Student Success Spotlight with Jim Van Fleet

By Jim Van Fleet

Today’s student success spotlight is with Jim Van Fleet. It’s our hope that we’re able to share a different story each week of how a past student has been able to significantly grow their freelance business by applying the concepts they learned from Double Your Freelancing (check out last week’s with Matt Olpinski). If you feel your story would be a good fit, share why!

I’m making more, working less and with better clients. I expect to double my take-home this year!

What more can someone ask for? This was Jim’s response when we asked him how his business has changed since being exposed to the DYF products and courses.

He’s done his homework to get to this point though – in fact, he’s tried it all: DYFR, DYFC (formerly the Blueprint), the Masterclass, the Freelancers Guild and Planscope.


But, we’re here to learn about Jim Van Fleet and his business, itsbspoke. Take it away Jim!

What type of business do you run?

I’m a freelance back-end developer that’s currently transitioning to running a three person development and design agency.

How long have you been in business?

I began freelancing in February 2010, but I took close to a two year hiatus to be the CTO of a mobile gaming company that ultimately raised a Series A round. As that company wound down, my CEO sent me a link to Patrick McKenzie’s post on being very successful in software consulting, along with a challenge to walk that path myself.

That post of Patrick’s contained, in turn, a link to some of Brennan’s work, and We Are Titans was familiar to me from my time in Richmond, VA. Now, I’m “freelance” to stay, and have two full-time employees.

What initially got you into freelancing? Was it what you expected?

I moved to Charlotte, NC to take my first full-time job as lead engineer on a Ruby on Rails project. I grew that userbase from 2k to 150k, led a contracting team, ran operations, business analysis, sat in meetings, did support, the whole kitchen sink. It was extremely fulfilling, but I burnt out. It took me six months to quit. I’m still not sure if they replaced me with two or three people when I left.

After that, I freelanced, taking jobs that would help me learn to be a better engineer. I wanted to be able to be a better support for the founding teams I’d work with. I had no intention of growing the company, being fully aware of the difficulties inherent in starting a company because you are skilled at what the company does; those are much different skill-sets.

It was what I expected – massive cashflow swings and all. What I didn’t expect was to find that the last 20% of my time and effort that I spent on being the best engineer I could be was wasted. I wish I could have that time back, and been more confident in using (and developing) my other skills and knowledge about business to better serve my clients.

What’s been most challenging thus far?

Overcoming the mental limits involved in making sales. It’s hard to unlearn the relationship between effort and value, especially when many otherwise desirable clients prefer this arrangement. I historically have held myself to higher standards than others, and undercut myself to appear humble and likable. It’s possible to be both of those things without the self-condemnation.

I am also a people pleaser and have historically been reticent to qualify candidates. There’s so much bad tech and bad service out there, and I wanted to make sure they got good service even if it wasn’t from me. In reality, that is not my responsibility. My responsibility is to provide the best service I can for my clients, and I can create a life I actually want for myself instead of anxious overwork through proper qualification.

Finally, I believe myself capable of helping with a wide array of problems, so it’s been a challenge to explain clearly what I do and for whom to my audience. I still struggle with this, but I am beginning to get it right.

Did you ever want to quit or give up? 

The cash flow swings are very stressful. I’ve had calendar months with no revenue whatsoever, with bodies on the payroll.  Other times I find myself faced with a technology problem that I know without a doubt I can solve and that has marginal value to the company, versus a marketing or sales task that I know is important, but I might not get right.

Figuring out how to best allocate my time is a constant challenge for me. As an engineer, I am accustomed to dealing with the stress of multiple demands on time with prioritization and a drive towards completion. As a business owner, many tasks are never ever complete, and you’re constantly adapting.

Sure I wish it were simpler. I’ve made major mistakes judging client’s budgets; that feels particularly bad since that’s going to impact my own family. But if you give yourself a little freedom from fear of failing and fear of not having enough money, you’ll have a chance to learn in a way that works forever. We can read Brennan and others all we like, but there’s nothing like the experience you earn yourself.

What were you struggling the most with when you ran into DYF?

For all of the time I had spent learning what makes initiatives successful, and how businesses manage and grow, I certainly didn’t spend very much time talking about it, or truly leveraging that knowledge into increased responsibilities in my full-time jobs.

Once, I had a model for human behavior that suggested if your boss came to regard you as an overachiever, reliable and almost certainly right – that on its own would yield increased influence. This model turns out, in my experience, to have no basis in fact. Performance in your role, even excellent performance, is not guaranteed to do anything except keep you in that job. If you use your wits, you can probably get a better job next time.

My main problem was that there was no additional “better job” in technology for me, at a certain point. I had to go and make my own, and Brennan’s work has been instrumental in that.

What are some big successes you’ve had recently? Did you do anything differently?

I am wrapping up my first project where I was really able to put DYF lessons into practice. The entire conversation was about client needs and results, not on what effort it would be on my side. When the client balked on price, I was able to sell him on reducing scope and getting him to prepay in full!

I expect to net low five figures for managing a freelancer and running the client meeting on a weekly basis, and for little bits and pieces of my time spread here and there. That’s allowed me to hire someone I’ve long wanted to get onto my team to expand what we can offer.

It’s not just the 300% increase in my rate on a time basis; it’s that the freedom and satisfaction with my work and my performance is through the roof.

What I did differently was I valued myself and my skills more, and felt the courage to talk about what I do that’s special – and why what I do is worth a premium price. (In this case, the client had no idea what premium pricing was or wasn’t anyway).

What are some specific tactics, strategies, or pieces of advice that have really helped you grow?

Sales is critical, and you have to understand how to perform that role in a healthy way. I used to think I was a bad negotiator, because every time I had a job negotiation or major client negotiation, I essentially let them dictate terms. As it turns out, I have a lot of the skills of an excellent negotiator (listening empathetically and effectively, honesty, creativity) – my problem was that I never had any alternative to the deal.

Don’t feel like you have to have everything figured out before you totally revamp everything you say about what you do. Talk about the transitions you and your firm are making honestly. Talk about what work you do now versus what you would like to do. But do ALL of that after listening and listening, and listening again. I myself have a variety of ways to deliver value to a person I meet, and there’s no substitute for truly caring.

Think to yourself, how many people do I know in my life that try to take definable problems and pain I am experiencing, and to solve them completely? Not many, right? And you’d be thrilled to talk to that person, right? If you are genuinely trying to solve their problems, this is not “yucky” sales that is exploiting people.

Remember, most tech projects and vendors suck – lots of people would love to trade the money they have for projects that eliminated pain (or, better still, created more sales for themselves). If you’ve listened to someone and really cared, you might be able to introduce them to someone later. Making introductions for other people is a great way to end up creating a great reputation.

Qualifying leads is critical. I can’t believe the impact on my sales conversations that even a single-item drip autoresponder has generated. The tenor and content of that initial conversation in person has changed utterly. It’s no longer about my portfolio, it’s about their needs and project. I am excited to incorporate what I’ve learned into the second round of telling my agency’s stories on our own site, but we’ve got plenty of proposals and work to do first!

What are you most excited about for your business in 2015?

For the first time in a long time, I don’t know what’s going to happen with me this year. I know how I intend to proceed, I know who I’ll be inviting along with me, and I know where I’d like to go, but I’m okay with not controlling the outcome.

One of the most truly touching experiences in my life was during the last year, as I had all client relationships and sales work in good standing, just putting my phone away and playing trains and solving puzzles with my oldest son. I felt a real grace that I haven’t felt a lot as an adult.

Plenty of times, I would have been obsessing about the next ten things I needed to do for my next volunteer engagement. I was never present. I am really looking forward to being more present in 2015, and building something meaningful that helps people have great careers in technology.

jvf-headshotIn addition to being a leader of the software development community in Charlotte, Jim Van Fleet is President and founder of it’s bspoke, a boutique software consultancy. His monthly startup newsletter has reached over one thousand subscribers. He has been programming computers professionally for over 15 years and has degrees in Computer Science and Managerial Studies from Rice University. He currently serves as Brigade Captain for Code for Charlotte.