Dmytro Karpilovskyi: On Enduring Losses, Rebuilding with Clarity, and Investing with a Steady Mind

April 27, 2025, marked the N Crypto Conference in Kyiv—a cornerstone gathering for Ukraine’s growing community of investors and crypto thinkers. Among the keynote speakers was Dmytro Karpilovskyi, a seasoned finance expert with more than two decades of experience and the founder of UkrInvestClub, the country’s largest investor collective.

Dmytro spoke about the transformation he’s witnessed across the crypto industry. According to him, the market has grown more disciplined, with participants approaching risk more thoughtfully. His return, after years of working in traditional sectors, brought a sense of reconnection to a space that once shaped his early investment path.

Our interview with Dmytro covered:

• how his investment strategy has adapted in response to changing markets,
• the lessons learned from risk management and financial loss,
• and his perspective on crypto’s long-term relevance in global finance.

From Speculative Growth to Conservative Structuring: Tracing Karpilovskyi’s Investment Portfolio Shift

At the outset of his investing career, Dmytro Karpilovskyi gravitated toward maximum-risk positions—targeting early-stage ventures, digital assets, and volatile sectors. His portfolio was built for exponential upside but carried a significant probability of collapse. The approach mirrored the speculative climate of the time, where high failure rates were considered part of the cost structure.

The Coinomist: What’s changed in how you invest now versus when you started? Do you assess risk differently today?

Dmytro Karpilovskyi: Absolutely. I’ve intentionally lowered my average risk. Early on, I was fully invested in high-risk assets. Today, my portfolio leans heavily toward real estate. These ventures still carry risk, but the likelihood of major disappointment is substantially reduced.

Today, Dmytro’s portfolio is anchored in real-world assets:

• commercial real estate,
• logistics warehouses,
• vehicle fleets.

While some of the investments are tokenized, they’re all backed by physical holdings. He’s also reduced the breadth of diversification—choosing to concentrate capital into fewer, high-conviction positions that offer tighter operational control.

How to Build an Investment Strategy in 2025: Insights from Dmytro Karpilovskyi

Though he refrained from offering direct investment recommendations, Dmytro outlined a framework for building a portfolio that adapts to available capital. Rather than spotlighting crypto, he emphasized the structures that anchor his own strategy today—highlighting risk-adjusted positioning over speculative swings.

The Coinomist: What’s your approach to portfolio allocation at capital levels of $10K, $50K, or $100K? Which sectors are currently part of your strategic focus?

Dmytro Karpilovskyi: I’m not actively involved in the crypto space at the moment, so I’ll leave that aside. My main allocation focus is energy—particularly the Ukrainian energy sector, which I view as a clear leader. I’m also exploring collective investment models in real estate, including tokenized assets, cooperatives, and DAO LLCs—any format that makes sense legally. And military-tech is a big one too. I think there’s a potential there.

Dmytro notes that the most attractive investment opportunities today are often hidden in segments where rapid orientation is difficult—markets defined by structural demand-supply imbalance. A deep dive into such ecosystems reveals overlooked entry points that remain off the radar for typical investors.

“Avoiding Investment Is the Real Risk”: Dmytro Karpilovskyi on the Investor's Mindset

Losses are just part of the game. Dmytro Karpilovskyi doesn’t sugarcoat it—he’s had moments where a big hit made him wonder if he should quit investing altogether. But in his view, the real danger lies in staying out of the game completely.

The Coinomist: After big losses, did you ever feel like giving up?

Dmytro Karpilovskyi: Of course. Whenever you lose a lot of money, you go through that moment: “Why bother? I’m never doing this again.” But that’s just emotion talking. The truth is, the biggest risk isn’t a bad trade—it’s not investing at all and watching inflation chip away at your savings year after year.

Dmytro views financial loss as a multidimensional stress test—affecting both capital and emotional discipline. He emphasizes the importance of delaying decisions during heightened emotional states. After a structured review, losses are reframed not as failure, but as the educational price of staying in the game and improving over time.

For Dmytro, investing is no longer solely a vehicle for financial returns. It has become an enduring intellectual framework—an ongoing journey of discovery and strategic growth. Though financially independent, he continues to pursue new ventures. The complexity of managing risk across varied markets is what sustains his drive.

Recovery from setbacks, he notes, is not about raw determination. It reflects a more profound psychological alignment: viewing risk not as failure, but as a necessary and accepted cost of participation.

Emotional Volatility in Investing: Developing Rational Responses to Loss

Emotional durability is a critical component of investor performance. Dmytro Karpilovskyi emphasizes that losses are structurally inherent to the process—not deviations from it. The central skill lies in building a mindset that treats loss as data, not drama.

The Coinomist: How do you cope with emotional strain following financial losses? What helps restore balance?

Dmytro Karpilovskyi: There’s no definitive solution, but time plays a crucial role. Emotional reactions diminish, making space for rational assessment. The priority is to identify whether the loss stemmed from an error or a calculated decision. If it was a mistake, I note it and ensure it doesn’t recur. But if the risk was intentional and the outcome unfavorable, then that’s just part of being in the investor’s game.

Dmytro cautions against interpreting investment losses through the lens of personal fault or external conspiracy. “Investing is compensated risk-taking,” he explains. “We earn returns precisely because we agree to operate within uncertainty.”

His stabilizing framework is clear: differentiate between operational mistakes and systemic market variability. A loss that yields a functional insight is a net gain. But treating volatility as failure risks psychological fatigue and undermines decision-making resilience.

Investing isn’t just one big winning streak. It’s rooted in self-awareness—the capacity to engage with risk intentionally and maintain perspective when faced with inevitable losses.

Flawed by Nature: The Classic Mistakes Investors Keep Repeating

No investor is perfect—and experience shows that early missteps usually don’t come from choosing the wrong asset, but from misjudging risk, misunderstanding liquidity, or skipping the planning stage altogether. Dmytro Karpilovskyi offers his perspective on the most common investment pitfalls he’s encountered over the years.

When asked to identify both his own investing missteps and those he frequently observes in others, Dmytro offered this:

My mistake was an overreliance on high-risk assets—I stuck with them longer than I should have. It took time for me to develop a disciplined approach to conservative instruments. A second, broader issue is that many investors lack contingency strategies. Too often, the entire plan is: buy low, sell high. And when the market doesn’t cooperate, there’s no alternative course of action.

One thing Dmytro sees all the time? People ignoring liquidity. They get excited about how much an asset could grow—but don’t ask what happens if they can’t sell it. Some assets just freeze. Forever.

Another red flag? Getting too confident in your favorite trend. “People start thinking certain things are invincible,” he says. Just because something’s done well before doesn’t mean it will again. In Dmytro’s view, even Bitcoin is subject to market law—no asset is universally reliable.

Sound investing demands restraint. Emotional attachment to assets—especially those with visually compelling price trajectories—can distort judgment. What should guide decisions is a framework rooted in logic, analytical rigor, and critical reasoning.

“At the moment, I hold zero Bitcoin”: Dmytro Karpilovskyi on Crypto’s Role in the Broader Financial Landscape

Asked whether cryptocurrencies might eventually supplant the global financial order, Dmytro remains pragmatic. His outlook avoids utopian narratives in favor of structural realism.

The Coinomist: Do you think crypto or blockchain projects could ever replace traditional finance entirely?

Dmytro Karpilovskyi: I don’t think they’ll take over the whole system. But I’m pretty confident crypto assets will grab a serious slice of the financial market in the years ahead.

Dmytro acknowledges that while the crypto industry will continue to develop, its market structure will remain fluid.

He believes we’ll see multiple shakeups in the market cap leaderboard of top coins:

I’m convinced the top 10 by market cap will change again and again. I don’t place unconditional faith even in Bitcoin. Right now, I hold exactly zero.

Karpilovskyi argues that blockchain technology will lead to the development of next-generation financial instruments, broadening investor access and introducing structural alternatives to incumbent systems. Yet, he emphasizes, this does not imply a full-scale replacement of traditional finance. The trajectory, as he sees it, points to convergence—where both models coexist and gradually influence one another.

Investment as Adaptive Survival: Key Takeaways from Dmytro Karpilovskyi’s Approach

Talking to Dmytro was a wake-up call. Real investing? It’s not about chasing quick profits. It’s about staying in the game—learning discipline, staying flexible, and managing risk like a pro. He’s come a long way from the early days of high-risk plays. Now, it’s all about smart, stable strategies grounded in real-world assets.

Mistakes, emotional volatility, and financial losses are intrinsic to investor development. According to Dmytro, crypto assets will become an integral feature of the global financial ecosystem—but they are unlikely to supplant established models. Integration, not disruption, is the more probable trajectory.