Summary
Key Insights
1. Lawyers Must Be Built, Not Just Taught.
Law school "re-wired the brain" but did not prepare Matt to be a lawyer. True legal ability comes from a demanding apprenticeship—starting with intensive trial experience (trying 100 cases in two years as a prosecutor) and 11 years of continuous learning ("stealing" skills) from exceptional lawyers at a firm. This rigorous practice cultivates the necessary analytical and problem-solving muscles.
2. The GC's Primary Job is to Facilitate, Not Obstruct.
To be a true business partner, the legal team must operate from a mindset of "start from yes and then work backwards". This means meeting the business partner conceptually at "yes" and then providing a roadmap (e.g., "let's do A, D, G, Y, instead of A, B, C, D") that sidesteps legal landmines while achieving the same business outcome. The three fundamental choices in every situation are: make it better, walk through it neutrally, or leave it worse; the goal should always be to add value.
3. Leadership is Empowerment and Accountability.
Successfully transitioning from a peer (DGC) to the GC requires leading through empowerment and agency. The mantra must be: "If there's credit, it's yours. If there's blame, it's mine". This confidence allows the team to "reach for something as a business person" and accelerates growth, knowing the GC will stand in front of the consequences.
4. Decisiveness is the Competitive Edge for In-House Counsel.
Unlike law firm lawyers motivated by billable hours, in-house counsel's value is tied to efficiency. The ability to make "snap decisions" with sufficient attention, reflecting fluid and immediate needs, is critical. This decisiveness is rooted in "gut" instinct—the central processing of every lesson and experience learned.
5. Hiring for Practicality and Owners' Mindset.
When hiring, one of the gating questions is: "Why do you want to be an in-house lawyer?". Ideal candidates demonstrate a desire to know the business inside and out (an owner's mindset) and possess practical, real-world experience, rather than just Ivy League credentials
6. Closing Insight
The promotion from DGC to GC is not a leap of faith; it is the natural consequence of consciously positioning yourself as the indispensable operational executive who has already been doing the job and leading the team effectively.
In this podcast, we cover
0:00 Introduction
1:45 Tyler asks about his career as an Illinois prosecutor
4:55 Tyler asks what inspired Matt to be a prosecutor
17:57 Tyler asks about transitioning in-house roles in tech
26:14 Tyler asks about managing work relationships after you become general counsel
32:15 Tyler asks about instilling a business mindset in a legal team
40:06 Tyler on hiring lawyers with an owner’s mindset
46:39 Tyler asks fun questions
52:27 Book recommendations
55:23 What Matt wish he knew as a young lawyer
































.avif)







.avif)








