Friday, Sept. 15, the College of William and Mary Cohen Career Center hosted Matthew Heist ’91, former Vice President of Finance and Business Operations for Slack, on Zoom for the first session of a monthly guest speaker series through the Alan B. Miller Entrepreneurship Hub.
Student partner at the Entrepreneurship Hub Sara Curtiss ’24 introduced Heist.
“I’m excited to introduce Matt Heist to our entrepreneurship community today,” Curtiss said. “Matt is a finance professional with over 25 years of experience leading finance business operations teams in a variety of roles in the consumer, internet and software industries.”
During his time at the College, Heist majored in government and minored in economics. He was also a member of the College’s swim and dive team. His initial interests prompted him to attend law school after completing his undergraduate education.
“I thought I’d be a lawyer,” Heist said. “I thought I would be at some law firm doing law. During college, when you have that, it makes you somewhat complacent. I wish I had actually done that a little differently. Like I said earlier, I wish I had gotten out there a little bit and looked around on the career side of things.”
Heist attended The George Washington University Law School and eventually served as an associate attorney at Cacace, Tusch and Santagata in Stamford, Ct., focusing on commercial litigation. Despite achieving his initial goal of becoming an attorney, Heist decided to pursue finance and entrepreneurship instead.
“I mean, some of it was just, quite frankly, anxiety,” Heist said. “I was sitting there as a lawyer, and I was like, ‘This is just not what I want to do.’ And there wasn’t some 20-year path ahead of me. It just was, I gotta get the hell out of the law, not because the law itself is bad or my firm was bad. It’s just for me, I wanted to try something different.”
To pursue his interests in finance and entrepreneurship, Heist received his Master of Business Administration from the University of Southern California’s Marshall School of Business, later beginning his new career at Yahoo as a Business Development Director in 2000. After his work at Yahoo from 2000 to 2007, Heist worked as the president and CEO of automotive publisher High Gear Media.
“The person who founded [High Gear Media], as often happens, was great at raising money,” Heist said. “He was great at putting out a vision, but he just did not love operating. And so very soon after the company was founded, I came in to run it.”
After joining the team at High Gear Media, Heist recalls a series of difficulties related to the financial crisis from 2008 to 2009 and the evolution of the cell phone.
“For six years, we had so many headwinds,” Heist said. “The company was founded right about the time when Lehman happened, which was this financial crisis in ’08, ’09, which was just brutal and made it really hard to sell advertising, particularly as a small player on Google. It was also the time where, quite frankly, the phone really took off, versus the desktop, and that had a profound influence on advertising on the Internet.”
Despite the difficulties associated with his position at High Gear Media, Heist reflects fondly on the skills gained from his time with the company.
“I would say, whereas Slack wasn’t easy, but it was a really successful thing, this one was successful, but my gosh, the grind was pretty brutal,” Heist said. “I would say it was definitely the most worthwhile thing I did as far as improving as a manager and, you know, quite frankly, as just a professional.”
“I will tell you, with a pivot on product strategy, with the reorganization of a team and perhaps sometimes even parted ways with a team member where the fit just wasn’t right. I never once said, ‘Gosh, I wish I had waited to do that longer,’” Heist said. “You always look back and kind of say, ‘Gosh, I kind of knew we needed to do that, and I wish I had done it a little sooner.”
As he took note of his diverse experiences in business and entrepreneurship, Heist acknowledged the pillars of the Entrepreneurship Hub, highlighting reflections of previous decisions from throughout his career.
“I will tell you, with a pivot on product strategy, with the reorganization of a team and perhaps sometimes even parted ways with a team member where the fit just wasn’t right. I never once said, ‘Gosh, I wish I had waited to do that longer,’” Heist said. “You always look back and kind of say, ‘Gosh, I kind of knew we needed to do that, and I wish I had done it a little sooner.”
Director of the Hub Brandon Hennessey commented on the importance of the Alumni Guest Speaker series.
“Ultimately, the stories of the Alumni Guest Speaker Series encompass venture launches, failures, successes and trials along the journey in a way that is accessible to the audience,” Hennessey wrote in an email to the Flat Hat. “We encourage questions and engage with our speakers to discern commonalities and insights for progressing their own entrepreneurial thinking path.”
Just as the Entrepreneurship Hub encourages growth in students’ career skills and entrepreneurial thinking, Heist reminded students interested in entrepreneurship of the importance of focusing not only on a major but also on developing skills applicable in later life.
“My only advice would be to stay true to the liberal arts if that’s what you’re majoring in, or STEM if that’s what you’re majoring in,” Heist said. “But, do go a little bit beyond that to get a hard skill of some sort, such as finance, so you understand a little bit about the economy or know how to use Excel and lightly know how to code. And again, some of that’s not because that’s what you’re going to do for the rest of your life. But that first job is such a bear to get sometimes, and those hard skills can actually help you get it and really set you on the path for your entrepreneurial journey.”
The guest speaker series continues with speakers attending every other Friday at the Hub at 2 p.m.
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