I Failed at 6 Businesses Before This One. Here's What Each One Built in Me.

In 1948, David Ogilvy arrived in New York City with $6,000, no clients, no credentials, and no experience writing advertisements. He was 38 years old. What came before that moment was seventeen years of getting expelled from Oxford, working in a hotel kitchen preparing meals for customers' dogs, selling stoves door to door in the Scottish Highlands, farming with the Amish in Pennsylvania, and failing at most of it.

Eleven years after opening his agency, he had every client on his wish list. Time magazine called him the most sought-after wizard in advertising. He became known as the Father of Advertising. And when people asked how he did it, he pointed back to the years that looked like nothing and said none of it was wasted.

Andrew believes him. Because over the last decade he has started a merchant services company, a financial blog he stopped at five articles, a vehicle wrap business called Dryvr that signed up over a hundred drivers and never found a single paying client, a solar domain name venture that earned him a hundred dollar deposit and a lesson, a follow-up email business that worked but wasn't worth building, and two Amazon number one bestsellers that felt significant and then quietly faded.

This episode goes back through every one of those failures, not for the story but for what each one actually built. The skill, the self-knowledge, the judgment, and the internal capacity that made everything that followed possible, including this podcast.

What season are you in right now that feels like a detour? What if it isn't?

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Transcript

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Every week I get to see behind the scenes about the data of how many people are actually listening to this podcast. We have people in Japan, Australia, Southern America, and North America that are tuning in on a weekly basis to hear some of our incredible guests. But one of the best things to continue growing that reach is if you would actually hit subscribe or follow. This helps with the metrics so that way you are the first one to get notified when new podcast episodes drop, but also it continues to spread that reach to other individuals who might need to hear some of these incredible lessons that people are sitting on the opposite side of the table from me are sharing. So do me one favor today and hit subscribe. Thank you. In 1948, David Ogilvy arrived in New York City with $6,000 in his bank. No clients, no credentials, and no experience writing advertisements. He had not written a single line of copy in his life. Yet he became one of the most prolific advertising writers ever. He was 38 years old. And what makes it remarkable is that what the previous 17 years looked like before, he was expelled from Oxford, went to Paris, and worked in the kitchen of the Hotel Majestic, where his assignment was preparing meals for customers' dogs, a dream job for any inspiring chef. Went back to England and sold cooking stoves door to door in the Scottish Highlands, was so good at that that he actually wrote a sales manual, which 30 years later, the editors of Fortune magazine would call it the best sales manual ever written. Then he emigrated to America, worked for a research institute, served in British intelligence, and during the war tried farming with the Amish in Pennsylvania, and he failed at that too. At 38 years old, he was broke and uncertain. He opened an advertising agency with no advertising experience at all. He made a list of the five clients he wanted most: General Foods, Bristol Myers, Campbell Soup, Lever Brothers, and Shell. 11 years later, he had all of them. In 1962, Time magazine called him the most sought-after wizard in today's advertising industry. He became known as the father of advertising. He built one of the most influential companies in the world. And when people asked how he did it, he pointed back to the years that looked like nothing. The kitchen serving meals to dogs, the stove sales, the farm, the intelligence work, and he said, none of it was wasted. And I truly believe him because I feel the exact same way. Over the last decade, I have started a lot of things that didn't work. The first was a merchant services company. I was selling machines you use when you're buying something at a store. I would print booklets out of my own pocket, my own money, my own time to find out afterwards that those booklets were completely done incorrectly and they were basically unusable. I still went and knocked on door to door of local businesses with the materials that barely made any sense and tried to sell something I had no authority to sell. I got turned down over and over again. Then I started a blog about Emily's and mine financial journey, the Canadian Cash Cow. I wrote five articles and then I stopped because I didn't create a plan. I thought millions of people would come running just because I wrote something, but I realized that wasn't going to be it. So then I tried selling domain names for solar panels in specific demographic areas. I made one sale. The guy gave me a hundred dollar deposit and then completely ghosted me. Then I had what I thought was a geniusly good idea. Wrap other people's vehicles in advertisements for local businesses. I called it driver. It was going to be like Uber, but for business logos. Over 100 people in my community signed up to have their cars wrapped with different advertisements. But the problem was I couldn't get to businesses to trust people with their logo. They were worried about what happens if someone gets an accident or speeding ticket or whatever it might be. See if the supply was there, but the demand never came. Then I started writing follow-up email sequences for sales professionals. We got clients. The business actually worked, but the amount of work and effort relative to what we were earning wasn't truly worth it. So I stopped. Then I wrote two books that became Amazon number one bestsellers. The ranking was real, the moment felt significant. And then it passed. And nothing structurally changed other than a deposit from Amazon once in a while. During all of this, I had a new idea almost every other day. And Emily, to her enormous credit, shut most of them down before we even started. I was frustrated at that time. And I'm deeply grateful for it now. See, I feel like David Ogilvy arriving in New York, knowing that he had talent, but just was unsure exactly where to put it to work and how to remain consistent. So I want to go back from my list of failed accomplishments, not because I actually want this unfortunate reminder, but because each one of them taught me something I'm using right now. It's the merchant sales booklets, walking into businesses with materials that didn't work, getting turned down repeatedly, having no authority and no backing that taught me how to actually communicate with business owners, how to walk into a room that nobody is asking me to come into and find ways to have real conversations with real people, to not get mad or blame others, but to take real-time feedback and improve the way that I'm communicating. The blog I stopped at five articles. At the time, I told myself it was because it was too much work. The real reason was about consistency. I didn't have it yet. I wasn't ready to build something that required showing up the same way, day in, day out, over a long period of time. This podcast exists because I learned that about myself and then built the internal capacity to do it differently. Creating systems and a backlog of content to pull from. That vehicle wrapping business. I went for easy things first by getting people to sign up to be paid for advertising. Of course, everyone wants to get paid. But what I should have done was pursue the hard thing first. Going after businesses to sign up and knowing that the rest would follow. I create a false hope with easy wins instead of doing the real work first. The solar domain names, the idea was borrowed from someone else's playbook, and it was already outdated by the time I tried it. The lesson was to think about what's relevant now, not what worked for someone else in a different moment, but actually how can I modify this to today and what's working now? The follow-up email business. We got clients, the thing actually worked, yet I still stopped because I learned something more important that whether something can work, I learned to ask whether it's worth building. Time versus effort is a real calculation. Not every working idea is the right idea. The Amazon best-selling books, this one is the most important lesson on the list, I think. Marketing can create a moment. A number one ranking feels like a proof of something, but a moment is not a movement. The lesson was to focus on things with long-term roots, not things that feel good briefly and then fade into the background. I think about that every time I record an episode of is this gonna have long-lasting impact? And Emily, shutting things down. I used to push back on that. Looking back now, though, I see the grace in it. She was protecting my focus. Not every idea deserves your energy. You need a corrective voice in your life, someone who loves you enough to say, not that one, I mean it. Here's what Ogilvy understood that most people miss. He said of his Oxford expulsion, the thing he called the real failure of his life, that was possibly the first stroke of accidental genius, the thing that forced him out into the world where his actual education would begin. The kitchen taught him discipline and when to move on. The stove sales taught him how people actually make decisions. The farm taught him humility. The intelligence work taught him how to write under pressure and how to distill complex things into clear ones. None of it looked like preparation for building the most influential advertising agency in history, but all of it was. When he finally opened his agency, the 17 years of seemingly random experience became the foundation nobody else had. He understood people because he had served them, sold to them, studied them, and lived among them. He had earned a kind of knowledge that couldn't be taught in a classroom or acquired by going directly to the destination. There's a moment in his story that I keep thinking about. When someone was made the head of an office in his company, he would send them a set of Russian nesting dolls. Inside the smallest doll was a note. It read, If each of us hires people who are smaller than we are, we shall become a company of dwarfs. But if each of us hires people who are bigger than we are, we shall become a company of giants. He learned that from the years of being the smallest person in the room, from preparing food for dogs and getting turned down at doors and watching a farm fail. You cannot teach someone to hire giants if you've never had to become one yourself first. This podcast is the business thing in my life that is probably the most woven into the fabric of who I am as a person. Yet it's also the thing that I'm the least attached to out of all those business ideas. And I know that's a weird contradiction. See, every business I tried before, this one, was attached to my identity in a way I didn't fully understand at that time. When the booklets didn't work, it hurt personally. When the domain name deal fell apart, it stung. When the Amazon ranking faded, there was a quiet deflation underneath the celebration. Because I was using those outcomes to answer a question about who I was. See, I've done enough internal work now that I don't need the outcome to answer that question. I know who I am before the results arrive. That's what character-based confidence actually looks like when you're living in. Not that you care less, but that your worth isn't riding on it. Ogilvie built an empire. He also failed at Oxford, failed at farming, and started his company with $6,000 and no experience at the age of 38. He didn't succeed in spite of those seasons. He succeeded because of them. Every one of them built something in him that the destination alone could never have given him. The detours are the point. Not because failure is romantic or because struggle is a badge worth wearing, but because the seasons that feel like they're taking you off course are often the ones doing the most important work, building the competence, the resilience, the self-knowledge, and the judgment you are going to need for the things that actually last. Nothing is wasted. Not the booklets that didn't print right, not the five blog articles, not the hundred car wraps that never happened, not the solar deal that earned me $100 and a lesson, not the email business that worked but wasn't right. Not the bestseller that felt big and then eventually faded. Not a single conversation with a business owner who told me no. It was all building something. I just couldn't see it from the inside out. So here's what I want to ask you. What season are you in right now that feels like a detour? And what if it isn't? What if that detour is exactly where you need to be? And how are you choosing to embrace it? If this episode had an impact on you, I want to encourage you to hit that subscribe or follow button. It helps us to continue grow our reach as well as it helps you to make sure that you don't miss a single episode. Thank you.