After working as a software engineer at several early-stage technology startups, Karl Hughes has decided to pursue entrepreneurship full time with his company, Draft. For the past 10 years Hughes has been blogging casually, only recently starting to sell his skills to companies. In light of the Coronavirus and reduced hours at his job, Hughes decided to go full time into his venture which provides technical content for software engineering blogs. Although still very new at running his own business, Hughes has tons of experience working for others in the startup space and has plenty of valuable insights into what it is like to actually take the risk and start your own business.
Can you share a little bit about your background? What was your old job? How did you get into writing?
I've been a software engineer at early-stage technology startups in Chicago for the past 8 years. I was the first technical hire for two companies and most recently I led a small team of engineers as the CTO at The Graide Network.
Writing has always been one of my hobbies, but I was cautious to pursue it as a career because it's so hard to make a living at. After blogging casually for almost 10 years, companies started to reach out and ask if I would be willing to write technical blog posts for them. After doing a few for free, a couple offered to pay me.
How did you discover this niche in the writing world?
In May of this year, the company I was working for hit a rough patch due to Coronavirus and decided to put me and the rest of the engineers down to half-time. I figured I would do more freelance writing to fill my time and make some extra cash.
Within a couple of weeks, I had more work than I could handle. As I talked to people in the industry, I realized that finding good freelance technical writers was a huge challenge, so I started Draft to help meet that need.
How do you plan on beating out the competition?
There's a common feeling held by would-be entrepreneurs that you have to beat out your competition, but in many markets, that's not true. You just have to find enough customers to sustain yourself.
People seem to forget that Lyft didn't beat Uber, yet both of them still exist. While Uber might be bigger, Lyft did just fine by most startup standards.
My goal is to pay myself a living wage, learn more about the non-technical side of running a company, and provide a valuable service to my clients. Because this is a growing market (companies running software engineering blogs), I don't have to beat all my competitors in every aspect, I just have to offer something that provides value to 10-20 customers.
When I look at the business that way, it seems very do-able.
How did you decide it was time to start being your own boss? Can you walk me through that decision?
In January, I started thinking that I was ready for a new challenge. First, I looked into middle-management positions with larger companies. I quickly realized that path was not for me, so I started thinking: what would it take for me to start my own business?
I've always been entrepreneurial, but something - timing, fear, finances - always held me back. I decided that 2020 was going to be my year, but I wasn't sure what I was going to do yet.
Then, when Covid-19 forced me to half-time, I realized it was a perfect moment to transition into self-employment. I will be spending the next few months helping my current employer replace me part-time while I start my technical writing agency, Draft.
To be honest, if I hadn't been forced to half-time, I may not have made this leap so soon.
How are you validating the risk of entrepreneurship?
I've been in high-risk startups for a while now, so I'm used to the reality that I could lose my job anytime.
To combat that, I've invested heavily in my network and knowledge. As I considered what my life would be like if Draft fails, I realized that doing it would only increase my network and the amount of knowledge I have. In other words, it's not going to be harder to find a job in a year than it would be if I started looking for one right now.
I'll also add that I'm in an extremely fortunate and privileged position. For the past year, I've been saving money and my wife has a stable job with health insurance benefits. If I were the sole breadwinner in my family, entrepreneurship probably wouldn't be an option.
How have you put yourself out in the public so far? What is your method of advertising?
My best leads have been through my personal connections. I imagine that will be true for the first couple of years.
But, I'm investing in a blog, my personal social media presence, and some high-value resources for my target market. For example, I'm currently finishing up a free course for technical blog managers. My service isn't cheap, so I have to build trust with people before they're likely to make a purchase. Giving away valuable knowledge is a great way to build it.
What is the best part about this whole process? What is the worst part?
The best and worst part is the uncertainty.
I have been running small engineering teams and building software for early-stage startups for long enough that I know most of the challenges that we're likely to face. As soon as I started this business, I started waking up in the middle of the night with a gnawing fear that I'd write a terrible article and all my clients would leave me.
At the same time, that uncertainty is wildly motivating. If I don't figure out how to write good content, hire more writers, and find more clients this whole venture will fall apart and I'll have to go back to the job search without the luxury of having some money saved up.
Where do you have to devote most of your time?
Currently, I spend about half my time delivering value for existing clients (writing, planning content, researching, etc.) and half my time looking for new clients.
Once the business gets more mature, I'd like to spend all my time focused on growth and client relationships and have writers and editors doing all the production. I'm hoping I get there within 2-3 years, but it's hard to say at this point because the venture is so new.
What is some of the best advice you can give to aspiring entrepreneurs?
Be careful when you take advice from experienced entrepreneurs. They're so far ahead of you that their advice probably isn't what you need. Instead, focus on small wins that will help you build confidence.
For example, before I decided to go full-time on Draft, I ran a newsletter called CFP Land. I figured out how to grow it to 2000 subscribers and make $300/month from it. Before that, I wrote a book that sold almost 1000 copies. Before that, I wrote a bunch of job board software that made a total of $200.
My point is that you're seeing me a lot further along in my journey than it seems. While it's month 1 for Draft, I've been exploring and testing and learning for almost a decade now.
I'm always open to helping aspiring entrepreneurs out. Feel free to reach out on Twitter if I can help.
• Heavily invest in your networks and in learning new skills
• Focus on building trust with your customers
• Entrepreneurship is a marathon not a sprint - you need to focus on the small wins to help propel yourself forward
My Favorite Quotes:
• “There's a common feeling held by would-be entrepreneurs that you have to beat out your competition, but in many markets, that's not true. You just have to find enough customers to sustain yourself."
• “The best and worst part is the uncertainty."
• “Be careful when you take advice from experienced entrepreneurs. They're so far ahead of you that their advice probably isn't what you need. Instead, focus on small wins that will help you build confidence."