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Supporting the Success of Women-Owned Businesses with IFundWomen Founder Karen Cahn

In 2016, Karen Cahn founded IFundWomen: the go-to funding marketplace for women entrepreneurs and all of the people who want to support them through access to capital, coaching, and connections. 

The goal? To create the capital and mentorship opportunities that so many women entrepreneurs lack access to as they start their businesses. Five years since its founding, IFundWomen has changed the trajectory of thousands of women-owned businesses through crowdfunding, coaching, and networking across the IFW and IFundWomen of Color community. 

Squarespace recently partnered with IFundWomen to survey women-owned small businesses and create the IFundWomen x Squarespace Women-Owned Small Business Insights Report, which covers the trends and strategies of women who sell online. 

In our conversation below with Karen, you can learn key insights from that report, plus much more about the IFundWomen community and the current landscape of women-owned businesses. 

SQSP: How did your professional experience inspire your decision to launch IFundWomen?

Karen: My origin story started back in 2007 when I was working in ad sales for a major video platform. I spent my days doing eight-figure deals for male creators—the only group on that particular platform that had “scale.” The women creators were virtually non-existent on that platform at that point in time, so there were no women video creators that I could help create economic opportunities for. This did not sit well with me at all. 

So, after a ten-year stint at that tech company and a three-year pitstop at another one, I decided to become an entrepreneur and build “it”: a social video platform for women by women where female creators could monetize their content through partnerships with big brands. 

Long story short, I failed. 

 We made all the rookie mistakes: investing in supply (i.e. technology) before proving demand or doing any customer research, taking too long to get our MVP out because I wanted every cool bell and whistle from the jump—and we were late to market. We had no idea what we were doing and were anything but a lean startup. 

That said, the main reason we failed so fast was because of the lack of funding. As an “all women-founded team,” we didn’t have the luxury of getting hooked up by our VC buddies with a $1M seed check because we had a dope idea and a cool pitch deck. 

So, as a hail mary to save the company, we crowdfunded and very quickly learned how valuable this alternative funding option was for women. At that point, the light bulb went on: Crowdfunding is simply sales and marketing, and if we could do it, we could teach it. So we did. 

We sunsetted the failing startup and started IFundWomen in November 2016 using a Squarespace website! We were definitely early Squarespace adopters—it was so easy for us to prop up our MVP without knowing how to code. Now, five years, 29 employees, and 250,000 members later, I spend each day at IFundWomen alongside an incredibly dedicated and passionate team, working to close this funding gap for women entrepreneurs through four products: from crowdfunding to enterprise grants to IFundWomen of Color to our proprietary edtech that we built to teach women “how to fish.” 

SQSP: Can you share some examples of how IFundWomen has made an impact on women entrepreneurs in the early stages of launching their businesses? 

Karen: We just released our five-year impact study where we looked at 5,000 entrepreneurs who started their funding journey with IFundWomen at the idea stage—the earliest stage of their business. In the first five years of IFW’s existence, we have empowered these businesses to raise over $135M in capital that they would not have access to otherwise, and importantly, these businesses have created 30,000 new jobs for our economy. This is our impact so far, and we’re just getting started. 

I speak often about the entrepreneurship journey: It’s a long and lonely road, and nobody should have to go it alone. It’s for this exact reason—and because of the lack of funding women get—that we developed products that address all of the issues that entrepreneurs face as they grow and scale: funding, education and coaching, community and support, connections to banking relationships, corporate partners, and follow on capital to help continue to fuel their growth.

One of my favorite success stories to highlight is the story of Kalilah Wright, Founder and CEO of Mess In A Bottle, a D2C lifestyle brand that designs clothing featuring messages that evoke change, give a voice to the voiceless, and create a community of unapologetically authentic humans. Kalilah’s story is the epitome of #WhyIFundWomen.

Over four years ago, Kalilah opened her brick and mortar store in Baltimore, and shortly after opening, she was robbed at gunpoint and held hostage, while her newly built studio was stripped of all of the computers and equipment she used to make her products with. The experience was so traumatic that she was ready to give up, sell just enough product to pay her employees, then close the business entirely. 

After the robbery, I heard of Kalilah’s story through a friend and immediately felt compelled to text my friend, get Kalilah’s phone number, and call her to offer support. Thankfully, she picked up, and I was able to tell her directly that IFundWomen was here for her to help her raise money to move into a new, safe studio and repurchase her equipment. Having been through trauma myself, albeit vastly different, I did not hard sell Kalilah on doing an IFW campaign. I simply wanted to offer emotional support and offer a solution if she wanted it. She took a beat, thought about it, socialized the ideas with friends, and got up her courage and did it. 

Kalilah raised $15K crowdfunding to move into a new studio and start production again. She enrolled in therapy. She started to gain her confidence back, and she entered the IFundWomen Maryland pitch competition, got on stage, and crushed the competition—winning an additional $10K of funding. These two instances—combined with Kalilah’s devoted customers who love her products and her own grit—propelled her business to hockey stick growth, opening her up to win multitudes of grants, a television show, and many other accolades. Today, Kalilah’s products are in more than 1,400 big box retail stores, and are worn by major athletes and celebrities.  

There are so many touching stories of how IFundWomen has affected peoples’ lives. Sometimes, people just need another person to see them, believe in their mission, and encourage them to keep going. This is what sets IFundWomen apart and drives our #1 KPI, which is to get as much funding into the hands of women entrepreneurs as possible. There’s simply nothing we cannot do with the right funding and resources we deserve, full stop.

SQSP: Squarespace recently commissioned IFundWomen to create a women-owned small business insights survey. How do you think surveys like this one can provide support to the growing community of women entrepreneurs?

Karen: In September of this year, we teamed up with Squarespace to amplify a shared mission of providing women entrepreneurs with the tools they need to go to market, sell their products and services, and grow successful businesses online. 

We launched in the fall with a customized workshop series led by IFundWomen expert coaches and Squarespace Circle members. All of the content was developed to provide digitally-enabled woman-owned businesses with the resources they need most in order to grow, sell more, and optimize their digital presence. The content covered everything from boosting your social media presence to creating your brand identity to developing your online sales strategy. All of it can still be accessed on our hub today

One of IFundWomen's core values is that we make data-driven decisions, and Squarespace has been the perfect partner to further embody this philosophy. As women entrepreneurs are getting back to business, they are embracing ecommerce like never before and leveraging platforms like Squarespace that offer everything to sell anything

In December, IFundWomen launched the IFundWomen x Squarespace Women-Owned Small Business Insights Report, which presents valuable trends amongst women-owned businesses that demonstrate the value of selling online for women entrepreneurs. Through this report, you will learn about the tools that help women-owned businesses transact online, the priorities and areas of inspiration for women founders, and the sales strategies and focus for women-owned small businesses. 

It’s data-driven reporting like this that helps us identify valuable trends and patterns such as:

  • 81% of respondents who were not selling online before the pandemic are now selling online. 

  • 57% of respondents who sell online are planning to expand their product offerings as one of their biggest business goals. 

  • 63% of respondents are prioritizing making their businesses more environmentally sustainable this holiday season. 

SQSP: Your personal brand is rooted in a “no-BS approach to getting new businesses and products off the ground.” How did you identify and develop that approach as your brand?

Karen: For centuries, women have been taught to keep our mouths shut and smile, be pretty, sweet, kind, don’t talk about money, beat around the bush, etc. What I’ve seen is that nothing is accomplished when you are not direct—us women have to untrain ourselves to do this, so I don’t think I’m any more “no-BS” than any male CEO is. I’m just a CEO. I was never treated any differently for being a girl while growing up. I grew up with a brother and played with the boys on my block. This stance is something that just has always come naturally to me. If women aren’t direct with one another and provide each other with transparent feedback and support, we are never going to make any progress.

SQSP: What’s your best advice for women entrepreneurs who want to start their own businesses? 

Karen: I’ll share two of my best pieces of advice: 

#1: Your network is your net worth—this is the holy grail. 

Over the past five years, I’ve leveraged our incredible network of supporters, investors, and board members more times than I can count. Why? Because—why not? Why would I not take advantage of brilliant people in my life, most of whom are successful women entrepreneurs, who have been-there-done-that and can pay their wisdom forward to me at the moments when I need it most? That resource, my friends, is priceless. This is the secret ingredient everyone talks about, but most seldom take advantage of: the sheer value of your network. 

Let me also acknowledge my privilege to have access to a network at all, while women of color who own businesses face even greater obstacles to accessing funding, mentorship, and community. This, of course, is why IFundWomen’s founding team member, Olivia Owens, created IFundWomen of Color (IFWOC)—the leading platform for women of color to raise debt-free capital through crowdfunding, grants, expert coaching, and lucrative connections. IFWOC is the epitome of access that drives action, broadens networks, and provides the resources that WOC founders have been denied for centuries. 

I don’t even have the words to describe IFWOC’s value, but I do have data: For the first three years of funding on IFundWomen, the 70% of founders who self-identified as WOC raised 30% of the funding, while the 30% of white founders raised 70%. Olivia proudly launched IFWOC in Jan 2020, and in that first year of IFWOC’s existence, we brought the cumulative funding volume over the previous four years up to parity, with WOC founders having raised 51% of the cumulative funding over the previous four years. This is the type of impact Olivia, myself, and our team are laser-focused on continuing to make, so if you are a woman of color entrepreneur who is going at it alone—join us at IFundWomen of Color.

#2: Do not go into debt funding the early stages of your business. 

When people have their big business idea, what’s the first thing they do? They get all excited and start buying things for their business to “get it started”: simple things like business cards, or all the way up to buying fabric or materials for their first line, or even more expensive things like hiring developers to build them a website. Simply put, entrepreneurs go into debt before they even know if they have a business that people want to buy into. 

Don’t do that. Instead, if you crowdfund, raise the cash you need to start up, and then you find out that nobody wants what you’re selling, it’s okay! You are not in credit card debt and you can go onto your next big idea. Even better, you will probably find out through crowdfunding that people actually do want what you’re selling, so you’ve started to generate customers and revenue without having to put up your house to get a bank loan to do it. Hooray for debt-free funding through a demand gen exercise like crowdfunding!

SQSP: A big part of IFundWomen is giving investors the opportunity to easily fund women entrepreneurs. What’s your best advice for people who want to become startup investors?

Karen: The truth is that businesses founded by women deliver two times higher revenue per dollar invested than those founded by men, making women-owned companies better investments. 

We also know that there are over 1,800 new businesses started each day by women in the U.S, and women-owned businesses are growing 4.8x faster than the national average. What this tells us is that the smartest move you can make, for your own portfolio and for the economy at large is investing in women-owned businesses.

For those who want to become startup investors, the best way to start is by creating your own “Angel Investing” thesis. Here are a few key questions to answer that will guide you to the startups to fund:

  1. What problem do you want to see solved in the world?

  2. Which founders are working on solving this problem?

  3. Do you believe in the founder and the founding team? Do they have the expertise to pull off building the business? 

It’s pretty simple actually. I’ll give you an example: IFW partners with venture capital funds who are looking to put money into the hands of our members. One of the partners from our network of VC funds immediately related to an IFW member’s core mission because the problem our member looked to solve was clearly stated and had directly impacted the VC partner himself as a child. The VC fund is now looking into making an investment into this company. 

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