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Brooke Waupsh: “Always be listening”

Always be listening. It’s easy to be prepared with what to say, and miss what a customer, a potential investor, a college is really saying. If you have the intent to truly listen, you will uncover real insight that significantly impact your business. As a part of our series about strong women leaders who are […]

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Always be listening. It’s easy to be prepared with what to say, and miss what a customer, a potential investor, a college is really saying. If you have the intent to truly listen, you will uncover real insight that significantly impact your business.


As a part of our series about strong women leaders who are shaking things up in their industry, I had the pleasure of interviewing Brooke Waupsh, CEO and Co-Founder, Swoovy (www.swoovy.com)

Brooke is an award-winning marketer with experience breathing life into established brands such as Coors, Clorox, and Charles Schwab, as well as successfully introducing a new financial technology consumer brand, Kasasa, to the market that is now nationwide and supported by the 4th largest network of financial institutions behind Bank of America, Chase, and Wells Fargo. She was nominated for “Change Maker of 2019” by the Austin Young Chamber as well as a finalist for the Austin Under 40 awards the past 2 years for “Start-Up and Innovation”. Her industry awards include a Bronze Los Angeles Addy Award (Regional/National Television category), 5 MarCom Awards and 2 Honorable Mentions. She also has numerous industry certifications including Graphic Design (UCBerkeley) and Agile software development.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I’m an Austin-native. I’ve always been very driven and entrepreneurial. I graduated high school and college early, working multiple jobs and financing college on my own. After college, I took the big leap and moved to San Francisco and took a job with a prestigious ad agency, DDB Worldwide. I’ve spent close to 20 years in marketing and brand strategy, breathing new life into established brands like Coors, Clorox, and Charles Schwab, and also had the opportunity to lead the launch of a new financial technology brand and take it nationwide — Kasasa.

After being a key member in launching the new FinTech brand in 2009 that helped community banks and credit unions compete against megabanks in 11 markets and growing it nationwide, I realized I had the tick for innovation and building game-changing brands.

In 2018, I brought together two seemingly unrelated worlds — volunteering and online dating. It was an opportunity, that when I took a step back, made a ton of sense and could help non-profits tap into a mainstream audience of people to get them involved, and it could help this mass market of online daters get through their frustrations of not meeting genuine people, having anything worthwhile to do as a date to really get to know someone, and ultimately connect through something meaningful — while still using technology. As it turned out, dating experts recommend volunteering as one of the best ways to meet someone and develop a strong relationship.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Non-profits desperately need a modern way to activate more volunteers. And in the online dating market DESPERATELY needs to infuse a little “good” into the intentions of the market. It’s a world that has grown tremendously, with almost every single person having (or have tried at some point) an online profile. It makes sense to use technology to make things easier and to have more access.

I saw an opportunity to give online daters hope, and an even bigger opportunity for social impact. Volunteering can offset some of the depression people feel in the dating space with all of the swiping, it’s actually proven to have positive effects on mental and physical health. And, each hour of volunteer time is worth $25 to a non-profit. When I started crunching the numbers of those 500 hours a year spent on dating apps, shifting over to volunteering for even 1 date a month, I was looking at what could be a billion dollars of value into the non-profit sector. That had me hooked.

While the dating market made the most sense as an initial segment, partnership is still the hook and the foundation of Swoovy to increase volunteerism. We received feedback after our launch people would love to use the app to volunteer with friends, significant others, as well as groups. It makes it easy to get involved in the community, and strengthen those relationships as well. That validated my vision for Swoovy and is our current roadmap as we expand. We just released a couple’s experience, where, for less than going out to grab coffee together you can set up a joint account to view daily opportunities, invite each other, and book something that works for both of you — a new kind of date for couples to strengthen their relationship, stimulate conversation, and allow you to bond and grow through giving back.

With COVID-19 we rolled out virtual ways to connect, and tested virtual-volunteering group events as well that were very positively received.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Before we launched Swoovy we needed to get early sign ups so we hosted a few happy hours at companies to tell them about the app….and then everyone’s potential matches early on were their co-workers. Oops.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

It’s important to surround yourself with people who believe in you. My previous CFO at the FinTech company I was at was my first investor and an advisor. He has offered business guidance but also takes the time to empathize with the ups and downs of the start-up journey, which he’s been through, and recognize the perseverance.

I was also introduced to Steve Stagner, former CEO of Mattress Firm, during my participation in the Mass Challenge Accelerator program and he has been an amazing mentor. His story is inspiring, starting as a franchise owner of one Mattress Firm store and rising to the top of the entire corporation. He understands start-up and building a company with a long-term vision in mind; his guidance and coaching has been invaluable.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

When you think “disruption” you think of change, break, separate, chaos — which are things that can make people uneasy, or is necessary. Good things come from change. From my past world, financial technology disrupted the space, and was necessary and good. Other examples: cell phones, Amazon deliveries, meal kits for cooking at home; these are all good disrupters. But there are also industries threatened by disruption that need to re-think and innovate or become obsolete. Travel agents, newspapers, tax accountants, book stores, Kodak.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

  • Always be listening. It’s easy to be prepared with what to say, and miss what a customer, a potential investor, a college is really saying. If you have the intent to truly listen, you will uncover real insight that significantly impact your business.
  • Network. People want to help, knowledge share, make connections. I’m constantly amazed of the value of going to networking events.
  • A good idea is just a good idea, it’s the people behind it that make it happen. If you choose to take an idea forward, you have to be all in and also surround yourself with people who are also all in with making the vision become a reality.

We are sure you aren’t done. How are you going to shake things up next?

With Swoovy we have successfully adjusted during COVID-19 to and rolled out virtual volunteering opportunities, an experience for couples to “reconnect” and stay connected from home through service, as well as a membership for groups to easily complete service hours. We’re now working on introducing Swoovy for Friends and expanding into additional cities. People want to do good, but life happens and they get busy. It’s about weaving volunteering in to the way they live, work, and play — and ultimately, in all facets of life partnership and fostering relationships is king.

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

Fundraising. Did you know that only 3% of females receive venture funding even though research shows women-led companies typically outperform other companies by a variety of financial metrics? McKinsey research shares data for women-led companies such as 41% higher return on equity and 56% better operating results. In the venture capital arena, women-led companies translate into less capital requirements and higher returns, but they still do not get the early funding.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

Blue Ocean Strategy is an oldie but goodie that stuck with me as inspiration throughout my career, written by W. Chan Kim and Renee Mauborgne. In blue oceans, businesses create demand rather than fight over it. Despite a long-term stronghold in the taxi industry, Uber has grown faster than any other company ever by reinventing the market. Uber created a blue ocean, they turned non-customers into customers.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“The first step toward success is taken when you refuse to be a captive of the environment in which you first find yourself.”– Mark Caine

Everyone is faced with life challenges, it’s how you choose to push forward and learn and grow from the situation you find yourself in. Two people can be dealt the same cards, and one uses it as motivation to succeed, another who it to be why they did not succeed.

There are many instances in my life that this feels relevant, in high school I had a number of health-related issues I was dealing with and missed a large portion of the school that would have set me back tremendously. I was given the opportunity to make up some of the work in a self-paced program and I not only made up the lost time, I ended up graduating high school a semester early. I didn’t have money for college, but I was determined to go and worked multiple jobs and financed my education on my own — also graduating in three and a half years.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’m working on it with Swoovy. We have the opportunity to be a tide that rises all boats. There are 600,000 nonprofits in the US that rely on volunteers to serve some of the most vulnerable people, animals, and environmental issues in our community. People today are spending over 500 hours a year on dating apps. One hour of volunteer time is worth $25 to a nonprofit and makes a tremendous impact toward society; if you look at just the dating industry, if people would go on just one date a month volunteering we could infuse billions of dollars of value in to the nonprofit sector, not to mention the enormous positive impact on society.

How can our readers follow you online?

https://www.facebook.com/Swoovy/
https://www.instagram.com/getswoovy/
https://www.linkedin.com/in/bwaupsh/

This was very inspiring. Thank you so much for joining us!

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