iConn Insurance Solutions

The Reading Room

Books our team keeps coming back to — on running a business, managing risk, leading people, handling money, and having harder conversations. Open to anyone. Pull up a chair.

Why We Keep a Reading Room

We talk to a lot of people about hard problems — business owners and their teams, families navigating change, folks thinking about going independent for the first time. The same patterns come up. And one we've noticed: the people who handle the hard stuff well tend to read. Not because reading is magic, but because the right book at the right moment gives you the language for what you're already feeling, and the playbook for what to do next.

This is our working list — a shared shelf we'd hand a friend over coffee. No affiliate links. No fluff. Just the books our team has actually read, argued about, and recommended to clients and friends who asked us "what should I be reading?"

Have a pick we missed? Tell us — we update this page as new titles earn their spot.

A curated business bookshelf with reading glasses and a coffee cup

The Shelves

Eight categories, dozens of titles. Each shelf scrolls left and right — drag, swipe, or use the arrow keys to browse. Every book here has earned a recommendation from someone on our team, usually with a story attached.

The Card Catalog

Find a Book

Search by title, author, or topic — or filter the shelves by tag.

56 books

Operations & Systems

How to build a business that runs without you in the room.

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The E-Myth Revisited by Michael E. Gerber

The E-Myth Revisited

Michael E. Gerber

The book that names the technician/manager/entrepreneur trap so many people are stuck in. If your business can't run a single day without you, start here.

The E-Myth Insurance Store by Michael E. Gerber

The E-Myth Insurance Store

Michael E. Gerber

Gerber's framework applied directly to running an independent agency. The systems-vs-self-employment distinction lands harder when it's about your book of business.

Traction by Gino Wickman

Traction

Gino Wickman

The EOS playbook. A practical operating system for small businesses — vision, people, data, issues, process, traction. Especially useful if you're between 10 and 250 employees.

Clockwork by Mike Michalowicz

Clockwork

Mike Michalowicz

The book that argues your business should be able to run a 4-week vacation without you — and gives you the playbook to engineer it. Painfully practical.

Work the System by Sam Carpenter

Work the System

Sam Carpenter

Written by an owner who almost lost his business before he realized the company was just a collection of broken systems. The mindset shift that pulls a lot of operators out of the weeds.

Fix This Next by Mike Michalowicz

Fix This Next

Mike Michalowicz

A diagnostic for figuring out the one thing in your business that's actually choking growth, instead of fixing five things that don't matter.

All In by Mike Michalowicz

All In

Mike Michalowicz

The follow-up that makes the case for building a team that's actually invested — not just employed. Hiring, retention, and culture in plain language.

Buy Back Your Time by Dan Martell

Buy Back Your Time

Dan Martell

The delegation framework that fixes the trap of owning a business that's secretly owning you. The replacement ladder, the buyback rate, the audit — all useful.

Built to Sell by John Warrillow

Built to Sell

John Warrillow

Even if you never plan to sell, this is the most useful exit-planning book on the shelf. Building a sellable business is the same as building a business that's actually a business.

Risk & Insurance Thinking

How professionals actually think about uncertainty — and why most of us underestimate the tail.

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Against the Gods by Peter L. Bernstein

Against the Gods

Peter L. Bernstein

A history of risk itself — from medieval merchants to modern markets. The single best book for understanding why insurance exists and what it's really pricing.

Antifragile by Nassim Nicholas Taleb

Antifragile

Nassim Nicholas Taleb

The book that reframes how to position a business against shocks you can't predict. Required reading before you decide your deductibles are "high enough."

Thinking in Bets by Annie Duke

Thinking in Bets

Annie Duke

Written by a former pro poker player. Teaches you to separate decision quality from outcome quality — the skill that keeps people sane during a bad year.

The Obstacle Is the Way by Ryan Holiday

The Obstacle Is the Way

Ryan Holiday

A modern read of Stoic philosophy aimed at the moments when something has gone wrong. Useful in claim season, hard-market season, and most Tuesday afternoons.

Understanding the Commercial General Liability Insurance Policy by Dwight M. Kealy

Understanding the CGL Policy

Dwight M. Kealy

The cleanest plain-English walkthrough of a CGL form we've found. If you've ever had a coverage argument come down to one endorsement, this is the book to keep nearby.

Workers Compensation in Two Hours by Nancy Germond

Workers' Comp in Two Hours

Nancy Germond

A short, no-nonsense primer on how workers' comp actually works — what's covered, what's not, and the levers that drive your mod. We hand this out at meet-and-greets.

Finance & Profit

Cash discipline, pricing power, and the money skills schools never teach.

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Profit First by Mike Michalowicz

Profit First

Mike Michalowicz

A cash-management system that takes ten minutes to explain and ten years to outgrow. If your business is profitable on the P&L but always broke in the bank, read this twice.

The Psychology of Money by Morgan Housel

The Psychology of Money

Morgan Housel

Twenty short chapters on why smart people make dumb money decisions — and how to do less of it. The best gift for a partner or adult child who's just starting out.

Buy Then Build by Walker Deibel

Buy Then Build

Walker Deibel

The case for buying an existing business instead of starting from zero. Useful even if you're not acquiring — it teaches you what makes your own business worth more.

Secrets of Sand Hill Road by Scott Kupor

Secrets of Sand Hill Road

Scott Kupor

An a16z partner's plain-English explanation of how venture capital really works. Even if you'll never raise — the way VCs evaluate businesses is the way smart buyers do too.

Angel by Jason Calacanis

Angel

Jason Calacanis

Calacanis on what makes him write a check. The investor-side view that flips your thinking on what your own business looks like from across the table.

The Diary of a CEO by Steven Bartlett

The Diary of a CEO

Steven Bartlett

Thirty-three "laws" pulled from years of interviewing builders. Read the law titles, skip the chapters that don't apply, and let the rest re-frame how you think about your role.

Leadership & People

The job nobody trained you for: leading other adults.

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The Hard Thing About Hard Things by Ben Horowitz

The Hard Thing About Hard Things

Ben Horowitz

The honest version of running a company. Layoffs, demotions, near-bankruptcies — the parts the highlight reel skips. Read this when things are going badly; it will help.

Atomic Habits by James Clear

Atomic Habits

James Clear

The cleanest framework on the shelf for building consistent behavior — yours and your team's. Short chapters, immediately applicable.

Extreme Ownership by Jocko Willink and Leif Babin

Extreme Ownership

Jocko Willink & Leif Babin

Written by two former Navy SEALs. The premise: as the leader, everything that goes wrong is your fault — and that's a freeing place to operate from.

Start with Why by Simon Sinek

Start with Why

Simon Sinek

The original Golden Circle argument. The reason your team underperforms is rarely incentives — it's usually that nobody explained the why clearly enough to repeat.

Leaders Eat Last by Simon Sinek

Leaders Eat Last

Simon Sinek

Sinek's case for the leader's actual job: making people feel safe enough to do real work. The Circle of Safety lands hard if your team is quietly burning out.

High Output Management by Andrew S. Grove

High Output Management

Andrew S. Grove

Andy Grove's manual from Intel's peak. Forty years old and still the cleanest book on what a manager's job actually is. Required reading before promoting your first manager.

Who Not How by Dan Sullivan

Who Not How

Dan Sullivan & Benjamin Hardy

The premise: stop asking how to do something and start asking who could do it for you. The mental flip that breaks bottleneck-shaped owners.

Trillion Dollar Coach by Eric Schmidt

Trillion Dollar Coach

Schmidt, Rosenberg & Eagle

What Bill Campbell actually coached the Steve Jobs / Larry Page / Sundar Pichai bench on. Mostly: how to run a real one-on-one and how to disagree without breaking the team.

Entrepreneurial Leap by Gino Wickman

Entrepreneurial Leap

Gino Wickman

The diagnostic for whether you're actually built to be the owner — and what to do if the answer is yes. The companion piece to Traction for people earlier in the journey.

Build by Tony Fadell

Build

Tony Fadell

The guy who built the iPod and the Nest thermostat on how products and people actually get made. Practical, candid, and unusually generous with the inside view.

Think Again by Adam Grant

Think Again

Adam Grant

The case for changing your mind on purpose. The chapters on the preacher/prosecutor/politician modes will rewire how you handle a hard disagreement.

Negotiation & Communication

The conversations that decide more than your strategy does.

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Never Split the Difference by Chris Voss

Never Split the Difference

Chris Voss

Written by an FBI hostage negotiator. The tactics translate one-for-one to vendor contracts, claim disputes, and the hardest conversations with co-owners.

Influence by Robert B. Cialdini

Influence

Robert B. Cialdini

The original textbook on persuasion. Forty years old and still the most-cited book in marketing, sales, and behavioral science for a reason.

Crucial Conversations

Crucial Conversations

Patterson, Grenny, McMillan & Switzler

How to talk when stakes are high, emotions are running, and opinions vary. The closest thing to a manual for the conversations owners avoid for too long.

The First Minute by Chris Fenning

The First Minute

Chris Fenning

How to open a conversation so the other person actually knows what you want from them. Underrated, short, and immediately useful in meetings and emails.

Who is in the Room by Bob Frisch

Who's in the Room?

Bob Frisch

Why most leadership-team meetings produce nothing. Frisch's fix — separate decision groups for separate decisions — saves a lot of wasted Mondays.

Who is in Your Room by Ivan Misner

Who's in Your Room?

Ivan Misner & Stewart Emery

A different angle on the same question: who gets access to you, and what is that access costing you? A short read with surprisingly long aftereffects.

Sales & Marketing

How modern businesses actually get found, get chosen, and get bought from.

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They Ask You Answer by Marcus Sheridan

They Ask, You Answer

Marcus Sheridan

A pool-installer turned marketer's playbook for answering the questions buyers are actually asking. The cleanest argument for content-as-trust we've read.

New Sales Simplified by Mike Weinberg

New Sales. Simplified.

Mike Weinberg

The most no-nonsense book on outbound on the shelf. Weinberg has no patience for excuses and it shows in every chapter.

Fanatical Prospecting by Jeb Blount

Fanatical Prospecting

Jeb Blount

The companion to Weinberg — Blount's argument is that pipeline failure is almost always activity failure. Read it when your numbers are dipping.

The Ultimate Sales Machine by Chet Holmes

The Ultimate Sales Machine

Chet Holmes

The Dream 100 framework lives here. Twelve disciplines, but you only need to nail three of them better than your competitors to win.

The Ultimate Sales Letter by Dan S. Kennedy

The Ultimate Sales Letter

Dan S. Kennedy

Kennedy's direct-response writing handbook. The frameworks are forty years old and still outperform most modern copywriting advice.

Purple Cow by Seth Godin

Purple Cow

Seth Godin

Godin's argument that boring is fatal, in plain English. Useful pre-rebrand or pre-website read; he'll talk you out of doing the safe thing.

DotCom Secrets by Russell Brunson

DotCom Secrets

Russell Brunson

Hold your nose at the sales pages — the funnel theory behind it is solid. The value-ladder chapter alone has helped a few of our friends triple their lead flow.

Expert Secrets by Russell Brunson

Expert Secrets

Russell Brunson

The follow-up — same caveats, same usefulness. The chapter on "the attractive character" is the cleanest writeup of personal-brand positioning around.

Traffic Secrets by Russell Brunson

Traffic Secrets

Russell Brunson

Brunson's playbook for finding your buyers in their existing watering holes instead of starting from zero. Helpful even if you only run a referral business.

SEO for Growth by John Jantsch and Phil Singleton

SEO for Growth

John Jantsch & Phil Singleton

Approachable, non-spammy SEO for small businesses. The strategic chapters age better than the technical ones — but the strategic chapters are the ones that matter.

Strategy & Growth

How category leaders pick their fight, and how everyone else can compete on terms they actually win.

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Play Bigger

Play Bigger

Ramadan, Peterson, Lochhead, Maney

The case that creating a category beats winning one. Most useful for the owner who keeps describing their business as "better" instead of "different."

Hacking Growth by Sean Ellis

Hacking Growth

Sean Ellis & Morgan Brown

Where the term "growth hacking" actually comes from — and why the original meaning is still useful: cross-functional teams running tight experiments against one north-star metric.

The SaaS Playbook by Rob Walling

The SaaS Playbook

Rob Walling

Even if you don't run software, the bootstrap-first chapters on pricing, niching, and avoiding VC are the cleanest version of that argument we've seen.

Virtual Freedom by Chris Ducker

Virtual Freedom

Chris Ducker

The book that pushed a lot of solo operators into their first hire. Practical, slightly dated on the tools, evergreen on the mindset of buying back your calendar.

The 29 Percent Solution by Ivan Misner

The 29% Solution

Ivan Misner & Michelle R. Donovan

Fifty-two structured networking habits, one per week. Boring on the surface, useful in practice — most independent agencies live or die on the back of executing this stuff consistently.

Power, Strategy & Mindset

Older books with sharper teeth. Read carefully — they describe the world, they don't endorse it.

Use the arrows to browse — or swipe / drag the shelf directly

The Art of War by Sun Tzu

The Art of War

Sun Tzu

Two-thousand-year-old strategy text. The chapters on knowing the terrain and choosing your battles are uncomfortably applicable to small-business competitive dynamics.

The 48 Laws of Power by Robert Greene

The 48 Laws of Power

Robert Greene

Less a how-to manual than a field guide to the games people are already playing around you. Knowing the laws is what keeps you from being on the wrong end of one.

The 50th Law by 50 Cent and Robert Greene

The 50th Law

50 Cent & Robert Greene

Curtis Jackson and Greene's collaboration on fearlessness. The biographical chapters land harder than the philosophy chapters; both are worth the time.

How a Book Earns a Spot

Someone on our team has read it

Cover to cover, not skimmed. If we haven't read it, it doesn't go on the shelf — even if everyone else is recommending it.

It helps a real client problem

Each book maps to a conversation we keep having — succession, cash flow, hiring, partner disputes, exit planning, big life decisions.

It ages well

No flavor-of-the-month titles. We favor books that have proven their value over years, not just the latest bestseller cycle.

Reading the Books Is the Easy Part

If you want to talk through how any of these ideas apply to your situation — coverage, succession, risk, growth, or just figuring out what to do next — we're a phone call away. That conversation is free, and it's how most of our best client relationships start.