Sycamore Portfolio Update | Q2 2026
Meanderings, performance update, and in-depth updates on the portfolio
Meanderings
Building a newsletter business in the age of AI is hard. Substack is so saturated with research and opinions and self-proclaimed experts that it feels nearly impossible to differentiate yourself. I will never tell you I am an expert on a subject matter. Even after spending many years studying theology, philosophy, and business, I am no expert on any of them.
But here’s my opinion on two differentiators that matter:
1.) Personalism. That’s right, good old fashion human persons connecting with other human persons. Using your real name, talking about your real life, and being honest about your real wins and losses.
2.) Performance. In the investment business, and especially because of AI, this is a primary differentiator. As I said, everyone’s an expert on everything, at least that’s what they think, so the second piece of separating yourself from the homogenization is to post great investment results. Frustratingly, it has been a difficult 11 months for me.
The good news is this is what Sycamore has always been. Personal, honest and transparent. I have had a heck of a 6-year run posting a 25.1% CAGR over that time, but man the last 11 months have been brutal.
I have been incredibly disappointed in my performance during that time, especially as I have also been trying to build this as a legitimate paid newsletter. And several have encouraged me to reconsider my strategy as it has been crushing my near-term results.
Nonetheless, I believe my best days are ahead of me so I will keep concentrating into my best ideas. And if my best days are not ahead of me, that’s okay as well. “The Lord gives and the Lord takes away, blessed be the name of the Lord” (Job 1:21).
Anyways, with all that said, here are some thoughts on two of my current positions.
The Trade Desk: Building Tailwinds
June was a terrible month for the stock, but actually a great month for the business. Tailwinds are building.
Publicis relationship repaired: After Publicis pulled its recommendation of TTD in March over fee-transparency dispute (to which I called BS on from the start), the two sides settled on June 12 and Publicis formally reinstated TTD to its recommended DSP list on June 15 removing a major headwind. Publicis is the largest holdco. Keep in mind the stock was trading around $28 /sh when this news hit and the stock has been in a tailspin ever since. This headwind is now a tailwind and the stock is trading around $19 /sh. I am a buyer sub-$20.
Samsung home screen inventory deal: Samsung Ads announced June 10 that it’s opening its premium Smart TV home screen inventory to programmatic buying for the first time, with The Trade Desk named as one of the first two DSP partners. Google DV360 is the other partner, which is no problem in terms of competition because that platform exists to buy YouTube almost exclusively. Rollout begins globally in Q3 2026. This is new, high-value CTV inventory that hasn’t been programmatically accessible before. Samsung ships ~45M TVs annually, it’s a big opp.
Amazon Ads facing FTC scrutiny: Bloomberg reported June 16 that the FTC has drafted a potential complaint against Amazon over allegedly misleading advertisers, with possible penalties in the billions and multiple state AGs involved. TTD stock will move in a big way if this does end up hitting.
Leadership stabilizing: TTD named Nate Olmstead (former CFO of Penguin Solutions and Logitech) as permanent CFO on June 1, effective July 9. The company also brought on Sarah Gavin as CMO and she started June 15. Additionally, on June 11, the board added media veteran David Haddad.
Political ad spending incoming: The 2026 midterms are on track to be the most expensive in history, with AdImpact projecting roughly $10.8B in total political ad spend. Connected TV is the only channel expected to grow versus 2024, forecast to hit about $2.5B. TTD is well-positioned to capture a share of that spend as it ramps into Q3/Q4.
Will the world cup be a boost for Q2 numbers or Q3 guide? Yet to be seen.
Lot’s of tailwinds building for a stock that is completely broken.
PoolCorp: Great Rotation Beneficiary
PoolCorp has been out of favor for no fault of their own, but the stock worked well in June, up 18.5%.
My baseline assumption here (and in a couple other names I own - more on that below) is that the boring cash generative businesses are benefiting from the AI infrastructure pullback/profit taking. This tracks with the broader “Great Rotation” playing out in the market this quarter, with flows moving out of chips and into staples/healthcare/homebuilders.
At the same time this has been going on, the company removed the CEO and was dropped from the S&P 500, and yet the stock has pretty much been up and to the right every day. The stock also looks pretty de-risked at this point after the 2025 and first-half 2026 drawdown, which may be part of why the bad news hasn’t stuck.
It was my intention to continue adding to this name but I’m holding at this point in time and would consider adding below $185 if given the opportunity.
Performance Update
Very bad.
Below is my full portfolio and updates from an active June.