How I Built This with Guy Raz
Episode Title: Advice Line with Andy Dunn of Bonobos
Release Date: April 17, 2025
Host: Guy Raz
Guest: Andy Dunn, Co-founder of Bonobos and Founder of Pie
Description: In this episode, Guy Raz welcomes Andy Dunn back to discuss his journey with Bonobos, his struggles with mental health, the creation of his new social app Pie, and offers valuable advice to entrepreneurs facing their own business challenges.
1. Introduction
Guy Raz opens the episode by welcoming Andy Dunn, acknowledging his previous appearance on the show where Andy shared the story of building Bonobos into a multimillion-dollar apparel brand. Raz highlights Andy’s openness about his mental health struggles, which has become a significant part of his purpose and mission.
Notable Quote:
"[...] this has really become a really important part of your sort of purpose in life, to talk about this and to be open about it and to help other entrepreneurs understand that there are a lot of mental health challenges that are involved in starting a business."
— Guy Raz [04:17]
2. Andy Dunn’s Background and Bonobos’ Journey
Andy reflects on Bonobos’ inception during his time at Stanford Business School with co-founder Brian Spaly. He recounts the company’s growth and eventual acquisition by Walmart for around $300 million in 2017. Andy discusses the personal and professional challenges he faced during this period, including significant mental health issues.
Notable Quote:
"My original relationship with mental health was to be in denial of the condition that I had, which is bipolar type 1. [...] it was such a blessing that I got a wake-up call in 2016."
— Andy Dunn [05:13]
3. Mental Health Challenges and Personal Experiences
Andy delves deeper into his mental health journey, describing a pivotal moment in 2016 that led to his diagnosis of bipolar disorder. He shares the difficult experience of being in the psych ward and how this event transformed his approach to life and business. This period of his life inspired him to openly discuss mental health and influenced the creation of his new venture, Pie.
Notable Quote:
"In retrospect, best thing that ever happened to me because it informed not only my new life's work of talking about it openly and trying to help other people on this journey, it also inspired my new company, Pie."
— Andy Dunn [05:59]
4. Founding Pie: A Social App for Friendships
Moving forward, Andy introduces Pie, a social app designed to help individuals form genuine friendships and participate in real-life social events. He explains how relocating from New York to Chicago during the pandemic left him feeling isolated, which motivated him to create Pie. The app aims to bridge the gap for people struggling to build new social connections, especially men over 40 who often find it challenging to expand their social circles beyond family.
Notable Quote:
"We could go so deep into this. We even at PIE had to introduce a series called Dudes Getting Pancakes to create the lowest possible barrier to just meeting some new guys."
— Andy Dunn [07:17]
5. Business Advice for Entrepreneurs
The core of the episode revolves around addressing listener questions through the Advice Line. Two callers, Michelle Cosentino of Top Banana and Alex Supak of Broda Beverage Co., seek guidance on scaling their businesses. Andy and Guy provide strategic advice on marketing, pricing, wholesale versus direct-to-consumer models, and leveraging influencer partnerships.
Caller 1: Michelle Cosentino, Top Banana
Michelle seeks advice on effectively marketing her vintage-inspired women's tennis apparel to Gen Y consumers. Andy emphasizes the importance of Instagram for brand growth and suggests building an army of brand ambassadors by gifting products rather than paying high-profile influencers.
Notable Quote:
"I think it's all about Instagram for the evolution you're making, because Gen X is there and Gen Y is there in droves."
— Andy Dunn [15:20]
He further advises embracing the brand’s price point and considering wholesale opportunities, especially targeting high-end boutiques and resort gift shops to scale the business effectively.
Notable Quote:
"If you can find someone brand aligned, and it's probably someone who at some point, like, you send the product to and loves it."
— Andy Dunn [18:14]
Caller 2: Alex Supak, Broda Beverage Co.
Alex seeks strategies to educate consumers about the transparency and quality of his alcohol products while increasing online sales. Andy challenges the effectiveness of focusing solely on e-commerce and recommends prioritizing wholesale partnerships with major retailers to scale efficiently.
Notable Quote:
"You can't increase sales on the website and you shouldn't try. [...] focus all your energy into wholesale."
— Andy Dunn [45:29]
He also advises Sabrina Nass (another caller) to consider subscription models and to adjust pricing to be competitive within the market. Andy underscores the necessity of being the least expensive option while maintaining a strong brand presence to compete with established players.
Notable Quote:
"You’ve got to be like head to head. I would want you to be the least expensive biscotti on the market with the best brand."
— Andy Dunn [49:05]
6. Key Takeaways and Insights
Throughout the episode, Andy Dunn shares valuable lessons learned from his entrepreneurial journey:
- Prioritize Mental Health: Acknowledging and addressing mental health challenges is crucial for sustainable business growth.
- Embrace Tactical Marketing: Utilize platforms like Instagram and build genuine relationships with brand ambassadors to enhance visibility.
- Wholesale Over Direct-to-Consumer: Leveraging wholesale partnerships with established retailers can offer scalability that direct-to-consumer models may lack.
- Competitive Pricing: Ensure products are competitively priced to attract a broader customer base without compromising brand quality.
- Adaptability and Resilience: Being willing to pivot and adapt business strategies in response to market feedback and personal experiences is essential.
Notable Quote:
"Companies don't die because the companies fail. They die because the entrepreneur gives up."
— Andy Dunn [54:00]
7. Conclusion
Guy Raz wraps up the episode by encouraging listeners to explore Andy Dunn’s previous appearance on How I Built This to gain deeper insights into building a successful brand. He also invites entrepreneurs to share their business challenges through the Advice Line for future episodes.
Notable Quote:
"Bonobos was and you know, is a premium brand. [...] you have the best."
— Guy Raz [16:11]
Andy concludes by reflecting on his experiences and the importance of candor and courage in leadership, which have been instrumental in his growth as an entrepreneur.
Notable Quote:
"Just do what's right for the company. I'm going to say what's on my mind."
— Andy Dunn [54:13]
Episode Highlights:
- Andy Dunn’s journey from co-founding Bonobos to launching Pie.
- Overcoming mental health challenges and integrating personal well-being into business strategies.
- Strategic advice on marketing, pricing, and scaling for emerging entrepreneurs.
- Real-world applications of wholesale versus direct-to-consumer models.
- The importance of adaptability, resilience, and authentic brand storytelling.
For More Information:
- Listen to Delightful Episodes: Check out Andy Dunn’s previous episode on building Bonobos for a comprehensive understanding of his entrepreneurial journey.
- Join the Conversation: Entrepreneurs can participate in future advice lines by calling 1-800-433-1298 or sending a voice memo to hibtid.wondery.com.
Produced by: Catherine Cipher
Music Composed by: Ramtin Arablouei
Edited by: John Isabella
Audio Engineer: Sina Lofredo
Production Staff: Alex Chung, Elaine Coates, Casey Herman, J.C. Howard, Iman Maani, Chris Massini, Kerry Thompson, Neva Grant, and Sam Paulson.
Listen to How I Built This: Available on the Wondery App, Apple Podcasts, Spotify, and exclusive early access with Wondery+.