together. So I try to pack all of that into my proposal Oreos strategy for domestica.

Andrew Stotz 18:40
Fantastic. Well, we're gonna have a link in the show notes to that. So you can for the listeners and the viewers, they can go and check it out. I'd like it. I was just thinking about proposals I've recently given and even even at my age, in my experience of giving proposals, I was like, talking with someone about reframing some of what I was saying and all of that, and I just like, yeah, you just never stopped learning. So that's

Ilise Benun 19:04
and can I just give a little tip about that, that I've noticed, because I've been doing proposals and reviewing people's proposals for years, too. But lately, I noticed that nobody reads all that much anymore. So if you send a proposal with a lot of words, it's likely they're not going to read the whole thing. So one of the things I recommend is having a lot of visuals, number one, designing it so that easy to read, and literally walking people through it in real time, so that you can answer questions and anticipate objections and ask the question, when are you making a decision? Because one of the things that happens so often is that people get ghosted because they say, Oh, you want a proposal? Here it is, and then they don't have the money conversation. They don't have a conversation, any conversation with the prospect and then they never hear from them again.

Andrew Stotz 19:55
Such great advice there and I think you know, I even had a client recently, and they signed this contract. And then at the end of the signed it, you know, the week later, we came back together two weeks later to work on something. And they said, well, we want to change something in the contract. And I said, But you already signed the contract. Yeah, but we didn't actually read it. They didn't say that. But I know that they didn't read it. And so they asked me, could you modify this, you know, a couple of terms in here, you know, and I was like, How can you do that? And I, you know, they're nicer friends, and all that. And so we went through, and we said, I said, No problem, you know, we'll make this but it's just evidence of what you said, if people aren't reading contracts, they may not be reading proposals, either. So it also made me think of another idea. And I do it a lot is it I, I, I do everything by zoom, you know, by video. Alright, let's, you know, and I have a questionnaire, I asked a lot of questions when I'm talking to a potential client. And then after that, once I've put some stuff together, I said, Let's get together again on Zoom, and I'm gonna walk you through what my proposal are, and the idea. And that way you face to face you know, you've got to have I mean, I would like to do it in person, but I can't always do that, given the location. But yeah, you really made me and I think for the listeners out there, really think about the fact that people are not reading what you're putting together. So either number one, I thought the answer that you were gonna give was, make bullet points of, you know, what you, you know, what you've read, too. But I think that making it a creative, you know, you know, nice presentation, or some

Ilise Benun 21:37
slide show some visuals, some images, their logo, right to show that it's not a generic proposal, it's something you did for them for their needs. So let me tell you how I'm going to solve your problem.

Andrew Stotz 21:52
The other thing is, there's a lot of things that you've sparked in my mind. One of the things that I realized was kind of missing from one of my proposals is that I was the client was I sent so this is for an outsourced CFO service that I do. And basically, I said, Look, we can fix, there is no question that we can fix their accounting, their finance, I think they don't have any question about that. And I told him Look, and it's going to cost you half of what it's going to cost to buy a CEO, CFO, get a CFO in there and try to fix it, and you're not even sure they're gonna be able to do it. Well, then they started looking at the hours and saying, Well, yeah, but I'm paying a CFO this and started and then I just thought, I just dragged it into this place, I don't want to be. And then I started to think, you know, if your company has a value of $100 million, and I can help fix the accounting and finance, that can allow you to increase the value of your company from $100 million to $110 million, which I know when accounting system is messed up, and the management team doesn't have the right numbers, getting the right numbers, and helping them make the right decisions will definitely at least get it from 100 to 110. How much is that 10 million worth to you? Right? You wouldn't hesitate to pay me a million to bring you that 10 million. And so what I needed to do, and I realize it and now talking to you more is also focused on what's what's your goal, right? What's the outcome here? You guys just messing around? You're doing this business for fun? Are you trying to deliver value trying to exit? Are you trying to make sure you exit at a price that's going to bring you what you need for your family, your employees and everybody? Or are you just messing around? And so it just, you just get my creative juices going? I like that. All right. Last question. What is your number one goal for the next 12 months?

Ilise Benun 23:42
Yeah, I'm focused on expanding the E commerce part of my business and taking all the content that I keep creating, and really turning it into products that I can sell. And one of them is called the simplest marketing plan, which is something I improve and simplify and distill every year. So I just launched the simplest marketing plan for 2023. And then I'm just going to build on that I've hired a digital marketer to help me improve the campaign's that I do, and so far, so good. So I'm really excited about that.

Andrew Stotz 24:17
That's very exciting. And I know it can go very far, particularly, as you said, you know, you're like a content machine. If you're a content machine. You know, one of the problems that we face I know for myself is that we spew out a lot of content, but we're not we're not monetizing that oftentimes. And we think, well, it's no problem. It's going to bring in a lot of people looking at it and all that. But hey, once you've put out a lot of good content, there's value in that. And in fact, isn't it funny when the internet first came along? It's like I can get everything for free. I can get all the news I want for free. So how has anybody ever going to survive and now you're all of a sudden you realize that actually what's valuable now is not free. It's curated. You know, you could take every bit of content that you've done Write it down to a small list in different groupings and stuff. And it's all free out on the internet, but by curating it and bring it into a course format that helps me transform my business myself. There's total value in that. And I think that's what people want these days. I agree. Exciting. All right. Well, listeners, there you have it another story of loss to keep you winning. If you haven't yet joined the become a better investor community, just go to my worst investment ever.com right now to claim your spot. As we conclude this, I want to thank you again for joining our mission and on behalf of a Stotz Academy, I hereby award you alumni status for turning your worst investment ever into your best teaching moment. Do you have any parting words for the audience?

Ilise Benun 25:43
I would just say the only mistake is making the same mistake more than once.

Love it. New mistakes. Okay. Awesome. Love it.

Andrew Stotz 25:57
And that's a wrap on another great story to help us create, grow and protect our well fellow risk takers. Let's celebrate it today. We added one more person to our mission to help 1 million people reduce risk in their lives. This is your words podcast host Andrew Stotz saying, I'll see you on the upside.


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About the show & host, Andrew Stotz

Welcome to My Worst Investment Ever podcast hosted by Your Worst Podcast Host, Andrew Stotz, where you will hear stories of loss to keep you winning. In our community, we know that to win in investing you must take the risk, but to win big, you’ve got to reduce it.

Your Worst Podcast Host, Andrew Stotz, Ph.D., CFA, is also the CEO of A. Stotz Investment Research and A. Stotz Academy, which helps people create, grow, measure, and protect their wealth.

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