141: Managing People as a Fast Growth Startup with Katelyn Gleason of Eligible.com

Most founders obsess over tactics, hacks, and strategies. But the truth? None of it matters if you don’t have the right mindset. In this episode, I share the mental frameworks I’ve learned after a decade of building Foundr and interviewing 100+ of the world’s most successful entrepreneurs. From why 50% of success comes down to belief, to how to reframe failure as data, these are the mindset shifts that will keep you in the game long enough to win. Here’s what you’ll take away: • Why every founder needs to think in decades but act in days• How to stop comparing your chapter 1 to someone else’s chapter 20• The simple shifts that turn fear and failure into growth If you’re feeling impatient, doubting yourself, or wondering why success is taking so long, this episode will give you the perspective and tools to reset, refocus, and keep building. This is a brand new solo series I’m testing, and I’d love your feedback. Email me directly at nathan@foundr.com — I read every reply. Hope you enjoy it. SAVE 50% ON OMNISEND FOR 3 MONTHS Get 50% off your first 3 months of email and SMS marketing with Omnisend with the code FOUNDR50. Just head to ⁠⁠⁠⁠⁠⁠https://your.omnisend.com/foundr⁠⁠⁠⁠⁠⁠ to get started. HOW WE CAN HELP YOU SCALE YOUR BUSINESS FASTER Learn directly from 7, 8 & 9-figure founders inside Foundr+ Start your $1 trial → ⁠⁠⁠⁠⁠⁠https://www.foundr.com/startdollartrial⁠⁠⁠⁠⁠⁠ PREFER A CUSTOM ROADMAP AND 1-ON-1 COACHING? → Starting from scratch? Apply here → ⁠⁠⁠⁠⁠⁠https://foundr.com/pages/coaching-start-application⁠⁠⁠⁠⁠⁠ → Already have a store? Apply here → ⁠⁠⁠⁠⁠⁠https://foundr.com/pages/coaching-growth-application⁠⁠⁠⁠⁠⁠ BOOST REVENUE WITHOUT MORE ADS We use Aftersell for simple post-purchase offers that lift sales fast. ⁠⁠⁠https://try.aftersell.app/ptiz4gnmvff7⁠⁠⁠ to get started. CONNECT WITH NATHAN CHAN Instagram → ⁠⁠⁠⁠⁠⁠https://www.instagram.com/nathanchan⁠⁠⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/nathanhchan/⁠⁠⁠⁠⁠⁠ FOLLOW FOUNDR FOR MORE BUSINESS GROWTH STRATEGIES YouTube → ⁠⁠⁠⁠⁠⁠https://bit.ly/2uyvzdt⁠⁠⁠⁠⁠⁠ Website → ⁠⁠⁠⁠⁠⁠https://www.foundr.com⁠⁠⁠⁠⁠⁠ Instagram → ⁠⁠⁠⁠⁠⁠https://www.instagram.com/foundr/⁠⁠⁠⁠⁠⁠ Facebook → ⁠⁠⁠⁠⁠⁠https://www.facebook.com/foundr⁠⁠⁠⁠⁠⁠ Twitter → ⁠⁠⁠⁠⁠⁠https://www.twitter.com/foundr⁠⁠⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/foundr/⁠⁠⁠⁠⁠⁠ Podcast → ⁠⁠⁠⁠⁠⁠https://www.foundr.com/podcast⁠

7 Okt 8min

Phoebe Gates went from failed prototypes in her Stanford dorm room to building one of the fastest growing fashion-tech startups in the world. In this interview, the co-founder of AI shopping app Phia shares how she and her co-founder Sophia Kianni scaled from 200 early users to half a million downloads, raised $9M from investors like Kleiner Perkins, Kris Jenner, and Sara Blakely, and turned their vision into a personal AI shopping assistant trusted by a new generation of consumers. From building in public and hacking growth with feedback loops to pitching high-profile investors and navigating privilege, Phoebe breaks down the exact strategies that fueled her rapid rise as a young founder. What you’ll learn from this interview: • How Phoebe went from 50+ failed ideas to finding product-market fit in fashion-tech • The grassroots tactics she used to get her first 200 users • Why feedback loops and “pizza nights” became their biggest growth hack • How she pitched and secured investors like Kleiner Perkins, Kris Jenner, and Sara Blakely • The mindset shift that helped her see failure as experimentation • Why building in public became an unfair advantage for distribution and community • How to leverage AI and automation as a young founder to scale faster By the end of this interview, you’ll walk away with a playbook for finding your idea, validating it with real users, and scaling it into a fast-growth business—so you can apply the same principles to your own entrepreneurial journey. You can download the Phia app here SAVE 50% ON OMNISEND FOR 3 MONTHS Get 50% off your first 3 months of email and SMS marketing with Omnisend with the code FOUNDR50. Just head to https://your.omnisend.com/foundr to get started. HOW WE CAN HELP YOU SCALE YOUR BUSINESS FASTER Learn directly from 7, 8 & 9-figure founders inside Foundr+ Start your $1 trial → https://www.foundr.com/startdollartrial PREFER A CUSTOM ROADMAP AND 1-ON-1 COACHING? → Starting from scratch? Apply here → https://foundr.com/pages/coaching-start-application → Already have a store? Apply here → https://foundr.com/pages/coaching-growth-application CONNECT WITH NATHAN CHAN Instagram → https://www.instagram.com/nathanchan LinkedIn → https://www.linkedin.com/in/nathanhchan/ CONNECT WITH PHOEBE GATES Website → https://phia.com/ Instagram → https://www.instagram.com/phoebegates/ LinkedIn → https://www.linkedin.com/in/phoebe-gates-82a60b296/ FOLLOW FOUNDR FOR MORE BUSINESS GROWTH STRATEGIES YouTube → https://bit.ly/2uyvzdt Website → https://www.foundr.com Instagram → https://www.instagram.com/foundr/ Facebook → https://www.facebook.com/foundr Twitter → https://www.twitter.com/foundr LinkedIn → https://www.linkedin.com/company/foundr/ Podcast → https://www.foundr.com/podcast

3 Okt 49min

Most founders think they need a completely original idea to succeed. The truth? Great businesses are often built by borrowing brilliance — and putting your own spin on what already works. In this episode, I break down the concept of “good artists copy, great artists steal,” and show you how to apply it in your business. From how I grew Foundr’s Instagram to how I built and exited my ecommerce brand, Healthie, this approach has helped me create traction faster without reinventing the wheel. Here’s what you’ll take away: • Why borrowing proven strategies beats starting from scratch • Real examples of how top brands like Canva, Airbnb, and Dollar Shave Club modeled what worked • How to ethically “steal” ideas, put your own twist on them, and win in your market If you’re stuck thinking you need the next revolutionary idea, this episode will free you to focus on what matters most: finding what already works, making it better, and making it your own. This is a brand new solo series I’m testing, and I’d love your feedback. Email me directly at nathan@foundr.com — I read every reply. Hope you enjoy it. SAVE 50% ON OMNISEND FOR 3 MONTHS Get 50% off your first 3 months of email and SMS marketing with Omnisend with the code FOUNDR50. Just head to ⁠⁠⁠⁠⁠⁠https://your.omnisend.com/foundr⁠⁠⁠⁠⁠⁠ to get started. HOW WE CAN HELP YOU SCALE YOUR BUSINESS FASTER Learn directly from 7, 8 & 9-figure founders inside Foundr+ Start your $1 trial → ⁠⁠⁠⁠⁠⁠https://www.foundr.com/startdollartrial⁠⁠⁠⁠⁠⁠ PREFER A CUSTOM ROADMAP AND 1-ON-1 COACHING? → Starting from scratch? Apply here → ⁠⁠⁠⁠⁠⁠https://foundr.com/pages/coaching-start-application⁠⁠⁠⁠⁠⁠ → Already have a store? Apply here → ⁠⁠⁠⁠⁠⁠https://foundr.com/pages/coaching-growth-application⁠⁠⁠⁠⁠⁠ BOOST REVENUE WITHOUT MORE ADS We use Aftersell for simple post-purchase offers that lift sales fast. ⁠⁠⁠https://try.aftersell.app/ptiz4gnmvff7⁠⁠⁠ to get started. CONNECT WITH NATHAN CHAN Instagram → ⁠⁠⁠⁠⁠⁠https://www.instagram.com/nathanchan⁠⁠⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/nathanhchan/⁠⁠⁠⁠⁠⁠ FOLLOW FOUNDR FOR MORE BUSINESS GROWTH STRATEGIES YouTube → ⁠⁠⁠⁠⁠⁠https://bit.ly/2uyvzdt⁠⁠⁠⁠⁠⁠ Website → ⁠⁠⁠⁠⁠⁠https://www.foundr.com⁠⁠⁠⁠⁠⁠ Instagram → ⁠⁠⁠⁠⁠⁠https://www.instagram.com/foundr/⁠⁠⁠⁠⁠⁠ Facebook → ⁠⁠⁠⁠⁠⁠https://www.facebook.com/foundr⁠⁠⁠⁠⁠⁠ Twitter → ⁠⁠⁠⁠⁠⁠https://www.twitter.com/foundr⁠⁠⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/foundr/⁠⁠⁠⁠⁠⁠ Podcast → ⁠⁠⁠⁠⁠⁠https://www.foundr.com/podcast⁠

30 Sep 8min

David Heath and Randy Goldberg turned Bombas from a scrappy Indiegogo campaign into the most successful Shark Tank investment of all time—now valued at $3.4 billion. In this interview, the Bombas co-founders share how a simple insight about homelessness sparked a mission-driven sock company, how they bootstrapped their way to product-market fit, and the strategies that allowed them to scale profitably in one of the most competitive eras of eCommerce. From bootstrapping and fundraising to Shark Tank, celebrity endorsements, and building a brand people love, this episode is a masterclass in combining profit with purpose. What you’ll learn from this interview: • How Bombas grew from a $140K Indiegogo campaign to a $3.4B business • The one-for-one donation model and why it worked when others doubted it • Bootstrapping tactics that fueled growth before raising outside capital • The Shark Tank experience and why it was a turning point for the brand • How Bombas navigated rising customer acquisition costs and scaled profitably • The mindset shifts needed to build a mission-driven business at scale • Why focus, authenticity, and constraints can be the biggest drivers of innovation By the end of this interview, you’ll walk away with a playbook for building a business that blends purpose with profit—so you can grow faster, stay focused, and create a brand that stands the test of time. SAVE 50% ON OMNISEND FOR 3 MONTHS Get 50% off your first 3 months of email and SMS marketing with Omnisend with the code FOUNDR50. Just head to https://your.omnisend.com/foundr to get started. HOW WE CAN HELP YOU SCALE YOUR BUSINESS FASTER Learn directly from 7, 8 & 9-figure founders inside Foundr+ Start your $1 trial → https://www.foundr.com/startdollartrial PREFER A CUSTOM ROADMAP AND 1-ON-1 COACHING? → Starting from scratch? Apply here → https://foundr.com/pages/coaching-start-application → Already have a store? Apply here → https://foundr.com/pages/coaching-growth-application CONNECT WITH NATHAN CHAN Instagram → https://www.instagram.com/nathanchan LinkedIn → https://www.linkedin.com/in/nathanhchan/ CONNECT WITH BOMBAS Website → https://bombas.com/ Instagram → https://www.instagram.com/bombas/ LinkedIn → https://www.linkedin.com/company/bombas/ David's LinkedIn → https://www.linkedin.com/in/davidtheath/ Randy's LinkedIn → https://www.linkedin.com/in/randysgoldberg/ FOLLOW FOUNDR FOR MORE BUSINESS GROWTH STRATEGIES YouTube → https://bit.ly/2uyvzdt Website → https://www.foundr.com Instagram → https://www.instagram.com/foundr/ Facebook → https://www.facebook.com/foundr Twitter → https://www.twitter.com/foundr LinkedIn → https://www.linkedin.com/company/foundr/ Podcast → https://www.foundr.com/podcast

26 Sep 43min

When you’re just starting out, the fastest way to grow isn’t automation, ads, or scaling systems — it’s doing things that don’t scale. In this episode, I share why the most successful founders — from billion-dollar startups to small ecommerce brands — all begin by leaning into the unscalable. From replying personally to every email, to sending hundreds of Instagram DMs, to handwriting thank-you cards for early customers, these strategies create the kind of emotional connection that big brands can’t compete with. Here’s what you’ll take away: • Why doing things that don’t scale is your biggest advantage as a small brand • Real examples of how I and other founders used this to grow early traction • Specific tactics you can start today to build stronger customer relationships If you’re an early-stage founder, this episode will show you exactly how to build momentum, create raving fans, and uncover what truly works — long before you scale. This is a brand new solo series I’m testing, and I’d love your feedback. Email me directly at nathan@foundr.com — I read every reply. Hope you enjoy it. SAVE 50% ON OMNISEND FOR 3 MONTHS Get 50% off your first 3 months of email and SMS marketing with Omnisend with the code FOUNDR50. Just head to ⁠⁠⁠⁠⁠https://your.omnisend.com/foundr⁠⁠⁠⁠⁠ to get started. HOW WE CAN HELP YOU SCALE YOUR BUSINESS FASTER Learn directly from 7, 8 & 9-figure founders inside Foundr+ Start your $1 trial → ⁠⁠⁠⁠⁠https://www.foundr.com/startdollartrial⁠⁠⁠⁠⁠ PREFER A CUSTOM ROADMAP AND 1-ON-1 COACHING? → Starting from scratch? Apply here → ⁠⁠⁠⁠⁠https://foundr.com/pages/coaching-start-application⁠⁠⁠⁠⁠ → Already have a store? Apply here → ⁠⁠⁠⁠⁠https://foundr.com/pages/coaching-growth-application⁠⁠⁠⁠⁠ BOOST REVENUE WITHOUT MORE ADS We use Aftersell for simple post-purchase offers that lift sales fast. ⁠⁠https://try.aftersell.app/ptiz4gnmvff7⁠⁠ to get started. CONNECT WITH NATHAN CHAN Instagram → ⁠⁠⁠⁠⁠https://www.instagram.com/nathanchan⁠⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠⁠https://www.linkedin.com/in/nathanhchan/⁠⁠⁠⁠⁠ FOLLOW FOUNDR FOR MORE BUSINESS GROWTH STRATEGIES YouTube → ⁠⁠⁠⁠⁠https://bit.ly/2uyvzdt⁠⁠⁠⁠⁠ Website → ⁠⁠⁠⁠⁠https://www.foundr.com⁠⁠⁠⁠⁠ Instagram → ⁠⁠⁠⁠⁠https://www.instagram.com/foundr/⁠⁠⁠⁠⁠ Facebook → ⁠⁠⁠⁠⁠https://www.facebook.com/foundr⁠⁠⁠⁠⁠ Twitter → ⁠⁠⁠⁠⁠https://www.twitter.com/foundr⁠⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠⁠https://www.linkedin.com/company/foundr/⁠⁠⁠⁠⁠ Podcast → ⁠⁠⁠⁠⁠https://www.foundr.com/podcast⁠

23 Sep 7min

Brian Littlefield is the co-founder and Chief Product Officer of Jocko Fuel—one of the fastest-growing supplement brands in America. But his story didn’t start in a boardroom. It started with a life-changing health wake-up call. In this episode, Brian shares how he went from overweight and directionless to building a trusted supplement empire backed by Navy SEAL legend Jocko Willink. You'll hear how they launched Jocko Fuel with a single product, the risky decision to tie the brand to Jocko’s name, and the surprising reason their customer base is so fanatically loyal. What you’ll learn: • Why they anchored the brand to Jocko’s reputation • How Brian built products customers actually stick with • Why quality and transparency are their greatest weapons • The scrappy early days of launching without big resources • Lessons from martial arts that shaped his leadership style • The real reason Jocko Fuel stands out in a saturated space If you want a blueprint for building a brand based on trust, community, and quality—this one’s a must-listen. Foundr Community Offers Want 1-on-1 mentorship to launch or scale your brand faster? Apply for eCommerce coaching: → Starting your ecom biz? ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ → Already selling and want to scale? ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ Want all-access to step-by-step training from 7, 8 & 9-figure founders? Start your Foundr+ $1 trial today → ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ Omnisend | Get 50% off your first 3 months of email and SMS marketing with Omnisend with the code FOUNDR50. ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ to get started. Connect With Nathan Chan Instagram → ⁠⁠⁠⁠⁠⁠⁠Click Here⁠⁠⁠⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠⁠⁠⁠Click Here⁠⁠⁠⁠⁠⁠⁠ Connect With Brian Littlefield Website → Click Here Instagram → Click Here Brian's LinkedIn → Click Here Follow Foundr for More Business Growth Strategies YouTube → ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ Website → ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ Instagram → ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ Facebook → ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ Twitter → ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠⁠⁠⁠Click here⁠⁠⁠⁠⁠⁠⁠ Podcast → ⁠⁠⁠⁠⁠⁠⁠Click here

19 Sep 46min

Most ecommerce founders think the only way to grow is to get more traffic — but often, the fastest way to increase sales is by making more from the traffic you already have. In this episode, I share a proven “second sale” strategy you can use to increase your conversion rate, average order value (AOV), and customer lifetime value (CLV) without spending a single extra dollar on ads. This is the exact approach Amazon uses to generate billions in extra revenue — and it works just as well for smaller brands. Here’s what you’ll take away: • How to identify if you have a conversion problem vs. a traffic problem • The post-purchase upsell strategy that can boost your revenue by 10–50% • Tools and tactics to increase AOV and CLV with zero additional ad spend If you’re looking to grow your store without increasing your traffic budget, this episode will give you a simple, repeatable strategy to unlock more revenue from the customers you already have. This is a brand new solo series I’m testing, and I’d love your feedback. Email me directly at nathan@foundr.com — I read every reply. Hope you enjoy it. SAVE 50% ON OMNISEND FOR 3 MONTHS Get 50% off your first 3 months of email and SMS marketing with Omnisend with the code FOUNDR50. Just head to ⁠⁠⁠⁠https://your.omnisend.com/foundr⁠⁠⁠⁠ to get started. HOW WE CAN HELP YOU SCALE YOUR BUSINESS FASTER Learn directly from 7, 8 & 9-figure founders inside Foundr+ Start your $1 trial → ⁠⁠⁠⁠https://www.foundr.com/startdollartrial⁠⁠⁠⁠ PREFER A CUSTOM ROADMAP AND 1-ON-1 COACHING? → Starting from scratch? Apply here → ⁠⁠⁠⁠https://foundr.com/pages/coaching-start-application⁠⁠⁠⁠ → Already have a store? Apply here → ⁠⁠⁠⁠https://foundr.com/pages/coaching-growth-application⁠⁠⁠⁠ BOOST REVENUE WITHOUT MORE ADS We use Aftersell for simple post-purchase offers that lift sales fast. ⁠https://try.aftersell.app/ptiz4gnmvff7⁠ to get started. CONNECT WITH NATHAN CHAN Instagram → ⁠⁠⁠⁠https://www.instagram.com/nathanchan⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠https://www.linkedin.com/in/nathanhchan/⁠⁠⁠⁠ FOLLOW FOUNDR FOR MORE BUSINESS GROWTH STRATEGIES YouTube → ⁠⁠⁠⁠https://bit.ly/2uyvzdt⁠⁠⁠⁠ Website → ⁠⁠⁠⁠https://www.foundr.com⁠⁠⁠⁠ Instagram → ⁠⁠⁠⁠https://www.instagram.com/foundr/⁠⁠⁠⁠ Facebook → ⁠⁠⁠⁠https://www.facebook.com/foundr⁠⁠⁠⁠ Twitter → ⁠⁠⁠⁠https://www.twitter.com/foundr⁠⁠⁠⁠ LinkedIn → ⁠⁠⁠⁠https://www.linkedin.com/company/foundr/⁠⁠⁠⁠ Podcast → ⁠⁠⁠⁠https://www.foundr.com/podcast⁠

16 Sep 7min

Julie Wainwright, founder of The RealReal, reveals how she built a billion-dollar resale marketplace that transformed luxury fashion. In this exclusive Foundr Podcast interview, Julie shares how she scaled The RealReal to over $1B in revenue, reached 38 million members, and took the company public on the Nasdaq. From her early lessons at Pets.com to reinventing resale as “cool” and breaking into the luxury market, Julie unpacks the strategies, risks, and mindset shifts that fuelled her success. Whether you’re building an eCommerce brand, launching a marketplace, or navigating setbacks as a founder, this interview delivers invaluable lessons on execution, resilience, and scaling big ideas. What you’ll learn from this interview: • How Julie identified an opportunity Amazon couldn’t replicate and turned it into The RealReal • The strategies she used to seed supply and build a two-sided marketplace • Why values-driven hiring and culture were critical to scaling past $1B in revenue • Lessons from shutting down Pets.com and how it shaped her next venture • How she navigated taking The RealReal public and the realities of IPO wealth • The impact of COVID on The RealReal and what it taught her about resilience • Why values alignment and integrity are the most important traits in your team and board By the end of this interview, you’ll walk away with proven insights from one of the most experienced entrepreneurs in Silicon Valley—so you can build, scale, and sustain your own eCommerce or marketplace business with clarity and confidence. SAVE 50% ON OMNISEND FOR 3 MONTHS Get 50% off your first 3 months of email and SMS marketing with Omnisend with the code FOUNDR50. Just head to ⁠https://your.omnisend.com/foundr⁠ to get started. HOW WE CAN HELP YOU SCALE YOUR BUSINESS FASTER Learn directly from 7, 8 & 9-figure founders inside Foundr+ Start your $1 trial → ⁠https://www.foundr.com/startdollartrial⁠ PREFER A CUSTOM ROADMAP AND 1-ON-1 COACHING? → Starting from scratch? Apply here → ⁠https://foundr.com/pages/coaching-start-application⁠ → Already have a store? Apply here → ⁠https://foundr.com/pages/coaching-growth-application⁠ CONNECT WITH NATHAN CHAN Instagram → ⁠https://www.instagram.com/nathanchan⁠ LinkedIn → ⁠https://www.linkedin.com/in/nathanhchan/⁠ CONNECT WITH JULIE WAINWRIGHT Website → https://www.therealreal.com/ Instagram → ⁠https://www.instagram.com/realrealjulie/ FOLLOW FOUNDR FOR MORE BUSINESS GROWTH STRATEGIES YouTube → ⁠https://bit.ly/2uyvzdt⁠ Website → ⁠https://www.foundr.com⁠ Instagram → ⁠https://www.instagram.com/foundr/⁠ Facebook → ⁠https://www.facebook.com/foundr⁠ Twitter → ⁠https://www.twitter.com/foundr⁠ LinkedIn → ⁠https://www.linkedin.com/company/foundr/⁠ Podcast → ⁠https://www.foundr.com/podcast

12 Sep 1h