Mistake-Proof Your Small Business, with William Holsten

Ever notice how a new boss “fixes” a process that wasn’t broken—and six months later everyone is quietly doing it the old way again? That loop is costly for small businesses, and we sought a more effective approach. William Holsten, a business mistake prevention specialist, author, and former brand leader, will unpack why errors repeat and how to prevent them with simple, durable habits.

Holsten starts with the real first step after a leadership change: get out of the office and into your customers’ world. He lays out a practical script for face-to-face conversations that actually get the truth, plus ways to map the entire customer journey in a photo retail context—from file transfer and on-site kiosks to packaging, archival storage, and digital asset handling. From there, he breaks down his $10,000 mistake checklist: “no one actually needs this,” “death by assumption,” the “vanishing wallet” cash-flow squeeze, and “flying without a map.” Each comes with field-ready fixes: test-and-learn prototypes, quick price sensitivity checks, weekly cash forecasts with tripwires, and a one-page plan that nails proposition, differentiation, and unit economics.

Holsten also shares the origin and rebuild of PitchBurst, a dunk-tank alternative that delighted early users but failed on materials—until a full engineering rethink made it bulletproof. The lesson translates to imaging: validate not just demand but durability and workflow under real conditions. We explore using AI to cut through analysis paralysis, the value of mentors, experts, and naive observers, and a favorite tool he calls “uh-ohology”—learning from other people’s mistakes so you don’t pay the tuition yourself. Expect actionable tactics like pre-mortems, design thinking sprints, and daily “parachute checks” for backups, insurance, and lab mainte

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Chapters

• 0:00 Welcome & Sponsor Shoutouts
• 0:20 Meet William Holsten
• 1:45 Corporate Path: Ads to Brand Innovation
• 3:25 Kodak, Bayer, and Industry Crossovers
• 4:40 Why Businesses Repeat Mistakes
• 6:15 New Leaders, Old Patterns
• 7:50 First Step: Immerse in Customers
• 9:25 Asking Better Customer Questions
• 12:00 Passion vs. Business Skills
• 13:15 The $10,000 Mistake Checklist
• 16:20 Assumptions, Cash Flow, and Plans
• 18:05 Flying Without a Map
• 19:20 What SCORE Mentoring Offers
• 22:10 Analysis Paralysis and AI
• 24:10 Mentors, Experts, and Naive Eyes
• 25:30 The PitchBurst Origin Story

Transcript

Erin Manning: 0:02

Welcome to the Dark Pixels Society Podcast, the Photo Imaging Industry's leading news source. The Dead Pixels Society Podcast is brought to you by Mediaclip, Advertek Printing, and Independent Photo Imagers.

Gary Pageau: 0:17

Hello, and welcome to the Dead Pixels Society Podcast. I'm your host, Gary Pageau. Today we're joined by William Holsten, who is a Business Mistake Prevention Specialist, Author and Mentor. And William's coming to us from Delaware. Hello, William. How are you

Wiliam Holsten: 0:34

Hey Gary, happy to see you. Thanks for having me on

Gary Pageau: 0:37

Before we record it started, we were just chatting and we went down a few industry rat holes. Um, you're not from the industry, but you have a lot of experience with mistakes. How did your corporate career start before you got into being an author and consultant?

Wiliam Holsten: 0:53

I was interested in college, in advertising and communications, got my degree in communications, and was hired at an advertising agency on Long Island. And uh I was an ad writer and I did some account work, and that business was closing, and I networked to find the next job. And it was as a a writer in the advertising department of Sterling Drug in New York. Right. And uh there I was writing packaging copy and ads for the global business of bare aspirin and Phillips, Milk and Magnesia, and a whole bunch of things like that. Uh so that that's how I got into the corporate world. Lots of things evolved in the 30. I was they were there 35, 37 years through acquisitions and mergers and lots of things. It led me to become uh a marketing brand manager on Sterling's major brands, Bayer aspirin and things. And then Bayer, the German company, bought Sterling, and I continued on in brand management and later in innovation. So it's a it's a weaving story. I didn't have to look for jobs, but the jobs came to me because of my skill set. At that time, uh, Gary, I know your audience is really interested in photography. As you all know, Kodak bought Sterling Drug before Bayer did. And actually, Bayer was a later acquirer of the same assets of the business. And we talked before the recording, it's a long, long, long story that's very interesting for another time.

Gary Pageau: 2:26

Yeah, that's for sure. Yeah, the whole uh Eastman Kodak buying Sterling Drug, patent portfolio, and uh all those kind of things, a whole nother story, which is uh maybe we'll do a uh an after show sometime or something like that. So let's talk a little bit about you know, your long career business. You know, when I talk to people who've been in corporate America for a long time, I always like to say they've seen some things, right? They've kind of seen things that happen that that's repetitive behavior that happens over and over again. You know, mistakes and why is it then that people repeat mistakes that happen in business so often?

Wiliam Holsten: 3:07

Well, this applies to small businesses. Oh, absolutely. I know my focus is on small businesses, but thinking back in the corporate world, yeah, mistakes continue to happen because of many factors. One of them is senior leadership turnover. The next generation of leaders is hired, comes in, and they say, Oh, the way it was done in the past was wrong, we'll change this. And the long-term people, I was always one of those, can say, Well, been down this road before, but I'll give it my best, and the result is often the same. These have to do with understanding customer preferences, uh, understanding supply chain things, understanding competitive reactions. Uh, there are patterns to observe and learn from.

Gary Pageau: 3:53

So, yeah, we want to tell most about small business because that's my my audience primarily, but I think what happens is, you know, a lot of the practices in big business, big mistakes, are also can be done by small business, right? Same sort of thing, especially when you run into things like the mindset of, well, we've either always done it this way, so we're not going to make changes, or on the other thing was, like you said, there's a management change or an ownership change in a business, and they think, well, we want to judge the entire process and invent new things. So let's take an example of someone who let's say there is a management change within a business. What would be the things they should first look at when maybe they want to improve things but not make wholesale changes?

Wiliam Holsten: 4:39

My first thought on that is to uh immerse in the customer experience. Many times, especially small businesses don't have a big market research department.

Gary Pageau: 4:51

Right.

Wiliam Holsten: 4:52

And they might make assumptions on what customers think, what their experience is, how they in your in the case of photography, how they buy, where they buy, what their experience expectations are. If you're new to a business and you haven't gone and met 10, 20 customers face to face, right, and have a just a QA. How's it going? What do you love? What do you wish for? You're kind of blinding yourself to the possibilities. This is true for somebody starting a business, some for somebody taking over a business.

Gary Pageau: 5:25

So when you're looking at things like what the customer is telling you, right? Let's say, for example, I'm taking over a photo store and I'm buying it from existing manager and I want to meet some of the regular users. What are some typical questions I would want to ask when I'm not just looking for positive feedback, right? I'm not because because typically speaking, when people do face-to-face research, the people who are being interviewed really want to please the people. So they maybe not be accurate or they lie if well because they want to they want to be nice.

Wiliam Holsten: 6:00

Questions can include, now you won't hurt my feelings. I want blunt responses. So you you set that up, but then you ask, you can ask what's wrong, and they may not go down that path, but you can ask what do you wish for? Okay. Uh in the last time, 10 times you came in this store, uh, you experienced this, this, and this. Do you what would make that experience 10% better if we did what you know uh for for you personally?

Gary Pageau: 6:27

Right.

Wiliam Holsten: 6:28

And then there's a matter of uh uh asking the customer, what kind of business are you in? Why do you come and buy here? Right. Can I come to your home or your lab or your shop and see how you use these products? Where are they stored? How do you open them? How do you discard of use if it's film canisters? How do you control the digital assets that you create with what you buy here? Understanding the entire journey really informs you to think how best to serve that journey, and then there's always opportunities to improve and give them something they didn't ask for because you understand the context.

Gary Pageau: 7:09

Yeah, that is one of the challenges I think when people get into business, where they either are self-involved, they get into it because they like whatever it is, right? They like coffee so they open up a coffee shop, they like drinking beer so they open up a brewery, they like photography so they open up a photo store. Well, actually, I have one of my friends in the industry who said to me once, nothing kills your love of photography faster than owning a camera store. No, you get down to the the middle growth. Yeah, because there are different skills other than the passion in the business, right? It it's I mean, generally that's important, but there's certain skills and things you need to have to make the businesses thrive. Um, when you talk about mistakes people make, you mentioned not knowing the customers. What are some other mistakes that people make in their business? Maybe after they've had it for a while, and they tend to just be either complacent or they become just kind of burnt out.

Wiliam Holsten: 8:08

There's a whole list, and these are generic to many small businesses. I've seen some in my in my mentoring as a score mentor, uh, but I've compiled a list and I'll I'll offer to your listeners at the end of this. Uh, I call it the $10,000 mistake checklist. It's a list of the the top eight things that continue to happen here and there uh across businesses. Number one is the no one actually needs this syndrome. This is where people uh get immersed and impassioned about an idea for a product, a service that they love so much and they want to put it out there. And they get it out there if they don't do appropriate research and find out nobody wants this. They're the only ones that love it. And an answer for that is to do some early test and learn. So you talk about it, you describe it, and you listen to feedback so you can build and shape it to something people do like. Another common mistake is death by assumption. It's along the same lines that uh you get out there and you assumed that people would pay the extra 10% for a particular item, or they would travel an extra two miles to get this where a competitor down the road has it as well. Um, if you make assumptions and don't validate them, uh you can be going down a path uh to hurt your business. Another, and this is very common to many businesses that don't have a solid business plan, it's I call it the vanishing wallet trap. And that's where your cash flow dries up before you're ready to have enough revenue and margins to sustain the business. So suddenly you're three months into a new business and and you're at, and the answer on that one is of course to do a better business plan with cash flow um detailed assumptions and adjust if things are after a month or two areas.

Gary Pageau: 10:03

Right, because then because then they may wait too long. Yeah, that's right. You know, at this point in three months they should be here and they're there, yeah, and they don't know how to get from here to there.

Wiliam Holsten: 10:16

What one more? I have a title for it. What's the title? Uh, I call it flying without a map.

Gary Pageau: 10:22

Right.

Wiliam Holsten: 10:22

But lots and lots of entrepreneurs I've seen in my score mentoring don't have a business plan. They know what they want to do and they go ahead and do it, and they're trying it as they they're building as they fly. And my advice is always get a very basic build business plan. And what is your proposition? How do you differentiate? What is the business model? What do the financials look like? You can do all these exercises on paper with even using the Chat GPT to do some research for you. And then you can look at it in black and white. Does that make sense?

Gary Pageau: 10:53

Right.

Wiliam Holsten: 10:53

And if it doesn't, you can adjust it before you spend a penny.

Gary Pageau: 10:57

So, for the people who may not be aware, what is SCORE mentoring?

Wiliam Holsten: 11:01

Thank you for asking. SCORE is a national organization, it's a business affiliate of the Federal Small Business Administration. Uh, it's a network of 10,000 volunteers like me that are available to small businesses to mentor them. Typically, it's on startup, or if it's on you're at the idea phase and you want to prepare a business plan, or if you're a small business and you've got challenges, you can ask a mentor, how might I get out of this? There's a website or something people can go to to. Yes, it's score sco-re-dorg. And if you go on to it, you can learn all about the organization. But what to look for is the place called Find a Mentor. Okay, you will put in a little bit about you and then they will assign you somebody. We as score mentors are all free services, and we've got a library of webinars we can send you, uh resources and templates. But a lot of us, I'm one, I've got my long-term business experience in a corporation and I've run my own aside gig. We're gonna give you our best opinions.

Gary Pageau: 12:05

Right.

Wiliam Holsten: 12:06

Cool. That sounds well. I don't want to deviate into the scorecast. I just want to give you a note. It's probably helpful if somebody is saying, gee, I feel all alone here. How am I going to get somebody to talk to about this? I'm certain that in our 10,000 volunteers, some have run photography-related businesses and would be more familiar than I am.

Gary Pageau: 12:26

So getting back to your items that you were listening before about ways people can run their business, it seems to me like one of the common factors of those was a lack of information, right? Information that is, you know, they didn't under, you know, didn't understand the market or they didn't understand something that was happening. But what about the other way where people have too much information and they can't act on an almost analysis by paralysis? Do you see that happen? Yes, and I've been guilty of that myself.

Wiliam Holsten: 12:57

Uh trying trying to try to get things done, and I'm not ready to pull the trigger yet because I need to know that much more. And you slow down, and opportunities pass you by because you you can't really uh act in a timely fashion to capitalize on a market opportunity. I have found personally ChatGPT and some of the AI things, Google searches help, but you can say in a free Chat GPT conversation, I've got these 15 things and I'm trying to accomplish this. What are the one or two things I should pay attention to first? And it's brilliant. Watch out for mistakes because it's not perfect, but it can be like a silent partner is going to distill things for you and suggest which one or two to pay attention to first and why. And another strength there is you can go back and say, I don't understand what you meant by number two. Help me understand why that's important. And you're not spending a dime and you're getting good pseudo-consulting advice. Again, it's up to you to decide is it's smart or not. Or uh one of the tools in the book that I'll describe in a bit is uh ask mentors, experts, or naive observers. Right. Um, you can be out there, and uh, when I was in my side gig business, which I'll describe for you as well, I felt all alone. Things were not going well, and I didn't know where to turn. I wish I was smart enough to call a score mentor or to reach out to somebody who knew my business that I could say, hey, can I pick your brain for a sec?

Gary Pageau: 14:30

Right.

Wiliam Holsten: 14:31

So, what was the side gig? You can't jump it out there and not say where it is. I know it has nothing to do with photography except we'd use cameras to take pictures of what we did wrong. While I was still with my big corporation, uh my family asked me to rent a dunk tank for a make-a-wish foundation carnival in the hot summer of I think it was 1999. And we rented one and we're preparing to go to help my sister and her daughter make money for the charity. And two weeks before, uh, the rental company called me and said, Listen, there's a drought. We're not allowed to rent you something that's gonna take 500 gallons to fill. So uh, do you want to toss across or some other game? And I said, No, no, it's gonna be hot, I want water, I'll figure this out. My wife and I sat down at our kitchen table and we sketched out, we asked ourselves questions. We said, How do we create something, fabricate something that will deliver the water experience and the surprise without involving 500 gallons? And what we evolved became a game called, now called Pitch Burst. It was a uh 8x10 fiber of wood board with a bar across, and on the end was a basketball uh basket with a water balloon in it. So somebody would throw the ball, hit the target, and a pivot would go and pop the balloon over the head of somebody so water fell down on them instead of them falling into it. We did it for this 95-degree very humid day in August of 1999, and it was a fantastic hit. They made 500 bucks, and we went home and said, Boy, that is smart, that is fun. I could make that a business. And then people called and said, Where can I get that? So we went down the path of getting a patent and with the patent in hand, going to a bank, getting an SBA loan of almost $100,000 that would finance marketing to the rental company business and the fabrication of our first hundred units. We adjusted the design of it just a little bit because ours was so successful, and they were made of wood uh with cheap parts. And uh it went into the rental market uh in the next winter, and we sold about 60 of them. But when the weather got warmer and people began to rent them out to their rental customers, the first calls were the way they loved it. Then the next calls were, oh, the screws came off, the wooden parts broke, the adhesive logo panel is peeling off, it looks like crap, I want my money back, or I want you to fix this. So we sold 60 of these wooden units in about three weeks of the warm weather season. We uh we used the word uh-oh, or there's worse words to say, yeah. We realized we were in trouble because this is not sustainable. We knew the experience was wonderful, but the the material choices we made were bad. We made all the extra parts and did all the things and made refunds where necessary. Uh, we had spent all the money from our loan. We stopped selling, we took back and decomposed the last 40 units, and then we spent two years with more borrowing uh to have an engineer redesign a force out of steel. And that's the fabrication learning we had that product pitchburst is still on sale today. We sold the patents a while ago, but it's it's the one that became the bulletproof crowd D-lighter. So our lessons from that are we did a test market at that carnival, so we knew the proposition was popular, but we didn't do the materials testing. We we did visit a couple of rental stores to say, what do you got? And how would you use this? And we only listened to what we wanted to hear. Oh, we like that, we would buy it. And I asked them, what happens if it breaks? They said, if something breaks in a rental store, we fix it. I said, good. Uh and I never thought about it again. That wasn't true for the other 999% of buyers. When they paid me a thousand bucks, they want it to work, and they get mad when it doesn't. I don't blame them. No. So that business, we we had that game and and several others over 10, 12 years when we owned it and ran it. We learned to understand the customers. We learned to talk, and the customers were the middleman, the rental companies. So we wanted needed to understand their environment, right? How they handle and treat these things, and what it takes to succeed there. We had the pricing down, we had everything else. Just for us, it was material fit for purpose to make it. That was my side gig while I was running uh brands full-time.

Gary Pageau: 19:03

Well, it sounds like that was actually quite useful. Were you able to translate any of your experience from the corporate gig over to the side gig, or vice versa? Were you able to bring anything from the side hustle into your corporate gig?

Wiliam Holsten: 19:18

Yes, yes, yes is the answer all three times. I gave some thought. Uh the book later is a translation of much of that. From the corporate world to the side gig, of course, I had my MBA in marketing, so I was able to brand things well, tell the story well, get things priced correctly. I even know the the basics of the market research we should have done, but didn't.

Gary Pageau: 19:40

Right.

Wiliam Holsten: 19:40

From the side gig side, yes, a lot of times in a corporate world, you there are rules and regulations. They want you to be creative, but you're constrained a lot by the corporate processes and approval levels. I've said that if I used the engineering skills and quality control skills I used in my game business, my drug company, um, people would have died. It would have been terrible. By the way, that never happened. There, there are there are lots of people to protect us from making mistakes. But I also said if I had the corporate structure and approval processes and things in place in my small company, my side gate, we would have never got the first product felt the gown because of all the all the red tape and things. So it it's a both and it was an enriching experience, sometimes uncomfortable to be involved in, right? Uh, but but I learned a ton of things. That actually directly led to me writing this book. I worked for the company for the next after that 20 years or so, and I retired two, three years ago. I finally got to sit down and think what were the lessons learned and how might this help other people? And it led to the creation of the book, and I'll name it now. It's called Uh oh, How to Avoid Unintentional Blunders That Derail Entrepreneurial Success and Goof Proof Your Business.

Gary Pageau: 21:02

Okay.

Wiliam Holsten: 21:03

And it's designed for small businesses and startups and entrepreneurs who are going down the road I did. It includes, of course, the story about the dunk tank and all the kinds of things that we went through, but the important part are the 10 tools in the second half of the book, the how not to uh things. I applied uh in my day job for the final 10, 12 years of my big corporate life, I was leading creative workshops for problem solving and new product idea generation for consumer healthcare products. And we used tools that included design thinking, included pre-mortems, a whole lot of other tools and creative problem solving skill sets. I've translated those into the 10 tools in that book that people, when they if they pick it up or they look at me online, they can see these are things that can help me avoid problems. Okay. Once the book was done, that's when I became the business mistake prevention specialist because I didn't stop my research there. I've been digging and digging to understand it's an art and a science, what's behind slips and mistakes and things you forget. And I boiled it down in the book to uh it's really simple. How you avoid mistakes is to be think smartly and be more aware. It's as simple as that. But that's not simple at all. Right. When you're running your business, it's like you're draining the swamp with a million alligators around, you're too worried about your competitors, your customers, your cash flow, your business, all these things, and you're not thinking, how do I avoid a mistake? Because that's part of the day-to-day. Now, making mistakes is an excellent way to learn. And sometimes you're paying your dues when you're new to a business. Right. You're gonna learn from them anyway. My teaching is about, yeah, some of that is necessary, and you're gonna not know how to avoid everything, but some of the bigger ones, not having a business plan, not really understanding cost experience. Many of those things they are preventable if you just use your capital.

Gary Pageau: 23:06

Right. So what are some of the signs someone would have that something is a serious mistake versus just a temporary hiccup? Because what I see happen a lot is people tend to overlook a major problem uh until it's too late.

Wiliam Holsten: 23:28

It's true that you may not know something is a major threat until it's too late. It's because things cascade and and compound. Uh, you don't know that because you forgot to lock your door when you were closing up on a Saturday night, right? That there could be a risk of threat, fire, somebody getting into it that you don't want to, or uh the cash flow uh before.

Gary Pageau: 23:53

And that's a very typical thing, right?

Wiliam Holsten: 23:54

You you don't know that you oh oh oh crap, I'm out of money. We have to close, I don't know what to do.

Gary Pageau: 24:01

Right.

Wiliam Holsten: 24:01

Part of it, one of my tools that I actually, it's one of my favorites, I call it uh-ohology. It's learning from other people's mistakes. Okay. Uh, it was Warren Buffett, he's quoted often as saying, it's great to learn from mistakes, it's better to learn from other people's mistakes. Right. I look the book has several examples of other people's mistakes and learning from them. The most dramatic one was a skydiver in Pennsylvania years ago, who was asked to film uh another couple, a student and an instructor, as they were jumping and opening their parachutes. So this guy, Ivan McGuire, uh, this is the years before GoPro and even digital cameras, he got uh film camera and scratched it to himself. Yeah, and they were all up at 10,000 feet. He uh they they were they got the okay from the pilots, ready to go, thumbs up. He jumps out, turns on the camera, points it up, gives them a thumbs up, they jump, they pull their ripcords, parachutes open. It was a beautiful, beautiful shot. Then Ivan went for his own ripcord and only at that moment realized that he had forgotten his parachute. It was about the same weight as the parachute, and he got so mixed up with getting it technically rated that he forgot it. He was an experienced guy. How this happened, who knows? He did fall to his death. It's tragic. Oh my god. The example I use in my uhology discussion is yes, none of us, or very few of us, are skydivers, I am not. But what one thing in your business situation, if you ever forgot it or neglected it, could be fatal or really damaging to your business. The not locking or not renewing insurance, and then something happens. Uh, in in the photo business, you can all think of what would be really terrible.

Gary Pageau: 25:52

Oh, yeah, just neglecting the order, not maintaining your equipment. Yeah.

Wiliam Holsten: 25:56

So so I've I've begun writing monthly. My book has a bunch of examples, but each month I publish uhology, the newsletter, it it highlights uh a new example and some lessons you can you can learn from it.

Gary Pageau: 26:09

Awesome. Well, where can people go for more information about the book and the newsletter and all things William Holston?

Wiliam Holsten: 26:17

Well, but that it's it's my name. My name is William. It's my website, my name.com, William Holston, H-O-L-S-T-E-N dot com. And there you can find information about my teaching, the book. Uh, you can go to the resources section and find the uh oology monthly news. You can sign up for it. And you can also, uh when you get to the landing page, look for this $10,000 mistake checklist. It's uh the it describes all eight of the most often entrepreneur blunders, and it includes what is a mistake, why does it hurt, and how do you goofproof it? What tools can help you avoid those things? We've talked about about four of them. There's four more, and there's more coming, by the way. Williamholston.com.

Gary Pageau: 27:05

Awesome. Well, thank you so much, William, for your time and expertise. Really enjoyed the conversation, learned a few things, and uh it was just kind of fun to uh hear how you were able to turn a kind of side gig into a patented product. I mean, that's a whole nother story. So thank you so much for sharing that.

Wiliam Holsten: 27:24

Thank you, guys. Uh I appreciated the invitation to be here.

Erin Manning: 27:27

Thank you for listening to the Dead Pixels Society podcast. Read more great stories and sign up for the newsletter at www.theadpixelssociety.com.