It’s July 1st, 2025 and we’ve helped over 2,000 of our friends – what we consider our users – find freedom through land investing. We’ve empowered them to choose how and where they live and work; simply put, we’ve made their lives better.

Pebble is synonymous with land investing and we’re helping people succeed no matter which investing strategy they use. It’s friction-free.

Inspired by the positivity and productivity of our company retreats, we’re fresh off the heels of our 2nd annual Pebble Beach retreat, where our growing community comes together for workshops and a lot of fun.

In the process of helping so many build their dreams through land investing, we’ve exploded past $4 million in annual recurring revenue in 2023 and are on target for $5 million next year.

All this is possible by sticking to our principles and checking everything we do against our values.


1. Help First

Whether it’s our users or team members, we want to help. What does that mean? We strive to make people’s lives easier and better. Less stress, more joy. If we can help each other, we can create wins for our customers.

2. Kindness and Respect

We care about our users, each other and ourselves. We communicate candidly but kindness is at the core. Respect for our user’s needs and our own is where all our decisions come from.

3. Progress Over Perfection

We simply cannot move forward if the goal is getting it 100% right. Meeting deadlines builds trust. They matter to our users, so they matter to us. Deadlines are always met; we get things out on time and then create a gameplan for smart improvements as needed.

4. Continuous Self Improvement

The more we can grow as people, the better results we can achieve for our clients. Our team is motivated by being 1% better than the day before, whether it’s running, reading or learning a language, becoming better is second nature – and we support everyone’s pursuits.

5. Accountability to Deliver

The more we can grow as people, the better We’re built on a foundation of trust and empowerment. Everyone has extreme ownership of their projects and areas of expertise and is relied on to deliver. That does not mean there is pressure, it means decisions are made with little input from above because we trust our people.

6. Work Anytime, From Anywhere

The freedom we help our users build starts from the freedom our team has. We practice what we preach about creating our own lives and choosing how we live. We rely on our fully distributed team to get things done while remaining flexible and striving to be available for each other.



Our purpose is to help others build their dream lives.

To free our users from the old way of living. From the stress and daily grind to a new life of empowerment and freedom. The goal is the same for our team, to empower them to lead the lives they want.

We’ve created an ecosystem around that and invest thousands a year into bettering both our product and our people. That means continuous improvement of our platform and investment into tools that allow our team to flourish; travel, training, mentoring, whatever it takes.

A stronger, more committed team leads to more satisfied clients and a better experience. We’ve seen the results of this firsthand through the growth of our community. Those relationships we’re building genuinely matter and it’s not out of the ordinary for our team members to receive gift cards from ecstatic users after they’ve been able to scale and grow their land-investing business.

This is a byproduct of creating the land investing platform.



People trust our tools. Land investing is a mess without Pebble and our customers routinely tell us that we’re the first company to clean it up. The one solution that brings it all together. We just make it easy.

We’re a no-brainer for anyone in the space. Even those that are just curious about land investing are aware of us through our founder’s media appearances, like the Bigger Pockets podcast, where Jessey was a recent guest. 

The development of Pebble over the past 3 years, the fine-tuning and iterating, has made us the name in land investing.

When you think email, you think Gmail.

When you think eCommerce, you think Shopify.

When you think land investing, you think Pebble.

We are the go-to because the alternative of creating a hodge-podge system is so unattractive and costly. We’re known for being the centralized homebase for land investors of all sizes. We pride ourselves on being the easiest solution to get started with as well. Our onboarding is intuitive but nonetheless, someone is always available to assist because our team has a help first mindset.

Because of this, our market share is 3 times higher than our closest competitor and our best-in-the-business sales team consistently exceeds their quotas.

Being the best software isn’t enough though, it’s not about that. The lives we improve and the relationships we foster is our barometer for success.

We work with people, not numbers

Our users are our friends. They’re not stats on spreadsheets or data points. They’re real people and we strive to have meaningful relationships with them all. We know them by name.

We do whatever it takes to earn their trust and we find that the easiest way to create that trust is to genuinely care. It can’t be disingenuous or phoned in and that trickles down to who we hire.

The way we know we’re being effective in creating lasting relationships is a unique one; gifts. It’s become standard at Pebble that our users are so thrilled with our service – and us as people – that they want to personally say thank you. Sometimes that’s a gift card, sometimes it’s abundantly kind words of praise in an email. Anything positive and real is a gift and it’s our gold.

We’re even known to give our clients gifts too, a birthday card, tickets to a ballgame or a stuffed animal for the newborn daughter. We care and people notice. It’s why our word-of-mouth buzz is so strong.

The key to all of this is one thing: relatability. We’re just relatable. Our founders regularly do live streams and webinars. They answer questions. Our team is the same. In fact, we now have an annual event devoted to bringing the user community together – in person. We get a few dozen folks together and talk about land and business, share some laughs and deepen our connections.

We may be a SaaS company, but we always treat people like, well, people – and in turn our customers treat us with utmost respect too. Great culture leads to great relationships.


We work from anywhere.

As long as we have internet, we have an office.

Our team is 15 members strong and each has extreme ownership of their projects and tasks. We don’t micromanage, we empower. We do this because it works and our growth proves that.

Just because we’re distributed globally doesn’t mean we’re disconnected. We’re cozy and we talk to each other. We care about each other and are there for each other. Pebble is known in the industry as an extremely fun place to work because of the freedom we guarantee – and our annual retreats. They’re flat-out envied by folks at comparably sized companies.

That freedom extends to decision making too. Empowerment means we trust our team to make decisions with little input from above. Individually, we all deliver and constantly exceed the goals that are set, which means collectively, our team moves mountains.

Perhaps the best part of our team is the varied interests and life experiences we all bring. We’re a group of thought leaders in the areas we love, whether they’re related to land investing or not. We’re a diverse team built on passion and professionalism that performs at a high level in and out of Pebble. Ironically, it’s that individualism that makes our team strong.



The proof is in the pudding and you can’t fake numbers. We tirelessly improve ourselves, our product and the lives of your users and that shows up in our figures.

  • 2,000+ clients and growing by X% year over year
  • $4 million annual recurring revenue
  • X% profit



Given the huge impact we’re having in our clients’ lives and the constant stream of success stories, it’s no surprise that we’re getting tons of attention. On top of appearances on Bigger Pockets, one of the marquee real estate specific podcasts out there, our founders have also appeared on The REconomy, Real Estate Today, The Art of Passive Income and more.

It’s not just podcasts either, traditional media is talking about us too. We’ve been written about in Forbes as the go-to in maximizing land investing returns, in addition to features in XYZ.

The buzz from all of that works its way onto our social channels where the engagement is robust and energetic. The more people see us featured, the more confident in their decision to be part of our community and shout it from the rooftops.

Awards have followed all this buzz and we’ve picked numerous industry awards and small business accolades.



With our values getting us to where we are today, we’re going to continue to lean into those principles going into the future. Practicing what we preach has been vital to our success and that consistency will carry us forward.

It comes back to what’s at our core:

  1. Help First
  2. Kindness and Respect
  3. Progress Over Perfection
  4. Continuous Self-improvement
  5. Accountability to Deliver
  6. Work Anytime, From Anywhere


As long as we stay the course, we’re beyond confident that we can change even more people’s lives and give them the pathway to freedom that they so richly deserve.