I listen to startup podcasts so you don’t have to.

How UNTUCKit Fixed Shirt Fit Forever

Strategy
June 27, 2025
Chris Riccobono shares how UNTUCKit became a fashion success after early failures.
Topics discussed in the episode:
-
What lessons can be learned from Untuckit's handling of near bankruptcy during COVID-19?
-
What strategies did Untuckit use to find its target market during marketing efforts?
-
How did Chris and Aaron manage roles for effective team leadership?
-
How can personal branding impact marketing effectiveness?
-
How did Untuckit handle distribution challenges during rapid growth?
-
What role did hiring play in improving Untuckit's product quality?
-
How important is timing in fundraising from venture capitalists?
-
How did Untuckit use unconventional marketing channels to accelerate growth?
-
Why is achieving consistent product quality crucial in product development?
-
How did identifying a personal problem lead to product-market fit for Untuckit?

What lessons can be learned from Untuckit's handling of near bankruptcy during COVID-19?

[Opening] During COVID-19, Untuckit faced financial crisis but managed to navigate it through tough decisions and negotiations. [Quote]

"We got on the phone with the bankruptcy attorney and he's like, you have to declare bankruptcy... We called our landlords, one by one, we called all of our factories."

[Takeaway]
  • Open communication with stakeholders can provide solutions.
  • Negotiation is critical during crises.
  • Resilience and adaptability are vital for survival.

What strategies did Untuckit use to find its target market during marketing efforts?

[Opening] Untuckit focused on specific demographics through targeted marketing channels to find its customers effectively. [Quote]

"We started there and by the way, then we went to Howard Stern very soon after that."

[Takeaway]
  • Identify where your target audience spends time.
  • Diversify marketing channels to reach broader audiences.
  • Invest in marketing that provides measurable returns.

How did Chris and Aaron manage roles for effective team leadership?

[Opening] Recognizing individual strengths, Chris transitioned Aaron to the CEO role to enhance leadership effectiveness. [Quote]

"I recognized that he had a better history to be a CEO... and I think it ended up being a great decision."

[Takeaway]
  • Assign roles based on strengths and experience.
  • Leadership transitions can benefit company growth.
  • Self-awareness improves team dynamics.

How can personal branding impact marketing effectiveness?

[Opening] Chris appearing in his own ads made the brand relatable but also attracted criticism, which amplified awareness. [Quote]

"It helps you... Everyone would pick their head up and say, What is this lunatic talking about?"

[Takeaway]
  • Personal branding can humanize a company.
  • Controversy can increase brand visibility.
  • Authenticity resonates with audiences.

How did Untuckit handle distribution challenges during rapid growth?

[Opening] As Untuckit grew, handling distribution became complex. Chris navigated these challenges by expanding into brick-and-mortar stores. [Quote]

"We opened 90 stores in I think 2.5 years."

[Takeaway]
  • Scaling requires adapting distribution strategies.
  • Physical retail can complement online sales.
  • Rapid expansion needs careful planning.

What role did hiring play in improving Untuckit's product quality?

[Opening] Hiring the right talent was pivotal for Untuckit. Bringing on experienced individuals helped solve critical product issues. [Quote]

"Bjorn walks in for a meeting... and he says, What do you think of the shirt, Bjorn? And Bjorn destroyed the shirt as the worst made shirt I've ever seen."

[Takeaway]
  • Experienced hires can offer valuable insights.
  • Constructive criticism leads to product improvement.
  • Hiring experts accelerates problem-solving.

How important is timing in fundraising from venture capitalists?

[Opening] Timing played a crucial role in Untuckit's fundraising efforts. Chris found it challenging initially but eventually secured investment at the right time. [Quote]

"Our first big fundraise was where we went out in 2016 to venture growth funds and, and Kleiner Perkins... We raised $8 million from them."

[Takeaway]
  • Fundraising success can depend on timing and company growth stage.
  • Perseverance is key when seeking investment.
  • Strategic investors can add significant value.

How did Untuckit use unconventional marketing channels to accelerate growth?

[Opening] Chris leveraged unconventional marketing channels like sports radio and airline magazines to reach his target audience effectively. [Quote]

"We got a market. We had 21 grand to spend in marketing and we called Boomer and Carton New York radio show, the only one we could afford."

[Takeaway]
  • Identify marketing channels that align with your target demographic.
  • Test and iterate marketing strategies on a small budget.
  • Unconventional channels can yield significant results.

Why is achieving consistent product quality crucial in product development?

[Opening] Ensuring consistent product quality was a major challenge for Chris. Quality issues could undermine the entire brand's promise. [Quote]

"When your name is untuckit, shirts not untuck, and you're talking about this perfect length, it has to be perfect."

[Takeaway]
  • Consistency in product quality is essential for customer trust.
  • Pay close attention to manufacturing processes.
  • A brand's promise must be upheld by its product.

How did identifying a personal problem lead to product-market fit for Untuckit?

[Opening] Identifying a common problem among men led Chris Riccobono to find product-market fit. He realized that shirts looked sloppy when worn untucked. [Quote]

"I asked my buddies, do you have this problem? Do you have this problem? And they all would light up and say they have the problem."

[Takeaway]
  • Recognize personal pain points that may be widespread.
  • Validate the problem with potential customers.
  • Building a product that solves a real issue can lead to strong product-market fit.