Cut The Tie | Own Your Success

“What Am I So Afraid Of?” — Reid Chong on Facing the Unknown

Thomas Helfrich

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Cut The Tie Podcast with Reid Chong

What happens when you finally stop long enough to ask yourself the question most people avoid?

In this episode of Cut The Tie, Thomas Helfrich sits down with Reid Chong to unpack the moment he realized fear, not lack of ability, was the real thing holding him back. After years in software sales and multiple failed attempts at building something of his own, Reid hit a breaking point that forced him to confront a simple but uncomfortable question: What am I actually afraid of?

That moment led to selling his condo, packing his life into storage, and spending 18 months traveling the world. Along the way, Reid redefined success away from titles and income and toward freedom, time ownership, and living without constant guilt.

This conversation is for high performers who look successful on paper but feel restless, boxed in, or stuck waiting for clarity that never seems to come.

About Reid Chong

Reid Chong is a former software sales professional turned entrepreneur and consultant. He now helps small businesses automate operations using AI and smart systems, focusing on simplifying technology so owners can reclaim time and reduce friction.

After stepping away from the traditional career path, Reid rebuilt his life around intentional action, systems thinking, and freedom. His work today sits at the intersection of technology, efficiency, and personal ownership.

In this episode, Thomas and Reid discuss:

  • The moment Reid asked himself, “What am I so afraid of?”
  • Why fear thrives when it stays vague and unnamed
  • Selling everything without a perfect plan
  • How travel reshaped Reid’s definition of success
  • Freedom as time ownership without guilt
  • Stacking small wins to rebuild confidence
  • Why systems matter more than motivation

Key Takeaways

  • Fear keeps power when it stays undefined
    Naming it creates forward motion.
  • Action creates clarity, not the reverse
    Waiting to feel ready keeps you stuck.
  • Freedom is being able to step away without guilt
    Time only matters if you can enjoy it.
  • Momentum is built through small, repeatable wins
    Progress compounds when you keep showing up.
  • Systems outperform willpower
    Structure carries you when motivation fades.

Connect with Reid Chong

💼 LinkedIn: https://www.linkedin.com/in/reid-chong07/
🌐 Website: https://www.getateam.ai/

Connect with Thomas Helfrich

🌐 Website: https://www.cutthetie.com
💼 LinkedIn: https://www.linkedin.com/in/thomashelfrich
📧 Email: t@instantlyrelevant.com
🚀 Instantly Relevant: https://www.instantlyrelevant.com


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SPEAKER_01:

Welcome to the Cut the Tie Podcast. Hello, I am your host, Thomas Helperk, on a mission to help you cut the tie to whatever it is holding you back from success. And as I always say, you need to define that success yourself. Otherwise, you're just chasing someone else's dream. Today I'm joined by Mr. Reed Chong. Reed, how are you?

SPEAKER_00:

Doing well. Thanks for having me.

SPEAKER_01:

I appreciate it. You uh you want to take a moment, introduce yourself, where you're from, what you do?

SPEAKER_00:

Yeah. Uh my name is Reed. Uh, I spent about I don't know, maybe 10 plus years in software sales. Took a little break from that to go and figure out my own things, and we can talk a little bit more about that. Includes like 18 months traveling the world. So, you know, hiked Patagonia and Machu Picchu, road motorcycles in Vietnam. Um, kind of just the typical find yourself and figure out what what the hell you want to do next. Um, so yeah, that's a little bit about me. And what is it you're doing though? Like so what what are you doing today? Right now we're helping um small businesses automate a lot of their processes and leveraging AI, right? AI is the hot topic nowadays, but a lot of it is just simple piecing together automations and and leveraging, you know, smart stacks. So I work with businesses, consult with them to find gaps in their processes and their and their automation pieces that are um, you know, bottlenecks for them. Uh our motto is if you do it twice, we can automate it. And so we're really just going after that and helping people leverage the hot topic of the day, which is which is AI.

SPEAKER_01:

Yeah. So it's a consultancy. So you work with them intimately, kind of like identify a few processes to start and and then build it from there.

SPEAKER_00:

And then we can build it from there. It's anything from, hey, do you have a website? Do you need you know lead funnels, all that, to we can build out full automations to um, you know, custom avatars and and client avatars so you're communicating with your out your clients 24-7.

SPEAKER_01:

All right, here's an AI that you can give me and everyone else's advice who pays about$250 a month in accounting. What AI tool out there could just take the credit card stuff that I give it, classify it, and I don't pay an accountant to do this shit every month.

SPEAKER_00:

That's actually a great question.

SPEAKER_01:

That's because that should be so easy to do because they do it every month the same way.

SPEAKER_00:

I agree with that. I I think there's a couple already out there, like agent check open AI just rolled in their agent mode. Now, I've been playing with it a lot, but I'm actually my only hesitancy there is do I want to give it my credit card right now? And that's where I'm like, that's where I'm I'm I'm pushing the brakes right there. But I dude, I think we're credit card, yeah.

SPEAKER_01:

Bank accounts, no. Credit card, yeah, yeah. This is just give me a new one, block it, right? The the bank accounts, but but the you think about that, right? So my background being intelligent automation AI consulting for 10 years for big four, you know, or 20 years of consulting, 10 years of it being intelligent automation AI, I 100% know what you're talking about with automating processes. I think the difference recently, though, is with so many little agents and smaller technologies, small businesses actually now can take advantage of this, but don't realize they can. And I think what you guys have positioned yourself from from from my general stalking of the stuff is you guys are really dishonest. There's a strategic component, but you get it done and get them to use it and then build from there. Is that fair?

SPEAKER_00:

A thousand percent, a thousand percent. It's like you said, it's it's simplifying the terms, right? Like things have been common within the SaaS space and tech space, like we're using CRMs all day, every day. But what about like a you know, a nail salon or a med spa? Like these things are kind of revolutionary for them. They don't know that they could, you know, have some sort of automated um calendar invites going out and tracking their, you know, invoices, et cetera. So it's almost like the technology is is we're able to diversify, like you said, to everybody out now and and make it simplify terms for them to understand.

SPEAKER_01:

Yeah. Um, it is a competitive space. Uh what do you think kind of the unique identifier or for you guys? Like what why why should they pick you?

SPEAKER_00:

That's a great question. Um, I don't want to dive too much into the secret sauce just yet, but we are um we've been running a lot of like um doing a lot of research, a lot of back-end studies, seeing what people are searching for, seeing where they're you know, paying across the country. Um, so we're doing very targeted uh marketing towards them. We're rolling out a YouTube channel here soon, um, and just really want to become the voice of small business owners who need to look for simplified um AI and technology terms. I think a lot of the stuff right now, especially on YouTube, maybe it's just the circle that I'm in and you know, the the echo chambers that we're in, but a lot of my Twitter feeds and my YouTube algorithm is targeting people like me. It's like, how can you leverage these software tools to find clients, et cetera, et cetera? But what if you're already a business owner? And that's the, I think, the gap right now of what we're seeing in the market. There's not a lot of people who are simplifying. I'm hesitant to call it dumbing down, but it's it's making it more understandable for everybody else to understand.

SPEAKER_01:

Yeah, I think dumbing it down is it is it because people come in with the techie talk and then the business owner's like, yeah, go away. And if you're like, I'll take your process, make it faster, more reliable, and give you more time and make more money, they're like, Got it, do it.

unknown:

Yeah.

SPEAKER_01:

Obviously, for dumbing it down, it helps because otherwise people don't buy because they become confused, uh, for sure. Uh, you've had a cool journey. Uh, and I want to talk about your your travel and how it relates to kind of how where you where you you know, why you took it, but just start first with your definition of success.

SPEAKER_00:

Yeah, I think, you know, when I was younger, that was the bank account, right? And it's just a ticking talk, like the the ticking timer in the bank account. And traveling and getting to see people around the world and um people with a lot less than me, it really changed that definition for what success looks like. Um, it really comes down to freedom. It comes down to spending the time and and the day how I want. Um, one of my barometers essentially is can I go to the gym at you know noon or one o'clock in the afternoon and not feel guilty? Can I step away from my computer and take a 30, 40 minute walk? Uh, I live here in San Diego. So it's like, can I walk to the beach and not feel like my life is on fire and everything's on fire? If that's okay, then I'm I'm wealthy, I'm I'm successful, everything's that's everything's okay.

SPEAKER_01:

That's great. I mean, and captain of your own calendar is a very common answer. Uh, but you've added an element which I love is not feel guilty. Uh, because like, you know, I a friend of mine's like, hey, do you want to go play golf Friday? And I'm like, man, I'd love to, but you know, I got meetings, I don't want to move, and I'd feel guilty for not missing these business opportunities. There's sometimes you do, by the way, as an entrepreneur, just say, F it, I'm I'm sick today, and you're not, you're just like, I'm sick of working, and you just blow out your calendar. I've done it plenty of times and not feel had been guilty because I needed the day for myself. Where you do that at a job and all of a sudden you got HR involved. So, you know, I'd like you, but I love that. And you know, you shouldn't feel guilty if you've done your business, done your work. It's the point, right? Is be able to take that time and enjoy it and have a beer or or sit there and chill and um smoke a J. I don't know whatever you're into, it doesn't matter to eat 50 yummies and not be able to get home. I'm all cool with all those things.

SPEAKER_00:

That's great.

SPEAKER_01:

Uh talk to me about something. So uh tell me a little about your journey to get to that definition of success and what's kind of been the biggest thing holding you back, the tie, the metaphoric tie you got to cut to get to it.

SPEAKER_00:

Yeah, I think, you know, growing up, um, success was uh, you know, very A-type achiever type personality, right? So it's I want all the accolades, I want all the money, I want all the titles, I want all the things. And very early on in my career, um, I was um at a pretty large company and I was doing pretty well, and I was the most miserable I've ever been. And I had a great manager who would just sit with me and talk to me and be like, hey, I think um this is a little bit deeper than just the work stuff. And that really started me on this path of journaling, um, you know, podcasting, books, et cetera. Um, and it really was the turning point. I I can pinpoint in 2021, sitting on my bed, super depressed, just like, what am I doing with my life? I tried this failed startup, I try this field business. Um, do I have to go back and get an adult job or what am I gonna do? Um, and I had always had this dream of selling all my stuff and going and living on the road and going to Airbnb's. And I would talk about it all the time. I would tell all my friends about it. And I thought about it when I was sitting on my bed and I thought, what's stopping me from being that type of person who takes action and does it? So I did. I listed my apartment or my condo and it sold that weekend. This is back in 2021, of course. So it's like everything was selling like crazy. And I just packed all my stuff up in a storage unit and I left for Europe. And that shift of stop worrying about what's could happen, the fear of the unknown. I I sat down and I wrote down, like, what am I so afraid of? Right.

SPEAKER_01:

I interrupted, but that's a great exercise of I did because once you've identified the fear, now it becomes an excuse because you the fear excuse cycle is vicious. I won't do this because of this. I don't do this because of this. As soon as you get rid of the becausees, you're like, I'm gonna go do this.

SPEAKER_00:

Yeah.

SPEAKER_01:

I know that interrupts that is so so few people actually write down what is what am I afraid of and actually write it. So good for you. That's a like take anything away from the show. We can end it now. Go do that, hang up, you can stop listening. Well, we gotta let them stalk you first. We'll do that here in a minute, but keep going, please.

SPEAKER_00:

No, but but it you're you're spot on. It's what's stopping me from being, you know, I've always considered myself a man of action, and I, you know, biased towards action, but um, what what's stopping me from actually being that person and being that identity? And so that's what I did. And um doing one hard thing, it leads to another and another and another, and you just you you you just stack wins. So yeah, I'd say that's rolling it all into one. That's that's the cutting the ties, that's changing the mindsets, it's all those things.

SPEAKER_01:

I find like some days, uh, this is the analogy I'll use, but it, you know, like this week, especially. My my wife's in Europe for a few weeks, uh, you know, for a wedding and some friend stuff. And so I have three kids, first week of school, and I go to the gym after getting them ready, and I'm not, you know, just whatever. And I know I'm in there, and only reason in my mind I'm like, today is a non-zero day. I am here, I'm gonna do whatever I can just to move it forward, keep it there. And I still see a success, even though I like I just don't have it today. And I know I'm gonna do the bare minimum just because I don't even want to be here. I'm tired, I'd rather go to bed. Do you feel that same way in that kind of stacking? It's like that's like the days that I go there that I barely lift weights are the hardest days versus the ones where I actually push myself and leave, like, I'm gonna be wrecked for a week. Um, that's a harder day, but the harder is a show up when you don't want to. Is that how you describe your kind of like show up, keep it stacking as well?

SPEAKER_00:

Thousand percent. You know, it it's so cliche, but it's it's the atomic habits, it's the little by little. I think of um Arnold Schwarzenegger, his book, uh Total Recall. He says everything, whether it's working out in the gym, relationships, business, real estate, he he he did it all, right? Movies, it's all reps, and it's just doing the reps repetition every time and you go to the gym. It's you don't get strong because you lifted super hard one day, it's because you did it for years and years and years, and exactly what you're talking about.

SPEAKER_01:

I mean, in Ellis Horses Nigger's case, it's doing it years and years and taking a lot of steroids to enable yourself. So I'm okay throwing some steroids in your business because the truth is who cares? Like, truth, if that's your choice, go do it. Now it's legal, it's called men's clinics, guys. Just look into it, it's great. Shit's cleaner, it's not from monkeys, it's great. See what I did there? I just train wrecked our our podcast just in one swell. I love it. No, I love it. But if I didn't do this, it'd be boring. And not that our conversation isn't, but you just never know what's gonna happen. Let's continue the journey here. Um identify your journey, you just identified you identified like how and what, and you even talked about how you did it by writing down the fears, which is a big step. I I can't I'll go back to that. A lot of people don't do the how very well, and you said F it, here's what I'm doing, and you did it pretty fast. I mean, you sold a condo in a weekend. I'm just gonna put that out there, guys. I'm doing it, sold it. Shit, I gotta go. I mean, like it's like it was in motion, and and I love that. Uh as you did it though, do you do you feel like I'm gonna ask you differently, what do you think you're most grateful for in this moment today?

SPEAKER_00:

Well, that's that's a loaded question. There's everything, all of it. I mean, everything, and that's again so cliche, but every single thing has gotten me here. And it's an iteration, it's figuring shit out, excuse me, it's figuring things out. Um, you know, it's not perfect every time. It's it's and when you're in it, it's so hard. And it's like the hardest thing. You know, it's like like I joke about this all the time. Like my my nieces or my nephews, when they're in high school, high school is their world. And so it's feels so end of the world when something happens. And I would tell them, I'd be like, don't worry about it. Like, you're gonna get out of high school and things are gonna be, you're gonna get into the rule and you're gonna see it's amazing. And when we're in it, it feels this is all I can think of. This is all I it's all consuming. And you get past it and you realize I'm so grateful for that. So to answer your question, I'm grateful for it all, like the ups and the downs. It's a human experience, but it's what makes me appreciate those days and and all the things.

SPEAKER_01:

It's you know, things happen for you, even when they were happening to you, and you come out with it and uh and you you're you're you're you're spot on there uh with it. So I I love that. That's a it's a beautiful place to be in the mindset. Uh and in and it's one you have to choose, to be fair, uh, to be there. I will go back though, I will tell people who are listening, you know, you can lose a parent, you can lose a friend, some people have lost children, uh, you know, you can lose an arm. Uh those all are horrible things that can happen to you, and you can try to find the best with it. The thing that doesn't happen to everybody, by the way, is don't do things into it puts you in prison because then it truly is over. So then you can still make the best of it, but it's gonna be it's gonna be like don't do things in you somewhere that you didn't need to go. Like you can you can get over much things, but if you're locked in a cell for 50 years, sorry, it's gonna it's gonna change your trajectory just a touch. Don't do things illegal. All right, at least big illegal, you know what I mean? You speed, you get a ticket. Don't do embelly. Okay.

SPEAKER_00:

I just want to hit on that really quickly. It's funny you mentioned that because uh I'm from Washington. I grew up in Washington, went to high school out there, and I went back to visit a couple years ago, and I got a news article sent to me about somebody that I know very close to me in high school that's in jail. And that is like one of the biggest like, where did our roads diverge? I was with this person literally all the time. Um, and what got me here, you know, and what got him there? And and and so that's again reflecting on those types of things and doing things now for me because I recognize that not everybody has that freedom or these opportunities or this education or all the things that I take for granted. So that's another piece of gratitude.

SPEAKER_01:

It it's amazing when you see that because there, there's a I tell my kids this, and you have a sophomore and a couple of younger ones that are going to go through it. And I said, there's a big divergence that happens in high school. You're all friends, they have groups who go to college, some people take trade, other people drift, right? And if you don't have your and you don't have direction at some point, it doesn't matter if it's you know, if as long as it's a positive direction, you're in a good spot. If you're in a no direction, manually wondering, you are in a bad spot, you are vulnerable. And it's it's like in nature, right? If you're not with some pack of some sort, you have no protection at all. Um, and I think people need to know that. Like when you, especially younger people, in any age, you you do need to get direction, or you're gonna always be vulnerable at some point. And I think it'd be 30s, 40s, 50s, whatever. Uh, because there are these different divergent points that happen, I think, throughout your life. Uh let me ask them, is there anybody in your life you can't forgive?

SPEAKER_00:

Uh I don't know. I I think I'm at the age where I'm just like, I don't need to deal with this, and so maybe I just move on with it. Um, I mean, I'm sure there's there's things, but for me, it's just like, hey, we can move past it, and uh it's not that big of a deal. Um, I try not to hold on grudges, but I also know that I'm probably a knock on wood here. There's probably things that people are saying about me that I could probably do better about, but not life, right?

SPEAKER_01:

Ladies and gentlemen, we've uncovered a tie we'll need a cut and work through therapy on. We're gonna come back to that. I don't want to hear the other thing. He was like, God damn, I'm not answering that one here. Talking about mom and dad, cousin Jane, whatever her name is, doesn't matter. Um what's the uh the one must-read book? I think you talked about one or two better, but what would you say entrepreneurs out there? You gotta go read this one. What is it?

SPEAKER_00:

You know, my my common answer is um David Goggins can't hurt me. Um, and I think everyone's familiar with him. Goggins has really blown up lately. One that I think is a little slept on is Open by Andre Agassi. Um it's it's his story, it's it's seeing him throughout his career. What I love about it is that we're talking about one of the arguably one of the best tennis players ever through history, right? World number one, he was at the peak.

SPEAKER_01:

Best backhand ever. Man, it was wicked.

SPEAKER_00:

And the mindset and and all the things. And you read about his mindset, and he hated it. You hear him talking about he had to take a 20-minute cold shower before his match to get him hyped up. To and this is like this is like peeking into the sh into the mind of LeBron James. You know what I mean? Like this is insight that we don't really ever get to. And so I think like the biggest takeaway for me, and and how it applies to anybody, founders, etc., it's like we see these people, we put them up on a pedestal, we see them on TV, we see them on the pedestal and holding the trophies, and we think, man, that guy is he's he's gotta be amazing. He's so brave, he's so strong, he's so smart. I can never inside his own head, he has those same secure insecurities and fears and all those things, just like me. So if somebody like that can do it, like why can't I?

SPEAKER_01:

It is amazing too, and actually, I'm gonna tie it back to what your business is. Uh, you I think you should love this. This should be a post for you. Here we go. Free content. Is that Andre Agassi uh was successful not because he had uh passion the whole time, not because he even had willpower the whole time. He had plenty of demons, uh, and he had to shave his head. He went from gorgeous hair to that was probably the anyway. But the real story is he had a process and he had a process for winning. And he's like, it's so no matter what he was doing, he figured out a way to get it done, regardless if he wanted to be there or not. And I think if you have a really good process, and I'm tying it back to yours in intentionally, as long as it works, it's gonna work. And and and I think that's a really important piece just in your own business. Get a process in place and do it over and over and over, and then you at least can adjust, and and that way you're showing up, you're getting the stuff done. Um, and I think that's super important for just winning in life um as well. Um, anyway, so enough by the way Chris Chris Boll, you know, like one of the uh uh one of the Steelers primary, you know, kickers is Chris. He's I played golf with him and he's like, I hate football. So I had a 24 million dollar, like all-time I hate football. It's stupid. I'm like, and he's a pretty good golfer. And I was like, really? I was like, he's like, yeah, it's dumb. He's like, I don't, I don't, I love the money. He's like, I don't like kicking. I just happen to do it well. And you can see he's like, I really don't like football. It's dumb. The the politics, the game itself. You make 24 million a year kicking.

SPEAKER_00:

People process, agree. The system uh we fall back on the systems on our habits, right?

SPEAKER_01:

It's like 100% sure true. Um, what's some of the worst business advice you've ever received? Gotta bless a telephone coming out on that.

SPEAKER_00:

I I don't know if I I don't know if I can say specifically bad advice. I think it would be just maybe eight bad examples, right? Things of not to do. Like one of my very first startups I ever joined. Um I just saw a lot of what not to do, right? Firsthand, like buying expensive cars and um Louis Vuitton bags and all that kind of stuff. And it's like, for for what? Like we could blow the business up and invest in ourselves and invest in all these things and make that money work for us. And you just wanted to have a cool car, all these things. So I would say it wasn't explicitly told to me, but it was shown to me. And I think that was the bet the biggest lesson for me.

SPEAKER_01:

Yeah. I've met uh a number of founders who said even that after they've exited the vanity phase that they go through because they've always wanted it and it has zero value once they get there. Um but I've seen other you know companies be worrying about like where they're having dinner for Christmas and it's not nice enough and let's go spend a half a million for one evening for the whole I'm like that is a waste of money. Why don't you just pay for one's healthcare for the year? Like that would be where like like go pay for that and give everyone an extra you know week vacation during the holidays and just tell your customers we don't work during this time go take off time too. Everyone the world will turn right and that be that mindset of of what can you do with the money that actually has value to build put it into your people put it into don't put me I understand salaries there's a math problem there but put it into people to something that actually gives them value or you know keeps them there that they're good. So you know I'm with you on this mic I could completely mic whole podcast on that like not just this one another one. Thank you. Oh if there's a question by the way I should ask today and I didn't what was that question?

SPEAKER_00:

I I think you really touched on it. I mean it's it's what are we here for? What are we doing? What's the motivations behind it all? Um you know it's an over it's not chasing anymore. It's more of just like I'm capable what's let's get after and see what we can achieve. I think that's been like the biggest unlock and shift for me. It's not from like a position of like I need to prove it or show anything wrong or or prove anybody wrong.

SPEAKER_01:

All right I have one more question. What was your favorite place in Europe you visited and why favorite place in Europe?

SPEAKER_00:

I love Amsterdam um outside of all the reasons that you would consider um it's incredible. I mean the architecture the the canals the boat like it's just riding bikes every single day there's so many parks and greenery um the the people are are friendly they're so quirky and interesting I think I think Dutch people are very fun especially when you compare them to like German sorry not to say anything but like German people in typical are more serious uh and I think Dutch people are a little bit more loose and and fun. So I love Amsterdam. I would I could see myself living in a a little narrow house on the canal.

SPEAKER_01:

Yeah it's be it's it's it is a cool place. The marketplaces all the pieces there and I've been there several times I've actually never been to the red light district because I'm like I feel like I would be disappointed and feel like I need at least one shower after I walk through it. So we would it's kind of gross. We'll we'll go down that road uh so people can properly stalk you after the uh show here um who should get a hold of you and how should they do that?

SPEAKER_00:

Yeah so LinkedIn's probably the easiest you can find me on LinkedIn um the website is getateam.ai um we are like I kind of teased earlier we're starting to roll out the YouTube channel here soon um and that'll be your go-to resource for anything with the latest of AI technology how to simplify it how to apply it to your business um we really just want to be a free educational source and um just offer as much value as we can more thank Reed thanks for taking a few moments with me today.

SPEAKER_01:

Appreciate it. Yeah that's great. You get to the beach today a little later and don't even feel guilty about it. Thanks. Hey listen anyone who was still uh you're still on with us thank you for getting here if this is the first time you've been here I hope it's the first of many get out there go cut a tie to whatever's holding you back from success. Define your success first though so you are chasing your dream and not somebody else's.