Corporate Dropout turned Independent Tech Consultant & CTO @ The Domino Project: Meet Willie Jackson

Marlee: Willie, thank you so much for taking the time to talk to me today and share your story with the Metamorphoself readers.

Willie:  Sure.

Marlee: So I want to start today’s interview with a classic corporate America interview question.

Willie:  Sure.

Marlee: Ok. So, why don’t you tell us a little bit about yourself Willie?

Willie:  Oh my goodness.  Okay.  Where do I start?  Okay, I am a corporate dropout.  That’s what I call myself, full-time freelance troublemaker currently working on the Domino Project up here in New York with Seth Godin, and five other amazing humans trying to reinvent what it means to publish books in the modern economic environment.  I worked as an IT consultant for three years, and somehow made my way here after much misery and weeping and gnashing of teeth and escaped the corporate beast, and I’m on my own full time now.

Marlee: That’s awesome.  So why don’t you tell us a little bit about your business. That is, what you did in your business that you started when you went out on your own and who you served in that business.

Willie:  Sure.  So freelance web design, development, hosting, optimization, marketing, the whole – let me just run down a list of things that I do.  Basically I help business, I help businesses do well online, succeed online.  That could be selling a product.  That could be promoting personal services, all sorts of things.  My typical client is either professional or small business.  I work with some schools, anybody who has a clearly defined need and that I can help them meet their needs online, you know, we’ll take it on.

Marlee: Excellent.  Excellent.  Okay, so you say that you transitioned from corporate prisoner, or you’re a corporate dropout, to an entrepreneur.  But you’ve also said that you always wanted to pursue entrepreneurship.

Willie:  That’s right.

Marlee: You just didn’t know what you wanted to pursue, and it think a lot of people are in that place.  And so my question to you is, what did you do or what process did you go through to decide what kind of business to start?

Willie:  Oh boy.  Yeah, I knew since college that I wanted to own my own business, but it was mainly an issue of freedom for me.  I wanted to be able to go where I wanted, when I wanted, and do what I wanted on my own terms.  And I didn’t really know where to start. I didn’t have any sense for what my options were.  I didn’t have any clearly defined skill sets that said okay you should, you know, be a network engineer.  I didn’t have anything that lent itself to that.  So I did what most people did and got the best job I could, and it worked out for a little while but it was ultimately very, very unfulfilling.

A class project in 2005 required us to build personal web sites.  I was an IT major, and something just clicked in me.  I saw it as such a fantastic vehicle for marketing myself as a young professional.  So I just attacked it.  I used a free web site template, and I did my absolute best to put my best foot forward online, and everything kind of spiraled out of control at that point.  So I started building web sites as a result of that project.

Marlee: That’s really awesome.  So you didn’t really actually have any direct training in web site design?

Willie:  Oh no.

Marlee: You were all self-educated.

Willie:  Yeah.

Marlee: That is so cool.

Willie:  Yeah, everything I do for money now was self-taught.  My dad hates it when I say that.

Marlee: That’s incredible.  It makes you wonder exactly why we go to college huh?

Willie:  Well, that’s a different, that’s a different discussion all together.

Marlee: Right Okay, so what resources did you use then in terms of a practical perspective to know how to put a business together?

Willie:  Oh, what so – I mean the actual putting together a business is $100.00 and a form you fill out online of course.  As far as running a small business, handling the accounting pieces, and you know, tools to simplify your work flow and things like that, that just comes with practice.  You know if you run a web design operation, there are a lot of very specific tools that you can use to help with things like invoicing, time tracking, keeping track of your expenses, all sorts of things.

So it’s really niche specific, but I think it depends on your industry and also just being there long enough to ask around because somebody’s gonna have done it for longer than you have, and there are just so many resources available.  So it depends.  Generally speaking there are lots of tools like everybody can use like Fresh Books for invoicing, but some of the more specific ones that allow you, for example, web designers to create wire frames of web sites tos how the clients before the actual site is built out.  Those things are very niche specific, so it just depends.

Marlee: So you didn’t really use any one particular resource.  You kind of just –

Willie:  Oh no.

Marlee: – used Google as your best friend and –

Willie:  Wire and duct tape is how I patched up my operation for a, a long time.

Marlee: Excellent.  That’s good.  So you just got down and dirty.

Willie:  Sure.

Marlee: Okay, so here are some kinda “mental perspective” questions that I’m gonna shoot at you now, and that is you know when you first launched your business, what were you most of afraid of? And I wanna take you specifically to 2010 when you had completely cut yourself free from your corporate position.  So, what do you think you were afraid of the most once you launched your business?

Willie:  You know, I was, I was, fear was never a huge factor with me.  I’m, I’m unique.  I, I realize that.  I’m, I’m very unique in that I’m not precluded by fear in a way that a lot of my counterparts are.  So even though one of my biggest challenges was the fact that I purchased a big house in 2007, six months out of college which was probably not the smartest thing I’ve ever done, but bought a big house; single, no kids, so you can do the math on how much sense that makes.  And that was my biggest challenge because I had to meet my mortgage, and other than that, you know, I could have quit eons ago.

But, you know, I committed for 30 years of financial slavery, and I had to control that commitment.  So that was the biggest challenge in preparing to make the leap.  But as far as fear holding me back, I didn’t really have any fear.  I didn’t really have any fear of losing everything.  You know, I knew I was young, but I knew I could figure out anything I needed to.  I knew I could recover from anything financially, and I had really good people looking out for me.  So I was never precluded by fear in a sense that I needed to overcome that in order to make the move.  It was truly a logistical issue because I was traveling for 40 hours a month when I was on out‑of-town projects.

I was an IT consultant, and there is only so much work can you can do from a hotel after you get off work.  You know, you can only scale so far in my kind of work because during the day you might be able to address a few client emails and some emergencies or you have to step out.  But generally speaking, the bulk of the actual delivery of your work, the design or the development, that requires some time to plug in and not be doing anything else.  And typically those would be in the middle of the night, so, ’cause that’s how I’m wired, I’m almost nocturnal, but it doesn’t lend itself well to a day job.  So that was the biggest challenge for me.  It wasn’t an issue of fear.

Marlee: That’s actually – you are unique in that way, and that’s actually a really good point which is if you’re not held back by fear, you’re really unlimited in what you can do and can make yourself available to the opportunities and the resources.  So –

Willie:  Sure.

Marlee: – hey that works.  Okay, so what did you do to stay motivated when things got difficult or when you had feelings of doubt maybe let’s say –

Willie:  Oh boy.

Marlee: – about what you were doing?

Willie:  I never doubted myself in the sense that I could do it.  One of the general metrics I set for myself is that I knew if I could make it six months out, I could make it through the rest of my life and I would never have to go back.  And it wasn’t an issue of me hating the employment, it’s just that the standard 9:00 to 5:00 coming to work, that kind of thing, without the true freedom of creating things and breaking things, it was just killing the creative parts of me.

I appreciate things like the arts and, and science and poetry and I have a very wide range of things that interest me, but having a profession that requires a very narrowly focused skill set and you to fill a certain role, talk a certain way, dress a certain way, that really kills the creative spirit.  It did for me anyway, so I just was not wired to survive in that environment.  And it really feels like a slow death in retrospect.  So I just knew I had to be free of that.  I kinda rambled, so I don’t know if I answered the original question.

Marlee: Well I guess what you’re saying is like there was no turning back for you.  Your motivation was the fact that you couldn’t go back to that life.

Willie:  Yeah.  So, you know there were really difficult times in the journey where I knew I had to be free of that, but I just couldn’t get to the point where I was making enough to cover my bills, and there was that, how do you get past that hump, you know, do you –

Marlee: The dip.

Willie:  – yeah how do you get past the dip?  How do you push through that dip?

Marlee: Right.

Willie:  And, you know, there’s, of course now I’m a lot better at it, and I would say well double your prices, lose half your clients.  Make the same money and do half the work. So it’s –

Marlee: Right.

Willie:  – it’s simple from retrospect, but I just couldn’t fathom that time, ’cause you know, as freelancers we wrestle with the idea of feeling like we need to charge a certain amount, but not charging more this amount or not feeling like we can charge more, and can we charge people different things, like all these things that are like no‑brainers to me now, I didn’t have any answers at the time.

Marlee: Right.

Willie:  But fortunately I built up a great set of mentors who kind of helped me through some of the process.  And a lot of it really was just trying a few things and seeing what worked.

Marlee: Well that’s awesome ’cause you just set me up perfectly for my next question.

Willie:  Uh oh.

Marlee: Which was that, you know, you’re now working with Seth Godin and The Domino Project where Seth is challenging the way that books are published and ideas are spread.  And I wanted to know does that mean that you’re taking your foot off the burner in your own business, or are you managing things altogether now?

Willie:  You know amazingly, I’m actually doing more freelance work now than I was before, and I had a feeling this would happen, but because I have to focus so much on one specific thing during the day – you know we, we have a lot of freedom with our schedule.  There’s not a lot required of us in that sense, but you know, we do have to focus and we have to get the work done.  That’s the most important thing.  Seth asks us to make big promises and to keep them.  But you know you start saying yes to things, and you get better at doing them faster.  And like I can do things now in a couple hours that would take me a day or two just a few months ago, so I’m actually doing more freelance work now than I was before.  So I’m still very much freelancing, but yeah.

Marlee: That’s great.  And so being that you’re connected with like Seth Godin, and also –

Willie:  I love that you keep name dropping.  Keep going.

Marlee: – and no, well I’m about to name drop Pam Slim…

Willie:  Let’s do it.

Marlee: – the question that I have for you is how do you think that you managed to get on their radar, not that you were trying to get on their radar, but what do you think that you were doing that made you someone they would want to connect with?

Willie:  Yeah, somebody else asked me that question this week.  I got an email from a gentleman who saw something that was wrong on my web site (something that was technically wrong), so I fixed that.  And, you know, I thanked him, and he said one more question.  He said how is that you’ve gone from quitting your job to work for Seth Godin in less than a year? You know, what’s your secret?

And I laughed, I didn’t really think about it like that.  But I don’t think that there is any secret or special strategy that was employed.  You find this halo effect that takes place when you start getting connected with the right kind of people who have a genuinely positive perspective on life and business, ’cause you know in the entrepreneurial world, your business is kind of an extension of your perspective on life, just like Apple is an extension of Steve Jobs’ personality, and things like that.

It’s very obvious when personality driven companies exist.  And you know there was no better way to see this than in a freelancer’s operation.  So as I got hooked up with certain people who were, you know, aligned with my values for business, I started adopting some of them, saying okay I align with this.  I identify with this.  And as that network grows, you just start meeting people really, really rapidly.  And more good people come your way, and it’s uncanny, it’s crazy how fast this happened, but there really is no secret sauce here.  You do good work, you care about people, you try your hardest and repeat that until you die, and that’s kind of what I’m doing.

Marlee: I think I’d have to add also that you make yourself available.

Willie:  Sure.

Marlee: Because you and I connected over Twitter.

Willie:  Sure.

Marlee: And, you know, because I @ replied you something about, I think it was about gummi bears.

Willie:  Mm hmm.

Marlee: And then now here we are having an interview.  So –

Willie:  Yeah, a week later.

Marlee: Exactly so and –

Willie:  Sure.

Marlee: – putting yourself out there in that kind of regard, not being afraid to make a comment –

Willie:  Yeah, so from a, from a philosophical perspective, if you put yourself in a position to take advantage of opportunities, and you make yourself available, replied to emails quickly and just generally have a presence, people will find out, opportunities will find you, and you just find that the universe kind of conspires in your favor.  So absolutely, that’s a big part of it.

Marlee: I love that.  Okay, and so two last questions, and hopefully we’ll make it before our video cuts off, and that is –

Willie:  Okay.

Marlee: – I’m gonna combine them.  How do you think pursuing entrepreneurship has changed your life, aside from the obvious?  And if you could only give one piece of practical and immediately applicable advice to someone considering entrepreneurship, what would it be?

Willie: All right I’m gonna start with the second one first.  My advice would be to go now, go yesterday and go faster.  You have nothing to lose, everything to gain. Life is not gonna get any shorter and the freedom; experience on the other side is something that you really can’t put a price tag on it.  I know I can’t.  When I first quit my job, I took a dip in my income, but the upside of the freedom is just something that I could never ever put a price tag on, and I tell people jokingly I’d be a very expensive employee to buy out because my freedom has a huge price tag on it at that point.  And to your other question – what was the other question?

Marlee: The question is how has entrepreneurship changed your life?

Willie:  I don’t think it’s changed my life, I think it’s allowed me to be freer in who I am already.  So you know, I already had the mindset of entrepreneurship, and wanted to be a freelancer, take on projects and really explore how my personal values aligned with how a business is run, and how to be the owner of my successes and failures.  That was a big thing for me.  And I don’t think that it has changed me in a sense that I’m a new person now, but I’m much more in tune.

Like all the different areas of my existence are kind of aligning now, and it’s just like a beautiful intersection because when I can, when I’m free to be who I am, and attracting the kind of clients and friends and mentors that are befitting of someone who has a naturally positive perspective, things just kind of line up.  And, you know, it’s kind of a touchy-feely answer, but I don’t think it’s changed me.  I think it’s allowed me more freedom to be who I am, and it’s just a great thing to experience.

Marlee: Wow, you’re incredible Willie.  Thank you so much.  We made it in 14 minutes and 45 seconds.

Willie:  Sweet.

Marlee: So this will probably be, be cut off.

Marlee: But I just wanna thank you so much for your time, and it was a –

Willie:  My pleasure.  Thank you so much for **** –

Marlee: – pleasure getting to talk to you again today.  And I look forward to connecting with you again.

Willie:  Yeah, let’s do it.  This was fun.

Marlee: All right.  Take care Willie.  Thanks.

Willie:  Thanks.

Marlee: Bye-bye.