Summary
Welcome to another episode of the Startup Junkies Podcast!
In this episode, Dwain Hebda and Kelli Reep discuss solopreneurship and freelancing with Caleb Talley, Jeff Amerine, and Matthew Ward. Dwain is the founder of Ya!Mule Wordsmiths and Kelli founded Flywrite Communications, both of which are Public Relations and Journalist agencies. They discuss engaging readers with a story, drumming up your own business, deciding when to go full-time, and much more! Thanks for listening!
Shownotes
(1:15) Introducing Dwain Hebda and Kelli Reep
(8:34) Driving your own ship as a solopreneur
(13:56) Telling a story that engages with readers
(18:59) How simplified language and a 24-hour news cycle affects communication
(22:12) Outsourcing accounting and legal responsibilities to stay above board
(29:35) Deciding to freelance full-time
(36:19) Advice for the younger self
(39:31) Wrap up
Links
Quotes
“If you can’t sell – and in this case, sell yourself – people are not just lining up outside your door because you announced to the world that you can put a sentence together. It doesn’t work that way.” (9:56)
“You have to be able to build a compelling case as to why you are going to be an expense for them that month. You have to be able to demonstrate how this is going to pay off and you have to demonstrate how you taking it off their hands actually save them money.” (10:47)
“You really do need a couple of members of your team who are versed in something you’re not versed in. And in my particular case, the best hire I ever made, the best money I spend year in and year out is an experienced accountant who could guide me through a number of different things early on.” (23:09)
“Had I jumped out on my own based on the first magazine article that I landed, I’d have been hungry really, really quick, and it just wouldn’t have worked.” (32:15)
Demystifying Solopreneurship with Dwain Hebda and Kelli Reep
Here at Startup Junkie, we know that aspiring freelancers and solopreneurs face numerous obstacles and challenges in their journey to support themselves financially on their own terms. Whether you’re deciding what type of business you should file as or when to take the leap into full-time freelancing, the answers are rarely straightforward.
In a recent episode of the Startup Junkies Podcast, Dwain Hebda and Kelli Reep joined Jeff, Caleb, and Matthew to discuss their experience as solopreneurs. Dwain founded Ya!Mule Wordsmiths in 2009, later incorporating the business in 2017. Kelli, originally a pilot, left the stratosphere for an office with air conditioning. She worked in Public Relations and Communication before beginning her solopreneurship and founding Flywrite Communications in 2003.
The Right Time to Freelance
For most, freelancing starts as a side-gig used to supplement a day job, but once they start racking up projects, the work begins to resemble a career. Inevitably, freelancers are faced with a common question: When should I quit my day job for my freelancing career?
Dwain struggled with this question for quite some time. He began freelancing in 2009 but didn’t take the leap to full-time solopreneurship until 2017. While the time might never feel right, he recommends financially preparing for the transition.
“Had I jumped out on my own based on the first magazine article that I landed, I’d have been hungry really, really quick, and it just wouldn’t have worked.” (32:15)
Kelli took a faster route to solopreneurship, but she understands the financial struggles that come with freelancing. Anytime she had a strong month, she would pay her bills in advance, protecting herself when the slow months made paying expenses difficult.
Not Only a Writer, a Salesperson
Another struggle that solopreneurs face is being their own boss. While it is a fantasy for many, it proves challenging in reality. Many writers choose their route because they don’t feel confident in their salesmanship, but Dwain says that you must be both a writer and a salesperson when you freelance.
“If you can’t sell – and in this case, sell yourself – people are not just lining up outside your door because you announced to the world that you can put a sentence together. It doesn’t work that way.” (9:56)
If you struggle with the task of marketing and selling yourself as a freelancer, Dwain encourages focusing on your clients’ ROI. How will they benefit from hiring you?
“You have to be able to build a compelling case as to why you are going to be an expense for them that month. You have to be able to demonstrate how this is going to pay off and you have to demonstrate how you taking it off their hands actually save them money.” (10:47)
Outsourcing for Professional Help
While solopreneurship implies you are on your own, you must evaluate your weaknesses and ask professionals for help. Dwain says that his best example of this type of outsourcing was hiring an accountant.
“You really do need a couple of members of your team who are versed in something you’re not versed in. And in my particular case, the best hire I ever made, the best money I spend year in and year out is an experienced accountant who could guide me through a number of different things early on.” (23:09)
If you aren’t confident in understanding of legal or tax jargon, lawyers and accountants are extremely helpful. While they can be expensive, they are rarely an investment you will regret.
Are you an aspiring solopreneur? Contact us today!
English 
Spanish 
Korean