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How an Accidental Agency Owner Built a $2 Million Business

"I have wicked respect for all the agency owners out there because this shit is not for the faint of heart." -Justin Benson, serial entrepreneur and founder of Bara

There's a legendary copy writer named Howard Gossage who was fond of saying, "We don't know who discovered water, but we're pretty sure it wasn't a fish."

His point was that sometimes industry outsiders have the best insights. Distance gives you perspective.

Hampton member Justin Benson is a good example. He didn't set out to start an agency (his background was in tech + real estate), but that's where he ended up. And as a relative outsider, he's brought some very creative ideas to that endeavor. He shares a lot of them here.

My personal favorite is in the growth section, where he talks about how he's partnered with coaches to help their clients execute on their advice. That's a fascinating concept every agency owner can take to the bank.

He also breaks down...

  • Other growth channels that have worked well for them
  • How they structure their retainer model and set expectations with clients
  • Major challenges and "oh sh*t" moments fellow founders will relate to
  • Simplified keys to the business model
  • His main leadership philiosophy
  • And more...

It's a great look inside the mind of a highly intuitive, multi-time founder.

Hello! Who are you and what business did you start?

I’m Justin Benson, half Filipino and half Swedish, trying to survive in the desert of Arizona with two kiddos (Zara and Zion) and my amazing wife (Faith).

A fun fact is that my family is 1st generation from the Philippines and my Grandpa was the mayor of a town called Baguio. Here’s a photo of my grandpa and his bodyguards. They ended up having to flee the country due to multiple assassination attempts and settled in Ventura California.

My grandpa and his body guards

Two years ago, we started Bara Agency which is a fractional CTO agency for real estate teams and brokerages. It’s a really fun blend of both my technology and real estate backgrounds and I enjoy living life in our little nerd cave.

On a day-to-day basis, our agency is responsible for building, maintaining, and continuing to evolve the technology of the largest real estate teams on the planet. In just a short amount of time, we became the thought leaders of tech systems in real estate and are the only company doing what we do at scale.

Currently, we are a team of 14 lovely humans, most of whom are in-person at our office in Tempe, Arizona. It unexpectedly grew to $2m in ARR in about a year and a half even in the rough real estate climate we are experiencing. Currently have our eyes set on $10m in ARR and scaling a fractional COO division of the company as we speak!

What's your backstory and how did you come up with the idea?

I started my career by pulling out of med school and scaring the crap out of my parents haha. They are both entrepreneurs and they wanted me to have a “less stressful” life so encouraged me to get into medicine but when it came down to it spending that much time in school really freaked me out so I bailed.

Instead, I started an IT company (Link Technology) with my good friend and we built local cloud storage for small businesses to access files when away from the office. Ended up selling that to a local company and looking back on my life realize it was a massive mistake because we were essentially building Dropbox but didn't have the vision for it at 19!

From there I helped start a fundraising company for elementary schools (Apex Fun Run) with a tech slant to it which was a blast and we expanded that nationwide. Investors I met there actually ended up as our angels for Bara Agency which is cool.

Out of nowhere a friend of mine called me and said “Hey man I know you’re running the fundraising company but have you ever wanted to start a real estate team?” I laughed because that was a life trajectory that had never crossed my mind but we were close and his daughter is my god-daughter so I said sure!

We built that (Gluch Group) from him and I to operating in three states and selling 1000’s of homes. I personally sold about 200 homes in my time there and learned the ins and outs of real estate.

The only reason I split ways with my partner there is because two of my best friends and I got signed to Tooth and Nail Records to write 3 albums for them, which was kind of like one of those childhood dreams come true but more on that at another time!

I started doing some consulting while we were doing the music thing helping real estate companies streamline and scale their tech and I ended up doing what I swore I would never do - I built another real estate team. But I fell in love with what this gal was doing for the military community (CalzaCo) so we joined forces as partners and in two in a half years built it to the largest VA team in the state of AZ.

After that adventure, I finally decided to take a solid 6 months off of life. Had a young family and wanted to push the reset button to re-prioritize around family and being present with them and of course, it was in the middle of that time that Bara Agency emerged as an idea.

I had a ton of friends in the industry who were looking for tech help and would reach out to me asking if I knew of anyone “like me” that they could hire. A few actually offered me large equity stakes in their companies if I would do it but I was pretty burnt out on build teams at that point. I did really love the tech side so the idea dawned on me after learning about fractional CFO and CMO models that maybe a fractional CTO model could work.

So I called up a few of those friends that reached out and pitched an idea to try for 90 days that they would hire me on a fractional basis to be their CTO and after that 90 days we realized there was a huge opportunity here and decided to hit the gas to grow into an agency format.

We raised a small bit of funding ($200K) to hire and train the skillset since finding people who understand both tech and real estate is a tough ask and we haven’t looked back since!

Take us through the process of building and launching the first version of your product.

The first version was pretty easy actually since it was just me. I decided that I didn't really want to build a business that sold packs of hours or worked on a per-project basis due to the lumpy cash flow and non-recurring nature.

So instead we decided that our agency would work primarily on a retainer to lock down a certain amount of hours of our time per month to serve as the CTO of our client’s organization.

Our first month is pure discovery in which we end up going through an exercise to create a mind map of their technology and how things flow through their business and deliver a 6-month plan on how we will accomplish their goals moving forward.

I always explain that first month of paid discovery to clients like preparing for a major surgery. I don't want the surgeon to cut me open and figure it out while he’s in there, I want him to take imaging and develop a gameplan they feel absolutely confident in before I even step foot in that surgery room.

Since launch, what growth channels have been most effective for you?

Our growth channels have continued to evolve over the past two years. In the beginning, we leaned pretty hard on affiliate relationships to spread the word. I’ve learned in the past that the most “famous” people don't always make the best affiliates so I focused hard on finding the most influential people in a few niche communities to start and offered affiliate deals that were as high as the entire first month’s retainer as an affiliate fee.

Another thing to note is that I didn't present it as affiliate deals but as “Referral Fees” since that verbiage makes more sense to the real estate demographic we serve.

From there we found out that being a backstop to the SaaS company’s sales and support teams was a natural fit so we started to forge relationships where we were called upon to help address technical complexities to help those companies  land sales or keep current clients from churning which many times turned into us gaining a new client along the way and was a win for the SaaS company as well

Recently we’ve found great relationships with the sales and operations coaches in the industry in which we can help bridge the gap between ideas and execution.

The coaches are incredible sources of wisdom and motivation but at the end of the day, were often left frustrated by the lack of execution. So we get called in to help their clients execute the blueprint that the coach assembled which makes it a huge success for everyone involved.

Moving into the future I know we need to get into the online course game and public thought leadership as a great top-of-funnel feed. The lead incubation that will create for us seems like a no-brainer just have not had the time to get around to it and honestly that stuff really stresses me out haha.

Did you ever have an “oh shit” moment where you thought it wouldn’t work?

Haha “an”? Like as in only one?? What about 50 moments? Honestly, this has been one of the hardest companies to scale that I’ve ever been a part of. I’m what you call an “accidental agency owner” and I can tell you now that I have wicked respect for all the agency owners out there because this shit is not for the faint of heart.

In the early days, each time we needed to grow we had to hire ahead of the curve to train someone to be ready since people that understand tech and real estate both are pretty hard to find.

That caused paper-thin margins compounded by the fact that it was inevitable that the new person would make a mistake and some of those cost us clients early on or I’d be the one handling the stressful call to de-escalate things. I remember sitting in my truck one day after one of those hard conversations just so frustrated, tears in my eyes, wondering if it was even possible to scale. I even typed up an email to someone who I knew would buy us and hovered over the send button a few times a day for a week straight haha.

Honestly, I’m not sure why I never pressed send other than deep down I knew it would be because I was giving up and I have a bit of pride in my life as being someone that follows things through.

Outside of that, we have thankfully never had any huge catastrophes with tech or client data outside of one scare where a dev thought he overwrote a bunch of data in a database of hundreds of thousands of leads. I’m not going to lie, I think I stopped breathing for a few minutes when he told me what he thought had happened. Thank God it wasn't the case after all and all was well in the world. I guess that’s what our huge insurance policy is for!

Can you break down the keys to this business model for us? What makes it work? And What do outsiders typically not understand about your industry?

The agency retainer model has been around for a long time so I’d hate to bore everyone with explaining it. We chose that path because even if it’s often the hardest to sell upfront, in the long term it provides amazing stability for the organization as it grows which is much more important to me personally.

In the beginning, we only had two guiding principles as a company which were “Do what you say you’d do” and “Leave everyone better than you found them”. Which naturally became a culture that simply said, if we are reliable and build cool shit that helps people, the rest will take care of itself. Although we have a few more core values now, those two remain the most important and most quoted within our company.

Real Estate agents are a notoriously hard population to serve. Churn in the industry is often really hard because agents operate in a cyclical and sometimes feast or famine kind of income reality. That naturally causes churn to be high for companies that don't invest heavily in customer support and ultimately relationships with clients. If you can win at support you can win in the real estate products sector.

What platform/tools are absolutely crucial for your business?

Asana - it's honestly the core of our company. It’s where we store client information, manage projects, track hours, and keep track of capacity and performance. We tried a bunch of others like Monday, and ClickUp, and ultimately Asana was the perfect tool for us.

Retool - We build all of our internal tools here. Our onboarding application for new clients is built in retool along with a ton of other tools to fill the gaps between systems. Retool has also been incredible to use for clients as well since many of the projects we work on are not client-facing but mostly internal, the front-end components work really well and cuts our time to develop in half most of the time.

Everhour - We tried harvest, toggl, and probably 5 others and finally settled here. This is where we track true hours for every activity done by our team for clients or for internal work. Many of our bonus structures for employees are based around delivered hours or retained hours so this also feeds our reporting that does those calcs. Also integrates really well into Asana and has been so crucial to making sure we stay profitable on projects.

Notion - We have documentation on SaaS companies documentation at this point haha. It’s the brain of our company, our wiki, and the keeper of all our internal process documentation. We also house all of our training materials here and it’s been a godsend at organizing onboarding for new team members.

Clockwise - We use this a ton for automatic time blocking which has been so important for our system architects in particular. It allows them to sell Clockwise that they need a set amount of hours in time blocks to get things done for clients and it will intuitively reschedule when inevitable things come up that shuffle your calendar for the week.

Keap - It’s our CRM that includes phones, sms, landing pages, email, and billing. I know there are probably “better” platforms out there to use but I’ve used Keap since back in the Infusionsoft days and I just know it super well. It’s never steered us wrong other than being a bit slow at times.

What have been the most influential books, podcasts, or other resources?


  • MFM obviously haha I really mean it though. It’s a source of constant inspiration and often challenges the way you think which is so helpful.
  • Jason Swenk’s Smart Agency podcast has been helpful in gaining agency-specific knowledge and inspiration on how to expand from other successful agency owners.


  • The Outsiders by William N. Thorndike was eye-opening and helped me understand how much I had to learn when it comes to the capital allocation side of being a great CEO.
  • Essentialism by Greg McKeown is always an incredible return to making sure we are only focused on things we can full say “Hell yes” to.

What are some strong opinions you have about leadership, and how do you actually put those into practice in your company?

I can be a bit of an oversimplifier when it comes to how I lead a company because all roads lead back to one central belief that companies, especially service-based companies where I’ve had most of my life experience, should always keep their word to clients.

I know it sounds like a Sunday school teaching but in a world of service companies that consistently oversell clients and just to let them down (most biz owners have horror stories from consultants and agencies), keeping your word is one of the easiest ways to dominate and it’s much easier said than done. If you can do that inside of a niche then opportunity will likely come in absolute plenty.

I also really believe that your goal as a leader is not primarily to build a big company but to build big people.

Our core value of “leave people better than you found them” applies to our team as well and it’s my job to see that through. The more trusted and well-equipped “who’s” in your organization the less often you have to say no to opportunities due to capacity issues and most of the time I’ve had to pass up opportunities it was because of capacity issues not a lack of funding. Above and beyond that, these are incredible humans that are building your dream so it’s only fair that you also contribute to their dreams as well.

Where can we go to learn more?

Web -

Insta - @justinbenson

X (Twitter) - @justin_benson

Personally, I find being the CEO of a startup to be downright exhilarating. But, as I'm sure you well know, it can also be a bit lonely and stressful at times, too.

Because, let's be honest, if you're the kind of person with the guts to actually launch and run a startup, then you can bet everyone will always be asking you a thousand questions, expecting you to have all the right answers -- all the time.

And that's okay! Navigating this kind of pressure is the job.

But what about all the difficult questions that you have as you reach each new level of growth and success? For tax questions, you have an accountant. For legal, your attorney. And for tech. your dev team.

This is where Hampton comes in.

Hampton's a private and highly vetted network for high-growth founders and CEOs.

See if you're a fit...

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