50 Cups of Coffee


In law school you meet an interesting collection of folks. Some of my classmates want to go into big law, some into public service and politics, others into finance or real estate. A select few are interested in entrepreneurship and tech, both from legal and business perspectives.  While exploring this landscape with some of my friends, I decided to take UVA Law's Entrepreneurial Law Clinic in the Spring of 2022 to learn more about what servicing entrepreneurial ventures as a lawyer really looks like. 

During one of our classes we were joined by a guest speaker, Tony Wilkins, who spoke about his career in finance and venture capital and the work he had done with lawyers. Intrigued by his talk on the intersection of law and business and taking him up on his offer to speak with any of us one-of-one, I reached out to him after class to schedule a meeting. After having a conversation about his personal professional journey and career advice, he recommended that one of the best ways to learn and grow as a young of professional would be to grab "50 cups of coffee" with different business and thought leaders I know, admire, or am inspired by in order to learn from their journeys and stories

As a challenge to myself, I am contacting mentors (old and new) and other business and thought leaders for 50 short 30-minute "coffee chats" (or zoom meetings / phone calls) in order to learn from their journeys and hopefully find some inspiration for my own and others. I thought I'd post it here on a semi-private blog mainly as a way to record these conversations for myself, and to share these conversations and advice with a small group of my friends and classmates. You might notice that numbers have been skipped. Some conversations were asked to be kept private, and are not included on the blog.

Tony Wilkins is a Private Investor, Founder, and CEO Coach who came and spoke to UVA Law's Entrepreneurial Law Clinic in the Spring of 2022 to discuss his entrepreneurial experiences. What stuck out to me during his presentation was 1) his candor, and 2) some striking similarities in the way we approach problems. He mentioned the need to control 7 distinct assets in order to build productive personal habits: spiritual health, mental health, physical health, time, reputation, connections, and financial. Contrast that with the 8 areas of focus listed in the mindfulness exercise I drafted and use:  spiritual health, mental health, physical health, intellectual, professional, social / relational, communal, and financial. After hearing this I knew I wanted to speak more with him.

In our phone call, Tony highlighted a few key points that serve as my main takeaways. 

1) List the one thing you want to be remembered for 40 years from now. This can be as vague or as detailed as you like (anything from "I want to be remembered as a good person," to "I want to be remembered as someone who deployed his assets to the best of his abilities in order to help good people do good things"). Use this to help you make decisions as a compass that will help you evaluate whether your decision is leading you towards or away from that guiding ideal.

2) There are no fatal errors you can make in your career before 30 other than going to jail, an insane asylum, or hell.  Almost everyone over the age of 30 knows that until they hit 30 they were searching and generally flailing around with a lack of direction or purpose. Most will say that up until the age of 30 they did not know what they wanted to do. Therefore, be comfortable with the fact that you are 24 and just got out of an academic setting where everything was laid out - syllabi, midterms, and tests. And that you are entering a space where nothing is laid out.

3) Take stock of what excites you. For the next year or so, write down everything that caught your attention - and everything that you don't ever want to do again. Note what turns you on, and what turns you off. Spend your time exploring things that excite you - people, experiences, philosophies, concepts, or businesses. Don't be concerned with feeling like a dilettante - relieve yourself of that judgement. Just kind of explore. And you might get a job offer that doesn't light your jets, but that's also ok. You will need money to survive and fuel your journey.

Tony raised more great points, but I thought I'd conclude with some insightful comments he made: you are working your way towards the version of the person you want to be. Be laser-focused on the things you are interested in and avoid peer pressure from people you don't intensely respect and admire. In the same way that someone who's trying to catch a train can't linger over conversation and drinks - that is your life. You are trying to catch that train.

And finally, he recommended the following books:

2. Matt Shandy

Matt Shandy is an Investor at Dundee Venture Capital and Adjunct Professor at OU Law. We met through one of the leaders of Cav Angels, the angel investing group affiliated with the University of Virginia. Matt is an alumni of UVA Law who transitioned into investing which stood out to me - oftentimes big law lawyers lateral into another firm or go in-house with one of their clients. During the spring semester, Rivanna Investments (the student-led investment fund at the law school) actually held an event with alumni to discuss how one handles the transition from law to finance - and how difficult it can be. 

During our call, Matt explained that he had always been a good student, and after graduating from the University of Oklahoma with a degree in PoliSci he took for granted that he'd go to law school. During his first year at UVA he realized that the law was probably not a forever career for him. After taking Mike Lincoln's class on emerging companies and venture capital (which Mike still teaches and is a fan-favorite) and working at White & Case for 2 years he moved to Cooley (Mike's firm). As he then eyed finance and prepared to make the switch to venture capital the lack of an MBA did create some challenges. Many people assumed a lawyer couldn’t work a spreadsheet. Today he’s a principal at Dundee VC, where he sources, diligences, and leads investments.

From our conversation I pulled the following lessons:

1) Pick a path and be intentional about it. Matt has friends who didn’t give much thought to their careers and they got stuck doing work they didn’t necessarily enjoy. And because they weren’t intentional about where they wanted to go, they didn’t have a compelling story to tell other employers when they wanted to make a switch. Sometimes you close doors by choosing certain pathways, but in order to build a compelling narrative for yourself it requires checking certain boxes and picking up experience and credentials that take time. For venture specifically, you typically break in earlier in your career or later after you exit a company. Trying to go in mid-career is tough, so you have to be purposeful about timing.

2) Fight peer pressure, but learn from work pressure. People are going to say, "Hey man, just do big law for two years. It'll be fine man, just for two years and then you can rotate out." There’s some truth to that, but rotating out can be tough. People often struggle to see lawyers as anything other than lawyers. So be prepared to work hard to achieve a career shift. Know what you want to do, and if that's not big law - then it's ok to start on a different path. If you're interested in building out products, do product management at a blue-chip firm. If you're interested in buying companies, start in consulting or finance. And if you're interested in law, then start at a big law firm. Getting good experience at an extremely high-achieving place can be incredibly difficult and high-pressure (see big law) - but that kind of work can build a level of drive and work product acceptability that will pay dividends in the future. Don't be afraid to work hard and push through professional challenges early in your career.

3) Enjoy the moment. Losing a close friend when you're young reminds you how valuable time is. It's not something that should be wasted, and even while you're moving forward and planning for the future, it's important to be present in the moment and enjoying your life as it happens to and around you. And don't forget to pay it forward! (Like Matt does with his work as a Professor at Oklahoma Law).

3. Dr. Abraham Kim

Dr. Abraham Kim is the Executive Director and one of the founding Board Members of the Council of Korean Americans (CKA). We first met over 3 years ago when I was a member of that years’ CKA Public Service Internship program, and after we found out that our houses were in the same neighborhood we spent a lot of time going on Walk & Talks around the local trails. Most of these were spent discussing the Korean American community and the lessons he had learned from his experience as the leader of an impactful organization like CKA. He also graciously passed on advice and guidance as I pursued my own initiatives. Luckily, I was able to snag some time with him to reconnect this summer for my 50 Cups of Coffee project.

Abe’s journey and perspective is an interesting one. He began working for his dad at a young age, joining him on his professional foreign relations trips around the world as his “photographer”. After studying IR in college he began working at CSIS as a National Security Analyst. While a lot of think tanks at the time had the practice of having juniors write 70% of a piece before a senior swooped in, made edits, and then published it without sharing the honorarium, Abe’s boss always co-authored the pieces and split the honorarium with those working under him. Because of that Abe was able to publish 25 articles by the time he left CSIS which helped him tremendously as he pursued a graduate degree. It was crucial that he had a mentor who pushed him forward, and tied his name to him. He then spent time completing his PhD at Columbia University before working at several other think tanks and then serving as VP and Interim President of the Korea Economic Institute of America before taking over as Executive Director at the Maureen and Mike Mansfield Center at the University of Montana. During his tenure, the Center became one of the foremost U.S.-Asia policy and leadership development institutes in the Pacific Northwest and Northern Rockies region. He then took over the reins at CKA, a national nonprofit organization whose mission is to advance the national voice and influence of the Korean American community. 

I asked Abe if he would share some specific thoughts and advice for young professionals. He responded: “It’s about the three C’s.” There are three elements to your growth that you should think about as you consider the impact you can have and how you can grow:

1) Content;

2) Communication; and

3) Community.

Content. Expertise and specialization. You ought to have world-class expertise in a niche where you can excel. Study and work to be the guru who people come to when they need someone who really knows what they are talking about. This is what makes you a substantive value-add.

Communication. That expertise can live in your brain, but if you’re not able to communicate effectively, talk, engage, and network, you are less effective and you might even be completely impotent. Developing your communication skills (in the broadest sense, not just public speaking) is how you take your work to the next level. This development means asking how do you inspire people, how do you engage people emotionally and intellectually, how do you truly know your audience?

Community. It’s all about relationships. The funny thing about life is that it’s so important to develop relationships knowing the value of those relationships at a young age because they can grow to haunt or help you 20 or 30 years later. Starting from a young age, develop a community around you – friendships, collegial relationships, and mentors. Knowing how to nurture those relationships, doing the follow-up, treating people humanely, being respectful, building bridges, that becomes cumulative.

When you have expertise, people respect you for your knowledge, you connect with people and you speak effectively, and you have a fan club built over time that can vouch for your humanity and that you’re a quality person- you’ve got the elements for professional success.

 The fourth c, “cash”, of course helps and can open doors as well. Not everyone has that luxury though, and if you can focus on those first three areas conceptually it will pay dividends in the future. There are other pieces of advice, like to not be afraid to take risks, but those are more tactical in nature. 

He concluded by sharing some recommendations for content, namely:

With the parting advice, "It is crucial to constantly be learning from other leaders. Don’t be afraid to be interdisciplinary and learn from experts from a variety of fields."

4. Judge Thomas Ambro