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LATEST POSTS 📚

If you’re new, not yet a subscriber, or just plain missed it, here are some of our recent editions.

🦆 Why MotherDuck Bet Against Big Data. An interview with Jordan Tigani, Co-Founder & CEO at MotherDuck.
🧸 Why AI Pivoted To Cute. How companies are pivoting their brands to be mascot-led.
🌊 Why Payroll Is Still Broken (And Fixing It). An interview with Ayush Sharma, Founder & CEO at Warp.

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HOUSEKEEPING 📨

AI branding needs some serious work. I stayed with a family in New Zealand earlier in the year when visiting for some hiking and got eye rolls when I told my hosts that I worked in tech, and even bigger eye rolls when I said specifically AI. It’s not surprising. This tweet sums it up pretty well.

In what universe would you expect the general pop to be excited about AI when we talk in such dystopian ways. The entire population in China are AI bulls; they think it’s going to cure cancer, supercharge the economy, reverse climate change. In the west, we are just running around screaming like an underslept Sarah Connor. I’d love to understand more about what China is doing differently. Anywho, enjoy today’s piece.

BUILDING IN PUBLIC 🔎

You Either Win, Or You Learn

I heard the phrase, “You either win, or you learn,” once, and I never forgot it. Reminds me a little of the famous Air Jordan quote: “I've missed more than 9,000 shots in my career. I've lost almost 300 games. 26 times, I've been trusted to take the game-winning shot and missed. I've failed over and over and over again in my life. And that is why I succeed.” Use whichever catchphrase or famous quote you like; the fact is, failure is part of being human. Life itself is one big, long series of learnings at best, failures at worst.

That’s part of the fun, though. There's real beauty in evolving. Picking up new observations about the world. Life is interesting because it’s a challenge, not in spite of it. The sooner you accept the fact that you are a fuckup in many ways, the more at peace you will be. Bookworm → butterfly.

Case in point: me. So far, I’m the definition of a life well lived. I’ve traveled the world, fallen in love, built businesses, renovated houses, and more. But I’ve also been broke, let people down, made simple errors with big consequences, and, worst of all, made self-interested decisions that hurt others. Today, I’m engaging in catharsis. I’m sharing four of my biggest mistakes: the ones that cost me a friend, a school camp, a small fortune, and very nearly my company. I’m nervous about how this will go, but let’s dive in!

1/ Upper Deck, lower class

My first loss was in grade five at Boneo Primary School, in a basketball swap deal that went so right that it went wrong. The deal in question was over a 93-94 ‘silver signed’ Michael Jordan Upper Deck card. If you were a kid in the 90s, you’ll know what I’m talking about. Upper Deck, one of the most popular 90s trading card brands, had a signature series where, if you were lucky, you could land a bronze, silver, or gold signed version instead of a regular card.

I was lucky enough to open an Upper Deck pack and find a silver-signed Mike baseball card staring back at me. No, it wasn’t the gold-signed. The silver-signed, though, was still worth a small fortune for a snotty-nosed 12-year-old. $80 USD was the going rate in Beckett, the Wall Street Journal of the trading-card market.

As a total basketball nerd, I would make my parents take me to the local news agency every day in the lead-up to the new Beckett dropping, something which usually happened a few days shy of the new month. One morning, while reading the newest edition, I noticed to my shock and horror that the bottom had fallen out of the Michael Jordan market. The 88-89 Fleer had been slashed by 40%; Topps Finest refractor down even more again. As I frantically flicked through the listings, I saw it: my silver signed card, the ticket to making it in this life, down 50%. FIVE-ZERO.

The realization hit me like a knife to the heart. What would I do? Then it came to me. My friend Garth had been pleading with me for months to do a deal for my MJ. $90 worth of cards he’d offered, $120, $140. I’d knocked him back every time. It was at this point I knew what had to be done, so that next morning, armed with the new market intel, and knowing that the new Beckett wouldn’t start circling in school for another few days, I strode into class and made the proclamation, “Garth, I’m ready to swap my MJ…but I want double. I’ll only do it for $160.” You could hear our schoolmate gasp in shock. “Let’s do it,” Garth replied. The trade was on.

Over the next 45 minutes, with 15-20 school kids huddled over us, Garth and I laid out his entire basketball card collection, and I had my way with it. Ten Shaqs, seven Ewings, a handful of silver signed by lesser players, all the way to the figure we’d agreed upon: $160 USD worth of cards. We shook hands and walked away. I had won. Little did I know it was a poisoned chalice.

Three days later, I walked into school only to be confronted by an emotionally distraught Garth, running at me, tears running down his cheeks. “You ripped me off. I want my cards back. You are a crook. I hate you, I hate you, I HATE YOU.” Sure enough, like clockwork, the updated Beckett was doing the rounds, and Garth knew he’d been played. As we wrestled and fought, I told Garth the deal was done, his cards were at my house, safe and secure, and they weren't coming back.

It was true that I’d outsmarted Garth. But I hadn’t bet on my friends, Garth’s friends, or even the teachers and parents, hearing about the deal. They knew I was trading on pre-pubescent insider information. He’d called me a crook, and he was right. I realized then and there that winning this deal didn't feel like joy, happiness, or pride. I felt embarrassment, ridicule, and shame. Never again would I do business in an untoward way. The risk to my reputation was too high, and the feeling of shame was not one I’d like to revisit.

2/ “Your son instigated a riot in Italian”

The next loss I took was in year nine, at Padua College, and it began in Mr. Cusseigh’s Italian class. During my time at Padua, my year level was the bad year level, the one with all the naughty kids, and I was the leader. My Italian class was put together as if the class scheduling person (not sure who does this) hated Stephen Cusseigh and wanted to put him through pain. Of the 20 worst kids in our year level, 16 were in this particular class.

On this fateful day, Mr. Cusseigh was out on an excursion, so not one, but two substitute teachers, Ms. Wilkinson and Ms. Wilson, were sent in his stead. Being the class clown that I was, during the class I continued to put my hand up to ask, “Ms. Wilkinson/Wilson, where is Mr. Cusseigh?” to which they’d reply, “We’ve told you, Bill; he’s on an excursion with the school’s soccer team.” Unhappy with the calm reaction I was getting from the teachers, yet not quite knowing my next move, I leaned back into my chair, and to my shock, I saw Mr. Cusseigh on the school’s back oval, kicking the soccer ball around as if he hadn’t had a care in the world.

What happened next was a blur. I flew into what could only be described as some sort of exhilarated rage. I jumped from my seat and screamed, “Mr. Cusseigh isn’t on an excursion; Mr. Cusseigh is right there.”

I jumped to my feet and banged on the back windows of our crappy little portable classroom, yelling, “Missssterrrr Cusseigh, Misssterrrr Cusseigh.” A moment later Isaac joined me. “BILL, STOP THAT, ISAAC, SIT DOWN,” rang out from the voices of our substitute teachers. But the more they yelled, the worse it got, as one after another of the 14 other bad kids rushed to the back of the room, banging on the windows and screaming for our beloved (I don’t actually know if we liked him) Stephen Cusseigh.

What happened next was positively biblical. Like a swarm of harmless grasshoppers turning into marauding locusts, the last remaining good kids rushed to their feet to join in the chorus. By this point, 30 frenzied, feral, wild children were banging on the windows and screaming for Cusseigh. The entire classroom was swaying. Then Mr. Cusseigh glanced left, spotted us half a mile away, gave us a polite nod, and the whole group erupted in cheers. We hugged and high-fived as if we’d just won the World Cup. It was pure elation.

The whole experience lasted only 30 seconds, but it felt like a lifetime. As the celebrations died down and my adrenaline began to fade, my ears picked up the teachers' screams. And then I heard it over the school’s loudspeaker: “Bill Kerr to the principal’s office…IMMEDIATELY.”

What followed was a two-week suspension from school, citing “incitement of a riot” in the letter to my parents. But the killer was that I was also suspended from the Year Nine camp to Camp Howqua, known to all as Padua's greatest camp, and something all kids look forward to as soon as they arrive. This was the first time that I’d really learned that if you push things too far, there can be real-world consequences. The Lord giveth, and the Lord taketh away.

3/ 2008 & the GFC

My next lesson came when I was on top of the world, personally and professionally. I’d bought my first house at 19, my second at 21, a block of land at 22 that I planned to build on, and a signed offer on a fourth property after that. The house I was building was a 34-square (aka, very large) house on a 1,000-square-meter block, 20 meters from the beach in St Andrews Beach. The house had four bedrooms, a large outdoor patio, two living areas, and even a cinema room.

To build on the block, though, I needed to sell my second home: a small beach shack in the suburb I grew up in. After a great little cosmetic renovation—new roof, paint, kitchen, decking—I put the house on the market, with a five-week advertising period leading up to the auction.

It was 2008, and the Australian real estate market was on fire. So much so that my then-girlfriend and I took off for a holiday, meeting the rest of my family for a week in the Pacific island of Vanuatu in the middle of the campaign. One afternoon, after a day of beach adventuring, swimming, snorkeling, and more, we returned to the hotel to relax. I reached for the remote, turned on the only English-language channel available, CNN, and was greeted by the news flash: ‘World’s markets are in freefall; they are predicting the worst recession in decades.’

At that moment, a chill went down my spine. ‘If I can’t sell this house, I’m in trouble.’ A week earlier, I had been on track to make $100k+ on the sale of the beach shack. $80k on a bad day, and $120k or more if the Gods were on our side. On auction day, the house passed in without a bid. After many sleepless nights and a truckload of stress, I would eventually sell the house a month later for $100k less than I expected. I broke even on paper (I sold it for what I bought it for), but that didn't account for the renovation costs, buying and selling costs, or the blood, sweat, and tears.

Worse, this loss led the bank to reassess and audit my financials, subsequently withdrawing my pre-approval for both the fourth house and the build, which was about to kick off. What they did by withdrawing my pre-approvals may have been illegal, but once it was done, there was no way, in the middle of the GFC, another bank was going to come in and fill the gap. By being over-leveraged and assuming Black Swans don’t exist, I lost hundreds of thousands of dollars. Life-trajectory-changing money at such a young age.

4/ 2022 (EOR + near layoffs)

During the peak ZIRP and the 2021-2022 hype cycle, my hubris was white hot. The good news is I wasn't alone. Founders all across the globe were blockchain-washing their pitch decks, raising money at unsustainable multiples, and releasing custom NFTs to commemorate their biggest enterprise deals. Sanity was then; shiny object syndrome was now.

During this period, we at Athyna—and by ‘we’ I mean ‘I’—made innumerable mistakes. We hired too fast, took on debt to accelerate growth, launched products we didn’t have the capital to scale, and even acquired a small carbon-offsetting company for no reason other than it aligned with ‘our values.’

Our biggest blunder was building and launching EOR to accompany our Talent (hiring) product. EOR, short for Employer of Record, was all the rage, with companies like Deel, Remote, and Oyster raising eye-watering sums of dinero on a seemingly quarterly basis. We thought (again, mainly me) that EOR would accompany our core offering well. Not only could we find the best talent, but we could employ them compliantly on your behalf.

EOR is an incredibly capital-heavy product to launch. You have two options: 1) build and maintain entities all over the world, or 2) white-label from other EOR partners, giving up the majority of your margin. This is the reason companies like Deel were raising so much, so fast to get to market.

No problems, we thought: After a few early ‘testing the waters’ investor calls with Sequoia, GGV, TCV, and more, we were told to push our revenue as hard as we could because, in the words of one GP: “You’ll raise easily at 100x revenue. If you go in with anything under 60x, no one will take you seriously.”

This is where the debt element came in. My thinking was simple: if they say they’ll give us 100x at the drop of a hat, then let’s get that ‘X’ as high as humanly possible, and fast. To do this, we went to the predatory revenue-based financing providers like Pipe, Capchase, and Jeeves. We took on loads of debt, hired as fast as we could, and grew for a while there at 20% or so a month. This was the time to raise. And on May 17, 2022, we opened our round. We were raising $10M at a $45M valuation.

The 17th of May also happened to be the day Netflix announced their first mass round of layoffs. This was the ‘Huh, that’s weird’ stage of the cycle. After Netflix, though, more came, and more whispers. The market had been too hot for too long and was now getting compared to the Dot Com Crash of 2000.

While the market was crashing, we were out there raising. We had calls with 16 of the world's top 20 funds. Things were still going swimmingly, though you could feel the rug getting tugged out from beneath your feet. After a sneaky revision down, we got very close to terms, raising $5M at $25M with a mid-sized fund out of Austin, Texas, only for it to be nixed at the final stage due to a conflict of interest. We were still hiring and burning debt while our fundraising timeline tightened by the day. Our $45M valuation had already been slashed to $25M and now again to $20M.

Around this point, I stopped believing in our raise and started thinking I’d fucked up the timing. Money was tight, we were using debt to service debt, and the market had officially crashed. We had one final gasp of air with a European fund that was incredibly keen. But I’d lost the fire. We were set to pitch their investment committee on this new future, centered on EOR, while I spent all day and night scenario-planning for layoffs and figuring out how to tell the team we were killing our vision. So I promptly reached out to the fund and canceled the pitch.

Friday of that same week, I told our senior leaders we’d be making major layoffs Monday and to start thinking about their teams. We’d built a few scenarios with the team, ranging from cutting at least 15% of headcount to as high as 40%. But over that weekend, I changed my mind.

After running the numbers for the thousandth time, I found a few extra dollars here, some more there, and decided that if we really wanted to burn the boats, we probably did have one full month left in us. So come Monday, I reached out to our leaders and told them we were backing the team for another 30 days. Later that day, I told the larger team we were cutting EOR and all new products and going back to our core. The excitement at the bold decision was actually palpable. “We are going to grow our way back to life,” I screamed in my best Leonardo DiCaprio-as-Jordan Belfort voice.

_{*I didn’t really scream it, but it would have been awesome if I had. Pretend I did for now.}

So, did it work? In the 30 days that followed, we had an immediate surge in energy, and had our best month of growth in almost a year. By the time three months had passed, we were officially out of the woods, edging closer and closer to profitability, and regaining ownership of our destiny.

I take layoffs very seriously. We’ve only ever had to make them once, a year in, during the peak of COVID. I plan never to do it again. We still carry a sliver of debt from that period today, a little reminder sitting on the balance sheet. Looking back, the turnaround came down to a few unglamorous calls: killing EOR fast, cutting every non-core product, and telling our leaders exactly how long we had.

The learnings here were many. Debt sucks. Don’t assume the music will always be playing. And when things get tight, cut products before you cut people.

Playbook / how you can apply this

• Run the Garth test: Before you close any deal, picture the other side finding out everything you knew. If your gut says ‘embarrassed,’ walk away. Wins that cost trust are just losses on a delay.

• Know where the line is, then stay a step behind it: Pushing boundaries is how founders win. Pushing them for a 30-second dopamine hit is how you miss camp. Ask what the downside is before the adrenaline kicks in.

• Assume the Black Swan is coming: Stress-test every big bet against the worst case, not the base case. If one failed sale, one bad month, or one bank saying no can wipe you out, you're overleveraged. Keep enough runway to survive being wrong.

• Treat debt and hype like tequila: Great for a night, terrible as a strategy. When an investor promises 100x, treat it like a weather report. Never borrow against a valuation you haven't banked.

• Protect the core, kill the sideshows: When it gets tight, cut the shiny new products before you cut people. Going back to what you do best, with a team that knows you backed them, is often the fastest way to grow your way out.

Summary

Hopefully this was a fun read, and a reminder that even in the strangest experiences of your past, you can always find a good lesson. For me, the lesson in most of these cases was to be careful not to always chase more, more, more. More basketball cards. More home equity. More trouble. More growth.

The good news? I’m still learning. The bad news? I’m still learning. There are plenty more failures where these came from, and a few I’m not quite ready to write about yet (Part Two, anyone?). For now, I’ll take MJ’s advice: miss the shot, own it, learn something. Then go take the next one.

Extra reading

• Getting To Know Me: Sliding Doors - January, 2026

• Building Culture & Resilience: Bill Kerr of Athyna Interview - September, 2026

• We Raised $2.5M To Build Athyna AI - May, 2024

• Open Sourcing My Investment Portfolio - April, 2025

And that's it! You can follow me on Twitter and LinkedIn, and also don’t forget to check out Athyna while you’re at it.

BRAIN FOOD 🧠 

TWEETS OF THE WEEK 🐣 

TOOLS WE RECOMMEND 🛠️

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See the full set of tools we use inside Athyna & Open Source CEO here.

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