How I Built This with Guy Raz
How I Built This with Guy Raz

How I Built Resilience: Bert and John Jacobs of Life is Good

Bert and John Jacobs had just come off a $100 million year for their Boston-based apparel company, Life is Good. However, the COVID-19 pandemic has upended business as usual, forcing the brothers to invest in a new printing model while trying to encourage optimism during this time of economic and so

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Guy Raz | Wondery HostBert Jacobs Guest

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Episode Summary

Executive Summary: Bert and John Jacobs describe how Life is Good used the COVID crisis to accelerate a long-planned shift from wholesale to direct-to-consumer, investing in direct-to-garment printing and safer distribution to respond faster to demand. They frame optimism as a practical, “rational” tool that helps their brand and community endure hardship.

Main Topics: COVID as a forced business model pivot (Priority: 5/5): The brothers explain that retail shutdowns nearly decimated the wholesale-heavy business, prompting immediate layoffs/bankruptcy discussions and a rapid move toward direct-to-consumer operations. Direct-to-garment printing and inventory reduction (Priority: 5/5): They invested millions in printing technology that allows them to print individual orders on blank shirts, reducing inventory risk and aligning supply more closely with demand. Optimism as brand identity and business engine (Priority: 5/5): Life is Good’s mission is to spread optimism, and the founders argue that this purpose drives customer loyalty and helps the company thrive during crises. Community-driven storytelling and emotional connection (Priority: 4/5): The brand is co-authored by customers who share personal stories of resilience, grief, gratitude, and hope; this community feedback reinforces the company’s purpose. Leadership, listening, and employee trust (Priority: 4/5): The founders credit their leadership team for guiding the safe continuation of operations and emphasize listening to employees, clear communication, and hiring resilient people. Rational optimism versus denial (Priority: 4/5): They distinguish between unrealistic positivity and a grounded optimism that acknowledges hardship while focusing on coping mechanisms, adaptability, and solutions.

Key Arguments: The pandemic accelerated a strategic shift they already wanted to make from wholesale, long-lead-time retail to a faster direct-to-consumer model. Inventory is dangerous for apparel businesses; making to order reduces waste and improves responsiveness. A strong underlying purpose—spreading optimism—makes a company more resilient in downturns and crises. Customers are not just buyers but co-creators who supply stories, data, and meaning that shape the brand. Healthy coping mechanisms such as exercise, connection, and creativity are central to sustaining leadership and morale. Listening to employees and letting them surface solutions improved decision-making during the crisis.

Data Points: Revenue: over $100 million last year - Describes Life is Good’s scale before the pandemic disruptions. Wholesale share of business: half of the business - Wholesale exposure made the company vulnerable when retailers closed. Supply chain window: 12 to 18 months - Traditional retail planning cycle the company wanted to shorten. Technology investment: several million dollars - Amount spent on direct-to-garment printing capability before COVID hit. E-commerce growth: doubled to date over the last year - Online sales increased as wholesale collapsed. Wholesale business decline: down to next to nothing - Retail closures nearly eliminated wholesale sales during COVID. Kids Foundation donations: 300% since March 1st - Charitable giving increased sharply during the pandemic period. Operations timing: first 60 days - Team worked around the clock during the first two months to switch the model.

Pivotal Quotes: "the best defense is offense" — Bert Jacobs: Explaining the decision to keep operating safely and pivot aggressively rather than retreating. "the tail was wagging the dog" — Bert Jacobs: Describing how the wholesale business and long supply chain had come to dominate the company’s model. "You have to enable your consumers to co-author the story of your brand" — Bert Jacobs: On modern branding and the importance of customer participation in shaping Life is Good.

Implications: Brands with strong purpose and flexible operations may weather shocks better than inventory-heavy legacy retailers. The episode suggests that listening, speed, and customer co-creation are now essential competitive advantages.

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About How I Built This with Guy Raz

Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds.New episodes release on Mondays and Thursdays. Listen to How I Built This on the Wondery App or wherever you listen to your podcasts. You can lis...

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