What's in store for you:

1. Photo From My Life
2. Life Thought: The Times They Are A-Changin'
3. Financial Thought: Transitioning Portfolios
4. Good Sh*t: A Complete Unknown

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Photo From My Life:

Life Thought:

The Times They Are A-Changin': In 2018, I had the most fortuitous meeting with a guy named Ben. My boss at the time introduced us as he thought we’d get along. Time has allowed me to reflect, and it's clear this meeting had a massive impact on my life.

If I hadn’t met Ben, I would probably still be working at some mid-size private equity or investment firm, questioning whether this is what I wanted for my life. I could have so easily stayed on that path, but I didn’t. I have Ben to thank for that. His positivity, optimism, and get-shit-done attitude makes for a great business partner (and friend). He's made me better in so many ways.

We created WeHero over 5 years together. I remember those five years as one of the most fun and challenging periods of my life. We started in San Francisco and moved the business to Bend, Oregon during COVID. We hired great people and we supported hundreds of thousands of employees around the world with corporate volunteering.

In 2023, we made the challenging decision to sell to WizeHive, a software player in our space. Ben stayed for a few months after the transaction. Given my background, I stayed to help with the integration. It was our baby and I wasn’t quite ready to leave. I wanted to make sure our team, and our company were in good hands. As I got closer to the decision to leave, we began the process of merging with a large competitor in the space, Submittable. Once again, I got involved in the deal and led the integration of these two businesses after the deal closed. All of a sudden, I looked up, and it had been 2 years since we sold. It’s remarkable how time flies. Should I have left sooner? Maybe. But I felt lucky to support a business I cared deeply about, and it didn’t impact my ability to launch and grow two other businesses I’m deeply proud of: PE Lists and Pono Ventures.

But, the time has come. I’m ready for my next adventure. I’m ready to go back to square zero. I’m ready for that challenge. I’m ready to build my own destiny again. Am I scared? Yes. Am I excited? Yes.

After notifying the WeHero team in April that I was planning to leave, I decided to make one final trip to our Bend headquarters to spend some time with the team. It was a great few days. Sure, there were some sad moments. But it’s reassuring to know that you’re leaving a great team in a good place. Ben and my crazy idea that we conjured up over wine and coffee is a living thing. It will continue to be more than we could have ever expected it to be. Very few founders have this experience, and I’m deeply proud of it.

As I write this on my flight home, I couldn’t help but reflect that life is a series of choices. Some are good, some are bad, but each one leads you to where you are in life. I’m happy. I’m lucky. I feel fulfilled with my WeHero experience. I’m ready to close that chapter. Sure, it’s sad, but change is hard.

If you’re a new reader, I swear my life thoughts rarely get this personal or emotional. Thanks for sticking with me.

Financial Thought:

Transitioning Portfolios: If you’ve been investing long enough — or inherited a portfolio from a legacy advisor — you may be sitting on a random collection of individual stocks. A little Apple here. Some GE from the 90s there. Maybe a biotech company you’ve never heard of.

This isn't necessarily bad, but let's assume you wake up and realize that very few stock pickers can consistently outperform over a lifetime of investing. You've made the decision you want to focus your effort on a global allocation portfolio. You've seen the light!

The challenge: it's hard to make the switch. Many of these portfolios have large embedded gains. Selling everything in one shot could trigger a painful tax bill.

There's good news though. You don’t have to blow up your portfolio and pay huge taxes just to fix it. You can transition to a global, low-cost, diversified allocation gradually by using tax loss harvesting and direct indexing.

Tax loss harvesting lets you sell investments that have gone down in value and realize the loss. These losses can offset gains elsewhere in your portfolio — dollar for dollar — and even offset up to $3,000 of ordinary income per year. If you have more losses than you can use in one year, you can carry them forward indefinitely.

This matters because it softens the tax blow. Instead of paying a huge capital gains bill, you use losses to "buy down" your taxable gains and move your portfolio in the right direction.

Direct indexing is simple in theory: instead of owning a broad-market ETF (like SPY for the S&P 500), you own a portion of the individual stocks that make up the index. This gives you control over which positions you sell, when you realize gains, and how you harvest losses. You can still track the overall index return — but with more tax efficiency.

What does this look like in practice? Imagine you have a $2 million portfolio made up of 50 random individual stocks:

• 30 stocks have gains, totaling +$700k.
• 20 stocks have losses, totaling -$150k.

If you just sell everything, you realize gains and face a massive tax bill. However, there's a better strategy. You can leverage tax loss harvesting.

1. Sell the 20 losing positions first, realizing $150k in losses.
2. Use those losses to immediately offset $150k of gains if you sell some winning positions.
3. Reinvest the proceeds from the sold stocks into a direct indexing strategy to maintain market exposure.
4. Over time, strategically sell pieces of your appreciated positions, using additional tax losses (or future harvested losses) each year to offset gains.

It doesn't happen overnight, but you can make real progress in shifting your portfolio while carefully managing the tax impact over multiple years. You end up with a clean, diversified, tax-efficient portfolio — without paying 30-40% in taxes just to "fix" it.

Good Sh*t:

A Complete Unknown: I’m usually not a big fan of musical biopics. They always feel a little cheesy or forced to me. But A Complete Unknown, the new Bob Dylan movie, really surprised me.

Timothée Chalamet absolutely crushed it. I honestly wasn’t sure if he could pull it off — Dylan is such a unique guy — but he nailed the vibe without making it feel like a bad impression. It just felt real and natural.

The movie itself was way better than I expected too. Instead of trying to cram Dylan’s whole life into two hours, it just focuses on a short but really important part of his career. It made the story way more interesting and way less "Hollywood."

Even if you're not normally into these types of movies, I’d recommend giving this one a shot. I’m glad I did.

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