From Software Engineer to CTO to Indie Entrepreneur by Staying Consistent

Karl Hughes Founder of Draft.Dev

Karl Hughes transformed his path from being a software engineer to CTO (at venture-funded startups) to now being an indie entrepreneur. The key to his successful journey is consistency. Karl stresses the importance of focusing on small wins.

About This Indie Interview

This is the #5th installment of our Indie Interviews series to help aspiring indie founders & indie entrepreneurs to get inspired by listening from those successful indie founders who are already highly involved on the startup scene and *being there* taming the waves & surfing better than ever to achieve their dream – seeking financial freedom, working on projects that matters to them, getting a sense of accomplishment (in their own eyes) and working on their own schedule.

It is also an opportunity for new indie founders to get to know other like-minded indie entrepreneurs.

I hope you will derive as much fun to read my interviews as I’m having by interviewing those awesome indie founders, entrepreneurs & businesses.

And Now the Interview With the Indie Founder

### Spotlight on our today’s indie person

>> Please tell us about yourself

My name is Karl Hughes. After almost ten years as a software engineer, manager, and eventually CTO at venture-funded startups, I decided to start my own small business.

Today, I run, where I create technical tutorials and marketing content for software engineering blogs.

I have always liked writing. So when the last startup I worked for hit a rough patch and took the engineering team down to half-time, I decided I’d start picking up some freelance technical writing jobs.

I quickly found more demand than I could handle, so I started subcontracting some of the work out to other writers. Within a month, I decided to leave my job and pursue it full-time.

I have always wanted to own my own business, but until my hours got cut, I was afraid to leave a steady job for it. In retrospect, that little nudge made all the difference.

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>> Do you have a routine to start your day off

I am organized to a fault. So my days are pretty regimented.

I wake up at 5:30, walk the dog, and eat a leisurely breakfast with my wife and son. I do a quick workout, my wife goes to work, and I play with the dog and Joe for about an hour. I walk my son to school and get home at about 8:30 to start work.

I block off two periods of focused work time from 9 am-11 am and 1 pm-3 pm every day.

In between, I take meetings with prospective clients, teammates, and mentors. I try not to do more than 4 hours of focused work per day because I find that my productivity drops off a cliff if I try to do too much.

Around 3:30, I pick my son up from school and walk the dog again. I hang out with the family for a couple of hours and make dinner. I plug back in for a couple of hours of administrative work (scheduling meetings, responding to emails, Etc.) between 6:30 and 8:30 pm, then I read until 9:30 and start the whole thing over again.

I realize that this level of structure is not for everyone, but it helps me be more productive and happy.

>> How do you keep yourself motivated to achieve your goals?

I have to be learning to stay motivated. I have struggled with jobs at big companies because they are incentivized to keep you in the same role for years operating at your maximum efficiency. That is why I got into working at startups.

Building my own business is just an extension of that drive to learn.

I was at the top technical position at my previous company, so there was not much left to learn at that job. Starting Draft has opened up almost infinite new opportunities to learn new skills like sales, marketing, editing, and writing.

If it ever feels like I am not learning or growing, I will either change my business or move on to something else.

### The Indie Person as an Indie Founder/Entrepreneur

>> What change are you seeking to make to the world through your business?

I want to help more software engineers learn to write well.

I have always loved teaching and mentoring others. So the opportunity to work with other engineers around the world, creating technical content for our clients is stimulating to me.

>> The books or material you recommend?

As I was considering leaving my day job, Jim Collins’ Hedgehog Concept gave me the inspiration I needed:

If you’re new to starting a business, you have to be careful what you read. Listening to experts is fraught with peril because they are so far ahead of you.

That said, The Toilet Paper Entrepreneur and The $100 Startup were both good starter books for me.

The E-Myth Revisited was also transformational. It taught me to think in systems rather than as a practitioner.

Finally, I listened to a lot of podcasts, where entrepreneurs were documenting their journeys. It helps to know that other people are out there doing similar things when you are just getting started.

>> According to you, what is the difference between a founder and an entrepreneur? And which one are you?

Founder” is a job title indicating that you started a company.

Entrepreneur” is a character trait that indicates you have a drive to create things.

I think there are lots of good entrepreneurs who work within established companies. They might not be “founders,” but they take ownership of their work and drive results by taking creative risks.

While I write “Founder” as my job title, I think of myself more broadly as an “entrepreneur in everything I do.

>> What ONE habit played an important part for you as an indie founder?

I’ve made a habit of networking and staying in touch with people.

I got every job I’ve had due to my network. When I started Draft, I immediately pulled together a team of experienced entrepreneurs as advisors.

My first few clients came to me as a result of my network, and I imagine that will be my primary marketing channel for the first few years of the business.

### The Business of the indie person

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>> Tell us about your indie business: the beginning + how you come up with the naming?

Draft is a technical content production company.

We work with businesses who sell a product or service to software engineers and want to use blogging as a key part of their content marketing strategy.

These businesses can’t work with traditional SEO content writers because they need to put out technical content written by software engineers.

About the naming..

I know many people recommend sticking with a “.com”. But because my customers are pretty technical, I knew they would not mind a different TLD.

So, I started looking for words that indicate “writing” with the “.dev” extension, which would indicate that we wrote technical content. was available, so I grabbed it.

I like that it is short and easy to remember, but it will be hard to rank in search engines because it is such a general term.

>> What is your business model – how are you generating revenue & making it profitable?

We offer our technical content writing as a “productized service,” meaning we have standardized prices listed on the website for standard packages of content.

Clients pay a monthly fee based on the number of blog posts we create for them, so it’s generally recurring as well.

The price for this kind of content is 2-3x higher than typical non-technical blog posts because it’s so specialized, but we also have much higher costs. It’s really challenging to find software engineers who are also talented writers.

>> In the context of this indie business, what does success mean to you?

Success for Draft is pretty simple: provide enough money for me to support my family, and allow me the freedom to live the lifestyle I want.

After almost a decade with funded software startups, I’m not super bullish on the whole raising funding and hypergrowth thing. I just want to build a business that I enjoy running.

>> How are you building trust to attract potential customers?

Because Draft is a writing company, writing is also my primary trust-building and marketing channel. I publish content every week on the Draft blog (, my personal blog, and several other places around the web.

Twitter and Linkedin have also been valuable. I try to engage in conversations and post useful content on both.

### Key Learning Points

>> The hardest part about launching a business is _______?

Staying consistent.

You have to show up every day and work on things – many of which you don’t want to do.

&>> Your best advice for indie beginners

Just start.

Focus on small wins that will help you build confidence even if you don’t build a massive company on your first shot.

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.

(book link:

My point is that I wouldn’t have had the confidence to start Draft without a bunch of little wins under my belt.

>> Your advice for indie founders in general

A lot of founders spend too long executing everything themselves when they should be hiring others to carry out the processes they define.

This is a recipe for burnout.

### Sweet Self Promotion because indie founders deserves it!

>> Your project(s) that you want to share + where can you be found online & best way to reach out to you?

I also have a personal newsletter where readers can keep up with my progress building the company:

If anyone wants to reach out or keep up with what I’m doing, you can follow me on Twitter – @karllhughes.

2 Follow-up(s)

  1. Hey Karl,

    Draft.Dev has a lot to do with content writing. Any advice for founder wanting to get the hang of content writing?

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