Dynamic Duo: Matthew O’Leary and Janet Wallace

Ms. JD is on a mission to interview power pairs--best friends, sisters, spouses, and business partners--who suport each other in life and/or work. We asked our former VP, Janet Wallace, and her partner, Matthew O'Leary, about their business partnership.  

1. Tell us a little about your relationship.

Janet: We co-founded O'Leary Wallace LLP

Matt: We're co-founders of a trusts and estates law firm. We're also libation confidants.

2. What brought you together?

Janet: We were at a local bar function where two attorneys were presenting on disruptive innovation in law practice. These two attorneys were running a successful firm with low overhead through the use of new technologies. After the event I gave Matt a little wink and a look that said "maybe we should start a firm?" 

Matt: Janet and I knew each other from attorney events and professional mixers because there were not many other young-ish local attorneys in our focus practice areas. Like Janet said, we then had mutual friends who blazed the trail by starting a firm the year before us. We watched them and thought, "Hey, we could do that!"

3. What keeps you together?

Janet: That we built something good together. Also: honesty, mutual respect, and a fair amount of fun. 

Matt: We have some key things in common: We really enjoy our work and the clients we serve, and we are both slightly embarrassed by how easily our clients can make us tear up with them. 

Janet: It definitely helps to not cry alone. 

4. What have been your biggest challenges in working together and/or supporting one another?

Janet: We have two locations, so we are not always in the same place. Sometimes it's hard to be supportive from a distance. Lots of phone calls and texts help! 

Matt: We designed our firm to utilize technology and ​a hands-on approach, not support staff. It presents the challenge that we efficiently support each other by sometimes doing tasks for each other that the ​paralegal's secretary's intern would do at a Big Law Firm.

5. Do you have any techniques or advice for successfully supporting or working with another person?

Janet: Yes! Gratitude! I think Matt and I both recognize what the other contributes. Matt does so much every day--big and small things--and I am so thankful for him. That said, I definitely don't verbalize my appreciation as much as I should. He's one of my favorite people. 

Matt: It's crucial to recognize and appreciate what your partner does for you (reciting all I'm grateful for about Janet would make this answer very long and probably boring for you to read). It's also ​important to appreciate that your colleague is different than you, with different skills, methods, and characteristics. T​hese differences should be admired and utilized, not fought against. Beyond being appreciative and showing it, communicate honestly and openly. Hard feelings develop when things go unspoken so address issues early! 

Janet: I decided early on that we were going to be best friends, whether Matt liked it or not. I mean, if you are gonna spend that much time with a person, you want it to be someone you like and respect, right? Right.

Thank you, Matthew and Janet!

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