Flight Templates are templated flights, or sets of questions, written by some of the world’s preeminent business leaders. With Flight Templates, Balloon users get unparalleled access to seasoned perspectives and proven business strategies across all areas of business, including leadership, product, marketing & sales, innovation, employee experience, culture, and more. This feature is part of a series on The Insight that profiles Balloon’s Flight Template authors.
Aubrie Pagano is becoming the investor she wished she’d had when she was first growing her company.
The founder and CEO of Bow & Drape—a line of customizable apparel catapulted to fame by the likes of Serena Williams, Reese Witherspoon, Spanx creator Sara Blakely, and a barrage of other household names—Pagano left her stable strategy job at Fidelity Investments and started the brand with her best friend Shelly Madick when she was only 26 years old. Back in her founder days, Pagano recalls, she spent years meeting with investors who mistook her youth and interest in fashion for naiveté and frivolity. Luckily for young founders today, however, Pagano joined Alpaca VC as an investment partner earlier this year, with seven years’ worth of firsthand lessons guiding her approach to the founder-investor dynamic.
“I had a pretty terrible experience with VC,” Pagano lamented, referencing the many experiences with subtle and blatant sexism alike that eventually led to her involvement in the #MeToo movement in 2017. “So when I had the chance to join Alpaca, it felt like a real opportunity, post-#MeToo, to be part of the sea change that was already happening.”
Pagano describes Alpaca (formally Corigin Ventures) as a “by founders, for founders” investment firm, with a cohort of partners who were all once founders themselves. That shared experience, Pagano said, is pivotal in fostering a founder-investor relationship that is built upon trust and understanding.
“Being a founder is really freaking stressful. You’re running into walls day in and day out and making no money, and you have the weight of the world on your shoulders,” Pagano said. “Investors don’t live that grind as much, so it can be hard for them to empathize.”
Too often, this lack of empathy causes the founder-investor boundary to be virtually insurmountable. But because she has lived the reality of taking a company from seed to scale to sale (she sold Bow & Drape to Win Brands Group in late 2019), Pagano, instead, transcends it.
After nearly a decade toeing the line between founder and investor, Pagano has accrued quite the wealth of knowledge. Now, Pagano is bringing her sought-after wisdom to more than just those on her exclusive client list: Her three-part flight template series, Startup Recruiting, Pitching, and Planning, gives Balloon users priceless advice on navigating common founder experiences—since she’s seen it all from both sides of the aisle.
When she publicly announced her partnership with Alpaca, Pagano promised “to be good to my entrepreneurs while making sound financial decisions for my LPs.” As someone who has had a few bad ones, Pagano knows the good partners—the investors, the advisors, the fellow founders in the trenches alongside you—can be transformative. She recognizes that “good” looks different to every founder, but Pagano said that a symbiotic dynamic largely hinges on the duo’s ability to connect to each other—not as business partners, but as people.
“To have a successful founder-investor relationship, you have to find your people, but that means you have to be authentic,” Pagano said. “Don’t try to fit into some box of what you think a founder should be. Lean into your style, and you’ll eventually find people you’ll connect with. And look, I had a hundred ‘no’s before I got the ‘yes’s, but the partners that really did understand me were incredibly valuable. That's ultimately what investors are after: Somebody who is real, somebody who is confident, somebody they can trust. And when investors come across someone like that, they’re going to work that much harder to help them succeed.”