Few entrepreneurs can tell you more about the grind that is startup fundraising than Jean Brownhill. An architect by training, Brownhill is the founder and CEO of Sweeten, a technology platform that lets anyone find, hire, and pay general contractors. Sweeten manages the bids, placing them in apples-to-apples formats for easy comparison, and even suggests project milestones for payment. Contractors pay a commission when they get a job through Sweeten (6 percent of the first $100,000, and 2.5 percent above that).

Brownhill knew from the beginning that she would need outside investors to build the platform. She started with $250,000 from friends and family, which took two years to raise, mostly in $2,000 checks. For her first institutional round, she met with 257 investors before raising $7.84 million--one of the largest rounds ever raised by a black woman.

Along the way, Brownhill realized that her perception of how a leader should act had become a stumbling block. It took a lot of stress, rejection, and frustration, but ultimately she realized the importance of authenticity in the fundraising process. By changing the way she interacted with investors--and the way she communicated those interactions to employees--she greatly improved her outcomes with both groups. "I was trying to be someone I wasn't, because I thought it was who VCs wanted me to be," she says. "That's not possible. They have to trust you. They're giving you a lot of money, and if you're anything other than completely authentic in your presentation, it will never work."

Early on, Brownhill found herself trying too hard to be like the investors she was pitching, all the way down to the vocabulary she used. At the time she was raising her A round, disintermediation--the idea that customers would use platforms such as Sweeten to find providers, but would then cut out the platform when it was time to make a transaction--was a big buzzword. It wasn't a term Brownhill used with her employees. In meetings with VCs though, she suddenly found herself talking about how she was fighting disintermediation. The result, she says, was "a slight pause that speaks to not being really comfortable and in control of your business."

Brownhill also was wearing clothes that weren't right for her. "There is absolutely a performative element to this, she says, "but it has to be authentic." She came to see that venture capital is actually fairly informal, but with her best corporate dress and heels, she was treating it more like investment banking. "If you dress like that every day, of course dress like that to pitch," she says. "If you're wearing jeans and boots and a sweater most days"--she gestures to her clothes--"that's how you should go in."

Making matters worse, Brownhill would try to hide the stress of fundraising from her team. Of course her employees could tell; it was obvious, and her weight was fluctuating. Eventually, "it was just too exhausting to carry that mask around," she says. "If I was going to get rejected anyways--which I was--I might as well be comfortable doing it."

So Brownhill started dressing in a way that was less formal and more natural to her, ditching the sheath dresses. She stopped using VC jargon. She told her employees when she was stressed. And her pitches improved. "I had a very take-it-or-leave-it energy," she says. "It was, 'This is the vision, this is what we have, this is what we're building. If it makes sense for your business, fantastic. If it doesn't, I need to go back to work."

Investors started responding differently. Brownhill convinced them that she had something of value, and if they couldn't see it, that was their problem. VCs started asking questions about her vision, rather than about her costs to acquire a customer. Now she was selling, rather than constantly being put on the defensive.

Her change in attitude clearly made a difference to her team, as well. Her inability to talk about the stress, she says, had alienated them. Now they felt much more comfortable telling her when they too were stressed out or overwhelmed. "It has speeded up our efficiency in every part of the business now that people aren't waiting for the right time to say something," she says. "I don't know where we got this idea that as a leader, you can't be human."

Published on: Nov 15, 2019