How Dan Corkill Turned $30k of Savings Into a 7-Figure SaaS Business

In 2011, Dan Corkill started a SaaS business with just $30,000. Today, Follow Up Boss is a multi-million dollar business. Here's exactly how he did it.

Dan Corkill Follow Up Boss

In 2011, Dan Corkill walked away from his day job with $30,000 in savings, a technical co-founder, and the desire to “build a SaaS app”. He was partnering with Tom Markov, an engineer he met through his previous work.

After some initial research, they decided to create software that helped small business owners follow up on online leads.

Existing products were either too simple (think Highrise, which didn’t even have an email search function) or too complicated (can you say Salesforce?).

But for six months, the early version of Follow Up Boss floundered. Worse, the pair were generating exactly $0 in revenue. Customers would sign up for a free trial, then wander elsewhere.

Looking back, Dan realizes that “there was no reason for them to buy.”

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Today, it’s a different story.

Among SaaS examples, Follow Up Boss is a standout with over 20,000 customers, 18 employees, and an ARR in the multi-million dollar range.

So what changed? They got serious about one specific group of people: real estate agents.

We interviewed Dan recently to learn more about his story.

Here’s what he told us about finding a market, why it matters and how he turned that focus into a successful SaaS business.

(Note: One thing Dan did really well was survey his customers to determine that real estate agents were his right target market. If you’re still trying to figure out who you should sell to, why not survey and segment your existing customer base? Fieldboom can help.)

Looking for a Large Market? Consider Thinking Smaller

SaaS examples: Think smaller, you can't appeal to everyone.

The current homepage of Follow Up Boss, which now focuses entirely on real estate agents

Dan and Tom knew two things starting out:

  1. They wanted to build a SaaS app
  2. They wanted to help small businesses follow up on leads

But that alone wasn’t enough to build a successful business.

Their mistake?

“Small business owners” is a MASSIVE target market. They don’t all have the same needs and pain points.

Follow Up Boss’s early positioning was way too general to appeal strongly to anyone.

So, they narrowed their search by looking at distinct categories of small business.

Eventually, they decided to target real estate agents. Real estate agents had several characteristics that made them a good target:

Their contact information is all online

Cold outreach, both for research and sales, was a reality of running a SaaS startup for Dan and Tom.

With real estate agents, it was easy to find contact information — most agents have their information readily accessible online.

If you speak to them, you’re speaking to a decision-maker

Real estate agents have to answer the phone. It’s literally how they make their living.

If you call an agent, you’ve got good chances of reaching someone who has the authority to say ‘Yes, I’ll sign up for the free trial.’

They can’t afford complacency

Real estate agents are paid on commission.

Their income depends on how many leads they can convert into sales. Without a good system to follow up on those leads, they’re not maximizing their earning potential.

Anything that can increase their work efficiency, lead generation, lead capture, etc, is sure to attract their attention.

Their revenue range supports software subscription costs

When you’re outlining your target audience, Dan recommends considering their revenue levels.

For example, you could decide to target only businesses likely to have $100,000+ in yearly revenue.

Of course, the ability and willingness to pay for software are equally important.

“We want them to be paying for software already. If they’re not already paying for software, you don’t want to be trying to convince them that software is good. You want them to be used to putting their credit card in and doing trials,” Dan explained.  

They comprise a sizable market

There are roughly 2 million real estate agents active in the United States. That’s about a fourteenth of the 27.9 million small businesses in the USA.

But it’s still plenty large for a SaaS startup — and that doesn’t even include global possibilities.

Dan has seen people “get crazy” about market size. His take is that you don’t need to spend all your time verifying market size.

Essentially, “you just want to know that there are enough people to sell to,” he explained.

Best of all, they learned that real estate agents were already buying CRM solutions. Those solutions just weren’t meeting their needs well.

Rather than look for a brand new market, Dan and Tom were happy to create their own space inside a healthy market.

Pinning Down Pain Points: How to Talk to Your Audience

SaaS examples: How do you talk to your audience?

A quick summary of accomplishments on the About page for Follow Up Boss.

Clearly defining who you serve with your business is a critical step towards success. Once Dan and Tom made that decision, they dove head-first into customer research.

What to Ask Your Customers

As soon as Dan knew that he was targeting real estate agents, it was time to start contacting them.

He wanted to learn everything he could about their businesses, their pain points, and what they would want in his software.

Here are some of the questions he asked agents while planning Follow Up Boss:

  • What’s the biggest problem in your business at the moment?
  • How much time do you waste doing [insert relevant process]?
  • If you could wave a magic wand and have anything happen, what would that be?
  • Tell me about your business. What does your day-to-day life look like?
  • How much money do you make?*
  • Tell me about your employees. What are their roles?

(Note: Check out this market research survey we’ve created. It includes Dan’s questions above. You can create a beautiful survey like this one in 5 minutes with Fieldboom.)

Be tactful with these questions. Some people are happy to share revenue information, and others are reluctant to talk about it at all. The key to making these questions work? Dig deeper with follow-up questions.

“If I rephrase the question and ask it a second time, I’m going to get a much better answer,” Dan explained.

Follow Up Boss Team

The Follow Up Boss Team

“Learn and be a sponge,” he emphasized.

Remember: you’re not there to sell them something. You’re there to become the “absolute expert” on the problem you’re trying to solve for them.

Also, don’t worry about ‘bothering’ the people you ask to speak with you…

People aren’t asked these questions very often. In Dan’s experience, almost everyone is happy to talk about their business and their struggles.

And their answers to the questions you ask them will help you determine which features are most important for your software.

Where to Find Your Customers

At first, traditional networking methods can be extremely useful. Dan and Tom had a business acquaintance who introduced them to several real estate agents in the early stages of Follow Up Boss.

But personal connections only go so far. Finding sustainable sources of customers to speak with (and eventually, sell to) is the goal.

Search Forums

Dan looked for forums on topics like “lead management real estate”. There, he found plenty of real estate agents interested in better lead management.

When he came across someone who wasn’t happy with their lead management (as evidenced by their posts on the forums), he would send an email to that person.

Keep an eye on people who are looking for a service that you can provide

Posts like this one from a forum on Bigger Pockets served as Dan’s first leads for Follow Up Boss.

In the email, he’d ask if they’d like to chat about what they would want in a lead management system if he built one. “If people have that pain, and someone’s offering to solve it for them, it’s very likely that they’ll say yes,” he explained.

Get Active in Facebook Groups

As long as you don’t spam Facebook Groups and get yourself banned, it’s a place you can find many quality leads. Those groups were “massive” for their early growth.

Just take popular Facebook group “What should I spend my money on?” (14,000 members strong today). Such pages were the perfect place for him to grow relationships.

He would answer questions (if you don’t know the answer, Google can help) and generally make himself visible in a good way. Eventually, many groups would have someone ask, “What CRM do you use?”

That’s when Dan would chime in.

SaaS examples: How do you generate leads?

Dan added value to the conversation while piquing realtors’ interest on this thread from the group: What Should I Spend My Money On?

Eventually, he would tell interested agents to drop him a PM if they were interested. Sometimes, he would get 50 private messages from just one thread.

Leverage Influencer Marketing and Referrals

Once Follow Up Boss grew, referrals took off. Real estate agents are happy to talk to each other about the tools they use and share information, so his business grew primarily by word of mouth.

Today, Dan doesn’t have to comment on those Facebook Group CRM threads — his clients do it for him, unprompted.

SaaS examples: Lion Desk or Follow Up Boss?

Now, Dan doesn’t have to market his business in Facebook groups: his customers do it for him

It’s a testament to the quality of his solution. They also benefited from influencer marketing. At some point, they sat down and wrote a list of all the people they’d love to have promote Follow Up Boss.

They’ve already been promoted by 70 to 80% of the people on that list, without heavy outreach on their part.

As it turns out, finding influencers for marketing in a niche isn’t as hard as Dan thought it would be. If your solution benefits someone, they’re often happy to plug your product.

Will These Strategies Work for You?

Dan launched Follow Up Boss after quitting his job with just a $30,000 runway and no venture capital. It’s an entirely self-funded business.

Dan made it work by traveling Europe, keeping his living costs low and focusing entirely on the business (“baselining,” for those in the know). If he hadn’t quit his day job, he’s not sure Follow Up Boss would have ever existed.

“The more your back is against the wall, the more you just have to do it. How do you have that persistence and patience to make it all happen?”

That’s not to say you can’t start a business if you’re “locked in” to a job that pays your mortgage and feeds your kids. Plenty of people do. But Dan was grateful for the ability to dedicate himself — without distraction — to building his company.

As a result, he had the time and motivation to find and cater to an underserved population in the wider market of small business owners. That tenacity in seeking out and understanding who he served made all the difference in his business.

(Note: One thing Dan did really well was survey his customers to determine that real estate agents were his right target market. If you’re still trying to figure out who you should sell to, why not survey and segment your existing customer base? Fieldboom can help.)

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EJ left a career in UX/UI to write full-time. She believes in user-centered design and advocating for diversity in the tech field. Follow EJ on Twitter @whatiwritewith