Twenty-seven Things
That I wish I'd known when I started my MBA
Orientation for the Class of 2027 is underway at Chicago Booth. I remember both helping to run portions of it in 2026, and participating in it in 2025.
This week I am sharing a listicle of twenty-seven things I wish I’d internalized during orientation, before starting my full-time MBA.
Recruiting for VC is a two-year search for a full-time role. Keep your eye on the prize, and spend all your pre-professional time improving your qualifications as a candidate for those full-time roles.
VC recruiting requires spending time networking with VCs (who may hire you) and with founders (to help them, and to show deal flow to VCs).
The recruiting process for a VC fund models the work one does there. Similarly to consulting, somebody who doesn’t like recruiting for VC probably won’t like being a VC very much.
The job opportunity with the best odds of success is the one that never makes it to a public posting because somebody built a relationship with the hiring manager.
Getting access to deals is all about building relationships with founders.
Truly proprietary deal flow is incredibly rare.
Who you know and what you know both matter.
Good investment math won’t ensure a fund does a deal, but bad investment math will kill a deal incredibly quickly.
Investor-market fit is at least as real as founder-market fit.
A fund’s initial investment size defines the stage at which it invests, which is basically (to a first order approximation) the same thing as its strategy.
The success of any given financial transaction for a company is ultimately validated by the terms of the following financing. Ex: a particular Series A is only really assessable after the fact when looking at the terms of the Series B.
VC is unique among investing roles because investors can be wrong about most of the deals they do, and the ones where they’re right about will define their career. Therefore, it is critical to an investor’s professional development to track why investment decisions get made, as well as what the outcomes of those decisions are.
VC is unusual in that it’s possible to do the work before getting a job in the field. This drove a lot of the decisions I’ve made here on Substack.
I’ve heard that people who want to work at a startup should learn to think about potential employers like an investor. This applies to VCs too — learn to think like a Limited Partner.
An employee’s job is always to make a boss look good to their stakeholders.
There are only three jobs.
Job description archetypes
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I’m on my way back from Cambridge, MA, where I watched one of my brothers defend his PhD thesis. It was a truly awesome experience.
Each stage of the career exploration and job search processes has as its goal qualifying a candidate for the next stage. This means that at each stage, the candidate (or the firm) should opt out if it’s not a great fit.
In-semester internships can supercharge career exploration and make applicants more competitive — if the intern meets or exceeds expectations.
Write. It helps build a brand and clarify thoughts on topics.
Whatever you plan to build…do it in public.
Hold yourself to the same standards as founders.
Seek opportunities to win together with other investors and with founders.
Many great founders seem to want to be left alone.
Be open to serendipitous opportunities.
Only play games you think you can win.
Picking games carefully
·Back when I was in high school, I swam and played water polo. To say I was bad at both sports, relative to the other players on my high school teams, might actually be an understatement.
Study. Especially if you’re a career changer.
Some courses are more important than others. At Booth, classes that I thought were particularly relevant and worthwhile included:
Accounting for Entrepreneurship
Entrepreneurial Finance and Private Equity
Institutional Private Capital Investing
PE/VC Lab
