"AI will replace everyone" — everyone, 2025.

Bold Predictions

The obvious prediction is often wildly wrong. Technology rarely kills whole industries. It kills the average and sends their customers to the best.

We've seen this pattern before. The consensus says an industry is doomed. Then it adapts, evolves, and sometimes hits record numbers.

What Actually Happens

Here's the thing. The mediocre players get wiped out. But the exceptional ones? They absorb all that displaced demand. The pie doesn't disappear. It just gets redistributed to whoever's actually good at what they do.

The Takeaway

Don't bet against entire industries just because new technology shows up. Bet against the average performers who can't adapt.

The pattern repeats itself. Travel agencies were "dead" in 2004 and just posted record revenue twenty years later. AI won't replace everyone. It'll replace the people who refuse to get better.

Be the exception, not the average.

Fun Facts

• Tiny is publicly traded on the TSX Venture Exchange under the ticker TINY
• We own and operate over 30 businesses
• The company is headquartered in Victoria, BC, Canada
• Our approach is inspired by Berkshire Hathaway: we buy profitable businesses and stay out of their way
• We can make offers within 7 days and close deals in as little as 30 days
• Deal sizes range from $1M to $300M

Origin Story

Our goal was audacious: to create the Berkshire Hathaway of the internet.

Before that, we had tried everything. Productivity apps, skincare brands, you name it. Some worked, many didn’t. But each failure taught us something valuable about capital allocation.

We realized we were doing it all wrong. Instead of starting new businesses from scratch, we could apply Berkshire Hathaway’s model to internet businesses. We buy profitable businesses and then stay out of their way. No unnecessary meetings, no forced synergies, just support when needed.

Companies

As of January 2026, here are some of the companies in our portfolio:

• Metalab
• Letterboxd
• Serato
• AeroPress
• HappyFunCorp
• Z1
• Dribbble
• Creative Market
• Stamped
• Conference Badge
• Four Sixty
• KNO
• Orbit
• Pixel Union
• Archetype
• Clean Canvas
• Girlboss
• Flow
• Designer News
• Meteor
• Castro
• Medimap
• Supercast
• MediaNet Solutions
• DoubleUp
• Out of the Sandbox
• 8020
• Abstract
• Norbauer & Co.
• Wholesale Pet
• BeFunky
• Mateina
• SuppleApps
• Yopify
• Websterpeace
• Mailman
• We Work Remotely

More Information

For more information about Tiny, visit the company website at www.tiny.com.

You can also find investor information at investors.tiny.com.

Related Reading

• 

  Building Tiny: Our Journey to DEYA Recognition

  Feb 4, 2025

  I was recently honored alongside Andrew Wilkinson as Distinguished Entrepreneurs of the Year by UVic’s…

• 

  Distinguished Entrepreneur of the Year Award

  Jul 2, 2025

  Last month, Andrew Wilkinson and I were honored by the Gustavson School of Business at…

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  Why Businesses Get Messy Over Time

  Nov 1, 2024

  I look at my neighbor’s abandoned garden and it hits me – this is exactly…

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  HoldCo Builders Podcast: Capital, Deals, and Lessons Learned

  May 30, 2025

  I recently had the pleasure of joining the HoldCo Builders podcast for a conversation. We…

They put on a thoughtful, warm evening that gave us a rare chance to pause, reflect, and appreciate the people who’ve been part of the journey.

Learn more about our holding company and our journey building it.

Here are some photos worth sharing.

Thank you to University of Victoria and everyone who made the night what it was.

Follow me on X and Patron View for more content like this.

They had the best intentions, but the outcomes were far from what I had hoped.

Why Perfect Advice Fails in Your Reality

Advice is often like being given the perfect recipe, but your pantry’s full of different ingredients. The context is never the same.

You’re working with different timing, a different team, and different tools. What worked flawlessly for someone else is being applied to a completely unique situation—yours.

The Hidden Strings Attached to Advice

Once someone gives you advice, they get invested in you following it. There’s a new pressure that didn’t exist before.

If you don’t follow it, they think you didn’t listen. If you do follow it, and it backfires, well, that’s on you. The responsibility for a failed outcome, stemming from someone else’s suggestion, ultimately rests on your shoulders.

The Unfiltered Power of Stories

Stories, on the other hand, don’t come with strings. They are a pure transfer of experience without the burden of expectation.

They let you hear what someone actually did, analyze the components of their journey, and figure out for yourself what pieces, if any, fit your situation.

Conclusion

The next time someone offers you advice, politely decline and ask for their story instead. Ask them to walk you through what they actually experienced—the messy details, the unexpected turns, the things that almost derailed them.

You’ll get something far more valuable: raw material you can process through your own judgment, shaped by your unique circumstances and constraints.

Because the best decisions aren’t made by following someone else’s blueprint—they’re made by understanding the principles behind their success and adapting them to your reality.

Your situation is one-of-a-kind. Your solution should be too.

Follow me on X and Patron View for more content like this.

Over the past year, Tiny has navigated challenges that have sprouted a few new gray hairs, but the company has emerged stronger from them.

It was a year of hard-learned lessons, optimization, and compounding growth that has positioned the company for continued success.

Financial Performance Highlights

Some of our highlights.

Ten-Year Track Record

• 10-year CAGR: Revenue 37%, EBITDA 25%.

Q4 2024 Results

• Q4 Adjusted EBITDA jumped 38% quarter-over-quarter as the company's cost-cutting program kicked in.

Recurring Revenue Growth

• Recurring revenue is up 4× since 2021, now reaching $39M.
• Expected to jump to $64-66M ARR with Serato integrated.

Major Strategic Moves

Some of our big moves.

Debt Management

• Paid down $24.5M of debt, strengthening the company's financial position.

Serato Acquisition

• Closed a 66% stake in Serato for US $66M.
• Expected to lift consolidated EBITDA approximately 45%.

Tiny Fund Performance

The Tiny Fund has been fully invested and is performing strongly:

• Doing around $66M of revenue (+17% year-over-year).
• Sent $2.2M of distributions to HQ.

Portfolio Company Highlights

Some of our portfolio's highlights:

• Letterboxd users doubled to 20M.
• AeroPress revenue up 120% since acquisition.
• Mateina with Huberman revenue up 100% year-over-year, rolling out to all Whole Foods locations in the USA.

Operational Efficiency Initiatives

How we're ensuring our operations are efficient.

Cost Optimization

• Cut >$4M in annual overhead.
• Exited two non-core agencies (8020 & Frosty).

Strategic Acquisitions

• Three tuck-in deals completed: Repeat, MediaNet, WholesalePet.
• Booming organic deal pipeline continues to provide growth opportunities.

Looking Forward

With a stronger balance sheet, optimized operations, and strategic acquisitions integrated, Tiny has positioned itself for continued growth and value creation.

The combination of recurring revenue growth, debt reduction, and operational efficiency gains demonstrates the company's commitment to building sustainable, long-term value.

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.

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.

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  Tiny

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  Andrew Wilkinson and I built Tiny together. There’s a lot online about the company, but…

Being recognized for our work at Tiny, which has grown to own over 40 businesses including Letterboxd and AeroPress, is truly humbling.

Here are a few highlights from the article, but I highly recommend reading the full story here.

The Recognition

“We are pleased to recognize Andrew Wilkinson and Chris Sparling as our 2025 DEYA recipients. They have created many opportunities for businesses to grow and thrive.”

Our Entrepreneurial Journey

Our partnership began at MetaLab in 2009.

“We started everything from productivity apps to skincare brands. Some worked, many didn’t. But each failure taught us something valuable about capital allocation.”

Building Tiny

“We realized we were doing it all wrong. Instead of starting new businesses from scratch, we could apply Berkshire Hathaway’s model to internet businesses.”

“Most companies get worse after acquisition. We built Tiny to be different—we buy profitable businesses and stay out of their way.”

Community Impact

“Andrew and Chris represent a new model of entrepreneurship. They’ve shown you can build a world-class company from Victoria.”

The award ceremony will take place on June 10 at the Victoria Conference Centre.

That’s not just bad luck – it’s physics at work. Scientists call it ENTROPY: everything naturally moves from order to chaos unless you actively prevent it.

Learn more about our holding company and our journey building it.

Related: the power of stories in business.

How Disorder Creeps into Business

I’ve seen this play out in companies time and time again. Just like that neglected garden, businesses will naturally slide into disorder if left unchecked:

• Teams start missing deadlines and miscommunicating
• Processes that used to work smoothly become clogged with bottlenecks
• Customer relationships that were once solid start showing cracks
• Simple tasks somehow become complicated multi-step ordeals

New Companies Face the Same Problem

Young startups might think they’re different. Sure, they start out lean and nimble, like fresh saplings in spring. But as they grow, entropy kicks in hard:

• Communication gets tangled
• Decision-making slows down
• Inefficiencies pop up everywhere
• Simple processes become unnecessarily complex

The Price of Not Taking Action

Here’s what really matters: you can’t afford to get comfortable. Companies that aren’t actively fighting entropy are already losing to it. You need new energy, fresh ideas, and better processes just to stay in place.

Understanding Large Company Slowdown

Ever wonder why large companies seem buried in bureaucracy? Now you know – they’re desperately trying to fight entropy. The bigger and more complex they get, the harder they have to work just to maintain order.

What Makes a Successful Company

Want to spot a winning company? Look for ones that are serious about fighting entropy:

• They reinvest in efficiency improvements
• Their leadership actively removes obstacles
• They regularly update and streamline their systems

Taking Action

There’s no escaping it – entropy will always try to push your business toward chaos. The only question is: what are you going to do about it?

Here’s what he believed in:

Learn more about the company we built and our journey building it.

Health and Lifestyle

1. Exercise daily for 30 minutes to 2 hours, with more on Saturdays. Take one rest day every two months. Keep body fat under 10%.
2. Don’t be afraid of eating junk food but eat lots of fruit as well. It you choose to eat fat-free yoghurt, make sure you complement this with plenty of hot-dogs, hamburgers and French fries.
3. Sleep a lot.
4. Drink alcohol two days a week; once in a while to excess.
5. Cigarettes are bad. Cigars after a meal are good.
6. Once a year run a marathon. Once a year do something that scares the shit out of you: a bungie jump, the Cresta run, white-water rafting.

Personal Growth

1. Read even more.
2. Stay curious and never stop learning.
3. Laugh a lot but be reflective.
4. Strive for balance through contradictions.

Living Fully

1. Be a warrior. Be a priest. Be a monk. Be a hedonist.
2. Reason and passion go together but not reason before passion.
3. Switch between daydreaming and sharp awareness. Do reality checks and focus on details.
4. Think positive thoughts even when lying to yourself – your brain won’t know the difference.
5. Seek balance through harmonizing the different aspects of life: physical, spiritual, emotional, sexual.

Wisdom and Philosophy

1. The physical world is an illusion but deal with it as if it were real. At every moment in all societies contradictions are developing and these inevitably lead to discontinuities. In his book “Beyond the Mexique Bay,” Aldous Huxley wrote, “Life is a series of routines punctuated by orgies.” It is and it should be, and neither Huxley nor I mean it in the purely conventional sense.
2. The Roman stoic philosopher Seneca said a lot of useful things.

“Happiness is balance; to teach is also to learn; knowing is better than remembering; we are born unequal, we die equal; to govern is to serve, not to rule.”

Living with Contradictions

1. Be passionate without becoming zealous.
2. Balance political correctness with being down-to-earth. Look to Bill Clinton’s style – wear simple clothes, embrace some pain, but enjoy luxury too.
3. Own a house and enjoy hotel rooms.
4. Travel to extremes, but make each stop feel like home.
5. Seek high awareness and enjoy those brain moments.
6. Be responsible while remembering true freedom means no obligations.
7. Stand by principles but stay flexible and fair.
8. Be optimistic or pessimistic, but always realistic.

Final Wisdom

1. Seek order, face chaos, then step back.
2. Be open, keeping just a few dark secrets.
3. Think like both a historian and prophet.
4. Use both deductive and inductive thinking.
5. Remember – the stock market is usually wrong, but occasionally right.

I found these tips fascinating because they’re not about perfection – they’re about balance. Cundill clearly believed in embracing life’s contradictions rather than fighting them.

And that last bit about the stock market? Coming from a successful investor, it’s pretty telling.

Guy and I first crossed paths during one of my more challenging investment experiences, the Horsehead Holdings equity committee. Despite that rocky start, we’ve stayed connected over the years through our shared interest in value investing and long-term thinking.

Learn more about the company we built and our journey building it.

For my talk, I decided to share a personal story about meeting Charlie Munger and what happened when we tried to help him with Daily Journal’s succession problem.

Video

Watch the full talk on YouTube.

Or watch below:

The Beginning

The story starts in the summer of 2014. Andrew and I were waiting for a seaplane, scheming a plan to pivot from being serial entrepreneurs to becoming investors. Our goal was audacious: to create the Berkshire Hathaway of the internet.

As we sat waiting, we decided we needed another goal. One day, we wanted to meet our idol, Charlie Munger. It’s hard to underscore how unrealistic this seemed at the time. We were just two island bumpkins from Victoria, BC.

Meeting Mr. Luck

I’m a big believer in a simple idea: somewhere out there, there’s a person with the name tag “Luck” on their chest. The probability of running into Mr. Luck goes up if you’re leaving your house, if you’re not just sitting at home. Your odds go up further if you’re traveling, going for business, or attending conferences.

And that’s exactly what happened for us. By pure serendipity, we crossed paths with someone I’ll call Mr. Luck at a conference. This run-in blossomed into a friendship and partnership, leading us to co-invest together.

As our friendship with Mr. Luck grew over the years, he became very well acquainted with our admiration for Charlie. We had animated Charlie’s psychology of human misjudgment speech, and we even sell bronze busts of Warren and Charlie. Mr. Luck saw all of this.

Then one day, out of the blue, Mr. Luck approached us with unexpected news.

The magic of conferences and chance encounters is something I explore in The Power of Being Seen.

Charlie’s Problem

He said Charlie had a problem. Charlie was nearing 97, still at the helm of Daily Journal, with 83-year-old Jerry Salzman still managing as CEO. They had no real succession plan in sight.

Mr. Luck said he could organize a dinner where we could meet Charlie and maybe help with this problem. Our excitement was immense. I literally could have jumped through the roof.

Inside Charlie’s Library

Naturally, we dropped everything and flew to LA. The prospect of meeting Charlie charged every bone in my body. Those nerves continued as we arrived at Charlie’s house. His actual house.

I’ll never forget walking up to the doorbell. We were expecting stern security guards, but instead we were met by Oscar, Charlie’s warm and friendly helper, who eased our anxieties immediately. He told us Charlie was awaiting us inside his library, his sanctuary of wisdom.

We quickly discovered that Charlie isn’t one to ask questions. Instead, he sits back and waits for you to ask him. So we dove right in, peppering him with everything: incentives, raising kids, life regrets, the pitfalls of inheritance, Alibaba, the political climate in the seventies. I even asked him where he got his shirt.

His answer was L.L. Bean. No joke, as soon as I got back to Victoria, I went to the L.L. Bean store and bought a bunch of them.

When the time came to leave, Andrew and I did a Top Gun-inspired high five right there on Charlie’s driveway. We were over the moon. We had done it. We had met Charlie Munger.

The Negotiation

But Charlie’s problem remained. We went back to Victoria and decided to write him a letter explaining our story, how Andrew and I met, the influence Berkshire had on us, and our ideas for the future.

Soon we found ourselves in Charlie’s presence again, but this time there was a new depth to the conversation. Charlie was fully engaged, weaving aspects from our letter into his responses.

We told Charlie we were eager to help, but we’re not managers for hire. By this point, we owned about 30 to 40 businesses. For us to commit, we’d need to be meaningful owners in Daily Journal. The only way that could happen was if we merged.

Charlie was totally unfazed. He actually said he liked it. This kicked off negotiations with Charlie Munger. Words I still can’t believe I can say.

Charlie led with trust. He emphasized trust over profit, saying “I don’t need the last dollar on this.” When lawyers suggested professional valuations, Charlie retorted that we’d find drunkards to rubber stamp everything.

By late 2021, auditors and lawyers were everywhere. We were full steam ahead with this complex merger, all in the name of helping Charlie.

But were we really helping him?

A Moment of Reflection

Back in Victoria, our egos were getting insufferable. We were musing every day that Forbes might call us “mini Mungers.” I can’t imagine what our friends thought of us.

We were telling Charlie that this time-consuming and costly merger was the only solution. But it wasn’t really. We weren’t actually helping Charlie. We were helping ourselves become successors to our idol.

It took a hard moment of reflection for both Andrew and me to own up to this. I’ll never forget the phone call when I called Andrew and we admitted we were going about this the wrong way. Saying it felt like releasing a breath I didn’t know I was holding.

The Right Solution

On that call, we agreed: if we wanted to really help Charlie, we should just offer him what we were actually planning to do. We weren’t going to run the Daily Journal business ourselves. We hire people to run businesses. So we should just bring in our friend Steven and tell Charlie about him.

We sent Charlie another letter calling the whole thing off. True to form, Charlie was very understanding. Never any guilt or stress. We then asked if we could meet again and bring Steven.

By now, we’d learned that Charlie’s love language was reading. So we encouraged Steven to write a letter of his own. The dinner we all had together sealed the deal. Charlie immediately saw what we had seen in Steven and offered to make him CEO and Chairman on the spot.

This journey of meeting Charlie, negotiating with him, and realizing our own poor intent is a chapter I’ll never forget. His approach, favoring simplicity and trust, has profoundly influenced me. I’m grateful to Charlie more than words can ever express.

I've shared more about our journey building Tiny on the HoldCo Builders podcast.

Transcript

Here’s the full transcript from my talk. You can also watch the video on YouTube.

Guy Spier: The next guest is somebody that I met in one of my worst investment experiences, we were both on the equity committee for Horsehead Holdings. But I think that Chris and his partner have been playing long-term games for a very long time, and some of the extraordinary things that you’re probably going to hear about are the result of them living in Victoria, the very west of Canada, and waking up every day and playing long-term games, I guess. But I can vouch for Chris in so many different ways, and I just have to take this moment to say that I can’t vouch for Chris and his coffee taste. Anyway, it’s a whole story.

Chris Sparling: He’s admitting he has terrible coffee taste. All right. Hello my friends. It’s good to be here. I’m actually incredibly excited and I really appreciate Guy for inviting me. I’m just going to try and tell a story. And this story starts in the summer of 2014. I was waiting for a seaplane with my business partner, Andrew, and we were scheming a plan. We were going to pivot from being serial entrepreneurs, starting as many businesses as we possibly could, to becoming investors. And our goal was to create the Berkshire Hathaway of the internet.

As we sat waiting for the seaplane, we tossed around names for this new company and we decided we needed a goal, an audacious goal. We wanted to one day meet our idol, Charlie Munger. It’s hard to underscore how unrealistic this goal seemed at the time. As Guy said, we’re two island bumpkins from Victoria BC and really, I think what we had, I kind of think no right to believe that this was possible. But I’m a big believer in a simple idea, and that is, somewhere out there, there’s a person with the name tag “Luck” on their chest.

And the probability of running into Mr. Luck goes up if you’re leaving your house, if you’re just not sitting at home. And your odds of luck or running into Mr. Luck goes up further if you’re traveling, if you’re going for business or you’re going to conferences. And that’s exactly what happened for us. By pure serendipity, we crossed paths with someone I’m going to call Mr. Luck. And this was at a conference. This run-in with Mr. Luck blossomed into a friendship and a partnership leading us to co-invest together. And as our friendship with Mr. Luck grew over the years, he became very well acquainted with our admiration for Charlie. We shared everything. We had a pet project where we animated Charlie’s psychology of human misjudgment speech, and we also have a side fun venture where we sell bronze busts of Warren and Charlie. And so, Mr. Luck saw this the whole time, and then one day out of the blue, Mr. Luck approached us with very unexpected news.

He said Charlie had a problem and Mr. Luck said that he could organize a dinner where we could meet him and maybe we could help him with this problem. Our excitement was more immense than you can imagine. I literally could have jumped through the roof. Charlie’s problem was this, it was Daily Journal. He was nearing 97 and he was still at the helm and 83-year-old Jerry Salzman was still managing as CEO and they had no real succession plan in sight. Naturally, we dropped everything, and we flew to LA. The prospect of meeting Charlie charged every bone in my body. Those nerves continued as we arrived at Charlie’s house, his actual house. I’ll never forget walking up to the doorbell and we rang the doorbell, and we were expecting like stern security guards, but instead we were met by this warm, friendly face Oscar who Charlie’s helper, and he helped ease our anxieties immediately.

He told us Charlie was awaiting us inside his library, his sanctuary of wisdom. It didn’t take us long to discover that Charlie isn’t really one to ask questions. Instead, he sits back and waits for you to ask him questions. And so, we dove right in. We peppered him with everything you could possibly think of both to fill the silence and to gleam. We asked him about incentives, raising kids, life regrets, the pitfalls of inheritance, Alibaba, the political climate in the seventies. I even asked him where he got his shirt, and his answer was L.L. Bean. And it’s this one right here. No joke, as soon as I got back to Victoria, I went to the L.L. Bean store, and I bought a bunch of them. We asked him everything you can imagine. Eventually the time came for us to leave, and I kid you not outside of Charlie’s house right there on his driveway, Andrew and I did a top gun spot inspired high five. We jumped into the high five. We were over the moon. It was a moment of peer unabashed triumph. We had done it; we had met Charlie Munger.

But Charlie’s problem had remained. We did ask about Daily Journal, but it was unclear how we’d still help. So, we went back to Victoria with this problem on our mind. We were unsure how to really proceed, and so we decided to write Charlie a letter. In this, we told him our story, how Andrew and I met, the influence Berkshire had had on us, and a few different ideas on what we saw as the future of us and them. Soon we found ourselves in Charlie’s presence again. This meeting felt both familiar and strikingly different. Oscar, the ever-friendly face greeted us at the door, and we found ourselves once again sitting in Charlie’s living room and dining room, peppering him with questions. But this time there was a new depth to the conversation. Charlie was fully engaged. His responses reflecting a thorough understanding of who we were. It was really cool. We asked him questions, but now he recalled aspects from our letter, and he weaved them into his story or into his answers with us.

We told Charlie we were eager to help, confident that we can make a significant difference, but we’re not managers for hire. By this point, my partner and I owned about 30 to 40 businesses. And for us to commit, we’d have to be meaningful owners in the Daily Journal. And the only way that could really happen is if we merged. We thought this was being a bit of a bold idea, but Charlie was totally unfazed. He actually said he liked it. And this kicked off the negotiation with Charlie Munger, which are words I still cannot believe I can say. Charlie led with trust. He opened up the kimono immediately on the Daily Journal and we worried that Charlie, who was nearing a hundred, wouldn’t understand our software businesses. So, we tried writing many letters explaining each one of these businesses, how we got the capital for each one and how it all worked.

And Charlie instinctively knew what mattered and how to cut complexity. So, he just simply called us and said, “Don’t worry about each business. Tell me about the two to three important ones and things that you’re excited about.” And so, we did, and our straightforward discussion extended to valuations where Charlie emphasized trust over profit. He’d say, “I don’t need the last dollar on this.” At every juncture Charlie kept it simple and flowing. When lawyers suggested professional valuations, Charlie retorted saying that we’d find drunkards to rubber stamp everything. By late 2021, auditors and lawyers were everywhere, and we were full steam ahead with this complex merger all in the name of helping Charlie. But were we really helping him?

Back in Victoria, our egos were getting insufferable. They were really swelling. We were amusing every day that Forbes might call us mini Mungers. I can’t imagine how our friends thought about us, like we were truly insufferable. We were telling Charlie that this time consuming and very costly merger was the only solution, but it wasn’t really. We weren’t actually helping Charlie; we were helping ourselves to become successors to our idol. And it took this really hard moment of reflection for both Andrew and I to own up to this, and I’ll never forget the phone call when I called Andrew and we just admitted that we’re going about this the wrong way. Saying this felt like I was releasing a breath I didn’t know I was holding. On that call we agreed that if we wanted to help Charlie and I mean really help Charlie, then we should just offer him what we were actually planning to do. When we actually took over, we weren’t going to actually run the Daily business, we hire people to run these businesses. And so, we said we should just bring in our friend Steven and tell Charlie about him.

So, we sent Charlie another letter suggesting the whole thing off, and true to Charlie’s form, he was very understanding. He never went about anything with guilt or any kind of stressful tone. It was such a pleasure. We then asked Charlie if we can meet and bring our friend Steven. By now, if you can’t tell, we thought Charlie’s love language was reading because it’s hard to really convey your story with him in person. And so, we encouraged Steven to write a letter of his own. And the dinner that we all had together sealed the deal. Charlie immediately saw what we had seen in Steven and offered to make him the CEO and Chairman on the spot. Obviously, it took a bit more time, but Charlie leaps quick. This journey of meeting Charlie, negotiating with him and realizing our own poor intent, it’s a chapter in my life I don’t think I’ll ever forget. His approach favoring simplicity, trust has profoundly influenced me. I’m grateful to Charlie more than words can ever express. Thanks.

Guy Spier: I’m hugging you on behalf everyone. So, we’re trying to catch up on time that we lost, but we could spend a whole afternoon with Chris asking him questions. And just for everybody to know, part of why I think this format works is that we allocate the 10 minutes to everyone, and it means that there’s something for everyone. So, I would’ve loved to have done a three-hour deep dive here. It would’ve been fascinating. But I want to get a couple of questions from everyone else. I have my own, but if you want to ask a question, go to the mic I think is the best way to do it. And let’s say we’ll do two because we’re going to try and catch up as well. But that was beautifully written.

Chris Sparling: I literally wrote it on the flight over yesterday and I timed it out yesterday and I was at 12 minutes, and I practiced again just before this, and I was at eight. And I was thinking I’ll probably be about three minutes as I’ll actually be on stage and run through it.

Guy Spier: But there’s also, do you feel Victoria coming through? There’s this quiet calmness to Chris and he’s properly dressed whereas I’m really badly dressed. But two questions, Aiden and then Matthew, and then we’ll move on to Robert Hagstrom. Go ahead Aiden.

Audience Member (Aiden): Thank you. So, this might be a very easy one. Firstly, thanks for teaching us about the importance of proactive serendipity, but second, can you truly be a value investor if you don’t make your coffee using AeroPress?

Chris Sparling: I wholeheartedly agree.

Audience Member (Aiden): Thank you.

Chris Sparling: A coffee that tastes like the coffee bean smells.

Guy Spier: Thank you, Aiden. Matthew, just let me explain to the audience here. So, one of the companies that Chris acquired is called AeroPress and I actually have one, and if you’re traveling somewhere far away from Italy and you don’t have access to good coffee, you can probably make a decent coffee out of it. But Chris and I have a fundamental disagreement on what makes a great coffee and Aiden was trying to scratch that and it’s a subject that will go on for a very long time. But go ahead, Matthew Peterson.

Audience Member (Matthew Peterson): Chris, thank you so much. Thank you, Guy. I’m curious, I understand Andrew’s going to publish a book and I know you’re very involved and I’m curious if you could maybe give us a little bit of insight in what might come out of that. Or if you have any thoughts on what we’re seeing on the 13Fs of Daily Journal or if you have anything you can share with the group. Because there’s a few things that are changing now that Steven’s involved that I know you kind of have some information.

Chris Sparling: I do. I’m not able to weigh in on Daily Journal just for a variety of different reasons. I would say I’m more excited about the direction of Daily Journal though than ever before and I really do believe and have high conviction in Steven. He’s an incredible individual, very successful entrepreneur and he has a great grasp on what would need to be true in order to make that a competing business with Tyler. In terms of the book, it’s kind of this, it’s Andrew and I’s story as well, and it’s the realization of, I’d say the mistake of putting certain things on a pedestal and believing achievement of those things will lead to happiness and trying to upend that and his personal journey to that realization.

Audience Member (Matthew Peterson): Beautiful. Thank you, Chris. I appreciate it.

Guy Spier: Every time I spend time with Chris, I wish I spent more time with him because I think that just spending time around him you learn a better way to be in the world. And it’s just interesting that you came after Luca because I really do believe that what you and Andrew have been doing is playing long-term games. And suddenly you get this explosion of results 20 years into it and it’s really fun to watch. So, thank you for coming. Thank you for doing this.

Chris Sparling: Thanks for having me.

The bartender was moving like lightning, and a crowd had formed at the counter, everyone fighting for attention.

The Invisible Customer

At first, I just stood there, feeling completely invisible. The feeling of being unseen in a crowded space is something I hadn’t experienced quite so intensely before.

Related: the value of personal stories.

I started doing this awkward dance that probably looked ridiculous – bobbing my head around, half-raising my arm, trying anything to catch the bartender’s attention.

The Silent Struggle

It felt like I was screaming without making a sound. Each failed attempt to get noticed just ramped up my anxiety. In a space packed with people, I’d never felt more alone.

The Moment of Recognition

Then everything changed with a single look. The bartender caught my eye and gave me that universal quick nod that means “I see you, I got you.” That simple gesture cut through all the noise and chaos like nothing else could.

The Impact

That moment of recognition hit me differently than I expected. It wasn’t just about getting my drink anymore – it was about existing again in that packed space. It’s amazing how such a small acknowledgment can completely change how you feel in a crowded room.

The Lesson

The experience taught me something I won’t forget. When everyone’s just trying to be seen in the chaos, a moment of recognition can be a game-changer. Since then, I’ve tried to be more aware of others who might be feeling invisible in crowded spaces. Sometimes all it takes is a simple nod to let someone know they exist.

Final Thoughts

It’s crazy how such a small thing – being acknowledged in a crowded bar – could make such a big difference. But that’s exactly what happened, and I’m glad I experienced it.

While I wasn’t a guest on the show, Shaan shared some interesting observations about me following our recent meeting at an event in Vancouver.

Learn more about our holding company and our journey building it.

Related: HoldCo Builders podcast appearance.

Video

Watch the podcast on YouTube by clicking here.

Or watch below (start at 15:08):

Video: This Guy Is Richer Than Jeff Bezos & Elon Musk… (#425)

The Backstory

Shaan Puri and I met for the first time at a dinner event in Vancouver.

Despite having worked with Andrew Wilkinson for years, Shaan and I had never crossed paths until then.

During our conversation, Shaan noticed some similarities in how we both think and approach problems.

What Shaan Had to Say

Shaan described me as someone who “had the juice” – a rare quality he found surprising given my somewhat reserved nature.

He observed that while I might prefer to be at home reading a book, I was able to engage deeply in conversation once the “switch was flipped.”

“I think he would have rather just been at home reading a book. But he had this thing which is like, I’m at this dinner. So the flip is the switch is flipped.”

The Framework Guy

One of the most notable things Shaan picked up on was my tendency to use mental models and frameworks in conversation.

Sam Parr agreed with this observation, mentioning that this was one of the key similarities between Shaan and myself.

“He was like, Mr. Framework… He’d be like, it’s like the Streisand effect mixed with the thing that, you know, like, you know, the sucker’s bias.” – Shaan Puri

Learning the Right Lessons

Perhaps the most impactful moment Shaan shared was about a question I asked at the dinner that has stuck with him since.

When someone was telling a story about business lessons learned, I apparently asked:

“Do you think that’s the right lesson to learn out of that?”

Shaan found this question profound, noting that it’s a critical indicator of success – whether people are actually taking away the correct lessons from their experiences.

He mentioned that since our dinner, he’s been seeing this concept everywhere in his life.

The Origin Story

Sam also shared a bit about my backstory with Andrew Wilkinson.

Andrew met me when I was working at a bank (not as an investment banker, but as Shaan put it, a “go to the bank, I need to write a check banker”). We connected over a shared interest in cars.

The story goes that on my first day working with Andrew, I showed up to find him absent, being handed a box of financial papers, and told to set up at a desk in a neighbor’s basement!

The Buffett Connection

Sam mentioned that Andrew and I were influenced by Warren Buffett’s biography (likely “Snowball”) and Charlie Munger’s approach to business and mental models.

This shaped our approach to building Tiny, which follows a similar philosophy to Berkshire Hathaway, but focused on internet companies.

Conclusion

It was fascinating to hear how I was perceived by these successful entrepreneurs and podcasters.

The mental models and frameworks approach that Shaan highlighted is indeed central to how I think about business problems. And the question about “learning the right lessons” is something I believe is crucial for anyone looking to grow from their experiences.

I’m grateful for the thoughtful discussion and look forward to continuing conversations with the MFM community.