Episode #85:
Don’t Let a Disability (or Anything Else) Stop You From Doing Your Entrepreneurial Thing
with Rob Oliver

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Rob Oliver, speaker, podcaster, author, husband, and dad, is inspirational and super special. You know this because he is one of only a handful of guys to be featured on the Expand Your Fempire podcast! Don’t miss this unique episode where Rob shares his entrepreneurial journey, his work in the disability community, and the different effects that entrepreneurship and working a J.O.B. can have on mental health. Plus, hear his top guiding principles for those looking to start a business.


I am a speaker, Podcaster, author, husband, dad, and all-around nice guy. As a speaker, I talked to medical professionals about quality healthcare and to audiences in general about resilience. I have two podcasts, one for entrepreneurs (Learning from Smart People) and another for the medical community (Perspectives on Healthcare.) My wife and I have been married for 27 years and are the proud parents of 20-year-old triplets (a boy and 2 girls.) I love to learn and to share my knowledge with others. On a side note, I aim to be a world record holder within the next two months and I am a person with a disability. – Rob Oliver

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Expand Your Fempire Podcast #85 Transcript


Don’t Let a Disability (or Anything Else) Stop You From Doing Your Entrepreneurial Thing
with Rob Oliver

Welcome to Expand your Fempire with Caterina Rando, the podcast for women in business on a mission. Sharing ideas to support you to grow and thrive. Now here’s your host, Caterina Rando.

[00:00:00] Caterina Rando: This is Caterina Rando, and I am blissing to be with you again today for another episode of the Expand Your Fempire podcast. Now, today we have a very special guest. Now, you know he’s special because it’s a he, and you gotta be extra, extra, extra something special when you’re a guy to be on the Expand Your Fempire Podcast. Rob Oliver is one of those few guys. You’re going to want to be present for this podcast today. We are going to give you some thought-provoking ideas to think about. You’re going to leave more uplifted and inspired than when you showed up, and hopefully gain some great insights to support you in your business and your life. Rob, so happy to have you with us today.

[00:01:20] Rob Oliver: It is my privilege to be here and to be one of the few guys that makes it to be here. What an honor, so thank you so much for having me.

[00:01:30] Caterina Rando: Rob, I think you’re number three and we’re on about episode 86. So you’re something special.

[00:01:37] Rob Oliver: I’m honored.

[00:01:38] Caterina Rando: Good. Okay. Here’s the thing, Rob. You are a keynote speaker, you have two podcasts, you have a consulting company, you have a nonprofit, so clearly you are not somebody who, you know, doesn’t do much. And that’s great because we’re all about being in action around here. Let’s start though, Rob, I want to hear a little bit about your entrepreneurial journey, because we all get here in a different way.

[00:02:08] Rob Oliver: Sure, so I guess I’ll start this way. My entrepreneurial journey actually started when I was still in college, when I was 21 years old, still going to school, and I was body surfing on the outer banks of North Carolina over summer break. And I ended up in an injury where I broke my neck. And so I’m paralyzed from the chest down with limited use of my arms and hands. And that’s been my story for the last 28 years or so. So that’s really the beginning of my entrepreneurial journey. I’m in college and I graduate with my bachelor’s degree in psychology. I went from being a psychology major to a psychology major with purpose, because now I could really see the impact of what that training was doing. I got out and I tried to get a job. And I applied to a ton of different places, and nobody got back to me. I couldn’t find a job to save my life. So I thought maybe I don’t have the credentials that I need. So I went back and I got my master’s degree in psychology. And again, going out into the world, trying to find a job, it was really weird because my experience as a person, without a disability was this: I applied for two different jobs before I acquired my disability, and in both of them I was hired on the spot and asked to start the next day. Okay. That was how things went. Now, after my disability, I’m applying for jobs and I’m just not hearing anything back. And eventually, I connected with somebody who was in the disability services industry. They said, “there’s an opening at one of the companies that I know of, let me connect you there”. I went in and I interviewed and they were like “we love you. We want to hire you. Can you start like tomorrow?” And it was that same feeling like, “okay, they value me, they see me for who I am,” and what I came to realize, it’s kind of a double-edged sword. It’s really hard for people with disabilities to find employment in the first place. But now at least there is a segment where they are valued. In the disability services industry, there is value for people with disabilities because they’ve been through the experiences, they have the peer understanding. And what I mean by disability services is home and community-based services or attendant care or assistive technology, just so many occupations like that where you’re supporting people with disabilities and helping them to live independently within the community. And I was there for a little while. I ended up moving positions, started with the disability rights network of Pennsylvania, which is, here’s a little educational nugget for everyone, it’s what’s known as a P and A organization, which stands for protection and advocacy. And every single state and every single territory in the United States has a P and A, a protection and advocacy organization, that is they’re funded by the government to ensure that people with disabilities are not being discriminated against and that they’re receiving the goods and services to which they’re entitled. It is both its protection and advocacy. There are advocates that are working there that will talk to people about what’s going on in their life. And there are also attorneys who are there, if things don’t go as they’re supposed to, we can use the legal system to affect the remedies that we’re looking for. Okay.

[00:05:47] So in all of that, what I find is in the disability world, they love me. But when I’m trying to get a job anywhere else, I just can’t make it happen. When I come in, they see the wheelchair. I don’t know what it is that they’re seeing, but they’re not seeing me. I feel like I’m a reasonably articulate guy. I feel like I’m intelligent enough. I’m funny. If I was looking for a person to hire, I would hire me, but there’s something missing in there. And so I had been doing a lot of speaking on the side and was thinking, ” I’d like to go do this full-time, but I’m scared”. Like you walk away from a full-time job to something that’s not quite a hundred percent certain. And in that I’m working and kind of doing both things. And then, my organization decides, “you know, we’re too big and we need to do some layoffs, and we’re looking for layoff volunteers. And we’ll give you a severance package and the whole thing”. And I came home, I talked to my wife and I said “you know, I think this is divine Providence opening up the door to say ‘okay, now’s the time to go. I’ve given you everything you’ve got.'” And so, that was three years ago I decided.

[00:07:08] Caterina Rando: Congratulations!

[00:07:09] Rob Oliver: Thank you. I’m moving out. I’m going to go and do it, do my own thing, and be my own boss.

[00:07:17] Caterina Rando: Rob. I didn’t know that you’ve only been in your own business for three years because you’ve had the kindness of having me on your podcast and when I look at your CV and everything, you’re doing so many amazing things. I would have thought you’ve been in business for 15, 20 years. Again, clearly, you’re a man of action. That’s wonderful. I want to ask you a couple of questions if I can, as we hang out here before we continue. What did you not know that you needed to know as an entrepreneur, meaning what was it that you realized “oh, well, I didn’t have to worry about this one, I had a job, now I’m doing my own thing”? Of course, you’re still bringing your massive value, but what did you have to learn to be an entrepreneur?

[00:08:06] Rob Oliver: This is really, I think a key point to me. I have a passion for speaking. I have a skill set that translates, when I’m in front of an audience I’m able to move them emotionally, I’m able to educate them on a topic, and I’m able to hopefully motivate them to change something about their life as they leave that auditorium. Right? That’s a skill set that I have and the passion of. What I didn’t really think about was this is a business. Okay. And as such, because it’s a business, passion and skill and all of those things, those elements, nobody ever taught me that. And I didn’t really think through the concept of what does it mean to run your own business, as opposed to being your own boss. There’s a huge difference to me in those two concepts.

[00:09:07] Caterina Rando: And so did you realize, well now you don’t just get to go speak more. Now you’ve also got to get paid. You’ve got to manage the business. I like to say that we have five jobs as the CEOs, speaking, selling, serving our clients, strategy for the business, and of course self-care. And that’s a lot of jobs. And then some entrepreneurs are also doing the bookkeeping and the admin and the 50 other things. So what did you realize that you had to take off your plate or get support around, or new skills you had to learn?

[00:09:44] Rob Oliver: So this is actually the reason that I started my first podcast. Let me back up just a little bit. One of the things that I did was I connected with the national speakers association chapter here in Pittsburgh. And, I think they were really helpful to me from the idea of they’re not teaching me about stage presence, they’re teaching me about the nuts and bolts of running a speaking business. And that was hugely valuable to me. And then my first podcast that I started was called Learning From Smart People. And it’s targeted at entrepreneurs. The idea behind it was this: what is it that entrepreneurs need to learn and who are the people that we can learn from to gain new skills, gain new understanding, to help us run our businesses better. It was very selfish in that I started a podcast to say, “what experts can I bring in that are going to help me with my business? And if they’re helping me with my business, they’re going to help the rest of the entrepreneurs out there with their business”. So, you know, talking about marketing and talking about business systems and talking about strategies, talking about scaling your business, talking about growing your business, talking about, you know, PR and branding and all of these different elements. And that was really something where I thought “I’m able to bring in other experts and I’m able to learn from them so that I can improve and that I can build my business in a better way”. And really for me, the issue was my business is small, it’s not growing. I mean, COVID took a big giant dookie right on top of the speaking business. Pardon my frankness on that, but it did. Right? So in that, I’m trying to figure out how do I bring in experts? How can I do it in a cost-effective manner? You know, my goal is to have the business grow to the point where I’m able to share responsibility, I’m able to delegate a lot more. But in the beginning, really what I’m learning is this is me, it’s my deal, it’s my thing. And I’ve got to educate myself as much as possible in all of the areas so that this is a successful business and it’s being run as well as possible.

[00:11:53] Caterina Rando: Well, I love Rob that you said “Hey, I need to learn some stuff. Let me start a podcast and have the experts come on that I want to teach me some stuff”. That’s wonderful. Now you, again, we said you got a lot on your plate. That is one of your podcasts, you have two podcasts, and this is an area where you do a lot of your speaking. Why don’t you take a moment to let our listeners know about that as well?

[00:12:17] Rob Oliver: Sure. Like I said, the first podcast is called Learning From Smart People. You can find at learningfromsmartpeople.com. The other one is called Perspectives On Healthcare. Also perspectivesonhealthcare.com. It is geared for anyone who is interested in the medical community. On that one, one of my main topics being a speaker is quality healthcare and a patient’s perspective on healthcare and really talking about patient and family-centered care. That is a passion of mine. It’s something that I think because of my vast medical experiences, I know more than I want to know more than I ever intended to, but I like to take that and say, all right, how can I share the knowledge that I have so that I’m improving the patient experience for everyone who comes behind me? With Perspectives On Healthcare, I have been interviewing members of the medical community to have them talk a little bit about their role in healthcare, talk about what quality healthcare means to them, and then talk about a little bit about the future of healthcare and how to improve it. Now I do have a super exciting announcement about this. Okay. So here’s, here’s what I’m doing: on May 6th and 7th of this year, 2022, I am going to be trying to set a Guinness World Record for the longest interview marathon. And for those two days, I’m going for 36+ straight hours of interviews with patients to hear their stories and to hear their viewpoint on quality health care. Because I think the patient voice is one that needs to be heard. And I also feel like without patients, the healthcare system doesn’t exist. They are the sole reason that there are medical practitioners. And so as a result, we’ve got to hear what they have to say, and we’ve got to share their stories and share what is working for them and what’s not working for them. And how do we make this a system that works for all of us? So that’s the other podcast and I’m super excited about that, lining up patients to talk to. And it’s a very, very cool and fun venture that I’m heading into. You can check it out, perspectivesonhealthcare.com/record, and all the information about it will be on there and give you everything you need to know, but it’s going to be cool, cause what we’re doing is getting the patient’s perspective. That’s what I think is most important for medical professionals to hear because they’re the reason why the healthcare practice exists at all.

[00:14:51] Caterina Rando: First of all, I love that you’re doing that. I also love that you’re going for breaking a Guinness Book World Record. You don’t do anything little, and I like that too. Rob, one of the things I want to ask you, because over my time, I have met many people over the years with disabilities, wanting to start businesses, having a business. And I would like to hear from you, what are your thoughts for someone with a disability, starting a business, and maybe a little advice for them.

[00:15:26] Rob Oliver: My advice is go for it. And I don’t want to be trite with that. Because here’s what I understand that for people with disabilities, there are a lot of things to consider. Number one, healthcare is always an issue, health insurance, all of those things. Be very careful with that. I know here in the state of Pennsylvania, there is a program called Medical Assistance for Workers with Disabilities, where you’re able to still keep your Medicaid benefits while you’re working. There are any number of different programs out there to support people with disabilities to become entrepreneurs. Here’s the reason why I feel like entrepreneurship really is an important tool for individuals with disabilities. And that is people don’t believe in us a lot of times. Stigma and bias exists, and people are not as willing to give us a chance. They look at us and they see our limitations. I think on the other hand, it’s really important to look at us from the other perspective. To say “what are my abilities and how do I maximize those abilities?” One of my favorite quotes is this: “nobody ever achieved greatness by focusing on what they can’t do”. Right? So to me, this is what kind of got my mind thinking about setting a Guinness world record. I thought I would love to do something on a world stage like that. But I thought, well what can I do? Like I can’t throw, I’m not going to be the most Frisbee tosses in a minute. I’m not going to be a lot of those different physical type of things. But if you look for an area where you can utilize your skill set, you can utilize the abilities that you have, utilize the skills that you’ve learned, just because you can’t do everything doesn’t mean that you can’t excel at the things that you can do. And the next step for me in that is now you are really in charge of your own life. You are making your own decisions. And instead of being beholden to the system where you’re working, you know, in a nonprofit, you’re working with limited earning potential, you’re in a place where your potential is literally limited only by your own resourcefulness and determination.

[00:17:46] Caterina Rando: Rob. I like to say that when you have your own business, you’re living in the light because you get to be yourself, you get to do your thing, you get to serve your people, and yes, you control your earning, or at least you have the ability to control your earning. Would you agree with that?

[00:18:06] Rob Oliver: Absolutely. What is the difference between darkness and light? You cannot create darkness. The only way to create darkness is to remove light. And so what we all need, the battle against darkness is walk in the light, be in the light, enjoy the light, soak up the light, be the light, right? That’s the battle against darkness. When you’re doing that, darkness doesn’t stand a chance.

[00:18:27] Caterina Rando: That’s beautiful. You know, Rob, I want to ask you this question. One of the things during the pandemic that has been a topic of conversation more is mental health. And I want to ask you, as someone who is an entrepreneur now, who used to have a job, I want to ask you if your mental health is different or better compared to before. I’m curious if entrepreneurship is good for mental health. I don’t have any, you know, study on that and I know it’s anecdotal, our conversation. But I would like your perspective on that.

[00:19:04] Rob Oliver: Sure. Let me back up a little bit and I’ll tell you. People with disabilities have a higher incidence of depression. Okay. And a lot of people would look at that data and say, obviously they do, because they’ve got more problems in life. They’ve got bigger issues. And the research has found that’s not actually the case. The issue, the reason why people with disabilities tend to battle depression more often comes from isolation, where they are in their home, they’re not getting into the community, they’re not having a lot of interactions. The only people that they are experiencing in their world are often either direct family members or staff that is paid to spend time with them. They’re not forming the friendships or not being part of the community. And so there is the beginning element of that when it comes to having a disability. I will also tell you that for me, I try and be a positive person, but once or twice a year, I crash. And I’m like this, this sucks. This is really hard. And you know what’s going to happen. I’m going to wake up tomorrow and it’s going to be the same thing tomorrow as it is today. It’s not going to get better. It’s not going to get easier. And in many ways there are very few people that truly understand what I go through on a daily basis. It’s a very lonely place to be. And my wife who is amazing, basically says to me like “look around you, look at your world and you tell me what you’re missing”. Right? Got a wife who loves you. You got three amazing kids. You work. You’ve got friends. You’re active in church. All of these things that you have going for you. Talk to me about what your life is missing, and talk to me about what it is that you really need to be down about”. And when you put it all in perspective like that, it’s like “okay, I’m doing pretty well actually. I’m okay”. But to bring it into this, I feel like COVID has been difficult on all of us because all of us have had that alone feeling. All of us have had that isolated experience. And especially for people with disabilities, the limited amount of community experience that they were having has been downsized drastically. And now you’re spending a lot more time alone, a lot more time with just staff. And to me, I think that really as many interactions as people can have, as many relationships as can be built, those are the elements that are going to battle that loneliness and that feeling of isolation. And I’ll tell you just real quickly, one of my tricks and tips for this is when I start looking inward and I start feeling bad for myself, the first thing that I do is I think “okay, who else out there is suffering? Who else out there is having a difficult time? How do I reach out to them? How do I encourage them? How do I serve them?” And instead of being consumed with my own issues, it’s how can I use my abilities to make somebody else’s life better? And when I do that, there is a definite feeling of value that comes with it. There is an improved relationship, and there’s an understanding that, you know what, I may not have it all going on, but the things that I do have going on are things that I can use to make other people’s lives better. And that’s really what life’s all about.

[00:22:33] Caterina Rando: That’s beautiful, Rob. And you know, that is actually what the studies show, that when you help other people, it lifts you up. That when we stay and think about our own “sorry for me” situation, and we stay there, it doesn’t get better. When we go out and help people that that makes a difference. Volunteers are actually the happiest people on the planet, it’s not about wealth or even having a partner, it’s about being of service that lifts people up. That’s beautiful. Well, Rob, I still want to hear the answer to your question about the entrepreneurship versus job.

[00:23:17] Rob Oliver: I am working more hours now being an entrepreneur than I was when I had a job. Okay. I am dealing with more frustrations than I was when I had a job. I’m realizing more and more areas that I don’t really have all the information that I need but I wouldn’t trade what I’m doing for a job for, I’m not going to say all the money in the world, cause if someone would pay me all the money in the world to work for them, I’d consider it. But anything less than that, you can’t hire me.

[00:23:54] Caterina Rando: That’s beautiful. I love that. That’s great. Okay. So would you say it’s better for your mental health?

[00:23:59] Rob Oliver: I would say that there are days when it is more challenging. There are days when I am a little bit more anxious, a little bit more concerned, but those days spur me on to be more engaged in my business, and they give me opportunities to say “okay, I’m concerned about this. What do I do to address it?” Because when you’re working for somebody else and you have those anxiety feelings, it’s on them, that you have a boss, you have somebody above you. But when it’s you thinking about “okay, this is my business”. You’re the one that is empowered to say, ” I’m going to make a difference about this. I’m going to take this worry off of my plate by addressing it in this way”. It’s really an empowering thing. And are there times when it can be extremely difficult you know, on my mental health? Yes. But is it far more rewarding? Absolutely.

[00:24:54] Caterina Rando: Beautiful Rob. Well, that’s how I hope all entrepreneurs feel. Before we begin to wrap up, Rob, one other thing we want to talk about is you have started a nonprofit with your business, or maybe I made an assumption there. You’ve started a nonprofit. I’m all about encouraging entrepreneurs to infuse philanthropy through their business. I’d like to hear about what you’re doing, and do you do that as a private citizen, or do you infuse that in your business?

[00:25:24] Rob Oliver: So thank you so much for asking about this. I’ll give you kind of the quick development story on this. When I was a kid, I was bullied. And my best friend in first grade, I was talking to him about it and said “you know, this kid keeps picking on me.” And he said something along the lines of like, “I’ll talk to him.” And amazingly the kid stopped picking on me. And I said to my friend, like, “Hey, he stopped picking on me”. And he said, “I talked to him”. That would have been back in like 1978. And what that meant was he beat the snot out of that kid and told him if he ever messed with me again, you would beat him up again. And so that is one way to handle conflict resolution. I am not encouraging that as the only way to handle bullying, but as a result of that, everybody knew I was his friend and nobody picked on me anymore. Okay? And I realized as an adult, the value of relationships. And as a person with a disability, I also realized that people who have less power and less strength are often the victims of stigma, are often the victims of bias, are often the victims of bullying. And so I wrote a book for kids. It’s called “Who Me? Yeah You”. And the idea behind the book is that everybody has a role to play in preventing bullying. Whether it’s the bully, it’s the person who’s being bullied, or it’s the bystander, all three have a role. And statistics will show you that in over 65% of cases, when somebody speaks up and says this isn’t right, that the bullying stops within a minute. So, that is a powerful message. So I decided, I wrote the book and was trying to take the book out into schools, and what I was finding is that there were some funding issues for those types of programs. And I thought, you know what? Let’s do something about this. So I started a nonprofit called “Who Me? Yeah You” after the book, and raising funds to give away copies of the book, to do presentations for free, or at least reduced costs for schools that need to have this kind of message. And it is just me as a separate citizen. The cool thing is that sometimes I’m able to do work where they will say like, we can’t pay you, but can we make a donation to a charity? And like yeah, this is what’s near and dear to my heart. Can you help me further this cause? So it’s, it’s been a very, very worthwhile and very cool experience.

[00:27:59] Caterina Rando: That’s a great story, Rob, about your friend, even though he didn’t do a method of conflict resolution that you would do today, still got the job done. Rob, as we wrap up our time together, any final advice for our entrepreneurial listeners?

[00:28:16] Rob Oliver: Yes. My advice is this. Sometimes when you are a solopreneur and you’re feeling very small, you’re feeling like you have to do everything because you can’t afford to have someone else do it, you can’t afford to pay people. I’ll tell you two things, right? Number one, whatever goods and services that you have, people will find value in that, and you may be able to barter some things. Okay? Where you will provide a service for an accountant. You can do something for him, and he will in turn provide accounting services for you for free, or you know something along those lines. The other piece is to understand what is it that you do to generate revenue for your organization? What is it that you do that is essentially you? All right, so now that you know what you do and what you have to do and how you generate revenue, everything that you are doing that is not generating revenue, everything that you are doing that is not essentially you, are things that are keeping you from doing what you’re supposed to be doing, and keeping you from generating revenue. So think about those things and think about how much revenue would you be able to generate if you were able to take the time that you were spending on other things, and devote it to the work that you are essential with, and the work that actually brings money into the business. So let go of those other things, delegate them as much as possible, and focus on doing what you need to do from your own personal skill set, and to grow the revenue of your business.

[00:29:49] Caterina Rando: Rob, you are singing my song. Focus on what is your job and get support with the rest. Because when you’re doing everything, you’re not speaking or selling or serving your clients enough. Everybody, did you hear that? I’m not just the one who tells you, Rob’s telling you too. Bing bing bing. Rob, it’s been an honor and a privilege to be with you today. Thank you so much for your big heart that you bring to your business, for being an advocate and a guiding light for people going through the healthcare system, for people with disabilities, for entrepreneurs, and for speakers. My friends, take some nuggets from my time with Rob today. And remember, you have massive value to bring. There is a lifetime supply of people to serve. Go be loud and proud about your massive value so you can sell more, serve more, and uplift more lives. I’ll see you again my friend, on the next episode of Expand Your Fempire. Thank you, Rob. Thank you so much.

[00:31:03] Rob Oliver: Thank you.

We hope you enjoyed this episode of Expand Your Fempire with Caterina Rando.

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