Jason LengstorfExpert in location independence/work-life balance.
Bio

I've been working remotely for a decade, and making a living as a speaker, author, and consultant. I recently sold the digital agency I started in Portland, Oregon and started traveling permanently. I specialize in working remotely, helping freelancers grow their clientele, web marketing strategy, and becoming successful without making yourself miserable in the process. Business skills: inbound marketing, email marketing, content marketing, onboarding, UX, building systems and processes to automate tasks, managing work-life balance, optimizing productivity, digital strategy, freelance business development. Hard skills: JavaScript, Node.js, realtime interactivity and video (WebSockets/WebRTC/Socket.IO), static website generation, massively scalable sales pages via AWS (S3/CDN), PHP, heavy WordPress customization, CSS pre-/post-processors (Sass/LESS/PostCSS), HTML, workflow automation (Grunt/Gulp), workflow optimization across teams (Vagrant, process design, tooling), source management (Git). See how I think: https://lengstorf.com/blog/ See some of what I've worked on: https://github.com/jlengstorf



Recent Answers


When I was starting out freelancing, I was also starting in a new city without much of a network at all.

I built my network by looking at local meetups, conferences, mixers, and pretty much anything else I could find where people would show up who were either A) doing the kind of work I do, or B) were the kinds of people I wanted to work with.

I volunteered to give small sessions to help other people in my industry, which established me as a perceived authority. This led to referrals from people in the industry who were overbooked or had a lead they weren't sure how to handle.

I met as many people in my target client group as I could, helping for free (with advice and ideas only) in person, connecting them to other freelancers when it was appropriate, and generally being nice and helpful. This led to word-of-mouth referrals.

One note: this is a slower way to start. However, once I built momentum (this took me maybe a year, and I was working a full-time job in addition to networking), it's NEVER slowed down. I have never advertised or marketed myself, and I'm nearly always booked enough that I have to turn clients away. The agency I built and sold using this method is still referral-only and profitable, even after two years of new ownership.

Running ad campaigns can be effective, but it requires constant money and attention. Building a strong network requires a lot of upfront effort, but costs little and becomes less time-consuming as you become more successful.

I'm happy to talk more on this if you want to work on a specific action plan. Hit me up for a call and we'll hammer something out.


You can use WordPress as a REST API, which allows you to read/write data from WP in JSON format.

However, this won't be as performant as other database solutions, so you may want to consider alternatives unless there's a strong business reason to use WordPress.

I've built apps without WordPress, and also with WordPress as a back-end to meet a client's requirements, so I'd be happy to discuss the pros and cons with you if you'd like a second opinion.

Good luck!


Products like ZenDesk have a whole system built around help centers and tickets.

Discourse and Disqus offer forum-like discussions.

WordPress has several forum plugins.

And that's just what I can think of off the top of my head. My assumption would be that a deeper search on Google will come up with a metric fuckton of options. This is a huge challenge, so I imagine there are tons of companies trying to fill that space.

Good luck!


You may have some luck on Reddit's /r/freelance.

Another idea would be to hit local meetups for the web industry and talk to the people there. You'll get a sense for who's busy, and who you might be a good fit with.

Also, look at industry publications and see who's writing for them. These are typically very bright, very busy people. Try to become useful to them and you could end up getting an excellent education under their care.

The key is to remember that busy freelancers are always worried about wasting time, so you have to overcome the initial fear that it'll take longer to show you how to do something than for them to just do it themselves (and the subsequent fear that you won't stick around long enough to recoup the training costs). If you can empathize with that and come up with solutions and systems to PROVE that you will save them time, you'll get a lot further.

Good luck!


I've built Shopify sites in the past, and I can vouch for its flexibility as a platform.

That being said, Padraic is right that you most likely will need a developer to build the custom functionality you're after. It sounds like these are all easy enough to manage as categories and add-on products, though, so any half-decent Shopify developer should be able to handle it.

When it comes to platforms that let you customize — as Shopify does — the short answer to "is it possible?" is always, "yes." The qualifier there is whether or not it makes sense within your budget, and whether or not the proposed features will make a big enough impact on your revenue to justify the up-front expenses.

And, of course, the more customized the platform becomes, the more of a hassle and expense maintenance will be. So that's another factor to weigh when making a decision to go custom.

I've worked with hundreds of businesses who needed to strategize their online offerings in similar ways, so if you'd like a fresh set of eyes — whether that's to help outline the requirements for the software or to dig into the pros and cons of platform customization — I'd be happy to discuss. Let me know if you'd like to schedule a 15-minute call to discuss the problem and see if we'd be a good fit.

Good luck!


I'd recommend both. That's what I've done, and I've never hurt for work.

The thing is, many marketers offer lots of ideas, but are unable to implement the solutions. This means that a client has to hire a marketing consultant to create a plan, and THEN hire a designer/developer/etc. to actually implement that plan. This, to many clients, feels like paying twice.

Many of the people I've met will value development over marketing, and therefore cut corners on the marketing budget. This is bad news when you're a contractor who relies on other contractors or teams to build the things you offer as a service.

However, by building the skill set to not only design a marketing plan, but implement it as well, you're now able to market yourself as a 2-for-1 deal. As a freelancer, this is HUGE, because it creates a higher perceived value, and allows you to charge a higher rate. (They only need to hire you, vs. two separate contractors who will likely take longer overall to complete the job due to meetings, etc..)

Web development is the easier role to land early contracts. There are far more small projects for web dev; marketing tends to be a bit harder to break into (in my experience).

So for quickly building a stable income, start with web dev — but always continue learning. Every skill you add to your toolbox means one fewer contractor your clients need to hire, and that means happier clients, faster turnarounds, higher hourly rates, and a better overall experience for everyone involved.

I've been adding skills to my repertoire for over a decade now, and I bill my services as a one-man research and development team, because I can plan, design, develop, market, test, and manage a new business idea on my own. It took a lot of work to get here, but I'm now able to effectively write my own ticket because I can offer so much value and experience to my clients.

I'd be happy to discuss specific strategies if you'd like to put together a career development plan. I coach several entrepreneurs, and I think I'd be able to help you hit the ground running. Let me know if you'd like to schedule a short call.

Good luck!


The route I'd take is to start researching conferences that you'd like to speak at.

Find out where and when they occur. Look for a "call for proposals" — lots of conferences ask speakers to submit talk ideas.

Find out who runs them. See if you have any mutual friends. If not, see if you can find a way to be helpful to them (without asking for anything in return). Building good will has paid me back many, MANY times over as a speaker.

Look for local meetups. Maybe organize your own. Start to get experience as a speaker and build a reputation.

It starts slow, but things ramp up quickly once momentum picks up. I used this approach to build my own speaking career.

I'd be happy to share my strategy and story with you if you're interested.

Good luck!


One idea that's worked well for my clients has been to create a Skunk Works, which is effectively an autonomous, outside-the-bureaucracy, kinda-sorta-secret R&D team.

I've been on these teams before, and if they're truly left alone with a pile of ideas and resources, they can accomplish incredible things. (This is how Lockheed Martin developed some of its most incredible tech, and how Google takes its "moon shots".)

But it will be a challenge to management, because they'll have to stay out of it after the initial specs are delivered. If you can get buy-in, though, you'll bring back startup-level development speeds to your organization.

I'd be happy to discuss some of the processes I've followed and the structure of the teams I've been part of — just drop me a line.

Good luck!


If you're talking in terms of service-based work (freelancing, consulting, etc.), then ALL of sales should be based around the value you're creating for the client.

If I build a new marketing funnel for a client and they see an extra 100 leads per month — assuming their standard conversion rate for new leads of 5% and an average lifetime value of $6,000 per new customer — I've just created a pipeline that will feed this company $30,000/month of new revenue in perpetuity.

Even if that work seems easy for me, I need to be charging on the value I create. I've coached many freelancers who struggle with the idea of charging for their work, and it's always because they're framing it on hours or difficulty rather than value.

But if you sell on created value, your fees are essentially an afterthought: the client knows what they stand to gain, and paying you 20% of their first few months' revenue is a steal in their minds.

If you'd like to talk specific strategies for sales, I'm happy to share what's worked for me. Drop me a line.

Good luck!


I think it would be vital to the company's survival that roles and responsibilities are clearly defined. If there's grey area, I've found that work tends to gravitate toward the more motivated party, and the social/power structure gets weird.

I started a company with four founders, and we didn't define roles. What ended up happening is one person didn't do anything that wasn't interesting to them, one person would start a bunch of tasks and leave them half-finished for someone else to handle, and one person was only capable of handling process-based work, which left the fourth person (me) to handle everything else (and write the processes).

It bred resentment and made it very difficult to adjust roles going forward, because it had been established that I could do everything and therefore I became the final point of responsibility, even if we'd defined new roles later. Our only way out was to sell the company.

In later companies, I laid out responsibilities clearly and made sure each founder had ultimate responsibility and autonomy around their tasks. This has worked out FAR better in every case.

I've built a framework that I use for defining and divvying up tasks, and it's made a huge difference. I've had my coaching clients use it as well to similar results.

If you need a fresh set of eyes on it, or if you'd like to bounce ideas, I'd be happy to talk. Drop me a request and we'll talk.

Good luck!


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