Calvin Wayman Gives Up on Being an Entrepreneur, Almost

Calvin Wayman, a successful entrepreneur, author of Fish Out of Water, host of the podcast Curious with Calvin Wayman, and star in the YouTube series Making a Millionaire,

In this episode, he welcomes me into his kitchen to discuss the journey from polygamy to prosperity.


  1. Get the Calm app, pick up guided meditation.

  2. Become a member of the CIA. Consistent Imperfect Action.

  3. Make a decision, then make it right.

Episode Links:


Fish out of Water - Calvin Wayman



Curious with Calvin Wayman

Social Media



FaceBook :

The Calvin Wayman

YouTube :

Making the Millionaire


Q: Help us understand what the “aha” moment was for you when you decided that polygamy was not for you.

A: I remember the day the whole ideology cracked for me. I went to a college class, as the first of 45 siblings. I’ve always been curious. We got to take electives, and I took a philosophy class. The theme of the class was based on The Matrix, and one of the first sessions we heard a story, Plato’s allegory of the cave. After we heard this super interesting story, our professor asked, “Who are you in the story? Can you honestly say that you’re the person seeking truth, leaving the cave? How do you know you’re not someone chained to a chair, and your reality is just projections made by someone else?” That made me go, “holy sh*t. I’m the guy chained in the cave.”

Q: What was your transition like once you decided you were going to leave that life?

A: It’s been a long road. That class was almost 10 years ago, and I have only officially left the religion a year and a half ago. First hearing that story completely scared me. Who was I going to talk to? I was afraid to talk to my family, and my professors. I just studied a lot. What came out of that was me quitting my day job in Utah and moving to Southern California. There, the shift become easier and more dramatic. I learned the world was a lot bigger than I thought, but there’s a difference between understanding that intellectually and experiencing it. Not being in the echo chamber that I was used to accelerated the process. I had to become more honest with myself. There was so much fear, I had to face hell.

Q: Did that decision to leave help you with your entrepreneurship?

A: The entrepreneurship thing came first, so I think it was the other way around. I was already doing some of the things I mentioned in Fish Out of Water, things that were stretching my capacity of belief, like quitting a secure day job and moving to Southern California really stretched me. I also did other things that stretched me, like Spartan runs and signing up for marathons. That all helped me to make the difficult decision to leave my religion.

Q: So all those things that pushed you into discomfort encouraged you?

A: It gave me the courage to make that step. In hindsight, I didn’t have a lot of practice trusting myself. In religion, the people who had the answers never was you, it was books, God, other people. Don’t trust yourself, because you don’t know if Satan is trying to trick you. The practice of pursuing my dream to become an entrepreneur gave me the courage to say that I wanted to go after something I believed in.

Q: In your book you talk about finding your gift and going after it. What do you think your gift is, and how did you find that?

A: It’s an evolving thing. The reason you need to know it’s evolving, is because you need to get into action to find it. Your palate is going to evolve, and it’s true. You can only find your favorite food by trying out a bunch of different foods. Go taste some stuff, that’s how you figure it out. When I quit my day job, the only thing I knew was that I didn’t want to be an employee anymore. It was death to my soul. After I quit, the first thing I thought I’d do was become a sales trainer. After I started it, I realized, my gift was something else. I realized the reason I liked being an entrepreneur was because it was a way to help the world now. I moved from Periscope to Prosperity Loop, that gift evolved over time. Today, I’d say my gift is that I’m curious.

Q: There’s a debate amongst the entrepreneurs between whether you should burn the boats or save the bridges. What is your perspective?

A: Burning the bridges, to me, has a context around relationships. I’m not a big fan of saying “f*ck you” to someone. When it comes to burn the boats thing, this is a huge conversation. Should you burn the boats to go after your thing? I think this is a self-awareness thing. You need to see what works for you. I’m a fan of burning the boats. I have a lot of faith in people, and when they HAVE to figure it out, that’s when they do.

Q: How do you suggest they escape those areas of wantrepreneurship, the analysis paralysis and the planning purgatory, and get into the entrepreneurship?

A: I think we’ve been conditioned to think that everything is supposed to be perfect, and then we become our own worst critic. In entrepreneurship, and life, I believe that there are multiple answers. I was noticing a pattern in my life. Year after year, what changed? Not much. What if that pattern continued? What if I wake up in another 10 years, and I’m not only in the same spot, but I’m more stuck in a stranglehold, or even worse, the fire that I have to do something died because I never acted on it? That scared me. The thought of that happening made me say screw it, I’d rather try and fail, and I have to believe that if I do this for 10 years, following my calling, that I’d be in a better place than doing something safe and secure for 10 years.

Q: What was the most memorable moment of failure for you, that in hindsight, is like “that is why I’ve led to my biggest success to date.”

A: There was a time during my door-to-door business, where I was doing everything “right,” but nothing was working. I was working my ass off, I was showing up, knocking on doors, throughout my training and stuff, we were getting at least one deal a day.

So I knew if I hit enough doors, I’d get at least one deal. So I was hitting a lot of doors, like 45-70, and that’s a lot of rejection. And that’s why you need to get that one deal, otherwise you go crazy.

I put my entire family in a U-Haul, and I was making no money, and I agreed to pay rent that was 3x what I was used to in rent, betting that I’d make it. I go knocking by myself, day one after I moved, I was on fire, going door to door, but I was getting nothing. Day two, zero. Day three, zero. I started to question everything, myself, what I was doing, but I had this weird moment, questioning if I should go back, but I said I should keep going. Day four, door after door, still zero. Day five, still zero. The terror, mixed in with a weird numbness. I was so confused with all of reality. I had a phobia of dogs at the time, and the only things I saw were people slamming doors in my face, and dogs I thought were going to eat me, what if I went into a gated community and someone calls to tow my car, there were so many fears. On day seven, I knocked on a guy named Frank’s door.

I’ll never forget Frank, and he did something amazing.

I gave him the whole pitch, was was amazing, and I was selling solar, which I thought was a good idea in Southern California, but turns out a lot of other people had that idea too. So I gave him the whole pitch, and he said “This sounds like a good idea, yeah.” And he bought. And a feeling of relief came over me. It was real money.

It was worth to keep going. So I took his information, and then I just had to call the Public Utilities company with his information. So I called them, gave the information, and gave Frank the phone, to confirm his information. He said, “you know what, even if it’s a soft credit check, I don’t know why I’m paying without panels on the roof. Cancel everything.” I grabbed the phone from Frank, I told him, this is just to make sure you pay your bills on time, this is nothing. It’s all good. I gave him back the phone, he puts it up to his ear, and we’re just staring at each other, awkwardly. The weirdest 15 seconds of my life. It felt like 15 minutes. And then Frank says, “you know what, Calvin talked me back into it, so I’ll do it, but I hope your CEO is listening because I think it’s dumb to have anything to do with your credit this early before panels are on the roof. Actually, I just talked myself out of it this time. Cancel everything, you have my email, right? Send me an e-mail confirmation showing me that you’ve cancelled it.” Click. “Sorry bro.” And I left.

I went in my car and I lost it. “If this is what going after your dream feels like, I don’t think I can do this.” I actually ended up working the rest of the day, getting nothing, and I left the neighborhood so pissed, so hurt, almost betrayed.

“Seriously God, why is this happening?” And a little voice came to me, and said, “Go back to Frank’s house.” Why would I go back to Frank’s house? Besides, he already said no. Then it occurred to me, go back to your phone sales days. You’ve turned some no’s into yeses. He already said no, what do you have to lose.

I went back to his house. It’s dark at this point. I ring the doorbell, and give probably in the history of closes, the most pathetic close you could ever give, and once he came out, I just said, “Frank, why don’t you just do this?” He starts to smile, comes out, and says, “Calvin, you know what? I’m gonna do it.” I got really confused. I went, “what did you just say?” “I’m going to do it, but let me tell you why. Now I’m an older guy, I’ve been around a time or two, and I know that the people that truly succeed in this life are the ones that just decide to never quit, and never give up. And so I’m going to do this, not because of solar, or the credit check, but because of you. Because you didn’t quit. Because you came back, I’m going to give you the order.” And he did, that time. He puts his hand on my shoulder, makes me look up at him, and he goes, “Calvin, I know you’re working your ass off, but don’t quit, keep going. Make the decision that you’re never going to give up.”

Q: What was the day that you decided to put in your notice at your full time job?

A: It was early 2015, in February, so I just crashed the four year mark.

Q: With getting to the four year mark of diving headfirst into entrepreneurship, what would you say is a behavior, belief, or habit that has become non-negotiable that has helped you keep growing and evolving your gift?

A: Meditation. I did not have that habit back then. I picked it up during the door to door stuff, because the head chatter was so loud. When you’re going through stuff, a lot of people are picking it up because it is a popular tool, I picked it up because I needed it. It’s interesting, because at first it made me feel worse. But before, if I was having these feelings, I pushed them away, and during the guided meditations, it was bringing them up, and I had to feel them, deal with them. Doing things like that to unplug and reconnect with yourself is huge to me. Meditation daily, and once a week I do a reset, where I unplug from everything and reflect on the week’s accomplishments, and reconnect with my year’s vision, planning towards that. Once a quarter I do a recalibration, I disconnect from everything for about three days, no email, no social media, no responsibility, not even conversations with my family. I know people who have had profound experiences just doing this for a day. I usually go somewhere outside of my usual routine, I like nature.

Q: What is the best way to get in touch with you?

A: Instagram is the best place, it’s just Calvin Wayman on Instagram. The podcast, Curious with Calvin Wayman, is on Spotify, iHeartRadio, Apple Podcasts, wherever you listen to podcasts.