Writing on Entrepreneurship
How AI is Going to Change Digital Agencies Forever
When I started Draft.dev in 2020, our value proposition was built on a “high-touch, high-quality”...
Maximizing for Energy
I have been self-employed for over five years now, and ever since the beginning, I...
Why Startup Consulting is a Bad Idea
One of the most common mistakes new consultants make is focusing on the market they...
How I'm Scaling My Productized Service Business
When I left my job to start Draft.dev a few years ago, I knew there...
Startup Working Hours: Burnout, Pacing, and Hustle Culture
When I joined my first startup 15 years ago, the prevailing wisdom said that you...
Rebuilding Draft.dev for 2026 and Beyond
As a company, Draft.dev has been a wild ride. I started the company in 2020...
How to Sell Your Digital Marketing Agency
In 2022, I started the process to acquire a second digital agency. I had started...
Building a Business Without Slack
In 2020, I read two books that changed my perspective on work. The first was...
Best Remote Job Boards for Agencies to Find Talent
Digital agencies are all about people. That means finding the right talent at the right...
Entrepreneurial Leadership: Inspiring, Aligning, and Managing Your Team
You might think that leadership is synonymous with entrepreneurship, but I find that a lot...
The Role of Fear in Entrepreneurship
Fear has been both a fantastic motivator and the biggest limiting factor I have faced...
Agency Finance 101: Insights from the CFOs
Like many digital agency owners, I didn’t start my agency with a well-thought out financial...
12 Entrepreneurship Books That Impacted Me the Most
Books have made a huge impact on my career as an entrepreneur, but the problem...
30 Side Project Ideas to Earn Extra Money and Build New Skills
For the first 10 years of my career, I had many side projects with varying...
Belief => Actions => Results
A couple of years ago, I started to build a big vision for my business....
Running My Business From an iPad (2024 Update)
In 2021, I first tried to do all my work from an iPad. Back then,...
Security Tips for Early Stage Startups
It’s rare for small companies to make security a high priority, but it’s an increasingly important...
Should You Build a SaaS for Agencies?
Being that my background was in funded tech startups and I now run two digital...
The Cold Sales Trap
Entrepreneurs who are just getting started often spend too much time figuring out their offering...
Decision Fear and Decision Fatigue
Among the challenges I did not expect when starting a business was the constant stream...
How Do Open Source Companies Make Money?
Since starting Draft.dev in 2020, I’ve had the opportunity to work with dozens of open...
Why 2023 Was My Hardest Year So Far
If you follow me on social media or hear me on podcasts, you probably think...
Defining a Big Vision
When I started my Draft.dev in 2020, my goal was to build a business that...
15 Things I've Learned About Founder Sales
One of the first roles founders take on is that of sales leader. In fact,...
Buying a Business: Acquiring The Podcast Consultant
In 2022, my company, Draft.dev was growing rapidly. My team was solidifying and I had...
Scaling to $1 million: What You Need to Do to Beat 91% of Businesses
Only 9% of small businesses reach $1 million or more in revenue. This is shocking...
Parenting While Entrepreneuring
Having kids is a valuable experience for entrepreneurs. I’m not saying it’s easy. It’s way...
24 Startup CTO Interview Questions
Hiring a Chief Technology Officer (CTO) is a difficult feat at the best of times....
Paths Up the Mountain
You are finally ready to climb the mountain. You’ve spent 10 years learning, preparing, and...
How to Hire at a Startup
Hiring is always hard. Even with 10 years of experience leading teams at startups, I...
You Want to Start a Business, but do You Really Want to be a CEO?
I went to MicroConf for the first time a couple of weeks ago. While I...
The 8 Types of Entrepreneurship
I recently joined Entrepreneurs’ Organization (EO), a peer group for business owners with chapters across...
Creating Your First Affiliate Marketing Website [Checklist]
There are lots of ways to make money online, but one of the oldest is...
Startup Funding Without Giving Up Equity
If you spend much time in online forums about startups, one of the most persistent...
Productivity for Entrepreneurs
“Every human has a finite number of heartbeats. I don’t intend to waste any of...
How Niching Down Can Help Your Business Grow
Last year I took a leap. After years of working with startups, I decided I...
10 Years of Indie Hacking to an Overnight Success
I’m basically living the indie hacker’s dream. I run a small, profitable, bootstrapped business that...
20 Questions to Ask an Entrepreneur Before Joining Their Startup
I’ve had three jobs with startups where my ultimate interview was directly with the founders....
Q&A: Decreasing Risk as an Entrepreneur
Question What is one way for an entrepreneur to decrease risk when starting a business?...
What Does It Take to Become a Serial Entrepreneur?
An entrepreneur comes up with an idea and creates a new business out of it,...
Q&A: Common Mistakes Growing Small Business Owners Make
Question What is a common mistake that small-business owners make when their businesses begin growing?...
How We Found Our First 30 Clients
It’s been less than a year since I started Draft.dev and we’ve already built up...
The Entrepreneur's Salary Guide
When I started my business last year, I knew I wanted to pay myself something...
Finding a Great Business Advisor
I’ve always been very intentional about building my network, so when I started Draft.dev it...
The Best Startup Project Management Tools
How do you manage your project workflows? Effective project management is crucial to the success...
Starting a Software Startup the Lean Way
Some believe that creating a successful software startup is about nothing more than making a...
The Startup Website List: 25 Inspirational Examples
A friend recently asked me for help with her startup’s landing page. While I’m not...
In Defense of Simple Business Models
The two fastest ways to kill your startup are: Having no business model. Having an...
The Founder's Guide to Stealth Startups
I remember the first time I sat down for a job interview with a startup...
High Tech vs. Tech-Enabled Startups
I was talking with an entrepreneur and investor here in Chicago recently, and he pointed...
Building a Great Startup Culture
I once shared office space with a quickly-growing startup in downtown Chicago. This company seemed...
How to Find a CTO: Tips for Non Technical Founders
I’ve worked in startups my whole career, first as a software engineer, then as a...
Defining Trends of the 2020s
A lot has happened in 2020. As this strange and unsettling year comes to a...
The Danger in Listening to Experts
“Most of all, there is this truth: No matter how great your teachers may be,...
Why I Left a Career as a Startup CTO to Become a Writer
When I graduated from college, my dream was to lead a team at a startup....
The Many Roles of a Startup CTO
“Chief Technology Officer” (or “CTO”) sounds like a glamorous title. It’s right up there with...
Knowing Your Startup's Technical Maturity Level
As a startup developer I’m always trying to strike a balance between pragmatism and optimization....
Knowing When Your Business is Ready to Launch
I can’t tell you how many conversations I’ve had with entrepreneurs who fit into the...
The Risk in Sending Your Startup's Technology Offshore
When I wrote this in September, 2014 I was managing an offshore dev team for...
Health as a Long Term Investment in Your Success
I first published this post in February, 2015 when I was just getting back into...
Everybody's Got an Idea. Ideas Suck. Action Doesn't.
“Amateurs sit and wait for inspiration, the rest of us just get up and go...
How Startups Know When They've Got the Technology Right
I wrote this post back in September of 2012. I had just started my first...
Determining the Value of Online Data
Since I wrote this post back in May, 2012, many more online companies have been...
Where Have All the Business Models Gone?
When I wrote this article in April of 2012, Instagram had just been bought by...
Training for Focus: 4 Ways to Keep Your Eyes on the Big Picture
I used to struggle with staying focused. Since I first wrote this article in March,...