My Worst Investment Ever

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A couple months back, I received this message out of the blue from Andrew Stotz, who calls himself the "Worst Podcast Host."

"I'm a fan of The Marketing Mentor Podcast! Great podcast! I wonder if you're willing to join me on my podcast, and share your worst investment story and what you've learned from it. On My Worst Investment Ever podcast, 600 guests have shared their worst investment stories with me to help others learn from those mistakes. I know it's not for everyone but will you be brave enough to share yours?"

Of course I said yes! And here's what came out of it!

The story I shared was from very early in my self employment, when I did not yet know I could (and should) be using my business as a laboratory for my personal growth and therefore had not yet learned to speak up and stand up for myself. 

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Transcript of Marketing Mentor Podcast Episode #466

ilise benun 

One day last year, I got a message out of the blue from a guy named Andrew Stotz. It was a cold email and I get lots of them. He wrote, “I'm a fan of The Marketing Mentor Podcast! Great podcast!

I wonder if you're willing to join me on my podcast, and share your worst investment story and what you've learned from it.

On My Worst Investment Ever podcast, 600 guests have shared their worst investment stories with me to help others learn from those mistakes.

I know it's not for everyone but will you be brave enough to share yours?

I of course said yes. 

The story I shared was from very early in my self employment, when I did not yet know I could (and should) be using my business as a laboratory for my personal growth and therefore had not yet learned to speak up and stand up for myself. 

This is the story of what happened with my own marketing because of it. So listen and learn…

Andrew Stotz 

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 risk, but to win big, you've got to reduce it.

Ladies and gentlemen, I'm on a mission to help one 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 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 guest, ilise benun.

ilise, are you ready to join the mission?

ilise benun 
Indeed I am.

Andrew Stotz 
Let me introduce you to the audience. ilise 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, including the Marketing Mentor podcast, seven books including the “Creative Professionals Guide to Money,“ three online courses for CreativeLive and and much more. ilise, take a minute and tell us about the unique value that you are bringing to this wonderful world.

ilise benun 
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 learn 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
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? Are they going to have 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 the feeling that they got from that was just being able to voice something.

So, wow, 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
Thank you. I really enjoy it, also. 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
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 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

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 at a time, right? We don't want to overwhelm people because then they can't really take anything in.

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

ilise benun 
That is at

Andrew Stotz 
Perfect and I'll have the links 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 it, and then tell us your story.

ilise benun
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 learn 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 once he exited—and there was no bad blood—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.

Andrew Stotz 

ilise benun
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 thousand dollars. 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 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 
Yeah, I'm wondering how you felt when you open up that first, you know … can you remember that feeling?

ilise benun 
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 miscommunicate?”

Andrew Stotz 
Can you remember the time that you first started talking to him? Or you started thinking about how this brochure or 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 
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 

And that's why the “My Worst Investment Ever” podcast is sometimes called “a confessional.”

ilise benun 
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 
And how would you describe … let's just summarize the lessons that you would take away from it.

ilise benun 
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, 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 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.

Andrew Stotz
So maybe I'll just go through a couple of things that I take away, too. One thing that I take away is: I try to deliver products incrementally, 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 more like that.”

Okay. Yup, yup.” And then, so I'm iterating through this kind of incremental disclosure. And it's the way I manage, too, when I have 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 even when you're a 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 thing …

ilise benun
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, 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.

Andrew Stotz
Hmm, yeah, so “collaboration” is a great word.

And I think when you think about almost any work that you're doing, you know … I would say, once you reach a certain level in your business, maybe 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 know, you didn't get what you ordered and it arrived as something different. And maybe you think, “Well, you know, it's close enough or whatever.”

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, “Well, I don't wanna, you know, eh, I don't want to … “

ilise benun 
… Rock the boat …

Andrew Stotz
I have an obligation. I have a fiduciary duty. I have a duty of trust that’s based upon money that I've got to deliver. If I don't deliver through 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 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 
Yeah, I agree. I mean, the idea of advocating for yourself actually is reminding me of my favorite book at the moment, which I happen to have right here. Do you mind if I show you?

Andrew Stotz

ilise benun
It's called “Bring Yourself,” by Mori Taheripour, “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,’ 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 
It's a counterintuitive thing, because if you think about a young person, and you know, also you could say, “You know, I'm young. I mean, look, I'm just a kid. Look at my life … ”

Some people may be hesitant to bring their true self out. But also, you know what people learn in school and all that is the idea of ‘be a professional.’

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 like, that's what we're supposed to be.

And for creatives, 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, bring yourself ... . So that’s interesting. I’ll put the book into the show notes.

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 what you learned from this story, what you continue to learn—what one action would you recommend our listeners take to avoid suffering the same fate?

ilise benun 
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 
Great advice. And that's a challenge, as you say, for people—particularly if you're younger, the person is experienced, maybe they're busy and they're like, “What?”

You know, even if it's a bother, if you bother people with it. 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 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 
Well actually my Domestika 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 Oreo Strategy, which is a way to help people—using a food metaphor—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 Oreo Strategy for Domestika.

Andrew Stotz
Fantastic. Well, we're gonna have a link in the show notes to that so the listeners and the viewers can go and check it out. I like it.

I was just thinking about proposals I've recently given and, even at my age and my experience of giving proposals, I was talking with someone about reframing some of what I was saying, and all of that. And I just like, “Yeah, you just never stop learning.” 

ilise benun 
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 it’s 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 
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, after they signed it, 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.” And I was like, “How could you do that?” And, you know, they're nice, they’re friends, and all that. And so we went through, and I said, “No problem, you know, we'll make this ...”

But it's just evidence of what you said—and 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 that I do everything by Zoom, you know, by video.

I have a questionnaire. I ask a lot of questions when I'm talking to a potential client. And then after that, once I've put some stuff together, I say, “Let's get together again on Zoom and I'm gonna walk you through what my proposal is, the idea.”

And that way, face to face … you know. 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, I 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've written.

ilise benun
That, too.

Andrew Stotz
But I think that making it a creative, you know, nice presentation …

ilise benun
A 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
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 the client was …  so this is for an outsourced CFO service that I do … and basically, there was 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, it's going to cost you half of what it's going to cost to buy a CFO, to 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 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 dollars, 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 an 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?   

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 your goal? What's the outcome here? You guys just messing around? You're doing this business for fun? Or are you trying to deliver value? Are you 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, you just get my creative juices going.

ilise benun 
I like that.

Andrew Stotz 
All right. Last question. What is your number one goal for the next twelve months?

ilise benun 
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 campaigns that I do, and so far, so good. I'm really excited about that.

Andrew Stotz 
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 is 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, curate 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 bringing 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.

ilise benun 
I agree.

Andrew Stotz 
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 right now to claim your spot.

As we conclude, Ilise, 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 
I would just say, the only mistake is making the same mistake more than once.

Andrew Stotz 
Love it. New mistakes! Okay.

ilise benun 

Andrew Stotz 
Love it. And that's a wrap on another great story to help us create, grow and protect our wealth. Fellow risk-takers, let's celebrate that, today, we added one more person to our mission to help one million people reduce risk in their lives. This is your Worst podcast host, Andrew Stotz, saying, “I'll see you on the upside.”

ilise benun 

I hope you can relate to my story. Was there a time you kept quiet, didn’t say what was on your mind - and paid the price? We can all learn from the mistakes of others – so I hope you learn from mine. 

In fact, the baby step I would suggest is to spend a few quiet minutes right now thinking about whether there is a current situation – personal or professional – where you held your tongue and shouldn’t have – (because sometimes that is the best thing – the trick is learning to discern the difference). Or maybe you didn’t ask a question for fear of sounding stupid or revealing your ignorance. If so, see if it’s not too late to correct your mistake and then vow to pay closer attention in the future. 

Things are different now for me – I’ve worked hard to make it so. I now love saying what needs to be said and letting whatever happens happen. It’s so very liberating and really builds confidence. 

So if  you want to build a thriving business on your own terms, the first step is to sign up for my Quick Tips at Once you’re on the site, you’ll find lots more resources, including my Simplest Marketing Plan. Enjoy and I’ll see you next time.

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