Podcast Summary: The Ryan Leak Podcast
Episode: What To Get Someone Who Has Everything
Host: Ryan Leak
Date: December 15, 2025
Overview
In this heartfelt holiday episode, Ryan Leak tackles a perennial challenge: what to give people who seem to have everything. Drawing from his personal experience and coaching wisdom, Ryan reframes the idea of gift-giving, suggesting that the most memorable and transformative gifts are not material but deeply personal words of encouragement. He offers actionable advice on how to craft meaningful notes, voice memos, or videos that will be cherished far longer than any store-bought item.
Key Discussion Points and Insights
The Challenge of Shopping for Those "Who Have Everything"
- Personal Anecdote: Ryan opens by humorously identifying himself as "that person" who is difficult to shop for—not because he’s extravagantly wealthy, but because he tends to buy himself what he wants, making gift-giving a hassle for friends and family (00:15).
- Universal Experience: Many people have loved ones who already own all the things they want, leaving givers at a loss: “There’s nothing you can do to out-Amazon them. You can’t out-Target them.” (01:37)
The Gift Money Can’t Buy: Specific Encouragement
- Ryan’s Advice: He suggests that “the rarest gift you can give isn’t expensive. And that gift is very, very, very specific encouragement.” (02:16)
- Vague vs. Specific Encouragement:
- Vague encouragement is like fast food—satisfying, but fleeting.
- Specific encouragement is “gourmet... Michelin star restaurant,” the kind of thing people keep for years (02:44).
“The truth is, I think you give them something money cannot buy... very, very, very specific encouragement.”
—Ryan Leak (02:16)
The Power and Longevity of Words
- Personal Examples: Ryan has seen people keep notes tucked in bibles, taped to mirrors, folded in wallets—demonstrating the lasting influence of thoughtful words (03:07).
- Societal Contrast: While society celebrates grand gestures, “what people actually crave is to be seen, is to be known.” (03:50)
Why Specificity Matters
- What Makes Encouragement Memorable: The messages that truly stop Ryan in his tracks are ones that reference a specific moment, comment, or impact:
- “The ones that stop me in my tracks are the ones that are specific ... the thing you said three years ago still shapes how I lead today.” (04:37)
- Impact of Speaking Up: “You might think people already know what you think about them, but ... They don’t.” (06:25)
“The biggest mistake that you can make during the holiday season is to assume that they already know.”
—Ryan Leak (06:25)
Delivering Encouragement: Mediums and Methods
- Handwritten Notes: Classic and highly valued.
- Personal Videos or Voice Memos: Ryan recommends these as well, sharing a touching story of a seven-minute voice memo he sent to a friend, who responded with deep gratitude and intention to keep it (08:39).
- The Real Gift: “I slowed down my day long enough to think about you... effort shows love.” (10:36)
“You don’t have to be a poet to be powerful. You just have to be honest.”
—Ryan Leak (11:13)
How-To: Crafting a Memorable Encouragement
Ryan breaks down a three-step structure for writing a note, video, or voice memo that people will keep:
1. Start With Who They Are (11:55)
- Praise who the person is, not just what they’ve done.
- Example: Instead of “You’re amazing at your job,” say, “You make people feel safe at work. I love that about you.”
“The greatest encouragement isn’t about what people produce. It’s about who they are.”
—Ryan Leak (12:15)
2. Point to a Moment (14:05)
- Recall a specific instance of impact or support.
- “I’ll never forget the time you stayed up with me while I was processing that decision.”
- “When you shared that story last month, it reminded me what courage really looks like.”
“When you get specific, that is the soul of sincerity.”
—Ryan Leak (15:28)
3. Tell Them What They’ve Taught You (16:10)
- Articulate the lesson or quality you have gained by knowing them.
- “You’ve taught me how to forgive faster.”
- “You’ve helped me believe in kindness again.”
“When you tell people the impact they’ve made on you, it reinforces their purpose. It’s like you’re giving them a glimpse of their legacy while they’re still here to hear it.”
—Ryan Leak (17:15)
Notable Quotes & Memorable Moments
- “We save our best words for eulogies, when people can’t even hear them anymore. But what if, for Christmas, you gave people their flowers?” (18:01)
- “People might forget the gifts you got them, but they will never forget how your words made them feel.” (18:35)
- “Don’t think about what you can add to their cart, but what you can add to their heart.” (19:46)
- “Your encouragement might be the thing somebody’s been praying for for a long time.” (20:22)
Important Timestamps
- 00:15 – Ryan’s personal reflection on being tough to shop for
- 02:16 – Introduction to the idea of specific encouragement as the ultimate gift
- 03:50 – Contrasting grand gestures with the desire to be seen/known
- 04:37 – Stories of memorable, specific encouragement Ryan has received
- 06:25 – The mistake of assuming people know how we feel
- 08:39 – Story of a voice memo that deeply impacted a friend
- 11:13 – Encouragement to be honest and vulnerable with words
- 12:15 – Start notes with affirming character, not just actions
- 14:05 – Pointing to specific moments as the “soul of sincerity”
- 16:10 – Teaching others how to articulate what someone has taught them
- 18:01 – Give people their “flowers” while they’re alive
- 19:46 – The “add to their heart” challenge
Closing Insight
Ryan wraps up with a charge to listeners: when gifting to someone who has everything, “give them words that outlast wrapping paper... words that remind them that they matter. Because one thoughtful note, video or card can outlast a thousand gifts.” (21:06)
Tone & Style:
The episode is warm, inviting, direct, and honest—carrying Ryan’s signature style of blending inspiration and practical steps, laced with humor and candid personal anecdotes.
Takeaway for Listeners
If you’re struggling with what to give this season, remember: your words of encouragement may be the most priceless, unforgettable gift you could ever give. Be brave—speak, write, or record what you truly see in those you love. It might well be the thing they’ve been longing to receive.