We were lucky to catch up with Masayoshi Haynie, Esq. recently and have shared our conversation below.

Alright, Masayoshi thanks for taking the time to share your stories and insights with us today. Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?

They say there’s no reward without risk, and for me, I couldn’t agree more.

My risk I took starts with me betting on myself, by pursuing my degree in law. Now that may not seem like a risk, as many lawyers and attorneys benefit greatly from the decision to go to law school, but for me, without any attorneys in my family or a blueprint to follow, it was probably the biggest risk I took to date.

I graduated with my undergraduate degree without debt, excelling through my studies all throughout my life. But as I entertained the idea of law school, with little to no guidance, it made the weight and gravity of the things I didn’t know, that much greater. Questions like when should I apply, or when I should take my LSAT (law school admissions test), or what school should I go to, left me at what felt like a huge disadvantage to my counterparts who may come from lineages of attorneys.

Unorganized and ignorant to the pre-law process, I applied to law school on the day of the deadline after self-studying for the LSAT and receiving a score many told me wasn’t good enough to reach the heights I had planned for, which at that time was just to go after the best opportunity law could afford me. But with faith and perseverance, I was admitted to one school, a law school outside of the Top-100, on a partial scholarship, after being waitlisted and denied by most. I had the opportunity, and it was all I needed.

However, the risks don’t stop there as I excelled my first year, landing amongst the top 20 students, which led many of the people around me to advise me to transfer to a “better school.” Legal societal standards say that certain job offers like working at a big firm, would be impossible without a better school on my transcript, despite how stellar my grades were. But one thing that always stuck with me was, it’s only impossible until it’s done. So I decided to stay at my law school, where I had already developed myriad relationships, a great brand and worked my way to a full-ride scholarship. In an effort to avoid a mountain of debt, I bet on myself, and after building and cultivating the right relationships, I found myself with an offer at a Top-10 Chicago big law firm, which I came to learn that I was the first from my law school to achieve at that specific firm.

I want to share this because, so many of us count ourselves out of taking risks because of the limitations other place on our vision and calling. But thankfully, our calling in life isn’t a conference call… it’s yours for a reason.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

So I decided I wanted to go to law school after experiencing racial tension that happened during the senior year of my undergraduate collegiate tenure, the University of Missouri (circa 2015). It was during that time, as a journalist, that I was tasked to tell the stories of those going around me, but very little did I ever have the chance to impact that story proactively.

As the story received national attention, I started to meet attorneys and slowly learned how valuable a law degree could be. Fast forward and now I have a chance to take my skillset as an attorney and provide those around me, especially my community, with access to resources and knowledge that I’ve gained throughout law school and through my career as a corporate attorney, working on billion-dollar transactions.

Focusing on the access and resources necessary for anyone to thrive in their respective fields, I decided to also launch a non-profit mentorship service called the Law School Mentor, which serves as a gateway for first-generation black and brown students to receive free mentorship, resources and overall access to the diversity of what success can look like for them, by providing them with different examples of what practicing law looks like, all for free. The organization hosts virtual coffee chats over social media, exposing pre-law and current students to different practicing attorneys and law students from around the country, who have all agreed to share their story, answer questions and continue the conversation off-screen by providing a means to contact them post-talk. Due to its success and support, I’ve now replicated and expanded the organization to the medical side and launched the Med School Mentor to mirror the same access within the field of medicine.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

Although I’m only three years post-graduation, I realize how important branding is and building relationships. However, both don’t happen without confidence. Confidence of course is built from experience and experiencing a certain-level of success, but to be honest, confidence is something that takes time to perfect. I’ve been able to build the trust and reputation as a young, fearless advocate that many have suggested for opportunities only offered to those 10 years my senior, because of how I show up for myself and others. I realize there’s room for everyone at the proverbial table, and that collaboration beats competition any day. But you can’t build a billion-dollar brand overnight, so I realize the importance of small, consistent steps and commit to the idea that the day you plant the seed, won’t be the day you eat the fruit. A journey of 1,000 miles begins with a single step.

Conversations about M&A are often focused on multibillion dollar transactions – but M&A can be an important part of a small or medium business owner’s journey. We’d love to hear about your experience with selling businesses.

Well this is my career, so I’m happy to help anyone thinking about the world of M&A (mergers and acquisitions). Some things you’ll want to keep in mind about selling a business include: (i) identify your why, your mission and background materials, the story you have and brand identity; (ii) take your TIME, find professionals who can help you evaluate your business and how you come to that evaluation; (iii) decide how you want to negotiate the deal and market it, whether with a broker or related party; (iv) hire me! lol or a lawyer, it’s way easier to hire us proactively, although expensive, than hiring us reactively when something went wrong; (v) come up with what you want to do with the proceeds!

Contact Info:

• Website: https://www.faegredrinker.com/en/professionals/h/haynie-yoshi#tab-Overview; thelawschoolmentor.com
• Instagram: thechicagoattorney ; thelawschoolmentor ; themedschoolmentor
• Linkedin: https://www.linkedin.com/in/masayoshi-%E2%80%9Cyoshi%E2%80%9D-haynie-esq-88401990

Image Credits
Javon Smith, Tony McDaniels, Ishmael Rashaun