Middlebury alumnus Craig Thompson ’13.5 wants students and young professionals to have access to free, high quality technical training resources to help them enter the finance industry.
That’s why he started his podcast “Breaking into Finance” last June, which features two Middlebury students with no previous financial knowledge.
The podcast has released 40 episodes so far, covering authentic finance technical coaching sessions with Olivia O'Reilly ’25 and Blaise Seifer ’23.5, as well as mock interviews with students from other schools and majors preparing for and seeking jobs in the finance industry.
In addition to running the podcast, Thompson is the Founder & CEO of Prophet Models, a venture-backed financial modeling software company, and runs a fractional CFO business. He previously worked in investment banking at Goldman Sachs and in private equity at KKR.
After conducting over a hundred coaching sessions with undergraduate students seeking to work in investment banking, Thompson found that the number of coaching calls candidates receive is the strongest predictor of their success in attaining a job. Interview performance greatly depends on the candidate’s ability to master financial technicals and industry jargon, according to Thompson, skills honed through practice with professionals familiar with the field.
Breaking Into Finance is the most recent project Thompson has developed in finance education; he also created the Wharton Partners in Equity Case Competition as an MBA student and helped design Wall Street Oasis’ Private Equity Deals Process online training course.
“If you think the SAT and standardized tests are biased towards students from affluent backgrounds, just wait until you see the job market,” Thompson wrote in an email to The Campus. “Nobody – nobody – gets a job in finance without some kind of help. Whether it’s alumni, faculty, or parents/family, you need to learn the language from somebody.”
“I want to democratize the access to this level of coaching, so that the people who really are the best and brightest, irrespective of their background and their network, can stand out and get the job,” he wrote.
Using two Middlebury students with no prior financial knowledge as podcast co-hosts is a key part of this mission.
Siefer, a sociology major interested in the finance industry, believes that he and O’Reilly’s initial lack of financial knowledge mirrors the potential audience of the podcast and better resonate with them. Listeners can learn alongside the co-hosts, starting from scratch and gradually acquiring technical knowledge as the episodes progress.
O'Reilly, a psychology major, has found that her involvement as a co-host of the podcast has significantly helped her in understanding and applying the technical concepts that she was previously unfamiliar with and preparing her for future job interviews.
“Even though some concepts were difficult to grasp at first, it was so satisfying, kind of like a top of the mountain moment, when I was able to correctly and confidently grasp the concept and answer the questions that Craig was asking,” she wrote in an email to The Campus.
“Breaking Into Finance” will continue to be available on Apple Podcasts and Spotify.
“Right now I try to post new content twice a week, and I’ve experimented with new ideas like posting mock interviews with real students, but I really don’t know what the future holds in terms of content,” Thompson wrote. “But one thing I do know is that I will never charge a fee for subscriptions or anything like that. Creating a paid premium layer is directly counter to my mission, so I guarantee that Breaking Into Finance content will always be free to students.”
