How a Goldman Sachs VP from Michigan wrote a best seller
Lindsay MacMillan was a Goldman Sachs VP. And then she published “The Heart of the Deal.”
Yes, the title is a (romantic, mind you) pun on Trump’s “Art of the Deal”, and maybe it was intentional - but she definitely doesn’t shy away from the idea. “I always smile on those comparisons. Because it’s the best PR play to have the association of the prior one,” she told Dean Thomas’ podcast. Thomas is a former colleague of MacMillan’s, from both college and Goldman Sachs, who hosts the “Modern Times with Dean Thomas” podcast, interviewing various tech and finance luminaries.
MacMillan spent six years in total with Goldman, mostly in marketing, and mostly in New York, before she asked the bank to transfer to London, where she worked on Marcus, the firm’s (ailing) retail bank.
Corporate America started as a stressful time for MacMillan. Young people “Feel the societal pressures that there are certain timelines or deadlines,” especially in their romantic lives. “I think that, really, that stress spiral does not serve us,” she said.
Differentiating between a corporate role and one’s personal life was also difficult. “I felt so uncomfortable even seeing myself in a suit,” MacMillan said. She found her creativity a strong way to emerge from the disconnect; “I would wear my commuter sneakers to work, and then I would put on my heels – I called them my Hollywood shoes,” she explained.
“I guess it was the writer in me always creating characters. But I really created a character for myself where I thought “okay, I am in character now. I am competent. I'm financially savvy. I know how to play the game. I know how to go through the system,” she said. “I felt like I was in survival mode for my first year.”
She joined Goldman from college - graduating from Dartmouth, where she studied English. Despite joining the biggest and baddest of the world’s big bad banks, writing was her goal all along. “I would have done that right out of Dartmouth if I’d gotten book deals,” she says. “I just kept getting rejections. I got hundreds of rejections. I wrote four books than never got published before my first book.”
Dartmouth made her a better writer, but it didn’t help her become a published one. Thinking about the commercial side of being a writer was seen as a negative, she says, and her lecturers saw the business side of writing as “tainting the art.” An interest in money was seen as disparaging. “That’s not what writers do, honey,” she remembers.
She credits her career in finance as a “gift,” and notes that it led her to a “great network” of people who eventually sponsored large parts of her work. She calls her way of bringing her book to launch as “authorpeneurship,” and credits her success to self-discipline.
The discipline of prepping problem set weeks in advance of other students “just to hold [her] own in an ivy league school” planted the seeds of fortitude she needed in her writing career. “I was always writing on the side. I would wake up before five in the morning and write for two or three hours before work pretty much every day - and that's discipline,” she said.
The finance industry was supportive when she decided to transition to writing. “These really great businesspeople came around me and really helped me stand on their shoulders,” she said, including Gregg Lamkau, Goldman’s former head of investment banking (and golf fan). “That to me had so much of a - from the sales data too - so much of a higher ROI than just going to your local bookstore, or Barnes and Noble,” she said.
She also notes that authors of good books can find themselves falling flat on their faces due to a natural introversion or a fear of business. She recognises the “privilege” she has “by getting those business experiences.”
Publishers have a “very interesting” business model, MacMillan says. “If they don't trust that you can sell your book yourself, no matter how good the book is, they're not going to take a chance on you. It's very risk averse.”
She left London and moved back to her hometown of Kalamazoo (allegedly a real place) as the date of her book launch approached, and after a while found a job with Sleeping Giant Capital, a local private equity firm.
She emphasized her work-life balance when applying for a job with the fund. “My writing is not just a hobby, it’s a career as well, so I need to allocate the time and the energy to that,” she told HR, who seemed to have listened. “They’ve been super wonderful about being flexible and really job-crafting this role for me to have it be this balanced,” she said.
“I've worked too hard to get where I am to then have that kind of freedom and flexibility taken away.”
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