How did you get your first paying customer?

Google marketplace

When we started, we listed our app in the Google marketplace. That's how we get our first paying customer.

- Mei Siauw, Co-Founder, LeadIQ

Provided free services first

My first paying customer was the U.S. Navy, who became my customer after providing free services to them. They valued the free services so much, they asked me to start a company to provide additional such services. This was the impetus for founding Design Interactive; although I had aspired to start a consulting firm upon entering grad school and the request from the Navy provided the tipping point for establishing a value proposition.

- Kay Stanney, CEO and Founder, Design Interactive

In-person cold calls

The short answer is in-person cold calls at libraries. We went door to door and said to the head librarian, "We build mobile apps for libraries, if we look out now at the floor of the library and at least half of the people are not on their phones, then we will leave. Otherwise, you need a mobile app." They looked and we were right. So, that single line introduced us to over 4,000 libraries worldwide and over 5,000,000 users. We parlayed that into a business we sold, then used the same technology to build a B2B prospecting tool that has carried us for the last 8 years.

- Greg Carpenter, CEO and Founder, Troparé

'Nuff said

by proving we could drive more revenue for them = )

- Joel Montaniel, CEO and Co-Founder, SevenRooms

Entrepreneurs Organization Membership

My first paying customer - a fellow CEO/entrepreneur - came through our affiliation with Entrepreneurs Organization (EO). He knew about my new business and asked if it would be a fit for his company. I said, "Let's find out!" The first 25 paying customers came through relationships I built by being an EO member. Network = net worth.

- Adam Robinson, CEO / Chief Hireologist, Hireology

Need first

understood a burning need, did 6mo of market research to validate it would be a real business, spent 2.5 years on R+D and building a hardware and sales team and passing the FDA, then sold our first product after all that time to (thankfully) glowing reviews

- Dwight Crow, Co-Founder & CEO,

Built for friends first

We built the first version of Carbonmade over a three-month period in 2015 to manage our agencies' portfolio website and decided to share it with our close friends -- because, why not! Turns out, most of them were pretty excited to stop hacking PHP files or bugging their friends every time they wanted to share some new work. Our friends shared it with their friends, and we quickly realized we may have solved a real problem that has value to people.

Back then, there weren't boxed systems you could plugin and magically start charging your users. SaaS was a new concept and the web2.0 era was just starting. There were a ton of requirements setting up a merchant account -- someone had to come to your house to verify that you were a real business, custom code that talked to our merchant's API needed to be manually reviewed and approved, and you had to sign lots of forms. This took us a few months... and when it was done, we had maybe 500 people using our service.

We sent out an email, opened up the system to the public, and within a few hours -- got our first paying user to our aptly named WHOO! plan. WHOO.

- Jason Nelson, CEO, Carbonmade

Just go out there

You just have to go out and do it. There's no secret to it. People get in their heads trying to over-optimize and reduce the risk of failure, or think that if they fuck up completely the first time that it means they're stupid and a failure and it wasn't worth trying. Nothing could be further from the truth. Just go out there, find someone you think might even in theory give you money for your thing (even if your thing isn't finished yet!) and then see what they say. They'll probably say no! But just make a guess as to why they said no, and think about whether you could change the way you're asking them to make them more likely to say yes. Then just go do that a hundred more times. It helps a lot if you focus on the small discrete steps and taking the next small discrete step, instead of getting lost in your emotions about it or getting lost in the intellectualization around all the implications one specific "no" has to the overarching framework of what you're building/why you're doing this in the first place/how hard doing it this way will be and wouldn't it be worth my time finding a more efficient one?/ etc etc etc

- Gleb Polyakov, CEO, Nylas

Sell the vision of what you are doing

Getting the first paying customer is all about hard work and salesmanship. Find any people in your network and sell them the vision of what you are doing. Rinse repeat until you have one. Then knock it out of the park. Make them an evangelist and they will help you sell the second. The second is a tiny bit easier. The third a tiny bit easier than the second and so on... But so many fail because people don't focus on making those early customers happy. They will be your best sales tool (especially in enterprise software).

- Thomas Coolidge, CEO & Founder, Nexus Systems

Industry tradeshow

We got our first paying customer at an industry tradeshow.

- Dan Pollard, Founder / CEO, myDrugCosts

Startup conference

We met our first paying customer at a startup conference where we presented on the problem area that our company was solving for. The customer approached me afterwards and asked how we were really solving these problems and we were able to convert that to a POC and then a customer.

- Hersh Tapadia, Co-Founder and CEO, Allstacks

Selling before incorporating

Long story short, we had a minimum viable product (MVP) that my partners had developed as part of a website tool and had a few customers using. Our first official meeting we presented the idea and the MVP and he was ready to sign up, we didn’t have a price point in mind or a company at this point, however he wanted what we discussed and showed him. He wrote us a check for 4K, we incorporated the business later that week so we could cash the check. We quit our day jobs and started the company - however it’s important to know this was 2006 and saas or delivering a specific vertical market solution was early - timing was on our side, it would be much harder today in my opinion because everyone is caught up. 15 years later we have over 16k customers globally, 500 plus employees, and are very thankful for the first customer that gave the motivation to get launched!

- Dan Houghton, Co-Founder & CEO, Buildertrend

Constant networking to get market feedback

From the time I first conceived of this new product concept, I was constantly networking with CMOs and influencers in the market to get their feedback on how big the problem is, how urgent it is to solve, and how well they felt the concept solved the problem. This also guided our scoping of the MVP. While we were building the MVP, one of the biggest fans I had developed during the feedback phase let me know that the person who runs the department we sell to, was looking for a better way to manage the area we serve, so he made the introduction and got us an invitation to meet with the team. Our MVP was a really good fit for what their needs, and the sale happened quite quickly. BTW, this is very similar to how I got our first dozen paid customers.

Lesson for other entrepreneurs: You should always be meeting with potential buyers and influencers to get feedback, because people love to give feedback on something new since it makes them feel like they are on the leading edge. It is much less threatening to them than asking to come in and pitch them something to buy. Yet so many of these meetings will quickly shift into a sales opportunity if you have a compelling solution.

- Jeff Ernst, Co-Founder & CEO, SlapFive

Someone I knew well

For both companies, the first paying customer was someone I knew well that I could explain the value prop to. I didn’t charge them up front but once there was real value being delivered I started charging.

- René Lacerte, CEO and Founder,


Mostly begging and groveling

- Bill Gnerre, CEO and Co-Founder, Interval Data Systems

Passthrough work

My first paying customer was passthrough work from an established business owner who was a strong salesman but didn't actually do the work (or not much of it, I can't exactly remember at this point). I still had a day job and it was a little dicey convincing clients it would be okay even though I wasn't full-time. The business owner who referred me soon shut down his business, so I became the direct contact with the clients. I think that was probably an ideal introduction for me, because it gave me an opportunity to see how someone else handled the process and identify what I thought worked well and what I wanted to do differently.

- Erin Rollenhagen, CEO, Entrepreneurial Technologies Inc.

One of the first apps in the App Store

Avatron’s first product, back in 2008, was an iPhone productivity app named Air Sharing. It was one of the first apps in Apple’s new App Store. I wanted this app to get noticed amid the noise of eight hundred other apps, so I decided to make it free for the first two weeks. I sent beta copies to a few prominent thought leaders in the mobile app space. They gushed about Air Sharing to their followers, who wrote articles in Macworld, The New York Times, Wired, the Wall Street Journal, Newsweek, and lots of other outlets. In two weeks, over a million people, 20% of all iPhone owners, had downloaded Air Sharing.

When I started charging $7 for the app, I was surprised to see that there was still demand. About five thousand people bought a copy of Air Sharing on the first day of sales.

- David Howell, CEO, Avatron

Someone you have worked with before

Your first customer in a new venture is usually someone whom you have worked with before. Someone that knows your capabilities and trust you to deliver. Someone that has a problem you already understand, and now when you say you can do it with your new startup, it seems you have an easier and better way to solve than the old way.

- Rob Kall, CEO & Co-Founder, Cien


Built a Minimum viable product with as little engineering resourcing as possible ⇒ cold emailed the CTO of a bunch of target customers ⇒ got a demo ⇒ closed the deal

- Anonymous

Gave out jars of honey to doctors' offices + honesty

We gave out jars of honey to doctors' offices with our business card taped to it with clear tape. Everyone likes honey and it doesn't just disappear like an inkpen.

This got us in front of a few clients and then we did what we said we were going to do, showed up on time, ALWAYS answered our phone and treated our clients like family - taking their issues and concerns as our own for their projects. We prayed over our business and tithed/gave back to help others, reputation and word of mouth did the rest - we never ran an ad.

We drove to the office of the provider - took a laptop to show him the product - and when he asked us a question we didn't have the answer to, we told him we would find out, and my partner slipped out of the room and DID find out, and then came back in with the answer.

Later, the customer told us THAT was the reason he hired us.

23 years later, here we are.

- Kristi Bubrig, CEO, Authorized Workflow Solutions

Many thanks to these wonderful founders for contributing to 20 Answers!

Have a question you want answered? Click here

Do you have wisdom you'd like to share? Click here

Recent Posts

See All