Going from freelancers to business leaders

Not long ago, Charlie Fogarty and Sam Wilcoxon were both freelancers. They worked their own hours, where they wanted, and for who they wanted. Now they lead Lorem Technologies, a start-up based in New York City's fast-growing tech scene. We talked with Charlie about his transition from globe-trotting freelancer to innovative leader.

How did you get your start as freelancers?

My co-founder Sam and I both worked full-time jobs, and wanted more autonomy in our schedules. We took the plunge and started working for ourselves. He's a developer and I'm a designer.

I think some people have a romantic idea of freelancing – that it gives you a lot of freedom. Would you agree?

Yes. In a way it does, at least as far as when and where you work. But you have to do everything when you're a freelancer. You have to sell yourself and your work. You have to handle invoicing and accounting. You have to keep clients happy and well-informed. And this is before you even do any of the work that clients actually pay for. Maybe 30 to 50 per cent of your time is billable. You get used to leading an Army of One every day.

As a freelancer, you focus on building yourself as a professional. In a lot of ways, you put yourself first. This is the opposite of leading a team as co-founders. As entrepreneurs, it's all about the company. I would say the difficulties we encountered flying solo is what led us to Lorem.

So you started Lorem together once you started as freelancers?

Not right away. We both enjoyed the freelance life for a while. Then we realised that we wanted to start a business together. Neither of us was certain which direction the business should take though.

We made a lot of mistakes figuring that out! We spent seven months making a website creation platform that, we soon discovered, no one desperately needed. It was a heartbreak to throw away all our work. I think one of the central roles of an entrepreneurial leader is to know when to 'kill your darlings' – when to walk away from something that seems cool but has no future.

By that point we were nearly out of money.

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So then what did you do?

I looked through over 100 customer interviews that we had from our time working together. What was common between them? Of course, the best idea had been under our nose the whole time.

Both Sam’s parents and mine are small business owners. Even though they have employees, they're more like freelancers than your typical start-up. They often have to do it all themselves. We saw our parents spending hours every week struggling with fixes to their website and running their business online. With the help of an experienced developer, the problem could be solved in 30 minutes. We also had our own frustrations as freelancers: spending so much time dealing with processes and finding customers that we couldn't focus on design and development.

Lorem solves both of those problems. It connects freelancers with customers without the hassle. And it solves the problems of small and medium-sized businesses quickly and affordably.

So it's like a Fiverr.com or Freelancer.com?

A little. Services like Fiverr and Freelancer are great, but there can be friction.

You'll often have to write a creative brief, go through a bunch of bids, and screen a ton of profiles. Not to mention, it's another platform that you need to understand and deal with. Quality is a big problem on these platforms, and freelancers have a big incentive to up-sell you bigger projects.

It makes everyone's experience worse. Since it takes so long for the freelancer to secure your business, they would rather sell you a new website or an elaborate redesign rather than just fixing one little problem.

What we've done with Lorem is to make the process as instant and frictionless as possible. It's better for site owners and for the freelancers.

Everything takes places inside the DIY tool you’re using. There is no fancy platform, no extra accounts and passwords to worry about. You click a button, and in under a minute a vetted freelancer appears and talks to you about the details of the work. The freelancer can check out your site and give you a quote right then. For simpler jobs, we can often complete the work before the conversation is over.

The whole point is to get people focused on what they're good at. In the case of an SMB that's selling cookies or jewellery or offering nutrition advice or yoga classes. It definitely isn't fussing with the design of their newsletter sign-up form. And the designer and the developer should fix bugs or design sites, not stress about creative briefs and invoices.

Some people think that leadership is in your blood. And there might be some truth to that. Certain personalities seem to lead with less effort than others.

The issue of focus is a big one in leadership. For example, YCombinator’s Paul Graham has written a lot about how important focus is to a start-up. Do you agree?

Yes, focus is everything. I don't just mean in the product. Focus has been a cornerstone of how we've grown as co-founders. A start-up is nothing without focus.

Your team must focus. Our product helps people focus. And you, the entrepreneur, must focus.

We learned this the hard way. Early on, we supported tons of different platforms: Shopify, Wix etc. We'll support them eventually.

But we had to ask ourselves: do we want to offer a middle-of-the-road experience on 20 platforms of an absolutely superior experience on two? So we cut our focus down to Squarespace and Wordpress. All our resources and efforts focus on doing that one thing well.

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Lorem went through Techstars. What role has being VC-funded played in your growth as leaders?

Things started to move quickly after we settled on Lorem. After our seven-months-in-the-making failure, we built our product prototype in one day. We had one sale per day for several days in a row. We knew we were onto something and went all-in.

Techstars truly helped us grow as founders. It was during this three-month accelerator that we stopped being freelancers and started thinking like a company. We're so grateful for the support of the Techstars community over the last year of Lorem's development.

Some people think that leadership is in your blood. And there might be some truth to that. Certain personalities seem to lead with less effort than others. But there's also so much about leadership that you can learn with reading and mentorship. We have great mentors through Techstars and our investors. We value and listen to their advice because they've run the gauntlet of being a leader before.

There's also books. I love "The Hard Thing About Hard Things" by Ben Horowitz. A big point in Hard Things is feedback. Should you do a monthly performance review? Do we have some sort of form that managers fill out? I think Horowitz is right: humans are feedback machines. You can't wait for a month. You need to be offering constant feedback, always, all the time, and in every format that you can. That's how to sharpen your team.

There's certainly no replacement for experience.

Let's talk a bit about teams. There are many different philosophies for team building. What's yours?

As Lorem started to take off, we had to decide how to build a team: Who are we? Who do we spend money on? How do we work together?

As a freelancer I used to work where I want, when I want. My co-founder Sam did as well. Now we must be there at the right place at the right time. 20-something people are holding me accountable every day. I think a lot of people underestimate how much your team forges you as a leader. It goes both ways. A good leader sharpens the team, but a good team makes you a better leader by demanding so much of you and keeping you accountable.

I really believe in transparency in teams. I want everyone on the team to know what we're doing, why we're doing it, and how well we're doing. If we're doing well or poorly, everyone needs to know.

I've had jobs in the past where management submerged both the good and bad. Especially the bad. This doesn't help anyone. Besides, a smart team can always sense that something is wrong, even if you try to hide it. And you want a smart team, right?

Good people allow you be transparent. A good team can handle the ups and downs – but only if you, as their leader, help build a shared pool of understanding.

Leadership is often associated with age. Both of you are in your twenties. Do you think your age is a liability?

There's certainly no replacement for experience. And we have not had the same experience as someone who's been in business for 20-plus years. But there's also big benefits to being a young leader.

First of all, we have to earn respect from our team. We can't rely on people who 'respect their elders' for no other reason than age.

Some of our employees are older than we are. This makes Lorem much more transparent, which is crucial in an early-stage start-up. We expect everyone to speak candidly and clearly about the business, regardless of whether they're younger or older than us. This can be hard to sustain when you have a superior/elder relationship between you and your employees.

Second, our remote team is three to four times larger than what we have in the office. Plenty of seasoned leaders manage remote workers, but I think there's something deep in our experience as Millennials that makes our distributed team a natural fit.

We’re learning every day.

This is a guest blog and may not represent the views of Virgin.com. Please see virgin.com/terms for more details.

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