How I Built This with Guy Raz: Advice Line – What’s Your Value?

Date: March 19, 2026
Guests: Miguel McKelvey (WeWork), Alexa Hirschfeld (Paperless Post), Pete Maldonado & Rashid Ali (Chomps)
Host: Guy Raz
[Episode Link & Resources in Show Notes]

Episode Overview

In this Advice Line mashup, host Guy Raz and four returning founder guests tackle a common entrepreneurial challenge: How do you define and communicate your value proposition? Through real-time calls with three business owners—in sustainable gift wrap, dog enrichment cards, and premium pesto—the guests provide practical, actionable advice on product positioning, community-building, and scaling operations, offering insights that will resonate with founders of all kinds.

1. Shiki Wrap: Defining the Value in Sustainability and Experience

Guest Advisor: Miguel McKelvey, co-founder of WeWork
Caller: Megan Downey, founder of Shiki Wrap (Shelburne, Vermont)
Segment: 04:01 – 14:21

Key Discussion Points

• Product: Beautiful, reusable, zero-waste gift wrap and bags from sustainable, certified recycled fabrics.
• Challenge: How to scale education and excitement about a tactile, somewhat disruptive product—should she focus on retail, ecommerce, or in-person “gift wrap bar” demos?
• Sales Channels: Primarily online (own website, Nordstrom.com, Kickstarters). Bags are ready for retail as they require less explanation than wraps.

Notable Quotes & Moments

“We use certified fabric. There’s actually a lot of greenwashing in the recycled plastic space.”
– Megan Downey, 05:45

“If I buy one… then I give it as a gift, then what happens next?”
– Miguel McKelvey, expressing common customer confusion, 07:27

“Communities are the best customers rather than fragmented individuals… try to find those communities that this really appeals to.”
– Miguel McKelvey, 11:59

“I would think that if you were to focus your energy on that eight-week period [the holidays], it would be worthwhile to just throw it all in—and then focus on the retail stuff the rest of the year.”
– Guy Raz, strategic focus advice, 10:12

Insights

• In-person demos are powerful for tactile products—especially during the holidays when gift wrapping peaks.
• Use pop-ups to create dynamic content for digital channels (hire local college students to film, 10:51).
• Target niche communities (e.g., scrapbookers) who’ll “get it” and spread the word organically.
• Carefully consider timing and capacity before vertically integrating US manufacturing for patented wraps; be wary as investors may see this as risky for a small company (13:33).

2. Woofsie: Making Mental Enrichment for Dogs Instantly Understandable

Guest Advisor: Alexa Hirschfeld, co-founder of Paperless Post
Caller: Amanda, founder of Woofsie (Madison, Wisconsin)
Segment: 19:26 – 29:34

Key Discussion Points

• Product: A deck of 52 cards with guided enrichment activities for dogs (QR codes link to demo videos).
• Challenge: The product’s purpose is unclear online—customers mistake it for novelty dog card games, not understanding its value for dog behavior and mental health.

Notable Quotes & Moments

“People see it and they’re like, oh, my dog’s going to play a card game. It’s like, well, no…”
– Amanda, on customer confusion, 23:06

“The best way I’ve found to position your product is to really understand what your most beloved fans see in it… that’s the crux of the positioning.”
– Alexa Hirschfeld, 24:48

“Could you kind of flip the script and literally say something like, in 10 minutes a day, reduce boredom and anxiety and destructive behavior?”
– Guy Raz, on focusing marketing copy on customer problem/solution, 25:42

Insights

• Use customer testimonials with specific, relatable benefits to create trust and clarity.
• Frame messaging around solving top-3 pain points for dog owners: Boredom, anxiety, and destructive behavior (“10 minutes a day to a calmer dog”).
• Test different positioning statements online; see what resonates and iterate.
• Solicit customer videos and stories for rich, authentic social proof (contest idea, 29:08).
• Book recommendation: April Dunford’s “Obviously Awesome” for developing product positioning (27:00).

3. In Mark’s Kitchen: Balancing Artisanship and Scalability in Premium Grocery

Guest Advisors: Pete Maldonado & Rashid Ali, co-founders of Chomps
Caller: Mark Goldfarb, creator of an artisanal pesto brand (Woodstock, NY)
Segment: 33:05 – 44:00

Key Discussion Points

• Product: Top-shelf pesto (basil, arugula, dandelion, ramp; vegan options) made with high-quality ingredients in small batches, sold refrigerated in glass jars ($16.99–$22).
• Challenge: With 25% annual growth but a “company of one,” Mark seeks advice on finding the right person to help him scale effectively, without compromising quality.

Notable Quotes & Moments

“We started in a school bus that we lived in for seven years and built it to a seven-figure business… Now I run three businesses.”
– Mark Goldfarb, 33:50

“Extreme self-awareness… Pete’s ops and finance, I’m sales and marketing. Think about what gaps you have that they need to fill.”
– Pete Maldonado, on co-founder roles, 36:58

“Where are you spending your time? What is tactical versus strategic? You can leverage third parties—even for things like picking up basil.”
– Rashid Ali, on prioritizing founder time, 39:01

“If you’re not looking for big-box growth, consider hiring someone younger, with energy, who’s passionate about the product—even a recent MBA grad.”
– Guy Raz, on non-traditional hiring for values-aligned growth, 42:26

Insights

• Self-analyze your strengths and hire for complementary skills (sales/marketing vs. ops/finance).
• Offload tactical chores (like driving for supplies) to focus energy on strategy and growth.
• Determine if you want an operator for scale or an apprentice-type team member to help in specialized retail—this defines your hiring/search strategy.
• Maintain brand ethos: If ingredient quality is non-negotiable, be clear about scale limitations and the types of hires suitable for your company.
• Leverage existing fans as candidates—they already love the brand.
• Practical search advice: Start with word of mouth, LinkedIn, targeting business graduates interested in CPG/specialty foods.

Notable Cross-Episode Themes

• Tactile and Disruptive Products Need In-Person or Visual Demos: Both Shiki Wrap and Woofsie discovered that customers “got it” after seeing/feeling/experiencing the product—and that online communication must reflect these demos.
• Community-Driven Growth: Identify and empower niche audiences—they amplify your message more effectively than fragmented individuals.
• Hiring & Scaling: For artisan/mission-led brands, the first hire (or partner) should align with your skills gaps and long-term vision—even if it means hiring for passion and trainability over big-brand experience.
• Clear Messaging: Position your product through the lens of the customer’s problem, not just features.

Key Timestamps

• Gift Wrap Value & Channel Dilemma (Shiki Wrap) – 04:01–14:21
• Defining Positioning & Clear Messaging (Woofsie) – 19:26–29:34
• Artisanship, Scaling, and the Right Hire (In Mark’s Kitchen) – 33:05–44:00

Memorable Quotes (with Timestamps)

• “Communities are the best customers rather than fragmented individuals.”
  – Miguel McKelvey, 11:59

• “Flip the script… in 10 minutes a day, reduce boredom and anxiety.”
  – Guy Raz, 25:42

• “Extreme self-awareness… think about what gaps you have that they need to fill.”
  – Pete Maldonado, 36:58

Tone and Language

The tone throughout is conversational, supportive, and practical. The advice is delivered in a spirit of camaraderie—entrepreneurs helping entrepreneurs—with encouragement and realism about the difficulties of brand-building, focus, and scaling.

Final Takeaways

• Show, don’t tell—especially with innovative products. Consider creating content that captures the product in action.
• Lean on customer insights to craft your core message. Let your biggest fans articulate your value.
• Clarify your goals and values before hiring. The right first addition to your team will be aligned with both your needs and your vision for the business.
• Be strategic with your time and energy, focusing on high-leverage activities and delegating the rest.
• Find and fuel your community—they often become your best marketers and, sometimes, your best hires.

For more episodes and detailed founder stories, visit How I Built This on Wondery.