Pamela Slim on Creating Wealth Beyond Your Hourly Rate

In this conversation, entrepreneur and author Pamela Slim shares insights into building meaningful businesses later in life and how entrepreneurship fits into the transition out of traditional careers. Drawing on decades of experience working with professionals and founders, she explains why successful ventures are less about personality traits and more about solving real problems for real people. The discussion explores how retirees and career changers can leverage experience, relationships, and self-awareness to create sustainable businesses, while avoiding common pitfalls like chasing trends or seeking funding too early. Pamela emphasizes the importance of patience, market validation, and building something aligned with your strengths and interests. This interview offers practical and realistic guidance for anyone considering entrepreneurship as part of their next chapter.

Pamela Slim is an award-winning author, speaker and agency owner who has spent three decades helping business owners scale their businesses and IP. The Pamela Slim Agency (PSA) specializes in productizing service businesses and the design and development of certification and licensing programs. Pam is the author of Escape from Cubicle Nation (Penguin Portfolio, 2009), Body of Work (Penguin Portfolio, 2014) and The Widest Net (McGraw Hill, November, 2021, winner of Best Sales and Marketing Book of 2021 from Porchlight Books).

Website: https://pamelaslim.com/

Click to see the Full Transcript

speaker-0 (00:03.907)
Welcome everybody. Today we have Pamela Slim. Pamela is an author, a speaker at Xi’an’s own agency. Pamela, it’s always better to hear from the person that I’m talking to for them to describe who they are rather than me talking. You’re the expert on you. So welcome. And why don’t you tell us a bit about yourself.

speaker-1 (00:28.29)
love it. Well, thanks so much. I’m so happy to be here. This is kind of a big year for me. I was telling you, and we did our kind of pre-recording call, that I turned 60 this year and my business turned 30. So I’ve been in business for a long time working for myself. My last real job was at Barclays Global Investors in San Francisco, where I’m originally from, where I was director of training and development. And I’ve had this really interesting journey through my career.

where I have always had a passion for learning and development, change and transformation. So the first 10 years or so were my business. I was in Silicon Valley and worked with companies to grow and scale or depending on the year, downsize as we had different economic fluctuations. And then I found that there were so many people who were actually kind of interested in my own journey of how I had left corporate to start a business that when I moved to Arizona,

in 2003, then I ended up starting a blog called Escape from Cubicle Nation, which was helping people who wanted to leave corporate to start a business. And that started a 20-year journey of doing all kinds of work with people in starting businesses. My philosophy has always been that hating your job intensely is not a business plan. So don’t quit your day job until you have successfully proven your side hustle really makes sense.

Through the years, I just have worked with all kinds of people in recent years, experts in their field, where they are interested in building something that’s really meaningful and relevant, some kind of method or a model or an approach that’s gonna make the world a better place. So the last three years or so, I moved into an agency model where myself and my business partner and our team, we help people to be building programs that we’re selling to larger companies. So that’s on the professional journey.

I feel like I have the best job in the world because I get to talk to really smart people all day and, and, know, bring something from a twinkle in the eye into a real program or product. And then on the personal side, I have two college age kids. My daughter is 18. She goes to college in Paris and is studying luxury branding. And my son is 21 and he is pre-med on a passionate track towards an MD PhD in neuroscience and neurosurgery. So.

speaker-1 (02:54.088)
That’s my, that’s the snapshot of me.

speaker-0 (02:57.998)
So just to be clear, your agency itself, it’s focused on helping people start their own businesses, start their own programs, that sort of thing.

speaker-1 (03:06.03)
The agency, it’s really for more mature entrepreneurs who are scaling their business through intellectual property. So what that means is where I worked with a lot of real early startups early on in the journey, now it’s with people who tend to have established platforms, bestselling books, and really they’ve outgrown their ability to be directly…

giving workshops or selling services directly and they want to scale through their IP. So we build licensing certification programs, help people to build more scalable models when they have time tested ideas. So that’s part of where the evolution of my business has gone as well.

speaker-0 (03:48.248)
So one of the pillars within the transition network is retirement and entrepreneurship. Have you seen much happening when people are transitioning into retirement where they’re starting businesses, that sort of thing?

speaker-1 (04:05.774)
And I see in a couple of different ways. So on one hand, there are some people who have chosen to maybe choose a more conventional track of working as an employee, which I think is a great choice, because entrepreneurship is not for everybody. So maybe to stabilize the retirement and get the kids through school and all those other things we do, they’ve gone that track. And so now they feel like they’re finally able to spend the time into something they’ve always wanted to do.

So that’s one thing that I see sometimes with newer entrepreneurs. Very often they might want to be writing the book that they always wanted to write, or I’ve seen really significant changes like selling their house and buying a chateau in France and just everything you could imagine. There’s also other people who have always had a side hustle. And so now that they’re nearing retirement, they decide to really lean in and to build it to a more substantial.

speaker-0 (05:03.022)
scale. Interesting. So is there a specific type of person that seems to lean towards this or is it seem to be right across the board?

speaker-1 (05:15.52)
It is, it’s right across the board. There’s a lot of debate, sometimes not productive debate, I think, in the entrepreneur world about, you know, when can you call yourself an entrepreneur versus somebody who’s maybe just has an idea and you make money yourself? My definition is if you are the one who is generating all your own revenue and nobody in you’re paying yourself, then you can call yourself an entrepreneur. It’s not just people who have.

a scalable business and tons of employees or those kinds of things. I just think we get a little bit too precious about that. A lot of people wanna know like, what are the characteristics that are gonna make somebody a great entrepreneur? And I have seen pretty much every configuration possible be successful and unsuccessful. So I’ve seen people with great sales skills and charisma and all the things fail.

sometimes because they didn’t have that product market fit. I’ve seen very quiet product focused people who just focus on a method or a model and they happen to maybe hit the right timing or they get the right partner and their business can totally take off. So it’s not so much about inherent characteristics about what is the type of person who can be successful. I think it seems like the most basic idea in the world, but you actually have to have an idea that is saleable.

You have to have market fit. You need to have something that people consider to be either something they want that’s an aspiration if it’s a product or if it’s a service that is a true need that they have that they’re willing to invest money in. And I think a lot of businesses fail because we just get too excited about our own idea and we don’t really put it through the rigor if it actually is something that should be out in the world.

and really has legs on it in terms of what we’re building. So I think that is something that’s a big part of the process. And then the other characteristics I see are people who are very open, willing to take feedback, and specifically willing to admit the areas of their own strengths and weaknesses.

speaker-1 (07:27.246)
so that they don’t spend all this time trying to do everything themselves, where they would either hire other people to partner with them or not just try to prove that they could be doing everything themselves. It’s kind of fascinating over the years that of, I think also the intersection of time, one can bring a business out at certain times. I started mine in 1996 in Silicon Valley.

which was a time of great growth for those of you who remember we were doing well economically. It was a really exciting time in Silicon Valley. HP, Hewlett Packard was my first client. I was working on building the global management development curriculum. And then just it was such an incredible time where people were growing, they were leaving companies, going other places. And so it was really, really easy to get work.

I could tell myself this story that I was this brilliant entrepreneur because from the second that I started working for myself, I made more than I did as an employee and I grew without any real marketing for 10 years. Most of it was just the timing and the place.

speaker-0 (08:37.224)
That’s the one thing, like, I’ll be honest, I’ve been in essence working for myself my entire life. I put myself through school, I had started a painting company and was used that to pay for my education. But I have found the vast majority of the things I’ve been doing were too early. Like I, my entire personality has always been about thinking ahead three to five years.

And I see something and I start working on it and it doesn’t take off. I’m going, why is it not taking off? And then, so I put it off to the side. And then two, three years later, somebody else’s takes off because it was the right timing.

speaker-1 (09:22.094)
That’s right. And there’s so many of those ingredients. so it’s just, there’s so much nuance to it that it can be very frustrating when you’ve seen that. I have kind of a similar way that I can like, I’ve just started to trust it. Now I wrote Escape from Cubicle Nation in 2009. And we had the great resignation in 2021. You know, I Body of Work in 2014. And then we had like the creator economy that happened, you know, years after it’s just funny sometimes where we can each

be wired to see something, but that market fit is just so specific. Like right now we see everybody, you your dentist is branding themselves as, know, dentist with AI, you know, like we can see certain things happening where everybody’s just throwing the latest thing. And there can be lots of money and investment happening there. But then what’s always interesting to me is noticing, I name it as more of a craftsperson approach where you really are thinking about

not just where is the latest opportunity to be chasing growth and where should I be investing? Some people are good at that, which is like, I’m happy for them. But it’s different when you really do care about leaning into an area that has opportunity, but where you really care about what you’re building. And especially you care about the person who’s buying from you. That to me is the most important thing. If you center them, then all the rest tends to fall easier in place.

speaker-0 (10:46.934)
I had that conversation yesterday with somebody where I was doing that pre, that introductory conversation that you and I had. Yeah. And they said, as long as you get what you want to hear. And it’s like, no, it’s not about me. It’s about the audience that I’m talking, trying to provide it. So keep in mind who my audience is. That sort of thing. So, yeah.

Talk to me about…

the retire, what happens when you get into retirement. Now, one of the things I think I’m starting to see, starting to see a, I won’t say trend, a trait is that people that are get up into this age range, they’re not so impatient. So they’re willing to last longer with something. When I was in my twenties, I’d start something. And if I didn’t see instant results,

It’s like, okay, it’s not going to work. put it to the side. Whereas sometimes I think if I had stayed with it just a little bit longer, it would have lasted. Whereas now, because I’m 61, my patience is longer. And I’m wondering whether that, I was told that the percentage of people in their retirement ages that start businesses, the success rate is that much higher. So I’m just wondering whether that’s a trait or that there’s a

change that happens.

speaker-1 (12:18.126)
Yeah, I think it’s relative. What’s so interesting right now is, you know, my day-to-day, to be fair, is talking with people who likely are entrepreneurs or they are, you know, experts in a certain field, whether university professors or, you know, somebody in corporate who kind of has a strong idea. So I know I don’t necessarily have the pulse on, you know, the

like overall trends of your average person maybe that’s been working in a company for a long time and is looking to retirement the way that maybe our parents or grandparents looked at retirement. And we’ve heard this, it’s like one of the whole reasons you have this great show is things are really changing for how long people are living and what they wanna do and where they get meaning and purpose and what retirement means. I know very few people who just want to…

get the retirement check and either hit the golf course or lay on a beach. And if that’s you, I’m actually thrilled for you. I have to encourage people to say, if you feel like that’s what you wanna do and you have saved for it, then go do that. Like we should be doing exactly what we want to do. There are just different dynamics at play. Some because of what it is that’s happened financially, some about for those folks who have kids.

the needs which can be different for ways in which folks our age can be investing or helping kids to get their first house or something because it’s not as easy for us. So some of the financial dynamics I think can be really different that can lead to different decisions about what we choose to invest in. like you said, having, you know, having lived a number of decades and seen things and looking at cycles of things I think is such a helpful lens. I just love

I’ve loved my 50s, I’m excited looking forward to my 60s because it’s really helpful to both be like excited about changes that are happening right now, but also having lived through so many things that just don’t really seem to change. I would always say you bring more than one person together and you have a dysfunctional organization. So as somebody who works with humans, like there’s an endless supply of work that’s out there. The part when we start to look at

speaker-1 (14:39.604)
at research around what can make a successful business. There are things, you know, like judgment that can come with age, but not necessarily. If you practice judgment, if you’ve been open and you learn things, then you can develop judgment with age. I’ve seen very young people who have really good judgment too. So it’s not necessarily tied to that, but so much about success, think is it is sticking with it. It’s not always looking for instant results, but it is also

choosing to be.

bringing forth things that actually do have market viability. And sometimes I see folks in that first category I was talking about who maybe always have had this desire to be starting a business. And maybe they haven’t really dialed in or they’re not familiar with what it takes. And there could be a little bit of magical thinking with it. Did you ever see Office Space? Are you familiar with that movie, right, folks? I think I’ve seen it. So it’s the jump to conclusions, Matt.

speaker-0 (15:34.168)
Yeah.

speaker-1 (15:40.494)
which was this great idea that the one employee at this company had. had this idea for a mat. And by definition, it’s not a very great business idea. He ended up bringing it forth after being hit by a truck and getting insurance money. But it is like, there’s plenty of that, which I’m always really cautious. I love to be encouraging the entrepreneurial spirit. I also think it’s

really important for people to be cautious about how they sink money into things. Sinking time, learning, building things all day, every day. Like that is such a great investment in your time, especially if you have more of it, but be extremely cautious about money that you are sinking into a business idea before you have really found that it’s viable. So I haven’t.

looked at some of the research that you’ve seen about those kind of elements of success as people get older. But I do think we just tend to be a bit more cautious. We’ve seen things, we understand things about partnerships, about human relationships that can be really helpful so that we’re not just looking for instant results.

speaker-0 (16:53.678)
That brings the entire conversation back to business risk and dealing with business risk. But keeping in mind that business isn’t just the one person and creating something. It’s not that old saying of create a better mousetrap and the world beats the path to your door. I don’t think that’s true because there it’s a relationship situation between you or whatever you’ve created and an external person. So that

means you also have to think about what the risk is of the other person. Now, if the other person is seeing an older person, somebody in retirement, what type of risks are they thinking about? I remember talking with Paul Tasner. He had trouble finding any sort of funding for a business that he had started up. He had started up the packaging for things like the iPhone, that sort of thing. But he had real trouble, not because of the concept of the business.

but because of his age.

speaker-1 (17:56.418)
Yeah. mean, I think, so you’re talking about what would be the risks for someone of our age or retirement age, you know, in. Yeah. So if that is our demographic, if that is our customer base, you know, that I think, you know, people are cautious as they should be about how they’re spending money and how they’re investing and, know, and so forth. Ageism is a real thing.

speaker-0 (18:05.666)
to be thinking about.

speaker-1 (18:23.022)
You know, we know that that is a real phenomenon. People are gonna have, you know, all kinds of different lenses of conscious or unconscious biases. And I think, especially because of AI and the advent of AI, depending on how, what our relationship has been with technology and innovation. And I also think what our circles look like, if we’ve had like multi-generational.

circles and I don’t mean just with our family, you again, for not everybody has kids, but for folks who have kids, you’re probably more used to, you know, talking to your kids, your kids’ friends, so you might be a little bit more tuned in, you know, to issues, concerns, kind of how people are thinking. But I also find professionally that if people, especially who are coming out of just purely being an employee and they’ve been somewhere for a long time, that there’s not always like multi-generational

professional groups and connections. And to me, that’s really an essential piece that if you’re only talking to people who are your age, and if we sometimes get, dare I say, a little bit grumpy or judgy about younger generations, there can be some unfair bias just the same way that we experience it. If people may not think that we have a capacity to be innovative, which I think we have endless capacity, but we can also be making judgments about a younger generation.

and have things like, you know, get upset if we do see somebody breaking through much more quickly or having success where there’s that, you know, well, wait a minute, you know, what I had to do is I had to grow this way. Or if there’s a high level of control with, see this dynamic a lot where there can be, you know, a seasoned expert that’s in a role. Very often their team is younger because they’re doing more highly technical operational things. And there often is not a real

collaborative approach and a really open and honest approach about different gifts and strengths that people can bring. And again, within different generations, it’s not just a function of age. Like somebody can have great judgment and be very young. Somebody can be extremely dynamic and innovative and be much older. My dad taught me this biggest lesson. I wrote about him in Body of Work. My dad was a photographer.

speaker-1 (20:42.83)
for Pacific Gas and Electric, the utility company in California, where I happen to be right now. I’m at my friends in Silicon Valley right now. I’m not at home in Arizona. But he loved the craft of photography. He just was old school. He had his black and white cameras in the early days. He was very innovative and shifting to digital technology. But he was such a relationship builder.

all the way through with everybody in the company. He was so respectful to everybody that he worked with. He would often go, maybe he’d do a shoot at a lineman school as they were learning things. And he would be taking pictures for the news publication or for the employee communications. And he would always take time to maybe do like a special kind of a portrait of that employee and then send them a copy so they could have one for their family. He was just constantly doing things like that.

And so when he turned 65, turned 65 in November, so he was eligible for retirement, they laid him off in December, the December after, you one month after he was eligible for retirement. But then they hired him as an independent contractor until he was 83. And I was like, dad, are you telling me that there aren’t massively capable 25 year old photographers in the San Francisco Bay area? But he was truly indispensable.

because he was so, he was as passionate about his craft and you know, at 83 as he was when he was 23 and he never took for granted about the quality of his work and then he was respectful and he had relationships with people who were really young in the workforce and then, you know, the senior executives of the company. And so for me, it was so important to see that because he,

never took for granted that people should just respect him because he had been around. I mean, he never would have been hired to come back. They would have been like, thank God we’ve moved that guy out and now we can bring in some fresh blood.

speaker-0 (22:40.235)
Let me rephrase what I heard with regards to your father, just so I understand here. Was his job at PG &E in photography or was it a different area? It was in photography.

speaker-1 (22:51.862)
Yeah, so he worked for the news. He worked in different departments, but corporate communications. He worked for the news department. So yeah, they have tens of thousands of employees all throughout the state. So he was taking pictures for the company. was a corporate photographer.

speaker-0 (23:06.082)
So he stayed with what he knew and probably, would hazard a guess, was core to his character. was core to his personality is he loved doing that and he loved creating that good quality product.

speaker-1 (23:22.548)
that that was the essence of who he was. I mean, it would just crack me up. He, you know, sent thousands of photos through the years and every time he would be nervous, like, you know, I hope they’re going to like it. Like he would have that just that feeling you get when you really care about the work that you’re doing. And I was like, Dad, has anybody ever not loved a picture? Never. But he just he took it so seriously. And I just and then he had this whole other side where he had a volunteer project where he they

bought a school in his small town and they restored it for 40 years as volunteers. And he, to me, was just an incredible role model for really living it to give it. But what I really took away from him is that it is not just a function of age. Ageism is real, and the research and the data proves that. But there’s a lot we can do to not be impacted by that as strongly.

by the way in which we do our work and the way that we build multi-generational relationships.

speaker-0 (24:25.942)
And that last part there is really the important thing because I can hear already people saying, I have this great idea. Yeah. But they don’t know how to sell it. But the problem is it’s not selling if you already have relationships you can build on.

speaker-1 (24:45.794)
That’s right. Yeah. It’s, mean, it is, you’re selling, you have so many more resources for people to be testing the idea, giving feedback. And again, like a big part of just being tuned into whether an idea is saleable or not is where it’s not just your pet project of which we all have our own favorite things.

but it’s more that it is something where like you just keep hearing over and over or you might have, know, whatever it is, you’ve created a product and everybody loves it, a certain kind of whatever, a wine opener or, you know, it’s like something that you do that everybody always gets excited by. was, I saw there was a interview, I think Gary Vaynerchuk, the startup guy who’s been around forever was talking to somebody who had, so was starting just with a side hustle, I think for organizing garages.

And so they were talking about it and he would go in, there was like a fixed flat fee for going into people’s garages, taking everything out, hauling everything off, cleaning, organizing it. And there was like, I don’t know, $600 flat fee or something like that. And then for things they took away that the person didn’t want, they would sell them and also get the money from that thing. And so as they were talking through that example, Gary was like,

that is the greatest idea ever. And you have incredible profit margins and like, just do more of that. He was like, your job ASAP because you’re proving out that model as something people are willing to pay for. We sometimes look for having this cool, sexy, know, tech enabled kind of idea. Sometimes it’s the most basic of things that you really do well and that you understand and that you just deeply get how you want to deliver it in a way that solves a big problem.

That can be a great business.

speaker-0 (26:37.966)
It’s interesting. What you’re talking about reminds me of a conversation I had or a lecture I went to back in the 80s when I was just new into entrepreneurship. And there’s a gentleman that had started up the removal of garbage from various different businesses, you know, with the big garbage trucks and that sort of stuff. Yeah. It has to happen. It doesn’t have to be some new app on your phone.

It can be just picking up the garbage. My cousin’s first wife, she had a business for cleaning houses. It doesn’t have to be glamorous, but she had a steady income coming in and it was something she was really good at. So it’s not like you have to go long and hard if it’s something that you’re doing already and you actually kind of enjoy it.

It’s something you can do moving forward.

speaker-1 (27:39.022)
That’s right. That’s right. Yeah. And you know, the best way to test it out is to test it out because anything like we were talking about earlier, you can have the most powerful idea, the business plan works out, all the metrics are pointing in the right direction. And yet it can absolutely fail spectacularly for a whole variety of reasons, know, wrong fit, wrong timing, all the things we’re talking about.

only way to really test the viability of an idea is to test it in the real world where you get people who are not related to you, who give you money, actually exchange money for a service, and then you just test and iterate around that. That is, I’m always looking as quickly as possible to how it is that you can get some kind of minimum viable product, MVP, as they call it, out there in the world. So if it is organizing garages or whatever your thing is,

then it would just, how could you in rapid succession do three of them and really notice what is the method that you’re using for doing that and what are people saying when they approach you? One thing I recommend is to these days, if you do use AI and you are having conversations with potential customers, if you’re just starting out.

If you, have Fathom, which is just a little plugin that works with Zoom. So it follows me around just like it tried to jump into this podcast interview before you kicked it out. But if you’re recording the conversations that you’re having with people, and so when they’re sharing and they approach you, they heard about you somehow, listen and record capture the exact words that they use to describe their problem, challenge or aspiration, because that is gold for you to be.

really harmonizing your marketing copy using the exact kinds of things that they are saying. Too often we try to put it in our understanding, which is we already have the expertise. We’re already looking ahead to what the solution is. And that’s often where we miss people. Back in the day, and when I first started my business, people would literally call me up and say, we need people training, you know, and say, okay, you know, great, tell me a little bit more, you know, what’s happening. And it could be everything from

speaker-1 (29:53.422)
We have no formal manager training for new managers or it could be There was actually a huge calamity because the sales manager was you terrible and running everybody off and because they avoided conflict Instead of dealing with that one person performance issue. They decided to train everybody else You know, there could be a million ways in which it I ended up diagnosing what the real problem was but when you use and harmonize the language that people actually use

to describe their problem in their words, those are the kinds of ways that you want to start connecting with people. And that’s one area I find that a lot of people just miss and then people don’t resonate.

speaker-0 (30:36.778)
Do you see older people having different issues from, say, that 20-year-old with the starting up of the business? Or are the issues the same regardless of the age?

speaker-1 (30:53.454)
Some of it is the age, some of it’s the experience or specific expertise. I feel like it’s a little bit of a stereotype that older folks are not as good with technology. We know a lot of people, especially if you’ve grown up in tech, that folks our age might be really comfortable with technology. But as we look at a generational difference about kids that are being raised with phone in their hands, where if it’s everything from just

posting on social media and being very comfortable to just like being used to working with apps or computers more. That can be one area where I do see probably a bigger percentage of people that are our age that are stumbling with like defining the right tech stack and getting everything rolling and getting frustrated when things don’t work right or taking more time than is necessary to be dialing in all of the

what they consider the business fundamentals. So we need to have the perfect logo. We need to have everything just right. I find a lot of younger folks are much more comfortable just trying things and experimenting, but not always. Like some of it is just experience somebody has or how they’re wired.

speaker-0 (32:09.518)
also flipped out on its head in that yes the younger people are good with technology but they’re not nearly as good with talking to people and creating those relationships.

speaker-1 (32:22.762)
Absolutely. And I think that’s one area where the generations can be so helpful to each other. I’m staying with my friends, John and Bonnie, who I’ve actually known for 30 years. So when I first started consulting here in Silicon Valley, John worked at 3Com, which was my second company that I worked for. So we’ve known each other for three decades. We were just talking about that a few minutes ago.

And we were just saying, like, especially in the age of, you he’s been all deep in the world of tech down here for many decades. But like in the world of AI, there is nothing like really having long term trusting relationships with people who you can count on, who can be, you know, using discernment, who can be giving perspective. When I think about, you know, innovative things that can happen.

in ideas that come from deep conversation and looking at things in different angles and all of that, or being comfortable walking up to people and talking to them, sitting next to somebody on a plane and talking to them. Some of those things really can be where you’ve been in business that has been so relationship-filled. I’m finding a lot of people are hungering to be either going back to that or realizing what a critical skill that is today when so many other functions have really been automated.

I’ve done a lot of coaching with my kids around that because you’re right, especially my kids happen to spend some of their high school years during the COVID times, doing remote school and all of that, that it’ll be fascinating to see, I think, the studies afterwards of the ways that that impacted, maybe natural ways that they would have been building relationships in school. But sometimes it’s pretty fundamental.

What do I say if I go down and I have a job interview? How do I actually start it? Or what if they ask me a question that I don’t have the answer to? But I’ve heard that same thing from people who are 65. It just depends on what your experience is and what kind of role that you played.

speaker-0 (34:34.51)
And if you’ve been in the cubicle all your life and then all of sudden you’re on your own and it’s like, okay, now I actually have to try and talk people into it. You’re trying to sell as opposed to trying to help.

speaker-1 (34:47.566)
Well, that could, if you’re thinking about it that way, that’s probably going to mess you up as opposed to saying it’s actually the same thing. It’s about building relationships. It’s about, you know, understanding organizational dynamics. It’s about navigating through, you know, complex situations, but it is, like there, there’s an art to sales. And I think there’s it like, it’s a, it’s a craft that’s really worth doing well. Like I don’t look at selling as a, as a negative thing, but

the underlying ingredient to effective sales is trust. And that’s because you do feel good if you’re selling something, that’s where you have to feel good about what it is that you’re selling. When you’re early in the journey, that’s where you have to lean on sometimes your trust in yourself and your ability to make pivots. Because if you’re newly doing something,

on your own, then you don’t really have the proof of saying that you’ve worked with 10 other companies to do this project. One of the things that I remember saying early on when I started Escape from Cubicle Nation, so I had started doing that coaching of people leaving corporate, my grand experience was one person and that was me. So the first people I worked with, I had done lots of work with organizations, but I had not done that work with other people. And so my mantra always became like,

you know what, that’s a great question, I don’t know, but I’ll find out. And I just, that was how I actually built a huge network of other experts is by being relentless about finding out how I could help my clients solve their problems and not pretending to know because that is wildly irresponsible if I’m pretending to know something that has such a big impact on their livelihood.

speaker-0 (36:34.766)
Coming from the IT environment, if I was to try and excuse my language, bullshit somebody, I’d be called out on it very quickly. I would actually have to know my stuff to be able to talk with people and that’s often going to happen. But that also brings up another aspect is that us techies are, I have said this for decades, we are social morons.

Her ability to talk with people are is off. The reason why we tend to go towards the technology side of things is because that way we don’t have to talk to people. We’re avoiding that harder aspect. So it becomes.

Once you retire, if you don’t have those relationships that come about as a result of being at work, you have to learn to go out and have those relationships. So that becomes a little bit harder when you get to that age.

speaker-1 (37:34.218)
It can, and I think part of that depends on what kind of wingspan of connections that you want. There are in the range of folks who are highly technical, like you said, there are some people who’s like their passion and their interest really is in doing their work and understanding technology. And it’s not that they dislike people, but it’s just like there’s not a huge

shot of dopamine, you know, when they’re interacting with people. And so they, and there’s a lot of ways that people can connect online. I actually find I’ve never been a gamer myself. My kids, you know, grew up gaming, but gaming is one area I think where you can be leveraging the skill of being a technical person. find a lot of folks do develop friendships and fun, you know, collaboration and competition through people that they meet or through I’m a star Wars nerd myself. So

You know, people might go to, you know, Comic-Con or like follow like specific kind of cool nerdy endeavors where they can have specific interests in, you know, cultural or artistic or things like that where they can be connecting. But it is, yeah.

speaker-0 (38:45.752)
That’s a really good point is because people tend to, they do have their groups that they’re part of. They may not realize they’re part of these groups. So things like the Comic Cons, the going up to get your coffees on a regular day and seeing the same people at the coffee shop. I said this earlier in some of my early interviews, because I’m at home,

I’ve been at home, God, since 2004, simply because that’s the nature of what I’ve done. I intentionally every day go food shopping and I see everybody at the same time and I’m saying, I know them by the names and I have my group there. So you end up having your groups that you can leverage even after you’ve retired.

speaker-1 (39:40.424)
That’s true. mean, and it’s, you know, it’s like when you think about that size of connection or the type of people who you’re interested in connecting with. I did a big project with Susan Cain who wrote the book Quiet about the power of introverts. So I learned I’m an extrovert myself, but my whole family are introverts, mom, dad, sister, brother, my ex-husband, my two kids. So I’m very comfortable with introverts and I am an extrovert myself, but there’s

there definitely are people who like much deeper, more meaningful conversation with fewer people. So maybe there’s a much smaller friend group or folks who really enjoy, you know, deep conversation, even with a stranger, but where you’re able to have more than just the surface level conversation. So there’s some of it, which is just understanding for you what is the size of a community that you want to have. But then it is also realizing that there

is I think a fundamental need for connection. And sometimes all of us can hide a bit behind, know, I just, you I don’t like people or I don’t wanna be connecting where I’ve always had a really great relationship maybe because I’m an extrovert and I’ve always dealt on the human side of business when I did so much work in Silicon Valley. At first I was terrified of ever presenting anything in front of engineers and tech people because as you said, they have zero tolerance for BS.

So I learned really quickly to never make anything up, but to also come with a strong prepared perspective in what I was teaching. But I also developed lots of very deep friendships with people who came from that perspective who are funny and interesting. we can have stereotypes, I think, on either side. They might judge salespeople or marketers or HR people as being people of no substance whatsoever.

And then we can look at other folks as having no human connections and capabilities. But I think we all can learn a little bit more from each other. But one thing I’m just noticing overall is people really are hungry for human connections and just, yeah, knowing your neighbors. I really invest a lot of energy in that. I make sure I really know my neighbors.

speaker-0 (41:58.506)
It’s interesting when you said about different people, it triggered a thought. The reason why I wear golf shirts all the time is simply because if I was wearing a suit and I went into a tech environment, they’d ignore me because they wouldn’t think I knew what I’m talking about. Right. So I ended up dressing down just to deal with the people I had to deal with and being seamless with that.

Are there, you mentioned that technology are areas that are harder for people that are older simply because they didn’t grow up with those technologies, that sort of thing. What about things like obtaining financing and funding and that sort of stuff? Is there more of a hesitancy on people that are giving out funds, bank loans, that sort of stuff, if somebody is older? Maybe because maybe there’s health, potential health issues?

Maybe because there’s a perception, hey, this person’s older, he’s slowing down. Is there?

speaker-1 (43:01.562)
I mean, I would say on the VC side, if you’re ever trying to get any, you know, angel funding or venture funding, that there can be more of a bias sometimes. It does depend on the idea. So a lot of it is what’s the idea? What’s the proof of an idea? The thing about funding is that in general, if banks are being responsible and investors are being responsible, they’re never, rarely ever investing at the first stage of the journey.

What your job is is to prove the viability of the idea with your own investment in real time where you’re proving that either you are really increasing the number of users, followers to your thing, but the bank is not going to be investing in potential. on one hand that I find sometimes people have a…

skewed understanding about like, I’m going to start a business and I’m going to be getting, you know, a lot of funding for it. When very often they’re like, you may look more attractive because you do have assets yourself that they can be using as leverage. And so there’s less risk, but of course you can put some of those assets at risk if you’re not careful, right? Based on your business investment. But it’s very often that what they’re going to look at, if you’re getting financing for your business is,

going to look at the track record and they want to see increasing revenue but also increasing profit. And another area I think where a lot of people get stuck because who loves paying taxes? I’m actually a weirdo. I like paying taxes because I love firefighters and teachers and potholes filled. You should come up to I don’t appreciate the way they’re being used for the worm machine or whatever, but it’s like don’t.

mind as long as we feel like they’re generally being used. But a lot of people, they’ll run their business finances like they’re thinking about for their personal finances and taxes. So they might try to get as many write-offs as possible. What the bank will then see is, well, you brought in this amount of revenue, but you only had this amount of profit because you’re optimizing for tax benefit, personal tax benefit. Whereas if you’re really trying to get financing,

speaker-1 (45:17.71)
you’re trying to show that business has profitability long-term. So there’s a lot of factors that can be addressed. It also goes back to relationship. A lot of times smaller credit unions, smaller banks, community banks still have a dynamic like the old days of really having a personal relationship with a banker, like your own community standing, the way people know you and make a difference in terms of what they’re willing to extend.

But I find early on for financing, then people can be doing things like getting a business line of credit, you know, as opposed to like getting a loan. Cause that can be quite, it can be quite complicated. I mean, a lot of clients do get like an SBA loan and things like that, but just know that you have to be proving that you have actually generated the revenue to be proving the business model, usually before anybody’s going to invest with you.

speaker-0 (46:13.422)
for everybody not in the US and the SBA is small business agency or advisor.

speaker-1 (46:19.092)
Association. Yeah, thanks for the clarification.

speaker-0 (46:21.774)
Small Business Association, basically is a federal agency. I’ll use the term grant though it’s not a grant because it has to be paid back. That sort of thing.

speaker-1 (46:30.232)
Yeah. So low interest loan, you know, intended to stimulate the, you know, economy and entrepreneurship by extending it for, for small business owners. Yeah.

speaker-0 (46:41.048)
Being in Canada, I can’t tell you how many times over the decades I’m reading up stuff, but I’m dealing from an American point of view and then I have to translate it.

speaker-1 (46:52.487)
I appreciate that. should know better because I have so many Canadian clients. So you’re right.

speaker-0 (46:56.802)
It was like a 401k. It’s like, okay, that’s an American specific term type thing. Yes. But no, you said something very important and I’m going to reiterate it here for the audience more for you than for yourself. A lot of people tend to, and I, I, I to this day still do. So it’s something that I catch myself. I’m put the cart before the horse. I’m looking for the funding before.

the business is there, as opposed to the business is proving that it deserves to have the funding. So that’s the one thing is if you have a business that you have in mind, but you can’t get it running without cash, you’re going to have trouble. Whereas if you can figure out a business concept that you can get sales for, show that then you can get the funding.

speaker-1 (47:30.637)
Yes.

speaker-1 (47:53.516)
Yes.

speaker-0 (47:54.306)
So one of the things, because this podcast is new, it’s the same thing from a sales point of view. Getting sponsors to sponsor this podcast, they want to see viewership numbers, which is great for this podcast because it’s just taken off like you wouldn’t believe. But to get a sponsor, I need to have the views beforehand.

speaker-1 (48:18.285)
Yes.

It’s a very chicken egg kind of thing where it’s the frustrating part, but it also can be a very focusing part because one can run off in 32 different directions of all the things you need to do in business. And the main thing that you need to be focusing on is in getting real people in the real world to pay real money for your thing and then to keep improving and iterating and growing that.

and it’s very easy to get distracted in a whole bunch of other areas of business. And it’s not going to be moving the business forward and it won’t be attracting opportunities like you said for investment or financing.

speaker-0 (49:02.766)
Yeah, so you think in terms of a spiral, small at first and then it slowly keeps getting bigger and bigger until when it’s big enough, it’ll start getting a life of its own, which is when that funding comes in or those bigger customers come in.

speaker-1 (49:20.406)
Or that’s It could be. Yeah. And then just like you’re finding, I’m so excited that you’ve had such rapid adoption, you know, sort of it, it validates right in your small way of just the fact that so many people are age or so hungry for all kinds of great information, because we’re just opening up this whole new chapter, in our life. But it, you know, it is, yeah, it is something I think that’s, that’s really important to recognize that the, can have the best idea in the world.

You can have a track record of sales. What will get you often the investment and growth and all of that and funding from a bank or from an investor is relationship and story.

speaker-0 (50:05.196)
That relationship is really important because you don’t necessarily get a no. Make sure you hear what’s being said, because it may not be a no, it may be a not right now.

speaker-1 (50:19.128)
That’s right.

speaker-0 (50:20.682)
So you have to have the patience, which because we’re older, our patience is a little bit better so we can last a little bit longer for when that does come.

speaker-1 (50:28.844)
That’s right. That’s right. But the story you tell and the way that you paint the picture and the way that you help people understand what the potential is, that is a huge part of the journey as well. It’s, it’s why entrepreneurship is so hard because you really have to nail a whole bunch of different parts, but that’s what makes it worthwhile too. It’s a never ending personal and professional development journey.

speaker-0 (50:57.122)
Well, Pamela, we’re getting close to the end of the interview itself. I always ask all my guests one last question. If you had one piece of advice, and you’ve already thrown out a lot of different pieces of advice, but if you had one piece of advice you would tell everybody, and it could be something that you’ve already said today, what would that one piece of advice be?

speaker-1 (51:19.532)
It would be to build your business on who you actually are. Really, really deeply understand yourself and how you’re wired and your skills and your strengths. Because for you to have that accurate understanding as a founder, that’s part of the criteria that you’re gonna use for which of the different business ideas that you want.

I’ve said before that in order for a business to be viable, it has to meet a need in the market. You have to have the right timing. You have to have all these other things, but very often people are aspiring to be somebody else. And there is always going to be powerful things about the way that you’re naturally wired and your skills and your strengths that will help you to be creating a business that you’re actually going to enjoy running. And you know, it’s, it’s not,

easy to make money if it were, know, you and I would be rich, would just tell people the secret formula. But in many ways, it’s much easier just to like have a money making idea than it is to enjoy what it is that you’re doing while making money. And to me, that’s always the criteria for a good quality of life, especially as we look at this next chapter, is not just doing things for money. For many people, they have that

you know, or at least a good percentage of that locked in, in terms of just what they need to take care of the next chapter of their life. So it should be about quality of life and quality of your body of work. And just to really stay in the lane of knowing yourself is, I think, the most important thing that you can do.

speaker-0 (53:05.762)
I have a quote here from Viktor Frankl, Viktor Frankl on my wall here, philosopher from a while back. And one of the things he said, to paraphrase it, is don’t chase success. Success will come as a result of focusing on something that’s outside of yourself.

So don’t chase the money. making a, doing great photography like your father. And everything else will come.

speaker-1 (53:43.35)
Absolutely.

speaker-0 (53:45.41)
Pamela I really appreciate you coming for everybody. I will put the Information about Pamela and her agency in the description Any other things that Pamela comes up with that she’d like you to be aware of as well I will put in the description for this video And don’t forget to click like and subscribe So YouTube actually gets people to come and watch this. Pamela. Thank you very much for your time

speaker-1 (54:15.64)
Thanks for having me.