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  1. How I Built This with Guy Raz
  2. Advice Line with Chris Riccobono of UNTUCKit
Advice Line with Chris Riccobono of UNTUCKit

Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz · Jul 30, 2026

UNTUCKit's Chris Riccobono advises startups on targeted marketing, from niche athletic wear to senior safety apps and pro hockey equipment.

UNTUCKit Ignored Experts and Used 'Dead' Ad Channels like Radio to Scale

While marketing experts pushed paid social, UNTUCKit differentiated itself by advertising in airline magazines, radio, and print. This counterintuitive strategy was crucial for their early growth as it reached an untapped audience for a fashion brand.

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Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago

UNTUCKit's Founder Says AI Chatbots Are Replacing Traditional SEO for Discovery

The next marketing frontier isn't Google search, but ensuring your brand appears when users ask AI chatbots for product recommendations. Companies must develop strategies to be discoverable through conversational AI, a fundamental shift from traditional SEO.

Advice Line with Chris Riccobono of UNTUCKit thumbnail

Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago

To Go Mainstream, DTC Brands Must First Dominate a Niche Tribe

UNTUCKit's founder advises a DTC shorts brand to focus on its initial niche (volleyball players) rather than immediately trying to be "shorts for everyone." A strong, focused brand identity built around a core community is the necessary foundation for broader appeal.

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Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago

Raise Your Friends and Family Round While Sales Are Accelerating, Not Stalling

The optimal time to raise early capital from friends and family is during a period of rapid growth, such as quadrupling revenue. This momentum creates a more compelling story, securing cash for the next phase before growth potentially slows or flatlines.

Advice Line with Chris Riccobono of UNTUCKit thumbnail

Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago

Use Niche Wholesale Channels as a 'Free Marketing' Acquisition Funnel

UNTUCKit's founder strategically placed his new sportswear brand in specialty golf shops. This wholesale channel serves a dual purpose: generating revenue and acting as a free marketing tool, acquiring customers who then discover and purchase other products online.

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Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago

Use Host-Read Radio Ads for Trust-Based Products Targeting Older Demographics

For products like a senior safety app where trust is paramount, host-read radio ads are highly effective. They allow for storytelling and leverage the deep connection listeners have with trusted personalities—a more powerful strategy than visual social media ads.

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Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago

Give a Star Athlete 25% Equity Instead of a Small Endorsement Fee

For a niche equipment brand, securing a top-tier athlete can be transformative. Rather than a small cash deal, offering a significant equity stake (e.g., 25%) turns the athlete into a co-owner, incentivizing them to actively build the brand among peers.

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Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago

UNTUCKit's Founder Kept His Day Job Well Into 7-Figure Revenues

It's a misconception that "true" entrepreneurs must go all-in from day one. UNTUCKit founder Chris Riccobono continued his full-time sales job long after his company was generating millions. This de-risked approach is a valid and often prudent path to success.

Advice Line with Chris Riccobono of UNTUCKit thumbnail

Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago

UNTUCKit Founder's Advice: Stop Letting Inevitable Problems Ruin the Journey

Reflecting on his journey, Chris Riccobono advises founders to reframe setbacks. Problems are constant and unavoidable. Instead of letting them cause pain and depression, accept them as part of the process, shake them off, and focus on moving forward.

Advice Line with Chris Riccobono of UNTUCKit thumbnail

Advice Line with Chris Riccobono of UNTUCKit

How I Built This with Guy Raz·5 days ago