Notes on building, bootstrapping & InsurTech.
Operator lessons on leadership, capital discipline, and innovation — published regularly.
The Copilot Era Is Ending in Insurance
In January I wrote that AI had stopped being a pilot program in insurance. Six months later the ground has moved again — and the word for what's arriving is agent. Here's what that changes for carriers…
Seven Years In: What I Got Right and What I Got Wrong
The Part I Got Wrong July 2019. Rob Galbraith and I launched the InsurTech Geek Podcast with a simple premise: stop reading press releases and start talking to practitioners. Seven years and 170-plus ...…
Why the Biggest InsurTech Bets of 2021 Didn't Pay Off
The Money Went to the Wrong Place In 2021, venture capital flooded into insurtech at a pace I'd never seen. Companies were raising at 20x, 30x revenue multiples. Some were raising with no revenue at a...…
Climate Risk Isn't Coming. It's Already Here.
I've been hosting the InsurTech Geek Podcast for seven years. In that time I've talked to reinsurers, cat modelers, satellite imaging companies, parametric pioneers, and state regulators. Climate came...…
What 156 Conversations Taught Me About How Industries Actually Change
The First Episode Was Just Me Talking to a Microphone July 2019. I'm in a studio in Bryan, Texas, recording what would become the InsurTech Geek Podcast — spelled "InsureTech" with an E back then, bec...…
The Death of Disruption (And Why That's Actually Good News)
Seven years. 156 guests on the InsurTech Geek Podcast. I've sat with founders, CEOs, investors, and brokers through the full arc of what they're now calling the InsurTech cycle. And one thing I can te...…
The Year AI Stopped Being a Pilot Program
Seven Years of "We're Running a Pilot" I've been hosting the InsurTech Geek Podcast for seven years. Over 170 episodes. And for most of that run — call it 2019 through 2024 — I could predict exactly w...…
Fire Yourself From One Job a Month
Howdy! In today’s blog, I want to talk about one of the most overlooked growth levers in leadership: learning to fire yourself. Most founders think scaling means adding. Adding more……
Step Back So Your Team Can Step Up
Howdy! In today’s newsletter, I want to talk about something that comes up a lot as your company grows: You can’t be involved in everything—and you shouldn’t try to be….…
The Company Will Mirror You
Howdy! In today’s blog, I want to talk about something I’ve seen play out in every company I’ve built: Your team will mirror your leadership. That means your communication style….…
Don’t Let a Forecast Fool You
Howdy! In today’s newsletter, I want to talk about something we all love to build, and almost always get wrong: forecasts. Revenue projections, growth models, burn-rate scenarios, you name it…we……
Teach Your Team to Think Like Owners
Howdy! In today’s newsletter, I want to talk about one of the biggest unlocks for growth that most founders overlook: You can’t scale yourself—but you can scale your mindset. One……
Vision Is a Muscle, Not a Lightning Bolt
Howdy! In today’s blog, I want to talk about one of the most overhyped ideas in entrepreneurship: That vision shows up like a lightning bolt. The myth goes like this:……
The Best Leaders Shrink the Gap Between Decision and Action
Howdy! In today’s blog, I want to talk about something that separates good leaders from great ones: how fast decisions turn into action. It’s not just about being decisive; it’s……
Your Values Shouldn’t Flex. Everything Else Can.
Howdy! In today’s blog, I want to talk about one of the most important lines a founder needs to draw and protect. Your values should be fixed. Everything else is……
Your First 5 Hires Will Make or Break You
Howdy! In today’s blog, I want to talk about one of the most important and also most overlooked decisions you’ll make as a founder: who you hire first. The first……
When to Let Go and When to Dig In
Howdy! In today’s blog, I want to talk about something almost every founder will encounter, but not enough of us have spoken about honestly: when to pivot and when to……
The Culture You Build Is the Company You Build
Howdy! In today’s blog, I want to talk about something that might not show up in your metrics, but it runs the whole machine: your company is your culture. Not……
This is What Separates Survivors from Strugglers in Business
Howdy! In today’s blog, I want to talk about something that doesn’t get enough credit in the world of startups: resilience. It’s nothing flashy, and it’s definitely not going to……
Decision Debt: What It’s Costing You
Howdy! In today’s blog, I want to talk about something that can slow down your business even more than bad strategy, weak tools, or low revenue: indecision. I call it……
Build It Like You’re Keeping It
Howdy! In today’s blog, I want to talk about a mindset shift that’s served me well for over two decades of building companies: Build it like you’re keeping it. Even……
The Danger of Chasing Vanity Metrics in Startups
Howdy! In today’s blog, I want to talk about a trap I’ve seen far too many founders fall into—chasing vanity metrics. When the numbers look that good on paper, it’s……
Don’t Delegate What You Don’t Understand
Howdy! In today’s blog, I want to talk about a mistake that nearly every founder has made at some point — delegating far too soon without having any idea of……
Are You Bleeding Cash Without Realizing It?
Howdy! In today’s article, I would like to discuss something I believe destroys many bootstrapped businesses: unnecessary spending. When you’re bootstrapping, every dollar counts. Despite this,……
The Secret to Innovation—Unhinging Your Brain
Howdy! In today’s blog post, I want to discuss the power of rethinking and how challenging your own assumptions can fuel innovation. Something to know about me: I like things that unhinge……
Proven Processes, Better Results – Find Out How
Howdy! In today’s blog post, I’ll explore why people feel the need to reinvent processes—and a simpler way to run your business. The reality is that you don’t have to reinvent……
Stop Lying To Yourself About Debt
Howdy! In today’s blog post, I want to discuss why it’s important to stop lying to yourself about debt and steps for how to get out of the hole. Whether you……
To Disrupt or Be Disrupted, That Is The Question
Howdy! In today’s blog post, I want to discuss the power of business disruption and the importance of paying attention to what’s happening around you. How many stories do you need……
This Is What Really Drives Success
Howdy! In today’s blog post, I want to discuss the unspoken power of being committed to your team. Since starting my business in the early 2000s, we’ve changed industries and faced……
Why I Chose Growth Over Comfort (And What I Learned)
Howdy! In today’s blog post, I want to discuss the difference between lifestyle and growth businesses. Both operate on fundamentally different philosophies, let me tell you why 👇 Lifestyle……
Beating Murphy’s Law with Mentorship
Howdy! In today’s blog post, I want to discuss the power of mentorship in business. This topic is especially important to me because I learned many years ago that starting……
How Do You Know When It’s Time To Move On?
Howdy! In today’s blog post, I want to talk about moving on from an idea, product or business. There’s nothing worse than pouring your heart, soul, and bank account into……
The Cost of Indecision
Howdy! In today’s blog post, I want to talk about why action is always better than stagnation. When you are an entrepreneur or a corporate innovator, indecision is a luxury……
Your Secret Weapon for Business Success
Howdy! In today’s blog post, I want to talk about the character trait that helps you adapt, overcome setbacks, and keep moving forward toward success: resilience. Resilience is essential for success……
What Happens When You Get Addicted to OPM (other peoples money)
Howdy! In today’s blog post, I want to talk about what happens when you get addicted to OPM (other people’s money)—A.K.A. venture capital funding. Relying too heavily on what I like……
My #1 Tip for Maintaining Control of Your Business
Howdy! In today’s blog post, I want to talk about maintaining control of your business while growing at scale. I think control is a bit of an illusion. You can influence……
What To Do When You Face a Setback
Howdy! In today’s blog post, I want to talk about what to do when you face a setback and how to keep the bigger picture in mind. If your goal is……
My #1 Budget-Friendly Business Exposure Hack
Howdy! In today’s blog post, I want to talk about how to sell and market your product while bootstrapping. It’s no surprise that when you are bootstrapping, you don’t have a……
Capital Efficiency: The New Business Imperative
In today’s blog post, I want to discuss why capital efficiency is important in bootstrapping. Any market where you are competing against well-funded, deep-pocketed private equity and……
Are You Solving Your Company’s Biggest Problems?
In today’s blog post I want to talk about the importance of focusing on solving your company’s big problems before adding AI into the mix. Everyone is talking about large……
How to Gain a Competitive Edge as a New Business
In today’s blog post, I want to talk about VC-funded vs. bootstrapped companies and how to gain a competitive edge. Any capital-efficient business has a competitive edge. Why? because it’s……
Why You Should Put Yourself “On the Line” with Your Clients
In today’s blog post, I want to talk about gaining a new client’s trust through a system of risk and reward. We know that switching services, even from Excel or……
Focusing on Adoption
I believe there are 5 steps to follow to innovate from within, and today I want to talk about Step 5. If you missed Steps 1 through 4, check out our latest blog……
Spending Time Studying the Problem
I believe there are 5 steps to follow to innovate from within, and today I want to talk about Step 4. If you missed Steps 1, 2 & 3, check out our latest……
The Need for a Process
I believe there are 5 steps to follow to innovate from within, and today, I want to talk about Step 3. If you missed Steps 1 & 2, check our most……
Dedicated Butts in Dedicated Seats
I believe there are 5 steps to follow to innovate from within, and today, I want to talk about Step 2. If you missed Step 1, check our most recent blog……
Believing That You Can Get Things Done
I believe there are 5 steps to follow to innovate from within, and today, I want to talk about Step 1. Fundamentally, I believe that almost every company has the……
Bootstrapping is a Way of Life, Not Just Financial
The little things you do every day feed into bigger habits and end up being a part of who you are…that’s what the bootstrapping mindset is all about! It forms who you……
How To Generate Cash Immediately
I consider myself a hard worker, who is always adapting, innovating and ready to make things happen. Since I was young, I knew I wanted to build something for myself. So, here’s……
2 Things I Would Recommend To My Past Self
Today, I’m here to talk about the importance of prioritizing coaching in business and the value of clearing your schedule frequently. Prioritize Coaching I’ve mentioned previously that my dad was my……
Sticking to Company Values
Today, I want to talk about company values and the importance of defining who you are as a company. I always say that if you can’t repeat it, you don’t believe……
Learning from Other Peoples Mistakes
My accounting degree taught me a lot about how business works. I learned the ins and outs of running an effective business, but what I wanted to know was why……
How to Handle a Crisis in Business
On January 14th, 2008, I thought that my business was done for. We had a distracted employee who wasn’t monitoring his responsibilities and all of our servers from our data……
Having a VC Mindset as a Bootstrapper
The line between being a traditional bootstrapper and being a VC is starting to become more and more blurry. The difference is, as a bootstrapper, you tend to be out of……
The Importance of Mentorship in Business
In today’s blog post, I want to talk about the importance of mentorship in business. Over the years, I have had numerous mentors who have played a crucial role in……
3 Ways To Nurture Corporate Innovators
Let’s talk about ways to nurture intrapreneurs within your company. When you have long-standing employees who are passionate about what they do and the company itself, the smart thing to……
Being a Bootstrapped Entrepreneur
I’ve spent over 20 years building a business from the ground up. It has been incredibly rewarding and dare I say, fun. That’s right, the ups and downs, the highs……
Who is a Disruptor?
A disruptive person has a fairly negative connotation but hear me out. Sometimes it can be useful to be disruptive. I think it should be used as a tool to……