✍🏽 Landon’s Loop #144

This week’s newsletter is supported by 1440 & University of Chicago Graham School

What’s in the Loop:

🎙️ Chicago Futurist Vol. 5 with Charlotte Trecartin, Founder & CEO of CharCharms

📅 4 Events in Chicago This Week

🧠 Chicago’s Fastest Growing Media Company is Hiring

🧠 Join 1440 in Chicago

My friends at 1440 are hiring!

1440 is one of the largest independent US media companies that delivers fact-first knowledge to 4,500,000+ insatiably curious, affluent, highly intelligent readers (35% hold a graduate degree vs. ~10% of the US population)

Completely bootstrapped and profitable (>$1M in revenue per employee with a 27-person team)

They also take benefits seriously:

  • Well-above-market salaries, frequent raises, bonuses, and meaningful equity

  • 100% medical, dental, and vision for full families, plus 16 weeks of paid parental leave

  • 401(k) contributions and a $500 annual 529 contribution per child

  • $2,500 toward a preventive full-body scan

  • 12-week paid sabbatical after 5 years and a strict no-weekends culture

If you’re interested in joining 1440 to build the future of media, I’d be happy to connect you with 1440’s CEO.

🎙️ Chicago Futurist: Charlotte Trecartin, Founder & CEO of CharCharms

Charlotte Trecartin has built and scaled Gen Z accessory brands by spotting consumer trends early. She noticed growing demand around water bottle personalization, which led her to launch her first product CharCharms in her basement in the Chicago suburbs.

CharCharms now generates over $10 million in sales and is stocked by major retailers including Target and Walmart. Founder Charlotte has since appeared on Shark Tank, was named to Forbes 30 Under 30, and has emerged as a leading Gen Z voice on Bloomberg.

Here’s our conversation:

You turned a category many people dismiss into a profitable business making over $10M. What consumer behavior did you see early that others missed

CT: Technically, CharCharms launched before the hydration boom and the Stanley cup craze. I identified the shift early, spotting growing interest in hydration and recognizing Gen Z’s desire for personalization before it became mainstream.

By anticipating both the hydration boom and the charm trend, I was able to build CharCharms at the intersection of functional hydration and self-expression. Hydration was only the beginning, and we’re continuing to evolve the brand to bring that same sense of personalization into new categories.

Hiring a TikTok coach for $400 a month at the beginning of your journey was a very specific bet. It helped you build over 100,000 followers and owned distribution. What do founders still misunderstand about social growth

CT: When you consistently share social content for your business, people begin to recognize you as the face behind the brand. Investing in yourself on social media builds trust, and that trust translates into people buying what you’re selling. Audiences don’t just support small businesses, they support the people behind them. They want to connect with the story. They want to root for the underdog. When you create entertaining, engaging content, you can absolutely turn a side hustle into a powerhouse business.

There’s always upside in investing in the growth of your personal brand. As the business grew, my responsibilities expanded, so I made the strategic decision to step back from being the face of CharCharms and bring someone else into that role. She’s doing an incredible job, and I’m genuinely excited for our community to connect with a new personality who can show up fully for the brand.

CharCharms is sold in major retailers like Target and Walmart. Which metrics matter most to buyers in 2026

CT: Sales. Always sales. You can’t fake them, and they are the only metric that truly matters. When you can prove that your product sells through, you earn the ability to start and maintain relationships with major retailers. At the end of the day, large retailers will not invest in small businesses that can’t move product.

What does your product’s growth reveal about how Gen Z expresses identity through everyday objects

CT: Gen Z is all about personalization and self-expression. In a world where everything feels mass-produced and trend lifespans are getting shorter, they crave ways to make practical, everyday objects feel uniquely theirs. Gen Z consumers prefer to customize products to express themselves rather than just buy generic items, and many are even willing to pay more for personalized goods and experiences. I personally believe that CharCharms’ rapid growth highlights this generational shift: accessories like charms allow individuals to turn something as utilitarian as a water bottle into a canvas for identity.

What did your SharkTank experience teach you about how outsiders value consumer businesses

CT: To the outside world, Shark Tank functions as a seal of approval. It signals legitimacy, momentum, and “this brand is worth paying attention to.”

Behind the scenes, though, the business wasn’t suddenly better because we aired. The product, supply chain, margins, and customer demand were already there. Shark Tank didn’t create the business, it simply validated years of operational work that nobody sees.

After the episode aired, consumers and large retailers took us much more seriously, which unlocked more conversations, partnerships, and deal flow. But what I learned is that outsiders tend to value visibility and endorsements, while operators know that sustainable growth comes from sell-through, execution, and consistency long before the spotlight hits.

You’re building CharCharms in Chicago and now operate out of a 10,000 sq ft facility with an eight person team. How did being in Chicago shape how you run your business

CT: I’m from the suburbs of Chicago, and building my company here gave me a huge advantage early on. I spent the first three years growing CharCharms out of my dad’s basement, which allowed me to keep overhead extremely low and stay focused on execution. Chicago’s startup ecosystem played a big role in that phase of my journey.

Some of the first networking events I ever attended were Landon’s VC events, which marked the beginning of my involvement in the local founder community. I was also honored to pitch at the very first GenZ VC in Chicago, and the startup community at mHUB opened doors to mentorship, resources, and really important connections with other builders. Chicago is definitely a place where you can build something real, and so I’m grateful to have grown this company here.

Biggest lesson you’d share with a first-time founder

CT: Building out your dream company takes far longer than people expect. The product development alone can stretch across many months, and getting your products into the retail sales cycle can be a full year or more. Building out the right team takes trial and error. From one young operational founder/CEO to another, patience is key, actions compound over time, and if you’re truly in it for the long haul, then it will absolutely work out

🎓 Your Bridge to Graduate Study at Top Universities

The University of Chicago’s Graduate Student-at-Large (GSAL) bridge programs are designed for motivated professionals and recent graduates who want to build academic momentum, explore a new field, or prepare for competitive graduate programs—without committing to a full degree right away.

GSAL students enroll in UChicago graduate-level courses, work closely with a dedicated advisor, and use the experience to gain skills, clarify goals, and demonstrate academic readiness.

I don’t think I received that much academic support anywhere else

Marvin, GSAL alum, now at Stanford Law

GSAL alumni have gone on to master’s and doctoral programs across the humanities, social sciences, and biological sciences, as well as professional schools including law, medicine, public policy, and social work.

Learn More at the Info Session

Learn more about the Graduate Student-at-Large Programs during an online information session on February 18 at noon CT. This session will highlight how GSAL supports academic exploration and preparation for graduate study, with guidance from Esther Pandian-Riske, Director of GSAL Programs, and Seth Green, Dean of the Graham School.

📅 Who’s Hosting This Week

Investing Essentials: Value Creation in Uncertain Times

v0 - Prompt to Production Studio Build Session

Second City GenJam: AI Video Workshop - Learn & Create AI Videos

AI, Storytelling & the Future of Visual Worlds

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👋 See you next week!

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