Podcast Summary: How I Built This with Guy Raz

Episode: Advice Line with Jamie Siminoff of Ring

Release Date: August 21, 2025
Host: Guy Raz | Guest: Jamie Siminoff (Founder of Ring)
Format: Advice Line – founders call in for real-time business advice

Main Theme

In this lively “advice line” episode, Guy Raz teams up with Jamie Siminoff, the innovative founder of Ring, to field business questions from three aspiring entrepreneurs at critical crossroads. Siminoff draws from his journey—bootstrapping a hardware device from his garage to a billion-dollar Amazon acquisition—to provide candid, actionable mentorship. The episode is equal parts tactical advice, personal stories, and comedic banter, focusing on go-to-market strategies, product positioning, pricing, niching, and the emotional resilience required to endure the entrepreneurial journey.

Key Discussion Points & Insights

1. Jamie Siminoff’s Post-Ring Journey (04:34–05:31)

• Update: After leaving Amazon/Ring, Siminoff launched Honest Days Work, merged it with a public smart lock company, acquired another startup, and rebranded as "Door" (door.com), aiming to revolutionize property management.
• Insight: "In a lot of ways with these callers...I'm kind of back with them...back at square one." (05:30, Jamie)
  — Even serial entrepreneurs must start over and adapt.

2. Call #1: Victor "Vico" Hernandez, Founder of Ergo Flexdesk (06:09–17:23)

[Topic: Crowdfunding a High-Tech, Multi-Use Smart Desk]

• Vico’s Product: A patented, motorized, sit-stand desk with tilting capabilities (up to 70º), app/voice control, and remote mobility—targeting artists, office workers, and users with disabilities.
• Challenge: How to run a successful Kickstarter campaign and sharpen marketing for a product with multiple potential audiences.

Major Insights and Advice

• Finding a Niche:

  • Jamie: “What’s worrying me right now is that you have a lot of customers, but fringe on each one…The thing about Kickstarter is you need to get groups into it. Niches can be big—it doesn't mean they're small.” (09:00)
  • Focus efforts on a couple of well-delineated user communities versus everyone at once (e.g., drafters, people with limited mobility, gamers).

• Launch Strategy:

  • Work with influencers from different sectors, design custom demo units, and use raffles to build buzz (10:08).
  • Emphasize real, visually compelling features: app control, movement, voice, and especially accessibility/utility for users with disabilities.

• Go Viral on a Budget:

  • Guy: “I can imagine a video where…a couple people are carrying a really heavy desk…and then you come out like, the future is a desk that moves for you.” (13:05)
  • Jamie references viral launches by Liquid Death and Dollar Shave Club for inspiration: “It doesn't have to be outlandish…It can also be very emotional.” (14:08)

• Targeted Branding:

  • Jamie suggests sub-branding for different verticals (“Gamer Extreme Desk by Vico”, “Healthcare Desk by Vico”) to avoid confusing customers (15:08).

• Learn From Early Adopters:

  • Guy: “Once you put this out into the world, you’ll start to see where you’re getting traction and who’s interested…your consumers, they kind of show you the way.” (16:11)
  • Jamie: “That’s what’s so awesome about Kickstarter…you're getting money votes, and when people vote with their dollars, it’s very different.” (16:41)

Memorable Moments & Quotes

• On Product Focus:
  “The magic, a lot of times, comes from focusing it.” (11:59, Jamie)

• On Entrepreneurial Lessons:
  “I'm hoping there's one [niche] that's big enough to be a business, because if you have to do multiple to be a business, I really worry...” (15:43, Jamie)

• [Fun] Guy’s Elevator Pitch Idea:
  “The future is a desk that moves for you and that you can stand and sit.” (13:05, Guy)

3. Call #2: Ian (Ikenlabi Oladimeji), Founder of Lu G’s Chocolate (22:27–36:43)

[Topic: Premium, Ethically Sourced Nigerian Chocolate—Balancing Pricing, Impact, and Brand]

• Ian’s Product: Nigerian-made chocolate bars with unique West African ingredients (e.g., "ginger with plantain chips," "spicy suya"), with a “buy one, plant one” social mission for cocoa farmers.
• Challenge: Finding the right pricing and messaging—how to remain accessible without sacrificing quality and ethics.

Major Insights and Advice

• Authenticity vs. Market Reality:

  • Jamie: “People buy Bullen Branch sheets because they're great sheets.” (28:22)
  • Guy: “I think your biggest value proposition is ginger plantain crunch—these really interesting, unique flavors…that’s what draws people in.” (27:57)

• Mission Matters, but Product Must Win:

  • Jamie: “There’s something about having true authenticity…but...the consumer…they're gonna like an interesting flavor of something, and that's probably gonna trump any sort of story.” (28:55)
  • Guy/Fair Trade Examples: Tony’s Chocolonely and Liquid Death succeeded with unique branding and fun, not just their ethical story.

• On Pricing & Scaling:

  • Ian’s dilemma: Chocolate currently sells for $10.50/bar (vs. $5 for Tony’s Chocolonely, $2 for Hershey’s). Wants to lower cost as he scales.
  • Jamie (on pricing strategy): “When we came out [with Ring], we were making them for more than we were selling them for. We priced it…knowing also that we had to get to volume…If you overcharge…you won't get there.” (34:13)
  • Importance of knowing if scaling will genuinely lower COGS (“If you 10x sales, does pricing really come down?”) (35:06)

• Elevate Premium Positioning:

  • Guy: “Show us that a little bit more…people really, once they can see what you’re paying for—it’s handcrafted, made from the best quality, we roast, we pick the best farmers…this is a different kind of chocolate that you’re consuming.” (31:35)

Memorable Quotes

• On Balancing Mission and Margin:
  “You're saying, ‘I'm doing all these premium things…’ [vs] ‘I want to be the cheapest chocolate in the world.’ These things feel so distant.” (29:24, Jamie)

• Brand Aspiration Advice:
  “I would take a page out of LVMH…what's amazing…is their margins are so high because it's brand, it's aspiration they're selling. But it's also quality.” (35:41, Guy)

4. Call #3: Francesca Thompson, Founder of Thrive 12 (39:12–52:15)

[Topic: Inclusive Classroom Posters—Certifications, Amazon Storefront, and Expansion]

• Francesca’s Product: Digital (soon physical) inspirational classroom posters centering diversity and representation, designed by a teacher for teachers.
• Challenge: Is it worthwhile to pursue Women/Minority-Owned Business certifications prior to launching a physical product storefront on Amazon?

Major Insights and Advice

• Understand Your Market:

  • Teachers regularly buy new classroom decorations, sometimes out-of-pocket; low-priced downloads are standard, but Francesca plans to sell physical posters for $15–$19 on Amazon.

• Beyond Schools:

  • Guy and Jamie encourage thinking bigger: Could offices, nonprofits, or parents use these inclusive, motivational designs?
  • Jamie: “Even just people buying it for their kid's rooms.” (44:49)
  • Jamie: “If you can…find people that have made it…make them the poster…a real person. There’s something about it that gives it authenticity.” (46:01)

• Certifications—When and Why:

  • Guy: “If [certification] is going to give you some advantage…my answer is, yeah, absolutely. But…if it’s expensive or really time-consuming, is it worth it at this stage?” (47:06)
  • Jamie: “Be tactical…if it’s going to return $1,000 and it costs $100, it’s worth it…if it’s $1,000 for a $100 return, it isn’t.” (48:36)

• Product Exposure:

  • Certification can yield benefits (e.g., Amazon promotion, bundling tools), but authenticity and product-market fit remain paramount.
  • Jamie: “I don't think a certification...the teacher's looking at your products is going to say, ‘Is this certified?’” (49:21)
  • Francesca shares the certification application is around $300—both agree that's reasonable if it unlocks additional benefits.

Memorable Quotes

• On Product Power:
  “As I’m thinking about it, I kinda love it. The drone one...I love how that resonates. It sparks.” (44:56, Jamie)

• On Representation:
  “Just to see something like that [a disabled student represented on a poster]…that just makes them feel really good about themselves.” (45:19, Francesca)

5. Jamie Siminoff on the “Tunnel” of Entrepreneurship (53:01–55:53)

Guy asks: "If you could go back to you in the garage, before you knew Ring would succeed, what would you tell yourself?"

• Jamie:
  “If I really knew…just keep your head down. It's gonna be okay. The hardest part of entrepreneurship is you don't know it's gonna be okay—because it might not be. That's also why it's good to work on products you care about, because at least then you spent some time on something that mattered. Sometimes you see a glimmer of light, but it’s rare to see the full light…you don’t know how long the tunnel is.” (53:50–54:42)

• On Reality:
  “You could keep your head down and work hard…and not get there. But…you end up with a higher chance of making it.” (54:54)

Notable Quotes & Memorable Moments

• “The magic a lot of times comes from focusing it.” (11:59, Jamie)
• “When people vote with their dollars [on Kickstarter], it’s very different than when they’re voting with a survey.” (16:41, Jamie)
• “You don't know how long the tunnel is…it could be one year, seven years, thirty years, it could be infinite.” (54:25, Jamie)
• “You don't become a billionaire just because you sell a company for a billion dollars…you don't get all of it.” (52:50, Jamie, on viral myths about his success)

Updates From The Founders (56:47)

• Vico's Ergo Flexdesk: Debuted at CES, the Consumer Electronics Show.
• Ian's Lu G's Chocolate: Sold out and prepping for a relaunch with refreshed branding and packaging.
• Francesca's Thrive 12: Launched her Amazon store just in time for the new school year.

Key Timestamps

• 03:44 — Jamie gives a post-Ring update
• 06:09 — Victor “Vico” Hernandez (Ergo Flexdesk) call begins
• 22:27 — Ian (Lu G’s Chocolate) call begins
• 39:12 — Francesca Thompson (Thrive 12) call begins
• 53:01 — Jamie’s advice to his younger self

Final Thoughts

This episode crackles with practical guidance and warmth. Siminoff’s humility—bearing wisdom from both triumphs and setbacks—sets a relatable example for callers and listeners. The stories demonstrate that while technical excellence and ethical missions matter, business fundamentals—focus, iteration, understanding your market, and storytelling—are the keys to progress, no matter how daunting the tunnel may seem.

“If you focus, keep your head down, work really hard, you will be led to where you need to be going.” (55:25, Guy Raz)

For Entrepreneurs:

• Find your focused niche, especially at launch.
• Lead with your product’s unique value; let mission be the heart but know what customers buy.
• Authenticity and storytelling matter, but you must “earn the sale” with real customer excitement.
• Take tactical advantage of certifications and programs—but only if the returns justify the investment.
• Above all: perseverance. The journey is long, uncertain, and unpredictable—but clarity, authenticity, and hustle light the way.

Listen to the full episode for deeper context, warmth, and humor!