From Zero to Hero: Lessons on Rejection, Resilience, and Momentum

12 May 2026 · 31 min · 13 chapters

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In short

Rejection and resilience as the foundation for success, plus practical business lessons on momentum, inside-out change, and rewriting the playbook; includes stories from multiple entrepreneurs and business operators.

Guests (backgrounds)

  • Mike Sancho: entrepreneur who says he was expelled from high school and college; later arrested, jailed, then rebuilt his life.
  • Alex Morton: network marketing leader (claims top-earning under 35); built brands via sales/marketing and education in crypto/Forex/e-commerce.
  • Jen Gottlieb: actress turned media entrepreneur; co-founder of Super Connector Media; Broadway tour background.
  • Jamil Damji: real estate entrepreneur; started in wholesaling after rejection from medical school.
  • Ken Wentworth: radio host and fractional CFO/business consultant; focuses on margins, pricing, and implementation.

Key claims

Success is inside-out; rejection (“no”) is fuel; don’t follow the playbook—rewrite it; execution beats information; business value rises via margin, sales, and leadership buy-in.

Notable examples

  • Mike: jail decision → two jobs (Subway, 82 Queen) → store manager in 6 weeks.
  • Alex: “best friends with no” from daily auditions; network marketing stigma but word-of-mouth model.
  • Jen: authentic self (Britney impersonation) wins roles; imposter syndrome is universal.
  • Jamil: skip transfer deal after medical school rejection; $47k cashier check.
  • Ken: requires leadership implementation; insists on attending staff meetings/offsites.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

From Troubled Beginnings

0:45 to 3:00

The host shares personal experiences of struggles and turning points in life.

“But to listen to a young guy with a Rolls Royce and some big houses and some jewelry, you kind of blind them with like, hey, this is what I have and this is what I've done.”

The Drive to Succeed

3:00 to 6:00

Exploring the commitment to hard work and the principles of success tailored for millennials.

“Today, we're breaking down the real journey to that first breakthrough.”

Imposter Syndrome in High Achievers

6:00 to 9:00

Discussion on imposter syndrome and its prevalence among successful individuals.

“I was able to just clear out all the bullshit in my life.”

Business Fundamentals and Misconceptions

9:00 to 12:00

Addressing common misconceptions in business practices and the importance of mastering core skills.

“Most people don't struggle with knowing what to do to lose weight.”

Entrepreneurial Journey of Hardships

12:00 to 14:00

The host recounts early entrepreneurial struggles and the lessons learned from failures.

“Money to me is just one of the spokes on the wheel.”

The Evolution of Network Marketing

14:01 to 15:10

Learn how network marketing has impacted the speaker's life and career.

“They say it's a get rich overnight thing.”

Jen Gottlieb's Journey to Authenticity

15:10 to 18:00

Discover Jen's transformative career path from actress to business leader.

“That's what I've been a part of and that's been the biggest catalyst financially for sure in my career.”

Resilience and Rejection in Entrepreneurship

18:00 to 21:04

Understand the importance of resilience and embracing rejection in business.

“It wasn't that I knew everything about heavy metal music.”

Jamil Damji's Real Estate Insights

22:19 to 24:19

Explore Jamil's unconventional path into real estate and entrepreneurship.

“There's no one better than my good friend, Jamil Damji.”

The Power of Choices in Life

24:19 to 28:03

Realize how making bold choices can reshape your life's trajectory.

“at the way the system is kind of set up and just rejecting it.”
Show all 13 chapters

Ken's Journey to Radio Hosting

29:26 to 30:26

Discover how Ken transitioned to hosting a radio show.

“They had asked me to be a guest on someone else's show to come on as a business expert.”

The Role of a Fractional CFO

30:26 to 32:33

Explore what businesses seek when hiring a fractional CFO.

“It's another avenue creating content and be able to put content out for people and things like that.”

The Importance of Client Implementation

32:33 to 34:24

Understand the need for client commitment to business changes.

“In my agency now, my role a lot of times with the client is what you just described, because that's my expertise in marketing and branding.”
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Transcript

Automatic transcript. May contain errors.

0:00I learned my lesson when I got kicked out of college. I got arrested and they took me down to jailhouse and I spent a few weeks in there. I came pretty close to some more serious charges and actually doing some prison time. That's when I really made that decision in my life when I was in that jail cell all alone. And I just made that line in the sand decision of I'm going to flip the script and people are going to be surprised. They're going to see what happens from here. Pretty much made a promise to myself that I'm going to just outwork everybody and I'm going to go all in all the time and I'm going to do whatever it is.

0:30takes to be successful and I'm going to do it legally. I talk about how I went from a broke college kid to a multimillionaire. It really boils down to just the age old success principles, but I kind of tailor it to like the millennial generation because a lot of young people, man, they don't want to listen to somebody with white hair. It is what it is. But to listen to a young guy with a Rolls Royce and some big houses and some jewelry, you kind of blind them with like, hey, this is what I have and this is what I've done. And then you give them real information that they can apply and actually change their life if they want to.

1:00Everybody, even the biggest rock stars in the world have imposter syndrome because even the biggest people that perform for years and years in front of millions of people would come backstage and they would be so nervous to go on and be interviewed and they would come backstage and they would say to me, did I do okay? Is that good enough? I'm like, dude, you're slash. Are you asking me if you were good enough? Are you kidding? So it was a really nice reminder to me that people are people are people. And like, every time I get nervous or I feel like an imposter or feel not good enough. Everybody experiences that.

1:28It's a human condition. When you're in a survival mode, you do what you've got to do to survive. And that means you're clutching and grasping and filling holes of worthiness and filling holes in yourself with whatever you can. And even though it's temporary, and even though the chemical lasts its half life, and then you got need more of it, or you crash and you're on this hamster wheel of trying to maintain, eventually you fall, you fall on your ass and you see that you've got to make a real pivot, a real change, something from the inside out. That's why I really believe success is an inside job.

1:57Ken Wentworth:A lot of times business owners are really good at the widget they produce or whatever service they're providing, but they're not really good on the business side of things. Increasing sales, increasing your net income, increasing the value of the company. Especially now you get a lot of baby boomers that are considering exiting and wanting to sell their company. How do I improve the value of my company? Most business advice is wrong, built on opinions echoed by people who've never done it. But the truth, it's simpler and harder. You don't win by following the playbook. You win by rewriting it.

2:33Ken Wentworth:700 episodes deep with the people who actually built something real. No theory, no fluff, no shortcuts. This is Right About Now with Ryan Alford. Every success story has a beginning, and it's usually messy. Before the wins, the money, and the momentum, there was doubt, failure, and starting from zero. Today, we're breaking down the real journey to that first breakthrough. Featuring insights from Mike Sancho, Alex Morton, Jamil Damji, Jen Gottlieb, and Ken Wentworth. This is where the grind begins and everything changes.

3:42and they're selling the products on TV. I was trying to invent products at that point. And I would go to my mom and say, hey mom, can you help me get a patent? I was like trying to get patents with my mom's help at eight years old. Not many kids doing that. I had it early on. I just started to get into more and more businesses as a teenager. Not necessarily all of them legal businesses. I started selling a little weed as a kid. It's a common theme, I guess, in entrepreneurs. They take their business skills to a different kind of industry. That ended up getting me in a little bit of trouble. I ended up getting kicked out of high school because of it.

4:09Found my way into college after that and didn't learn my lesson the first time. I'm that guy who got expelled from high school. You were the true entrepreneur.

4:15Ken Wentworth:Yeah. Every friend I knew was either smoking or selling it or who knows what. I don't know. You had to make money somehow. But I can relate to that entrepreneur, Gene. I like that. I'm that guy that got expelled from high school and got expelled from college. As you can imagine, my family was wicked proud of me at that time. I had a.71 my first semester at Clemson. Is that even possible? 0.0. That's at F minus. My ass got yanked home first semester. It didn't go well. so I can relate to making the family proud. I think you were majoring in parties and girls instead of class. I think that was the exact line I used on a podcast once.

4:48Ken Wentworth:I was majoring in boobs, boobs, and beer. Hey, you got to go pro in something. I think I was a pro. You finally learned your lesson. I learned my lesson when I got kicked out of college. I got arrested. They took me down to jailhouse. I spent a few weeks in there. I came pretty close to some more serious charges and actually doing some prison time. That's when I really made that decision in my life When I was in that jail cell all alone, I just made that line in the sand decision of I'm going to flip the script. People are going to be surprised. They're going to see what happens from here. Pretty much made a promise to myself that I'm going to just outwork everybody.

5:20I'm going to go all in all the time. I'm going to do whatever it takes to be successful. And I'm going to do it legally. From there, I got out and went to Charleston, South Carolina. When I got out of jail and I was living with my parents, I had no money. I was in debt, probably one hundred thousand dollars from student loans, car loans, lawyer fees that I owed back to my parents. you name it i was in a big hole at 21 years old but your whole life was in front of you exactly

5:42Ken Wentworth:exactly but you didn't realize this at the time i'm sure you probably felt like you know life's over but i was motivated i was fired up actually that's good i was fired up most people get in those holes though and people need to hear that kind of reflection of knowing what was ahead of you you were just barely getting started even if it started a little bad yeah a little rocky when your back's against the wall and you're at rock bottom for me it was purifying i just felt free I was able to just clear out all the bullshit in my life. It's a fresh start. It's a clean slate. I went down the main strip, King Street in Charleston.

6:11I applied at every single restaurant, shop, whatever. I took the first two jobs that I could get. One was at Subway for$7.50 an hour. The other one was at a restaurant called 82 Queen washing dishes. I started working two jobs like a madman. The crazy thing is I decided to outwork everybody. And that's in everything because I said, how you do anything is how you do everything. So I came in at Subway. I started showing up 30 minutes early working before I even clocked in. I started going in, cleaning the bathroom, cleaning underneath the oven, straightening the chips. This is before I even clocked in and you're talking subway.

6:41I know you can imagine the work ethic that comes with that for a lot of the people there. Customer service through the roof. I was staying late, clocked out, still working, still helping, sweeping, taking shifts, being super helpful. Within six weeks, they made me the store manager at 21. Within another two months, they made me the general manager of five locations because I just outworked everybody. This is the ethic that I've kept with me since that point. I just kept it booming. I was grinding my ass off. I took that into everything and I started to take as much courses as I could, studying constantly about making money, all different types of industries, learning trading, crypto, e-commerce, real estate, course after course after course.

7:17There was no break. I shut the TV off. I just went all in. At that point, I tried to quit my jobs to go full-time into entrepreneurship, which was also a rocky road. The first thing I was doing was real estate investing. I was doing wholesaling. I started flipping properties, ultimately ended up going broke with that. I didn't have enough resources at the time. And pretty much I went on this cycle of quitting my jobs to go full-time into entrepreneurship, losing all my money, failing, and having to go back to work another job. I repeated that cycle for four times before I finally got fully.

7:46Ken Wentworth:If you've got kids in middle school or high school, you already know homework can turn into a whole situation. What should take 20 minutes somehow turns into two hours and half the time it ends with frustration on both sides. I've got four boys, three of them right in that middle and high school range. So I see it all the time. They hit a problem, get stuck and it's not that they don't want to figure it out. They just don't know how to get there. That's why I've been looking into Brainly. Brainly is basically a 24-7 AI powered tutor that actually walks them through problems step-by-step, not just giving answers, by helping them understand how something works so they can build confidence and keep moving.

8:27Ken Wentworth:And as a parent, that's the part I care about. It's not about the shortcuts. It's about them actually learning the material. It's also just practical. You don't have to deal with scheduling a tutor or trying to find things that line up around sports and everything else. It's there whenever they need it. And it's a lot more affordable than traditional tutoring. Honestly, it just takes a lot of pressure off. Finals are coming up. Build your teen study plan now. It only takes minutes. Go to brainly.com backslash Ryan to get 50 % off your first Brainly subscription. With my code Ryan, that's B-R-A-I-N-L-Y.com slash Ryan.

9:07Ken Wentworth:Let's be honest. Most people don't struggle with knowing what to do to lose weight. It's actually staying consistent with it. Life gets busy, routines fall off, and before you know it, you're back where you started. That's why I've been looking into weight loss by HIMSS. HIMSS now offers access to an affordable range of FDA-approved GLP-1 medications, including the Wagovi pill and the Wagovi pin. It's designed to help regulate your appetite so you're not just constantly fighting cravings, which makes staying on track a lot more realistic. And what I like is how simple they make the whole process.

9:43Ken Wentworth:Everything happens online. You connect with a licensed provider. They figure out if it's right for you. And if prescribed, it gets delivered right to your door. No insurance needed. They also give you support beyond just the medication, 24-7 access to a care team, plus nutrition guidance, recipes, fitness content, all the stuff that actually helps you stay consistent. Ready to reach your goals? Visit hems.com slash Ryan to get a personalized, affordable plan that gets you. That's HIMSS, H-I-M-S dot com slash Ryan. Membership required, fee not included, and billed separately. Weight loss by HIMSS is not available in all 50 states.

10:24Ken Wentworth:WGOVI is the registered trademark of Novo Nordisk, A-S. To get started and learn more, including important safety information, WGOVI clinical study information and restrictions, visit HIMSS.com.

10:37Ken Wentworth:We're talking success engineering. We're talking to Alex Morton. What's up, brother? What's up, man? Happy to be here. I watched some of your speaking stuff. You're really dynamic. There's an authenticity to you, man, that really struck me. It wasn't overly produced, but it was still polished. It was authentic. That's probably had something to do with your success, if I had to guess. You can always tell someone that maybe made$100 ,000 one time in a month or even a year, and everything's got to be super formulated and organized, all this kind of stuff. And one of my good friends and mentors, Grant Cardone, which a lot of people know, I love the guy so much, not just because he's a good dude, but he's so raw and real.

11:15And he's like, I'm going to tell you the way it is because I've done it. And I feel at my age, are there people that have made more money than me? Absolutely. But being able to earn dozens of millions of dollars in your low thirties, you learn a lot of stuff. And I feel like I know how to just give people the truth. So why mess around with all the marshmallows and rainbows? Just tell people how it is. And if some people like you, love you or hate you, that's not even my business. My business is to give people the formula to go out there and win. And that's that.

11:43Ken Wentworth:What defines success for Alex Morton? Well, it's changed, man. At 21, when I'm making no money a month and I see the possibility of making$40 ,000 a month, I wanted to party, have fun, spend money, cars, watches, clothes, all this kind of stuff. But now at 32, in my personal growth journey, obviously has extrapolated out. Money to me is just one of the spokes on the wheel. My biggest goal now is to be the best newly married, the best husband I could possibly be, be the best leader I could possibly be. I feel like money is a massive part of success, but it's really living on purpose, being fulfilled at the end of the day.

12:20And a lot of people say, I just want to go change people's lives and I want to help people. And to me, it's like, I want to make a ton of money, but I want to do it by helping a lot of people and making a difference. So that's where I kind of sit now on this idea of success. And I also believe it's a moving target. You have an entrepreneur get to a hundred grand a year, immediately they want 200 grand a year. It's

12:38Ken Wentworth:this progressive realization of what you really want. When we talk about this industry being in it 12 years, what exactly are we talking about? Network marketing. I'm one of the highest paid, probably the most money ever earned under 35. And that's not ego. I'm a very humble guy. It's just, that's what it is. But there's pros to our industry. There's cons. Some people love us. Some people despise the industry, but I've used this as the platform to build my name, my brand, and to also impact people in 75 countries around the world. So for me, it's been a great environment for growth. Network marketing comes with a stigma.

13:14Absolutely.

13:14Ken Wentworth:And I feel like you're breaking it daily. How do you define network marketing? It's the idea of instead of spending money on billboards, magazine ads, TV commercials, movie previews, YouTube ads, it's the idea of word of mouth. And obviously it works. It makes sense. Like you look at these companies like Amway, Arbon, Mary Kay, right? They're doing 5 billion, 7 billion a year and it works. I think network marketing, this is my opinion, doesn't mean it's fact. I think it's the best opportunity for someone that doesn't have a surplus of cash to go start a business. They can get started for 2, 3, 4,$500.

13:50It's not guaranteed, but they can get to 6, 7, and even 8 figures a year through hard work, learning, persistence. but there is a stigma because there's a lot of people in our profession that do it super bad, super wrong. They market it terrible. They say it's a get rich overnight thing. Dude, it's not a get rich quick. It takes time just like anything else. But yeah, network marketing has given me my shit. It's given me a lot, man. So

14:11Ken Wentworth:you obviously are pushing certain products, certain services. What have been the cash cows of the 12 years? Where I really hit my first home run was a healthy energy drink. Imagine I'm in college. I'm an Arizona state, number one party school in the country, right? And everybody's slamming rebel, rockstar, monster. And I'm like, dude, instead of drinking that, drink this, you're going to get paid for it. It went viral. I was like at Ohio state. I was at Michigan state. I was at ASU. I was at university of Texas and Austin. Tens of thousands of young people just going bonkers with this thing. And then I kind of grew up and I realized it's not even about really the product so much, the physical product so much.

14:48It's about freedom. I fell into a company where I've been now for six years and it's obviously been the grand slam of my career where it's real financial education. It's cryptocurrency, it's Forex, it's e-com and it's just education. We don't invest money, we don't make money on brokers, but we give people some of the education that if they grew up in the middle class America or in Ecuador or Peru or in poverty, their parents never taught them about how to make money, how to multiply money, how to save money on taxes. That's what I've been a part of and that's been the biggest catalyst financially for sure in my career.

15:19Ken Wentworth:Crypto and NFTs, anything and everything that's kind of falling out of digital currency. There's an education that you do and promote, and there's a network aspect, I guess, a layering of compensation for that education. We've got great traders and educators that teach people how to trade and multiply money and all that. And then there's people like me that are sales, marketing, leadership, momentum, because I've been a part of close to probably$2 billion now in team sales. So I go in there and help just explode the marketplaces and build the business. Talking to another media person, the famous woman.

15:58Ken Wentworth:She's a pretty lady, but she's a damn good business person. Talking to Jen Gottlieb, co-founder of Super Connector Media. What's up, Jen? What's up, Ryan? I'm super excited to be here. Media's changed so much. TV's changed and distractions and where media is on the smartphone and on social media. But reflect on those VH1 days. The VH1 thing really happened on accident. I was an actress. I studied musical theater in college, and then I dropped out of college. I moved to New York City to study musical theater at a two-year conservatory program. Immediately after studying at the school that I was at called the American Musical and Dramatic Academy, I booked my dream role in the Broadway national tour of The Wedding Singer.

16:36I played Linda the bitch that leaves Robbie Hart at the altar. In the show, she's this Lita Ford wannabe rock star. She looks like a combination of Joan Jett and 80s Madonna like a virgin. She's just this hilarious wannabe rock star chick. I was on the road playing this character for a year and I get back from doing that. And I see this audition for a sexy rocker chick. And I'm like, Oh, I could play that part. I could play that character. I know nothing about heavy metal music. I know nothing about rock and roll, but I'm like, this is a gig. I'm an actress. I can go get this. I'm going to go land this.

17:06I needed a job. The night before the audition, I Googled everything there was to know about heavy metal, learning all the band names. I go in pretty much I felt like I bombed the audition because I kind of forgot all the things that I was memorizing. They're like, what kind of music do you like? I like everything from Beyonce to Black Sabbath. They could probably tell that I didn't know what the hell I was talking about. At the end of the audition, they're like, Oh Jen, I noticed at the bottom of your resume, it says that you do a great Britney Spears impersonation. So I'm like, yeah, okay, I do.

17:34They're like, can we see your Britney? And so I do my Britney Spears impersonation. They're all laughing hysterically. It's like an uproar. Everyone finally is alive after being kind of bored with me because I didn't know what I was talking about. They call me two weeks later and they're like, we want you to be Miss Box of Junk on that metal show. And I'm like, really? They're like, yes, you made everyone laugh. Your Britney Spears imitation got you the role. That was the first moment in time when I learned that being my most authentic self is always what's going to get people to lean in and pay attention.

18:04It wasn't that I knew everything about heavy metal music. It was when I finally let myself shine that actually got me the gig. I get this gig by being myself, ironically, but I immediately reverted to, I have to play this version of myself that wasn't me. I had to become heavy metal Jen. I wore super tight spandex pants and I cut up all these rocker shirts and I pretended I like heavy metal music, even though I didn't. And before I knew it, I had this big audience of all these metal guys that thought I was like this metal girl. I had built this brand that was a lie. I got to meet all these huge rock stars.

18:34One thing that I learned about people from this experience is that everybody, even the biggest rock stars in the world have imposter syndrome. Because even the biggest people that perform for years and years in front of millions of people would come backstage and they would be so nervous to go on and be interviewed. And they would come backstage and they would say to me, did I do okay? Was that good enough? I'm like, dude, you're slash. Are you asking me if you were good enough? Are you kidding? So it was a really nice reminder to me that people are people are people. And like every time I get nervous or I feel like an imposter or I feel not good enough, everybody experiences that.

19:06It's a human condition. I lost myself along the way because I was playing a fake version of myself that couldn't have been further from who I really was. And when the show ended, I had to reinvent myself and start showing the world who I am. And that was a big lesson in a lot of ways. But I'm really grateful for the time. It was fun. And it gives me a really amazing story to tell.

19:24Ken Wentworth:What framed your business perspective? You're a singer, actress, multi-talented, attractive. What do you feel like molded you as the business person? It was really a lot of getting heard. No, I think that one of the most powerful tools that a successful entrepreneur can have is resiliency and the ability to be persistent. Even when you're getting heard, no, when you're getting rejected, many people, the second that they hear no, or they get rejected or the thing that they want doesn't work, they stop or they just like, Oh, I guess this isn't for me. I'll go grocery shopping today and forget it.

19:54I'm not going to try anymore. Right. I'm going to go binge Netflix or do something else that makes me feel good because I don't want to be rejected. When I was an actress, I was a professional auditioner. I got rejected probably 10 times a day. Like no, no, no, no, no. So I got really, really, really good at hearing no. And no doesn't bother me anymore. As an entrepreneur, when I was building my business, I got heard no all the time. I got on sales calls that I didn't close all the time, but I was resilient and persistent. And I didn't stop until I got the yes. And I think that that was built inside of me from being an actress and hearing her no again and again and again, and being okay with that.

Read the full transcript

20:27I think one of the most powerful tools that you can own while building a business is being best friends with the word no and being besties with rejection and being like, oh, you're rejecting me. You're saying no to me. Okay, cool. That's just going to motivate me to go for it again in another way. And I'll show you. I had that mindset building my business. And so I never stopped ever. And I still don't ever stop. And I get heard no still to this day all the time when I'm trying to speak on big stages or I'm trying to get to the next level of my business, or we fail at something or don't close a sale or one of our launches doesn't go as well as we wanted it to.

20:59I'm like, okay, watch me. I'm going to do it again. I'm going to learn from that. No, I'm going to take whatever I learned and I'm going to put it towards the next one to make it an even bigger. Yes. That has framed my entrepreneurial journey in a big way.

21:14Ken Wentworth:As we're hearing in this conversation with Scott Clary, entrepreneurship today is really about how fast you can adapt. Whether you're building a business, a brand, or a career, the people who win aren't necessarily the ones following the traditional playbook. They're the ones willing to rethink how value gets created and where opportunity is actually moving. That same shift is happening in investing. Sharp investors are applying that same entrepreneurial mindset to their retirement. That's where BlockTrust IRA comes in. Instead of relying on outdated, traditional allocation strategies, you can move your IRA into Animus AI, an advanced system designed to help identify opportunities and navigate changing market conditions.

21:58Ken Wentworth:Since 2020, BlockTrust IRA's Animus AI has significantly outperformed Bitcoin as a benchmark. Visit writeaboutcrypto.com to get started and see if you qualify for up to$2 ,500 in bonus crypto. BlockTrust IRA, smart crypto investing powered by AI. We're taking the BS out of business, baby. That's the tagline, but it's the truth. And you know what? There's no one better than my good friend, Jamil Damji. What's up, Jamil? What's cracking, brother? Good to see you, man. Hey, man. It's good to see you. What got you in real estate? Where does the passion and the energy come from? It exudes from you.

22:34Ken Wentworth:Where'd all that jazz come from? I accidentally found myself in real estate. I'm East Indian, culturally, heritage-wise. My family had eyes for me to be a doctor or an engineer, but doctor was where I was being groomed to have my life. I didn't get into medical school, which was, at the time, one of the most disappointing and heartbreaking things that ever happened to me. I had worked so hard in college to get a near 4.0 GPA. I killed the medical school interest exam. I did all the things you need to do to pad a resume with volunteering and extracurricular activities that I didn't have time for, but did anyways, because I needed it for my application and the interview process.

23:12And then some dude saw me and said, no, you know, just not today. I saw that as a sign, really, because I had done all of the things that you should do. In fact, I can say it now, but in the medical school entrance exam, the guy who sat behind me cheated off me on the test. I know him really well. He's my cousin and he had partied the night before and needed help on the exam. And I let him cheat off me. He got into medical school. What the fuck? That guy is prescribing you guys all the things and is giving you everything you need right now to survive. He gets into medical school. I don't get into medical school.

23:42That just showed me the disparity in this whole process. This some guy, depending on how he woke up today or who I remind him of or something about me made this guy say, no, it wasn't my testing scores because they were better than my cousins. It wasn't my GPA. It was also better than my cousins. What about me made that person say no? When I saw that, I realized that another human being had control of my destiny and an arbitrary decision could change the trajectory of my life. And I decided then never again. I was never going to let another human make my choices. I was never going to let a human being say yes or no to me.

24:16No, I'm going to pave my own path. I'm going to do it myself. And so that's where the passion came from, was a general looking at life and looking at the way the system is kind of set up and just rejecting it. It was a full rejection of what was paved out in front of me as a way to succeed. I knew I had to take control of it. Now, I find myself in an entrepreneurial situation, which wasn't really lucrative at the time, but it put me in proximity to a guy who was investing in real estate. and I got an opportunity to do my first wholesale transaction, which at the time I didn't even know existed.

24:45There was no online education. I thought I invented wholesaling because of the deal, but I hadn't. I thought I did because I hear from these developers that they're looking for these old bungalows in Calgary, Alberta, where I grew up, that they could demolish. They just needed to have 50-foot frontage, 110-plus feet in depth. They needed to be zoned R2, and they needed to be in specific neighborhoods in the city. Now, I lived in one of those neighborhoods in a rental, and I had tried to rent one of these houses a few months earlier, but I couldn't because it was$200 out of my budget. But it was still available when I was walking my dog the next day.

25:14And I called the for rent sign and I asked the homeowner if they would consider selling it instead of renting it because they had been unsuccessful renting the spot. Her answer was, yeah, for the right price. And I inquired what that would be. She says$350 ,000. And this decision that I make next is what changed everything for me. I didn't go to the people who were looking for that house and say, I can get you this house for$350 ,000, which most people would have done. I went and I asked the question, how much would you pay? And they said$400 ,000. So now I have a$50 ,000 problem to solve because I can buy it for$350 ,000.

25:43I can sell it for$400 ,000. I have no money. I have no credit. I have no way of acquiring this. What do I do? I start talking to my family members. I start asking for a loan. I start seeing who could give me$350 ,000 for a week or two. And nobody wanted to give me any money. I'm the kid who didn't get into medical school. Why would I give him anything? Then I start calling real estate attorneys. And I get all the way through to the letter S. A guy named David Steed answers my call. He's so fresh out of law school. He had no secretary. And I tell him my problem. him. And he's like, oh, that's easy.

26:09That's called a skip transfer. And I'm like, explain. He's like, you take two contracts, one where you're the buyer and you pay$350 ,000 on that contract. And then you take a second contract with everything else lining up, except you're now the seller on that contract. And the new buyer is going to be who the buyer line is. And the price is going to differ because you're buying for$350 ,000, you're selling for$400 ,000. Everything else has to be the same. So the conveying attorney, the condition dates, all of that have to line up for this to work. But once you've got these things signed, bring these contracts to me.

26:36And then I asked, what happens then. He said, it takes me a couple of weeks to do some research, look at liens, make sure that I can convey title, pay off on the mortgage. All of the documents have to be prepared. And once that's done, I'll have a check waiting for you. It happened. I get a$47 ,000 cashier check and coming from a situation where my parents hadn't made close to that in a year in either of their lives. For me, that was the game changer. That's where the scales fell from my eyes and I saw what is possible in life. And I never looked back. I went ham after that and I started wholesaling full-time.

27:07I do really well in it until the financial collapse in 08, where I lose everything because of leverage and just inexperience and doing too much, which is essentially how I got caught up in that. But it was a beautiful education and it taught me so much. That's where I get started. That's where the passion comes from. Because quite honestly, Ryan, I look at life as a series of choices. You see everybody gets a chance to choose something different. Choose something that's outside of your regular patterns and your life is pregnant.

27:37Ken Wentworth:Starting something new isn't just exciting. It's honestly a little terrifying. I remember right before I launched my podcast, all those what if thoughts creeping in. But looking back, taking that leap was one of the best decisions I've made. And I'll tell you, having the right tools makes a huge difference. That's where Shopify comes in. From massive brands to people just getting started, they make it easier to go from idea to real business. You get hundreds of ready-to-use templates, design a store that actually looks like your brand, plus AI tools that help write product descriptions, headlines, even enhance product photos.

28:14Ken Wentworth:Instead of bouncing between different platforms, everything's just in one place, which honestly saves us a ton of time. And that's the part people don't always see. It's not just about building a website. Shopify is the commerce platform behind millions of businesses and 10 % of all e-commerce in the United States. And it's built to handle everything as you grow. We've used it to keep things organized in store and online, run email campaigns, and stay on top of business without things slipping through the cracks. It just makes operating smoother. Start your business today with the industry's best business partner, Shopify.

28:53Ken Wentworth:Start hearing... Sign up for your$1 per month trial today at shopify.com slash Ryan. That's shopify.com slash R-Y-A-N. These possibilities of making different choices. Hey, what better way to take the BS out of business than talk to Mr. Biz himself, Ken Wentworth, author of three best-selling books, a known Radio Master. What's up, Ken? Good to be here, man. You have a popular radio show. Talk about that, where the Mr. Biz came. Talk a little bit about that journey. They had asked me to be a guest on someone else's show to come on as a business expert. They take callers. There was me, there was an attorney, and there was a marketing person.

29:35Ken Wentworth:So business owners would call and ask a question. And depending which one of us, we would answer their question and try to give them help. I was on the show two different times, did a couple of different segments. The GM of the station said, hey, man, I've been looking for someone to host a business-related show for almost a year now. You're my guy. You got to host a show. I'm like, I don't do that. This was fun, but that's not in my wheelhouse. And he said, what I'm finding is I'm finding people who are either super knowledgeable, but they have the personality of a thumbtack or they don't have any depth of knowledge and they're just super charismatic and sound like a used car salesman.

30:03Ken Wentworth:You're a combination of both. I'm like, I'm not sure how to take that, but they finally wore me down. I said, I'll do eight shows and see if I like it. Probably about three or four shows in. I was like, this is pretty cool. I really enjoy it. It's funny. I think a lot of people think, oh, you're a radio show host. I'm like, that's like this much of what I do. That's almost like a little side project thing. I do enjoy it. It's a lot of fun. I get to meet a lot of cool people and talk to a lot of cool people and learn from a bunch of different people as well. A guest I have on the show and things like that.

30:27Ken Wentworth:It's another avenue creating content and be able to put content out for people and things like that. I definitely enjoy it. As a fractional CFO, when you step in, what are people looking for you to help with? And maybe what's some of the most practical outcomes that come from your expertise and what you end up helping businesses with? Typically, I come in as very strategic. My undergrad's in accounting, but it bored me to tears. I worked for the first couple of years of my career in accounting and I'm like, oh my gosh, this is like way too far in the weeds for me. Typically coming in and helping a business, a lot of times they're businesses that probably a lot of people can relate is they've been in business for 8, 10, 15, 20 years and you kind of start to get a little bit of tunnel vision and you start to get the, this is the way we've always done it mentality and having a fresh set of eyes that come in and say, wait a minute guys, why are we doing this?

31:09Ken Wentworth:It's so often and I come into a business, and there's so much low-hanging fruit of ways to improve and make massive changes where managing their margins better in a nutshell, meaning that for every dollar you're bringing in in sales, you're keeping more of it. More of it's ending up in your pocket at the end of the day. And that's not just cutting expenses and things like that. It's a lot of other strategic things to do and making sure you're pricing things. And a lot of people just come in the air and they're pricing things a lot of times without considering what should your margins be on those different things and managing through some of that stuff, ways to increase sales.

31:39Ken Wentworth:This get that mentality. We've always done it this way and picking their head up out of the weeds to like see the forest a little better and a little clearer. When I first started doing this after I left my corporate career, I was like, can I really do this? Can I help people? Can I really make a difference? And then the first client I'm with in 90 days, the change, you could see the transformation in just the first 90 days. And then obviously beyond that. And then the next client I got, it's like, holy crap. It gave me a lot of confidence to say, yeah, I am pretty good at this. It's easy for me to go in.

32:05Ken Wentworth:And I just always thought because everyone has this knowledge. I was in the corporate world. I was in a financial company and there's a lot of financial smart people around me. So I just thought, well, everyone has this knowledge. Everyone thinks this way. A lot of times business owners are really good at the widget they produce or whatever service they're providing, but they're not really good on the business side of things. Increasing sales, increasing your net income, increasing the value of the company, especially now you get a lot of baby boomers that are considering exiting and wanting to sell their company.

32:31Ken Wentworth:How do I improve the value of my company? In my agency now, my role a lot of times with the client is what you just described, because that's my expertise in marketing and branding. It's really almost more that business consultant type role. And I was just sitting here thinking, I'm like, man, I'm going at this wrong. Some of the challenges we have is we're kind of always on the agency side of the fence. They want to listen to me, but unless you're like on the team, even if fractionally, it's hard to get implementation to happen. Half the time we were working with a client, if they would get this, this, and this out of their way or do this, a lot of times that's more than one ad is going to save the day.

33:04Ken Wentworth:This ad could do it and we can write you a great campaign, but that's just going to be a lipstick on the pig. When I'm talking to someone who's a prospective client, and I found this out early on, you got to have someone who's willing to listen and willing to implement. I had one client, that's how I learned it, that given them all these different things to do and change in their business and they're not implementing anything. I really took a step back. I tried some different approaches. I really have to make sure that when I'm talking to someone, the prospective client, that they are going to listen.

33:29Ken Wentworth:I'm not saying everything I say is gospel, like I've got every great idea in the world, but when we do agree on something, that they're actually going to make the change. And so for me, having someone that's an ally in the business, that's not just a CEO, but someone under the CEO, the COO or something like that, that's actually going to be implementing some of these things. It's critically important. One of the things I do that I require for a client, if you have a staff meeting with your leadership team, I'm in it because I want to be part of the team. I want to be perceived as part of the team.

33:55Ken Wentworth:And that way it helps me keep my finger on the pulse of the business. And it gives me a voice at that table to push some of the initiatives that I'm trying to get some of the changes I'm trying to think. Who's picking up on this? Have we made any progress on this? And that made a huge difference, really making sure that I'm involved in some of those key meetings. When they have quarterly planning off sites, I'm there. And a lot of the clients are like, you'll do that. You're not even an employee of ours. I got to be part of this. I want to. And it's going to help me be able to help you better.

34:18Ken Wentworth:It's critically important to be involved. It's so frustrating to have someone that doesn't implement. You just do these two other things. It could be explosive. You don't find us. Ryanisright.com. You'll find all the highlight clips and the full episodes from today, including the YouTube video. We've got some exciting things coming on the video side, and I'm always at Ryan Alford with that blue check before you can buy it. We'll see you next time on Right About Now. Here's the truth. Information doesn't change your life. Execution does. So don't just listen to this episode and move on. Take the idea.

34:49Ken Wentworth:Make the call. Launch the thing. Fix the problem. Build what you keep talking about building. For more, follow Ryan Alford on Instagram at Ryan Alford and watch or listen to every episode at RyanIsRight.com. This is Right About Now. Now quit waiting. Go win.

From the publisher

Every entrepreneur talks about the breakthrough. Fewer talk honestly about the rejection, chaos, and setbacks that come first.

In this themed compilation episode of Right About Now, Ryan Alford brings together powerful moments from conversations with Alex Morton, Jen Gottlieb, Ken Wentworth, and other guests who know what it means to rebuild, reinvent, and push through resistance. The result is a sharp, motivating episode about what really creates traction: resilience, self-awareness, better decision-making, and the willingness to execute before you feel ready.

Ryan ties these conversations together with the bigger lesson behind the show: breakthroughs do not come from consuming more information. They come from acting on the right insight at the right time and refusing to stay stuck.

Topics Covered

Rock bottom moments that became turning points

Why rejection is often the start of real progress

Authenticity, confidence, and reinvention in business

The first win that changes how you see opportunity

Strategic financial thinking and margin improvement

Why execution matters more than motivation

How Ryan Alford frames resilience across every industry

Connect

Ryan Alford / Right About Now: RyanIsRight.com

Social Media: @RyanAlford

Join our newsletter: https://ryans-newsletter-148404.beehiiv.com/

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