Interview with a Successful Startup Founder

From side project to raising $450k - Building the remote work future

Luke Thomas
Luke Thomas
April 22, 2020
Category of startup
Software & Hardware
Country of startup
United States
Revenue of startups
$10k-$25k/mo
Interview with a Failed Startup Founder

From side project to raising $450k - Building the remote work future

Luke Thomas
Luke Thomas
April 22, 2020
Category of startup
Software & Hardware
Country of startup
United States
Cause of failure of the startup

Luke had an idea: a tool that would help managers communicate with employees. It wasn’t until 2 years later that he began working on it. He kept it as a side project for a long time, while growing it to +$10k/mo. Recently, Friday raised $450k with the aim of expanding the business and doubling its team.

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Hi Luke! What's your background, and what are you currently working on?

Hey everyone! I’m Luke, the founder of Friday. We’ve built software to help you stay connected at work, no matter where your team is based. After 6+ years working remotely for a few different companies (in a variety of roles), I’m productizing my most important learnings and making it easier to implement what the best teams and companies do (albeit manually).

The reality is that communicating with people who are in different locations isn’t easy, but it doesn’t need to be so difficult. We’ve built software to help you create better communication processes at work to help improve the flow of information and keep everyone connected and on the same page. In many ways, Friday approaches communication at work like an engineer might think about architecting a codebase. It looks something like this:

Friday App

I’m 28 years old and I live here in the beautiful city of Portland, Maine with my wife, 17-month-old son, and two dogs. Outside of work, I like reading and being a dad.


What's your backstory and how did you come up with the idea?

I started thinking about the idea behind Friday in 2013. At the time, I had just left a company because I didn’t have a great relationship with my manager. I was struggling at work, but didn’t feel comfortable bringing this up because he didn’t ask, “how are things going?” The best managers I had in the past had regular 1-1s and would ask questions on a regular basis.

After this experience, I thought there was a way one could build software to help managers improve the communication and feedback loop between employees/leaders. Unlike a busy manager, a computer would never forget to ask questions as long as it was programmed correctly.

I sat on the idea for a couple of years, pitching the idea to friends and executives. People seemed to like the idea, but I didn’t have a working product at the time so I wasn’t able to determine if this was a good/bad idea. Finally, in late 2015 I decided that it was time to stop thinking about the idea and time to start building something. I guess they call this making the transition from a wantrepreneur to an entrepreneur :)

Over time, the idea has adapted. I tried selling the product as a “manager sidekiq” and experienced some success with it (growing to $10k/mo as a side project), but I constantly felt like I was missing out on something much better.

Around this time last year, I was reflecting on a variety of data points from customers, advisors, and my own personal experience and came to the conclusion that we could create a customizable tool to run any regular communication event/update at work. Instead of being a tool to improve the employee <-> manager relationship, this could be a tool to help you create communication habits at work. Things clicked for me and I became excited about the idea. At the time, this was still a night/weekend project for me, but I knew that I needed to make the jump and go full-time on this.

The way I look at the market is that there’s plenty of tools that improve the efficiency of workplace communication. Slack makes it easy to chat with coworkers. Zoom makes it easier to have video calls. But there’s a need to help you create a better communication process. It’s not enough to have the tools. You need to think about your process as well. It’s like having plumbing in your house, but not having pumps to regulate the flow of water.

Friday Dashboard

This pivot was risky, but I’m so glad we did it. The best part is that we were able to bring over many existing customers to this new product and they are using the product more than they have in the past. That feels really good. It validates our shift in direction.

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How did you build Friday?

Originally, I hired a software engineer in Europe to help me build out the first version of the product. I was paying for everything out of pocket, so I was trying to keep costs low for the MVP.

This took 2-3 months and then I started trying to convince my friends to start using the product with their teams. A few decided to help and gave me some great feedback. Within a few months, I had my first paying customer, which felt great and validated (in my mind) that this was valuable enough to pay for. I started off charging $5/month per person. The pricing certainly wasn’t ideal, but it was close enough that it worked for the majority of our customers.

Over the next several months, we continued to improve the product (keep in mind, the product itself looked terrible as you can see in the images below), but people found enough value to pay for, which was all that mattered for me. Additionally, they recommended it to other leaders inside their company, so we were able to grow the accounts over time.

Friday UX


Friday Feedback

I didn’t formally “launch” the product publicly until a few weeks ago because I was embarrassed about it (a mistake in hindsight). We finally launched on ProductHunt a few days ago. Instead, I relied on content marketing and various hacked together marketing ideas to generate enough interest to get people to signup. If anyone signed up for a free trial, I’d instantly reach out (oftentimes manually) pretty much-begging people for feedback.

In many ways, this was like pushing a snowball up a hill. You expend a ton of energy to move the snowball, but at least you are making some forward motion! If you are an entrepreneur, do everything you can to get one people’s radar (within reason). Most “big bang” launches don’t go as well as you want anyways.

Overall, Friday has been a journey of constant iteration, frustration, and excitement. But I think that’s the same story for any company. It takes time to figure things out. There’s always something that needs to be improved. There’s always a fire to fight. For me, that’s what makes running a company exciting. There’s a new challenge every day that needs to be solved.


Which were your marketing strategies to grow your business?

I’ve tried all kinds of things, including:

  1. Leaving comments on Harvard Business Review Articles on related topics
  2. Writing content/guides on popular topics like 1-1 meetings.
  3. Liking and following people on Twitter based on what they were talking about

Distribution is one of the most difficult things you need to think about when growing your company. What insight or advantage do you have that your competitors don’t? Many marketing channels can be competed away (like paid advertising), so ideally, you should find something that gets easier as you grow.

I consistently find that the best use of my time is to talk to existing customers and improve the product so it’s more of a must-have. If I do that, people will tell their friends about it.

My best piece of advice for marketing is to ask your customers/prospects a very basic question - “what resources do you visit if you’d like to learn more about [insert topic here]? 

I think of customer acquisition like fishing. You need to go where the fish are. How do you know where the fish are? You ask them where they like to hang out :)

We tried many experiments that failed as well. For example, at one point I paid for advertising and it was a complete waste of money. If you have even a trickle of people signing up on a regular basis, your time is best spent learning how to improve the product for those users. If you wow them, they will tell their friends.

What are your goals for the future?

I have a few goals. I’d like Friday to be a must-have tool for distributed teams and to make work better for as many people as possible. I lived in a small town of 900 people, so I’d like to do everything I can to provide interesting work opportunities to people, regardless of where they live. You shouldn’t need to live in a big city to find meaningful work, especially if you have a skill.

Secondly, I’d like business to be a vehicle for doing good for all stakeholders (investors, customers, etc). I think business provides an amazing vehicle to help others and make the world a better place. Many business owners don’t take advantage of this opportunity but I’d like to do things differently. It would make my day to be known as a great place to work, who does good things in the community. 

My personal goal is to be able to provide for my family in a way where we don’t have to worry about finances all the time. I’d like to be in a position where I can help others who are less fortunate, both from a time and financial perspective.

Finally, I’d like to buy a nice piece of land someday too. Growing up, I loved playing in the woods. I’d like to get back out there!

What were the biggest challenges you faced and the obstacles you overcame?

I don’t want to dramatize my experience as I know there are many others who probably have gone through a lot to grow their business. 

My biggest challenge was around this time last year. My newborn son was colic (i.e. - he would always cry for no obvious reason) and I was trying to balance my full-time day job alongside building Friday and keeping customers happy. Additionally, we were trying to sell our house and move to a new location. To make matters worse, I was renovating the new house on my own (flooring, trim, etc).

It was one of the most stressful times of my life, but it taught me to be patient. With that being said, I’m so thankful that the season is done. It was brutal.


Which are your greatest disadvantages? What were your worst mistakes?

My biggest mistake was in the early days of product development. We had just closed our biggest customer and had just spent a bunch of time building out new features. Long story short, we onboarded them and it was a disaster. Notification emails were sent to the wrong customer, so people would see a “Bob completed an update” email, whereas Bob worked for a different company.

That was massively embarrassing and in many ways a breach of customer trust. It was one line of code fix. If I had taken the time to QA a bit more, it’s possible we could have caught the issue.

I really don’t like letting our customers down. I try to take this as seriously as possible and not take their trust for granted. My biggest mistakes are things I should have caught with a bit more time/effort/attention.


If you had the chance to do things differently, what would you do?

I would focus all my energy on finding a product hook and building around a narrow use case to start. It’s so easy to expand and add features with the hope of finding something that works when in reality, simple solutions work. This allows you to get the most bang for your buck when doing product development.

I might also look at markets that are not “hot.” The hotter the market, the more competition. You may like the competition, but your probability of success may be lower.

I’d also make sure that the product solves a personal pain point. There was a time at Friday when I was building for a different target market and it was brutal. I didn’t enjoy it. It’s so much easier to get excited about a product that you personally find value in.

That’s really it. As a look back on the journey, there’s a very real possibility that I wouldn’t be here now if it wasn’t for the winding journey along the way.


What are some sources for learning you would recommend for entrepreneurs who are just starting?

For startups, I would strongly recommend reading or watching anything by David Sacks, Peter Thiel (like Zero to One), Keith Rabios, or Paul Graham. I would avoid most advice unless the person has an established track record of success. You should even take what I say here with a grain of salt.

Outside of startups, I’ve found a lot of value in reading older books. It’s much easier to pick up on timeless principles vs. the trends that may die out over time. Specifically:

  1. My life in advertising/scientific advertising (Claude Hopkins)
  2. 22 immutable laws of marketing (Al Ries & Jack Trout)
  3. High Output Management (Andy Grove)

My most important piece of advice is that entrepreneurship is about doing. You can read all the books in the world, but at some point, you need to do something. Focus on improving the rate of your learning, stay close to customers, and ask lots of questions. They will show you the way...or at least help you make constant progress :)

Where can we go to learn more?

There are a few ways to connect with me if you’d like to chat more:

  1. Twitter
  2. Personal website
  3. Friday website
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