I received a great email the other day: “Big news, we just landed a total game changer to head our growth. He was formerly with Facebook and Snapchat.”
The message was from Jillian Darlington, CEO and founder of the MomCo app. Darlington is a 35-year-old single mom who entered the startup world after she was inspired by her own life experiences to create an app that help moms connect.
I myself connected with Darlington after she reached out to me through Twitter, thanking me for one of my articles on Entrepreneur.com. She was just starting out and completely bootstrapping her startup. Long story short, my company gifted her firm with an infographic to help out, and she and I have stayed in touch throughout the years ever since.
When I received Darlington's email, I was happy to hear things were going well, especially since, historically, the startup world has not always been a female-friendly environment (and, speaking of history, it is Women's History Month, after all).
So, I jumped on the phone and asked Darlington about her experiences as a female founder in the ultra-competitive world of fund-raising. Here are five key lessons she told me she has learned along the way.
1. You have to be mentally bulletproof.
Fund-raising is like standing naked in front of a plastic surgeon every day and having every single flaw on your body pointed out and magnified, Darlington said. Investors will point out flaws in you, your idea, your team, your pitch—everything.
That is why you have to mentally and emotionally prepare yourself to hear about anything and everything that could possibly go wrong.
While the process is excruciating, it can be incredibly helpful if you do not get defensive. Darlington said she still struggles with these critiques. What's more, investors want to see if you are coachable, she noted. So she just tells herself to "breathe" and reminds herself that these people are actually trying to help her succeed.
2. You have to know whom to talk to.
When you have a brilliant idea, traction and a strong product market fit, it is hard to understand why people are not just throwing money at you. Darlington said she has learned that most individual angel investors have a strict checklist they follow when it comes to startups.
If you do not help them check those boxes, they are not going to give you money—plain and simple.
When she is mingling before a presentation, Darlington said she always asks, "So, what kind of companies do you usually invest in?” If they are only interested in life science companies, there is no reason for her to try to sell them on her company, MomCo, she said.
3. You have to find the right lead investor.
As a woman who has created a platform specifically for moms, Darlington said that the funding process has been difficult, because investors like to invest in something they would like to use themselves—or have experience with. Since the majority of angel investors are men, the number of investors who might be a match for her is very small, Darlilngton said.
In addition, finding a lead investor with connections of his (or her) own is important because the people who respect this person will take interest in you because your lead investor believes in you. Darlington advised finding someone willing to put in the time and effort to help you close the entire round—someone who would not walk away after wiring you his or her investment.
4. You have to learn to roll with the punches.
Darlington typically introduces herself as "Jillian Darlington, the CEO of MomCo," and then explains what her app does. ‘It’s a geo-based social networking app that helps moms find potential mom friends that live close by," she said.
The (typically male) investor she is addressing, however, will then usually turn to the man standing next to him and introduce Darlington as "Jillian—she’s a mom." Darlington said she has to wonder: How many male CEOs who have children are introduced solely as dads?
"This happens at almost every event I go to, and if I didn’t laugh at it, I would look like a very angry woman all the time," she said.
5. You need an incredible amount of confidence.
Darlington says she gets accused of being over-confident all the time—because she is. "If I weren’t, I would have been squashed like a bug by now. When you are raising money, you are selling yourself and your idea. You have to bring it with everything you have and never apologize for being your own biggest cheerleader," she said.
As a fellow startup veteran (and a man), all I can add is "amen."
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