Black Entrepreneur Blueprint 639 - Jay Jones - Don't Fear Failure But Please Be Terrified By Regret
BLACK ENTREPRENEUR BLUEPRINTSeptember 14, 2026
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27:4439.56 MB

Black Entrepreneur Blueprint 639 - Jay Jones - Don't Fear Failure But Please Be Terrified By Regret

Failure isn't your enemy. Regret is.

We're raised to treat failure like a disease — something to avoid at all costs, hide from teachers, hide from bosses, hide from ourselves. But every entrepreneur who's actually built something knows the truth: failure isn't the opposite of success; it's the price of it.

The real killer isn't the business that didn't work. It's the business you never tried to build. It's the "what if" that follows you for the next twenty years.

In episode 639, Jay breaks down why chasing a failure-proof path is the fastest way to guarantee you never build anything worth having — and why the entrepreneurs who win are the ones who've made peace with losing, fast and often, on the way there.

If you've been sitting on an idea because you're scared of getting it wrong, this episode is your wake-up call.

Listen now — and ask yourself: which one are you actually more afraid of?

GET YOUR FREE ENTREPRENEUR RESOURCES: https://blackentrepreneurblueprint.com/

[00:00:12] Welcome to Black Entrepreneur Blueprint, the number one podcast and resource for Black entrepreneurs. I'm your host Jay Jones and Black Entrepreneur Blueprint was created specifically to educate and inspire Black entrepreneurs to launch, build and grow successful, sustainable businesses. Join us as we help build an economic power base in the worldwide Black community by building and supporting Black owned businesses.

[00:00:41] If you're currently an entrepreneur or want to be an entrepreneur, you're invited to join us each and every week here at Black Entrepreneur Blueprint. Welcome to the BEB family and get ready to elevate your entrepreneur IQ. Welcome to the Black Entrepreneur Blueprint, episode number 639.

[00:01:08] I'm your host Jay Jones and today we have another outstanding and informative show in store for you. Today's show topic is titled Don't Fear Failure But Please Be Terrified By Regret. Don't Fear Failure But Please Be Terrified By Regret. Now, as entrepreneurs, we have to understand that failure is part of the process in becoming a successful entrepreneur.

[00:01:34] And today we're going to discuss failure and we're also going to discuss regret as it pertains to entrepreneurship. Now, before we get to today's show topic though, let me share a few things with the Black Entrepreneur Blueprint family. First and foremost, I want to welcome all first time listeners to Black Entrepreneur Blueprint. Welcome to the BEB family. Please stick around until the end of today's broadcast and I'm going to share all my social

[00:01:59] media contact information and resources such as the website, blackentrepreneurblueprint.com. Make sure you guys utilize the website. We have tons of free resources for entrepreneurs. Go to the site, hit the learn tab. There's a dropdown. You can get free information and resources and content on how to market your business, e-commerce, scaling your business, strategy and mindset, side hustles, everything you need to move your

[00:02:27] business from point A to point B. Now, let's get ready for today's show content. So today family, we're going to talk about don't fear failure, but please be terrified of regret. Now, as a serial entrepreneur after leaving corporate America, I've been a serial entrepreneur for over 25 plus years, business coach, entrepreneur, the whole shebang. So I've seen the highs and lows of entrepreneurship.

[00:02:53] So if you've listened to this show for any period of time, you may know that I almost lost it all twice, but have been blessed to be able to come back both times and build successful businesses. I've started over 17 businesses. Some of them were abject failures, complete failures. Some of them were okay. Some of them were good. And then two of them that were multimillion dollar businesses.

[00:03:18] So I've seen it all guys, like I said, so I'm walking the walk and I'm talking to talk. So one of the things that I had to explain to my wife when we first got married is I think she thought that when you started a business, everything automatically is going to go exactly the way you want it, which is obviously not the right thing to think, right? Because nothing goes as planned. What do they say? The best laid plans, right?

[00:03:44] So there's several things that we have to understand as entrepreneurs, and I'm going to break them down today. Also, this show is for current entrepreneurs and prospective entrepreneurs. There are a lot of people that I talk to that are sitting on the fence that have ideas and they're scared to pull the trigger. Okay. They're scared because they don't know what's going to happen. And that's part of being an entrepreneur. Well, hell is part of living. You don't know what's going to happen any day you wake up.

[00:04:12] You could wake up, get hit by a bus crossing the street, right? So there's always uncertainty out there. But what we're going to tap into today is, is being an entrepreneur and understanding how failure, how powerful failure is. I should rephrase that in terms of becoming a successful entrepreneur. So we're naturally taught that failure is bad, right? Ever since you're little, right? Oh, don't fail in school. Don't fail in this. Don't fail in that.

[00:04:40] And that's the complete opposite for an entrepreneur. We have to change the, the mind, the mindset, the dynamics of how we think about entrepreneurship. So we're always taught guys not to fail. And I get it. You don't want to make failure a habit. Excuse me. You don't want to make failure a habit, but it does happen in entrepreneurship. And so once again, expectations, there's something that my, my pastor told my wife and

[00:05:07] I, when we had our premarital counseling, he said, expectations will make or break any relationship. Doesn't matter if it's a business relationship, personal relationship, friendship, or whatever expectations. So you have to understand and recognize what to expect when you start out on your entrepreneurial journey. So understand that failure is part of the process. And we're going to touch on a couple of things today, and I'm pretty much going to freestyle

[00:05:36] it with a couple of bullet points. But I really want to, want to hammer in guys that don't fear failure, but please be terrified by regret. Do you know how many, uh, great businesses never took off or never even started because people were, were scared. And I've got stories all day long about this, talking to people who's like, Oh yeah, I should have done this. I should have done that. And years later, unfortunately they end up regretting it.

[00:06:04] So let's talk about first, you got to understand what entrepreneurship is and what it takes to become successful. So anytime you think you're going to start a real entrepreneur, entrepreneurial venture, and it's going to go from zero to a hundred overnight, you're delusional. Okay. And I know you need delusion sometimes to be successful, but that's probably not going to happen. So you have to expect that you're going to have bumps in the road.

[00:06:31] You have to expect that things aren't going to go smoothly. And one of the biggest things about understanding entrepreneurship guys, you, you can't read about it. You can't watch videos about it all day. You have to immerse yourself into the business. That's when everything will be revealed to you and everything will be uncovered. Uh, there's a little saying that I say it's, it's three words and six letters to be do in order to be something.

[00:07:00] You have to do something, right? You need action behind it. So I don't care how much you study and try to prepare for entrepreneurship guys. And I'm not saying that you shouldn't study in, in all that good stuff, but you're really not going to learn anything until you get in and do it. And I talk about knowledge versus know-how, right? Knowledge can be acquired by watching a documentary. It can be acquired by watching somebody fix a car. You can actually get a manual, right?

[00:07:30] And of whatever you're trying to do and look at it. But here's the example I give. So it doesn't matter if Jay Jones reads how to fly an F-16 fighter jet manual. I could read that manual from front to back. I could watch a video of how to fly that airplane. I could actually be in the cockpit behind the pilot while he flies the actual, she flies the actual plane, right? So I'm getting knowledge.

[00:07:58] But if they put Jay Jones in that cockpit and said, Hey, fly this F-16, right? Do I have the know-how? And the answer is absolutely not. Know-how comes from doing. Knowledge can be acquired from all types of different places. So as an entrepreneur, you're going to have to get that know-how. Knowledge is great. You're going to need that. It's going to help direct you and it's going to help you, you know, move along. But know-how, the actual doing.

[00:08:27] So understand what entrepreneurship is and what it takes to be successful. Now let's talk about failure and actually the power of failure and how you use and harness failure to become successful. So one of the things I had to always tell my wife is, you know, because she didn't come from an entrepreneurial background. So her parents were educators. She's in the education field and that's a pretty stable field, right?

[00:08:55] So you have to do something real crazy in order to get kicked out of, you know, being a teacher or an administrator. So the power of failure for an entrepreneur is that number one, you expect it. And when I say failure, that doesn't necessarily mean that your business dies, even though that could be failure. But here's how the power of failure works to your benefit. As long as you do not make the same mistakes twice, you're going to be in good shape. Now you can start a business.

[00:09:24] You find out that the business isn't viable after you've been in it. Guess what? Shut it down and collapse it and come back out with something else. With the know-how and the knowledge that you've received from being in that business. So failure is not a bad thing as an entrepreneur. It teaches you things. The fallback or the pitfall is, is not understanding and making the same mistakes twice.

[00:09:54] So if you go into one business undercapitalized and everything looks good, but you don't have enough capital to pull it off and then that business fails and then you come back out with another business where you're undercapitalized. Guess what's going to happen? For the most part, it's probably going to happen again. You have to learn by your mistakes and by your failures. Okay. And the only time you truly fail guys is when you give up. That's when you, that's when you truly fail.

[00:10:23] When you give up. If you start a business and it doesn't work, guess what? That's fine. Come back again, start another business. Doesn't work. That's fine. You're learning all the time. And let me, uh, actually credit, uh, the young lady who came up with this don't fear failure, but please be terrified by regret. But it actually came from a, uh, a sister who is a, uh, miss. I think she was miss USA. Her name was Deshauna Barber, I believe.

[00:10:52] And I think she talked about this in Ted talks or somewhere. And she was saying that somebody came up to her on the street and said, you know, Oh my God, you're gorgeous. Have you ever been in any pageants? And she was like, you know what? I've never even thought about it. And she said, follow me and I'm going to make you into a pageant winner. So she went, started doing all of this training and she went to her first miss USA fail, second fail, third fail, fourth, fifth.

[00:11:20] And finally on the sixth time she became miss USA. And so what she said was don't fear failure, but please be terrified by regret. And so the power of failure guys, you have to use that to become successful. And it takes a lot of intense and intestinal fortitude to do that because many times we start failing. And guess what?

[00:11:45] Our first inclination is to quit because that's how we're brought up. That's how we, you know, we learn. So, and what we're talking about guys is don't fear failure, but please be terrified by regret. And I'm just giving you guys a couple of bullet points to, to help you right now as entrepreneurs. So if you're a current entrepreneur, guess what? You're not doing well. Failure is part of the process. Setbacks are part of the process. If you're a prospective entrepreneur, I want you to understand what you're getting into.

[00:12:15] And I want you to have the right mindset and the right mind frame to become successful. All right. Let's talk about how to reprogram your mind to understand why failure is important. And basically guys, this is something that most people aren't going to understand because as I mentioned earlier, we're not born this way and we're programmed not to fail, which is a good thing in regular life, right? But we're entrepreneurs.

[00:12:42] So we live on a different, on a different universe and a different plane. Our minds think differently. And because our minds think differently, we have to continue to train our minds so we can be successful in doing what, what we're doing. So I call W2 employees civilians. And I don't mean any disparage disparagement by that, but most times their minds think totally different than an entrepreneur's mind. So I'm always looking at opportunity.

[00:13:11] Even when I was a corporate employee, I was like, man, if they're paying me this much, then how much am I really worth? And then my supervisor, I know I'm smarter than this guy. You know, I know I have more know-how than this guy and, and they've got the job and they're making more money off of my efforts and off of my, my back. So why am I even in this position? So that's how I used to think when I was an employee, I was the worst employee you could have ever had.

[00:13:40] Not because I didn't do the job or didn't, uh, or didn't particularly, uh, like the job, but because my mindset was different. I always thought about not me working in the business, but me owning that business. And sometimes it got out of hand because I would give too, too many of my, uh, my suggestions and ideas and I would undermine it. Well, a lot of times the managers would think I was undermining them, but I'm thinking

[00:14:07] differently than most people because I'm thinking as an entrepreneur, you know, I got tons of stories about this, but you know, you have to reprogram your mind to understand why failure is important. Now I'm not telling you to go out there and try to fail. You know, you want to try to be successful, but if you do fail, there's an old saying, fail fast, fail quickly. So you can get out there and take that knowledge and that know-how from failing and be able to

[00:14:35] put it in your, in your belt, put it in your backpack. So you know what it is. So you don't come across that again. Okay. And what we're talking about, don't fear failure, but please be terrified by regret. Let's, let's switch over to regret a little bit. Now I've been an entrepreneur pretty much all my life since I was a kid, you know, bagging up, uh, big bags of potato chips, breaking them down into small bags, making Kool-Aid and selling it in the summertime on the street in Philly while we're out running around on the

[00:15:04] blocks. I'm selling stuff and I'm making money off of potato chips and Kool-Aid. Right. So, um, regret, right? So I've always been an entrepreneur, but I've spoken to and speak to so many people that have had business ideas that are now, they feel that they're past the age where they could or should have started this business. And they have so much regret. They regret not trying that business. And one thing I always tell people is, you know what?

[00:15:34] The best time to start a business is if you have a full-time job or if you have a job. And the reason I say that if you want to test the waters, you know, you work your regular nine to five, but, but you know, from, from after, from nine to five, that's, that's corporate time from six to 11 or whatever, that can be your business time. You don't have the stress of not making money and it gives you the time to be able to ramp up your business.

[00:16:02] If you have the stick to it,iveness to do that, because you're actually going to be pretty much working two jobs. All right. But the sting of regret. So I've talked to so many people and they were like, man, if I would have started this 10 years ago, you're right. There's no perfect time to start a business. I don't care what anybody says. Nothing is going to be lined up a hundred percent. So you have to go out there and start mixing around and start putting the plan in place.

[00:16:31] And then the biggest thing, guys, I just told you this before, you know, three words, uh, three words, six letters to be do. And that do means action. So if you want to be the best gymnast out there, guess what? You're going to have to do the work. You want to be the best entrepreneur out there. You're going to have to do the work. All right. So instead of thinking about it, you need to do it.

[00:16:57] Uh, I mentioned this on several episodes before I had this cohort where I was, uh, teaching people how to build e-commerce products and bring the products to market private label products. And we had a brother in the class, man, nice brother. But all he did was research, research, research, and research. He was, what do they call a paralysis by analysis? He was scared to actually pull the trigger.

[00:17:24] And I'm telling you right now, he had some great ideas. And if he had taken just one of those ideas and put it into play and followed the blueprint or the game plan, he probably could be successful. So if you're sitting there right now, listening to this, you could be on your way to work. You could be working out. You could be sitting in a doctor's office or whatever you're doing. If you have an idea about a business, put it into play. Don't walk around with that regret. Okay, please.

[00:17:52] I'm telling you, it's going to kill you. So it's almost like if somebody said, what happens if you invested a thousand dollars in Amazon when it first came out? Now, of course you don't know what was going to happen and that Amazon was going to blow up to be a multi-billion dollar company. If you would have invested in Amazon, you know, when it came out, what, 25, 30 years ago, a thousand dollars, you'd be rich right now.

[00:18:18] If you would have invested in your business 10, 15 years ago, even five years ago, whatever, you could be in a different financial place right now. So what I'm trying to tell you is guys, you know, don't regret it. And here's what, what happens. Regret grows more as time goes by. Regret grows more as time goes by. So just think it's not going to hurt you that much.

[00:18:44] If you know, man, I, I had this business idea six months ago and I never pulled it off. That's not going to hurt because it's so recent. But if you're in a situation five years down the line and you don't like where you are, that regret is going to be bigger because you said, damn, I should have started this business five years ago. Who knows where I would have been, you know, right now, who knows what would have happened. And that's the whole beauty of entrepreneurship, guys. It's a beauty. And it's also a curse.

[00:19:13] You don't know what's going to happen. You may build something that you think isn't going to be a great big business. And it turns out to be a winner, a killer. You could build a business that you don't think is going to be great. And somebody could want to buy it from you and change your entire life. Okay. So you don't know what's going to happen until you get out there and start mixing around to be due to be due. So these are some of the things guys that you have to understand.

[00:19:42] And, and let me, let me, let me break this down and I'm going to go into this a little bit more in the last segment, but what can you really count on right now in today's economy? People getting laid off left and right. I don't care what job you're in, what position you're in. People are getting fired, laid off. The economy is crazy. And who are you going to depend on? But yourself, you always want to bet on yourself, right? So you always want to have those multiple streams of income.

[00:20:12] So God forbid, if you do lose your, your nine to five, you'll have something to fall back on. Okay. Or if you're an entrepreneur and your business goes bad, make sure you have other streams of income. We're going to talk about, you know, uh, parlaying parlay this business, maybe just something that's ancillary that can help generate revenues in a different vertical or maybe in the same vertical, but in a different way.

[00:20:42] So you have multiple streams of income and we're going to talk about that in two seconds. But before we get to the last segment, guys, let me just share all my social media contact information and resource links. I mentioned at the top of the show, guys, utilize the website, go to blackentrepreneurblueprint.com, hit the learn tab. We have all types of free resources to help you go from point A to point B actionable steps.

[00:21:09] This isn't about rah, rah over here, black entrepreneur blueprint. So if this is your first time listening, we're not about, you know, rah, rah, getting you all hyped up and then not giving you any direction. So if you want actionable steps, go to the blackentrepreneurblueprint.com, hit the learn tab. There's dropdowns. Like I said, strategy and mindset, marketing, e-commerce, scaling your business, everything you need to help you elevate your entrepreneur IQ.

[00:21:36] Now, if you want to get in touch with me guys, anything long, hit me on my email, jjones at blackentrepreneurblueprint.com, J-A-Y-J-O-N-E-S at blackentrepreneurblueprint.com. Facebook, blackentrepreneurblueprint. Instagram, I have two IG accounts. The first one is jjonesforreal, J-A-Y-J-O-N-E-S, the number four, R-E-A-L. Second one is blackentrepreneurblueprint.

[00:22:01] LinkedIn, go look for jjones, blackentrepreneurblueprint and SaaS founder. You can find me there on LinkedIn, connect there. Also, XJJones001, J-A-Y-J-O-N-E-S-001. Also, YouTube, make sure you hit that subscribe button, go to YouTube, type in blackentrepreneurblueprint. We have additional content on YouTube that is not on the show. And for all you first time listeners, guys, wherever you're watching this or listening

[00:22:31] to this, make sure you hit that subscribe button so you get alerted. When a new episode drops, we drop every Monday morning, 5 a.m. Eastern Standard Time on all your major podcast platforms and YouTube. So in this last segment, which is going to be real quick, I was talking prior to giving all my contact information, multiple streams of income as an entrepreneur. One of the things I do want to clarify, don't start a second stream of income, guys, until

[00:22:59] your business is built up enough where it's giving you a consistent income from the jump. Many times as entrepreneurs, we'll start doing two or three different things at a time and none of your businesses are generating a consistent income. So you want to build up one income first. And then once that's built up, you have your systems in place. It's running well. It's running smoothly. It's running without you. Then you can start to look to build another stream of income.

[00:23:29] And once again, you can parlay what you're currently doing with your business or you can find something that accentuates your business in terms of making revenue. So you just have to figure it out. Perfect example. When I owned my first mortgage company, obviously mortgages were where we were making our money. Then we kept getting so many people that were credit challenged. We started doing credit repair. First thing we started farming it out to people.

[00:23:57] They were jacking it up, charging people money and not doing anything. So we actually bought that in-house and we had our own credit repair company inside of the same office as our mortgage business. So it was an ancillary service that actually was profitable on its own. So those were two separate income streams. Even though they jogged, you know what I mean? They were together. Made sense if somebody came to us and couldn't get approved for a mortgage because of their credit.

[00:24:27] Hey, we can help you over here. So we didn't start that at the same time as the mortgage business. We started that secondarily because number one, it was a need. It was a need for us and we figured we can capture additional streams of revenue by helping people. We can get, you know, pre-qualified and prepared to get mortgage ready. So don't go out and start all kinds of different streams of income right away. All right.

[00:24:55] Get one thing working with your business. Make sure you hone that and it's running smoothly. And then you start looking at building that second income with an ancillary product or service, or it may be something totally different. But one of the things that I want you guys to understand is like the title says, don't fear failure, but please be terrified by regret.

[00:25:18] So if you have the gumption, if you have the thought of starting your business, start it now because it's never going to be a perfect or optimum time to do that. You're never going to be in the perfect spot to start that business. All right. So get out there, start, you know, making waves, start doing stuff. And what happens once you get in there and start making moves, you're going to see what it takes to become successful and you're going to know what you need to do next.

[00:25:45] So thinking about it, studying about it, all that stuff is fine and dandy. But until you start mixing around and actually doing something, guess what? You're never going to find out. And don't sit there five years later and be like, damn, I wish I would have started this. And I know there are people out there that have friends and family members that they told them, yeah, I'm about to start this business. And y'all may have laughed at them, but five or 10 years down the line, they're super successful.

[00:26:14] And you're looking at them like, damn, I should have started my business. Don't let that be you. All right. Don't let that be you. So recognize and understand that failure is part of the process for an entrepreneur. Okay. Failure is part of the process. Recognize and understand that. So you're going to go through your ups and downs. But remember, the key to moving forward as an entrepreneur, do not make the same mistakes twice. You learn from it. You build from it.

[00:26:44] You put that in your tool belt. So now you know what to do in case something happens like that again and you're able to get over that hump. All right. So don't have regrets, guys, and understand that failure is part of the process in becoming a successful entrepreneur. So the thing is, failure isn't the opposite of success, guys. It's actually the price of success. Failure is not the opposite of success. It's the price of success. All right, guys, that's today's episode.

[00:27:14] But before we go, I just want to say I appreciate you guys so much. Please continue to spread the word about Black Entrepreneur Blueprint, the podcast, the ecosystem, the books, the online courses, everything designed to help you elevate your entrepreneur IQ. Remember, it's not about me. It's not about you. It's about us. It's about building an economic power base in the worldwide black community by building and supporting black owned businesses. Love you guys. See you same time next week. Peace.