Author Confessions: Samantha Greene Woodruff

On her second novel, her many jobs before writing and her greatest day in publishing.

I first met Samantha Greene Woodruff (Sam) a few years ago when she asked me to blurb her first novel, The Lobotomist’s Wife. We realized we lived close by each other and after becoming instant friends, we decided to start a writing group with another author buddy, Jackie Friedland. Sam’s second novel The Trade Off (out on October 8th!) began as a gem of an idea that she shared during one of our writing groups. What fun it was to watch her develop the story, and the finished copy is sparkling.

Historical fiction fans, listen up. This is the kind of book we all love. Strong female protagonist. Fascinating point in history. An ending that hits just right.

The Trade Off is about a poor, young Jewish woman named Bea living in 1920s New York who happens to have a gift with numbers. With dreams of trading on the stock market, she and her golden-boy brother partner up as a secret team; she’ll be the brains behind the broker. They make a mint, and her family fortunes soar. But when Bea notices negative patterns in the markets, she can see a catastrophic crash on the horizon—and she worries her family will lose everything.

Welcome, Sam, to Dear Fiction. We’re so excited to hear more about this book!

I always love to hear the flash that led to the idea. How/when did The Trade Off come to you?
It started with an event in the stock market in January of 2021 – the Game Stop “short squeeze.” Basically a few successful hedge funds were short the stock of failing video game retailer Game Stop, and a group of amateur investors banded together on Reddit to drive up the stock’s price and take down the hedge funders. It got personal, at least one of the hedge funder managers was being maligned in memes and even receiving death threats.

I was stunned by the way things unfolded – the hedge fund guy was still a human being. He wasn’t some nefarious villain. I realized that people tend to be reductive when it comes to thinking about wealth and character: people assume rich equals bad and poor equals good. It’s obviously more complex than that, and I wanted to find a way to explore it in historical fiction.

Then my husband told me about an investor who famously shorted the Great Crash of 1929 and made a fortune, and I had my idea. Could you short the greatest financial catastrophe in modern markets and possibly not be a villain?

Did your research inform the story or did the story inform the research?
With my first book, The Lobotomist’s Wife, I generally knew where the story was going and used research to gain enough expertise in the subject matter to write about it legitimately. This time, once I began my research, the whole story changed. First, I had hoped to base my protagonist on the investor I mentioned above, a man named Jesse Livermore. Livermore is extremely well known and respected in finance circles for developing revolutionary trading strategies that made him a very wealthy man. But, as I read more, I quickly learned he was also the classic Wall Street scoundrel. He couldn’t be my protagonist.

I had this idea that my investor would be more likable as a woman, and I love to write about strong women fighting for their place in man’s world. So, I created Bea. What I didn’t know until I started researching women in finance in the era, is that there were almost no women actually working with stocks on Wall Street. The women who worked there were either clerical workers or had back-office jobs.

It was also unheard of to be a woman on Wall Street and be poor and Jewish.  All of these things both became obstacles for Bea to overcome and also key historical facts that I wanted to share with my readers.

So fascinating. I’ve also been very wowed by all of the different careers you’ve had. Tell us about how those experiences shaped you as a person and a storyteller. 
One of the things I’ve learned across my many jobs, is that certain talents are transferrable. I’ve worked as a photo editor for coffee table books, a market researcher for a media conglomerate, a business development and strategy executive for the same company, and even a yoga teacher.

Across these VERY varied jobs, there’s been a through-line: I love (and think I’m decently good at) taking complex and disparate ideas and turning them into a cogent narrative. Whether arranging photos on a page, creating charts to illustrate consumer behavior or crafting five-year plan presentations, I was always telling a story.

I learned how to tailor my message to different audiences and distill complex concepts into digestible nuggets. So even though from the outside it looks like my career path has been like a pinball in a machine, I think it led me nicely to where I am today.

What are you most nervous about when it comes to coming out with your second book? Have you ever had a crisis of confidence as a writer?
What am I not nervous about?  The first time, I had no idea what launching a book would look like. I had anticipatory anxiety of the unknown, but I didn’t have any expectations.

This time is different. Now I’ve been in this business for a few years. I have relationships with wonderful other authors (like you), with readers who liked my first book, and with bookstagrammers, bloggers and booksellers. What if they think the book is boring? What if they hate it? What if no one buys it? The process of writing this one was really intense because I was on a deadline and there were loads of revisions. I feel proud of the finished product but…what if I’m wrong and it’s actually terrible?

I think I have crises of confidence about my writing all the time. The other day I was feeling intense imposter syndrome and decided to self-flagellate by reading all the one-star reviews for my first book on Goodreads. It was not a smart way to get psyched up for a second launch!

OMG, Sam. So relatable, but that’s the surest way to feel worse. I always read the bad reviews of some of my favorite books. Somehow it always makes me feel better! Last question. If you could relive one day in your life as a writer, what would it be--and why? 
The day I got an offer on my first novel, The Lobotomist’s Wife. Other than my wedding and the birth of my children, I think it was the best day of my life. I started writing that novel as a hobby, selling it hadn’t even occurred to me. Of course, once I was deep into writing I started to hope that, somehow, it might get out into the world; but I was not a career writer or life-long aspiring novelist. So, the idea that I wrote a book, and someone actually wanted to publish it – to pay me to publish it – it was the greatest feeling of personal accomplishment I’ve ever had.

I know that feeling well. Good luck with the launch next week, Sam! You can preorder her book today at Amazon.com or get a signed copy here. Also, check out her calendar of events. She may be coming near you!