8 Ways to Earn Your First 100 Customers

Dave Schools, Former Digital Strategist

Article Category: #Strategy

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We asked 8 startup founders to share how they earned their first 100 customers. This is what they said.

When people ask DC-based serial entrepreneur Michael Lastoria for advice about entering the choppy waters of entrepreneurship, he says, “Don’t do it.

It’s a tough road. The primal urge deep within the hearts and minds of entrepreneurs drives them to sacrifice savings, relationships, and sleep to create something bigger than themselves.

They’re the ones at 3:00am, with a Red Bull in one hand and a phone in the other, who work, staring at the glowing laptop screen because they must execute their unshakeable vision.

An entrepreneur consists of three parts: visionary, hustler, and connector. They have a creative vision to solve a problem, they take perspiratory action to achieve their goal, and they know they can’t do it alone: they attract and empower a team of skilled people.

One of the greatest challenges startups face is how to start selling. The business model is ironed out, the product is ready, the team is lean, and the support is in place. It’s time to start generating revenue. Where do you start?

Here are 8 ways successful startups earn their first 100 customers

1. They hustle.

Alex Nicholson, founder of Mariner Exchange, a mobile iOS app that connects boaters with marine service providers, brought in his first users through pure, manual hustle. He quit a well paying job at Morgan Stanley to pursue his vision.

He said, “I remember putting microfiber towels into little plastic bags with my flyer, zipping it up, and getting on my paddle board to go boat-to-boat tossing the fee towel bags onto boats and talking with owners.”

Getting started takes a strict diet of sacrifice. Nicholson recounts the early months of getting his startup going, “I remember getting the same thing at Sam’s Club every month: 12 lbs of pasta, 90 oz of Ragu, 24 Clif bars, 2 bulk boxes of Honey Bunches of Oats, and milk. I ate that 3 times a day for a year. I lost 20 lbs.”

While Nicholson’s example of hustle might seem extreme to you, don’t worry. Thankfully, reaching out cold to your target audience is not the only outbound sales strategy entrepreneurs use. Even the best companies start with friends and family.

2. To go big, they start small.

Fundrise, the world’s first and largest real estate investment crowdfunding platform, is a fintech startup founded by two brothers in Washington, DC. Their product allows non-accredited investors (regular joes like me) to invest money into a digital Real Estate Investment Trust (eREIT) in return for a tiny slice of equity in say, a NYC skyscraper.

Sounds advanced. Yet even the most technical startups begin with their first sales from a close network. Ben Miller, co-founder and CEO of Fundrise, said, “[We started just] like any great internet company ...by hand. We got our first 100 investors by asking our friends, family, and community to invest with us.”

Knocking on doors, whether warm or cold, isn’t the only form of effective selling. Who said you always have to go to a customer’s door? What can you do to make your customers come to your door? IoT startup Aquicore generated its first sales by attracting customers through thought leadership.

3. They are thought leaders.

Thought leadership is the discovery of new knowledge through deep expertise. It happens when you are fully immersed — committing 10,000 hours of your time to a field, skill, or topic.

When he started Aquicore, the Internet-connected energy-saving analytics platform for real estate portfolios, founder Logan Soya knew thought leadership was critical to the initial growth of his company.

Soya said, “Thought leadership leads to a community. We continually strive to challenge the status quo and help guide our community forward. To be a thought leader, you can never stop learning, and never stop improving. We apply the principles of Kaizen to constantly learn how we can do business better.”

It’s true. You could spend decades on the Aquicore website reading resources, case studies, whitepapers and even a dictionary about how to use technology to better manage commercial real estate.

The problem with thought leadership is the same as the tree that doesn’t make a sound when it falls in the woods: no one is around to hear it. In other words, you can write the most current, interesting, and cutting-edge content in your industry but if no one knows about it, then it’s futile. If you build it, they won’t come. You need to build it and then build pathways for them to come. It’s called marketing.

4. They harness the power of community.

Anu Bhaskar, co-founder and CTO at Hurdlr, an automated bookkeeping software platform for freelancers, entrepreneurs, drivers, couriers, and hosts, knew his product would save self-starters great headaches, but only if they knew about it. He had to get the word out.

Bhaskar said, “We spent ample time engaging the moderators (or becoming the moderators) of Facebook groups, sub-Reddits, and forums that pertain to our target users. We shared content that provided immediate value to them, without asking for anything in return.”

By helping the communities in which their customers interacted, Bhaskar opened up pathways for their first 100 “early access” users to find their app beta.

He said, “Their feedback helped shape the product, and the price, and they ultimately became our brand advocates. One of those users has successfully referred over 100 people to Hurdlr!”

5. They understand word of mouth.

Referrals is the engine of business development — without it, it’s impossible to grow. Michael Lastoria, founder of &pizza, a fast-casual, futuristic DC-based pizza chain, and the former owner of an ad agency, credits word of mouth to be foundational to success.

He said, “Word of mouth can make or break your business. It can build you up and tear you down fast. Do it right and you’ll have little need of an ad budget.”

Once you get the word out, only half the battle is won. Or, to Lastoria’s point above, lost. The word of mouth engine requires fuel — something that causes a first-time user to say, “Oh, that’s what they were talking about.”

What is your fuel?

6. They fuel their business development engines.

Zach Perret, founder of Plaid, a platform that enables digital applications to connect with users’ bank accounts (used by Stripe, Robinhood, Venmo, et al.), had the marketing challenge of driving adoption in the developer community.

Yes, his team went to a few hackathons, which helped get the word out, but he really ascribes its initial success to its documentation.

Perret said, “After building a fantastic product, we then focused on creating clean and simple documentation. The developer community is inherently curious, and we found that many people built personal projects when they stumbled on our docs.”

The lesson here is to make your product accessible and easy to play with right away. The last thing you want to do is make a great product but make it hard to get started. Can prospective users “jump right in” when they come to your startup’s website?

As you read through the experiences of other companies, you may catch yourself looking for a formula to follow. Well, in the spirit of bubble bursting, there’s no one single path to success for your startup. There is no formula. That’s part of the fun— and stress — you have to figure it out as a founder.

7. They fail fast, and fix faster.

It took Clarabridge, a 10-year-old company with over $100 million in funding for its B2B customer experience management platform, years of testing and learning to find what works for them. They tried everything.

Sid Banerjee, founder and CEO of Clarabridge, said, “Getting to our first 100 customers was an iterative, dynamic, learning process. We started with cold calling, paid search, and web site optimization, and learned that our first few customers came to us after finding us on Google.  With our first few successes, we invested heavily in customer marketing and trade shows, and used face to face contact to drive more lead development and conversion.  Eventually, we educated analysts, followed company advocates as they moved roles and companies, and established a partner ecosystem of recommenders, implementers, and advocates, all the while continuing to hire sales people, invest in marketing content, events, and evolving our web site.”

Banerjee acknowledges there was no single technique that worked for Clarabridge. “Fail fast and fix faster, and evolve as the market evolved,” he said.

That’s why starting a business is one of the hardest things to do in life. You have to be comfortable with venturing into the unknown, failing often, and capitalizing from the experience. That’s what an entrepreneur does. A teacher teaches. An entrepreneur fails and learns.

8. They don’t wait.

Lastly, don’t wait until your product or service is ready to sell, to start selling. Start laying the foundation years in advance. Sure, it can be cumbersome to sell something that doesn’t exist yet, but look at it this way: it’s a chance to get your messaging right and build relationships so that when the product rolls off the assembly line, you’re ready to go.

David Friedman, founder of Ayla Networks, a startup that connects any product to an IoT platform, which just announced a $39 million series C, said pre-selling can be a little testy with investors, but it is beneficial in the long run.

Friedman said, “We spent about four years building a strong product and partnership infrastructure before we started selling. The attention to detail and focus helped us scale and sprint when we started selling. The hard part about that was getting patient investors who shared the vision and being smart and efficient with our use of capital.”


To sum up what these eight founders have shared, here are the eight ways to sell like an entrepreneur:

  1. Hustle like hades.
  2. Start a community by being a thought leader in your industry.
  3. Tap your network, including friends and family.
  4. Join, interact with, and lead the communities of your target audience.
  5. Word of mouth is your business development engine.
  6. Fuel word of mouth with easy access to your product.
  7. There is no secret sales formula. Fail fast and fix faster to find what works for you.
  8. Start pre-selling before your product launches.

What would you add to this list? How did you get your first 100 customers? What have you found that works well for your company?  If you aren’t there yet, I hope this article gives you some ideas for how to get started.

Thanks to all the founders who contributed to this post.

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