How I Built This with Guy Raz
Advice Line with Scott Tannen of Boll & Branch and Jamie Siminoff of Ring
Date: December 11, 2025
Guests: Scott Tannen (Boll & Branch), Jamie Siminoff (Ring)
Host: Guy Raz
Episode Overview
In this "Advice Line" installment, Guy Raz brings together two founders—Scott Tannen (Boll & Branch) and Jamie Siminoff (Ring)—who share decades of entrepreneurial experience and a unique bond as high school classmates. Listeners call in with real-world business challenges, and the pair give candid, practical advice rooted in their own journeys. Topics touch on scaling responsibly, balancing bootstrapping versus external capital, finding product-market fit, and marketing strategy. The episode's tone is casual, energetic, and often humorous, with moments of genuine insight and camaraderie between the guests.
Key Discussion Points and Insights
1. Reconnecting Old Friends & Shared Origin Stories
- [02:08–04:50] Scott and Jamie reminisce about high school, driving to school together, and the improbability of both achieving entrepreneurial success.
- Scott Tannen: “Jamie actually drove me to school, so I’ve been riding his coattails ever since.” [03:39]
- Jamie Siminoff: “The class was like 60 kids. ... One is a hugely successful sheets guy. It’s incredible.” [03:44]
- Emphasize how their paths, though different (sheets vs. security tech), show the unpredictability of entrepreneurial journeys.
2. Business Updates from the Founders
-
Jamie Siminoff (Ring):
- Back at the helm of Ring and excited about new AI-driven features for community safety.
- Example: Ring's "Search Party" AI helps neighbors find lost pets, leveraging Ring’s camera network.
- “We get over 1 million people tell us that their pet is missing ... we look on AI through the neighborhood ... and you can now put people together to actually find pets in neighborhoods.” [06:02–06:34]
- Focus is on inventing and earning trust, not just chasing competitors.
-
Scott Tannen (Boll & Branch):
- Growing the retail footprint, opening seven stores with seven more planned.
- Expansion is mainly east of the Rockies but planning to go national by 2027.
- Stresses the importance of maintaining brand values and vision through growth.
Caller 1: Melita Cyril – Q for Quinn (Organic Socks & Undergarments)
[08:05–17:24]
- Background: Melita runs Q for Quinn (organic socks and underwear), bootstrapped and profitable, now in mid-seven figures revenue. She and her husband run the business, their sole family income.
- Dilemma: Should they continue bootstrapping or bring on strategic investors for faster growth?
- Advice & Insights:
- Scott Tannen:
- Bootstrapping best preserves your vision. Taking outside capital shifts your primary obligation towards investor returns and can bring pressure to compromise on values (e.g., using cheaper materials).
- Quote: “As soon as you take money from an investor, your number one goal moves from whatever it is today to providing a shareholder return.” [11:13–12:17]
- Jamie Siminoff:
- Taking any outside money—no matter the amount—represents a major change. Carefully weigh whether the trade-off in control and pace is worth it.
- Quote: “That first dollar you take is a big step, no matter how many dollars it is ... If you take a million dollars, you’re really taking ten million because you gotta give ten million back.” [12:40–13:50]
- Expansion Thoughts: Melita’s move into athleisure, especially natural-fiber sports bras, taps into a market with rising demand for non-synthetic, chemical-free clothing.
- Jamie and Scott praise her mission, caution not to lose her “why” in pursuit of speed.
- Memorable Moment: Jamie jokes about sending Melita his resume given her success: “I’m going to send you my resume.” [10:20]
- Scott Tannen:
Caller 2: Eric Alexson – L Cubed Lifestyle (UV-Protective Apparel)
[22:53–32:18]
- Background: Eric is co-founder of a Florida-based brand using 100% polyamide fabric for comfortable, performance-focused, true UV-protective activewear. Bootstrapping and recently expanded onto Amazon and wholesaling to tournaments/events.
- Dilemma: Should they divide their focus between retail and wholesale/co-branded sales, or concentrate on one?
- Advice & Insights:
- Scott Tannen:
- Margin protection is critical—“Education eats margins.” Educating consumers on why they need this product is difficult and expensive.
- Quote: “Education eats margins. And when you’re the first one to do it, you’ve gotta bear that cost.” [26:10–27:17]
- Jamie Siminoff:
- Looks for the “pre-awareness” hook: people already understand sunscreen but don’t realize a shirt can protect like sunscreen.
- Breakthrough Thought: Sell shirts as “mechanical sunscreen”—package them inside a sunscreen bottle, place them in the sunscreen aisle to cue shoppers.
- Quote: “I’d be making sunscreen bottles with the shirt inside, and selling it where sunscreen is. ... I'd be selling the whole thing, 50 SPF, whatever. In the sunscreen aisle. In the bottle.” [28:55–29:15]
- Category Positioning: The enemy isn’t other brands, but sunscreen itself. Compete directly against chemical sunblock—not just other apparel.
- Memorable Quote:
- “Now you have an enemy—your enemy is sunscreen. Go chase them in every channel they play.” — Scott Tannen [31:37–31:49]
- “Retail loves something new in an aisle ... This is catnip.” — Jamie Siminoff [31:52–32:08]
- Scott Tannen:
Caller 3: Chris McElroy – NOCS Provisions (Modern Binoculars)
[35:44–47:10]
- Background: Chris’s company makes stylish, compact, waterproof binoculars and monoculars in bright colors, moving beyond the traditional “hunting” look. Bootstrapped growth, now stocked in REI, Dick’s Sporting Goods, and overseas.
- Dilemma: How to expand use/awareness of binoculars beyond core outdoors markets (birding, hunting) to events, music festivals, sports, city use?
- Advice & Insights:
- Jamie Siminoff:
- Think about how products can “attach to the phone”—people want to capture moments for social media.
- Consider accessories or app integration allowing phones to capture what binoculars see, increasing shareability and engagement.
- Quote: “People don’t go to these things anymore, most of them ... they go to capture the photo, not to see it themselves. Binoculars are for you.” [42:30–43:18]
- Scott Tannen:
- Suggests “depositioning” the rest of the binocular category—make NOCS the fun, approachable accessory for non-hunters, stadium-goers, or festival crowds.
- Appeal to “those who don’t want to be the person at the stadium in camouflage binoculars.”
- Guy Raz:
- Sees an opportunity in the “analog experience” trend—position binoculars as tools for unplugging, being present, and seeing the world without screens.
- Quote: “I actually think your biggest competition is distraction ... there’s an opportunity to lean into this kind of screen-free, decompress kind of thing.” [43:18–44:26]
- Memorable Moment:
- The trio jokes about combining their advice—integrating digital sharing for the masses but still serving the analog enthusiasts. “After selling to the 10 people Guy’s talking about, then you gotta go to my market.” — Jamie [45:02]
- Jamie Siminoff:
Rapid Advice – Founder Wisdom
[47:51–48:39]
- Guy Raz: Asks Scott for advice to his younger founder self.
- Scott Tannen:
- “Keep it simple ... what makes [businesses] successful at their core is not that complicated. The less you stray from the simplicity of that, the better.” [48:10–48:39]
Notable Quotes & Moments (w/ Timestamps)
- Jamie Siminoff on controlling your destiny:
“That first dollar you take is a big step, no matter how many dollars it is ... times it by five or 10, because that’s what they want back.” [12:40] - Scott Tannen on business trajectory:
“Bootstrapping is always going to be the way that it’s best to protect that vision.” [11:13] - Jamie’s Sunscreen-Inspired Idea:
“I’d be making sunscreen bottles with the shirt inside ... In the sunscreen aisle.” [28:55] - Scott on strategic focus:
“You now have an enemy, right? Your enemy is sunscreen.” [31:45] - Guy Raz on habits:
“I think your biggest competition is distraction ... put away the phone, take a walk, go outside, look up.” [43:18] - Jamie on business pivots:
“People don’t go to these things anymore, most of them ... they go to capture the photo, not to see it themselves. Binoculars are for you.” [43:06]
Timestamps for Important Segments
- [02:08] — Episode opening and guests’ reunion story
- [05:11] — Jamie’s update on Ring, AI features, and strategy
- [07:07] — Scott’s Boll & Branch retail growth update
- [08:05] — Caller 1: Melita (Q for Quinn): Scaling and bootstrapping dilemma
- [11:09] — Advice on external investment, protecting brand vision
- [13:50] — Expansion into athleisure and market opportunity for natural fibers
- [22:53] — Caller 2: Eric (L Cubed Lifestyle): UV apparel, retail vs. wholesale
- [26:10] — Margins and educational marketing challenges
- [28:55] — Sunscreen-aisle innovation & category reframing
- [35:44] — Caller 3: Chris (NOCS Provisions): Binoculars outside of outdoor core
- [42:30] — Integrating with digital/social habits, analog ritual possibilities
- [48:10] — Scott’s advice to past self: Simplicity and focus
Tone & Dynamic
The episode features friendly banter and humility between the hosts and guests, with lots of self-deprecating humor (“I’m more a Denny’s guy than Wagyu”), analogies to their own experiences, and concrete, actionable advice. The conversation fluidly blends inspiration, tactical business insights, and an honest look at entrepreneurship’s risks and rewards.
Summary Takeaways
- Scaling a mission-driven brand requires discipline; outside investment brings pressure and potential compromise.
- Radical, category-redefining marketing (like "mechanical sunscreen") requires framing your competition and leveraging existing consumer behavior.
- For hardware/lifestyle expansion, success often lies in either seamlessly aligning with digital habits or tapping into desire for analog, present experiences.
- Keep business strategies simple and focused on core value to customers, especially under pressure.
- Entrepreneurial success rarely follows a straight line—resilience, iteration, and vision are recurring themes.
[End of Episode Summary]