Freedom Found!

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.

Our Core Values

1 Customer obsessed

Again: customer obsessed. Not part-time passionate, but full-time fanatics. What makes us unique is how close we are to our users. The work we do together is driven by our commitment to solving their problems. We seek opportunities to build loyalty through that promise. Delighting customers when possible isn’t going the extra mile, it’s standard.

2 Kindness & 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 game plan 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

We’re built on a foundation of trust and empowerment. Everyone has total ownership of their projects & ares of expertise and is relied on to deliver. We’re accountable for seeing projects to their end, not just doing our part and hoping the next person does theirs.  That does not mean there is pressure, it means we check in with one another to ensure things move forward and decisions are made with little input from above because we trust our people.

6 100% Remote, 100% available

Despite our team being fully remote and asynchronous, we make time for each other. We know that to do right by our users, we need to occasionally sacrifice for meetings and work odd hours. That access to each other and open communication creates an environment where iteration & improvement thrive.


We put users back in control of their business

We’re on a mission to build a land investing platform that makes it simple for land investors to run, scale and organize their business processes.

Enabling owners to create frictionless systems that allow them to get out of the mess of operations, admin and day-to-day craziness and put them squarely back in the driver’s seat of their company.

To get users above the noise so they can truly be empowered to make informed, strategic decisions.

Every feature we build is crafted with the intention of protecting our client’s status as owners and entrepreneurs and not turning into operators. To be tactical decision-makers, not administrators.

To not just feel productive with busywork but to actually be productive and chart the course for their land investment business.

Everything we do empowers people to buy back their time and invest it where it matters most – in being leaders.


The best isn’t enough

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.


Integrated & Distributed

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.


Happy Team + Happy Clients = A Windfall

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.

clients and growing
by X% year over year


annual recurring

$4 Million



Media & Awards

We’re not hit wonders

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.


Tomorrow is even brighter

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 & 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.