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How I Built This with Guy Raz

Advice Line with Niraj Shah of Wayfair

with Neeraj Shah, Valerie Zweig, Bree Van Leeuwen, Tess Milholland

Published October 30, 2025
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About This Episode

In this Advice Line episode of How I Built This Lab, host Guy Raz and Wayfair co-founder and CEO Neeraj Shah take calls from three founders seeking help with branding, financing, and career-risk decisions. They discuss how to clearly communicate a novel cooking ingredient (CookStix), when and how to seek funding for a mineral sunscreen brand (Daily Shade), and how a founder of a solo-women-travel housing app (HerHouse) should think about leaving a well-paid job. Neeraj also reflects on his long co-founder relationship, Wayfair's scale and focus strategy, and the non-linear nature of entrepreneurial journeys.

Topics Covered

Entrepreneurship Co-founder relationships Branding and naming Marketing and customer education Small business financing Side hustles Work ethic Travel and tourism Online safety Women's health advocacy

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Quick Takeaways

  • When a product format is truly new, simple and literal packaging and messaging often work better than clever taglines or imagery.
  • Educating consumers on how to use an innovative product can require repeatedly and explicitly comparing it to the incumbent format (e.g., "one stick equals one box of stock").
  • For product-based businesses, purchase-order financing and retailer test orders can provide growth capital without immediately giving up equity.
  • Convertible notes can let founders raise early capital without having to fix a valuation too soon, while still rewarding early investors with a discount later.
  • Bootstrapping as long as possible can give founders more control, but outside money makes sense once there is a clear, high-return use that cannot be funded from cash flow.
  • Founders juggling a demanding job, a startup, and family responsibilities may benefit from intermediate steps like hiring part-time help or negotiating reduced hours before quitting.
  • Strong co-founder relationships often hinge on complementary strengths and deep mutual trust in each other's business judgment.
  • Wayfair pairs large-scale resources in tech, logistics, and marketing with a startup-like mentality and a narrow focus on home goods to stay competitive.
  • Physical retail can extend a digital brand by letting customers experience a full product range, get in-person design help, and access services like financing.
  • Entrepreneurial paths are rarely linear, so choosing work you enjoy and learning from setbacks is crucial for enduring the long journey.

Podcast Notes

Advice Line format and introduction with Neeraj Shah

Explanation of the Advice Line concept

Guy Raz introduces the Advice Line as a place to help solve business challenges[2:57]
• He notes that each week he is joined by a legendary founder, a former guest on the show, to help answer listener questions
Call for listener participation[3:06]
• Guy gives the phone number 1-800-433-1298 for listeners to leave a one-minute message
• He asks callers to describe their business and the issues or questions they want help with

Reintroduction of Neeraj Shah and Wayfair origin story

Guy welcomes back Neeraj Shah, CEO and co-founder of Wayfair[3:22]
• Guy notes that Neeraj was first on the show in 2018 and calls it an amazing story
Early ventures with co-founder Steve[3:35]
• Guy recalls that Neeraj and his college roommate Steve co-founded many businesses right out of college in their 20s
• He lists some of their niche websites: dinnerplates.com, racksandstands.com, justshagrugs.com
• Guy mentions they even had a site selling only birdhouses and another only grandfather clocks
Transition from many niche sites to Wayfair[4:11]
• Neeraj explains they worked their way through home goods one category at a time, ending up with over 200 websites
• They realized the bigger opportunity was to be known as a destination for all categories rather than separate standalone sites
• About ten years into the business, in 2011, they launched wayfair.com

Longevity of Neeraj and Steve's co-founder relationship

Background on how Neeraj and Steve met[4:43]
• Guy notes they have been working together for 27 years
• They first met in a summer program at Cornell, between their junior and senior years of high school
Neeraj describes why the partnership works[5:32]
• He says they are naturally drawn to different areas of the business
• Steve has always been very involved with the technology side, and the company has always been very technology oriented
• Neeraj has been more drawn to the business side
• They both deeply respect each other's business judgment, making the partnership easy
• Neeraj says you need someone interested in complementary things and with mutual trust to be a great partner
• He characterizes discovering such a partnership as partly art, partly science, and also luck

Wayfair's competitive strategy and scale advantages

Combining scale with entrepreneurial mentality[6:18]
• Neeraj says Wayfair tries to combine the best of two worlds: large-scale resources and a startup-like mentality
• They have enough scale to employ a 2,500-person technology team
• They operate a 25-million-square-foot logistics network including warehouses and transportation delivery operations
Details on Wayfair's logistics infrastructure[5:57]
• Neeraj says they have around 17 or 18 warehouses, each about a million square feet
• They also have about 75 smaller buildings that function as transportation terminals
• Trucks delivering large items to customers' homes depart from these smaller terminals each day
Use of advertising scale[7:27]
• Neeraj states they spend over a billion dollars a year on advertising
• He argues that combining big-company resources with the agility and ambition of a smaller business lets them move fast and do big things
Narrow focus on home goods[7:12]
• Neeraj emphasizes they stay focused on home goods and avoid being distracted by too many categories
• He notes home goods represent over half a trillion dollars across the four countries where Wayfair operates
• This specialization gives them an advantage versus broad retailers like Amazon and Walmart
• Their scale gives them an edge over upstarts focused on the same market but lacking comparable technology and logistics resources

Wayfair's expansion into physical retail

Overview of Wayfair's first large-format store[8:08]
• Guy notes Wayfair opened its first brick-and-mortar store in Illinois, outside Chicago, and plans stores in Atlanta, New York, and Denver
• Neeraj says the first large-format Wayfair store opened in May a year prior, in Wilmette, a northern Chicago suburb
• The store is 150,000 square feet, which Guy compares to the size of a Costco
Purpose and customer experience in the store[8:39]
• Neeraj says the large size allows them to showcase all product categories so customers can see the breadth of what Wayfair offers
• He explains that for purchases like sectionals or bathroom faucets, customers want to see a variety in person
• He reports the store works well because customers already know the brand from its scale and advertising
• In-store, customers can get design guidance, pursue financing, and work with a kitchen cabinet designer
• Neeraj says the physical stores make the brand come to life in a whole new way, which is why they have a pipeline of additional stores

Caller 1: CookStix branding and consumer education

Introduction to CookStix and product concept

Valerie describes CookStix business[9:48]
• Valerie Zweig from Washington, D.C., introduces herself as co-founder of CookStix
• She describes CookStix as a new way to stock your pantry: instant stock sticks that replace wasteful cartons and chemical-laden bouillon
• She says the product is a clean, convenient, and delicious stock option for home cooks
Details of the product format and use[10:59]
• Valerie explains CookStix are dehydrated chicken stock and part of an ingredient line
• They are starting with three dehydrated chicken stocks, with plans to expand into other ingredients
• Instead of buying boxed liquid stock, customers mix the sticks with hot water to make stock
Background: Prescription Chicken and the problem of shipping liquid stock[10:42]
• Valerie and her cousin and co-founder, Taryn Pelicone, previously started a chicken soup delivery business called Prescription Chicken about nine years ago in D.C.
• They also sell chicken soup in national grocery stores
• She notes they spent a lot of time shipping liquid across the country, which is heavy, expensive, and not good for the environment
• As home cooks, they valued great chicken stock but often had half-used boxes wasting in the fridge
• They realized there had to be a better way than pre-liquefied stock and asked why it could not be a product you add water to and use exactly what you need

Valerie's branding and messaging challenge

Misidentification of CookStix's intended use[11:03]
• Valerie says retailers and shoppers are misidentifying how to use CookStix
• She hears comments like "Is it a protein beverage?" or suggestions that they should have more protein in it
• Despite having the word "cook" in the name, people do not always understand it is an ingredient for cooking
Clarifying their positioning versus bouillon and boxed stock[12:25]
• Valerie stresses that CookStix are meant as an innovative ingredient and a new format for a classic product, replacing standard cartons of stock
• She contrasts it with boxed stock, which can be watery and shelf-stable for long periods
• She also contrasts with bouillon, which she calls chemically laden, salty, and not actually leaning on flavor

Early attempts at messaging and feedback from Amazon

Launch channels and discovery of the misunderstanding[12:43]
• Valerie says they launched in late June in Mid-Atlantic Whole Foods stores and on Amazon
• Amazon reviews and feedback revealed that their initial marketing did not clearly communicate that one stick equaled a box of stock
• They created an ad explicitly stating "one stick equals one box of stock," which helped understanding
Rejection of "protein beverage" positioning[13:36]
• Guy asks if protein broth direction is something they want
• Valerie responds they are not headed in that direction; they are competing against boxed stock, not trying to be a drink
• She notes protein beverages need an aggressive flavor profile, whereas chicken stock should be more like a foundational ingredient, similar to salt

Neeraj's advice on literal messaging and packaging

Advocating very literal on-package instructions[14:25]
• Neeraj says that when something is novel, the best way to communicate it can be very rudimentary and literal
• He suggests putting a clear statement on the front like "add 16 ounces of water and your chicken stock's ready to go"
• He explains that literal explanations make novel products intuitive, and creativity can come after understanding is established
Reassessing branding priorities[14:55]
• Valerie acknowledges they focused heavily on branding and eye-catching imagery
• She says they likely need to shrink the "cute little chicken" on the front and increase the prominence of "instant chicken stock"
• Guy points out the packaging already says "instant cooking stock" but still may not be clear enough
Balancing clever taglines versus clarity[16:06]
• Guy suggests a literal tagline like "your carton of chicken stock, now on a stick"
• Valerie shares their current tagline "think outside the stock box" and questions whether it's too clever
• Guy calls the tagline very clever but implies it may not be sufficiently clear for education purposes

Role of social media and founder-led education

Current social efforts and need for more founder presence[16:24]
• Valerie says they have been doing a lot on social media
• She notes they need to work more on founders doing their own education content
• She contrasts this with their chicken soup business, where they intentionally did not make it about themselves
• For CookStix, she believes founders need to lead the narrative on how to use it and show ease of use

Guy and Neeraj's closing thoughts on CookStix

Guy's personal validation of the need for good stock[17:16]
• Guy shares he makes his own chicken stock but would use CookStix in a pinch
• He emphasizes how stock dramatically improves basic dishes like rice when used instead of water
Neeraj's broader marketing lesson[17:05]
• Neeraj reiterates that for novel products, literal explanations are often the strongest marketing starting point

Caller 2: Daily Shade Sunscreen and funding product expansion

Introduction to Daily Shade and origin story

Bree introduces Daily Shade[22:07]
• Bree Van Leeuwen from Orem, Utah, says she is the founder of Daily Shade Sunscreen
• She describes Daily Shade as redefining what true mineral sunscreen can look and feel like
• Their flagship product, Babeshade, launched in 2024 and is designed for kids
• She says it is the first true mineral sunscreen for daily use that disappears like magic on kids' skin, avoiding "little white ghosts"
Health motivation and Utah melanoma context[22:07]
• Bree recounts her daughter having a terrible reaction to a popular chemical sunscreen marketed for kids, including blisters
• She began using true mineral sunscreens but either her daughter still reacted or the products left very white residue
• She notes Utah is the number one state in the nation for melanoma
• She adds that melanoma is a common cancer in women age 26 to 30 and many young girls have facial scars from melanoma surgeries
• Bree previously worked in facial plastic reconstructive surgery and saw young girls with serious facial scars from melanoma
• She cites studies suggesting up to 80% of a person's lifetime sun damage happens before age 18
Professional background and development timeline[23:59]
• Bree is a physician assistant by training and has been practicing medicine for 15 years
• She says it took four years of development and R&D to create their product line
• She notes sunscreen is a drug and must go through the FDA
• She confirms the business is self-funded

Current distribution and traction

Sales channels and store presence[25:17]
• Bree says they sell on their own website and on Amazon
• They are in about 28 physical doors across the country, but not yet in any regional or national distribution
Early revenue milestones and pipeline[25:44]
• Bree says they have sold through their first production run, with just a few bottles left
• They plan to produce again in the fall and have two new product lines coming: a sport line and a women's line
• In response to Guy's question, she confirms they have broken $50,000 in sales

Bree's question about when to seek investment

Constraints from production costs and limited marketing budget[26:18]
• Bree says having an in-house cosmetic chemist lets them come up with products quickly
• She has many product ideas but the high cost of production means she can only sustain one or two product lines a year at current growth
• Because the business is self-funded, her marketing budget is lower than she would like
Core question: bootstrapping versus raising capital[26:38]
• Bree asks what key indicators she should look for to know when it's time to seek investment and give up some equity
• She contrasts that with continuing to bootstrap and grow more slowly

Neeraj and Guy's advice on financing options and timing

Exploring retailer purchase orders and PO financing[27:12]
• Neeraj asks if she has discussed carrying the product with major retailers
• He suggests that a retailer who likes getting in early might give her a purchase order for a modest test rollout
• He explains that purchase orders from larger companies can be financed against, providing capital without selling equity
• Bree says she has not explored regional or national distribution yet because she cannot afford it and is targeting 2027 as the earliest
Other non-equity financing options mentioned[28:53]
• Guy mentions revenue-based financing and lenders who provide loans against predictable sales
• He references Shopify as one company that makes small loans based on sales
• He also mentions SBA loans as another option
Convertible notes as a way to raise early capital[29:02]
• Guy explains that convertible notes normally translate into stock, and there are multiple structures including payback options
• Neeraj says a convertible note is often the most common early-stage instrument
• He explains investors give money now and hold a note that converts when the next round of capital is raised
• The conversion happens at a discount (e.g., 20% or 30%) to the next round's valuation, compensating them for being early
• He notes this allows founders to delay setting a valuation now, which could be hard based solely on current revenue
Bootstrapping philosophy and when to raise equity[30:05]
• Neeraj says he generally recommends not taking money until really necessary, despite the prestige associated with fundraising
• He argues you'd rather not raise money if you can reach the next level without it, even if that means slower progress
• He says the right time to raise is when there is a clear use of funds that you cannot accomplish from business cash flow
• He recounts that Wayfair bootstrapped for 10 years by avoiding buying inventory and instead drop-shipping orders from suppliers' open stock
• They raised equity only to launch the Wayfair brand because they lacked cash flow to fund brand-building at the needed scale
Bree's stance on timing and responses[31:35]
• Bree says she likes the idea of waiting for large purchase orders before seeking help, and could carry the business until a big PO such as 50,000 units

Pursuing regional and national retail like Whole Foods

Guy's suggestion to approach Whole Foods buyers[32:15]
• Guy notes Bree is already in some stores and asks about getting in front of a Whole Foods buyer
• He points out Whole Foods has regional buyers whose job is to find interesting, locally made products
• He suggests using LinkedIn to find names and cold-emailing them
• He cites examples from the show, including Poppy soda, which started at a farmer's market and was picked up by a local Whole Foods before expanding
• Guy notes companies can obtain financing from groups that lend against confirmed purchase orders
Bree's personal risk and commitment[34:22]
• Guy tells Bree she will likely need to "bet on herself" despite the fear
• Bree shares she quit her job as a professor in the physician assistant department at Utah Valley University in January and is "all in" on the business

Caller 3: HerHouse and deciding when to go full-time on a startup

Introduction to HerHouse concept and model

Tess describes HerHouse and its purpose[37:01]
• Tess Milholland, based near San Antonio, Texas, introduces herself as the founder of HerHouse
• She explains HerHouse is an app community of solo women travelers who are background-checked and host each other for free
• The platform creates safe, affordable stays and a supportive network of women around the world
Ways members can use the platform[37:42]
• Tess says there are three ways to stay: asking for accommodation while traveling, home swapping, and home sitting
• She notes some members are nomads without a home base and may not be able to host at certain times
• Even if they cannot host, many members are willing to meet for coffee or activities so solo travelers have an immediate local connection
Membership and revenue model[38:17]
• HerHouse operates on a monthly and yearly membership model
• Membership provides full access to the community and unlimited free accommodation within it
• Some members are expected to host, though Tess notes some nomadic members cannot currently host but still participate socially
Current scale and origin of the idea[38:43]
• Tess says they currently have around 150 members across 20 countries
• She solo-backpacked through Australia in 2017 after college and easily made connections and found accommodation
• She noticed as a solo woman traveler, people opened their homes to her often, giving her immersive cultural experiences
• Back in the U.S., friends asked how she found safe hosts and she realized this was not easy for everyone
• She envisioned an app where all members are background-checked and safety for solo female travelers is the top concern

Tess's workload, job, and core question

Balancing full-time work, startup, and family[40:47]
• Tess is a solo founder building HerHouse on the side of a full-time job in software sales
• She notes she is also a mom and a wife and feels she cannot keep doing all three roles at the current pace
Question about when to jump to full-time founding[40:42]
• Tess asks when a new founder should make the jump to running their startup full-time
• She wonders if there is a specific income threshold or signs of a healthy business that would give her confidence to leave her job
• She shares she has a really good, well-paid remote job with great benefits in software sales, which makes the decision harder

Neeraj's framework for evaluating the jump

Questioning conviction and time use if full-time[41:30]
• Neeraj asks whether, if she could focus full-time on HerHouse, she has a clear vision of how she would use that time with high return
• He distinguishes between having conviction in the business potential versus just wanting more time
• Tess says her to-do list keeps growing and she feels more time would move the needle, but the business is not yet financially dependable
Separating opportunity conviction from financial risk[42:16]
• Neeraj proposes two separate questions: whether HerHouse justifies full-time focus, and whether her finances can support that risk
• He suggests first ignoring money and asking if she has strong conviction that full-time effort would progress the business meaningfully
• Second, he advises assessing whether she is financially in a position to take the risk or can bridge it via friends-and-family or other funding
• He introduces the idea of a "no regret" decision where, even if it fails, she is glad she tried it but is not reckless

Intermediate steps and maintaining current job

Guy's view on avoiding a universal income threshold[44:25]
• Guy says there is no universal income threshold that signals it is time to quit; the decision is highly personal
• He notes Tess's job likely includes commissions and benefits, making it a strong position to hold
Potential for part-time arrangements and hiring help[45:10]
• Neeraj suggests exploring an in-between path, such as a half-time role in her current job if the company values her performance
• He underscores starting by trying to do both, then seeing if there is a non-binary option instead of an all-or-nothing jump
• Guy asks if Tess has considered hiring a part-time community manager to handle some tasks
• Tess shares she recently hired a community and social media manager based in the Philippines because she lacked time to be present on social media
• Neeraj notes it is early but she may find increasing leverage from such help without overspending

Tess's mindset and current plan

Intention to keep job while testing growth[47:55]
• Tess says she can afford to have someone help but cannot yet afford to quit her job
• She sees HerHouse's inclusion in major chains like Whole Foods, Sprouts, and Sephora as dream goals on her goal board, used metaphorically for large partners
• Neeraj reiterates taking it one step at a time and not worrying about four steps at once

Closing reflections on entrepreneurship and Neeraj's early business model clip

Neeraj on balancing multiple life responsibilities for founders

Acknowledging Tess's load versus his early experience[48:46]
• Neeraj notes that unlike his early days, Tess is balancing not just a startup and a job but also being married and having a young child
• He says he and Steve started young and worked nonstop in the early years but had fewer life obligations
• He describes early years as "effectively nonstop" work but emphasizes that today he recognizes founding while managing family is a lot to juggle

Advice Neeraj would give his younger self

Non-linear nature of entrepreneurial journeys[49:36]
• Asked what he would tell his younger self, Neeraj says nothing is ever linear and always up-and-to-the-right
• He points out that stories often highlight only the high notes, obscuring real ups and downs
• He encourages founders to expect a real journey with highs and lows and not to rush to a "success point"
Importance of enjoying the work and learning from setbacks[50:16]
• Neeraj says this is why you must do something you enjoy, so the highs and lows are within a mission you care about
• He stresses being disciplined in picking priorities and continuously learning from things that do not work
• He observes that learnings from failures often lead to the next "aha" moment

Replay of favorite clip illustrating early single-product sites

Guy revisits Neeraj's earlier episode segment on niche domains[52:09]
• Guy plays a clip where he reads straightforward domain names Neeraj and Steve launched, such as Hotplates.com and Allbarstools.com
• He mentions Mydinnerplate.com, which sold dinner plates
• He highlights Everygrandfatherclock.com as a site in a "very hot category" whose items were painful to ship
• Neeraj remarks in the clip that they discovered people were searching for those specific products

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

When you introduce a genuinely new product format, lead with simple, literal messaging that explains exactly what it is and how to use it before relying on clever branding or taglines.

Reflection Questions:

  • • Where in my current product or service description could a literal, step-by-step explanation reduce confusion for new customers?
  • • How might simplifying my packaging copy or homepage to clearly say "this equals that" change how quickly people understand my offering?
  • • What concrete test (e.g., A/B testing different taglines) can I run in the next month to compare clever messaging versus ultra-literal explanations?
2

Use financing tools that match the stage and risk of your business-such as purchase-order financing, revenue-based loans, or convertible notes-before automatically trading away equity.

Reflection Questions:

  • • What assets or future commitments (like signed purchase orders or predictable revenue) could I potentially borrow against instead of selling equity right now?
  • • How would my decision-making change if I treated outside capital as fuel for clearly defined, high-return projects rather than a general safety net?
  • • Which funding options (SBA loans, PO financing, revenue-based financing, convertible notes) should I research this week to understand their fit for my current situation?
3

Bootstrapping as far as you can gives you control and discipline, but raising capital makes sense once there's a specific, high-impact use of funds you cannot reach through organic cash flow.

Reflection Questions:

  • • What specific project or milestone in my business would I fund immediately if I had extra capital, and what measurable outcome would I expect from it?
  • • How might my growth path look if I committed to bootstrapping until I can clearly articulate a single, high-ROI use of outside money?
  • • What evidence could I gather over the next 3-6 months to prove that a particular investment (like a brand launch or new product line) deserves external funding?
4

When you're juggling a demanding job, a startup, and family, it's often wiser to create intermediate steps-like hiring targeted help or negotiating reduced hours-than to make an all-or-nothing leap.

Reflection Questions:

  • • Which recurring tasks in my startup could I safely delegate to a part-time contractor so I can focus on the highest-leverage work?
  • • How could a conversation with my current employer about flexible or reduced hours change my ability to invest more energy in my venture without risking my family's stability?
  • • What small experiment could I run over the next 60 days to test whether more focused time on my startup actually produces the results I expect?
5

Strong long-term partnerships are built on complementary strengths and deep trust in each other's judgment, allowing each person to own their lane while still acting as a unified team.

Reflection Questions:

  • • In my current collaborations, where do complementary skills exist and where are we overlapping or stepping on each other's toes?
  • • How might explicitly acknowledging and formalizing "who owns what" improve trust and speed of decision-making in my team or partnership?
  • • What concrete action could I take this week to show greater trust in a partner's or teammate's judgment in their area of expertise?
6

Entrepreneurial journeys are rarely linear, so you need to choose work you genuinely enjoy and treat setbacks as information that leads to the next "aha" rather than as final verdicts.

Reflection Questions:

  • • Looking back at the past year, which setbacks in my work actually taught me something important or redirected me in a useful way?
  • • How would I approach risk and experimentation differently if I viewed my path as a series of iterations rather than a straight line to a single success point?
  • • What is one current challenge I can reframe as a learning opportunity, and what specific question can I ask to extract a lesson from it?

Episode Summary - Notes by Alex

Advice Line with Niraj Shah of Wayfair
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