What happens when you’ve already built a successful freelance business?

You could keep doing what works.

Or you could ask a more interesting question:

What else might be possible?

Ross Simmonds grew up in a small community in Nova Scotia without an elite marketing network or proximity to the usual centers of opportunity. He went on to build a multiple six-figure freelance business, found the B2B content marketing agency Foundation, build a 50+ person team, write Create Once, Distribute Forever, and become CEO of Distribution.ai.

Ross doesn’t describe that path as a series of perfectly planned career moves.

He describes it as compounding.

He kept creating. Experimenting. Learning. Meeting people. Doing good work. Putting ideas onto the internet and seeing what came back.

One of his operating beliefs is simple:

Give value to the internet, and the internet will give value back.

That philosophy becomes especially interesting when we talk about content.

Ross believes most content collects dust for a deeply human reason. We tell ourselves we’re too busy to promote our work.

He thinks we’re mostly afraid.

Afraid of repeating ourselves. Afraid of looking like a try-hard. Afraid of annoying people. Afraid somebody will disagree with us in public.

So we press publish, get the nice little dopamine hit from finishing something, and immediately start creating the next thing.

Ross offers a different frame:

Publish is halftime.

The second half is distribution.

Take the podcast, article, case study, video, or idea you worked hard to create and keep finding useful ways to put it in front of the right people.

Because being excellent and being known for your excellence are two different things.

We also talk about video as an underused opportunity, how to participate in communities like Reddit without barging in like a marketer with muddy shoes, why public speaking created enormous leverage for Ross, and what AI does—and does not—change about expertise.

Ross’s AI take is refreshingly non-apocalyptic: AI makes good people faster at good work. It makes exceptional people faster at exceptional work. But it cannot manufacture the taste and judgment you never developed.

Your craft still matters.

So does doing what you said you would do.

So does becoming a slightly better human tomorrow than you were today.

That’s a much bigger conversation than writing better LinkedIn hooks, and I think that’s exactly why it belongs here.

Note: This conversation was originally recorded for the Advanced Freelancers Summit in May 2026.

Key Points

• Your current ceiling may not be permanent. Ross grew his career from a small town by refusing to assume geography or a lack of connections determined what was possible.
• Think in compounding, not career ladders. Freelancing, agency ownership, investing, software, writing, and speaking became interconnected layers rather than isolated career moves.
• “Publish” is halftime. Creating the asset is only the first half of the job. Distribution is what gives the work a chance to produce a return.
• Fear is a distribution problem. Freelancers often say they lack time to promote themselves when the deeper issue is fear of judgment, repetition, or being seen trying.
• Distribution is a competitive advantage. Great work alone doesn’t guarantee reach. The freelancer who consistently gets strong ideas in front of the right people can outperform someone with equal—or even greater—technical skill.
• Show people how good you are. Long-form content, case studies, videos, podcasts, and thoughtful analysis can demonstrate how you think before a prospect ever talks to you.
• Video and niche communities deserve attention. Ross sees video as a powerful relationship-building format and encourages freelancers to engage genuinely in communities like Reddit rather than treating them as another billboard.
• AI accelerates expertise. It doesn’t replace it. Good judgment, taste, fundamentals, and subject-matter knowledge become more valuable when powerful tools make execution easier.
• Public speaking creates authority at scale. Ross went from being nicknamed “Shy Ross” to using speaking as a way to build rapport, credibility, relationships, and business opportunities.
• Getting better is bigger than business. Ross closes with a reminder that growth isn’t only about becoming a better marketer. It’s about improving how you serve clients, teams, family, and the people around you.

Notable Quotes

“If I give value to the internet, the internet will give me value back.”

“Instead of viewing the job as done at that moment, I’m going to view it as halftime.”

“Show the world how good you are… Give away all the sauce and then get it in front of the right people.”

“If you give a good marketer AI, you’ll get good marketing faster. If you give a great marketer AI, you’ll get great marketing faster. If you give an exceptional one percenter AI, you’ll get exceptional one percent level marketing faster. AI makes everything faster.”

Resources Mentioned

• Follow Ross Simmonds on LinkedIn: https://www.linkedin.com/in/rosssimmonds/
• Check out his website: https://rosssimmonds.com/
• Check out Foundation: https://foundationinc.co/
• Check out Distribution: https://www.distribution.ai/
• Listen to The Ross Simmonds Show: https://podcasts.apple.com/ph/podcast/the-ross-simmonds-show/id1653650073
• Check out the Freelance Cake Community (for established freelancers eager for sustainable growth): https://www.freelancecake.com/community

Watch This Episode

Transcript

00:01
Hey there, welcome to the Freelance Cake Podcast. I'm your host, Austin L. Church, founder of the Freelance Cake community. The goal of this show is to help full-time committed freelancers get better leverage. As the sworn enemy of busyness and burnout, I have no desire whatsoever to see you work harder. So I reveal the specific beliefs, principles, and practices  you can use right away to make the freelance game more profitable and satisfying. So chill out, listen in, because the best is yet to come.

00:40
Welcome to another episode of the Freelance Cake Podcast. Most freelancers spend years trying to reach a certain level of success, but what happens when you get there? What happens when you've built a thriving business, achieved some financial freedom, and then realize there's still another chapter waiting for you. My guest today is Ross Simmonds. Ross is the founder of Foundation,  a content marketing agency that works with some of the biggest B2B brands in the world and the CEO of Distribution.ai. Before building those companies, Ross grew a multiple six-figure freelance business from a small town in Nova Scotia, proving that geography doesn't have to define ambition.

01:26
In this conversation, we talk about reinvention—how Ross went from freelancer to agency founder to software CEO, and why he sees growth not as a series of career moves, but as the result of years of compounding effort, curiosity,  and experimentation. Ross and I also deep dived into content distribution, which Ross argues is one of the last true competitive advantages. He explains why most content never reaches its potential, why fear keeps so many talented freelancers from promoting their work, and how strategic visibility can create opportunities far beyond what great work alone can accomplish.

02:13
We discuss public speaking, personal brand building, AI, and why the freelancers who thrive in the years ahead won't be necessarily the ones with the best tools, but will be the ones who continue sharpening their expertise and sharing it with the world. If you've been wondering what your next chapter could look like or whether you've outgrown the limits you've placed on yourself, you're going to get a lot from this episode. All right. Sit back and enjoy my conversation with Ross Simmonds.

02:53
Ross, I'm very thankful that you replied to a message and an email from a total stranger slash bozo, this guy, and agreed to speak in part because, and I told you this right before we started recording, one of my community members reached out to say how excited she was to know that you're speaking in part because she read your book. Your thinking on content distribution totally changed her approach to her client work. You have an incredible story coming from a rather small town in Canada. Now you're the CEO of an AI powered startup. There is so much here I want to unpack, but before we do, just give folks who don't know you maybe two minutes, the life of Ross in two minutes.

03:52
Let's do it. Thanks for having me first and foremost, really appreciate it. I am a Canadian born and raised in this small little community called Preston, Nova Scotia, population of about 3,000. Most people would know by its connection to Halifax, which is also a small place in Nova Scotia, which is also a small place, but either way, from a small place. All that said, from a young age, I've been obsessed with entrepreneurship. I sold do-rags out of my locker when I was about 14 years old. That was my first business. Yeah, I fell in love with capitalism way back then. And I was like, great, I can buy poutine for all of my friends because I'm selling do-rags. And I was super excited by that. That was my first biz.

04:32
Then I fell in love with the internet. I started to sell a pair of jeans that I had bought on a school trip on this website called eBay and then my mind was blown that somebody in Atlanta would buy a pair of jeans from someone in Nova Scotia. So then I continued to go down this internet path. I started a website where I was writing about fantasy sports. Me and my sister started a video game website dedicated to a game called The Sims. At that point, we started to reach thousands of people every week and I was like, whoa, this internet thing is crazy.

05:03
And I started to go aggressively at my football blog. So I started to about fantasy football. I was getting picked up by some of the big publications. They were quoting me and I couldn't believe it. I was living in my parents basement.  At this point I had just started university and I was like, huh, I'm like making money off of this thing. I was studying marketing while in university, but my marks started to drop. My mom brought me into the living room and had a tough conversation about how my marks were gonna drop and I needed to shift my focus to business and marketing.

05:33
So I started a blog called RossSimmonds.com. Started to write about marketing. A company called Bacardi reached out to me in this little province called Nova Scotia and they were like, can we fly you down to Miami to teach our C-suite on how to do marketing to Gen Y? At that time, Gen Y was young and hip and cool. So they brought me down. I did a session with them. The light bulbs went off that if I keep creating content on the internet, then I might be able to reach more brands like Bacardi.

05:58
I get flown to Miami.

06:00
I'm flying to Miami, get out of the Canadian winters. And I was like, cool, this is a fun life. So I just started to write, write, write, write, created more and more content, more and more brands started to reach out and want work. I started to do that work, spun up a company called Foundation at the time, as well as a bunch of other companies. I've started cleaning companies, I've started coffee companies, I've started more fantasy websites, I started a vegan plant-based website, I started a barbecue website. I do all kinds of different things. And then I had a child. And my work into the late evenings of 3 a.m. were no longer feasible. So I started to hire and build a team. And then that team continued to grow, continued to grow and build software companies, invest in software companies, continue to write about content, create YouTube videos about content, bigger brands, bigger team, continued to grow, continued to compound. Today we are a 50 plus person marketing firm that works with some of the biggest B2B brands in the world. I've written a book. I partner with brands like Reddit and LinkedIn and HubSpot on content all the time. I run a company called Distribution.ai. I'm an angel investor in a ton of different startups, some successes, some failures, but that's a part of the game. And I am a dad of three and entrepreneur, lover of business and super excited to be here with you. It's gonna be fun.

07:21
I mean, that was way longer than two minutes though. Oh, it was worth it though. That was worth it. I'm like, could he do that again? I'm like, probably so. My entrepreneurial start was not do-rags, but origami.

07:38
Nice. I love that.

07:41
And there was so many parallels in your story, but rather than like hard relate to everything you just talked about, I do want to get into some of the questions that I spent some time thinking through because we have this audience of more advanced freelancers. A lot of them are creating content for lead gen. A lot of them are creating content for clients. Yeah. But let me back up. You were a solo freelancer for a while there. You kind of accomplished or grabbed ahold of the Holy grail, right? Which was multiple six figures. That's before you even turned 30. You're from this small town. You don't have an elite network. You don't have the convenience that you would have in a big city of being able to just drive to opportunities. So a lot of folks would have just, I don't know, made excuses or kind of stayed exactly where they were. But you decided at some point that the ceiling you saw was a choice rather than a true limit.
How would you respond to all that? Because there's every reason that you should not have accomplished a lot of what you have given tiny town in Canada, right?

09:11
For sure. think coming from a small town, having no connections in marketing, having no idea who or what someone would look like that was intact, like technology in that world is not something that I grew up around. My parents were like in healthcare and childcare. My grandparents were in paving or staying at home. Like this was not a world that I grew up knowing things about. But I was a geek and I obsessed deeply over the internet. And I think it was through that… the biggest privilege that I think I actually had was parents who supported my geekiness and encouraged me to stay geeky and embraced the nerdiness of this internet thing. So they allowed me to kind of just pursue it. They didn't know what I was doing. They still probably don't know what I'm doing. I would say with a high level of confidence, they have no clue what in the world that I do. But that was my only advantage. And I could have gave up.

10:16
But I had a chip on my shoulder truly where I kind of just wanted to prove to myself and others that like, no, it doesn't actually matter. We live in a digital world where you can reach anyone with this internet thing. You can send an email to anyone and magical things can happen. When I was in university, I tested this hypothesis. I came across, I don't know if anyone's going to be familiar with this old ad, I'm aging myself. But originally when I came into marketing, I was obsessed with the movie in the show, sorry, Mad Men. So I love the philosophy of traditional advertising, not digital, just good old fashioned traditional. And there was a jingle about Band-Aid and Band-Aid's brands got stuck on me. Like that jingle just like was to me creative excellence. So I found the creative director of that company and I reached out. And to me that was like me meeting Magic, like Michael Jordan of advertising. Like this guy created a commercial for Band-Aids and he wrote me back. And I was like at that moment I realized like you can reach anyone. It doesn't matter where you're at. It doesn't matter what you look like. You're just got to if you have an email, you have coffee and Wi-Fi, you can reach anyone. So why can't you get an e-transfer from someone too? Like why can't you get a wire sent to your bank account? You probably can if you add enough value. So I just like locked in and believed that I could. And then over the years just decided that I would live by a simple hypothesis, which was, I give the value, the internet value, the internet will give me value back. That has truly been ingrained as a principle in my mind for the last 20 years. And it's a hypothesis that at the time I didn't know if it was true, but I believed to be true. If I give value to the internet, the internet will give value to me back. And it's worked. It really did.

12:12
Wow. You made me think of this one really small interaction I had with my grandmother and it's going to make her sound terrible, but stick with me. I broke my leg in eighth grade playing football and she overheard me whining to myself and I was like limping around in my crutches and I said, why me? And she turned at me, like turned to me and she said, well, why not you? What's funny and I can't say that I was like all that mature at the time. So maybe this was out of character, but I actually internalized it. And I thought, well, if it's true of negative things, it could be true of positive things too. So I hear that in you. Some of that, it sounds like, you know, it nurtured in you by your parents. Some of it was like reinforced when you had the courage to just reach out to someone you admired. So do you see that mind, that why not me mindset sort of coming up around some other critical things that have happened across your career?

13:20
I think for me, I've had that, but the biggest piece, which is not something that I've probably admitted much to other folks inside of my own immediate family is that I am very much a, I don't want to call myself petty, but if someone tells me I can't do something, it fires me up to show them that I can. And I have had a folder on my desktop for the past like 15 years of rejection letters, of jobs that when I was just getting out of school and I was applying people who said no, I have screenshots of emails where people say no, this will not work. I have comments on Facebook that I've screenshotted where people say you're silly. You're an idiot. This is dumb. The comments on Twitter, all of that stuff. I have a little folder, dedicated to that. So whenever I feel like I'm doing too well, I can go into that and I can just get fired up to say, okay, let me show these folks like what I'm good at. Is that healthy? Probably not. I don't think I should encourage people to do that. I don't think it's the right thing, but it's what I like to do. And it fires me up. It's just like a nice little fuel that lets me do things at a high level all the time.

14:33
What's the name of the folder?

14:35
Ha ha. It's called the petty folder.

14:38
It really is called the petty folder. That is amazing. That is… And here's the funny thing about the way interviews go. That's going to be the thing that people take away from this. They're like, I can't just have a folder of like nice things that people have said. I need a petty folder too. But back to the real questions. So you went from freelancer to agency founder to software CEO. You don't think of this as like a linear career path. You think of things that have happened in your career more as compounding over time. What do you mean by that? And why does that compounding framing matter for someone who's five or 10 years into freelancing and wondering what's next for them?

15:29
Yeah. Einstein said that compound interest is deservedly the ninth wonder of the world. And I believe that when you think of your career, the more that you think of it in a viewpoint of compounding, scratch that, I say career. I think it's a life thing. I think you have to view your life in a perspective around everything that you do with intention compounds. And if you don't do things with intention, those will also compound in instances and moments of exercises, of choice will get you to somewhere, whether it's where you want to be or not is connected directly to the activities that you take. So for me, the freelance path was always with a desired outcome, which was from a very young age, having as much control over my life as possible. I have always wanted to have control over my own life. So the initial desire to go into freelance capacity and to be a freelancer, was I wanted to be able to start my job, start my work and go to bed whenever I wanted and do whatever I want in between. And it compounded through a persistent commitment to doing things that I enjoyed. And I enjoy problem solving. I enjoy creation. I enjoy tinkering, building. I view the world of business in many ways as a game that we're all playing. And I view it in that, I forget who wrote the book. think it's Simon Sinek, the like infinite game, like that concept also holds true to me where if I can just constantly be in a state of joy because I enjoy the work and it's not really viewed as work to me, I'm happy. And the compounding elements of it is rooted in that vision of how can I have complete control of my life? How can I add value to the internet or the world at large? And how can I assure that at the end of the day, when I do take my last breath, I can look back and say, man, I played a fun game. I had a lot of fun playing it. I impacted people positively. Hopefully I left the world with more value than I extracted while I was here. If I can do those things, like I'm good. I'm good with the time I have here.

17:45
Values. That's what I heard. Enjoyment. Playing an infinite game, and not separating career from the rest of life, which is kind of an artificial separation anyway. Let's shift gears just a little bit and talk about content. You said something and you've been saying it for years. That's interesting. Most content collects dust. I think people will hear that and they will nod along and they're like, well, yeah, that must be true. But why does no one act as though this is true? We just keep on pumping out more content.

18:35
Yeah. think the reason why most content actually collects dust is because of a deeply human reason. I think everybody's afraid. I think most people are not like, they're not doing it intentionally, not allowing it. They're making excuses and saying they're too busy, but in reality, they're just afraid. They're afraid to get unfollowed. They're afraid to have real judgment and feedback of their work. They're afraid that somebody might unfollow them and they're afraid that someone is going to talk about them behind their back about them being a try hard or something like that. It's all fear. I think everyone comes up with excuses like, I'm too busy. I've got so much on the go. I just wish I had more time to promote my content. You have the time, especially in today's day and age when you have tools and technology to allow you to accelerate this stuff and to schedule it and promote it. Like I built a platform, Distribution.ai, where you can schedule content for months in advance, right? But the real reason is because people are afraid. They're afraid that a post goes live on X or LinkedIn or Threads or blue sky or Mastodon or Reddit, whatever. And someone says, I think you're silly here. I don't think this makes sense. Then all of the emotions come out. Or they're afraid that they're going to put out a post on LinkedIn and then their friends or their colleagues or their boss is going to say, why'd you put up that post? Feelings. That's the real reason why content collects dust. Everyone pretends that it's because they don't have time, but it's actually because everyone is afraid.

20:18
And they need a petty folder.

20:21
Yes. Exactly. People do need something to mode... I do think though, like it's a good insight, Austin, like internalize for yourself. What is stopping you from actually getting where you want to be? Are you not there because you're afraid, you don't want to be judged? You're you don't want to look a certain way in front of your boss, your manager, et cetera. Like, that really… And then ask yourself, are you okay never getting there? Because then, cool, that's your decision. But if you actually deeply, truly do want to get there, then you do have to shift your behavior. And for me, I can use that petty folder to be like, okay, right. I still have to prove this to these folks, even though it's toxic, I know I get it. But like, I can still use that as some fuel. So for me, I think that's what I would encourage your listeners to do because a lot of freelancers when they're even at the like, let's say you're at a 100K if you're not at a 100K you have zero excuse to not be promoting your content. Let's put that out there. If you're not at a 100K it makes absolutely no sense to me why you're afraid. You have to get to at least six figures in today's economy. So please go promote your work. After that though, then you have to ask yourself about the different levels. Okay. Like, can you get to 250? Can you get to 300? Can you get to 400? Where do you believe is the number that's going to make you satisfied and happy? And if you are actually content and you're pretending that you're not, then you're content. But if you actually truly want to get higher, the only way to do that is to increase the sample size of the people that you reach. So promote your content. Oh, you just press publish on a blog post, a YouTube video, a podcast. What have you done with it? Are you promoting it? Are you amplifying it? You should be promoting it every other day. And then people will say, well, Ross, what if the person who sees it, people are going to unfollow me because they've seen it so many times. No one cares. Everyone is busy. Everyone is busy. No one actually cares. If you share a post on Tuesday and then you reshare it two weeks ago, they probably weren't online. They were probably changing a diaper. Like no one cares. They're busy. Got other tabs opened. But we're all in our heads. So we just need to like separate that anxiety of what people think and just promote, amplify, distribute your work, and keep going. And if you do it for like literally six months, it'll change your life. Absolutely will change your life.

22:53
Yeah. I think you're so right about fear. I remember when I finally got serious about posting on LinkedIn and I finally attracted my first bonafide troll, and he just got all up in the landscaping in my front yard like this is my front yard What are you doing in my front yard? And he didn't care about me and he wasn't taking the idea seriously. He was just trying to draw attention to himself, and you know what Ross? I lived, it didn't kill me. And eventually he just faded away. Like he lost interest. I don't think I was an easy target at the end of the day. I compared notes with a couple of friends. What do you do? And one of them said, Oh, I just block people immediately. And I'm like, but wait, what about like the fair exchange of ideas or like free speech or all that? He's like my front yard, I don't have to let people crap in my front yard. And so I just think you're so right about the fear, and about needing to like ask yourself what is on the other side of it? Is it realistic to get to 250K or 300K or 400K if I stay the same? And when you like put it in that framing. But another thing that you said in your book, and this is pretty pivotal in the book, you based the whole thing on this counterintuitive ratio: spend 20% of your time creating, 80% distributing, most freelancers, and I will lump myself into this group, live this exactly backwards. What is the psychological reason for spending 80% of your time distributing and, or sorry, 80 % of your time creating, and what does someone have to do to flip it so that they're spending 80% of their time distributing?

25:02
Creating provides a immediate dopamine rush. When you press publish on a piece of content, it feels great. You feel so good. You feel proud. You just spent time and energy, exertion, ideas, thoughts, some pain, some struggles, some curiosity, some rabbit holes, some late nights, some procrastination, some coffee. You had to go through the hero's journey to get to a complete objective of pressing publish. And then you're done. The world is yours. You can pop the bubbly, you can celebrate, you feel good. However, there's no results. There's no results when you have published. You get the results after people consume the thing that you've created and they decide that it was worthwhile for them to reach out, that they decide it's worth linking to, that it's worth reaching out to you, it's worth hitting that share button, repost, reshare, email, share in Slack, all of those things. But we already had our dopamine rush because we had published. So what do we want as humans? We want that again. So we go straight back to our computers, we plug in our headphones and we're going through the hero's journey and we have publish again and we get that dopamine rush and we hit it. We have publish, we pop the bubbly, the cycle continues over and over and over again.

26:17
And we're talking in general terms and not about me. Correct?

26:23
Right! Exactly. And then we cross our fingers and hope that maybe that piece that we created was so good that someone will pick it up. That maybe someday someone will read or watch or listen to the thing that we created and it's going to go viral. That someone's going to share it. Someone's going to sign up for our podcasts. Someone's going to subscribe. Someone's going to become a member of your thing, whatever it might be. But when it comes to distribution, you have a whole different game. The game is not just, let's just press publish and go through the turmoil of amplification because it's short. To promote a post, it takes less than a minute, maybe two, maybe three, right? It doesn't take a lot of time. So the reward and the feeling of execution isn't as much because if you're doing it right, you're also scheduling the content into the future, which is thinking about the future. And nobody ever thinks about the future of them. They only think about the short term. So you have to schedule things for the future version of you. You have to like make sure that that stuff's amplified in the future. And for humans, that's tough because you don't get that constant stream of dopamine that you used to. But if you can make a mental switch where you say, I'm going to feel the greatness of creation, but instead of viewing the job as done at that moment, I'm going to view it as halftime.

27:46
And now I'm going to spend the same amount of time, just spend the same amount of time as a starting point that you did creating, promoting it. So what does that look like? It means let's pretend that you created a podcast series and you're interviewing a specific type of niche. Let's pretend for ease of use, you're a freelancer and you're interviewing people in the healthcare space. So what I'm going to do, I'm going to feel good after pressing publish on a great interview with someone. It goes up on Spotify, it goes up on Apple. All those things are great. I'm now going to write a blog post that talks about the interview. I'm going to embed the video with it directly at the top. I'm going to share that blog post on LinkedIn. I'm going to share it on X. I'm going to share it on Facebook. And then eventually I'm going to find a Facebook group with my ICP, my ideal customers, where they're spending time. I'm going to join that group and I'm going to share the link in there too. Now for most freelancers, they're probably saying, cool, that's a lot. I'm done. I'm not done.

28:44
Then you're going to share it on your Instagram story. You're going to also probably ask yourself, can I turn this same blog post into an article on my LinkedIn? Then you're going to use the scheduling tool to make sure that you're active on different channels all the time promoting that same piece. You're going to take the podcast, identify the money moments, which are the key moments where the interviewer asked the interviewee a key thing that you can cut up and chop up and then turn them into social clips. You're not going to release them to the world all at once. You're going to take them and you're going to trick them out on Instagram reels, share them on TikTok, share them on LinkedIn. You're going to again, schedule this out so you can go and hang out with your family, hang out with your friends, do more podcast creation, but you're going to have all of these video assets going out there with links to the blog posts that you created or to the podcast. You're going to write an email that goes into your email list promoting it. And you do that, eventually the amount of time and energy that went into the promotion will match the amount of time that went into the creation. And that creation will finally pay the amount of ROI that it required to actually do it. Because for some of us, we'll spend 50 hours working on a piece. And if we take our hourly rate and we multiply it by 50, that's the cost of the asset that you produced. And then we don't do anything to promote it. Whoa, what a waste. That's wild. So that's the way that I would think about it.

30:08
I love the halftime analogy. Made me think of Nir Eyal. I think he wrote Indistractable. He wrote a couple of other books too. I'm blanking. He just had one that came out. I think it's called Beyond Belief. Well, he had this… I listened to an interview with him recently and it applies here to this halftime idea. He would get stuck while writing books and it was just so difficult. It was maybe kind of boring. And he put a post next to his computer that says, this is what getting better feels like. And so I think that's what you're describing. We're tempted to just chase the next dopamine hit or to even like put our feet up, pop the bubbly, like you said, and celebrate. But that's exactly when the distribution engine should kick on. And even if it's… I don't know, less enjoyable in the moment…

31:14
And it is going to be less enjoyable for many because it's like you have to approach that fear of being touched.

31:22
Yes. It's not even neutral. It's pressing proactively into fear. And yet I know you're right. I know you're right, Ross, because when I think about the creators and the folks whose content is just amazing, I look at it and I think, wow, that took a lot of effort. And then I think, and I've actually seen that before from them. Like they play their greatest hits. So I know the people I admire most who are getting the results I want are actually doing what you talked about. They're doing what you talked about. And I don't like it, Ross. I don't like it. So most people think that distribution just means posting on social media. You've already walked us through what distribution means really. But what does it mean at the level where you now operate as like the CEO of Distribution.ai and the leader of this 50 person team?

32:30
Yeah. So Distribution is not exclusively around how can I take this one blog post and spread it? Like Distribution to me represents in many ways, one of the few competitive advantages left in marketing and business. When you look at the ability to now build apps with coding tools like Lovable, ReplIt, Codex, et cetera, like it's never been easier to build your own app. It has always been difficult to build a great distribution engine. There are great creators right now. There's probably some great freelancers right now listening to this that are better than 90% of the people in their competitive market, but they don't get even 10% of what the most distributed creator and freelancer in their space actually generates in terms of revenue. It's not because their work's not good. It's not because the other freelancer is some massive genius when it comes to the work. It's because they have better distribution. Distribution is the ability to reach the masses at scale where your sample size, your target audience is spending time, right? Airbnb versus VRBO. Airbnb had the first distribution through Craigslist where they reached out to people via Craigslist to actually get them to do short term rentals. Brilliant distribution. Microsoft installs MS-DOS on all of the IBM computers through a licensing agreement not realizing or at least IBM didn't realize they were giving distribution of that software to the people who grew up on Excel. Newspaper companies had the best distribution strategy in North American history. Every single door had newspapers dropped off at their doorstep. People, young boys and girls would run around dropping the newspaper off at doorsteps at every single home. Then the distribution channel gets disrupted. We get these little things called mobile phones. So you no longer get access to my door. So where does your revenue go? It evaporates because no one's willing to pay if I can't get the distribution access. But what rises? Advertising on mobile phones because they have distribution to the people that the newspapers once had that they no longer have. So when anything can be created, the final opportunity that is existing for businesses and owners is distribution. That's why influencers are making millions of dollars in creating billion dollar companies on the back of a YouTube channel that they created, that connected with folks. And now they have Netflix deals. Distribution is the ability to guarantee reach through creation consistently, building trust, community, rapport, and understanding the nuances of the last thing that we all want, which is connection. So if you can recognize that humans will forever want connection and you can find a way to distribute your stories because of it, that's how you win. So long answer to a short question. So let me wrap it in a bow really quick. What is distribution? Distribution is the ability to take a story, an idea, a brand, a business, and get it consistently in front of the customer and the person that you want to reach who will then turn that impact into a transaction for your business.

36:12
What are the most underused distribution opportunities right now that almost nobody is exploiting? And I'm thinking about those more advanced freelancers and consultants who feel like they are their niche or markets best kept secret.

36:32
Yeah, great question. In this market today, right now, and it seems like it's overkill and that everybody has been saying it, but the truth is no one has done it. Video content is the most under priced approach to build relationships today. Video content is mispriced massively. If you can create video content and reach your audience through YouTube, through Shorts, through reels, through clips, the opportunity today to do that is amazing. For two key reasons.  One, the platforms are incentivized to show videos because what do we as consumers want? We want video content. There's a reason why people watch movies and TV more than they read books. I built my entire career on the back of the written word. But I have come to grips with the fact that not a lot of people like to read. They'd watch a video. They'd rather listen to a podcast. People would rather passive consumption than active consumption. So if you can create video content today that serves your audience, serves your customers, I think podcast is also a high value one. If you can incorporate video into it as well, chef's kiss, that's the best. But video content is absolute gold today. Then the second thing is the platforms are incentivized to distribute videos because they get ad dollars. But also remember what we talked around connection. Humans are more likely to connect with a human than anything else. And you know what you can't really fake yet. AI videos. It's close. It is very close, but it is difficult. It's kind of the one thing that I think there's going to be an increased demand for is video content because people wanna stay connected to people. So video would be the number one on my list. And then I think there's a lot of niche channels, like going into community specifically, I think is underestimated. If you can go into a Facebook group, if you can go into a Slack group, if you can find a niche forum, those spaces are also… Subreddits. All of those places I think are massively valuable too.

38:45
Yeah. You talk about Reddit a lot and I saw this crazy stat that Reddit now commands 40 to 45% of top three search rankings across a lot of B2B SaaS verticals, which is wild. So what's actually happening there and is there anything that you think freelancers, content strategists, marketers, even those of us who might see like a subreddit and think that's where all of my would be clients are hanging out. Like how should we be thinking about Reddit?

39:24
Yeah. Reddit. I wrote my first like digital book on Reddit back in like 2016 and I got yelled at by a lot of folks on Reddit way back then for breaking the code to how to do marketing on Reddit. But the same philosophies then work today and it's pretty straightforward. You find your audience and the customers that you want to serve. You're going to then become committed and obsessed with studying the types of content that they want. One of my favorite things to do is to sort the content by top posts and then analyze the top posts in a subreddit. Look for trends. What are the formats? What are the styles? What are the topics that they care about? Then you're going to ask yourself, can we create it, but make it better? Can we create better content than what has existed in the past in these communities? And ideally, you're going to find something that's like five years old, something that five years ago resonated with the community so deeply that everyone loved it. They said thank you in the comments. And then you're going to find a way to recreate that for the modern era. And then you give that to that community and watch how they respond. They will likely respond very positively. For freelancers, the best thing that I could advise you to do when it comes to Reddit is to not show up like a marketer, but instead show up as a Redditor first. Meaning have some fun, don't take your brand too seriously, ask questions, engage authentically, and ask yourself the same question that I mentioned earlier in this interview, which was, how can you add more value to Reddit than you take from it? Go in with that pure intention of educating people, engaging them, entertaining them, or empowering them, and you'll win.

41:03
So good. I think that's true of a lot of marketing. Are you having fun with it? Are you giving generously and don't be surprised if that comes back to you versus just pitching or promoting in a way that is not valuable to other people. So we've talked a little bit about distribution. We've talked about content. We'd be remiss to not talk about AI.  You have heard as much as I have that AI is coming for my job. AI is going to replace you. And you have actually been pretty vocal about saying the opposite. So what is your version of the AI narrative and what do you think most people are getting wrong in that AI conversation right now?

42:03
I think if you give a good marketer AI, you'll get good marketing faster. If you give a great marketer AI, you'll get great marketing faster. If you give an exceptional one percenter AI, you'll get exceptional one percent level marketing faster. AI makes everything faster. However, if you're a bad marketer and you get AI, you probably are going to get worse. It's probably going to be a little bit worse than that because you have no taste. Like I think it comes down to the person who is using the tool is more important than a lot of other technologies that we've used. If you gave me AI and you said, use this AI to do open heart surgery, and then you gave AI to an actual surgeon and said, do open heart surgery, raise your hand if you want Ross to do that open heart surgery, you better not raise your hand. Not a chance, right?  Like no one would do that. If you put experts, true experts behind these tools, the things you can do is amazing. So my advice to folks is double down on learning your craft and becoming exceptional and allow AI to facilitate your growth, your professional development, but you still need to learn the fundamentals. I spoke at a high school a few weeks ago and they were like, Ross, you're talking so much about AI. Like, can you tell the teachers that we don't need to do our homework ourselves, and again, the future world just use AI. It's like, you need to understand the fundamentals of why five times five equals this. If you don't know those reasons, you can't check the hallucinations. A lot of marketers who are early in their career, I hope that we're creating cultures where those people can actually still learn the nuances of what they have to check because if you just allow the AI to guide the show, the hallucinations will kill you. I have seen so many people open up a ChatGPT, open up a Claude, open up a Perplexity and they're like, Hey Claude, what should be my YouTube strategy? Without providing any data, the tool has no data associated with their subscription count, with what type of titles they're in, no competitive analysis. It doesn't understand the hooks that you're using. How in the world can you give a reco if you can't consume that content and don't have the data. So my advice to folks is as marketers learn your craft, understand your craft, that will make you still stand out and let AI be your augmentation tool to go faster at doing the things that are repetitive in nature.

44:54
What does Distribution.ai actually do?

44:59
Great question. So every day creators are pressing publish on YouTube videos, on podcasts, on blog posts, and then they get afraid and they don't promote them. So I said, you know what, let's give them no excuse. Let's create a tool that learns their voice,  learns their tone, and then with a click allows to connect to their YouTube feed, their blog feed, their podcast feed and will write the LinkedIn posts for them, will write the X posts for them, will write the posts for Mastodon, for Bluesky, for Threads, all in the formats that are preferred for those channels and help them put it on autopilot. So two days later, four days later, two months later, six months later, they are constantly on promoting the content that they produced. So that's what distribution.ai does. It is a constantly always on platform that connects to your evergreen assets, the content you're producing, and then it will coordinate and schedule that content to be amplified. For businesses, it has a secondary model where the organization can connect it to their things. And then the team can be amplifying the content for the brand. So this whole sales team can be on brand promoting and amplifying the blog posts as they go live, the YouTube videos as they go live, the podcasts as they go live, leveraging sales enablement and things like that, connects into HubSpot, writes the email that can go into your HubSpot and distribute the blog content or the YouTube content or video content, whatever you've created. And also we'll write a blog post from any videos that you create. So again, I talked about earlier around how if I create a YouTube video, I would embed that in a blog post distribution.ai will write the blog post for you. And it's all built on the back of the 15 years that Foundation has done this exact type of work for our clients. We used to listen to clients’ YouTube videos, find the money moments, chop them up, turn them into clips. We would write blog posts about them. We would do all of that. And distribution.ai essentially is the alternative where it can be done through software.

47:04
So is it a given that somebody would start with a long form piece of content?

47:11
Yes. Yeah. Okay. It starts with long form content or you can upload thought, an idea and it can turn that into a longer form piece of content. So we have a functionality where some folks will upload like a case study from a PDF and then that study becomes a new asset and gets transformed into LinkedIn posts. There wouldn't be a link with it, but we'll turn it into a social post that sounds great and talks about it.

47:37
What I like about that is that the model assumes there's already some taste that has sort of seeped into an idea or a long form piece of content or stories or I've started thinking in terms of dirty fingerprints like my humanity, my imperfections, my weird turns of phrase, the fact that I sometimes slip and say y'all because I live in Tennessee. I think that's actually a good segue to the next question I had for you. You've said that AI won't kill the expert, but it will kill the average. And so even something like distribution.ai. Yeah. If there's no real point of view there, there's no real expertise. It's not like distribution.ai is going to magically create great content, but sounds like distribution.ai and also other AI tools will certainly make certain freelancers and consultants more powerful. Let me change the question a little bit. What do freelancers and consultants need to do so that they're less likely to be replaced by AI?

49:06
It's so basic, Austin. It's going to sound so basic. Do good work. I know it's like the most basic answer in the world, but like if you do good work, you can't be replaced. There will always be a demand for people who do good work. And if you do it on time, even more brownie points for you. Most people don't do what they say they're going to do. Most people do not do what they say they will do. They'll tell a client, I'll get that to you Friday. And then they don't. The bar is not high. The bar is not that high in business. I wish it was higher, but I've seen a lot of things and a lot of freelancers are holding themselves back from their own dreams because the like imposter syndrome, the lack of confidence, the thought that they're not as good as like you're probably better than some of the big firms that make millions of dollars every month. And it's like you can compete with them. You just have to do good work and take your work seriously. If you take your work seriously and you are committed to your craft, you win. You really do. But here's the tricky part. You can do that great work, but if you don't have the opportunity to do the great work, then you're never going to win because you're stuck. So let me flip this a bit because as much as I wish just doing the good work would be enough, it's kind of not because you have to do good work with the right businesses and the right orgs. So if you stay with the like $1,000 projects, $2,000 projects, and that's like all you're touching, you're really going to have a hard time getting up to the 10, the 20, the 30, the 50, the $60,000 projects. So how do you get through that? You have to get through that by saying, okay, how can I position myself with high value clients to do good work and then get capture some of those budgets and capture those? You do that by being intentional with creating clear examples and stories around how good you are. So the evergreen style, you create long form content, talking about your work. You create long form content, talking about how you think, showing how you think, whether it's video, podcasts, blog posts, et cetera. You show people how strategic you can think, but you make sure that that then gets distributed to the people in the orgs that you want to reach. So for me, when I was a young pup, just getting started in the industry, I wrote a blog post about how to do marketing to Gen Y. And that's how Bacardi found me. Then I wrote another piece. It was, these are the 20 best practices for software onboarding. I had no experience in software. I just signed up for a bunch of software companies, websites…

52:05
But you had some taste and you're like, that sucked and that was much better.

52:10
And I described it in detail and then I had like four SaaS companies reach out to me and say, Hey, do you do marketing? Do you create content for SaaS companies? I was like, no, but I can.

52:20
I do now.

52:22
I do now. I do now. And then over time it just compounds. So my answer to the question is like, what can marketers, freelancers do? Show how good you are and then be relentless at distributing the stores. Show the world how good you are and be vulnerable in showing how good you are. Give away all the sauce and then get it in front of the right people.

52:47
And it strikes me that distribution comes back into the conversation here because if you're always creating the next net new piece of content, it's like you never get your head above water. You can never get ahead. Kendall Cherry is a friend of mine. She's also one of the speakers at Advanced Freelancer Summit and she recycles a crap ton of content. What that enabled her to do though was spend a lot more time on case studies. So because she is recycling old content with an emphasis on her greatest hits, that means the little bit of time she has to work on new content, it's the type of content that could actually get her a client. It's those types of posts that you were talking about because it's not like you wrote either of those posts in 30 minutes. Like those were deep and involved and took time. So I think a lot of freelancers and consultants actually get caught in this negative flywheel where they can't go study Reddit. They can't write the next banger. They can't write the highly strategic case study. They even maybe don't have time for like distribution, maybe sending that case study to 20 highly targeted SaaS companies being like, Hey, I wrote this post about great onboard anyway. I'm talking too much because you got you got me excited Ross, you got me excited. I have several more questions before we end, maybe we'll do them a little bit more rapid fire. I don't want to miss out on these ideas. I mean, I think we could talk for five hours, but I can't afford you to pay you what you're worth for five hours. So you've talked a lot about how public speaking has been a really important, maybe even the single best investment you've ever made. What's the argument there?

55:12
Yeah.  You own a room when you can come across as the expert. So for me, when I go and speak at an event, my nickname in junior high was Shy Ross. I wasn't a extrovert by nature. I read a blog post that told me if you want to do well in marketing, you have to learn how to do public speaking. And I was like, oh, okay, let's figure this out. So I signed up to speak at a local event. got on stage, I sweated through my shirt. It was a lesson, it was a white shirt, horrible decision. Everyone could see everything, but I didn't stop signing up. I kept signing up and what happens in a speaking engagement, if you are good and you are successful on stage, is it makes networking for the introvert inside of me to be me. Because I go on stage, I do my thing, and then I have friends. Everyone in the event is officially my friend if I delivered value on stage. So I don't need to wait in a corner and like hope that someone will come up to me. Because I'm public speaking, the whole room knows me. And then afterwards, I start to continue to get emails and messages from people. My first publicly traded company that ever worked with Foundation…. this was after the early stages of like small engagements, but the first, I'd say first 250 grand business account that we closed came out of a speaking engagement where I went on stage, I added as much value. They sent me a message and that was the deal. So, public speaking is game changing.

56:38
Authority. Rapport. It's there's that halo effect. And I have to think that your book or books may have created that same effect. It's really hard to say that someone isn't an authority if they are on a stage in a room full of people. Okay, last question… You've said the only thing a freelancer should be worried about is whether they're better today than they were yesterday. Not as a marketer, but as a person. That is a much bigger frame than we typically see on LinkedIn, where I spend a lot of my time. Not very many people are talking about integrity or character or becoming a better person. They're talking about writing better hooks. What do you actually mean by that? And why do you think like becoming a better version of yourself belongs in any conversation where freelancers and consultants are thinking about what's next and how to reinvent themselves?

57:50
I believe we go through this life once and at the end of the day, we're all going to end on a bed, maybe hopefully taking a last breath, hoping and wishing that the journey that we had was great. And if you can't constantly be pushing yourself to maximize your time here and add value and be good and do good….  Like I have a hard time thinking through how you will be successful as a freelancer because you have to be willing to serve your customers, your clients,  your team, hopefully those in your family, your circle. And if you do that, you just get more joy out of the entire game and the entire journey that you go through through life. So for me, I think if you can constantly look at your calendar and ask yourself, okay, am I better than I was yesterday? The answer might not always be yes. Let me throw that out there. You might not always be better. But if you can say tomorrow, I'm going to try to be a little bit better and get back on it, that's great. Keep going. Like it's such a chaotic world that we live in, but it's also a beautiful world. So with the chaos and the beauty, just like push yourself to constantly improve yourself, serve others. And I don't think you can not have fun in this journey. Yeah.

59:16
It’s like there are so many things that we can't control but we can avoid regret. I don't know that I've ever regretted improving a little bit. Where can people go to connect with you online and find out more about distribution.ai?

59:41
Yeah. So I'm on all your favorite platforms. You can find me if you do a quick search for Ross Simmonds. I also have a podcast if you want to hear more audio versions from me, Ross Simmonds Show. It's definitely what I would encourage folks to listen to if you want to get a deeper insight into like how I think and what I'm thinking. I release a lot of my unfiltered thoughts directly on that podcast. But I also have a website Rosssimmonds.com and you can definitely check out distribution.ai if you want to hear more from me there. And Austin, major kudos to you. I think you're adding value to the freelance community every day with the work that you guys are doing and putting out there to the world. So keep doing it. And thank you listeners. hope you all got a lot of value and drop Austin five stars on Spotify or Apple, whatever you listen to to get your podcasts.

01:00:23
Thank you, Ross. What a joy to be with you today.

01:00:26
Hey, before you go, let me invite you to join our community for more established advanced freelancers. It's called the freelance cake community. One member named Michelle had this to say, I'm just so impressed by the quality of the conversation that's happening in the group. The in-depth questions, experiments and thoughts being shared are just so refreshing. And the other communities I'm a part of, it's all beginner questions, which is fine, but it's awesome to find a more advanced space where it's okay to ask more advanced questions. Thank you, Michelle. Here's a little more about the community. Each week we do live group coaching and live coworking. You get access to a massive resource library and obviously the community itself, which we host using Circle. Of course, the people are the best part of all this. It really helps to surround yourself. with smart, accomplished, and optimistic people who are out there taking risks and building the businesses they really want. If that interests you, visit http://freelancecake.com/community to learn more and apply. You can find that link in the show notes. I hope to see you there.