How I Built This with Guy Raz: Advice Line with Jon Stein of Betterment

Date: February 5, 2026
Host: Guy Raz
Guest: Jon Stein, Founder & Chair of Betterment

Episode Overview

This special "Advice Line" episode of How I Built This Lab features Guy Raz in conversation with Jon Stein, founder and chair of Betterment. Together, they take live calls from small business founders seeking guidance on how to grow their ventures. The focus is on offering actionable advice about making tough strategic decisions, navigating growth constraints, and the realities of building a business in uncertain times.

Main Themes & Key Insights

• Navigating Uncertainty in Business
  Jon and Guy reflect on starting companies during economic downturns, emphasizing that opportunities often arise when others are most fearful.

  • “There's still markets for great ideas and great products.” – Jon Stein (06:53)

• The Power of Focus, Learning, and Sequencing Growth Paths
  Striking a balance between pursuing new opportunities and not spreading resources too thin is a recurring theme.

• Building Community and Brand Differentiation
  Several founders are encouraged to lean into brand messaging and community building as powerful tools for customer acquisition and retention.

• Scaling Up: Risks and Rewards
  Expanding too quickly or taking on debt can jeopardize a business. Multiple callers receive practical, risk-aware growth advice.

Notable Quotes

• “Pick one thing and go deep on it personally for a while… as the driving force behind this, I want you to be hands-on, on the channel that you are most passionate about.” – Jon Stein (14:37)
• “The easiest change you can make is to raise prices.” – Jon Stein (28:56)
• “Focus doesn't mean exclusivity… but our marketing dollars, there’s only so many we can spend efficiently in [D2C]. The only way to spend more and grow faster is through B2B [channels].” – Jon Stein (43:44)
• “Once you’ve got [product/market fit], lean in—and give yourself some grace that it’s going to take some time to find it. The unpredictable part is just talking to customers and figuring it out.” – Jon Stein (44:44)

Episode Structure & Timestamps

1. [00:00–03:59] Introduction and Catching Up With Jon Stein

• Host Guy Raz welcomes Jon Stein, recounts the Betterment story, and dives into Jon’s new venture—building a definitive directory for financial advisors to help people find better matches using data.
• Discussion about the importance of staying invested despite macroeconomic fears.

2. [07:08–18:20] Caller #1: Dan Criss of Heretic Yerba (Yerba Mate Business)

Segment Highlight:

• “You're not just selling mate, you're really reframing the category for an American consumer.” – Jon Stein (10:48)

Key Points:

• Dan describes his company, Heretic Yerba, which offers clean, natural caffeine products (loose leaf blends, energy drinks, concentrates).
• Main Dilemma: With several growth avenues (loose leaf, energy drinks, concentrate), how to decide what to focus on without losing momentum or spreading too thin.
• Jon’s Advice:
  • Identify which channel best teaches you about customers and offers fastest growth.
  • Prioritize and “sequence,” focusing deeply on one path before expanding (15:31).
  • Build community around the brand (reference to Liquid Death) and use in-store presence as customer acquisition for the DTC site (16:11).
  • Consider using physical retail as education and proof points, but maintain focus.
• Branding: Lean into “Question Your Caffeine” and position as a “cleaner caffeine” alternative.

3. [19:28–31:30] Caller #2: Mike Smith of MTS Woodworking (Custom Furniture)

Segment Highlight:

• “Are there ways for you to grow in the smallest way possible?” – Jon Stein (28:56)

Key Points:

• Mike is a solo craftsperson operating from his basement, wondering if he should take on debt to expand workplace capacity.
• Key Challenge: Space and capacity limit. Weighing expansion (home addition, larger house, commercial lease) versus paying off debt.
• Advice:
  • Only grow capacity if you have demand and try incremental/micro-expansion first.
  • Raise prices, focus on higher-margin custom work, and consider standardized designs for scale.
  • Avoid debt unless absolutely necessary; find alternative low-risk expansion (subletting space, part-time help).
• Cautionary Tale: Jon shares his family’s furniture company, which failed after overextending with debt.

4. [32:48–44:21] Caller #3: Maggie McDonald of Floof Ball (Soccer-Themed Dog Toys)

Segment Highlight:

• “Thinking about Chewy as marketing is a really interesting way to think about it.” – Jon Stein (41:05)

Key Points:

• Maggie’s company, Floof Ball, creates soccer-themed dog toys and accessories with clever, parody branding (e.g., “Liverpooch”).
• Main Question: As a young founder with four revenue channels (DTC, wholesale, Chewy, club partnerships), what channel deserves focus for scaling?
• Advice:
  • Examine which channel brings the most re-orders, signals of scale, and margin.
  • Wholesale and club partnerships look promising for scaling; DTC is more expensive due to high marketing costs.
  • Use big platforms like Chewy as both a channel and a marketing tool—focus on branding and customer connection in every package.
  • Jon: Prioritize scalable channels but keep a touchpoint with DTC for direct customer connection and brand-building.
• Encouraged Maggie to strengthen packaging and to use each channel to build brand loyalty and community.

5. [44:22–46:17] Jon Stein’s Reflections and Final Advice

• Jon shares the importance of patience in finding product-market fit and perseverance in continually talking to, learning from, and serving customers.
• “Lean in—and give yourself some grace that it’s going to take some time to find it… keep talking to customers.” – Jon Stein (45:31)

Memorable Moments

• Jon’s family history in furniture-making—a business that thrived and then failed because of overextending on debt (28:56), offering a poignant lesson about sustainable growth.
• The playful branding ideas with Floof Ball (“Barkzil,” “Liverpooch”), and Guy’s offhand joke:
  “For Everton fans, you could give them Liverpool treats to feed their dogs.” (44:02)
• Jon’s story about his anxiety preparing to launch Betterment and finding edits on his BlackBerry from every 30 minutes overnight, illustrating the unpredictable, nerve-wracking journey of building something new (45:48).

Conclusion

This “Advice Line” episode stands out for its honest, practical coaching in response to real founder dilemmas. Clear patterns emerge: double down on what’s working, avoid overextending, differentiate noticeably, and build community. The advice is grounded in both Jon Stein’s entrepreneurial history and the daily realities of growing a startup, making it an engaging resource for builders at any stage.