102. David Willbrand, Smokestacks to Startups

Show Notes:

David Willbrand got married immediately after graduation in 1992. He talks about that period of uncertainty many graduates experience after school, and David did not have a clear professional direction, but with an interest in politics, he started working on a campaign for a city council candidate in Cincinnati, which was short-lived but did lead to a position with the Ohio EPA. David explains that he didn’t have a particular interest in working in government or environmental regulation but he needed a job and so took a job with the EPA, which involved climbing smokestacks, not something he had prepared for!

Testing Smokestacks for the EPA

David's job was to ensure that the testing would take place properly. He was onsite at regulated entities who had big smokestacks that needed to be tested periodically for particulate emissions and didn’t welcome the EPA oversight.  He would climb the 300ft smokestacks  in cold weather, sitting up there for eight hours to monitor the people actually doing the testing, aware of the potential impact the emissions were having on his health. Desperate for a new direction, David decided to pursue law  at the University of Cincinnati College of Law.  He shared how his unusual approach (desperation meets urgency) encouraged the admissions department into accepting his application.  He reflects that he hated the smokestack job is glad he did it, because it forced him to take a step in a new direction.

Life at Law School and into the .Com Era

David shares his love for law school, in particular the direct interaction he had with the faculty. He compares it to his experience at Harvard, where, with respect to the faculty, he felt like he fell through the cracks.

He went into law school without a clear understanding of what it meant to be a lawyer. He initially thought about environmental law but found it unsuitable due to the preference for engineers. He stumbled into corporate law and found the deal work and transactional work enjoyable. He was offered a job at a Cincinnati law firm in 1996, graduating in 1996. The date is relevant because 1996 is typically noted as the beginning of the .com era, and suddenly there were multiple  requests to deal with the legalities surrounding startups. Startup work became his area of focus.

From Cincinnati to a San Francisco Law Firm and Back Again

He was offered a job at a law firm in Boulder and spent three years there, advancing his career and skill set. However, life threw a curveball, and he and his family decided to return to Cincinnati in 2000. David worked remotely for a year with a .com company based in Ottawa and New York City. However, the .com bubble burst, and David decided to leave. At 32 with two kids and a wife, he joined another startup in Cincinnati, a B2B SaaS company. This was a difficult experience, as the company had to lay off many people and he had to take on more responsibilities in finance and HR.

Working with Founders and  Startups

In 2004, David decided to return to a law firm environment; he joined Thompson Hine, an AmLaw 200 law firm, in 2004. They wanted to create a startup and venture capital practice in the Midwest, and David was interested in being on the front edge of that pioneering activity. Working with startup companies and founders, he had the privilege of being a key advisor and gaining exposure to various industries such as biotech, hardware, devices, apps, and social media, and David shares how he liked being involved at the leading edge of innovation. He also felt that having a stake in the innovation economy was important for the future of the Midwest, and it was emotionally rewarding to participate in that mission.

From Private Practice to Chief Legal Officer at Pacaso

David shares that he got divorced in 2008 and remarried a year later to a woman he practiced with. He explains why they decided to live remotely for the first decade of their marriage. After the pandemic, David felt restless in his legal practice; he needed either a new direction or to change the configuration of his practice. He kept his eyes open for opportunities. He had worked with a client who had sold a company to Zillow and had started a new company called Pacaso. Pacaso was growing rapidly and needed a chief legal officer due to the complexity of the business and legal demands. In April 2021, David walked away from his practice, which he had built over 17 years, and has been at Pacaso since then. He explains that this experience highlights the importance of adapting to change and staying curious about new opportunities in one's career.

Making a Long Distance Marriage Work

David discusses the challenges of long distance marriages. He believes that the paradigm may be more workable for second marriages due to different expectations in duties. There are challenges, but a big benefit is that the couple really values their time together and doesn't take it for granted. They also get to spend time together without their children (when their children are with their other parents). This segmented approach can allow for a balanced relationship and lifestyle.

Counseling Clients and Monetizing Skills

David discusses his experience as an attorney and how he found himself as a business counselor to his clients as well. He talks about the difficulties many startup founders face and how he became a person they could talk to, and how he built strong relationships with his clients. He also shares that he has found that using his legal skills through side hustles can be a rewarding experience. David is currently an adjunct law professor at the University of Michigan Law School, and has taught courses on mergers and acquisitions, business associations, agency and partnership and, currently, startups and venture capital, for 20 years. He also works with various incubators and accelerators to help founders and startups.

Influential Harvard Professors and Courses

David's undergraduate experience at Harvard helped him develop critical thinking skills, which are essential for success in law school and other careers. He believes that his undergraduate experience at Harvard helped him unpack inherited beliefs and biases, making him a more dimensional human. He was actively involved at Phillips Brooks House, and the Food Salvage initiative, which provided food to homeless shelters around Cambridge. His experience exposed him to social issues and helped him develop a skill set for running an organization. He learned about people, deliverables, supply chains, and customers, which he believes were invaluable in running a business. David also shared his conservative, evangelical Christian background, which influenced his political, social, and cultural views from his youth through his time at Harvard and into his 30s. However, as he grew older, he struggled with this belief system, and eventually moved in a different direction and built his life on a different set of values and principles. 

 

Timestamps:

02:22: Career choices, job dissatisfaction, and law school admission

08:49: Inspecting smokestacks with a wand-like device

11:29: Career path and personal growth in law

17:12: Career changes, challenges, and lessons learned

20:29 Career journey in law firm environment, including startup work and personal life

27:02: Career growth and change, with a focus on a lawyer's transition from outside counsel to chief legal officer

29:33 The benefits of long-distance relationships for couples with children, with insights on how it can positively impact work-life balance and communication

36:35: Career development and pattern recognition in law

39:21: Personal growth, education, and entrepreneurship

45:29: Religious beliefs and their evolution in a Harvard student's life

Links:

David’s LinkedIn: https://www.linkedin.com/in/david-willbrand-9062011/

Featured Non-profit:

The featured non-profit of this episode is The Kentucky Student Voice Team, recommended by Rachel Burg Belin who reports:

“Hi, I'm Rachel Burg Belin, class of 1992. The featured nonprofit of this episode of the 92 report is the Kentucky Student Voice Team. The Kentucky Student Voice Team is an independent youth led intergenerationally sustained organization. The mission is to support young people as education research, policy and storytelling partners to co create more just democratic schools and communities. I love the work of this organization. So much so that ever since 2012 When I worked with a team of high school students to conceive and CO design it, I've been pouring my everything into it. I also serve as its managing partner. You can learn more about the Kentucky student voice [e-mail] And now here's Will Bachman with this week's episode.”

To learn more about their work visit: https://www.ksvt.org/