How A Non-Technical Entrepreneur Used Freelancing To Launch A Tech Startup (And Three Hard Lessons Learned)

Damn.

What a year.

2015 is gone and I’ve learned more in the last 12 months than I could have imagined. It was a year filled with both a combination of amazing highs (wedding, honeymoon, launching 2 products, writing a book) and some ridiculous lows (ie. injuries, stress, wasted $$$, waste time).

This visual from Derek Halpern sums it up well:

Over the last three years, I’ve run a freelance business focused on helping startups and brands navigate the world of content marketing. I’ve helped everything from Fortune 500 companies to startups making the headlines of TechCrunch. And while I love helping brands and other entrepreneurs — I’ve always had the itch to start my own and take the lessons I‘ve learned along the way to create something great.

This year I was able to take action.

It’s a known fact that having access to capital is one of the biggest challenges for starting a business — especially a startup.

The idea of a friends and family round has always been a foreign concept to me. I didn’t grow up with aunts or uncles working in the c-suite and would struggle with the idea of taking capital from my family. Lots of my colleagues and peers have taken this approach when they had nothing more than an idea, I think that’s great. But for me, I didn’t see it as an option.

But I did see making money online and consulting as a way to make cash the hard way and eventually start building my dream.

So I doubled down on something I knew well:

The Hustle.

I knew how to sell my services and I knew how to deliver for clients.

So I focused on building a freelance business and selling a variety of information products like my books Stand Out or The Hustle Manifesto online. In addition to not having access to immediate capital, I liked the idea of demonstrating traction before seeking out capital so I building the product before knocking on doors was important to me.

I considered freelancing to be my own personal seed round and while it took a lot more time than the traditional approach, it eventually worked.

Disclaimer:

If you can get the capital early— do it. I talk about this later but time is king and not having to break up your time between product and service can be a competitive advantage.

I used consulting as a launching pad.

Focusing on servicing tech startups allowed me to connect with founders who could teach me about the role while I taught them about marketing.

I then applied that knowledge to launching Crate + Hustle & Grind.

As a non-technical person, capital is even more important because I could only do so much as it relates to product development. Sure, I could get by hacking a few things together myself but one thing I know is that I don’t know everything. Which is why I knew to make this happen, I would need to bring in people who could execute. So I did I exactly that and today have a team that inspires me daily, challenges me constantly and is commited to creating something worthwhile.

But let’s take it back to the beginning…

Step 1: Building A Consultancy From Scratch

As a freelancer, you’re only as good as your last project.

When I first started in the marketing world, I didn’t have any experience because I was fresh out of school. I couldn’t get a job because I didn’t have experience so I decided to start my own agency at the tender age of 23 years old. In these early days of consulting, I said yes to every and any project that came across my desk. I was young, hungry and had no portfolio.

Saying yes to these projects allowed me to build a mediocre portfolio along with a handful of case studies and references that I could use to help land my first agency gig. I was hired as a digital strategist and was able to get the gig by writing about marketing and building a small business. My time at the agency allowed me to learn everything I needed to eventually make an escape and run my own business on my own terms.

As a freelancer, the majority of your work will come from referrals and through word of mouth on the back of clients, friends, colleagues and acquaintances It’s important to make an effort to develop and nurture relationships with people in industries and organizations that would be interested in your services before you need them.

Create a newsletter.
Attend industry events.
Curate content they would find useful.
Join community groups & associations.
Write blog posts that their industry would share.
Send emails when you found articles that would be of interest.

In a nutshell: Hustle.

This is blog post goes in much more about how I built my consultancy:

Once I had succeeded in bringing in enough capital to launch something new, I set my target on launching two new projects: Hustle & Grind + Crate. In this post, my focus is going to be on Crate, a tool that helps people find articles and links that worth sharing on social media.

And here’s how it all began…

Step 2: Build A Prototype Using Invision + PhotoShop (Even If It’s Ugly)

This is what I’d consider Crate 1.0.

It was nothing more than an idea that there were gaps in the world of content marketing and they needed to be filled.

I came to the realization that this was something that needed to be built after spending hours working with clients on their content marketing efforts without tools that could make life easier.

Why did I have to spend hours looking for relevant content? 
Why did I have to use a bunch of different tools for gathering data? 
Why was I sharing blog posts via Google docs then uploading to WordPress? 
Why is every startup using different content scheduling tools?

There had to be a better way.

So one late night, I designed what I thought this platform would look like and I uploaded a handful of these designs to InvisionApp. This allowed me to give faux-demos to people in the community and let them know what I was working on.

The Goal: Build something that can be used to communicate the vision.

Step 3: Show The Faux Product To Gain Insight

I shared the idea surrounding a full Content Marketing Suite with anyone that would listen. One evening, I shared it with a client — the founders of a local ad agency and they quickly understood and loved the idea.

We negotiated a deal in which they’d help in the design of the Crate identity and help take my wireframes to the next level. And that’s what they did.

Now I had something that actually felt like a product that was live and able to be used. I took the various designs that they had created and uploaded them to Invision. From there, I had something to ‘demo’ for gathering feedback and insights around what we saw as the future of Crate.

The Goal: Build a prototype that can be used to give faux demos.

Step 4: Use Clients For Customer Research

When I was in University, I took my first stab at a product without much customer research or investigation. The product flopped and I learned a valuable lesson around the importance of customer development and research. For Crate, we knew that we had the problem worth solving but what we didn’t realize that we didn’t have focus.

Luckily, the majority of my freelance clients would also be Crate customers and speaking with them shed light on the real opportunity. Our target audience is marketers who understood the value of content marketing.After chatting with clients, peers, and folks in the industry — we decided to focus on the biggest challenge in the world of content marketing: TIME.

One of the marketing tasks I’ve been constantly asked to implement for clients has been the act of ongoing content curation for newsletters and social media. I spent hours digging through industry journals, niche blogs, industry blogs, influencers accounts and newsletters to find content for a variety of different industries ranging from sales to healthcare. Through a combination of discussions, interviews and research — it was obvious that the process for content curation was quite broken.

At the time, the number one content curation tool was Buffer Suggestions. A feature within the popular social media tool Buffer which delivered content suggestions on topics like marketing, productivity and entrepreneurship. Our discussions with marketers uncovered that people were struggling with Buffer Suggestions for a couple reasons:

1. The content suggestions were the same for too many people. Because everything was coming from the same pool of content suggestions it led to lots of sharing of the exact same posts.
2. The content suggestions were not personalized to your actual interests. If you were interested in sharing content about fitness, you wouldn’t find that content in your Buffer suggestions.

When I saw my friend Kiki write a blog post that confirmed that Buffers auto content worked but that there were some hesitations around it:

I knew we were onto something…

But when Buffer retired suggestions for some of the reasons that we saw as issues with the product — it clicked that we needed to double down our focus on creating a tool for identifying content worth sharing rather than trying to build a full content marketing suite.

Goal: Understand the problem you’re solving.

Step 5: Find The Right Partner By Any Means Necessary (Speaking, Forums, Angellist, etc)

If you’re a consultant or freelancer in general, public speaking can be one of the most lucrative marketing activities you can take part in. I like to find events that aren’t filled with people like me (ie. content marketers) but once in a while, I attend industry events. Over the last few years, I’ve built plenty of relationships from speaking, MCing or sitting on a panel at an event. Many of these relationships have led to new work and opportunities.

Early last year, while working on the early stages of Crate, I threw out some hints around the fact that this was something I was working on. To my surprise, after the event I had about 3 different people approach me with interest in the idea. One of them ended up helping build the first working prototype of Crate which led us to finally having a working product.I sent it to 100 or so of my peers, clients and marketing friends to gain more insight and feedback on what we built. The feedback was straight forward:

You guys are close. I love the idea but it’s still pretty rough around the edges and there are lots of bugs.

It was time to start building a team that could take this to the next level.

I put up a job posting on Angellist and a handful of other sites to seek out a developer who would be able to jump in on a contract. Within a week of putting up a posting, I recieved applications from people all over the world. I would be using the revenue from my consulting business to cover the cost of bringing on two developers for five months.

David stood out as he was willing to get his hands dirty immediately. Within a couple hours, he was able to understand the problem and make changes that would make the product more reliable and usable. Over the course of five months, we clicked on our philosophies, obsession with Gifs and vision for the company. His 20+ years experience in tech was valuable in understanding what it took to create a user focused product and after a few months of working together, it became obvious that he was CTO material.

Today, Crate is live and people are using it from all over the world:

Check it out: GetCrate.co

Three Lessons From Funding A Product Through Freelancing/Consulting

Here are the three biggest lessons I’ve learned over time:

Time away from the product will hurt the product

It’s a hard pill to swallow but not being focused solely on the product will hurt the product. There are only so many hours in a day and if the competition is full time while you’re part-time, you’re giving them a better chance of winning. Sure, you can sacrifice late nights and early mornings but this approach to the grind can result in burn out and fatigue.

You have to say no more than you once did

As a consultant, I jumped on new business opportunities and said yes when people wanted to chat shop and pick my brain. When you have multiple businesses, it’s rarely a good choice to jump on a call to chat about a ‘potential opportunity’ or grab a ‘coffee’ with someone without due diligence. Look, I love people. I love helping people. But with limited time, it’s more important than ever to say no and focus on execution.

As Ev put it in his formula for success:

Say no to most things: Features. People. Partnerships. “Coffees.” Projects. Only a few of them really matter. (Yes, it’s hard to know which.) Don’t get distracted.

There will be sacrifices and they will hurt

From the gym to time with friends and family — the sacrifices were real. Don’t get me wrong, I was able to get away for a little under 3 weeks to check out for my honeymoon but the weeks leading up to that break were filled with 70 hour work weeks.

The ongoing management of Hustle & Grind, Crate and Foundation (my consulting biz) has easily been hardest thing I’ve ever done in my life.

Late nights. Early mornings. Constant 🔥’s to put out.

But I love it.

I’ve always loved building things. I’ve always loved creating value and arming people with tools that make their lives easier and better. If the year of 2015 could be summed up in one word it would be: Hustle.

But I’ve learned that hustling without focus can hold you back.

Which is why I’m aiming to make 2016 the year of focus.

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