Get All Access for $5/mo

5 Fundraising Lessons From a Startup Founder and Single Mom For example, how many male startup founders always get introduced as a 'dad'?

By Jonathan Long

Opinions expressed by Entrepreneur contributors are their own.


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."

Related: Women Raise More Money With Crowdfunding, Research Shows

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 to help moms connect.

I myself connected with Darlington after she reached out to me through Twitter, thanking me for one of my articles here on She was just starting out and completely bootstrapping her startup. Long story short, my company gifted her company 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 hasn't 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's 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 says. Investors will point out flaws in you, your idea, your team, your pitch -- everything.

That's 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 don't get defensive. Darlington says she still struggles with these critiques. What's more, investors want to see if you are coachable, she notes. 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's hard to understand why people aren't just throwing money at you. Darlington says she's learned that most individual angel investors have a strict checklist they follow when it comes to startups.

If you don't help them check those boxes, they aren't going to give you money -- plain and simple.

When she is mingling before a presentation, Darlington says she always asks, "So, what kind of companies do you usually invest in?" If they are only interested in life science companies, she says, there is no reason for her to try to sell them on her company, MomCo.

Related: What This Female CEO Learned About Gender Bias After Pitching 200 VCs

3. You have to find the right lead investor.

As a woman who has created a platform specifically for moms, Darlington says 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 says.

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 advises finding someone willing to put in the time and effort to help you close the entire round -- someone who won't 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 says.

The (typically male) investor she's addressing, however, will then usually turn to the man standing next to him and introduce Darlington as "Jillian -- she's a mom." Darlington says 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," Darlington says, "and if I didn't laugh at it, I would look like a very angry woman all the time."

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," she says, "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."

As a fellow startup veteran (and a man), all I can add is "amen."

Related: 3 Ways for Women to Close the VC Gender Gap

Jonathan Long

Founder, Uber Brands

Jonathan Long is the founder of Uber Brands, a brand-development agency focusing on ecommerce.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business Solutions

Increase Productivity with This Microsoft 365 Subscription, Now $25 Off

It can make the entrepreneur life a lot easier.

Business News

Apple Pay Later Is Ending. Here's What's Taking Its Place.

The program was available for less than a year.


This Artist Answered a Businessman's 'Powerful' Question — Then His Work Became 'the Poster Child for Juneteenth': 'Your Network Really Becomes Your Net Worth'

Reginald Adams was the executive director of a Houston-based art museum for more than a decade before he decided to launch his own public art and design firm.


Harvard Business School Professor Says 65% of Startups Fail for One Reason. Here's How to Avoid It.

Team alignment isn't nice to have -- it's critical for running a successful business.

Business News

Here's What Companies Are Open and Closed on Juneteenth 2024

Since it became a holiday in 2021, Juneteenth has been recognized by some major corporations as a paid day off.

Growing a Business

I Hit $100 Million in Annual Revenue by Being More Transparent — Here Are the 3 Strategies That Helped Me Succeed

Three road-tested ways to be more transparent and build relationships that can transform your business — without leaving you feeling nightmarishly over-exposed.