Bootstrapping a 24/7 On-Demand Technical Expertise Marketplace for Online Tools, Lorem Co-Founder Interview with Charlie Fogarty

In this article, we speak to the Co-founder of Lorem, Charlie Fogarty. Lorem is a New York based startup which connects website owners to the best freelance developers and designers on the web. They offer 24/7 on-demand access to a network of hand-vetted experts. Lorem recently graduated from the Techstars Boston accelerator. Its seed funding was led by Flybridge, with participation from Founder Collective and angel investors, including Constant Contact founder Randy Parker and Frederick Townes, creator of the W3 Total Cache plug-in for WordPress.

Key Stats

  • Date Started: Founded in December 2017 (1.5 years old)
  • Location / Homebase: New York, NY
  • Number of Employees: 6 Full Time and an army of contract Lorem Experts

Give us some backstory. What inspired your company?

Both Sam and I have entrepreneurial parents. Week after week, we would hear them anguish over their website or some aspect of their business online. My family business used to email an excel spreadsheet to a developer who would make the updates two-three weeks later!

At the same time, he and I would do freelance design and development. We experienced the classic “bidding” marketplace and the feast or famine that so many freelancers experience.

We knew how hungry we were for web development and design projects, and at the same time how frustrated business owners were with the state of their website. Something just didn’t add up, and we were immediately determined to find a better way.

How did you validate the idea?

At first, we thought it was a tooling problem. If only business owners had website software that was easier and smarter, their problems would be solved. Wrong. We spent 6 months trying to build a ‘better’ Squarespace/Shopify/etc. It was a great design challenge and we wrote some awesome code to automate some of the annoying parts away.

We tried to sell it to dozens of people but got the same feedback every single time – “yeah this is pretty cool, but can’t you just do xyz for me? I’m super busy”

After we got over the emotional trauma of building something no one wanted, we realized that it was never a tooling problem – Squarespace, Shopify, WordPress, and hundreds of other DIY tools are really good and already used by 30M+ people. It was, in fact, an “access to people” problem.

We interviewed over 100 website owners to try to figure out what they really wanted and why it wasn’t being supplied today. The next hypothesis: business owners want to click a button and have a talented, trusted, affordable techie person show up to solve their problem.

In a weekend, Sam and I built a prototype. It was a customer support chat tool, jerry-rigged into a WordPress plugin and running on (all tech startups should be using Glitch but that’s another story). We pitched it to an interior designer and got our first sale. The next day we got another, and the next day another.

The only expert in the marketplace was Sam. Here’s how we thought about validating the idea (and how we still think about many things at Lorem): follow demand and test any hypothesis as quickly as you can.

During the launch phase, did you maintain a full-time job? (or even currently)

For about two years, Sam and I worked full-time jobs while doing projects nights and weekends. We had a google doc full of problems and gripes. We’d pick one, ideate a solution, build it in a weekend, and then kill it as quickly as possible. We quit our jobs when our obsession with this problem really took shape.

Can you describe your business model and how you feel it works?

Essentially Ask Lorem is a marketplace. We provide on-demand technical expertise for Squarespace, MailChimp, and lots of other online tools used by entrepreneurs.

Put in a request, get matched to the right person for the job in a few minutes, and they give you a free quote for anything ranging from $10 to a website redesign. We have also done the work of finding and vetting wonderful developers/designers/techie people so you don’t have to worry if the person you’re working with is trustworthy, quality, or capable.

The core model: Lorem is free to use for clients – you just pay per project, and we charge a fair fee to the expert for work completed.

We also have a higher tier for clients who want a Lorem Expert proactively looking after their website and online goals – like an account manager.

Did you do any email marketing/outreach?

Of course. Sending thoughtful, personal cold email is how we acquired our first users. It lets you refine your pitch, learn about your customer, and it’s relatively cost-effective.

This article here by the founder of intercom was actually pretty influential:

How did you acquire customers/subscribers/users?

Sam and I have always through of customer acquisition as an engine – a system that works to consistently bring on new customers and keep them engaged. Just like an engine, a bunch of parts need to work together to get things to really move. For any company focused on small to medium business clients, customer acquisition is really one of the top questions.

Your funnel, your product value, your customer, your pricing, other solutions in the market, and your marketing tactics all need to mesh.

What we’ve made work to date is email, SEM, and referral/word of mouth. We also have a bunch of active experiments (currently that’s getting press). One secret weapon is our Head of Marketing, Joy.

My favourite author on this subject is Brian Balfour ( I highly recommend reading his stuff.

Once you developed a user base, how have you maintained it?

For our business, it’s about delivering an amazing experience and helping our Experts be really successful at their job. A great transaction with any company builds trust, and for Lorem that is really true.

We focus on being incredibly convenient and wowing on every transaction. When a problem or project comes up, we really want to be first to mind.

By being super convenient and reliable Lorem has become the ‘tech team’ for lots and lots of non-technical businesses. Several Lorem users have even done over 100 projects through the platform.

What software/platforms/tools have you utilized since launch? Which have worked / not worked?

Part of Lorem’s thesis is that the explosion of SaaS tools / DIY software is creating a huge need for on-demand technical expertise. The answer to this question 7 years ago might have been 3-4 tools long, but today a three to ten person company can quickly name 12 – 15 tools they use to run their biz.

Here are a few we use:

Slack, Asana, Typeform, Zapier, Gmail, Glitch, AWS, MongoDB, Google Docs / Sheets, Trello, Sketch, Sublime, TeamsID, WordPress, Unbounce

TeamsID has worked alright, but I’ve always been frustrated by password management. LastPass, Dashlane, and a few others really didn’t work for me.

How did you fund your startup and how does it make money?

Sam and I bootstrapped for about 9 months before we got to the Lorem we know today. That was a wild ride, but I highly recommend every founder do it if they can. It truly reshapes your perception of money and how to do things faster and for less.

Our first outside investors were TechStars. We were part of the Boston Winter 2017 program – it was amazing! Coming out of TechStars we raised capital from two great VC firms (Flybridge and Founder Collective) and six angel investors.

We make money by taking a fair fee for each successful project. We also have subscription clients who pay for ongoing work each month.

What were your KPIs when you started, have they changed?

We track a bunch of different metrics, but GMV (total transaction value) and # of new projects have always been very important.

Interestingly our KPIs haven’t changed much. We track more now than before, but luckily we got good advice from some smart people at TechStars.

To date, what have been your biggest challenges as a company? What have you done to overcome them?

Building a two-sided marketplace that offers on-demand services isn’t easy. We’ve always been a lean mean team, and almost constantly there is more work to be done than human hours at our disposal. This challenge isn’t unique to us, but we overcome it with intense focus.

To us, this means doing work that directly ties to our goal and saying no to lots of stuff that is “not what we’re focusing on right now.” Here’s an example: after TechStars, we continued to grow on the back of our MVP product. After a few months, it became clear that we couldn’t continue to grow on the back of our MVP product while building V1 of Lorem.

It was a critical moment, and we needed to realign the whole team on product development. Only by using our ability to focus (and change focus) were we able to pull it off successfully.

What are your plans for growth?

I can’t tell you everything here, but there are some exciting things in the pipe. Joy, mentioned above, has been a huge help focusing us on what works while putting more momentum behind our growth experiments.

In the next few months, you’ll see some great product improvements and more interesting content for potential customers. We’ve recently launched affiliate and customer referral programs.

If you had to do it all over again, would you?

100%, It’s been said 1000x before, but starting a company is one of the most challenging and rewarding things you can do. I’m just happy that I’m solving a problem that I really care about with a team I really care about.

If I set the clock back two years, I would have sought out even more mentorship from the start. Sam and I were humbled after our first six-month foray into startup land. It was only then that we realized how important it is to seek guidance and advice from smart people who have done it before. For me, there was a strange paradox I needed to reconcile. On one hand, you have to completely believe without any shadow of a doubt that you and your new company will succeed. On the other hand, you need to acknowledge that you’re a first-time founder and there is a mountain of knowledge that you don’t have.

Bringing this new attitude at TechStars was one of the best moves we made. We were the youngest founders and the smallest team, but we did the most mentor meetings during the program while trying to run the business. The 60+ mentor meetings showed others how hungry we were, and it helped us scale our learning rapidly during those two months.

Lastly, if anyone reading this wants to know more about your company… where do we send them?

Our website!