Managing Madness with a Mentor: Meet Jessica Vittorio, Managing Partner at The Law Offices of Jessica Vittorio

Jessica Vittorio gives advice on getting plugged into the entrepreneurial community as early as possible, thinking of surviving as an achievement, and being patient with the process.

In this weekly column, CEO of The DEC Network, Bill Chinn, interviews a “celebrity mentor” that is currently participating in the organization’s Fast Start Mentoring Program. The program matches tenured business leaders who have handled crises before to small business owners struggling to navigate the COVID-19 crisis.

This week, Bill Chinn spoke with Jessica Vittorio, Managing Partner at The Law Offices of Jessica Vittorio, to get actionable advice for small business owners and entrepreneurs including getting plugged into the community as early as possible, thinking of surviving as an achievement and being patient with the process.

Bill Chinn: To start things off, what have you been up to as a mentor?

Jessica Vittorio: I mentor for probably eight to ten different organizations, but a lot of them are short term programs, like an accelerated program where you only get to work with a mentee for six to eight weeks. In the Fast Start Mentoring Program, I have been mentoring someone for two or three months now and that’s been a great experience. It was a fun and unique experience to get to follow this mentee as they stepped into a new role and a new position, and I got to consistently check in with them as they made decisions, tried to implement new things, ran into problems and all sorts of stuff.

I’ve talked to a handful of mentees out of the program now and some of them want legal advice since I’m a lawyer—which I’m happy to give—but for the most part, they are looking for general insight about the community and how to get connected as well as having someone to bounce ideas off of as they make decisions. It’s so nice to make and build those connections over time and the hope is that these people will grow into community leaders as well. The startup community is an inherently transient place because companies are constantly exiting or they are growing or they are moving to other locations, so as a community we are always in need of strong leadership. The earlier you can get people plugged in and involved with the community and to really invest in the community, the better off the community is long-term.

Chinn: It sounds like you do a lot of mentoring, which is very generous of you. Why do you choose to spend time mentoring and why is it so important to you?

Vittorio: I like mentoring because I have been very fortunate in my life with both of my parents being successful business owners. When I was in the process of growing my current business or another business that I’ve had over the years, I have always been very blessed to be able to run to them when I have problems. It’s good to have someone even with just the emotional struggles—for example, when I first opened the firm and wasn’t making any money, I was wanting to quit literally once a week. I still joke like that now, but those feelings have significantly decreased. It’s been nice to have my mom there to say, “that’s just part of being a business owner.” I don’t think any business owner hits a point of success where they don’t panic occasionally and think it would just be easier to go take a job and work for someone else. For me, mentoring is a way to pass forward into the community the opportunity and insight that I had freely provided to me.

Chinn: That’s a great reason to pay it forward with mentoring. It sounds like your parents were amazing mentors, but are there any other mentors in your life you can talk about?

Vittorio: My first real professional mentor is an attorney that’s now a judge in Collin County. He was my mentor in independent study in high school, and then he swore me into the bar a decade later after I finished college and law school. I don’t know if he knows he was a mentor, but he’s always been a good touchpoint for what being a legal professional means and helps me navigate the practicalities of being a transactional attorney. This is going to sound ridiculous but there are a lot of scams that target attorneys and they can get really sophisticated! I got hit with one when I was in my first six months of practice. I had flown overnight to get to Dallas because I thought I had this opportunity for a major business transaction. Then one of my friends from law school said it sounded fishy and that I needed to talk to someone. I went to my mentor’s office and I remember saying, “I’m pretty sure it’s okay but I just want to get your feedback on what you think about this opportunity that I’ve been presented.” I literally got five seconds into it and he said it was a scam and that it wasn’t real. It’s so obvious now, but I’m not joking when I say I could have easily lost hundreds of thousands of dollars.

There have been a lot of great mentors throughout the legal profession and in the startup community. One of the great things about Dallas is that a lot of our leaders are really approachable, and if you show up and you express a genuine interest in helping, the community really is a welcoming place. I had a lot of great leaders that helped provide me with connections and guidance about how the community works, and the structure and flow of things. Without them, I certainly wouldn’t be where I am now.

Chinn: I agree. I know you bring a legal lens to things, but you have also started your own business and you have a lot of entrepreneurial business experience. What is your recommendation for entrepreneurs that are in this crisis?

Vittorio: I have been telling pretty much every entrepreneur that I’ve talked to recently that just surviving is an accomplishment at this point. As entrepreneurs, we get so focused on the hustle and high growth mindset that we put a lot of pressure on ourselves to hit numbers, goals or certain growth points. If you can make it happen, that’s great, but it’s also okay in this situation to be able to have a peace of mind that you are still existing. You’re beating the curve just by still being around and you have to give yourself some credit for that. You’re going to burn out emotionally, mentally and physically if you are constantly trying to maintain a growth strategy like nothing is going on. Two or three months from now, you’re not going to be any good to anyone if you hit a wall. Being patient is one of the most important things. Entrepreneurs are not patient people, generally speaking.

Chinn: That’s right. Surviving is success in some climates, right?

Vittorio: Yes, and it’s a unique opportunity. Sometimes the startup community gets so focused on these big events, but entrepreneurs aren’t really making any genuine connections. You can go and hand out fifty business cards, but what is that getting you? Probably no tangible long-term value. In the long-term, having to slow down and take a more one-on-one approach to networking will contribute to more fruitful connections than we see at some of these speed networking type events that are becoming the norm.

Chinn: Got it. Hypothetically speaking, if I am a brand new mentee, how can I prepare for my first conversation with my new mentor?

Vittorio: The first question I always ask my mentees is, “What do you need from me and what do you want to get out of this relationship?” If I get on the phone with a mentee and I ask them that question and they don’t have an answer, I won’t know how to help them because I could go in a million different directions. You have to be able to communicate what value you are seeking.

Additionally, being honest with your mentor is a really important thing. My job as a mentor is not to tell you what to do with your company, or in your position. I am there to share my experience with you and to serve as a sounding board for the things that you are going through, but at the end of the day, you are the one in control. If I’m consistently giving you a perspective you think is useless and not helpful to you, then be honest and have that conversation. As a mentor, it’s frustrating when I have conversations with a mentee and, the next week or so later, we are having the exact same conversation because they are not implementing anything that we talked about. If you can articulate reasons why you decided to go a different course, that’s completely your decision. But, if we keep having the same conversations over and over, that gets really frustrating. The mentor can change direction in the perspective that they are giving by delivering it in a different way, or you may just need a different mentor because that match is not always going to be good for every single person.

Chinn: That’s great advice. Why is one-on-one mentoring impactful, and why not just write an article or teach a class?

Vittorio: I do those things and they’re fun, but you never get to see the byproduct of that. As a professor, if I stand on a stage and talk to 50 people, statistically 75% of them are not listening to me even if they have chosen to be there voluntarily. I will never know whether I actually gave them the information they needed, or whether that was impactful for them in any way. Having a one-on-one connection helps me to see the fruits of that advice. There are people that I have mentored in the community that are now leaders in the community, and it’s nice to have that relationship evolve over time. It leads to a more cohesive community and it gives us a better working relationship in the long-term if we have grown together in that process. One-on-one mentoring gives you a unique opportunity to establish those long-term relationships that you don’t get from a one-off encounter like a speaking engagement.

Chinn: What reading material do you recommend for budding business people or entrepreneurs?

Vittorio: The first book I always recommend—specifically for technology-based founders—is Venture Deals by Brad Feld and Jason Mendelson. Kauffman Fellows runs a Venture Deals class that I’m fairly confident is still free and it’s taught by Brad and Jason. You meet online and they give you work to do through the book. You pair up with groups and do a simulated negotiation and fundraising round. It’s really helpful for founders that don’t have any prior experience in startups or fundraising, to at least grow a working vocabulary for negotiations in those types of conversations.

Chinn: That’s good to know! What is something you are watching on TV right now?

Vittorio: I’m truly a nerd at my very core, so I’m rewatching West Wing. I also like to watch Chef’s Table. To me, it’s really interesting to look at how people are in the height of their profession—and other professions completely unrelated to what we do—and see the methodology that they have adapted to be successful. We will try to apply that same kind of underlying philosophy to the work that we do even though they are unrelated. That’s my liberal arts background hard at work.

Chinn: Wow, you take a cooking show and turn it into work. Are you supporting any local restaurants or doing takeout?

Vittorio: There’s a restaurant that’s not too far from where I live called Latin Deli that’s super good. I was just at Encanto Pops in Oak Cliff, which I really love. They have Aguas Frescas that you can mix on your own. I’ve also been going to Meso Maya because there’s one in Lakewood. Lastly, White Rock Coffee—an excessive amount of it!

Chinn: Of course, it has to be an excessive amount! Thank you so much, Jessica. We’ll see you in the real world pretty soon.


The DEC Network is a partner of Dallas Innovates. The 501c3 non-profit organization drives innovation and economic impact by helping entrepreneurs start, build, and grow their businesses. Through a number of innovation hubs across DFW, The DEC Network provides entrepreneurs with education, mentorship, community, and advocacy. For more information, please visit www.thedec.co.

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