I recently had the pleasure of joining the HoldCo Builders podcast for a conversation.
We covered a lot of ground, from the early days of building Tiny and our acquisition of AeroPress, to some of the thought experiments that shaped our decisions.
I also had the chance to share a few stories and lessons learned from my interactions with Charlie Munger and Bill Ackman.
For those who prefer reading, I’ve summarized the main points of our conversation below.
Table of Contents
Watch The Full Episode
You can watch the full interview below, or click here to watch it on YouTube.
Building Tiny
I started by sharing a bit of my backstory, including some early investing lessons I picked up from my dad. This set the stage for the pivotal moment I met my partner, Andrew, and we began our journey together. I explained the “law firm” thought experiment and how it shaped our capital allocation mindset, leading us to the realization that buying proven businesses was a better path than starting from scratch.
Our Investment Philosophy
At Tiny, a core part of our success comes from avoiding bad businesses, especially those with wholesale transfer price risk or high capital intensity. I discussed our preferred deal structuring method, which we call the “bird in hand” vs. the “two in the bush” approach. This discipline was really forged during a two-year dry spell in dealmaking. We also touched on how we evaluate moats and pricing power in potential acquisitions.
Making Deals
I shared the story of how we acquired AeroPress from its legendary inventor, which was one of our more well-known deals. I also talked about the fastest deal we ever did at Tiny and the specific reasons why it worked out so well. A key part of our strategy has been buying what we call “venture orphans” at deep discounts and weighing the benefits of organic growth against price-driven acquisitions.
Our Unique Advantages
We talked about some of the unique advantages that have helped us along the way.
- Location: Being based in Canada has given us both a cost and a headspace advantage.
- Andrew’s Persona: Andrew’s online presence has become an unfair advantage for us in sourcing deals.
- Our Reputation: We’ve found that founders often choose to sell to us because of our reputation for speed, authenticity, and respect.
Lessons from Legends
I’ve been fortunate to learn from some of the world’s greatest investors. I recounted the story of the $57,000 charity lunch with Bill Ackman and what I think makes him so special. I also shared my experience of meeting Charlie Munger—the nerves, the learnings, and having to shout questions at him. These interactions helped reinforce the importance of playing the ultra-long game.
My Decision Frameworks
I explained a few of the personal frameworks I use for making decisions. My main filter is the “hell yes or no” model, which I combine with relativity and gut instinct. I also gave a little masterclass on the power of incentives, using my kid’s allowance as an example. Finally, I touched on how to handle equity and ego in partnerships to prevent resentment from building up over the long term.
Conclusion
My conversation with HoldCo Builders was a deep dive into the practical frameworks and timeless wisdom that have guided us at Tiny. We covered everything from our philosophy on capital allocation to the lessons I’ve learned from some true investment legends. The discussion highlighted our disciplined approach to dealmaking, the importance of managing risk, and how we’ve tried to build unique advantages in the market.
Ultimately, one of the key takeaways I hope people get is that nobody has it all figured out, not even the people who seem to have it all together online. The journey is about continuous learning, disciplined decision-making, and building strong partnerships.
For the full, in-depth conversation, I encourage you to listen to the episode of the HoldCo Builders podcast.