How I Built This with Guy Raz

Advice Line with Serial Entrepreneur Mark Cuban
Episode Date: January 29, 2026

Episode Overview

In this Advice Line special, host Guy Raz is joined by serial entrepreneur and Shark Tank investor Mark Cuban to field real-world business questions from startup founders. The episode oscillates between foundational business wisdom and targeted advice for callers representing emerging CPG, skincare, luxury goods, and apparel brands. Throughout, Cuban emphasizes the importance of operational discipline, margin focus, prudent growth, and leveraging AI and technology for entrepreneurs at any stage.

Key Segments, Discussion Points & Insights

[03:07] Mark Cuban’s Career & Mission-Driven Entrepreneurship

• Mark talks about his latest venture, Cost Plus Drugs, which aims to make prescription medication more affordable and accessible in the U.S.
• Cuban highlights how automation and robotics in manufacturing can disrupt the pharmaceutical industry by enabling agile production with efficiency and cost savings.
• However, FDA fees are cited as a significant barrier to scaling domestic drug production:
  • “If you want to do it for 100 drugs, that's $36.5 million...that is what ruins the margins here in the United States.” (05:27)

Notable Quotes

• Mark Cuban [07:17]:
  “Everybody hates the economic side of their healthcare. Everybody. I want to fix that...having that as a mission, I mean, to me it's fun. It fills my competitive juices, it keeps me motivated.”

Caller 1: Lucy, CEO of One Trick Pony Peanut Butter

(Segment: 08:13 – 18:16)

Business Overview

• Family-founded, two-ingredient organic peanut butter in innovative upside-down jars to counteract oil separation.
• Recently launched the new jar design; sales on track for $1 million this year.

Main Challenge

• Expanding from natural retail channels into big box retailers without losing brand premium position and margin.

Mark Cuban’s Advice

• Don’t chase sales at the expense of profitability:
  “The biggest mistake startups make is chasing sales over margin dollars and profits.” (13:02)
• Weigh slotting/st ocking fees and promotional costs – only expand when the unit economics and budget allow.
• E-commerce can be more profitable; consider doubling down on direct sales and influencer marketing rather than large-scale retail.
• Caution about VC pressure vs. founder control:
  “If you can't get the return on the capital you already have in the bank, then you're going to have to raise more money, which is going to take you under 50%...that's really bad news...ignore your VC no matter what they say.” (14:57)
• Design suggestion: try a clear or “peekaboo” jar variant for added shelf appeal:
  “Anything that differentiates you even a little bit to get attention on the shelf without costing you too much.” (17:21)

Actionable Takeaways

• Grow at your own pace; prioritize cash flow and loyal user base over volume or rapid retail expansion.
• Balance premium branding with channel strategy – you’re competing with other premium brands, not mass-market.

Caller 2: Macy Schmidt, CEO of Girlish Skincare

(Segment: 19:18 – 28:02)

Business Overview

• Startup skincare brand focused on “youth-safe” products for teens and tweens.
• Launched in May, targeting parents (the buyers) and young users (the consumers), with $25,000 sales in their first year.

Main Challenge

• Marketing conundrum: allocate budget to reach parents (the purchasers) or their children (the users)?

Mark Cuban’s Advice

• Early-stage focus: Stay lean, prioritize direct, local sales (“flea markets”/events) where user education and demonstration is possible.
• Marketing to parents over kids:
  “Your whole sales pitch is education and your education is really a fear based education. You're steering the heck out of a parent for the most part. Because kids are fearless at that age.” (22:27)
• Don’t overspend on digital ads until you have strong cash flow and repeat customers; test small, maximize local and low-cost channels.
• Build email lists and analyze repurchase rates before investing heavily in broader paid marketing.
• Constantly iterate based on customer feedback and “use the gift of time” to learn before ramping up spend.

Notable Quote

• Mark Cuban [27:17]:
  “You want to do things that put cash in the bank, where you can control your own destiny as much as possible...build up those repetitive sales.”

Caller 3: Dan Jansen, Owner/Maker of Imperium Shaving (soon to be Dan Jansen Razors)

(Segment: 29:15 – 39:39)

Business Overview

• Handcrafted luxury razors pairing with standard blades. Once a $50k/month business pre-pandemic, now solo and rebuilding in a new city (Raleigh, NC).

Main Challenge

• As a solo founder, how to prioritize for growth and scale without a team.

Mark Cuban’s Advice

• Radically raise prices:
  “You’re not selling razors, you're selling Dan. You're selling your creativity...as with any piece of artwork, the more expensive it is, the better the perception.” (33:59 - 34:15)
• Rebrand the business under your own name for artisan cachet (e.g., Dan Jansen Custom Razors).
• Offer ultra-premium, bespoke products (e.g., $3,000 razors, as art/gifts), market the artist story.
• Pitch to local golf clubs, hotels, and corporate gifts; target local media, podcasts, and morning TV for exposure.
• “If you have high enough margins and know your customer base...all you gotta do is sell one.” (35:46)

Actionable Takeaways

• Leverage your personal story and creative process in all branding.
• Think corporate gifts, resort gift shops, and local TV as starting points.
• Reintroduce yourself to your new city and market as an “original,” premium artisan.

Caller 4: Kristin Rood, Founder/CEO of Northern Classics

(Segment: 40:48 – 51:13)

Business Overview

• Children’s winter outerwear blending technical quality and timeless design; sales heavily seasonally skewed (~90% Sep–Jan), $1M/year in revenue.

Main Challenge

• Whether to expand into spring/summer lines for year-round revenue or double down on core winter products.

Mark Cuban’s Advice

• Address profitability and supply chain first:
  “If you're not profitable, you either have got to borrow money or go out there and raise money or put more of your own money in. And that's all risk capital.” (44:08)
• Tariffs on Chinese manufacturing are a huge margin killer; explore alternate suppliers, negotiate costs, and consider taking over sourcing key materials yourself.
• Use the off-season to “educate yourself in all the little details” – experiment with AI tools (ChatGPT, Gemini, Perplexity) for supply chain research and process improvement.
• Reiterate focus:
  “You need to start controlling your own destiny. And as boring as it can be, figuring all this stuff out, you've got to get to that because that's what's going to take you to the next level.” (49:40)

Guy Raz’s Suggestion

• Consider expanding through adjacent products before new seasons: base layers, boots, shoulder season jackets.

Additional Insights, Memorable Quotes & Moments

• General Philosophy (Mark Cuban):
  • “Don't chase sales, chase profitability...”
  • “Curiosity can be satisfied right out of your phone with AI. And I think that is the big differentiator. And it's such a democratizer for entrepreneurs for sure.” (53:34)
• On Technology for Entrepreneurs:
  • Cuban points out that with AI, “everybody has access to every library in the world...it's absolutely amazing.” (54:01–54:09)

Episode Timestamps & Key Moments

• 03:07 – Mark Cuban re-joins the show; discusses automation, robotics, and U.S. drug manufacturing barriers.
• 08:13 – One Trick Pony Peanut Butter: Lucy’s growth, retail challenge, and Cuban’s advice to prioritize margin over expansion.
• 19:18 – Girlish Skincare: Marketing to buyers vs. users, with deep discussion on customer education and cash flow discipline.
• 29:15 – Imperium Shaving: Post-pandemic struggles, pivoting to luxury custom branding, and selling yourself as an artisan.
• 40:48 – Northern Classics: Seasonality in DTC apparel, supply chain risk, and using downtime for operational learning.
• 52:27 – Mark Cuban on operational efficiency, inventory control, and leveraging technology for margin gains.
• 53:34–54:09 – Reflections on curiosity, learning, and AI as an entrepreneurial superpower.

Tone & Style

The conversation is warm, encouraging, and marked by Cuban’s trademark directness and pragmatism. Raz and Cuban blend empathetic listening with tough-love advice, staying focused on what matters for founders: building sustainably, learning relentlessly, and staying curious and adaptable.

Takeaway Summary for Entrepreneurs

• Always put margins and cash flow before top-line growth.
• Take your time expanding; don’t let external pressure force premature scaling.
• Leverage your story, creativity, and unique value—especially in artisanal or premium markets.
• Constantly scrutinize and negotiate your supply chain; control what you can.
• Use technology and AI to accelerate your learning and decision-making.
• Accept that learning cycles and operational refinement are as important as headline sales.

Mark Cuban, closing advice:
“Use every technological tool available to you...be curious because I think that was my greatest skill back then. I loved to learn then and now. But now curiosity can be satisfied right out of your phone with AI. And I think that is the big differentiator. And it's such a democratizer for entrepreneurs for sure.” (53:34)