Jun 23, 2025 · 1h 13m · how-i-built-this
UNTUCKit: Chris Riccobono
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
UNTUCKit co-founder Chris Riccobono shares the entrepreneurial journey of turning a simple solution for ill-fitting men's shirts into a multi-million-dollar apparel empire, navigating catastrophic early manufacturing defects, viral media attention, and near-bankruptcy during the pandemic.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 38.3% of the talking time here. How this is scored →
Guy as informed peer 3.6 Guest teaching 2.8 Guest disagreement 1.4 Guy pushing back 2.0
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:57 Distinguishing Untuckit from guayaberas
Chris firmly rejects Raz's counterexample of guayaberas, emphasizing that mainstream tailored button-downs were never constructed or measured for untucked wear.
Hardest push from Guy ▶ 29:36 Raz presses Chris on sticking with a flawed factoryRaz refuses to accept that bad shirts were inevitable and explicitly questions why Chris kept working with an overseas factory producing unwearable inventory.
Biggest teaching moment ▶ 30:33 Educating Raz on fabric mechanics and specification limitsChris breaks down the physics of garment washing, fabric growth, and why standard apparel brands avoid committing to exact untucked hem lengths.
Guy holds their own ▶ 53:58 Raz deconstructs the Kleiner Perkins funding structureRaz drills down into the cap table mechanics, distinguishing between primary growth capital and secondary share sales that allowed founders to take money off the table.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Corporate Anxiety, GE Medical Sales, and the Columbia MBA | 3 | 1 | 1 | 1 | Guy Raz establishes Chris's early corporate background and prompts him on his motivations for pursuing an executive MBA at Columbia. The exchange is highly collaborative with Chris candidly sharing his career anxiety and lack of corporate fit. | |
| Early Entrepreneurial Experiments: Wine Vlogging and Other Ideas | 3 | 2 | 1 | 2 | Raz presses Riccobono on the practicality and business model behind his early entrepreneurial experiments like the wine vlog and dating concepts. Chris willingly details how he juggled making video content while hitting his GE sales quotas. | |
| The Las Vegas Epiphany and Partnering with Aaron Sanandres | 4 | 4 | 3 | 3 | Chris explains the origin of the untucked shirt concept and technical tolerances in garment specs. When Raz points out that untucked shirts like guayaberas already existed, Chris distinguishes his product as the first tailored button-down designed for untucked wear. | |
| Prototyping in the Garment District and Finding a Manufacturer | 3 | 3 | 1 | 1 | Raz asks about navigating the Garment District without industry terminology or design experience. Chris explains his cold outreach to pattern makers and his exacting 28.75-inch medium specification. | |
| Early Manufacturing Flaws, Meeting Bjorn, and Slow Iteration | 4 | 5 | 2 | 4 | Raz repeatedly challenges Chris on why he tolerated defective first batches and loose buttons from the Polish manufacturer. Chris educates Raz on the unforgiving nature of fabric shrinkage and quality control tolerances when producing untucked lengths. | |
| Bootstrapping, Marketing Breakthroughs, and Pop Culture Roasts | 4 | 2 | 1 | 1 | Raz and Chris explore the breakthrough radio ad campaign and Untuckit's contribution to modern workplace casualization. Raz contextualizes the brand's cultural impact while Chris recounts leaving his day job at GE. | |
| Retail Expansion, Kleiner Perkins Investment, and Industry Copycats | 4 | 3 | 1 | 2 | Raz inquires about the retail store rollout and fundraising from Kleiner Perkins. Chris clarifies the specifics of the financing structure, noting that most of the round was secondary liquidity rather than balance sheet cash. | |
| The Near $750M Acquisition and the COVID-19 Near-Death Crisis | 4 | 3 | 2 | 3 | Raz probes into the near-acquisition before COVID-19 and the subsequent cash crunch that triggered bankruptcy discussions. Chris walks through the intense operational and personal stress of renegotiating with landlords and suppliers. | |
| Post-Pandemic Turnaround, Wholesale Entry, and Reflections | 3 | 2 | 1 | 1 | Chris outlines Untuckit's return to profitability and wholesale partnerships with department stores. Raz poses reflective questions about long-term exit goals and the balance between luck and grit. |
Statements from this episode (13)
Riccobono: Apparel brands allow 2-3 inch size variances to save money
“If you measure 10 shirts from most companies and a large, same color, same shirt, you'll see a major variance of two to three inches because cotton grows and these companies don't want to spend the extra money to do the quality control needed To make sure that…”
UNTUCKit grew revenue from $90K to $15M over five years
“We grew unbelievably slow, you know, 90,000 dollars 300,000 dollars, 500,000 dollars.
[2029] Guy Raz: This is year one, two, three.
[2030] Chris Riccobono: Yeah, then you know, 3,000,015, and up from there.”
Riccobono: Slow early growth saved UNTUCKit from fatal product defects
“The only reason we survived is because those years we were so small, so we were able to perfect the shirt before we became known.”
Riccobono: Consumers convert when they perceive a brand is larger than it is
“That Opinion from a consumer makes them convert when they feel that you're bigger than you are.”
Riccobono: UNTUCKit reached $53M revenue on $1.3M friends-and-family capital
“No, all friends and family, and doing about fifty three million. Now, the equivalent, I'm not gonna name brands, was, had raised about two hundred million.”
Riccobono: UNTUCKit opened 90 retail stores in two and a half years
“That store did so well in Soho that one year, in three months, that I said, we are now going to open this, that's another X million dollars in revenue, we're going to open five more, and then we opened 90 stores in, I think, two and a half years.”
Riccobono: 70% of early customers refused to buy without physical stores
“Even though all these people were yelling and screaming about it going away, I had 70% of my emails where I'm not buying you until I touch and feel your product.”
Competitors copied UNTUCKit's untucked shirt style for Spring 2019 campaigns
“Every single competitor, Vineyard Vines, J.Crew, Banana Republic, just go on. Everyone led their 2019 spring campaign with shirts meant to be worn on tuck.”
Riccobono: UNTUCKit will become a billion-dollar brand
“And the reason I say that is, I really believe that this is going to be a billion dollar brand. I still do.”
Riccobono: Kleiner Perkins advised UNTUCKit to fund growth with debt
“And I owned, by the way, a lot of the company, because we, when Kleiner put on eight million, they were very adamant, our main investor, to say, this company's doing well, do not dilute, like, let's just raise with debt. So we took on debt, because we had a pl…”
Riccobono: UNTUCKit achieved profitability across 2022, 2023, and 2024
“We are now profitable in 22, and we were significantly profitable in 23, even though the year wasn't what we wanted because we didn't market, and 24, we were profitable, and this year is an exciting year.”
DTC apparel brands must enter wholesale to reach billion-dollar scale
“You have to go into wholesale eventually. If you want to scale to that level to a billion dollar brand”
Riccobono plans to eventually sell or seek an acquisition for UNTUCKit
“Yeah, no, I will definitely want to get acquired or, and sell and kind of make this an ultimate. Now it's become, I need this now to get over this, you know, you don't want to be the person who's going to sell for something and then sell for nothing or sell. S…”