Advice Line with Chris Riccobono of UNTUCKit
Chris Riccobono, founder of Untuckit, joins Guy Raz to advise three entrepreneurs on scaling their businesses. The episode covers challenges in apparel retail, customer acquisition strategies, and the importance of identifying core customer tribes while exploring unconventional marketing channels.
Summary
Chris Riccobono returns to How I Built This Lab to serve as an advisor on the Advice Line segment. He discusses how Untuckit has navigated recent challenges including significant tariff impacts (approximately $9 million pulled from their bank account), the removal of the de minimis rule for Mexico shipments, and their new entry into wholesale partnerships with department stores. Riccobono also updates on Greatness Wins, a secondary athletic brand they pivoted to focus on wholesale golf shop distribution rather than relying solely on expensive paid social advertising.
The episode features three caller segments. Adrian Alvarez, a college sophomore, founded AeroShorts, a hybrid shorts company generating $400,000 in year-two revenue. Riccobono and Raz advise him to clearly define his target tribe (suggesting volleyball players as a specific niche rather than positioning as universal shorts), consider raising $150,000 from friends and family to fuel growth, and allocate capital strategically between product quality and marketing rather than spreading resources too thin across undefined audiences.
Preet Anand calls with Snug Safety, a senior check-in service generating mid-six-figure subscription revenue ($400,000) with 70% word-of-mouth growth. The conversation focuses on awareness building with a limited marketing budget. Riccobono recommends terrestrial radio and podcast sponsorships targeting trusted voices that resonate with adult children of seniors, alongside earned media through local news and publications, avoiding social media which he views as ineffective for trust-based products.
Derek, the final caller, operates Hockey Ninja, a hockey visor company with premium materials generating approximately $250-400,000 in revenue while maintaining a full-time job. He seeks guidance on whether to pursue social media growth or leverage recent NHL clearance to partner with professional players. Riccobono suggests the dual-path approach: work with non-superstar NHL players on modest deals, and consider offering significant equity (25-50%) to a recognizable player who genuinely believes in the product's superiority, as the player becomes both ambassador and stakeholder in growth.
Throughout all segments, Riccobono emphasizes the fundamental challenge of retail and apparel: customer acquisition costs have increased dramatically since early social media advertising, requiring founders to diversify marketing channels beyond paid social, including radio, traditional media, influencer partnerships, and earned media. He stresses the importance of product quality, clear messaging, and customer retention (noting Adrian's 60% repeat rate as solid) while warning that building a meaningful brand requires capital deployment and patience.
About this episode
<p>Today’s callers: Adrian from California wants to grow his apparel company to complete with big-name athletic brands. Then, Preet from the Rockies looks for strategies to reach seniors and their children with his daily check-in app. And Derek from Virginia considers social media and professional partnerships to advertise his hockey equipment brand. </p><p><br /></p><p>Plus, Chris talks about launching a new athletic apparel brand while continuing to grow UNTUCKit.</p><p><br /></p><p>Thank you to the founders of Eras Shorts, Snug Safety, and Hockey Ninja for being a part of our show.</p><p><br /></p><p>If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to <a href="mailto:[email protected]" rel="noopener noreferrer" target="_blank">[email protected]</a> or call 1-800-433-1298. </p><p><br /></p><p>And be sure to listen to <a href="https://www.art19.com/shows/831bd173-0992-41b7-b1eb-112db904d947/episodes/3f71833c-c81d-450e-8873-43e43fbf29d3/embed" rel="noopener noreferrer" target="_blank">UNTUCKit’s founding story</a> as told by Steve on the show in 2017.</p><p><br /></p><p>This episode was produced by Chris Maccini with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang.</p><p><br /></p><p>You can follow HIBT on <a href="https://x.com/HowIBuiltThis" rel="noopener noreferrer" target="_blank">X</a> & <a href="https://www.instagram.com/howibuiltthis/" rel="noopener noreferrer" target="_blank">Instagram</a> and sign up for Guy's free newsletter at <a href="http://guyraz.com/" rel="noopener noreferrer" target="_blank">guyraz.com</a> and on <a href="https://guyraz.substack.com/" rel="noopener noreferrer" target="_blank">Substack</a>.</p><p>See Privacy Policy at <a href="https://art19.com/privacy" rel="noopener noreferrer" target="_blank">https://art19.com/privacy</a> and California Privacy Notice at <a href="https://art19.com/privacy#do-not-sell-my-info" rel="noopener noreferrer" target="_blank">https://art19.com/privacy#do-not-sell-my-info</a>.</p>
Key Insights
- Riccobono discovered that Untuckit's early success came from using unconventional channels (airline magazines, radio, Howard Stern, USA Today print ads) at a time when competitors exclusively relied on paid social media, a counterintuitive strategy that worked because it had less competition.
- Riccobono identifies a fundamental shift in how seniors discover services: they are reached more effectively through terrestrial radio personalities and trusted community sources rather than social media advertising, requiring different marketing strategies than younger demographics.
- Riccobono observes that Adrian Alvarez achieved a 60% repeat customer rate with AeroShorts while still in college, indicating strong product-market fit and customer satisfaction that makes the brand vulnerable to failure only if growth capital runs out before scaling.
- Riccobono notes that professional hockey equipment managers are so overwhelmed during playoff season that approaching them requires strategic timing (off-season or at industry conferences), and that product placement on players is necessary regardless of product quality to drive credibility and sales.
- Riccobono recognizes that Snug Safety's 70% word-of-mouth growth rate suggests strong product-market fit, but awareness remains the bottleneck rather than conversion, pointing to NPR and AARP mentions as proof that earned media drives significant year-over-year revenue increases.
- Riccobono contends that offering a player equity in a company (25-50%) creates stronger incentive alignment than cash compensation, as the player becomes a long-term stakeholder motivated to promote the brand for its growth potential rather than a one-time payment.
- Riccobono reflects that he delayed enjoyment of building Untuckit by focusing excessively on problems and setbacks, and that his improved mindset with Greatness Wins involves accepting friction as inevitable rather than viewing challenges as personal failures.
- Riccobono argues that AI and ChatGPT have created a new customer discovery challenge where brands must optimize for appearance in large language model outputs rather than traditional SEO, representing an emerging frontier in customer acquisition strategy.
Topics
Transcript
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