10 lessons from the female founders of Making it Happen, Season 1

When you start a business, there are highs and lows, ups and downs, moments of pride—and moments of weakness. One day you’ll feel extremely successful, the next you’ll feel like a failure. Sometimes you’ll be on top of the world, and others you’ll be at your breaking point.

And that’s exactly what Making it Happen aims to explore in Season 1. 

In this series, Brass Clothing cofounders Katie Demo and Jenny Rudin explore the real stories behind 10 female founders’ success stories. And listeners are given a fly-on-the-wall glimpse into what it’s like to really start and grow a brand.

1 | Doubt will creep up on you when you least expect it

You might expect imposter syndrome to kick in immediately as an entrepreneur, but gr8nola founder Erica Liu Williams says that in her experience, getting started is actually the easy part.

“I really connected with Erica when she was saying imposter syndrome shows up after you’ve just completed a big project—it feels you’re you’re at the top of the mountain and you’ve accomplished this big thing, but there’s actually so much more to go,” Demo says, reflecting on the series. “And you think, ‘Okay, what’s next? Where do I go now?’ That’s when you start doubting yourself

“You have to think about it in cycles,” Rudin adds. “You go up the mountain, you go down the other side, and repeat—as opposed to an epic climb where you realize you’re at the top without a safety net.”

2 | There’s a method to the madness of risk-taking

Taking risks with your business can be scary. But coming to decisions through a methodical approach can help alleviate some of those associated risks. While it seemed like Chelsea Moore took some chances when building BOXFOX, they were actually calculated and well-thought-out.

“Chelsea tried one wholesale opportunity with a big retailer and decided that wasn’t the right move for the business,” Rudin explains. “They haven’t been seduced by these splashy opportunities—instead they’ve taken a slow and methodical approach, thereby mitigating the risk of their decisions.”

“She’s not scared of risk because she doesn’t go into a situation without having the information and without having thoroughly communicated with the people who are also involved in taking the risk with her,” Demo adds. “She’s not doing anything on her own. She prioritizes over communicating, and that can make risk taking more palatable when it’s all out there on the table.”

3 | Know what you want, but manage your expectations 

Many people go into entrepreneurship seeking the freedom that they don’t think they can achieve in a 9-5 job—but it’s not always that simple. Laurel Wells Thompson realized that she wanted to make a difference in the world when she created her brand, Beya Made. As a mother, she also wanted to have more flexibility.

“She thought that it was going to be this opportunity for her to own a business on her own time, and then she could prioritize being a mom,” Demo explains. “But the truth of the matter is that those two priorities are competing with each other all the time, and it’s a common misconception that when you own your own business, you have all of this freedom to do whatever you want, whenever you want.” 

“Laurel proves that you can take your experience, formulate a new idea, and embark on the journey of building a business—all while being a parent,” added Rudin. 

4 | Reframe the idea of asking for help, financial or otherwise

Kim Lewis’s fundraising journey with CurlMix is nothing short of incredible, especially considering that women get less than 3% of venture capital funding—and Black women get less than .006%. But Kim’s ability to pitch her company to investors and her community ultimately came down to one quality: Understanding and communicating the unique value of her business.

“Fundraising is a hard process, especially when you feel like you are asking for money rather than asking someone to invest in your business,” Demo explains. “You have to get out of the mindset that you’re begging for money—women often feel that way as a default, when it’s quite the opposite. You’re giving them an opportunity to come in on something that you’re pouring your heart and soul into—and they’ll benefit from that.”

“You need to have a plan at the outset and manifest the outcome that you want,” Rudin adds. “Start the process of fundraising with a vision of what that end goal is, how much money you want to raise or what your company is worth, and dive in headfirst. There is no time to feel like you’re playing into the hands of someone else—you’re holding the deck of cards. It’s easier said than done, but you have to start with the right frame of mind.”

5 | Find a co-founder who complements you

The differences between Lizzie Carter—who shares a baby with her personal and professional partner, Hugo Lewis, have helped contribute to Only Curls’ success.

“The biggest asset of working with a partner is when you have a difference of opinion—when you have different thoughts on how to tackle a problem—because almost 100% of the time, working your way to a compromise in the middle results in the best possible outcome for your business,” explains Rudin. “When you’re in it alone, you don’t have an opportunity to soundboard with someone who has the same goals as you.” 

“I think the reason why you choose to have a co-founder is to have someone to balance you,” Demo adds.

6 | Customer empathy will allow you to build a better brand

While the diamond industry traditionally has been male-dominated, Olivia Landau was confident that she could disrupt it with The Clear Cut. Landau had one major advantage: Unlike traditional jewelers, she knew her young, female customers on a deep level. 

“Olivia disrupted the diamond industry by owning the business as a woman. She’s better able to cater to other women, put the power of the purchase into their hands, and speak to them directly—which is also what we’re trying to do with Brass Clothing,” says Rudin.

“It’s very interesting when men are at the very top of an industry where females are the customer,” Demo adds. “There’s a chance that what the woman really needs can be missed by male jewelers. We need more women to shake things up.”

7 | Take your time

Too many founders sentimentalize the grind involved in starting a business, while not enough prioritize self-care. But Ashley Rouse discovered in her journey building Trade Street Jam Co that putting yourself first is the only way to succeed in the long-term. 

“As important as it is to have a strategic plan of action and goals, it’s equally important to know when to take a break, to recalibrate, and to recenter yourself,” Rudin says. “Sometimes, you just need to be able to say, ‘I’m done for the day.’ I think people need to hear that the idea that you have to grind, grind, grind doesn’t serve anyone.” 

“When you’re the leader and you’re making all the big decisions, you have to be mentally capable of doing that. And that means when you’re feeling like you’re not quite there, you have to recover and get yourself into better shape. A lot of people ignore that feeling, and when you do, you’re not serving yourself or your business,” said Demo.

8 | Get comfortable with being uncomfortable

Through Seven Starling, Tina Beilinson helps women manage the uncertainty of being pregnant—which isn’t all that different from what entrepreneurs go through. Beilinson navigated the unpredictability of building a business by using the same tools that she uses to equip new moms. 

“Tina’s experience is an indication of how managing uncertainty, creating frameworks, and shifting the narrative when you’re faced with a problem or a disruption to a plan is so important when you’re an entrepreneur,” Rudin explains. “You need to be flexible and you need to be comfortable in uncertainty. When you reach a roadblock, you need to be able to have confidence and figure out a way forward.”

“Having the tools required to manage uncertainty and handle situations like this will ultimately serve you and your business,” Demo adds.

9 | Prioritize learning over being right

Monica Grohne had to pivot more than once when she was building Marea Wellness. She had to find a supplier to produce her product while considering the best business model for her company to implement.

“When you’re changing courses, it’s easy to think, ‘I’ve gone all the way down this path. What a waste of time, energy, and resources,’” Rudin explains. “But consider how amazing it is that you have this intel, information, or customer feedback that’s allowing you to change course and letting you go in the right direction to set your business up for maximum success. You might have never realized how important the change was going to be had you not gone down the wrong path first.

“Each decision leads you to where you should end up going. If you’re able to listen to your customer and take their feedback, each decision you make based on that knowledge will help improve your business in their experience,” adds Demo.

10 | Life lessons will best prepare you for entrepreneurship

Danika Brysha wasn’t always the successful entrepreneur she is today. In fact, she struggled with battling eating disorders, mountains of debt, and deciding on a career path that would bring her fulfillment. Eventually, Danika founded three successful businesses—Model Meals, Self Care Society, and Danika Brysha, Inc.—but it never would’ve happened without some of those earlier challenges she faced.

“Danika used her 20s to try a lot of different things,” says Rudin. “There were a lot of highs and lows. Danika did a lot of learning about herself while grappling with personal challenges. It’s a testament to using the earliest stages of your adulthood to explore, try, fail, get your knees dirty, and fall down and pick yourself back up. But it’s also important to reflect on those experiences with grace and humility and harness what you learned from them to power your business.” \

“Don’t let a good crisis go to waste,” adds Demo. “Those are the moments that you can really learn from yourself, and it’s a gift. Yeah. If you’re able to get yourself out of it, it can be a gift and it can be a lesson that will guide you and make you stronger.” 

What it really takes to make it happen

With every goal achieved or milepoint reached in an entrepreneur’s journey, there are hundreds of lessons learned. This is just a glimpse of everything we learned from the guests of Making it Happen, Season 1—and the many insights they shared into what it means to be a founder.

Interested in hearing more from the guests of Making it Happen? Tune into the podcast.

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