The Insider's Compass

Stop Guessing. Start Executing. The Investment Banker's Playbook They Don't Teach in School.

From crafting the perfect "Coffee Chat" email to surviving the Analyst gauntlet - get the definitive insider's compass to breaking in, moving up, and exiting to Private Equity, Hedge Funds or Corporate.

Crack the Street: Your Ultimate Guide to an Investment Banking Career by Brett Robinson

The Three Pillars

Your roadmap from breaking in to moving up

Hack the Recruitment Funnel

Forget generic advice. Get the exact "Cold Email" templates that get replies from MDs, master the "Airport Test" for Superdays, and learn the specific "Core School" vs. "Non-Target" strategies you need to get the interview.

Survive the "Analyst Gauntlet"

A raw look at the 100-hour work week. Learn to master financial models, databases, slide creation, deal organization (the analyst's lifeline), navigate office politics from intern to MDs, and why turning comments accurately is your fastest path to promotion.

The Buyside Roadmap

Don't get caught flat-footed. We decode the hyper-accelerated "On-Cycle" PE recruiting timeline, the difference between Mega-Funds and Middle Market, and how to position yourself for coveted exit opportunities.

What You Will Learn

The "Email Sanity Check": 9 rules to prevent career-ending "Reply All" mistakes.

The "Mouse-Free" Challenge: Why mastering Excel shortcuts isn't just about speed – it's about sleep.

The "Data Dive" Protocol: How to unearth critical info when Google fails you.

MD Archetypes: How to spot the difference between a "Rising Star" and a "Dinosaur" – and why your bonus depends on it.

The "Downstream" Strategy: How to break in via regional boutiques if you missed the Bulge Bracket wave.

Brett Robinson - Managing Director in Investment Banking

About the Author

Brett Robinson

Brett Robinson is a Managing Director in investment banking with a career spanning bulge-bracket banks, elite boutiques, and private equity. From the deal rooms of Guggenheim Securities to the Boardrooms of Fortune 500 companies, Brett has seen the industry from every angle. He wrote 'Crack the Street' to share the hard-won wisdom he wishes he had when starting out.

  • Former MD at Guggenheim Securities
  • Ex-CPPIB Direct Private Equity
  • Advisor on multi-billion dollar mergers
Get the Book

Mentorship

Connect directly with Brett Robinson who's dedicated to giving back to aspiring bankers. Get personalized guidance, insider perspectives, and strategic advice to navigate your path into investment banking.

Insider Advice

Weekly insights on deal dynamics, interview prep, and career navigation.

Career Strategy

How to Transition from Processor to Thinker

The surest way to be viewed as an all-star is to consistently perform the duties of the role one level above you. Learn how AI has shortened the curve from data processor to strategic thinker in 2026.

Read More
Career Strategy

The Investment Banking Lateral Playbook: Moving from Mid-Market to Bulge Bracket

A lateral move isn't just a job change; it's a career accelerant. Master the playbook for navigating the off-cycle market and securing a seat at a premier platform.

Read More
High School Prep

The "Target School" Arbitrage: Why Your 2026 College Choice is the Real Start of Your IB Recruiting Cycle

Over 100,000 students compete for roughly 1,000 summer internship spots each year. That's an acceptance rate below 1%. Here's how your college choice gives you an unfair advantage.

Read More
High School Prep

What Actually Is Investment Banking? (Forget The Movies): A High Schooler's Guide

Forget the movies. Here is an expert's breakdown of what investment banking actually is, written specifically for ambitious high school students planning their future careers.

Read More
Networking Mastery

The MD's Guide to Investment Banking Coffee Chats: 5 Questions and 3 Templates That Actually Work

Master the coffee chat with the exact email templates, questions, and follow-up strategies that MDs actually respond to. Move from "Online Applicant #4,000" to "Internal Referral."

Read More
High School Prep

The High School Playbook: How to Build a Wall Street Resume Before You Turn 18

Investment banking recruiting starts earlier than you think. Here's exactly what you should be doing in high school to put yourself in the top 1% of candidates before you even step on campus.

Read More
Career Strategy

The Ultimate Investment Banking Internship Success Checklist: How to Convert Your Offer

Master your summer analyst internship with this comprehensive checklist covering professionalism, workflow execution, communication etiquette, and the all-star mindset to convert your offer.

Read More
TECHNICAL SKILLS

The Alchemy of Finance: Mastering Pro Forma Capitalization with the "Chocolate Company"

Master pro forma capitalization with the Premium Chocolate Company case study. Learn how to calculate Enterprise Value, analyze special dividends, and understand EBITDA multiples like a Managing Director.

Read More
INDUSTRY LANDSCAPE

Bulge Bracket vs. Elite Boutique vs. Middle Market: Which One Should You Actually Choose?

Stop chasing prestige rankings. Learn which banking tier actually fits your personality and career goals—from Goldman Sachs to Evercore to William Blair.

Read More
HIGH SCHOOL PREP

The "Core School" Reality: Why Your College Choice Is Your First Investment Decision

Choosing a college is your first major career investment. Here's the Top 20 Core Schools cheat sheet and why your college choice determines your recruiting path.

Read More
INSIDER TRUTHS

The Door Closes: What We Actually Talk About When You Leave the Room

You walk out. The latch clicks. For you, the interview is over. For us, it has just begun. Here's what MDs actually discuss in the 3-5 minute debrief that decides your fate.

Read More
RECRUITMENT STRATEGY

The "Core School" Reality: Why Your Online Application is Being Ignored

Over 100,000 students apply for 1,000 spots each year. If you're not at a target school, the online portal is a black hole. Here's the guerilla playbook for non-target students.

Read More
INTERVIEW PREP

The Technical Interview Trap: Why Memorizing "The 400 Questions" Won't Save You

Most candidates panic and memorize 400 definitions. Then they freeze when asked a nuanced question. Bankers want thinkers, not robots. Here's how to pivot from memorization to mastery.

Read More
CAREER STRATEGY

The "On-Cycle" Frenzy: Why You Need to Prepare for Your Next Job Before You Start Your First One

Two months into your banking job, headhunters call about a role starting in two years. Welcome to PE recruiting—where the game starts terrifyingly early.

Read More
RECRUITMENT HACKS

The "Black Hole" of Online Applications: Why Networking is Your Only Real Strategy

Banks receive tens of thousands of resumes for ~1,000 spots. If you want to break in, you need a champion on the inside. Here's the exact playbook.

Read More
DEALS

Anatomy of a Deal: The 7 Phases of M&A (And Where You Fit In)

Deals are sprawling, messy marathons lasting 4-6 months. Learn the unvarnished roadmap from Kick-Off to Closing Dinner and where you fit in each phase.

Read More
ANALYST SURVIVAL

The First 90 Days: How to Survive the Analyst Gauntlet

Your first three months will define your reputation. Learn the unspoken rules, the "fire drill" rhythm, and how to avoid career-ending mistakes.

Read More
INTERVIEW PREP

How to Answer "Walk Me Through Your Resume" in Banking Interviews

The most common opening question has a hidden structure. Here's how MDs actually evaluate your answer and what separates top candidates from the rest.

Read More

Ready to Crack the Street?

Join hundreds of aspiring bankers who've used this book to land offers at Goldman, JP Morgan, and elite boutiques.

Buy on Amazon