One of the highlights of the trip was the 50th anniversary conference of the Association of Translation Companies (ATC), attended by our CEO at Caulingo. Meanwhile, I took a somewhat different approach to exploring the local economy, spending time shopping at Primark and Deichmann, while occasionally exchanging handshakes with fellow European founders over breakfast.

And, naturally, I couldn’t resist combining travel with investing. I picked up a few fractional shares of IHG (InterContinental Hotels Group), the company behind the hotels we stayed at during our Scottish adventure — Holiday Inn Express in Edinburgh and Voco in Glasgow.

A little sightseeing, a little shopping, a little business networking, and even some stock accumulation along the way.

Stock Market Overview

It has been another mixed week for US stock markets, with renewed selling pressure in technology and AI-related stocks contrasting with relative strength in more traditional sectors.

The biggest pressure came from technology stocks, particularly semiconductors, as investors continued questioning elevated AI valuations and the sustainability of heavy capital spending. Meanwhile, healthcare, consumer staples and financial stocks showed greater resilience.

For our dividend and options portfolio, the environment was relatively manageable. We finished the reporting week with a modest gain, although several outstanding short option positions continued to weigh on overall performance.

The coming week could prove more eventful, with the Federal Reserve’s interest rate decision and quarterly earnings from several major US companies, including Microsoft, Alphabet, Amazon and Bristol Myers Squibb.

Dividend Stock Portfolio Performance

As of October 23, 2026, our options-selling-powered dividend stock portfolio stood at $13,510, marking a weekly increase of 0.40% compared with the previous week.

Year to date, our portfolio is up 34.58%, comfortably outperforming the S&P 500’s reported 11.47% gain over the same period.

Over the past few weeks, our portfolio has remained largely flat, struggling to break through the $14,000 milestone. The main drag on performance has come from two longer-dated put option positions rather than the underlying stock holdings themselves.

Nevertheless, we remain cautiously optimistic about a potential rebound as we approach year-end. Our $15,000 portfolio target remains on the radar, although achieving it would require an exceptionally strong final two months of the year.

Besides purchasing a few fractional shares, we also rolled our weekly BMY put option forward and down for a net credit, lowering our strike price while collecting additional premium.

With Bristol Myers Squibb scheduled to report quarterly earnings on October 29, just one day before our October 30 put expiration, we expect increased volatility in the stock. Hopefully, the earnings reaction will be positive, but we are prepared to manage the position if the market moves against us.

Current Open Options Positions

• BMY OCT 30, 2026: $59 Cash-Secured Put

• BMY NOV 20, 2026: $55/$50 Credit Spread

• NFLX NOV 20, 2026: $85/$105 Bear Call Spread

• BAC DEC 18, 2026: $57.5/$60 Bear Call Spread

• LHA (Frankfurt) DEC 18, 2026: €7 Cash-Secured Put

• BAC MAR 19, 2027: $55 Short Put

• NFLX DEC 17, 2027: $64 Short Put

• NVDA JAN 21, 2028: $130 Covered Call

Our open positions now span several expiration dates, ranging from near-term options to long-dated contracts extending into 2028.

Among our open positions, Lufthansa continues to put pressure on portfolio performance. If the stock fails to rebound, we may consider rolling the €7 cash-secured put forward and down in the coming weeks to reduce our potential assignment price, ideally while collecting additional premium.

We will also pay particular attention to our BMY positions. The October 30 $59 put and November 20 $55/$50 credit spread both carry downside exposure to the same underlying stock, making the upcoming earnings announcement especially relevant.

Our NFLX November bear call spread also deserves monitoring, particularly if technology stocks rebound sharply after recent weakness. Meanwhile, our longer-dated NFLX and BAC short puts remain positions to evaluate in terms of capital requirements, assignment exposure and potential rolling opportunities.

Weekly Options Premium

Our reported options premiums collected during Week 81 reached $54. While below some of our stronger weeks, the income continues to support gradual portfolio accumulation.

Our outstanding margin debt now stands at approximately $2,403, slightly higher than a week ago, partly reflecting additional share purchases.

In theory, if we directed the entire $54 in weekly options premiums toward paying down margin debt, it would take approximately 45 weeks to eliminate the remaining balance.

Of course, this assumes consistent weekly premium collections, no additional borrowing, and no interest expenses or trading losses. Real life is rarely that straightforward.

This week, we added:

• 0.1 share of BMY

• 0.2 share of IHG

• 2 shares of NIO

• 1 share of NU

These small purchases are part of our gradual accumulation strategy. They won’t transform the portfolio overnight, but over time, they should help us build larger positions and potentially open new opportunities for covered call selling.

Bottom Line and What We’re Watching Next Week

Another relatively quiet week for our portfolio, with a 0.40% gain bringing NAV to $13,510. We collected $54 in options premiums, continued accumulating fractional shares and successfully rolled our challenged BMY put to a lower strike for additional credit.

While our underlying stock holdings have generally remained resilient, several outstanding options positions continue to limit overall portfolio progress. As we approach the final two months of 2026, the immediate objective remains to break through $14,000, while keeping our more ambitious $15,000 year-end target in sight.

Next week, our attention will be focused on:

• BMY earnings on October 29: Our most immediate portfolio-specific event. We will monitor the $59 cash-secured put expiring October 30 and the November $55/$50 credit spread. A positive earnings reaction could provide welcome relief, while further weakness might require another adjustment.

• Lufthansa and the €7 put: We will watch for signs of a sustained recovery. If the stock remains under pressure, rolling the December position to a lower strike and later expiration may become an option, depending on pricing and available credit.

• NFLX and BAC options exposure: The November NFLX bear call spread could become more challenging during a technology rebound. We will also monitor our December BAC bear call spread, particularly if financial stocks continue outperforming.

• Federal Reserve and major technology earnings: The October 28 Fed decision, together with Microsoft, Alphabet and Amazon earnings, could influence broader market sentiment and volatility, including the outlook for our technology-related positions.

• Margin and portfolio milestones: At approximately $2,403 in outstanding margin debt, we will continue balancing new stock purchases with options income and risk management. The $14,000 milestone remains our immediate objective.

For now, our strategy remains unchanged: sell options, collect premiums, accumulate quality stocks and manage challenged positions patiently. The market may offer better opportunities toward year-end, but there is no reason to force trades simply to reach a portfolio milestone.

Slow and steady. Another week of building the portfolio, one trade and one fractional share at a time.

This actually came as a bit of a surprise to me, as the underlying stock prices in the portfolio seemed to be moving in the opposite direction. My best guess is that some option prices hadn’t fully settled or updated when I checked the numbers early on Saturday morning. I’ll need to double-check that.

That said, it was another week of ups and downs. The previous week, I switched to selling covered calls on Bristol Myers Squibb (BMY). This week, I decided to let those shares get called away and return to selling puts, effectively continuing the wheel strategy.

Nothing particularly dramatic, just another week of collecting premiums, managing positions, and letting the wheel do its work.

Year to date, our portfolio is up 33.80%, comfortably outperforming the S&P 500’s 11.68% gain over the same period.

After our Bristol Myers Squibb (BMY) covered call expired in the money, I couldn’t find a meaningful opportunity to roll the position forward for another week or two while collecting a decent credit. So, I decided to reset the wheel, let the shares get called away, and re-enter through put selling, hopefully collecting higher premiums along the way. Let’s see if I regret that decision next week!

Additionally, our Bank of America (BAC) bear call spread expired worthless, allowing us to keep the full premium collected. I opened a new bear call spread, this time with a December expiration.

We use bear call spreads on top of our challenged short put positions to squeeze some extra premium out of trades that haven’t exactly gone our way. It’s a way to generate additional income while waiting for the underlying stock to recover.

Of course, this can be a dangerous game. We’re essentially adding another layer of risk to an already challenged position, and a sharp rebound in the stock could quickly turn those extra premiums into losses.

And if you’ve been following my articles hoping to learn a thing or two about options trading, remember: I’m sharing my own experiments, not a trading playbook. Follow along, but trade at your own risk.

Current Open Options Positions

• BMY OCT 23, 2026: $60 Cash-Secured Put

• BMY NOV 20, 2026: $5-wide Rolled Credit Spread, with strikes lowered by $2.50

• NFLX NOV 20, 2026: $85/$105 Bear Call Spread

• BAC DEC 18, 2026: $57.5/$60 Bear Call Spread

• LHA (Frankfurt) DEC 18, 2026: €7 Cash-Secured Put

• BAC MAR 19, 2027: $55 Short Put

• NFLX DEC 17, 2027: $64 Short Put

• NVDA JAN 21, 2028: $130 Covered Call

Our open positions now span several expiration dates, ranging from weekly covered calls to long-dated options extending into 2028.

Weekly Options Premium

Our reported options premium collected during Week 80 reached $78.94, slightly below the previous week’s $101.

As we let our 100 shares of Bristol Myers Squibb (BMY) get called away at $59, we also reduced our margin balance by $5,900. Our outstanding margin debt now stands at approximately $2,397, actually a slightly better position than before we entered the BMY buy-write trade two weeks ago.

In theory, if we directed the entire $78.94 in weekly options premiums toward paying down margin debt, it would take approximately 31 weeks, or just over seven months, to eliminate the remaining balance.

Of course, this assumes consistent weekly premium collections, no additional borrowing, and no interest expenses or trading losses. Real life is rarely that straightforward.

To complicate matters further, we continue reinvesting some of our proceeds into fractional shares rather than directing every available dollar toward margin repayment.

This week, we added:

• 0.1 share of BMY

• 0.1 share of BAC

• 2 shares of NIO

These small purchases are part of our gradual accumulation strategy. They won’t transform the portfolio overnight, but over time, they should help us build larger positions and potentially open new opportunities for covered call selling.

A New Long-Term Position: NIO

This week, I also introduced a new long-term position to the portfolio, and it’s a rather speculative one: NIO (NIO).

I have a bit of history with this stock. In the past, I’ve traded NIO options with mixed success, watching the share price climb from around $5 to $55 and then fall all the way back. Quite a roller coaster, and not always a profitable one.

This time, however, I’m taking a different approach. Instead of jumping straight into options selling, I’ve decided to start small and gradually accumulate shares through dollar-cost averaging. The initial idea is simple: buy around 2 NIO shares per week, regardless of short-term price movements, and see where this takes us.

At that pace, we could accumulate roughly 100 shares in a year, potentially enough to start selling covered calls if the stock price and option premiums make sense.

For now, though, the goal isn’t to squeeze every possible dollar out of NIO. It’s to build a small, speculative long-term position without committing too much capital upfront. Let’s see how this experiment plays out.

What We Are Watching Next Week

Next week should be interesting, especially after the recent selloff in technology stocks. The Nasdaq lost around 4.5% last week, and with earnings season picking up, I wouldn’t be surprised to see more volatility.

For our portfolio, however, the main focus will be BMY and our $60 cash-secured put expiring Friday, October 23.

Having just let our 100 BMY shares get called away at $59, we’re back to selling puts. If BMY stays above $60, we should be able to keep the premium and start another cycle. If it finishes below $60, we could be assigned another 100 shares, effectively restarting the covered call side of the wheel.

Either outcome is manageable, although another assignment would increase our margin borrowing again, something I’m not particularly excited about after reducing it to $2,397.

For Week 81, I’d be happy with another $50–$100 in premiums, provided we don’t take unnecessary risks to get there. The most interesting decision will likely come on Friday, when our BMY $60 put expires.

Will we keep the premium and sell another put, or get assigned and return to covered calls? Let’s see what next week brings!

Week 79 brought a significant change to our options-selling strategy. After approximately 18 months of actively managing Nvidia (NVDA) covered calls and weekly credit spreads, we decided…

Read more

This week, the portfolio came under pressure as both BAC and NFLX declined. In addition, the U.S. dollar strengthened against the euro, which reduced my EUR-reported portfolio value by a few additional dollars due…

Read more

The $14,000 milestone remains within reach, but we have now been struggling to break through that level for several weeks.

The portfolio is now up 34.41% year to date. For comparison, the S&P 500 is up roughly 13% i…

Read more

This weekend we escaped Tbilisi for a road trip to Svaneti with our friend and driver, Vazha. After an overnight stop in Kutaisi and a long drive deeper into the Cauc…

Read more

Writing back from Tbilisi, where this has been a particularly interesting week. Today we said goodbye to the apartment we rented next to the Parliament.

I really enjoyed living there, but we are already enjoying our new place even more.

Hopefully, this will be our home for years to come — or perhaps the next step will be …

Read more

Now back to the port…

Read more

As of August 28, 2026, our stock portfolio closed at $13,735, marking a 1.95% increase we…

Read more

Meanwhile, the school year has already started in Tbilisi, so we’ll be arriving a few days late. We probably won’t return…

Read more

As of August 14, 2026, our stock portfolio closed at $13,606, which is another increase by …

Read more

Which, to be fair, makes me a bit worried. New highs feel great, but history has a habit of reminding us that big rallies can…

Read more

Despite the slight weekly decline, the longer-term picture remains encouraging. The portfolio is now up 24.46% year to date, comfortably ahead of both …

Read more

The portfolio’s growth was significantly supported by the recovery in Netflix (NFLX), which finally closed above $70 after trading below that level for some time.

In recent weeks, portfolio performance had been weighed down primarily by the underperforming NFLX put …

Read more

The loss came after Netflix’s earnings report, which sent NFLX shares down roughly 10% at one point. Although we hold only a small position in the stock itself, our longer-dated NFLX put option created a meaningful drag on the overall portfolio.

Had NFLX remained fl…

Read more

This week, I opened several new positions, despite saying over the past few weeks that I would probably avoid doing so.

I reintroduced Bank of America stock to both the stock and options sides of the portfolio. Today, I also opened a new cash-secured put position in the Finnish forestry company Stora Enso.

You can read more about my reasoning behind both positions here:

• Why I Bought Bank of America Stock After Selling a Cash-Secured Put

• From Clearing Bushes to Selling Stora Enso Put Options: An 11.65% Annualized Trade

On a year-to-date basis, the portfolio is up 25.79%, outperforming both the S&P 500 (+10.37%) and NVIDIA (+11.24%).

Read more

The U.S. stock market week was shortened, with markets closed on July 3 in observance of the July 4th Independence Day holiday.

But for us, the real highlight of the week was not the market. After 16 years and 3 months since I met my better half, we finally got married tod…

Read more

Greetings from Latvia! This week, we skipped the last few days of school in Tbilisi and traveled to Latvia to celebrate the Midsummer Solstice. We spent time with family and friends, enjoyed the traditional festivities, had a few beers, a…

Read more

As of June 19, 2026, the portfolio value increased by +0.76% compared to the previous week, reaching $12,761.

On a year-to-date basis, the portfolio is up 23.77%, outperforming both the S&P 500 (+9.36%) and NVIDIA (+11.56%). While comparing the portfolio to…

Read more

Over the past week, I traveled to Dublin, Ireland, where I combined family time, sightseeing, and a bit of investing research.

While exploring downtown Dublin with my daughter, I made a few spontaneous additions to our long-term stock portfolio after visits to familiar businesses such as McDonald’s and Papa John’s. These purchases w…

Read more