The biggest lesson from a $30M loss

What if losing millions was the best thing that could’ve happened to you? That’s how Mike Dillard sees his early Bitcoin loss – and it’s shaped everything since.

He bought his first Bitcoin in 2013, wiring $30,000 to the now-defunct Mt. Gox exchange and receiving around 340-350 BTC in return. But amid a turbulent period that included a divorce and major business fraud, Dillard stepped away. When he returned, Mt. Gox had collapsed – and so had his investment.

Speaking to The Crypto Radio, Dillard shared unfiltered insights into the world of digital assets, revealing a pragmatic approach that cuts through the hype and speculation.

More than a decade later, he’s still in the space – not as a Bitcoin maximalist or crypto cheerleader, but as someone who’s taken big risks, made painful mistakes, and stayed curious enough to keep learning. He doesn’t sell dreams or promise instant riches. Instead, he views cryptocurrency as a learning experience, emphasizing that "this is all just a game designed to teach us something."

Understanding cryptocurrency for beginners

For those new to digital currency, Dillard breaks down the landscape into three primary investor types: risk-takers, entrepreneurs, and tech-savvy early adopters. "What has drawn people in is greed," he said bluntly. "It's the chance to make a lot of money."

It’s a refreshingly honest take in an industry often dominated by hype and hustle culture. However, Dillard was quick to draw a line between investing and gambling. "From an investment perspective, there's only one crypto investment, and that's Bitcoin. Everything else is gambling and speculation."

That conviction is backed by a methodical, no-frills strategy. His advice for newcomers? "Just buy Bitcoin and average in every week for the next 10 years." In an era of quick flips and memecoin manias, Dillard’s long-term perspective stands out. It’s not about timing the market – it’s about time in the market.

For those overwhelmed by the sheer number of tokens, chains, and protocols, his message offers welcome clarity: focus on the fundamentals, ignore the noise, and avoid the temptation of easy money.

Digital security and smart practices

Photo: Unsplash / Towfiqu Barbhuiya

Beyond what to buy, Dillard is adamant about how to hold it. One critical aspect he emphasizes is digital security. He recommends using encrypted password management tools like 1Password and tracking investments through apps like CoinStats. "I don't know how people would manage their crypto wallets and passwords without that," he said.

It's a point often overlooked by newcomers who may prioritize quick profits over long-term safety. But Dillard knows from experience that losing access – whether through hacks, lost passwords, or misplaced keys – is a far more common risk than market volatility.

For those intimidated by complex technology, he suggests sticking to mainstream exchanges like Kraken and avoiding advanced decentralized platforms that increase potential risks. “If it’s hard to use,” he implied, “you’re probably not ready to use it yet.”

Market predictions and personal philosophy

While many crypto influencers flood social media with bold predictions and moonshot charts, Dillard offers a more measured outlook. He anticipates potential economic turbulence ahead – and with it, the possibility of significant moves in Bitcoin’s price. "If the government drops interest rates to zero and turns on the money printer, Bitcoin could go to $300,000," he explained.

But even then, he tempers expectations. This isn’t about getting rich. It’s about protecting wealth – and peace of mind.

"None of this really matters at the end of the day," he said. "I'm just trying to create a comfortable final chapter of life in my 50s, 60s, 70s, or 80s."

It’s not the kind of line you hear often in crypto circles, but it underscores the theme that runs through Dillard’s story: this is a long game, and personal well-being matters just as much as financial gain.

Lessons from failure

Looking back, Dillard said the most important lesson was learning not to beat himself up over mistakes. "We can't blame ourselves for decisions made in a moment with limited information," he advises.

That self-compassion is rare in an industry often defined by bravado and relentless self-promotion. But for Dillard, failure wasn’t the end – it was the foundation for something more sustainable.

Rather than retreating after his loss, he stayed in the game, refining his strategy and shifting his mindset. For those coming into crypto now, he wants them to benefit from the scars he’s already earned.

Emerging technologies and skepticism

When it comes to emerging technologies like AI and blockchain, Dillard remains skeptical. He’s not opposed to innovation – but he’s wary of buzzwords used to mask weak ideas. "99% of things don't need to be on a blockchain," he argued.

Instead, he sees potential in just a few focused areas, including financial asset tokenization and in-game asset trading. The rest, in his view, is mostly noise.

That selective interest speaks to his larger philosophy: stay grounded, stay cautious, and don’t get swept up in every new trend. For Dillard, critical thinking is more valuable than technical know-how.

A balanced perspective

As he describes himself, he's like "a grumpy tour guide who's been in the jungle and survived a few times" – offering wisdom earned through hard-won experience.

For anyone thinking of stepping into crypto, Dillard’s approach is a valuable counterpoint to the noise: understand the technology, manage your risks, and never invest more than you can afford to lose.

His final piece of advice? Stay curious, remain skeptical, and always continue learning.

Listen to the whole interview on The Crypto Radio's live player or the Chain Breakers podcast.