We’re excited to share that Ashish Khanna, Partner at Hightower Signature Wealth, was recently featured on the Making Sense of Your Money podcast with Dan Pascone. Khanna discussed the deeper side of legacy planning—how families can pass down clarity, values, and preparation alongside financial assets. Below is a recap of the key themes he discussed during the episode.
Khanna’s Path: Why He Moved From Law to Wealth Advising
Khanna shared how his early career as an estate‑planning attorney shaped the way he works with families today. Two moments were especially influential:
- A mentor admitted she struggled with the lifestyle of big‑firm law and encouraged him to think carefully about his long‑term path.
- A late‑night call from a client whose husband was critically ill. Although Khanna had drafted their legal documents, he couldn’t answer her real question: “Are we going to be okay?”
That moment made him realize he wanted to guide families more fully—not just through documents, but through the decisions and conversations that give those documents meaning.
Why Generational Wealth Often Doesn’t Last
Khanna highlighted a long‑term study of 3,000 families that found:
- 60% of wealth transfer failures come from breakdowns in communication
- 25% from unprepared heirs
- 10% from lack of shared purpose
- 3% from technical or legal mistakes1
Most issues aren’t financial—they’re relational.
He explained four patterns that commonly undermine families:
- Silence around money — families avoid the topic, often out of fear or habit
- One‑sided knowledge — parents hold all the information; children hold none
- Documents without context — wills and trusts explain what happens, not why
- Assumptions — when families don’t talk, everyone fills in the blanks differently
The Role of Family Stories
Khanna shared a personal example of recording his father’s life stories—something that helped him reconnect with his own purpose during a difficult period. One story in particular, about his father witnessing a doctor save his grandfather’s life in their small Bombay apartment, shaped his father’s entire career.
It reinforced a belief we hold at HTSW: stories carry values in a way documents cannot.
Estate Planning for Busy Professionals
Khanna emphasized that the biggest mistake high‑earning professionals make is waiting too long to start planning.
As he noted during the episode: “Everyone has an estate plan. It’s just whether you choose it or the state chooses it for you.”
For clients with complex finances—equity, business ownership, multiple accounts—estate planning must connect with tax strategy, investments, and family needs. None of these pieces work well in isolation.
How Families Can Start Better Conversations
Khanna offered several practical steps families can take right away:
- Have the first conversation, even if it feels uncomfortable
- Share the intent behind your estate plan, not just the structure
- Hold a yearly family meeting to keep everyone aligned
- Include your advisor so the discussion stays grounded and clear
What a Rich Life Means
Khanna closed the episode by sharing his own definition of a rich life: living with intention and being honest about where you want to be in the future.
Listen to the full episode on Apple or Youtube
1 Roy Williams/Vic Preisser (2010): Preparing Heirs: Five Steps to a Successful Transition of Family Wealth and Values
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