Book recommendations

The Pleasing Appeal of Harry Styles

By Larry Gennari
Boston Business Journal
September 22,2022

Harry Styles, right now the most famous entertainer on the planet, rose to acclaim as a member of the boy band One Direction. His catchy, confessional lyrics, gender-neutral retro style, and upbeat, ineffable charm on stage have made him an icon. The 28-year-old singer-songwriter easily fills stadiums across the U.S. and beyond, and he soon will appear in several soon-to-be released films.

As the dad of a superfan, I’m long aware of his renown. (Harry, remember that small SUV that tailed your tour bus in the Boston area, the one blasting As It Was and Watermelon Sugar, with the girls screaming “HARRY!!!” at every stoplight?… Thanks for not pressing charges.) Styles is indeed a generational talent and with thoughtful choices, hard work, and a bit of luck, his entertainment career will continue its soaring trajectory. Yet, I’m less interested in his next album (Harry’s House is all-around solid; good luck topping that!) and more focused on his entrepreneurial work, and more specifically, his newly launched, eco-friendly, consumer goods company: Pleasing. Building a brand into a business is challenging and I hope Harry will consider a few business-oriented books alongside those new scripts he’ll be reading in the coming months.

Pleasing.com launched last year, starting with nail and skin care products made from sustainable and plant-based ingredients as well as apparel from recycled and organic fabric, some of which was modeled by Mick Fleetwood, another super-fan dad. Harry’s partner in the venture, Emma Spring, is his former assistant. Kudos to Harry for recognizing the power and potential of a woman-co-founder. He and Emma will want to read When Women Lead, the upcoming book by CNBC tech correspondent Julia Boorstin, who chronicles the challenges, qualities, and insights of more than 120 successful women leaders. The book is unique for its breadth, depth and data, and Boorstin’s storytelling of how and why inspired women tend to build strong, purpose-driven companies while establishing new patterns in male-dominated markets, is sharp and insightful. We need more books that challenge set narratives and expand the definition of effective leadership beyond men. Pleasing seems to incorporating some of Boorstin’s “Learning Lessons” already.

Of course, Boorstin and others would advise Harry and Emma not to go it alone or to rely solely on outside professionals, investment bankers, consultants and legal advisors. As Pleasing expands, they’ll need a broader leadership team and advice informed by real experience to scale.  For more on that, they should read Build Your Board, Build Your Business, by economist, investor, and entrepreneur Barbara Clarke, the new, engaging, read-in-one-sitting guide to the basics and benefits of building an effective board for first-time entrepreneurs. Of course, building a board is more than just adding inexperienced celebrities as advisors. Harry and Emma need an intentional strategy of enlisting people who can be true thought partners in their mission-driven strategy. The best board members are selfless, honest, objective, experienced, loyal, and along the way, willing to engage in healthy, necessary, and uncomfortable conversations about operations, money, and growth. For more on that, I’d recommend the new second edition of Startup Boards: A Field Guide To Building and Leading An Effective Board of Directors, by author/ venture capitalist Brad Feld and entrepreneurs Matt Blumberg and Mahendra Ramsinghani, especially the chapters on board recruiting, relationship dynamics, and critical differences between advisory boards and “real” boards of directors. Also, Harry should call Rihanna. She’s busy with her billion-dollar Fenty cosmetics line, but she certainly knows the industry and may have time to be on Pleasing’s board.

Finally, although Harry is continuing his ambitious tour through New York, Austin, Chicago and then Europe, he and Emma will need to remain in close contact about Pleasing’s operations, product development, and marketing support for aligned non-profits. Founder communication shouldn’t be delegated to third parties or left to an email or text from a private plane. Harry should read The Art of Conscious Conversation, the incisive upcoming book by communications expert and mediator Chuck Wisner, which offers practical tips on listening, reflecting, and collaborating with team members, business partners, and family. Given that Harry’s lyrics tap the emotions beneath the surface of common conversations, this book is a must-read for him. He’ll definitely need more Late Night Talking.

Pleasing seems to be off to a good start in a crowded, competitive space.  Fortunately, Harry is a daring original, willing to try new approaches that get noticed. Going forward, that’s undoubtedly what will matter the most.

Read in the Boston Business Journal

 Authors & Innovators is an occasional column by Larry Gennari, a transactional lawyer, law professor, and chief curator of Authors & Innovators, an annual business book and ideas festival.  Gennari also teaches Project Entrepreneur, a business fundamentals bootcamp for returning citizens, at BC Law School.

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