Spotting the North Star
A career in startup storytelling: A post probably better suited for my diary
Gather round. Put everything down. I have an announcement. I figured it out. My “thing.” The thing I want to do. The thing I’m pretty sure I’m going to be good at. I know, I know…you’ve been waiting for this day too.
But hold tight. First, let me tell you a story.
*The Babysitter Stories Part*
Tucked into her pink trundle bed, Allie giggled, “Mommy, Lulu the dog and Santa!”
“Flying. Green. And stinky!” Kathryn exclaimed, joining her younger sister in laughter.
This was in response to my ritual bedtime request — “give me three characters and three words and I’ll tell you a story.”
I was the babysitter, somewhere midway through high school. I discovered, after fighting through whines and excuses and tantrums, that nothing got a 6 and 8 year old more excited to go to bed than the thrill of a story created just for them. They’d dutifully brush teeth, get into p.j’s and tuck into bed in anticipation of another ten minute-long whimsical adventure. I’d go home a few bucks richer and feeling like a genius. (I think we’d call that a babysitting hack now — someone start that blog please.)
*The Other People’s Stories Part*
Fast forward a handful of years and I came around yet again to the power of and perhaps my knack for stories. In my early 20s, in New York City, I was unsatisfied with my low-paying media job and entirely frustrated by my inability to figure my shit out. Other people seemed to have a “thing” or at least they faked it masterfully. I should talk to those people.
So I started asking people to lunch. Interesting twentysomethings who’d found their “thing.” Turns out, if you ask, people are excited to tell their story most of the time. Even the most badass people. And it also turns out, people really like hearing stories. The human stories behind the things that matter to us. FastCompany even helped distribute my stories. I called the company shatterbox.
Dozens of video vignettes later I’d learned, captured and shared the stories of journalists, filmmakers, artists, designers, scientists, and…(long pause for effect)…startup entrepreneurs. I didn’t even really know what that meant before. A startup entrepreneur.
They sold cereal and slept on air mattresses, they quit business school and comfy jobs and they built and failed and built and failed again — all for an idea that they believed, with the utmost conviction, should exist. That’s a story I can get behind. And it’s a story I wanted to be a part of.
*The SF Migration Part*
Inspired by these founders and their startups (and unsure how to scale my fledgling little passion project), I moved to SF to learn more about this nerdy, sexy world. I jumped into a role at higher ed startup and learned how things work, and sometimes don’t work from inside. Then I took several months to try my hand at another little startup of my own but decided not to pull the trigger — story for another day.
I felt that familiar restlessness reminiscent of the New York years — I guess I can do a lot of stuff, but what’s my thing? What’s my story? Then came Tradecraft. A three-month training program that builds non-technical startup skills as well as a world-class network of mentors. A sandbox to ask questions, take risks and nosedives, and at least for me, to discover a passion.
*The North Star Part*
Three weeks ago I found myself sitting across my dining table from a new friend. I’d invited her over for dinner (Thai take-out), admittedly with a professional pep talk in mind. She has a very cool job at an innovative VC fund, which isn’t a coincidence — she’s smart and awesome. I rambled on about my recent geek-out over the world of presentations and startup stories. I’d fallen into a rabbit hole, studying killer communicators and great speeches for a presentation at Tradecraft. It thrilled me. That day I’d met Chris Ott from Duarte, the motherland of presentations, and I couldn’t shut up about it. She waited for my word storm to end, god bless her and then she said, “It’s so ironic you’re saying all this. We’re opening up a role called the lead story role. It might be perfect for you.”
What day is it? April Fools? Don’t toy with me. But she wasn’t. It’s real. A person who’s paid to refine the story of startups — the mission, vision, traction, challenges. Optimizing their portfolio’s pitch decks for fundraising and coaching founders to knock the socks off investors.
(record scratches)
WHAT?!
North star spotted.
Dream job located.
I prepared for five days straight. I embarked on a project to impress — revised a real startup’s pitch deck, built a new script, mapped out a whole epic process. And I didn’t get the job. And it’s okay. I need more experience. My own method. A portfolio of stories built and told. And whatever it takes, I’ll get that job. Eventually.
*The Future Part*
So this marks my promise to this passion. I’ve been a generalist in a world that values expertise. And now I’ve taken the plunge to deepen my skills as a startup storyteller. Nancy Duarte’s “Resonate” sits beside me as I type. As does Carmine Gallo’s “Talk like TED.” I’m pouring over articles and videos about presentation styles, legendary speakers and pitch tips from pillar investors. Kurt Vonnegut’s rejected thesis on story shapes is in one of my open tabs. I’m so excited. I don’t even want to watch House of Cards. (Lie. I do, but I won’t……I probably will later.)
Nancy Duarte says, “Your food, drink, vehicles, books, schools, entertainment, tools and a appliances all came from someone’s dissatisfaction with the world as they found it.” Those dissatisfied people made things better not just by having an idea but the ability to inspire and show people a better way. Smart companies don’t sell products or services, they sell better, faster, funner lives. Which is why you don’t hook investors with raw, rambling data and techie buzzword jargon. Getting fuel for that vision involves taking people on a journey — sharing a problem and helping them visualize a world without that problem.
This is the human side of business. It’s the part we can all relate to. Stories connect us. Stories help make sense of complex data, financial forecasts and the infinite promises of technology.
A really good story also gets the kids to go to bed. Babysitters — you heard it here first.
This Medium collection exists to gather startup stories and to be a home for disparate musings as I wander the world of storytelling. Feel free to hang out.
