Betsy O’Reilly – Co-founder of QuadJobs

I frontload the hardest work when my focus is best, and by the time my morning meetings start I feel like I’ve already gotten a few tasks under my belt.

Betsy worked for 17 years in the banking industry in Chicago, Zurich and London. After working in both trading and sales, she ultimately was made a Managing Director at Deutsche Bank where she ran the global equity sales team. She left banking and then co-founded QuadJobs in 2014.

Where did the idea for QuadJobs come from?

In communities across America, busy households like my own need help with an abundance of on-demand jobs. They need great Saturday night babysitters, tutors, dogwalkers, errand-runners, bartenders, heavy-couch movers, playroom organizers and more. Main Street businesses need reliable helpers to pitch in at marketing events, during the holiday crunch, or with deliveries. These employers need to make well-informed, confident hires. They need to fill jobs quickly and don’t want to be bombarded with ill-matched applicants.

College students are the perfect fit for hyper-local, fast-trading jobs. They need money (85% are receiving financial aid), work experience (82% graduate un- or under-employed and would benefit from a stronger network and resume), and flexibility (shifting academic and extracurricular commitments can make steady part-time jobs challenging). They are a talented labor force and uniquely attractive for many jobs—and yet they’re fragmented and hard to reach.

QuadJobs is the first marketplace to bridge the divide between campus and community, unlocking hyper-local jobs for students and connecting employers to capable, performance-vetted, immediately available help.

What does your typical day look like and how do you make it productive?

I’m an early morning person. I frontload the hardest work when my focus is best, and by the time my morning meetings start I feel like I’ve already gotten a few tasks under my belt.

How do you bring ideas to life?

Collaboratively. I value the input of my creative, experienced colleagues and we bring ideas to life as a team. In many cases, I find we get a better result when others take the lead and I listen to what they have to say. Hearing their views and perspectives helps me form an opinion about the best path for QuadJobs.

What’s one trend that really excites you?

The on-demand labor trend is reshaping the economy—and I feel we’ve captured a perfect niche by focusing on college and graduate students looking for mostly on-demand work. Students value flexibility and independence, and they can’t always commit to regular part-time jobs. They want to work when they can and keep the money they make. QuadJobs is a natural extension of what they’re looking for in terms of work during school.

What is one habit of yours that makes you more productive as an entrepreneur?

I don’t get discouraged easily. Growing up in a close family with eight children, I’ve never had the expectation that everything would go my way—or that having everything go my way was essential to being successful and happy. At work, I tend to see setbacks as part of the game.

What was the worst job you ever had and what did you learn from it?

Dressing up as the Easter Bunny wasn’t a job I would’ve highlighted on my resume, but it was surprisingly fun and helped me to connect to an academic mentor. I’m a believer that even small jobs—even silly jobs!—are valuable at a certain age, for networking and experience.

If you were to start again, what would you do differently?

I loved my career in finance. I gained experience, perspective, and a network of advisers and friends who were instrumental in getting QuadJobs out of the gates. But I know now that my passion lies in being an entrepreneur and building a business from the ground up. Part of me wishes that this chapter of my career had started sooner.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Thank those who help you, and help others any way you can. Entrepreneurs must constantly ask for favors, advice, and connections. It’s important to express your gratitude and to give back whenever you can.

What is one strategy that has helped you grow your business? Please explain how.

Our beta market was Fairfield County, CT. We saw our biggest growth from word-of-mouth, and especially from mothers connecting to friends and telling them how much they loved QuadJobs. We give word-of-mouth a kickstart in new launch markets by identifying influential “connectors”—often Moms—who are at the core of their communities. These “Mombassadors” bring QuadJobs into the fold, connecting us to local events, groups, and press.

What is one failure you had as an entrepreneur, and how did you overcome it?

We try out new ideas that don’t work constantly. One thing I’ve learned is that sometimes the idea isn’t at fault, but the execution—and that we just need to approach it from a different angle.

What is one business idea that you’re willing to give away to our readers?

My son Will had the idea of a site that allows friends to swap recipes with their inner circle, creating a personal cookbook of the meals and treats all your friends and family love most. It’d be to Pinterest what Instagram is to Facebook.

What is the best $100 you recently spent? What and why?

On party help from QuadJobs. They made a class cocktail party for my sons’ school run really smoothly. My husband and I could relax and enjoy ourselves.

What software and web services do you use? What do you love about them?

I’m drawn to all things that buy me time. Freshdirect and Uber are mainstays. I also use Trello to stay organized.

What is the one book that you recommend our community should read and why?

The Creator’s Code by Amy Wilkinson, in which she breaks down the essential traits shared by a wide range of successful entrepreneurs.

What people have influenced your thinking and might be of interest to others?

I follow everyone from Brene Brown to Warren Buffett, Eckhart Tolle to Bill Clinton.


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