Lately, I’ve found myself drawn to thinkers who value clarity and practicality over noise—people like William Bengen, Paul Merriman, and Jamie Dimon. While their styles differ, each reminds me of a core investing truth:
what matters most isn’t theory, but application.
I recently started following Dimon more closely. His long tenure at JPMorgan and his calm presence in high-stakes environments—such as his recent meetings with former President Trump, covered by
The Wall Street Journal
—show a kind of decision-making that resonates with me. Dimon’s pragmatic approach, long-term focus, and willingness to speak plainly, even when it’s unpopular, are qualities I admire.
Jamie Dimon, JPMorgan CEO, met President Donald Trump at the White House twice over the past two months—a major shift after years of public disagreements. They discussed the economy, trade policy, financial regulations, interest rates, and the administration’s trade deal with Japan. Dimon congratulated Trump on the trade agreement and defended Federal Reserve Chair Jerome Powell’s independence, disagreeing with Trump’s push to lower interest rates. Senior White House officials attended these meetings, which mark a thaw in the previously strained relationship. The two have clashed in the past, but recent talks focused on economic policy and national interests.
(For a detailed account, see the original WSJ article.)
In managing my own portfolio—especially as I navigate Roth conversions—I aim to act with the same level of deliberation. Lately, I’ve started to tilt more toward small-cap value stocks within my Roth accounts. The logic: placing higher-risk, higher-growth assets where tax-free growth can compound over decades. While this introduces more volatility and the risk of periods of underperformance, it’s a long-term bet that I believe aligns with pragmatic investing wisdom.
My approach reflects the practical mindset of experienced leaders: I prioritize real-world application over theory, keep a long-term focus, and make calm, reflective decisions—even when trends shift. By intentionally tilting my Roth toward small-cap value and weighing risk with potential, I aim for strategies that fit my goals—not just what’s popular. It’s about clarity, patience, and staying committed to what actually works for me.
There’s value in listening to seasoned voices and then pausing to reflect: What actually works for me? What end am I working toward? That spirit of reflection and calm action is something I hope FlightToWealth continues to capture—for myself, and for others walking a similar path.