Sharpening the Investor’s Edge: Inside the TIGER 21 Invest Bootcamp 

TIGER 21 Members recently gathered in Washington, D.C. for the TIGER 21 Invest Bootcamp, a two-day program built to strengthen the investing skills that wealth creators rely on to protect and grow what they’ve built.  

The Bootcamp grew out of Member conversations within TIGER 21 investing-focused affinity Networks: namely that the skills that create entrepreneurial success don’t always translate to investing success. 

The event, hosted by Director, Investment Networks Deborah Adeyanju, CFA, CFP®, connected Members with a select group of experts. Through two full days of programming, attendees learned new insights to build confidence around more directly managing their investments, working effectively with wealth advisors, and evaluating investment opportunities. 

In addition to learning sessions, the Invest Bootcamp provided Members with dedicated opportunities to connect meaningfully with each other through small-group sessions, networking receptions, and shared meals. 

“Learning is a huge priority for TIGER 21 Members, but they’ve also told us that meeting other Members is something they truly look forward to,” shared Lisa Holladay, Chief Experience Officer. “Being able to connect deeply with another Member adds a layer of meaning to these event experiences. It’s one of those elements that keeps Members coming back, event after event.” 

Inside the Event: A Deep Dive on Tax-Aware Investing 

Among the featured experts at the Invest Bootcamp was Anatoli Pilchtchikov, Tax Principal, Private Client Services Group at BDO. Pilchtchikov delivered a presentation on tax-aware investing for Members with assets subject to U.S. taxes, framing taxes as “largely a controllable thing, unlike market returns.” 

Pilchtchikov explained that a portfolio that ignores taxes can hand back anywhere from 1–2% of returns each year. Because that drag compounds over a few decades, it can erode close to a third of an investor’s terminal wealth.  

From there, he explained the three levers underpinning all the tax optimization strategies he shared that day:  

• Character: What kind of income it is. Ordinary income is taxed at the highest rates; long-term gains and qualified dividends, much less. 

• Timing: When income is recognized. Deferring income lets pre-tax dollars keep compounding. 

• Location: Where the asset sits. Holding assets in  a taxable account, a traditional IRA, or a Roth IRA creates three different tax situations.  

He started his presentation with the foundational strategies most investors subject to U.S. tax should consider. He also shared several more advanced, founder-focused tax approaches, with the caution that the more advanced strategies are best leveraged with the assistance of a professional. 

Continuing the Learning After the Event 

Bootcamp attendees left D.C. with a stronger command of mission-critical investing concepts. 

“I loved the content and felt it was expertly designed and facilitated. I learned a ton!” shared TIGER 21 Member Lisa Liguori. 

Even after the event, Members will continue to have the opportunity to strengthen their investing portfolios through their Portfolio Defense. During this signature TIGER 21 experience, Members present their entire investment portfolio and gather candid feedback from their Group on their assets, liabilities, income, and expenses. Presenting Members also use the opportunity to go beyond finances to explore other aspects of their lives, including family dynamics, planning for the next chapter, and preserving their legacy for future generations. 

Every first-year TIGER 21 Member presents a Portfolio Defense. In subsequent years, Members can choose to repeat their Portfolio Defense or choose another option from the TIGER 21 Defense Library. The library currently includes resources for Members who wish to present their Estate Planning Defense, Health & Wellness Defense, Legacy Defense, or Philanthropy Exploration Defense. It also includes tools for Members to go deeper when presenting a repeat Portfolio Defense. 

Along with the other elements of the TIGER 21 Member experience—including the monthly Group Meeting, online Lifestyle & Investment Networks, and the events calendar—these resources offer Members a continuous pathway for growth, reflection, and enhanced decision-making. 

Learn more about the complete TIGER 21 Member experience.