This episode is part lesson, part documentary to take a real look into where I’m spending my time as a CEO and the adjustments I’m actively making. There are constant challenges around setting the right priorities, and in this episode, I share what’s working, what isn’t, and where my head is at right now.

Here’s what I cover:

• Deciding whether to prioritize sales or product first
• Why business feels like a game of Settlers of Catan
• The value of having meeting-free days
• How I decide what to cut to stay focused

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Originally from Dubai and raised in Phoenix, Shaun studied Economics & History at Vanderbilt University.

While at Vanderbilt, and after leading United Nations linked projects like Imagine Land 2040, he co-founded Atlog, an AI voice agent for physical retail (starting with furniture) that handles customer service and collections calls.

In 2025, Atlog was accepted into Y Combinator’s first spring (“X25”) cohort; the team graduated right as Shaun was completing his degree at Vanderbilt.

Shaun is on a mission to bring helpful AI into real-world commerce and make technology serve outdated industries.

Shaun is only 22 years old.

Contact info:

Linkedin: https://www.linkedin.com/in/karakkattu/

Website: https://www.atlog.ai/

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Originally from New Jersey, Jake earned a B.A. in Economics (with a minor in Computer Science) from Vanderbilt University.

As COVID-19 shut the world down and his work environment changed, he saved up a six-month nest egg to go all-in on his startup, Pepper—a social-cooking app he co-founded with childhood friend in September 2021.

What began as a group-chat experiment sharing homemade meals has grown into a community of over 1 million home cooks worldwide, with Pepper featured on Fox’s Food Stars and At 27 years old, Jake was named to Forbes 30 Under 30.

He’s on a mission to improve cooking experiences by bringing social media–style engagement to real-world food sharing.

Jake is only 28 years old.

Contact info:

Website: https://www.peppertheapp.com/

Linkedin: https://www.linkedin.com/in/jakearonskind/

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Do you ever finish an interview and still wonder, “Should I hire them?”

I’ve been confident one moment, second-guessing the next.

In this episode, I walk through the 5-step process we now follow at To-Do Dudes to confidently choose the right team members. Starting from application and going all the way through their first week on the job.

You’ll learn:

• How to evaluate candidates before the interview starts
• Our exact 4-part interview structure
• Red flags to catch early
• What we watch for between interview and day one
• How training performance reveals everything

This process has helped us avoid costly mistakes and build a team that fits and stays.

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In this episode, I walk through the real-world framework I use to build and launch internal systems from scratch.

We’re covering:

• Defining the actual goal (and not doing too much at once)
• Creating without scope creep
• Testing before delegating
• How to document clearly
• Why delegation ≠ abdication

If you're building anything that involves people, process, or automation, this will save you time, energy, and a lot of rework.

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Andrew is an Ohio native and the founder of dcdx, a branding agency he went all‑in on in 2020 when his senior‑year internship at Vanderbilt was canceled.

In the five years since, he’s helped build magnetic, Gen Z‑focused brands for Spotify, Chipotle, Crocs, Eventbrite and more. He made Forbes 30 Under 30 honoree, was an Ad Age Gen Zers to Watch in 2025, and was even featured in FastCompany publication.

I got to interview Andrew after his recent launch of offline, a platform that brings social‑media branding into real‑world experiences.

He’s on a mission to make the future human, he’s redefining how brands connect with the next generation.

Andrew is just 26 years old.

Contact info:

Linkedin: https://www.linkedin.com/in/andrew-roth43/

Website: https://dcdx.co/

Website: https://www.offlinetalent.com/

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I finally did it! After nearly two months of late nights, caffeine runs, and endless tabs, our “holy grail” data sheet is live. In this episode, I pull back the curtain on how I wrestled scattered spreadsheets, CRMs, and support tickets into one single, living dashboard and the three “N”s that made it all click.

• Niching: I used to believe we had to be everything to everyone. But once we focused in on what actually moved the needle, it was clear that cutting services made us better, not worse. By niching, it reduces the training required, logistical complications, and gives you more time to focus on the true demand of the customer.
• Numbers: It’s like taking a blindfold off. For too long, we had been navigating by gut feeling. Now we finally have the system that can show what our CAC, LTGP, # of inquiries, # of new customers, and other important metrics.
• Nurturing: I’ll admit, I tried to hand this new system off to my team and walk away, but that completely flopped. I had been working on this system for over 200+ hours. Instead, I share the pivot I made using the “Document → Demonstrate → Duplicate” framework that helped the team get up to speed fast.

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In this episode, I share raw entrepreneurial reflections from memos I kept in April, May, and June. You’ll hear unfiltered thoughts on:

• How coffee has surprisingly affected me
• Choosing between logical and emotional decisions
• Why authoritarian leadership can diminish buy-in
• Pushing through moments when you’re on the verge of tears

Entrepreneurship is a rollercoaster. My hope is that these lessons, even if small, give a boost to those finding their way. Keep moving!

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