Podcast Summary

Podcast: Making It with Jon Davids

Episode 224: “I Had No Idea How To Make a Shirt. Now We Sell $200M/yr.”
Guest: Chris Riccobono, Founder of UNTUCKit
Date: October 28, 2025

Episode Overview

In this episode, Jon Davids sits down with Chris Riccobono, founder of UNTUCKit, exploring how Chris identified a seemingly niche problem—men’s shirts that looked bad when untucked—and turned it into a $200-million-per-year business, despite having zero experience in fashion. The conversation covers product innovation, scaling challenges, marketing breakthroughs, the impact of COVID, and why UNTUCKit succeeded where so many other apparel startups have struggled. Chris also shares his advice for entrepreneurs, lessons from launching a new business, and thoughts on the future of DTC and retail.

Key Discussion Points & Insights

1. The Untucked Shirt Problem – Spotting an Overlooked Opportunity

• Origin Insight: Chris noticed after college that men’s button-down shirts were all too long to wear untucked; nobody made shirts with the right length (01:19).
  • "Every shirt that I wore was down to my mid thigh...not only one would be down to the mid thigh, one would be down to your knees...they didn't even measure length at the time." — Chris Riccobono [01:29]
• Market Validation: He informally surveyed men outside the PATH train in Hoboken, NJ, and found 95% had the same problem (02:58).
• Reluctance from Industry Insiders: Early investors, especially older men, didn’t recognize the problem due to their habit of always tucking in shirts.
  • “Back then, the older guy always tucked his shirt in... they thought I was crazy.” — Chris Riccobono [01:54]

2. From Zero Apparel Experience to Product Innovation

• Learning Curve: Chris admits he “had no idea how to make a shirt.” He learned from scratch by visiting garment district manufacturers and learning about ‘zero tolerance’ production (04:44).
  • "I realized how complex making a shirt is...one reason everyone didn’t do it, it costs a lot of money to make a shirt that hits the right length every time." — Chris Riccobono [04:52]
• Manufacturing Challenge: Coming up with a consistent length required costly processes—double washing for shrinkage, 100% inspection, stricter tolerances (06:19).
  • “If our shirt was an inch too long, we look like every other shirt. If it was an inch too short, you couldn't wear it.” — Chris Riccobono [06:11]
• Competitive Moat: This manufacturing difficulty became a unique advantage—other brands found it too expensive or difficult to copy.
  • “Anyone who sees a shirt untucked calls it an UNTUCKit. That’s the whole tissue/Kleenex thing or the Xerox.” — Chris Riccobono [08:06]

3. Breaking Through with Creative, Old-School Marketing

• Early Funding Constraints: Started with just $100k, couldn’t afford digital marketing—used PR, gorilla tactics, and direct interactions (09:36).
  • “We had no money to launch...we did PR because that’s all we could afford.”
• Radio Marketing “Aha!”: First big breakthrough was live reads on NYC sports radio; $15k spent yielded a 4x return, driving 1,500 people to their website in a minute (09:36).
  • “We made four times our money. So we did it again and again...that was our growth...3 million to 15 million to 40 million...” — Chris Riccobono [10:53]
• Unconventional Channels: Tried everything, including airline magazines and cards handed out at transit hubs. UNTUCKit stood out by advertising everywhere: “You would see us literally everywhere” (12:19).
• Early Paid Digital: Early days of Facebook ads were cheap (“cost nothing”), but Chris stresses it was offline diversity—PR, radio, print—that made the brand omnipresent (12:19).

4. Growth & Scaling Tactics in a Changing Landscape

• Omnichannel Advantage: As digital became crowded and costs soared, UNTUCKit found competitive advantage by diversifying spend—airline magazines, Howard Stern, print, and later, brick-and-mortar stores (16:47, 22:59).
  • "Our stores are incredibly efficient...almost all profitable...competitors can’t open 80 stores profitably. That’s a competitive advantage." — Chris Riccobono [17:37]
• Store Openings = Marketing: Opening stores in unexpected markets (e.g., New Mexico) acted as both sales channels and billboards for local awareness (22:59).
  • “I love opening stores everywhere, literally everywhere. There’s no downside as long as the cost makes sense.” — Chris Riccobono [22:59]
• Brand Loyalty: In-store experiences created real loyalty—many customers had known about UNTUCKit from media but needed the physical store to convert (21:19).

5. Finances, Profitability & Surviving Covid

• Lean Operations: UNTUCKit raised surprisingly little capital compared to the competition—only $8 million “on the books” up to $80M+ in sales (28:33).
  • “We raised $100k...the next time we raised was on our way to $80 million...Bonobos had raised like $200M, we had put $8M on the books. That’s pretty crazy.” — Chris Riccobono [28:49]
• Covid Whiplash: About to sell the company for $800 million in early 2020, UNTUCKit suddenly faced bankruptcy as sales evaporated and stores closed (29:55).
  • “I was on the phone in front of my house...with bankruptcy attorneys, trying to avoid declaring bankruptcy...It happened...in two and a half months.” — Chris Riccobono [29:55]
• Pivot & Recovery: Focused on survival, took on debt, shrunk costs, and only recently in 2024 raised fresh capital to pay down debt and restart expansion (33:06, 33:10).
• No Plateau: Marketing was sharply reduced during Covid, but once spend resumes, growth potential remains strong due to customer loyalty and the still-untapped wholesale channel (34:11).

6. Adapting to Marketing Trends & Influencer Strategy

• Influencer Paradox: Chris notes influencer marketing is now “saturated and hit-or-miss”—sometimes a million-follower influencer yields zero sales, while smaller ones drive big results (19:32).
• The Importance of Channel Diversity: He stresses entrepreneurs can't solely rely on paid social; finding alternative, creative channels is more sustainable (39:34).
  • “You can’t put all your eggs in this influencer paid social basket. It’s just, you’re not going to be able to grow fast, profitable.” — Chris Riccobono [39:34]

7. Advice for Early-Stage Entrepreneurs

• Apply Lessons to New Ventures: Chris is reliving the early hustle with his new athletic brand and emphasizes scrappiness, creative channel thinking, and resisting the DTC playbook herd (40:44).
  • “You have to think of other ways to acquire customers outside of just paid social, Google, and TikTok. That’s my advice.” — Chris Riccobono [40:44]
• Market Saturation Warning: Chris predicts consolidation; too many brands are clustered in the $2-$50M range, many will face reality soon (41:24).

Notable Quotes & Memorable Moments

• “Anyone who sees a shirt untucked calls it an UNTUCKit. That’s the whole tissue/Kleenex thing or the Xerox.” — Chris Riccobono [08:06]
• “Our stores are incredibly efficient...they’re almost all profitable...most companies are closing stores...we’re opening another 80.” — Chris Riccobono [17:37]
• “Most of these stores are losing money...men don’t care about [luxury buildouts], they care about efficiency.” — Chris Riccobono [24:23]
• “It’s not like I invented some complex app...It's a shorter shirt, you know...” — Chris Riccobono [21:19]
• “You have to think of other ways to acquire customers outside of just paid social...” — Chris Riccobono [39:34]
• “For 100 years...there were 12 men's brands...now there are 300...and all of these brands are actually doing decent...but it can’t last forever like this.” — Chris Riccobono [41:24]

Important Timestamps & Segment Highlights

• [01:19] – The original insight and market validation for UNTUCKit
• [04:44] – Chris explains his “no idea” approach to shirt-making, and manufacturing complexity
• [09:36] – Low-budget PR and the breakthrough with radio advertising
• [12:19]/[14:31] – Early paid social, omnichannel marketing
• [16:47]/[17:37] – Retail stores as marketing engines, and why UNTUCKit’s stores thrive
• [21:19] – Breakthrough milestone moments and adding physical retail
• [28:33] – UNTUCKit’s unique bootstrapped approach and late fundraising
• [29:55] – Company almost sells for $800M and then nearly goes bankrupt in months due to COVID
• [39:34] – Chris’s advice: don’t bet everything on social/influencer marketing
• [41:24] – The crowded men’s apparel landscape and looming consolidation

Tone and Language

The conversation is pragmatic, direct, and insight-packed, with Chris Riccobono's honesty about his failings and learning curves, his tactical breakdowns, and Jon Davids’ friendly, business-savvy probing. The episode is a goldmine for entrepreneurs wanting actionable advice and a backstage view of turning a simple idea into a household name.

For Those Who Haven’t Listened

This episode is a must-listen for startup founders, marketers, and anyone interested in how real entrepreneurship looks beyond the hype. Chris Riccobono demystifies the UNTUCKit journey—showing that grit, relentless reinvention, and channel diversification build enduring brands. He warns that what worked a decade ago in DTC is obsolete, advocates for retail and creative media, and tells the hard truths about Covid, cash crunches, and bouncing back. The practical and philosophical lessons make this a standout for anyone scaling—or aspiring to scale—a company today.