Writing on Startups
Buying a Business: Acquiring The Podcast Consultant
In 2022, my company, Draft.dev was growing rapidly. My team was solidifying and I had...
The Role of Fear in Entrepreneurship
Fear has been both a fantastic motivator and the biggest limiting factor I have faced...
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...
On Taking Breaks
I’ll be honest, I’ve never experienced burnout. I’ve always enjoyed my work, especially since I...
Startup Leadership: Setting Goals and Getting Buy-in
Almost two years after starting Draft.dev, I took a step back and realized that my...
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...
The 11 Best Payroll Software Tools for Startups
Last year, I went through the process of evaluating payroll software tools, so I figured...
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...
30 Side Project Ideas: Earn Money and Build New Skills Without Leaving Your Day Job
I started many side projects of varying success before going full-time on my own business...
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...
Why Marketing Management is so Hard in Startups
I’ve gotten to know a lot of marketing managers at startups since I started working...
Entrepreneurial Leadership: Inspiring, Aligning, and Managing Your Team
I was having a conversation with a friend recently and she told me about her...
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?...
Running My Business From an iPad
Earlier this year, I decided to get an iPad as a more portable work device....
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 Business Advisor for Your Startup
I’ve always been very intentional about building my network, so when I started Draft.dev it...
Building a Business Without Slack
Last year, I read two books that changed my perspective on work. The first was...
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...
How I'm Scaling My Service Business
When I left my job to start Draft.dev last year, I knew there were pros...
How Do Open Source Companies Make Money?
A few weeks ago post, I wrote about the case for simple business models in...
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...
Using the Bubble App Builder to Launch Your Startup Faster
There are an average of 12,000 new startups founded daily in the US. To gain...
What it's Really Like Working for a Startup
After almost ten years working for startups, I’ve seen some pretty wild things. One startup...
Why Startup Consulting is a Bad Idea
One of my friends recently brought up the idea of consulting for startups. He’s been...
Maximizing for Energy
When left my full-time job last year, I started thinking about the lifestyle I wanted...
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...
Startup Working Hours: Burnout, Pacing, and Hustle Culture
When I joined my first startup almost ten years ago, most of the prevailing wisdom...
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...
The World Needs a Non Profit Search Engine
Google is the most widely-used search engine in the world, and the company now offers...
The Best Startup Books for Founders
As a startup founder, you get pulled in a million different directions from the moment...
Defining Trends of the 2020s
A lot has happened in 2020. As this strange and unsettling year comes to a...
Essential Reading for Startup CTOs
Being a great CTO requires insight and vision in both technology and business. You have...
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 Evolution of Our Product Management Process
In 2016 when I joined The Graide Network, I was the first developer. With the...
10 Web Application Builders for Non-Technical Startup Founders
In the days of Web 1.0, entrepreneurs had to learn code or hire web developers...
The Myths You’ll Hear About Working as an Engineer at a Startup
When I first graduated from college and went looking for a job with 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...
Using Medium for Your Startup's Blog
How large is your online footprint? Marketing your startup is a matter of getting your...
Say No
People will continue to request more of your time until you say no. I was...
Stop Working and Let Someone Else Build It
My backlog of project ideas is long. Like, ridiculously long. Even though I clean it...
Web Applications: The Guide for Building Webs Apps Without Code
Web applications are getting more and more popular, but in 2018, what’s the best way...
Writing Less Software to Accomplish More
Creating custom software should be the last resort for early stage startups. Writing good software...
Startup Employees Still Need a Financial Plan
I know this is a little off base from my usual posts about software, technology,...
How to Put Your Startup's Marketing on Autopilot
I’ve been spending a little time every week promoting the Side Project Marketing Checklist I...
The Side Project Marketing Checklist: Making it Go Viral
Like many developers, I’ve been building side projects in my spare time for years. One...
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...
Security Tips for Engineers at Early Stage Startups
Since publishing this post in August, 2015 I’ve become somewhat fanatical about getting my company’s...
Why the Textbook Industry is Ripe for a Technological Revolution
When I first wrote this in September, 2014 I was just a few months in...
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...
Marketing isn't about Content Creation, it's about Platform Creation
Back when I was first starting out, I was actually more interested in technical marketing...
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...
Stress a Little, It's Okay
I’ve always been pretty good at dealing with stress, but as I get older and...
Placing Blame: Internally or Externally
There are two kinds of people in the world: Those who take responsibility when they...
Determining the Value of Online Data
Since I wrote this post back in May, 2012, many more online companies have been...
My Beef With Twitter: Taking the Engagement Out of Social Media
In 2012 when I wrote this post I was getting jaded with Twitter. For about...
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,...
Community Is About Engagement, Not Size
Back in March, 2012 when I wrote and first published this post and was doing...
Business Blogging Without the Lies
This post was originally published in March of 2012, and since then the world of...
Messaging as a Platform
Messaging platforms like Slack, Snapchat, WeChat, Allo, and What’s App are all the rage -...
Planning for Retirement While Working at a Startup
As I’ve entered my late 20’s and begun to solidify my career path in startups,...
Joining The Graide Network as Chief Technology Officer
After over 2 and a half years at Packback, I’ve decided to move on and...
An Update on Engineering at Packback
As I enter my second full year of working with Packback, I can say that...
On Leaving Uloop for Packback Books
This month marked the end of my first startup experience and the beginning of my...