How to be in the right place at the right time
What if success depends not on effort, but on seizing the right opportunity?
Note: this is an edited version of a presentation I made at the Dynamite Circle’s Bangkok conference (DCBKK) in October 2024. At the end of this post I’ll also share what I’ve been up to personally.
In 2015, I started Bobsled Marketing, an agency made up of a rag-tag group of outsiders helping brands navigate the complex world of Amazon and retail media. On paper, I was wildly unqualified - I had never run ecommerce for a large brand. I had never worked a day in an agency. My most recent job was as a commercial banker at JPM Chase! (You can read part one of my story here.)
But within a couple of years, Bobsled became a go-to agency for larger brands. We were getting written up in the press, winning awards, punching way above our weight.
I remember getting a Request For Information — which is the first stage of winning an enterprise brand account — from Nike in 2018. Just 3 years into starting Bobsled! Nike, like other big brands around this time, was realizing they had ignored the importance of Amazon and retail media. Scrappy Amazon FBA entrepreneurs were aggressively taking market share from incumbent national brands.
The big madison avenue agencies working with such brands had no idea what they were doing with Amazon, so these brands started seeking out what they call a ‘challenger agency’. And because Bobsled had been in the game for a little while and were able to ‘talk the talk’, we sometimes made the short list. And sometimes, we won the bid.
So we worked with more mid-market and enterprise brands and I had a nice small business ticking over a couple million in revenue, paying me well, with a great lifestyle.
And then with COVID, Amazon, retail marketplaces and retail media went from an important but delayable growth initiative for these brands, to an immediate imperative.
So all those madison avenue agencies start rushing to actually develop this capability, because they are losing credibility with their clients. They all start looking to buy up independent agencies with good Amazon capabilities, who they also consider to be at a size worth buying. There’s a bidding war on every Amazon agency that serves mid to enterprise brands, of which there’s only a few at that time.
So 2 and half years ago, I sold Bobsled for a life changing amount of money. (Read my Substack post, We Want to Buy Your Company for that story.)
I wish I could say that I was smart enough to plan for this outcome. But this was frankly beyond my wildest dreams in 2015. I didn’t predict that retail media would become the fastest growing form of digital media.
I was in the right place at the right time.
I got lucky.
Owning the role of serendipity or luck in our lives is something many people aren’t willing to do. It feels very fatalistic and not very ‘pull yourself up by your bootstraps’. Type A people are really prone to believe that it's just up to our hard work, our willingness to take risks, or our passion, our street smarts.
But if you’ve read the book Outliers by Malcolm Gladwell, you might have a more nuanced perspective. Gladwell argues that all big success stories involve a tremendous dose of good luck and timing. Bill Gates for example happened to be raised in a school district with very rare access to a computer, so he got his 10,000 hours of programming practice in before anyone else.
The role of luck in these success stories can feel a little deflating, like its mostly outside of our control. From the story I told you about Bobsled, it seems like I caught lightning in a bottle by accident. So if its mostly up to luck, what’s the point of trying?
I can tell you that you can increase your surface area of luck. That you can position yourself to be in the right place at the right time.
Luck happens when you put yourself in an environment where the universe can reward you for being there.
Although luck was part of my story, there’s a few things I did to put myself in that position to catch the lightning. I have 3 luck levers to share with you today.
1. Find a hungry crowd
What does it take to operate a successful hot dog stand?
It’s not having the lowest price.
It’s not having a clean-looking stand with good signage.
It’s not even having a better quality hot dog.
It’s finding a hungry crowd.
A hungry crowd will overlook high prices, a grimy sign, even a not-so-great-tasting hot dog.
Now what I didn’t tell you is that Bobsled was my second business. My first was a brand of craft supplies for people to make their own lamps and lampshades. I really took that "niche down" advice to heart.
Would it shock you to hear that business was… slow?
I believed that if I just worked hard enough, I’d crack the code. I thought I needed better tutorials, more volume for better prices, more PR. I tried everything—new products, YouTube videos, hiring an employee. But no matter what we did, every dollar felt like squeezing blood from a stone. (You can read more about this here.)
Then I started Bobsled, with a completely different model, and it hit me: I wasn’t the problem.
There was no hungry crowd.
Bobsled which was solving a huge pain point for brands that were desperate for help. Like the hot dog stand, they weren’t looking for the cheapest option—they wanted the agency that could credibly solve their issues.
So the takeaway? Solve a problem worth solving. Be honest about your market. Is it big enough and hungry enough to meet your ambition?
Find your hungry crowd.
2. Be visible
Starting out in 2015 I had no marketing budget, no big client logos, no personal brand, and no case studies. It would seem I had no right to be there. But I could share what I was learning in real-time — both from the lamp business and our initial client work.
So I started writing tons of content about Amazon, about their systems, about new features and updates.
After years of plugging away with blog posts and industry commentary, we had a corpus of content behind us that showed we knew what we were talking about by the time the real wave of corporate interest hit in 2017. Based on this foundation was invited to contribute to Forbes, to speak at events. I have even been cited in federal lawsuits against Amazon.
This all meant that when an ecommerce director at a CPG brand was tasked with finding an agency to help manage their retail media or dial in their Amazon strategy, we showed up where they were searching, on the issues they were concerned with. So then the agency was invited to an RFP.
By sharing your observations and what you're learning in real-time, you get to see what other people are interested in too. For example in 2020 I started sharing more about Instacart’s new self-serve advertising platform, which got traction among our audience of CPG brands. Other solution providers weren’t paying it much heed, so I decided to double down and publish a book titled Instacart for CMOs. It seemed niche at the time but set our agency apart as a first mover with this ad platform.
But there’s another benefit of being visible that goes beyond finding your next client.
The company that acquired mine did so because of all the relationships and reputation that Bobsled had built over time. It was from collaborating with one specific software company in the past that I got introduced to the company that would eventually acquire Bobsled.
Being well known and well liked in your industry is one powerful pathway to allow good fortune to find you — whether that’s new business, partnerships, or even potential acquirers.
3. Reposition
One important detail in the story of Bobsled is that we didn’t immediately jump right into working with these big brands. Because I had absolutely no credibility in the space when I started, we had to start with tiny startup brands, and work on a contingency basis — which a lot of the time meant working for free because they would run out of inventory or just find a way to weasel out of paying me.
But eventually after developing some skills and expertise we were able to win bigger clients, who were not only willing to pay more, but were generally easier to work with than the little guys!
To do this, I had to learn what was important to these bigger brands, what skills and expertise they considered to be rare and valuable.
For example, small brands care about:
Price
Speed to execute
Immediate results
But large brands care more about:
Credibility
Ability to navigate RFPs and corporate bureaucracy (‘talk the talk’)
Managing downside risk
So to begin appealing to this market, I focused on building things that would meet their requirements. Let’s take credibility for example. There were a number of ways to skin this cat. I could have brought on a key employee or advisor or partner with the professional network that I lacked, for example. But I took the approach of thought leadership which was a much slower burn but cost less money upfront.
That required showing up in the right publications, talking in their language, and sharing content relevant to their goals. All of this took several years. But it meant that when the big wave of Amazon and retail media started to crest, I was there, and I was ready to ride it.
In the case of my first business, I probably should have just cut bait and moved on. Considered it the first step on my ‘stairstep business’ trajectory.
But perhaps your product/service is actually great, but it’s not serving the right market. Or the market is okay, but there’s a more lucrative one out there.
So consider — is there a better market you can serve with the same product or service?
If that’s the case, you need to learn what’s important to them, what is rare and valuable, and cultivate those skills.
Conclusion.
If you’re reading this, you’re already one of the luckiest people who have ever lived.
Think about it:
We don’t have to go hunt for our next meal.
Women are no longer considered the property of our husbands.
We are working on the internet, an invention that’s only 41 years old.
The rest of your good fortune, you can cultivate. By positioning yourself in the right places, by staying visible, you increase your chances of catching lightning in a bottle.
So as you move forward, don't wait for luck to find you. Instead, make sure you're always in the places where it tends to show up. When the opportunity comes, you’ll already be there.
Personal updates
I’ve fallen into making this Substack very essay-heavy, as it’s something that Substack seems to be pushing for. But I also realize that many people who subscribe are interested in what’s going with me personally. So I’ll share some recent updates!
After an incredible 3 months of travel, I have landed back in my hometown of Perth with my family on Monday. We visited Turkey, Croatia, Slovenia, Denmark and Thailand. It was a wonderful year to travel due to my work sabbatical and our son being 7 years old and quite happy to hang with mum and dad for months on end. We did send him to summer camp on the island of Hvar in Croatia and a drop-in school in Thailand so there was also plenty of kid time. Highly recommend both of these if you have school-aged kids BTW.
We do intend to return to the US in summer of 2025 after spending the Australian summer in Perth and perhaps a bit more travel.
I took up road cycling while in Thailand which was an incredible place to first learn to ride in a group. Hua Hin was the town we were based in, and there’s a great riding group there (shout out to Hua Hin Roadies). Thai drivers are very patient and the scenery was great.
I’m preparing for a 10-day cycling tour with my dad and brother in Taiwan in December. So now we’re in Perth I need to get a road bike and join a club.
On the work front I don’t have anything to annouce yet. But I am planning to dip my toe back in to the world of retail marketplaces & retail media 🤩
Best recent purchase was this Vaughan 12ft extension pole with attachments for clearing out the cobwebs on some high ceilings. I didn’t appreciate just how much they were bugging me.
Thanks for reading!
Kiri