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Advice Line with Chris Riccobono of UNTUCKit
Brief
UNTUCKit co-founder Chris Riccobono returned to the How I Built This Advice Line with Guy Raz to take three startup calls and reflect on lessons from UNTUCKit’s recent turbulence. Riccobono described a sharp cash hit — roughly $9 million withdrawn due to tariffs and the sudden removal of a long-standing de minimis rule — which accelerated the brand’s move into wholesale and department-store distribution alongside e‑commerce. He reiterated UNTUCKit’s growth playbook: mix channels beyond paid social (airline magazines, radio, TV and select earned media) and put capital behind product and marketing when you intend to scale.
The first caller, Adrian Alvarez of Aero Shorts, is a founder who launched the hybrid short brand in high school; he reported $100K in year one and an expected $400K in year two, with a 60% repurchase rate and a $35 price point. Riccobono and Guy advised Adrian to define a tight “tribe” (for example, volleyball players/college-age customers), consider a $150K friends-and-family raise to fund growth, and test focused channels (volleyball-specific placements, TikTok content and measured ad spend) rather than trying to be “shorts for everyone.”
Preet Anand of Snug Safety explained a daily check-in app for seniors (founded 2017) with roughly $400K ARR and a $20/month plan. With a marketing budget up to $50K, Guy and Chris recommended earned media, terrestrial radio/syndicated hosts, local TV, and outreach to adult children and geriatric clinicians — channels that build trust for an older demographic — instead of broad paid social. Finally, Derek from Hockey Ninja (a side business averaging ~$250K in revenue, with products priced roughly $50–$80) described recent NHL clearance, premium Makrolon/Lexan optics and 120 mph testing. Advisors urged getting the product onto players/equipment managers, using player partnerships strategically (including creative compensation or equity), and supporting athlete endorsements with deliberate marketing spend. Riccobono closed with a recurring theme: entrepreneurship is relentlessly hard, so protect mental bandwidth, prioritize product + measurable marketing, and keep iterating — and when possible, enjoy the journey.
Why it matters
Chris Riccobono (UNTUCKit) said tariffs and a change to the de minimis rule removed roughly $9 million from UNTUCKit’s bank account, forcing the brand to push into wholesale and department stores while managing cash flow.
Key details
- Caller Adrian Alvarez (Aero Shorts) — who started his athleisure brand in high school — reported $100,000 in year-one sales and is on track for about $400,000 in year two; Chris recommended defining a core tribe, considering a $150,000 friends-and-family raise, and deploying funds to product + marketing with a short-term focus on the volleyball niche.
- Preet Anand (Snug Safety) described a daily check-in app for seniors founded in 2017; Preet said Snug is at mid-six-figures (about $400K ARR), charges $20/month, and can deploy up to $50,000 in marketing this year — Chris and Guy advised earned media, terrestrial radio reads, local TV, and targeting adult children and geriatric/primary-care channels rather than heavy paid social.
- Derek (Hockey Ninja) runs a hockey visor/full-face hybrid side business averaging ~$250K (peaked $400K); he sources Makrolon/Lexan from Bayer, claims optical and anti-fog advantages, and tests visors to 120 mph — advice included getting product on players/equipment managers, using targeted athlete partnerships, and considering equity for a strategic player partner.
- Chris emphasized channel-mix lessons from UNTUCKit: in addition to paid social, invest in unconventional brand channels (airline magazines, radio, TV, Howard Stern) and be ready to pivot marketing strategy as acquisition costs rise and AI/search behavior changes.
- Across calls, Guy and Chris repeatedly advised narrowing focus to a specific tribe before scaling, prioritizing product quality and measurable marketing spend, and preparing to raise capital to accelerate growth when aiming for larger scale (e.g., $50M ambitions).