10 Year overnight success!

Our Story

How we learned to solve problems with technology, not "hiring more people"


Who are "we"? 
Charlie Dolan and Brian Dolan.

We used to own the brokerage company, Sequoia Waste Solutions, from 2011 to 2022.

During our ownership, we learned a lot of lessons. Not always the easy way.

Those lessons helped us to build DSQ Technology, LLC and its products Discovery and Pioneer.

This is our story. Briefly! 

In 2013, Sequoia Waste Solutions, a then 2-year old waste & recycling brokerage company, was in a bad place.

Sequoia was:

     💸 Unprofitable
     🌋 Unscalable
     🚨 Basically Bankrupt
     🤨 Losing a Co-Founder

To save Sequoia, we:

     🧱 Re-built the Team
     💧 Plugged Leaks
     🛠️ Built Software
     💰 Controlled Finances

⏩ Fast-forward to 2022. Sequoia sold as a profitable business with a loyal customer base.

🌅 Today, we've scaled DSQ to a 30 person team and are operating profitably with no long term debt or outside funding.

Founding & Failing Fast (2011 - 2013)

Section 1

Background & The Big Idea:

In 2011, OakLeaf had sold to WM for $400,000,000. Oakleaf was focused on large, nationwide networks of name brand companies. Oakleaf is now Waste Management National Accounts.

We thought there was room for a more technology-driven customer-centric approach that appealed to small and medium sized businesses.

-> Our Vision: A "managed services" style waste & recycling brokerage company that would:

   - leverage excellent technology to scale faster by attracting the small to medium sized business customers and deliver them a better customer experience;

   - utilize optimized local recycling with high diversion rates for cardboard & paper;

   - realize cost savings for the brokerage company better than the "pen & paper" brokers & haulers.

We started thinking about Sequoia in Summer 2011 with big dreams and 3 founders. Each of the Founders had their speciality that they focused on:

  • financial controls & operations
  • technology vision
  • sales & customer experience

Fail Fast!

By the fall of 2013, Sequoia had grown quickly. Too quickly for our controls. Sequoia was unprofitable, had ineffective technology and could not scale (nor meet) its operational promises.

It would have been easier to bankrupt Sequoia than continue.

Why was Sequoia nearly bankrupt?

1. Off-the-shelf technology didn’t exist to run a brokerage company, so we had to tape together solutions on a tight budget.

2. Sequoia lost more money the faster it grew because of poor processes (ask about the algorithm in the iPad app) and unsuccessful financial/operational controls.

3. Financial management was silo'd - we missed the opportunity to set structure early and avoid future issues.

    Example: For over 2 years and millions in revenue, our invoices were being sent without invoice numbers!      When Customer paid, Sequoia was not 100% sure which invoice customers were paying!

4. Heavy reliance on people-first manual validation and corrections, due to low trust in our processes.

-> Key learning lesson: More Manual Labor is not a solution to your scalability problems!

-> Sunk cost attitude of “we paid for this, so use it better”.

Notable Facts & Figures from this period:

$3,000,000+ in "unapplied cash" backlog
"What did they pay us for??"
60+ days to close a fiscal period
"Are they delinquent? Or are we?"

Didn't Give Up.  Stopped Digging Holes (2014 - 2015)

Section 2

🪓  Re-org -> 4 key employees exited

🛑  Stop digging new & deeper financial and operational holes

✅  Secure funds to patch the balance sheet & cash flow

🎯  Set internal goals for Sequoia to achieve to make the brokerage excellent, even if using manual labor. These questions planted the seeds of future success.

    -> Every container has a margin.   "How to see this at any time?"

    -> Audit every line item to the penny.   "How to do this without people keying-in data by hand?"

    -> Cash Flow controls to know who paid.  "Did Sequoia receive customer's funds so it can pay the vendor?" 

    -> One Source of Truth for Financial and Operational records and actions.  "What is the status of that service issue or work order?"

    -> Contract Expiration & Procurement home. "When is this contract up? When is the notice window?"

Sounds simple. Wasn't easy! Especially with a manual process. It was brutal!

The team rebuilt Sequoia while in 'mid-flight'...against heavy headwinds

     -> Sequoia lost $500,000 operating in 2014 as we addressed issues. At the lowest point, the balance sheet showed negative equity of about $750,000.

     -> Sequoia lost two key employees to a new local competitor and another key employee to a new role (Two in Sales & the Operations lead).

The goal of 2014 was to stabilize and stop digging deeper holes.

After bottoming, Sequoia began climbing out...slowly.

Notable Facts & Figures from this period:

$500,000 operating loss in 2014
Early promises could bury us in coming months 🥴

Climbing. Building. (later 2015 - 2019)

Section 3

Charlie and Brian decided to build out of the hole with hard work and hopefully software. They now understood the scaling problems and financial missteps of the early Sequoia years.

     -> Think Long Term. They chose to remain as independent as possible and not seek venture funding. They wanted to build to their vision and not be on a fundraising timeline.

👨💻  In late 2015, we got lucky with a great hire to contribute to and eventually lead the technology effort.

He's been "fixing to get a coffee and push some code" ever since.

🤦 Between 2015-2018 there was a lot of trial and error, multiple dead-ends and "why didn't we think of that sooner?" moments. Knowing what you want to accomplish is not the same as figuring out how best to do it!

🏋️ We continued to invest our own capital into the business to continue to retain and build the technology team and the internal technology systems. We knew that we understood the problem, and needed time to continue to iterate.

🔑 By 2018, the technology existed for the narrow purpose of running Sequoia. We had tested it against the live company and knew that it could be trusted for that singular purpose. It wasn't yet available to anyone outside of Sequoia, nor would it have been valuable to them because it wasn't set up to "work" for any company but Sequoia. A lot of work still to do!

As we rolled through 2018 and into 2019, one area of focus was on making the software work for potential customers beyond Sequoia.

⚡️ We had kept in touch with some of Sequoia's competitors. They wanted to use our software because it was "light years* ahead of what they had on their own".

We worked with some "friends and family" in the industry to test and challenge the software until it was mature enough to take to market.

As we reached the end of 2019, we were finally in position to execute on our vision.

We had:

     -> a robust support team

     -> years of market experience

     -> technology that could scale and replace the old approach everyone had of "add another employee"

*Light Years:

Third party waste managers used to expect to “consistently, maybe, catch variances in line item costs of 15% - 20%”. This means on a $1,000 invoice, the change needed to be $150 to be noticed.

Being accurate to the penny was "light years ahead".

Notable Facts & Figures from this period:

1,500 Invoices processed monthly
$300,000 Lifetime Savings from Invoice Auditing

MVP viable. Go for launch!  (2020+)

Section 4

DSQ Technology quietly launched its first technology product, Discovery, in January 2020 to zero fanfare or announcement.

🤿 In March 2020, when people were wondering “now how do I get the mail?” during mandated lockdowns, the lightbulb went off for many brokers and managers.

Conversions to Discovery began in earnest. Due to our experience in the industry we knew most of the brokerages (and therefore sales prospects) for Discovery.

We performed direct sales outreach to these Discovery prospects using cheap but effective digital and mail campaigns. Our meeting take rates were extremely high and we demo'd the software multiple times per week for over a year. We were upfront about our history of running our own brokerage, Sequoia, and how the technology was built by brokers, for brokers.

The number one objection we encountered? "You also own a brokerage, Sequoia, and Discovery is software to run a brokerage. How can I trust that you won't take my data within Discovery for your brokerage Sequoia?"

The prospects had a reasonable concern. 🤔

With Discovery growing and the addressable market for the software increasing, Charlie and Brian began the process to sell Sequoia.

Sequoia was under contract in 2021. Sequoia was successfully turned from a liability into a success story, and we learned a ton along the way.

Now the focus would be 100% on the always-growing technology needs of DSQ's customers and how Discovery's software can help them to increase productivity by utilizing the time and talent of their existing employees more effectively.

Notable Facts & Figures from this period:

$18.00/Invoice Savings in 2020
$750,000 Lifetime Savings from Invoice Auditing

What's next? 

Section 5

Macro trends favor Discovery and Pioneer compactor monitors.

  • Fewer people want to do manual data entry work. It's boring and costly.
  • Consolidating companies need software that scales. Existing software doesn't speak trash, recycling or broker.
  • Data & reporting is always more complex. There is less time to get it done, with fewer qualified people.

Discovery & Pioneer are leading the way forward with software automation and customer driven solutions that don't require adding more bodies in AP & AR roles.

We’re bullish at DSQ because we can see over the horizon that the opportunity is still growing.

8 days gained in AR& AP process when switching
from manual process to Discovery
$22.00/Invoice Savings in 2022

Thank You

To be continued...

Whether you are seeking to join us as a customer, partner with us through our API, or to join the team at DSQ, we’re grateful that you took the time to read our story.

- Charlie and Brian

Explore our products

A product screenshot from the Discovery web application

Audit & Report

  • Scale your waste business faster with Discovery automation
  • Reduce manual workload and centralize information with one easy-to-use platform
  • Measure financial and sustainability impact with data-driven reporting

A screenshot from the Hauler web application software


  • Run a roll off or junk removal business easier with Hauler software
  • Track bins, dispatch, invoice and more with one user-friendly platform
  • Communicate in real-time with free customer text messaging and the Hauler Driver App
A screenshot of the Pioneer monitoring system

Monitor Compactors

  • Monitor fullness and schedule efficient hauls with Pioneer automation
  • Avoid pack-outs and underweight hauls with predictive technology
  • Provide real-time insights and business data with detailed reporting