Why Indecision Will Kill Your Business ft. Len Ward

On this week’s episode, Jana sits down with entrepreneur and former Wall Street VP Len Ward, who walked away from the traditional corporate path after watching his e-commerce business collapse during the 2008 financial crisis, and then rebuilt his career by betting on a digital future most businesses still didn’t understand.

Len takes us back to the moment everything changed. After years of success selling high-end event tickets online, the housing crash, industry strikes, and collapsing consumer demand brought his company to the edge of failure almost overnight. With a wife, young children, and only weeks of runway left, he was forced to make a decision fast: return to Wall Street for stability or take a risk on an entirely new business.

What started as helping one company with online marketing quickly became something much bigger.

As businesses scrambled to figure out the internet, Len realized he had a unique advantage: years earlier, he had already seen the digital shift coming while working on Wall Street during the dot-com era. While most companies still questioned whether the internet mattered, he was already building systems around it.

But the transition wasn’t easy.

Len opens up about the emotional weight of entrepreneurship, from skipping paychecks and questioning whether the business was over, to navigating imposter syndrome in boardrooms full of attorneys and executives. He shares how making fast decisions, trusting his experience, and embracing uncertainty ultimately became the foundation for building a successful marketing company that later evolved into an AI firm.

This episode breaks down:

•  Why indecision can quietly destroy momentum in business and life 
•  How past experience becomes your greatest advantage during uncertainty 
•  The hidden emotional cost of entrepreneurship and making payroll 
•  Why the ability to pivot matters more than having the perfect plan 
•  How recognizing massive industry shifts early can create opportunity 

Len also shares the lessons he learned from rebuilding from scratch, including why he believes most entrepreneurs overthink risk, underprice their value, and forget to trust the knowledge they’ve already earned through experience.

Because at the end of the day, success isn’t about avoiding failure.

It’s about making the next decision before fear makes it for you.

Where to find Len:

• linkedin.com/in/lenward
• AI Consulting & Implementation New Jersey and Philadelphia

Where to find Jana:

• https://janaaxline.com/ 
• https://www.linkedin.com/in/janaaxline/
• Instagram: @unstoppableleaders
• TikTok: @jana_axline 

Transcript

SPEAKER_00 0:00

You know, I was at the stage right there. I was at a crossroads in my life. I was married, I had a couple young kids, real young kids. The problem was my business went from doing really well to almost overnight grinding tools. That's how quick this was really happening. Yeah, we were weeks away from crouching. I had to move fast. Me, there was no net at all. Zero. I hit, I was hit crap.

SPEAKER_02 0:30

Today I'm here with Lynn Ward, who is a former Wall Street VP who transitioned from high-stakes finance into entrepreneurship and now leads an AI firm helping businesses adapt to a rapidly changing landscape. Thank you so much for joining us today.

SPEAKER_00 0:44

Appreciate you having me. Looking forward to it.

SPEAKER_02 0:46

Yeah. And so I just want to dive right in. So can you talk to us about a moment where you made a decision that changed the momentum that you were on?

SPEAKER_00 0:54

So I think the decision I made was going back probably in 2000, probably nine, uh, maybe even a little bit before that. But I was after my time on Wall Street was done, I was part of an e-commerce startup where we were selling um high-end luxury tickets. So you have to start thinking like Broadway seats, great concert seats, things like that, football seats, things like that. Uh things were going well. We built the economy where we built the company up. I started learning a little bit about digital marketing at that point because that's right when things were just starting. So this is going back in 04 when I was doing that. And then the decision's coming in a minute. Um, so I had to really kind of learn how the whole new digital landscape was working. I was lucky enough that I came from a background on Wall Street where, like, okay, I saw the beginnings of all this happening. So I was able, it was part of an e-comm startup, we built it up, we did pretty well, but then the housing crisis happened in 08, 09, and everybody was not really spending a lot of money on event tickets. Like back then we were selling wicket tickets for like a thousand bucks for a pair. It was crazy. Um, and that was like all done, you know. So I've people remember living through the 08-09 crisis, it was really, really rough. So the problem was my business went from doing really well to almost overnight grinding to a halt. That's how quick this was really happening. So, you know, I was at the stage right there. I was at a crossroads in my life. I was married, I had a couple of young kids, real young kids, you know, and I came from a Wall Street background. So I was like, okay, I could probably get my resume together and go back there, uh, you know, or potentially, you know, work my way back in there to some capacity. Maybe I could try to maybe start something on my own. But I got approached by an individual who said, that stuff you were doing for your e-commerce company where you were kind of getting, you know, going online with Google and all that, like, how did you do it? And I started thinking to myself, I'm like, wait a minute, you know, maybe this is a business. And this was when digital marketing agencies were really in a very, you know, infantile state. Like it would, they were very, very new. I know a lot of agencies, like say they're around 35 years, you haven't in digital marketing. So digital marketing agencies really started kicking in about 05, 06. So I had the opportunity and I and I talked to that individual that I knew and I worked on their website and I got some things rolling for them. And that's when I said to myself, all right, I think I can do this. So I remember talking to my wife about the decision, and we basically were like, all right, we're gonna give this a year. If it doesn't work, then I'm gonna get my resume together and go back to try to figure something out. Because you know, when you're married with kids, you gotta try to, you know, you gotta put money or food on the table. So that was really the pivotal decision.

SPEAKER_02 3:16

Yeah, let's before you go that far, let's dig into a couple of those things. You know, when you were looking at the company that you um owned that was then struggling, the the event, the ticketing company. What like what was your runway to make a decision? How how dire was it? How quickly did you have to figure out how to pivot? Do you r recall?

SPEAKER_00 3:36

Yeah, we were weeks away from crashing. I had to move fast. So it was literally, you got to move really, really quick. I didn't have this long like after Wall Street when my time time came to an end, before I decided to say I'm gonna go out on my own and looking for businesses to buy. I had luckily the package I had leaving Wall Street. I was able to take some time and really, you know, figure out what I wanted to do. Thank God. They were they actually, it was a actually a very nice split and it actually worked out well. But this one was different. You know, you looked at the money, you looked at everything, you're like, all right, well, you know, I gotta do something fast. And I mean, I I I thought about a lot of different opportunities, meaning like, what am I gonna do to hustle money? At that stage, you're like, you gotta start getting money in the front door. So it came down to weeks where I had to make the decision. I just said, all right, I'm gonna see what I can do with this.

SPEAKER_02 4:22

And did you have a team at the time where there are other people who were potentially impacted too?

SPEAKER_00 4:26

Yeah, we put we had a few people working for us. We were really small. It's funny because that's when we really realized um internet marketing and so forth. You didn't really, or internet sales, you didn't need this massive team, right? Because our inventory was all skinny pieces of paper. That's when tickets were still paper. So holding them and shipping that was actually pretty easy. Yeah, there was a couple people involved. For them, they you know, the other person involved did have a job at the time, so they were kind of like a part-time job, so it wasn't hard for them to kind of start picking up more hours. For me, there was no net at all. Zero. If I hit, I was hitting the ground. So I had to really make a very, very fast pivot and adjustment. I guess I was about 35 at the time, something like that.

SPEAKER_02 5:04

And did you like extrapolate what that would mean? I mean, you said you had small kids, you were married. So if you couldn't turn this around, I mean, are we talking about losing your house? I mean, was it pretty significant?

SPEAKER_00 5:16

Yeah, well, I think a lot of people in 08-09, if you really live through it, it was significant for a lot of people. I mean, I I almost everybody I know was really, really, you know, they were struggling, especially if you owned a business. I mean, you were really struggling. So we had a little bit of runway, you know, financially, you know. I mean, I I did make a couple investments where it was never horrifically dire, but it was bad. You know, I'm not gonna sit here and say, Oh, it was easy. No, it was like if you don't get a job here soon, like you're gonna have a problem paying the bills. So I had to make decisions really, really fast.

SPEAKER_02 5:47

And so when you were looking at your options, you mentioned starting your own company, a new company, you mentioned going back to Wall Street. Did you do any analysis on whether the current company you were running could pivot or if there was any way to ramp that back up? Or how clear was it that that it you know wasn't viable?

SPEAKER_00 6:08

There was a lot of options. Actually, a really good question. There was a lot of options. One of the things we did before is we held all of our inventory. So we almost were buying events and investing in events where we thought there would be an appreciation. We literally ran the company the same way you would run a mutual fund. Like you buy stocks because you think they're gonna go up. We were buying events because we knew that these certain events, based on the criteria that we created, would go up. So we pivoted and flipped and said, Well, what if we didn't do buy the inventory and we just sold other people's inventory, which then was the famous term called drop shipping, which a lot of people were not doing at the time. So basically we could go out, we could market because we were really starting to gain some traction on digital marketing and start selling the other event tickets. And we did do that, and it worked for a little bit. But the problem was that you were realizing to really make money in that business, you have to be able to identify tickets back then that were now this is unheard of. But back then it was like under 50 bucks face value, under 100 face value that you could then mark up 35% and so forth. But the problem was that people weren't spending anything on tickets anymore, unless it was like, you know, they were getting them for really, really cheap. So we realized that was really coming to an end quickly as well. So we had some stable stuff that kind of helped out. But you know, the other thing that heard us too is that Broadway went on strike. Uh, that's when Broadway years ago went on strike, and that was crushing for us because it's one of our backbones of our business. And then the NHL went on strike, which, you know, so we're like, okay, so we used to do great on hockey tickets, great on Broadway tickets. We were season ticket holders for the hockey on a lot of different teams, and we're sitting there saying to ourselves, what's next? You know, so housing crisis, two major strikes that impacted our industry. Uh, then the drop shipping wasn't working out. So it got to the point where it was like, okay, we we have to, we have to honestly figure out what we're gonna do and just having a couple conversations. If you've ever been in the business world when your business is over, you just know it. There, there's just it's not even just the money that's not coming in anymore. There's just this feeling where you just know it's there's there's no way off the island, like you're done. It's it's over.

SPEAKER_02 8:06

Well, that's really interesting because I mean that's that's obviously in life a common thing we ask ourselves, when do you push harder versus when do you stop? I'm pretty sure there's a book on that. Maybe it's the tipping point or one of them. But um how did you like were the what were the signals uh that kind of told you no, it's time to stop? You've mentioned a couple. You mentioned the strikes, you mentioned it didn't feel like people were buying tickets, but you know, that potentially you could weather for a year a couple of years and bounce back. Um so but what were the other maybe signals you were taking in at the time?

SPEAKER_00 8:40

Cutting back your pay. So the number one thing I tell people when they're starting a business, the best piece of advice is that you don't hire an individual until you're fully getting paid, you know, and a salary that you can that that you know that you're worth. So it was okay, well, we'll take 50% less pay uh this time. And then it was like, okay, well, we'll skip a paycheck. And the stress that can put on a family, especially a young family, when you're skipping paychecks can really can really ramp up. So that's it was like accumulation of events of everything I just told you. But then when we were both like skipping pay, the two partners running it, then we just knew like, okay, we can't, because he was about 10 years older than me with kids of his own, but we knew at that point we can't keep skipping pay. We would go, and the other thing was funny because we always knew when you know you you went on, you opened up the office, you turned on the computers, you would look at your orders, and they were coming in back then. Orders are coming in from eBay and your website, all different areas. You know, and you'd have like, you know, I just remember sitting at our desk and we'd be processing a hundred orders overnight. And you got to the point where you were processing maybe five. You know, it literally was going like that. But it was the skipping of pay, and I remember going like three, four weeks in a row, not just, you know, like, okay, that's it, and then we got paid again. No, it was then you would go a couple months and then you would skip pay again. So you've never really been in business unless you really started missing and skipping, you know. And that's when you say to yourself, you know, you would never work for somebody if they were just not paying you. So why would you continue down the road you're on if you're not paying yourself? This means this is no longer a viable business.

SPEAKER_02 10:05

I suppose unless it's like a strategic decision, because you're like, I need to put this money in so that I can grow it in another area versus, you know, but then you you've made that conscious decision because maybe you don't want to take a loan or maybe you don't want to put in more capital, but yeah, that makes sense. So when you were when you were, you know, realizing that, hey, this company's not viable anymore, I've got the Wall Street option. Did you at all explore you know, other business ideas, or because of this um moment where the person asked for help and you were you're like, wow, I can do this. Was it pretty clear what what the other business option was?

SPEAKER_00 10:47

I actually went on a couple interviews, believe it or not, which was funny. I interviewed with Verizon for digital marketing, like to be one of because back then they were just randomly throwing out job descriptions of director of digital marketing. And I remember being interviewed, I'm like, you know, I I know I know a little bit about digital marketing because I'm doing it, but these people have no idea about digital marketing. Like, so I'm getting interviewed, I'm like, you guys really have never done this before, have you? I actually was uh QVC. I got interviewed for digital marketing, and it was such the new era of all of this stuff. But I remember going on these interviews and sitting down, even got interviewed by a casino down Atlantic City, and for some reason I wanted that job. I don't know why. Um now in hindsight, I'm like, I would never want to do that, but just because it's a it's a lot of work. But um, I remember going on the interview and I remember just kind of driving away. I'll never forget I called my wife the one time, and I'm like, I think I'm unemployable. Meaning, like, once you cross that Rubicon, you know, running your own business, I'm like, nobody's gonna hire me, you know. So um, so I realized that. And that was, I guess that kind of brings me to the point of where, you know, driving home, like that was the decision. I'm like, uh, nobody's gonna hire me. Like, it's just this isn't gonna happen. I was getting a little older. I remember back then you worked with somebody who was doing your helping you, you know, kind of clean up your resume and so forth. I know that businesses exist now, but ChatGPT is kind of taking that away. You know, but I remember going through and I'm like, well, I'm kind of getting closer to 40. I'm like, I don't know who's gonna hire me. And she's like, well, you are moving that age where, you know, it kind of gets a little more. I'm like, wow, really? You know, and I just is like, so between the age, the young kids, uh thinking I'm unemployable, really always was an entrepreneur at heart, believe it or not. I mean, even though I worked on Wall Street, I've always ran and done my own types of businesses. That was the stage where I'm like, let me give this a shot. Because, you know, the the luck I had was not only was I able to work on Wall Street during the dot-com era when I saw these companies rising and I saw what was gonna happen, but then I worked in it by literally having an e-commerce company. And I would look around at every single business around and be like, every single business is gonna have to be online. Every single business is gonna need a website. And that's when I looked around. It was a true heyday of like a lot of companies didn't have it. So it got to the point where I did do that new business. I tell people all the time, I'd unplug my phone. I was a solo practitioner. I literally unplugged the phone for four or five days at a time because I couldn't take any more business. So that's kind of how I got there.

SPEAKER_02 13:02

When you when you first started down the path, you know, you just mentioned that you had three, three or so interviews or whatever. Was that because it felt like the safe options? Yeah.

SPEAKER_00 13:12

I felt like that's what a husband and dad should be doing, you know, because at that you the older you get, the less inclined you are and appetite you have for risk. Unless you have a tremendous safety net, unless you have tremendous amounts of finance, your husband or wife or your partner, whoever it may be, unless they are you don't have kids and let's just see there you don't there's like not necessarily you don't have a whole lot to lose, right? You know, and I'm not saying that that's the right way or the wrong way. I'm just speaking for myself. Like I my appetite for you know for risk was always there. I know it drives my wife nuts when I how I run businesses, but but it but then you know you you come home and you're looking at a couple young kids and you're like, you know, I I can't I can't make decisions like I was making when I was 26, 27 years old. I gotta start acting like a guy moving towards 40 with a couple young kids. And by the way, there was another one on the way. So it was like so that's why I was like, I'm gonna start interviewing, looking for stuff. And you know, lucky enough I had the support at home where it was like, you're an entrepreneur, go build your business, everything will work out. So I was lucky in that in that right.

SPEAKER_02 14:13

Aaron Powell And did you have a a team, not not necessarily a literal team, but like people who you go to to bounce these type of ideas off, get advice from people who've been there, done something maybe before, or you know, when you were making this decision, who did you turn to?

SPEAKER_00 14:30

It was me, believe it or not. I you know, because a lot of people weren't in the in the situation I was in. And when they tell you being an entrepreneur can be lonely, back then is when I used to never believe that. But then back then I I was like, oh wow, because you can't have this conversation with somebody in your late 30s, early 40s about running a business and the stress. And I used to tell people all the time, if you've never stressed out over the term I have to make payroll this week, um, then you've never truly run a business because that is the scariest line of business owner can ever have go through their head. You know, obviously you have your wife, you have your family, I have friends, you know, I mean, that I could lean on and talk to, but it wasn't it wasn't there. And and that's what makes an entrepreneur, that's what makes you grow, that's what makes you get self-sufficient, is when you you realize no one's coming to save you, and you literally have to do this on your own. So however you have to work through this stuff in your own mind, that's what you have to do. I think what I did a lot then was lean on a lot of different, you know, books. And like, like I really leaned on really good business books of people that have been there before and really read their stuff. And, you know, and that was the kind of stuff where I was like, okay, so there are people that have been down my path before. I knew who they were, but where were they? This was remember, this is pre-social media, just as rape social media was just starting to happen right then. This was pre-you know texting friends, like you were the text, you know, you had the call back then, God forbid, you know, and get on the phone and you know have a conversation. So it was different then. So I just threw myself into reading and educating and learning, and I think that's what I really leaned on. And I just constant, constant notes, constant high. I always had highlighters and post-it notes next to me, and and that would just help me make decisions. I mean, sometimes it was, you know, parallelization, or is it parallelization by overanalyzation sometimes, or if I'm saying that line right. But that's what kind of got me to the point of helping me make decisions.

SPEAKER_02 16:20

Is there a book that stands out to you that might be?

SPEAKER_00 16:22

I think Yeah, the one I think everybody should read if they're ever, ever thinking about starting a business is the e-myth by Michael Gerber. A lot of people know it, a lot of people don't, but to me it's the greatest book written about being an entrepreneur or not. You realize whether you're an entrepreneur or not, it's called the e-myth, the entrepreneurial myth. But if you're going to do it, this is how you have to do it. And if you can't do it this way, you have to ask yourself, are you more of an employee, more of a manager, or are you an entrepreneur? So that's the book that I think that I always came back to and I leaned on. I was like, that was one of the ones that really made a big impact on me. There's a lot, but that's the one that I always come back to.

SPEAKER_02 16:56

And so when you helped your friend out and you're like, hey, I think I could make a business out of this, did you like analyze the addressable market? Did you, I mean, how did you feel confident that you could ramp up fast enough with So I I went straight to bootstrapping, which is back then you would post things on Craigslist.

SPEAKER_00 17:17

You know, it was like it was under the computer services. I used to, I actually put an ad in the newspaper, if you can believe it. Now we're moving more towards 09, 2010, right? Right around now. And my thing was, let me see what happens. So I would, you know, put it because I knew we would sell back then the the ingenious way to sell tickets throughout the country was putting ads up on Craigslist was huge back then. So putting ads up in like, you know, Tulsa or Miami, wherever you're looking to kind of sell event tickets. So my thing was, where do I know? Where did I used to have my client base for Wall Street? But where did I know business was definitely booming, small business, and for what I thought. And I'm like, let me put a couple ads up there and see, hey, I can help you get on the internet. That's all it was. I can help you people find you online. That's all I wrote. And people used to call me the computer guy. That's wasn't even which is so funny, where it was a digital marketer. People couldn't even say the term SEO back then. They used to call it CEO, you know, which was funny. Um it was funny. So I gave it a shot and that was it. So I was it was a testing market. Now you can you know, I can build a complete T A M on an LLM model, and it's like, you know, it's like the greatest research you've ever seen. But back then, you had to go test it. So I tested it, Craigslist, I tested it, you know, you know, on the on the newspaper, I tested it by doing certain types of placement ads in certain things. Like, you know, you would put an ad in like the church bulletin, I'd put an ad on diner, you know, um, diner lab, you know, placemats where you're sitting down having something to eat. So it was at that point, I was realizing even me doing that little stuff, I'm like, you are a marketer at heart. Like you're you're pulling out what you've always were. You just never realized it. Like, you know, and it's like kind of looking at different things. And what I did worked. I started getting phone calls. I started getting people come to my website, um, and so forth. And I realized, I'm like, okay, so you're a little bit more than a digital marketer. You're clearly something with marketing, you know. So, um, and that's kind of how I started to build it slowly but surely, but that's how I identified the market.

SPEAKER_02 19:13

So, you know, that sounded like it might have been a year or so process that you were iterating through. So during that time, was your first company still doing some business, or were you still looking for jobs at the same time, or were you all in at that point?

SPEAKER_00 19:27

No, at that point I went all in. Because once I decided to go all in, I'm all in.

SPEAKER_02 19:31

And and what drove that I'm all in then?

SPEAKER_00 19:34

Because I knew that there was something there, because every single time I put an ad up, my phone started ringing. Like I mean within hours. And it's not because I'm a great marketer. That's not what I'm saying. What I'm saying is because there was such a demand for that back then, and there was no real people to fill it. And if they were filling it, you know, I'll be honest with you, being a business person, you could see the bullshit right away when you sat down to have a conversation with somebody, like, they're just selling me, they're making stuff up. I I think I came at it from an angle where when I would talk to people, I ran my own businesses, I succeeded, I failed, I did different things. So I would have a conversation with them about business opposed to I'm gonna get you ranked on Google. Like, and that's where I think that people like that. But the moment that I knew that I should go all in was when if I were getting five calls out of the day, it would be five different businesses. But within a couple months, if I got five calls a day, four were attorneys. And then I realized I'm like, wait a minute, nobody advertises more than attorney. Never forget, I drove home and I just went back and I looked at the yellow pages real quick and I'm like, I turned to the back of the book, attorney, side cover, attorney. Went to the lawyer section, all attorneys, and then I went all in on attorneys. I'm like, that's the marketplace. And then I built a business going after all attorneys.

SPEAKER_02 20:46

Wow. Um, and when you were when, you know, you I guess in that initial one or two tests where, you know, you made that decision, I'm gonna go all in. Did you do like any sort of financial modeling then of how long is it gonna like how much do I have to charge and how long is it gonna take me until I can support myself? And does that reconcile with how much I might have in investments or savings? Any sort of analysis like that?

SPEAKER_00 21:10

No, none of that. It was driving a car and just is the gas gonna run out or not? It was no, I had none. Like every business owner, like you're either excellent at financing, you know, when it comes to the books, or you just choose to ignore it. Like a dope when I was younger, I chose to ignore it. Um, just making up pricing as I was going because you know, you were to ask somebody, hey, how do I charge an individual um, you know, to get them ranked on a website and to get them business? And everybody came and the coming from Wall Street, I always thought this was a little crazy. Everybody came, arrived at the well, we're gonna charge an hourly rate. Charge an hourly rate. You just commoditize yourself. You should be charging for an outcome of what you're doing. No, and nobody did that back then. So we all fell into this hourly rate. And then back then, I fell into an hourly rate of 45, then 50. I got up to 100, 150. And then as I started hiring employees, which we could touch on a Like I started bringing the number up, but I always and still to this day felt an hourly rate was the stupidest thing somebody could do in the service-based business. You charge upon the outcome and what you're doing and your experience on the outcome, not on an hourly rate of the work you're doing.

SPEAKER_02 22:13

Yeah, completely. So reflecting back when you were looking at your options and you were thinking about going this route, did you miss anything? Like any information in that maybe it worked out in the end, but in your kind of thinking through this, should I do this? Did you did you miss any components?

SPEAKER_00 22:30

You mean where I made mistakes?

SPEAKER_02 22:32

More about like information that would have been useful to make the decision while you were making it that you didn't have. And maybe it's would have recon maybe it would have confirmed the decision you made, but just things looking back where you're like, oh, I didn't have that piece of information. Surprises, maybe.

SPEAKER_00 22:49

I think what you hit was that on right there. I I think it was truly not understanding how to charge for an unknown business. It was it was really like if I would have gone back in time, if I go back in time, I would have 10x the business right away. Nobody knew what to charge back then, you know. And I and I I wish I knew that information. I I didn't know it. I wish, you know, the the mistake I always come back to is I'm glad I'm in the spot I'm in because I really generally do like marketing. But the mistake I think I made back then, a decision I made, was I knew a little bit more about the web than a lot of other people, just because I was making it my life, not because I was better than you. But I wish I would have gone a little bit more in on what I can do with that knowledge opposed to commoditizing my knowledge and giving that out to people. And I think there's a lot of brilliant digital marketers that I've come across. And when we have a conversation, we come back and say the same thing. It's not that we don't want our clients to absolutely, you know, do tremendous, but what if we would have taken that knowledge and invested a little bit in ourselves and started building up businesses where, you know, it was internet reliant and so forth. And I know you can come back and say, well, you did with the ticket business, but there was so many opportunities for businesses back then, you know, between drop shipping, affiliate marketing, so much stuff you could have done where quite honestly, a lot of major people you see now in marketing and some personalities, like you would call them influencers, that's how they made their their hundreds of millions of dollars. They they said, no, I'm not gonna give you the information I'm learning. I'm gonna build it for myself. The problem is that it comes back to why'd you make the decision? I have bills to pay, I have kids, I have a wife, I have a home. You know, that was kind of the decision you made. But that's the one decision if I look back, I'm like, I wish I would have taken maybe six months to see what I could have done opposed to selling my knowledge out to somebody.

SPEAKER_02 24:33

So let's talk about some like the underlying part of the ultimate decision. So you're you're evaluating do I go back to Wall Street? Do I start another business? The economy sucks. I have a short runway because I have I have kids and a wife and and bills to pay. What was the principle or the belief that ultimately drove you to decide I'm going to um I'm gonna go out and start another company?

SPEAKER_00 24:59

Well, I know I could do it. I've never, I mean, in a and I say this in a in a play way, I I never had any doubt on myself. Once I learn something, once I I do research, I think, to the point where it becomes, it gets ridiculous. You know, like I mean, once I start something, I just get completely all in and know it. And I just knew that if I honestly would walk into a room and I knew more than everybody in the room in a in a professional manner, I don't mean being like a you know jerk when you walk into a room, but if you knew more than everybody in the room, that was always going to put you ahead of everybody else. Don't interject, don't, you know, don't force your opinion in. But if you know every more than everybody in the room, because of your research or because of what you've done and the experience you had, I knew that if I got into the front door with anybody that they would, I could connect with them, you know, and and and say, this is what I know. Of course you have moments of doubt and imposter syndrome. That that's gonna happen no matter what. Yeah, and if it's and it still happens, but I just knew I'm like, every single time I was researching something about the internet, I would pair my Wall Street experience together, you know, and then I would pair running the business, and then I would look at what was happening, you know, with online, and I'm like, I'm beginning, I I see how this all these dots are connecting. So I never had a doubt. And I remember saying, I'm like, I'm good, this is gonna work. Whether I become insanely successful or not, I'm like, I'm gonna be able to pay my bills, like because of what I what I've known. And I think I understand how you have to do it. And at the end of the day, my line that I told people, and they're like, well, why should I hire you? Or why am I doing this, or why am I paying you? And I would tell them, you're hiring me to make you money. At the end of the day, you're hiring me to make you money. That's that's my job. Um and so I don't know if that answered the question, but that's really why I I I really at the end of the day, you know, I I never really doubted myself. I just I I knew that I knew that I could do this.

SPEAKER_02 26:45

Yeah. So you had it was it was historical evidence of your success coupled with research into what you wanted to do, saying, yeah, this is gonna work. And so when you mentioned imposter syndrome, what did what helped you get through those moments?

SPEAKER_00 27:03

You know, that's a good question. And I, you know, I I think, you know, just you know, telling the voice to shut up, like we all have to when we're in a meeting, you know, like I got to get through this meeting. What helped me get through imposter syndrome back then, and what would even help, I think, individuals now if they were listening, is when you start getting intelligent questions coming back to you, like when you say something and then somebody comes back with an intelligent question and you're able to answer that question, you're not an imposter. You belong. You know, you you you actually are the one who's dictating the conversation. So what helped me get over that, because sometimes they go in these law firms, let's call it the way it is. You sit in a law, you know, go into a boardroom with like, you know, 10, 15 lawyers. Why should we pay you money to market our firm? These are cats making 25,000 times more money than I'm making. And that, you know, and I'm just like, oh my God. But, you know, I just walked in, I knew my information, I knew what I had to do, and they would ask a question, I would ask a question. And when I used to watch them like writing notes down, that's when I knew I had it. That's when I knew, like, okay, imposter syndrome would drop. I'm like, okay, I I know what I'm talking about. If you're prepared, you know what you're talking about, you're willing to have a dialogue with individuals and realize that you're not right on everything and that you can help educate people, imposter syndrome drops really quick.

SPEAKER_02 28:11

And then was there anything that you maybe at the time had a different perspective or an early perspective on in regards to this digital marketing SEO space? You know, because you were saying it was high demand, people called you, let your phone ringing off the hook. So was there something unique that you saw before others did?

SPEAKER_00 28:33

Oh, I mean, I think that goes back to my experience on Wall Street and being luckily, lucky enough to sit in the room and I was a young, dumb kid working there, but I was fortunate enough to be in meetings where I knew it was coming. So it was almost like I had the blueprint of what was coming before people knew. I knew how important the internet was going to be. I mean, I remember sitting in in rooms where which is where IPOs were about to happen, initial public offering, and that's when all the dot-com error exploded. Forget all of that exploding and everybody losing money. I know that was horrific, but but when the dust settled, we all looked around and the world was never the same. The minute you went to Google the first time or Yahoo or whatever, it was never the same again, much like when you went to Facebook and then a ChatGPT and so forth. So, like I think I always knew the world that was coming. So I think that kind of couples with, you know, did you ever, you know, how did you know you were going to make it and so forth? Because a lot of people, much like the world we're living in right now, I don't think people really understand what's coming or what's here. It was the same thing that I saw back then. And I knew back then it was about five, 10 years out of where the whole world will be digitized, where now we're down to like eight months. Um, but I think that's what it was. It was being exposed to that, kind of like almost like somebody giving you the cheat code. And I and I had that cheat code as I was talking. Because when people I had people tell, uh, it's never gonna make it, and you're gonna tell me that I'm gonna stop doing billboards. And I, yeah, you you're going to. And they would laugh. And I knew deep down, all right, you know, I I know you'll be back in a year's time and you're gonna want to spend five thousand dollars a month on on just Google AdWords alone, and you're gonna get rid of that billboard.

SPEAKER_02 30:08

So, I mean, you've touched on it. Obviously, it was successful, but can you talk a little bit more about the outcome of, you know, making this decision?

SPEAKER_00 30:15

So I mean, you know, I like to tell people all the time, like I I was a solo practitioner, I was a freelancer. Um, I was lucky enough to be hired by a bunch of companies. I think I was called director of marketing for five different companies, if you Googled my name, because they have me on the website. So I was able to get business that way. But I closed my door one day, I walked back in and there was 25 eyeballs staring at me. That's how fast I started hiring people. Um, and you know, accounts were ramping up rapidly. Things, I mean, I think the growth was probably a little too fast, to be honest with you. But that was the digital marketing heyday. And that's when I knew obviously at some point you arrived, you're like, okay, I obviously I made the right decision because here I am, 2026, although we've pivoted more towards we are now AI versus marketing. But yeah, so that shows you another thing. I another, another crossroad came for me where here we are at AI and marketing, and what are we going to do? And let me give this AI thing a try because it's just reminds me of the exact same thing where I was 15 years ago, 20 years ago. Now I'm gonna go do this. So that's kind of how I arrived at it. Now, you know, I got a nice little small, tight team, but you know, obviously the decision worked out, I would say.

SPEAKER_02 31:15

Yeah. Were there any lessons learned you had from that whole experience then?

SPEAKER_00 31:20

Yeah, you know, the line I always live by, uh, because somebody told it, a very famous person told it to me years and years ago was indecisional kill you. And when people say, just give me one line that that that would sum up everything in your career that would help me get to my next stage of the career, I say indecisional kill you. Um when I was a kid, I was lucky enough to caddy for Charles Barkley. Everybody knows Charles played basketball for the Sixers. So I was at a golf course, and I asked Charles, I said, tell me what made, you know, I'm a big fan, you know, I'm live in the Philadelphia region, so he was a Sixer. At that point, he was straight out the Phoenix. But, you know, Charles, what made you so good, you know, and we just kind of had a conversation. I was like, you know what, you know, how why are you better than the next guy? And I never forget. He like looked at me, we're on the 18th hole. He looked at me and he goes, you know, Lenny, he goes, what made me better than everybody, what made Michael Jordan better than everybody? He goes, There's always gonna be a guy out there athletically better than you, smarter than you, quicker than you, fashion. He goes, but indecision. He goes, I watch these kids walk on the court, he goes, and I see the ones that are gonna be quick to make a decision and not think about it, and that's it, and they move to the next decision. He goes, and I say they're gonna be great. He goes, and I see the kids with more talent than anybody, and they don't know what they're gonna do. And then there's like they him and how about a decision. He goes, Lenny goes, I never thought about it even twice. He goes, I made a decision and that was it. And that line stuck with me my entire life. And I actually think that line helped me get through a lot of different times, and I'm like, I'm just pondering a decision like we all do in life, right? You just you're wringing your hands over something and indecision will kill you. So the longer you think about it, whether you're right or wrong is irrelevant, the longer you think about it, the closer you are to death and you don't realize it. Make the decision and move on, right or wrong.

SPEAKER_02 32:50

What happens from your perspective if you make the wrong decision?

SPEAKER_00 32:54

I think I would have ended up probably working for somebody like a company. I think I would have maybe, I don't know what type of business I would have been in, probably sales. I would have been miserable. I would have been miserable. Yeah, I'm just not a, you know, I can't sit at a desk nine to five. Like, I mean, I with my own business, the funny part about it is I probably work, you know, 24 hours a day, seven days a week, but it's on my own time, right? You know what? So you're on your own time. You it's my own time. So my freedom of time is more valuable to me than any paycheck you can give me. So I think that that's what helped me make that decision. Because if I didn't, and like I said, like your question is of what would happen, I probably would have been sales or something. I probably would have done well, but I would have been miserable just because I'm sitting there answering to people and you know.

SPEAKER_02 33:36

So I guess I was thinking, you know, if would people make so you, you know, you were saying indecision will kill you, so make a decision, right? And that act allows you to see an outcome and it gives you an opportunity to pivot. So I'd almost put forth to you maybe you would have gotten a job, but you probably would have gotten some feedback about what how you were exactly what you're saying. I'm miserable or I'm not liking this. Yes, I I'm succeeding, but this is not where I want to be. And and my, you know, guess would be that you'd probably start looking for opportunities to do what you loved.

SPEAKER_00 34:11

You're probably right. Yeah, I probably would have. I I think, you know, I'll I'll recant what I said. I somewhere I would have ended up owning my own business. Even if it was for myself or something, I I would have. There's no question I would have.

SPEAKER_02 34:22

Um I think that's what's important about just making a decision, is because once the decision is made, you start getting feedback. You know, and so unless we're talking about a life or death situation, I haven't been in that those shoes yet. But anytime you make a decision, you get feedback and you have an opportunity to adjust the direction you've headed.

SPEAKER_00 34:42

Yeah. No, I agree. And you know, it's funny because you know, it's not like, you know, I I've reinvented the wheel or even like Charles Barkley lucky enough to hear that. Or, you know, you go back and you hear people like Anthony Robbins, his entire foundation of what he teaches people is making fast decisions. And when you go through and listen to all the great business people, they all they that's the term they all come back to. It's it doesn't make a difference whether you're right or wrong. Each decision leads to another decision, which leads to another decision. And sooner or later, as you start making decisions, like Anthony Robbins will tell you, you're building up that muscle power to make fast decisions. And when you go look at the absolute great business leaders in the world, they all come back to say that they just make these fast decisions. They don't wait on it. They just do it. And if they're wrong, then they make another decision to fix what was wrong. And they go, but it's that lack of decision that really, really hurts people in business and in life. I've always said that.

SPEAKER_02 35:32

So maybe to recap, basically in your situation, you you relied on past experience, which I think a lot of people forget to do when they're making it in a tough position, but you relied on your b past successes. You did research, whether it was experimental or actual, you know, um research into the market, that also was helped through your time on Wall Street, knowing what the landscape was looking like, and you made a quick decision. Yeah.

SPEAKER_00 36:00

That's it. I would say that's that's that's in a nutshell.

SPEAKER_02 36:03

And so, you know, what's the one thing you want to leave, I guess, top of mind with everybody or carry forward from this conversation?

SPEAKER_00 36:11

I think no matter how bad it gets, I'm just gonna talk, you know, personally um and professionally. I think no matter how rough it gets, so long as you wake, have a, you know, the sun's rising, you have another shot at it. You know, and I know a lot of times losing a business, which I have, is very, very difficult. It's it's a really, really gut-rushing thing to go through. Not only is it forget the financial side of it, which we know is crushing, but it's the mental side of failure. But I've never met a great business owner ever in my life who's not failed at a couple businesses, you know, to eventually get to where they need to be. So no matter how bad it may look, even if you have to go all the way back and bootstrap, no matter how high you were, if you got to bootstrap all the way, you know, I went from working on Wall Street and living in Manhattan to putting ads on Craigslist to start all over again. Like you can absolutely do it. And I say this directly to my generation, which is Gen X, which I think is a little fearful of what's going on right now with AI. Don't, if anything, that this is going to be your time to shine because what trumps AI right now is your experience and what you've done. Don't forget to look at your experience. Don't forget to keep leaning on that experience no matter what anybody tells you. Uh, because knowledge is one thing, experience is another.

SPEAKER_02 37:23

Completely. Yeah. How do you actually implement what the information you gain? And that's where wisdom and experience come into play. Well, Lynn, this has been great. If someone wants to follow your work or learn more about what what you do, where can they do that?

SPEAKER_00 37:36

They can just visit our site, comeexus.com, and you can get all our social links underneath there. Um, and you know, if you ever have a question about anything or clarification, just you know, put your name in the contact box. Uh, I am the one that answers all those contact boxes. I'm more than happy to jump on a phone call and have a conversation.

SPEAKER_02 37:52

Well, thank you so much for taking time to be on our show today.

SPEAKER_00 37:55

I appreciate it. Thanks for having me.

SPEAKER_02 37:56

And to our audience, make the decision, act on it, be accountable, and until next time, stay unstoppable.