027 - Brian DeChesare
Brian DeChesare is the founder of Breaking Into Wall Street and Mergers and Inquisitions.
Mergers & Inquisitions is a website dedicated to careers in the finance industry, with over 600 expertly crafted articles, over 500,000 monthly visitors, and over 100,000 email subscribers. The site features interviews with industry insiders in investment banking, private equity, venture capital, hedge funds, sales & trading, and other fields, as well as career tips, news commentary, case studies, and modeling tutorials.
Breaking Into Wall Street is M&I’s sister site. It offers online training products like PDF guides and video courses as well as coaching services designed to help people break into investment banking, private equity, and hedge funds. Early in my career, I was both an avid reader and a customer of Brian’s.
Although Brian has been a successful entrepreneur—earning a case study mention in the 4-Hour Workweek, as an example—I’m more impressed by Brian’s ability to “step off the line,” as Jocko Willink would say, to strategically re-orient himself.
During our conversation, we discuss two points where Brian strategically pivots in order to achieve his true long-term objectives. We also cover Brian’s experience with angel investing, his biggest business inflection points, and how he structures his life to accentuate his strong suits.
Links from the Show
Mergers and Inquisitions www.mergersandinquisitions.com
Breaking Into Wall Street www.breakingintowallstreet.com
Brian’s Reading List www.strategychainpodcast.com/support
Time Stamps
0:03:40 – Brian’s “slap in the face” moment
0:07:35 – Connection to Episode 003 with Michael Pollack
0:09:41 – Catch-up since Brian’s latest life story post
0:12:19 – Eliminating policy-borne headaches (refunds, support, payment plans)
0:22:31 – The difficulty of transitioning from a one-man show to a team
0:28:02 – Misinterpretations of the 4-Hour Workweek
0:31:52 – How to leverage obsessive-compulsive traits (spurts, Toggl time tracking, and adapting over time)
0:44:26 – High-yield activities and attribution difficulties (Wicked Reports)
0:50:31 – Issues with partnerships within a niche industry
0:55:46 – Business inflection points (pitching content, product development, marketing)
1:11:30 – The psychological lift from making the first sale
1:17:13 – Developing products by offering services
1:22:03 – The magic decision that improved profitability AND unit sales: pricing
1:30:32 – Brian’s angel investing experience
1:48:19 – What Brian would say to a younger version of himself: think of other options
1:50:40 – Brian’s future plans
1:55:15 – Book recommendations (Dan Kennedy’s work, Jason Fried & David Heinemeier Hansson: Work Doesn’t Have to Be Crazy, Rework, Remote, Henry IV Parts 1&2, Henry V, A Song of Ice and Fire, The Witcher Series, Brandon Sanderson’s The Wheel of Time, Robert Jackson Bennett [City of Miracles, City of Blades, City of Stairs])
2:06:08 – Closing thoughts: you can only connect the dots in retrospect, find the unconsidered options.
Strategy Chain Links
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