A small podcast to help you become a better business owner

Season 1, Episode 1

Origin Stories


Get to know more about our panelists, how we got our start in the wild world of freelancing, and why we’re chatting to you about the Business of Freelancing.


Episode Panelists

  • Kai Davis
  • Reuven Lerner
  • Marg Reffell
  • Jeremy Green
  • Erik Dietrich
  • Meg Cumby

Panel Picks
Each episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they’re enjoying and recommend you check out: 

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If you’re a freelancer, then you’re not just an expert in your field. You’re also a business owner, responsible for everything from bookkeeping to marketing to customer satisfaction to business development.

On the Business of Freelancing, our panel of experienced freelancers discuss the issues that they have encountered while building up their business — and give you practical, actionable advice to take your career to the next level. We also invite expert guests to provide their opinions and perspectives on how you can better succeed in your freelance career.

Episode Transcript

Kai: Welcome to the inaugural episode of the Business of Freelancing. On today’s episode, you’ll meet the panelists and hear about our backgrounds and expertise. Thanks for tuning in.

All right folks, welcome to another episode of the Business of Freelancing. On today’s episode, we’re going to introduce you to our wonderful, wonderful panelists. So, we’re going to go around, share a little bit about our origin stories, freelancers, and what terrible heinous crimes we did to end up doing this and recording this podcast for you dear listener. We have Meg Cumby.

Meg: Hello.

Kai: Erik.

Erik: Hey there.

Kai: Jeremy.

Jeremy: Hey everyone.

Kai: Reuven.

Reuven: Hello.

Kai:  And Marg.

Marg: Hi.

Kai: And I’m Kai Davis. To kick things off, Reuven tell us a little bit about yourself, your background and what led you to working as a freelancer and consultant.

Reuven: Sure. I’m Reuven Learner. I live in Israel in a city halfway between Jerusalem and Tel Aviv called Modine, but I was born and raised in the US. I got to Israel in 1995. Basically, when I arrived, I started freelancing, I started my own little consulting company.

Starting off with web development, I have a degree in Computer Science. That led to me doing some web development back in the early 90s. Then when I came to Israel, I started doing that as a freelancer. One thing led to another and then I had a whole bunch of people working for me, about six people working for me.

Then we had this little thing called the Dot Com Implosion of 2000, and I had to lay them all off. So I’ve been freelancing for about 25 years now. I have learned all sorts of lessons along the way. Nowadays, after many twists and turns and so forth, I now mostly actually do training, corporate training in the Python language, and in Data Science.

So most days, I’m in a different city, different country, different company, teaching one of ten or so different courses. I also have a growing number of courses that I teach online. Both email-based and video courses. I’ve got a book that as of this recording should be coming out very soon.

I enjoy talking to people about training, about how to explain technology in terms people can understand, about marketing online, about running mailing lists. I will say I do this podcast for very selfish reasons, which is I enjoy getting advice from the other people on this panel. Basically, the people listening to this and I are in it for the same reason. I hope that you our listeners out there will write in with questions so that I can take advantage of the answers.

Kai: Well, excellent. Thank you. Thank you, Reuven. Jeremy, How about yourself?

Jeremy: Hey, everybody. I’m Jeremy Green. I live in Norman, Oklahoma. I am a software developer and consultant and also run a few SAASs of my own. I got started programming when I was in college, I got a degree in Computer Engineering and at the same time, I worked for a small, local independent math book publishing company, Saxon Publishers, if any of you have ever heard of that.

That was where I really got into business-focused computing. After that, a buddy of mine and I started a web development and design company that we ran here locally for about 10 years. Then we shut that down. I’ve been an independent operator ever since doing a mix of consulting and contracting, some freelance app development, some consulting on Cloud architecture and scaling.

Like I mentioned, I run a few software services on my own. Like Reuven, I am mainly here to be able to talk to all these other panelists and get fresh, input and ideas on what other people are doing just because I’ve learned a lot from listening to other people, and just seeing how they approach problems and sometimes getting bigger problems that I want to try to avoid.

Kai: Excellent. Marg, tell the listeners and us about you.

Marg: Yes, my name is Margaret Reffell in common Marg. I’m from Toronto, Canada. I grew up just outside the city, but I live downtown Toronto now. There’s often a lot of sirens going by whenever I’m trying to get some work done. I’m a web developer. I started developing about 10 years ago, I actually went to school for Human Physiology.

I took a bit of a detour after that, so I got my master’s in Physiology and after that, I started working on research, working on some shows. It was one show that I was on, was actually a cooking show. I was doing some research for the nutritional guidelines and for production, and they asked me to do some quick fixes to the website.

As soon as I started doing quick fixes to the website, I realized how much I loved just implementing something and seeing an immediate response. If you guys have ever been in research and those kinds of fields, it’s really hard to see responses to the things that you’re working on.

So, it was so satisfying being able to see that immediate response, so I was immediately addicted. I started diving in headfirst to the university of Google and university of YouTube to try to put together as many sites as I could. I eventually started making sites for my clients, started making sites for myself and I started teaching web development at a local college as well too.

So, it helped me keep on top of a new and emerging trends which has been great. In 2016 I decided to incorporate because my next big dream was more like, “I’m going to develop an agency and build a big business.”

Luckily it was great, at first, it was great at first, but then once you hit that seven or eight people you realize, Oh now my job is managing people which I now realized I don’t love… I started to lose my love for it because my job became like a fireman sort of a developer.

A small boutique agency with three developers and really great projects that we can dive into and we become almost the next attention of the client’s team which we also really love as well. The other thing is too I also I’m a nervous van lifer. So, I recently purchased about a year ago a 2013 Mercedes Sprinter that I’m in the process of totally rebuilding, so it’s taking longer than I thought it was going to be.

But trying to document the journey and take everyone on the journey of basically, since you’re able to work from anywhere in this business, we’re going to try to push that to the max. I’m going to pack up my cat and drive across North America. Hopefully, we might see you guys on the road too.

Kai: Hell, yeah. And Meg, how about yourself?

Meg: I’m Meg Cumby, a fellow Canadian. I’m through with the wagon, I’m holding Canada’s representation down here. I’m in Fredericton, New Brunswick which is very small, small, small city. If I was to talk about when I first started freelancing, it was probably as a journalist, because I took a journalism degree.

But once I got out of the university, I pretty quickly moved to Government Communications, and my big tragic event was getting laid off by the government with some cutbacks, which started me in freelancing. I had just a hell of a time, the first time I didn’t make it work really. The first time and I went back to government after nine months, but then after a little short time I was like, “No, no, I like the fresh air of nothing.”

I was like, “Well, I will give this one more shot.” Actually I like working with people that I made some connections with. So I started doing some generalist communications work as a freelancer, and after a few years of that, a lot of subcontracting with a couple of bigger clients doing some really interesting work and building some skills doing that with a business consultancy and local government.

But I really got turned on to this idea that I came up with by just talking with people about possibly doing testimonials, for consultants and coaches as a service. So, over about three years, I grew one idea for service into my entire focus. So now I do testimonials and case studies. I help consultants and coaches and a few other types of people, sometimes, mostly those types of people that don’t get client case studies and testimonials with as little awkwardness to no awkward as possible.

Kai: Excellent. Erik, how about you?

Erik: My name is Erik Dietrich. Theoretically, we have a house in a very small town in Michigan. My wife and I are digital nomads. So when we’re not in the middle of a global pandemic usually we’re spending half the year or more traveling around to different places. So my location can be a little hard to pin down, as in retrospect, in my career, I currently own a digital marketing agency.

I’m going to try to like give the abbreviated version of how I came to go from a Computer Science degree to doing that. So I went and got a Computer Science degree in the first 10 years or so of my career were fairly predictable corporate software engineering, so working software engineering jobs and climbing that ladder to architect, and a manager.

My last salary job about seven years ago now is as a CIO, and I came to the conclusion at that point in time that no matter how high I got up in the org chart, I still didn’t necessarily like not working for myself. During that same time, I got a graduate degree. After that I finished, I had some spare time. So I started moonlighting.

I really started to enjoy that, having my own clients, doing things my own way. So, nights and weekends, I was doing that for a number of years. I started to do training videos for pluralsight.com and all of that kind of whet my appetite for having my own business.

So being fed up with some of the trappings of the corporate world, I said goodbye, hung up my shingle. So from there, it was opportunistically, a lot of freelance app dev work, some freelance training work, and then consulting, subcontracting. Over the course of time, I developed this practice that was more and more niche and focused around static code analysis. So helping executives make like data-driven decisions about code bases.

None of that lends itself to what I’m doing now, which is the marketing. Basically what happened was for a lot of years, I would blog as a hobby and over the course of time these developer tool companies would reach out and say, “Hey, if we paid you would you write for our blog?”

After enough of those, I started to think, hey, maybe there’s a business to be had here. The timing was really good because I was tired of commuter travel, I was doing management consulting. So I’d spent like four years doing 100% travel, and we wanted to go and do the digital nomad thing instead.

So, I stopped doing all the rest of that, dove fully into this digital content marketing agency. That’s what I do now. It’s been about three years of that, and it isn’t completely divorced from the software world because our business targets developer tool companies, and we leverage subject matter experts like software engineers to do the right thing.

I’ve seen the freelance in the business world from a whole variety of different angles now. It’s just fun for me to look back and to do these podcasts to learn from other people and to talk about that body of experience, so always a good time to chat about these topics.

Kai: Excellent. I’m Kai Davis, a friend once remarked, I was cursed with a love of entrepreneurship at a young age and that’s absolutely hacking trail. I got started with a business things online eCommerce on eBay when I was 15 or so slinging Magic the Gathering cards, which is a super nerdy and super fun origin story.

That got me interested in “Hey, you could make money online. Let’s learn a little more about this.” Proceeded forward to get an Economics degree after I decided the other business program at the U of O just is not my thing. From there, I just kept getting more and more interested in marketing, how does online commerce work? How do we pitch, persuade, help educate somebody about a pain or a solution we have?

That just led me on a very, very interesting, and exciting road, building new businesses, testing new service offerings, testing informational products, and just building up experience as it turns into becoming a digital marketer or an internet marketer.

Right now my primary focus is helping freelancers and indie consultants get more leads for their business. I lead a daily letter on marketing and lead generation at kaidavis.com. I’m excited to be here. These are wonderful folks that I love hanging out with and doing fun internet and real-life projects with.

Honestly, like other people have said the value for me is having these cool conversations that they happen to get posted as podcast episodes completely to the side and a nice side benefit but excited to be here.

Now that you’ve heard a bit about who we are and the Business of Freelancing, why should you tune in weekly and listen to us, share our opinions and perspective? Well, because we’re all freelancers, we’re all indie consultants. We’ve had the ups and the downs when it comes to building and growing a business and we’re excited to share a few of our perspectives, our incites, and our conversations with interesting guests who will help you run a better business as a freelancer.

So, make sure you subscribe in your feed read or podcast App of choice. We’re excited for you to tune in as we keep on producing these excellent, excellent episodes. Thank you, dear listener and we’re excited to have you along on the ride.

What’s your picks for this inaugural episode? My pick of the week, yoga glow G-L-O dot com. Oh my God, I could rant about this for easily 45 minutes. It basically is everything you’ve ever wanted in terms of yoga practice in the palm of your hand on your phone. It’s 19 bucks a month and it has let me start building a regular yoga practice and just stretch out hunchback computer neck or just help me stretch my body out after I spent a little too much time staring at the phone.

But 19 bucks a month, a huge library of hundreds of different yoga lessons from 10 minutes to 60 minutes with or without prompts in different styles. It truly is making a huge difference in how my body feels. So if you’re a freelancer listening to this and you say man after another 14-hour session in the chair my back you know, it’s a little creaky go to glow.com G-L-O dot com and sign up today. Your friend Kai tells you, you should love it.

Reuven: But wait, there’s more.

Kai: Mhmm. Reuven, how about you?

Reuven: My pick for this week is CleanShot. So I’ve been using a Mac for a number of years. I’ve been doing screenshots for a while and that comes with a built-in screenshot maker. When I heard a few months ago that there was this third party tool that you could buy. I thought to myself, “Okay, who’s gonna buy the screenshots?”

I did and I was delighted and they recently came out with a new version and now I’m over the moon with it. CleanShot, you wouldn’t expect a lot from something that does screenshots but I found myself just the last two-three days before recording this, twice or three times a day, using it to record an animated GIF, uploaded to a forum, let people see exactly what they should be clicking on.

It really has made something that was a rarity in my work now a pretty casual thing that I do. So I definitely recommend people with Mac’s, people who want to communicate with other people, CleanShot is great.

Kai: I’ll strongly echo Reuven’s recommendation. I’ve been on the third-party screenshot app on Mac bandwagon for a while but I just switched to CleanShot last week and it’s blowing my mind really, really a great piece of software. Jeremy, how about you?

Jeremy: I don’t really have any software or anything to recommend this week. So I’m going to pick an EP that my band released at the end of last year. The band is called Layer Cake. The EP is titled, Guesstimate Jones. You can find us at our website layercake.band, or you should be able to find it on any streaming services that you look for. It’s bluesy, funky blues type of stuff, drums, bass, guitar, piano, if you’re into that kind of stuff. Give it a listen let me know anything.

Kai: Meg, how about you?

Meg: I’m going to go with for my pick this week I think I’ll go with Atomic Habits by James Clear. It’s a book by James Clear and I think it’s probably getting quite well known now but if you haven’t read it yet it’s possibly the best book on habits I’ve ever seen. I listened to it on the audiobook version which was really well… Sometimes the author reading doesn’t work but he reads quite well and boy yeah, just really breaks down a simply well-researched book but in a really simple way about how to establish habits, how to make them easy how to make it.

Yeah, remove friction from it, how to make it rewarding. It really breaks it down into concepts that you can recall back and make things easier to both establish habits and also break habits. So, I’d highly recommend that book.

Kai: Erik, how about you?

Erik: I’m going to go this week with my business’s payroll provider, which is pronounced Gusto G-U-S-T-O.com. For anyone that’s in the US, if you have to run payrolls, it’s a really good damn pretty service that takes care of the Federal, the State taxes, it really makes it worry-free. But the thing that made it so above and beyond for me is that over the last, I don’t know, a month at the time of recording with all of the stuff going on in the US with the cares Act, the paycheck Protection Program, all these Federal programs that are being rolled out.

The information that they’re providing, the reports, the way that they’re supporting you as a business that runs payrolls is just amazing. They’re giving you these great breakdowns of what all of this means for your business based on your revenues, your payroll, etc. It’s just amazing how they’re taking something that complex and really making it so you don’t have to do any research. It’s just there for you. So, it’s a hearty endorsement of that platform, gusto.com.

Kai: And Marg, what’s your pick for the week?

Marg: My pick this week’s going be a book as well. For a book I recommend Donald Miller’s Building a StoryBrand. I recently redid my website. I find that when it comes to other people, I’m usually good at picking up on their messaging, but it’s so hard to do your own messaging a lot of the time. Especially when you’re doing your site or redoing a service, messaging and clarity is so key, and that book has helped me immensely.

Like Meg was saying to I do love audiobooks, and I love them, especially when the author reads the audiobook. It makes a huge difference to me. There’s a different energy in it. So it is read by Donald Miller. He’s a great speaker. You can look him up as well, but I use that as a workbook. I feel my site’s gotten so much more clear. So if you’re going to read anything before you redo a site or service, if you haven’t read Building a StoryBrand, I highly recommend it.

Kai: Now that you’ve heard a bit about who we are and the Business of Freelancing, why should you tune in weekly and listen to us share our opinions and perspective? Well, because we’re all freelancers. We’re all indie consultants. We’ve had the ups and the downs when it comes to building and growing a business.

We’re excited to share with you our perspectives, our insights, and our conversations with interesting guests who will help you run a better business as a freelancer. Make sure you subscribe in your feed reader or podcast App of choice. Thank you, dear listener, and we’re excited to have you along on the ride.