Feb 5, 2026 · 46m · how-i-built-this
Advice Line with Jon Stein of Betterment
Guy Raz · 14m spoken Jon Stein · 13m spoken Maggie McDonald · 4m spoken Mike Smith · 4m spoken Dan Criss · 4m spoken
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Advice Line, Guy Raz and Betterment founder Jon Stein mentor early-stage entrepreneurs on resolving growth bottlenecks, managing distribution channels, and leveraging pricing power. Drawing on historical business lessons and Betterment's founding journey, the hosts deliver actionable strategies for scaling sustainably in uncertain markets.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 34.4% of the talking time here. How this is scored →
Guy as informed peer 6.3 Guest teaching 2.7 Guest disagreement 1.0 Guy pushing back 1.4
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 26:40 Pushing back against taking on growth debt
In a universally collaborative episode, Jon Stein directly challenges Mike's premise of taking on debt for shop expansion, warning him about insolvency risks based on his family's business history.
Hardest push from Guy ▶ 29:40 Guy firmly urges raising prices on custom workGuy firmly steers Mike away from underpricing his labor, insisting that with rising material costs and tight capacity, raising rates is imperative.
Biggest teaching moment ▶ 7:25 Dan Criss explains guayusa blending mechanicsDan Criss educates Guy and Jon on the specific botanical and digestive properties of guayusa versus yerba mate to overcome consumer bitterness.
Guy holds their own ▶ 14:15 Guy Raz maps Liquid Death community playbookGuy leverages his deep repository of startup brand case studies to outline a community building and email capture playbook modeled on Liquid Death.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Welcoming Jon Stein and Betterment's Growth Journey | 6 | 3 | 1 | 1 | Guy introduces Jon Stein, recapping Betterment's origins in 2008 and current scale before discussing Stein's new financial advisor directory venture. Stein elaborates on the discovery problem in wealth management, and the interaction is completely collaborative and collegial. | |
| Entrepreneurial Opportunities in Uncertain Economic Climates | 6 | 2 | 1 | 1 | Guy questions how founders should evaluate launching during uncertain macroeconomic conditions, referencing historical parallels like 1929. Stein shares family archival reflections and historical perspective on resilient business creation during downturns. | |
| Caller Dan Criss on Prioritizing Growth Channels for Heretic Yerba | 6 | 4 | 1 | 1 | Caller Dan Criss describes Heretic Yerba, explaining yerba mate and guayusa blending to overcome bitterness. Guy and Jon validate his product background and air traffic control transition while probing current revenues and multi-channel dilemmas. | |
| Strategic Sequencing and Brand Positioning for Heretic Yerba | 7 | 3 | 1 | 2 | Jon Stein draws on his time in Uruguay and recommends sequencing channels rather than spreading resources across wholesale, loose leaf, and cans simultaneously. Guy provides tactical branding advice, comparing Heretic's potential cult branding to Liquid Death. | |
| Cultural Adaptations of Yerba Mate and Break Transition | 5 | 3 | 1 | 1 | Guy and Jon debrief Dan's call with personal anecdotes about drinking mate in South America before welcoming Mike Smith of MTS Woodworking. Mike explains building custom furniture out of his small basement shop. | |
| Advising MTS Woodworking on Pricing Power and Low-Risk Scaling | 8 | 2 | 1 | 3 | Mike asks about taking on debt to expand workshop space, but Jon warns against leverage using the story of his family's company Harden Furniture. Guy strongly advises Mike to raise prices and standardise product dimensions rather than over-committing to high-risk expansion. | |
| Custom Craftsmanship Dynamics and Break Transition | 6 | 2 | 1 | 1 | Guy and Jon reflect on regional pricing differences and market dynamics for custom craftsmen before introducing caller Maggie McDonald of Floofball. Maggie describes her soccer-themed dog kit parody products. | |
| Channel Strategy and Brand Integration for Floofball | 7 | 3 | 1 | 2 | Maggie asks about rising direct-to-consumer costs and scaling wholesale, Chewy, and club partnerships. Jon details Betterment's shift to B2B channels to overcome consumer acquisition caps while Guy and Jon brainstorm Chewy pack-ins and community retention. | |
| Jon Stein on Finding Product-Market Fit and Archival Reflection | 6 | 2 | 1 | 1 | Guy asks Jon to reflect on the core lesson from his founding journey, prompting Jon to emphasize the difficulty and value of product-market fit. An archival clip from Jon's 2018 interview illustrates the sleepless preparation before pitching Betterment. |
Statements from this episode (12)
Betterment Manages Over $60 Billion for More Than One Million Americans
“That's right. Even, even more than that today. And we manage money for over a million Americans.”
Stein: Financial Advisor Discovery Still Runs on Referrals, Not Data
“Today, financial advisor discovery
Still runs on referrals, not data.”
Heretic Yerba Expects $60K in Sales This Year, Doubling Next Year
“This year we'll probably do about 60,000, about double what we did last year and expected to double that again next year.”
Founders Should Master One Growth Channel at a Time Before Expanding
“I've seen firsthand at Betterment and at other companies that I've advised over the years, how too many simultaneous growth paths can dilute focus, even if they're all promising and maybe they're all things you want to do in the long run. I think that you can …”
Harden Furniture Was Once America's Largest Family-Owned Furniture Company
“And that became this company, Hardin Furniture, which at a time was the largest family owned furniture company in America.”
Harden Furniture Went Bankrupt Due to Debt and Foreign Competition
“The company doesn't exist anymore. My family furniture company, partly because they took on debt and partly it was due to foreign competition. But ultimately, you know, went, went under they couldn't service the debt payments.”
Craft Businesses Must Target 80% Profit Margins to Safely Fund Expansion
“A general rule of thumb that I'd love to see is, is 80% might be profit. 20% might be cost of goods, right? So if you think about what you'd have to do to your prices to get there, then you would have room to rent space and hire people and expand confidently.”
Rising Import Costs Will Allow Custom Woodworkers to Profitably Raise Prices
“The prices of goods from abroad are going up. So I'm optimistic that Mike's going to be able to raise his prices and find a path.”
Floofball Expects $75,000 in Annual Sales Across Four Different Channels
“So right now we're in four different channels. We're in direct-to-consumer, we're in wholesale, we're on Chewy, and we're starting to explore some professional club partnerships as well. So this year we're expecting to end the year at 75 K.”
Direct-to-Consumer Marketing Is Now Too Expensive for Rapid Scaling
“Direct-to-consumer marketing is becoming very expensive, and therefore it's become a lot slower to scale than I had originally anticipated.”
Chewy Sells More Pet Supplies in the United States Than Amazon
“I think it's the biggest distributor of pet supplies. I think it's bigger than Amazon when it comes to pet supplies in the U.S.”
B2B Sales Provide Repeatable Scaling When D2C Marketing Efficiency Caps Out
“Focus doesn't mean exclusivity. So we still market direct to consumer at Betterment. That's a lot of the brand origin story. That's where we came from. It's, and we built around that customer. But our marketing dollars, there's only so many dollars we can spen…”