
Summary
Written by a model from the transcript; not yet reviewed.
Host Guy Raz and returning guest Chris Ricobono, co-founder of UNTUCKit, host an advice line episode where they field calls from three early-stage founders building distinct consumer physical-product and service businesses. Adrian Alvarez calls in from Sacramento with his $35 hybrid shorts brand, Arrows Shorts, seeking advice on scaling into a mainstream brand. Preet Anand calls in from the Rockies with Snug Safety, a free daily check-in app for seniors living alone, looking for strategies to grow market awareness on a targeted budget. Derek calls in from Arlington, Virginia, with Hockey Ninja, a side-hustle company specializing in high-end hockey visors and titanium hybrid full-face shields, trying to decide between social media marketing and pursuing professional hockey endorsements. Ricobono and Raz analyze each founder's metrics, customer demographics, and distribution challenges, offering concrete advice on community focus, marketing channels, and equity partnerships.
- Founders operating in crowded apparel markets should narrow their initial focus to a distinct niche where competition is low before attempting to scale broadly. 17:16
- Founders marketing trust-based products for older demographics should test terrestrial radio and targeted audio ads rather than relying solely on social media. 30:11
- Entrepreneurs with side hustles in specialized niches can leverage strategic equity partnerships with prominent athletes instead of paying expensive endorsement fees.
Chapters
- 0:00Sponsor Intro and Founders’ Hard Questions
The episode opens with the sponsor Anthropic’s pitch and Guy Raz’s framing of founders’ hard questions that spark the show’s narrative.
- 3:29Guy Raz Introduces the Advice Line Format
Guy explains the call‑in format, how listeners can reach the show, and sets up the first guest, Chris Riccobono of Untuckit.
- 4:18Chris Riccobono’s Untuckit Journey and Recent Challenges
Chris recounts his medical‑device background, the birth of Untuckit, and the impact of tariffs, COVID, and new wholesale expansion on the business.
- 6:17Strategic Pivot: Untuckit’s New Brands and Marketing Tactics
Chris discusses launching a sports‑wear line, shifting to wholesale, and blending paid social with traditional media to stay competitive.
- 12:00Advice Line Call 1 – Adrian Alvarez’s Hybrid Shorts
Adrian introduces his teen‑aged athleisure brand, shares growth metrics, and asks Chris for brand‑building advice to reach a mainstream audience.
- 24:43Advice Line Call 2 – Preet Anand’s Snug Safety App
Preet explains the senior‑care check‑in app, its funding story, and seeks guidance on raising awareness among older adults and their families.
- 39:34Advice Line Call 3 – Derek’s Hockey Ninja Visors
Derek presents his hockey‑equipment startup, discusses product differentiation, and asks whether to focus on social media or professional athlete endorsements.
- 47:17NHL Endorsement Strategy
Discussion of how NHL players can be leveraged for endorsements and the strategic allocation of marketing dollars.
- 47:58Equity Deals with Influential Players
Conversation about offering equity to star players such as Jack Hughes to secure brand promotion and potential future revenue streams.
- 49:41Future Expansion into Other Sports
Speculation on extending the visor brand into baseball and other sports, highlighting the adaptability of the product line.
- 50:23Reflecting on Early Challenges
Chris Riccobono reflects on the difficulties of starting Untuckit, emphasizing resilience and the importance of moving forward despite setbacks.
- 51:15Learning to Enjoy the Journey
Chris shares advice to enjoy the entrepreneurial journey, stay resilient, and keep pursuing new ideas after failures.
Highlights
- 5:20
Sudden Tariff and Tax Rule Hitsdata
The guest explains how unexpected tariff hits and the sudden removal of the 3-2-1 de minimis shipping rule by the government pulled nine million dollars directly out of UNTUCKit's bank account overnight.
- 6:27
Pivoting Into Green Grass Golf Shopsstrategy
The guest details how his athletic apparel brand Greatness Wins pivoted its marketing strategy away from expensive paid social media and into green grass golf shops to serve as both revenue and free marketing.
- 16:41
Raising Early Capital for Growthinsight
The guest advises a young caller that building a major national brand requires raising early capital from friends and family to properly fund marketing and fuel growth.
- 27:17
Targeting Adult Children of Seniorsinsight
The host and guest discuss how a safety check-in service for seniors must strategically target the adult children of elderly parents rather than just the stubborn seniors themselves.
- 41:43
Sourcing Automotive Grade Plasticsstory
A caller describes sourcing Macrolon Lexan plastic from Germany—the exact same material used for Audi and Bugatti headlamps—to ensure extreme impact resistance and optical clarity in hockey visors.
Quotes
“We went on Howard Stern. We went on the USA Today's back of New York Post.”
Unnamed speaker · 8:23 “You might go spend that money on marketing and lose the seven grand you just raised.”
Unnamed speaker · 50:56 “You go to guys who are maybe, you know, the third, fourth line, you can get them for nothing.”
Unnamed speaker · 49:17 “But you know what's funny? We thought through it and said, you know what? We'll one day get them back.”
Unnamed speaker · 52:18 “You got to just kind of keep moving forward.”
Unnamed speaker · 50:38 “The brand is called Hockey Ninja. Derek, thanks so much for calling in.”
Guy Raz · 49:54
Sponsored segments
- Anthropic 0:00–0:53
- US Bank 1:33–3:06
- Anthropic 20:20–20:39
- Delta SkyMiles Reserve 22:07–23:07
- NetSuite 36:36–37:53
- Framer 38:00–39:04
- Anthropic 53:45–53:48
About this episode
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. Plus, Chris talks about launching a new athletic apparel brand while continuing to grow UNTUCKit. Thank you to the founders of Eras Shorts, Snug Safety, and Hockey Ninja for being a part of our show. 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 [email protected] mailto:[email protected] or call 1-800-433-1298. And be sure to listen to UNTUCKit’s founding story https://www.art19.com/shows/831bd173-0992-41b7-b1eb-112db904d947/episodes/3f71833c-c81d-450e-8873-43e43fbf29d3/embed as told by Steve on the show in 2017. This episode was produced by Chris Maccini with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang. You can follow HIBT on X https://x.com/HowIBuiltThis & Instagram https://www.instagram.com/howibuiltthis/ and sign up for Guy's free newsletter at guyraz.com http://guyraz.com/ and on Substack https://guyraz.substack.com/. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Transcript
10,388 words · 5 speakers
Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.
Topics
- Untuckit
- Claude
- NHL
- Hockey Ninja
- Vioris
- Pro Three-on-Three League
- World Cup
- Era Shorts
- Snug Safety
- Lululemon
Page updated · transcript and summary are machine-generated