Kelly Gillease

Kelly Gillease is an executive business leader with 20+ years of hands-on experience across all disciplines in marketing at profitable, growth-oriented start-ups. She was a key contributor to successful strategic acquisition exits at Hotwire (IAC), Viator (TripAdvisor) and StudyBlue (Chegg), as well as CMO during NerdWallet's IPO. As a Co-Founder and CMO of Accountable Finance Kelly is leading content strategy and marketing. Kelly’s thought leadership, writing, and editing has been featured in numerous publications including Fast Company, AdAge, Chief Marketer, and Search Engine Land. Kelly was recognized as a 2020 "40 Over 40" honoree by Campaign US.

Recent Posts by this Author

Quantitative Investing 101

Direct Indexing & Tax Loss Harvesting: How They Work Together — and When It’s Actually Worth It

Direct indexing and tax loss harvesting (TLH) are often discussed separately. But in practice, they are most powerful when used together as part of an investing strategy. Direct indexing is the structure; tax loss harvesting is the engine. When combined thoughtfully, they can materially improve after-tax outcomes—far beyond what’s possible with a traditional ETF or mutual fund.For experienced investors evaluating whether the added complexity is justified, the real question is not whether direct indexing can enable tax loss harvesting. What’s important is determining if the tax benefits are large enough to outweigh the trade-offs, or not.

Kelly Gillease

December 22, 2025

Quantitative Investing 101

Direct Indexing for Investors: Strategy, Trade-Offs, and When It Beats ETFs

Direct indexing has moved from institutional portfolios into the hands of individual investors. It’s often touted as “owning the index, but better.” The reality is more nuanced. Direct indexing is a powerful tool for investor control, customization, and tax efficiency—but it also introduces complexity, tracking error, and operational demands that aren’t worth it for every investor. For experienced investors, the right question isn’t whether direct indexing is better than ETFs. It’s when does direct indexing produce superior after-tax outcomes—and when is a simple ETF still the smarter choice?

Kelly Gillease

December 18, 2025

Quantitative Investing 101

Tax Loss Harvesting for Investors: When It Works, When It Doesn’t, and How to Do It Right

Tax loss harvesting (TLH) is often described as a simple tax trick: sell investments at a loss, offset gains, and reduce your tax bill. In practice, it’s a portfolio-level strategy with real trade-offs, execution risk, and diminishing returns if done poorly. For experienced investors, the question isn’t what tax loss harvesting is—it’s when it actually adds value, when it doesn’t, and how to implement it correctly without distorting your portfolio.This article walks through the rules that matter, the situations where TLH works best, and the common pitfalls that quietly erase its benefits.

Kelly Gillease

December 16, 2025

Top Investment Strategies

Do Guru Rules Really Beat the Market? Benchmarking Top Investing Strategies from Famous Investors

Kelly Gillease

November 19, 2025

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